Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/64—Oxygen atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
  • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
  • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
  • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/66—Nitrogen atoms not forming part of a nitro radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
  • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
  • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to the new catechol molecules and their use as inhibitors to P450 related metabolic pathways.
• the invention further relates to a method of controlling crop pests and/or non-crop pests that are resistant to one or more insecticide(s) and method of controlling undesired vegetation that are resistant to one or more herbicide(s) by applying at least one in hibitor to P450 related metabolic pathways of formula (I).
• the World Health Organization has defined resistance as“the development of an ability in a strain of insects to tolerate dose of toxicant that would prove lethal to the majority of individuals in a normal population of the same species”.
• IRAC Insecticide Resistance Action Committee
• resistance may be defined as‘a heritable change in the sensitivity of a pest population that is reflected in the repeated failure of a product to achieve the expected level of control when used according to the label recommendation for that pest species’ (www.irac- online.org).
• Cross-resistance occurs when resistance to one insecticide confers resistance to another insecticide, even where the insect has not been exposed to the latter product.
• Pesticide resistance and herbicide resistance is therefore to be similarly construed.
• the resistant may be partial or complete and it will be appreciated that all degrees of resistance are included the meaning of this term, whether they be very low resistance, low resistance, high resistance, very high resistance or total resistance.
• Natural selection by a pesticide allows some naturally occurring, pre-adapted pests with re sistance genes to survive and to pass-on the resistance trait to their offspring.
• selection for the resistant individuals persists so the proportion of resistant pests in the population increases, while susceptible individuals are eliminated by the pesticide. Under this permanent selection pressure, resistant pests outnumber susceptible ones and the pesticide is no longer effective.
• the speed with which resistance de velops depends on several factors, including how fast the pests reproduce/grow, the migration and host range of the pest, the availability of nearby susceptible populations, the persistence and specificity of the crop protection product, and the rate, timing and number of applications made. Resistance increases e.g. in greenhouses, where pests reproduce/grow quickly and when there is little or no immigration of susceptible individuals and the user may spray frequent ly (https://www.irac-online.org/about/resistance/).
• the insecticide resistant insects can detoxify by destruction or excretion in comparison to normal non-resistant insects, e.g. due to their metabolism such as their enzyme systems. Metabolic resistance is very often dependent on the structure of the active ingredient. There fore, the metabolic resistance is most likely overcome by actives with a different chemical struc ture.
• Another resistance mechanism is a modification of the target structure (protein, receptor, ion channel, etc.) of the insecticide. The insecticidal activity is reduced by a change in the bind ing site, e.g. due to point mutations, which are passed on. Further, there is also resistance due to behavioral change and penetration resistance (the outer shell of the insect developed barriers that slow down the penetration of insecticides in the body of the insect). In resistant pests, a combination of several of these resistance mechanisms can be found.
• MFOs mixed-function oxidase system
• the MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides such as pyrethrins and the synthetic pyre- throids. It’s effect on GST pathway is very limited (Casida, J. E. (1970). MFO involvement in the biochemistry of insecticide synergists. J. Agric. Food Chem. 18, 753-772).
• IRM Insecticide Resistance Management
• IPM integrated pest management
• Insects have several pathways to metabolize exogenous molecules that they are exposed to. These molecular transformations can either activate an insecticide, such is the case of pro drugs. Alternatively, these mechanisms can also confer the insect what is known as metabolic resistance. In this instance, the metabolism of the insect transforms the insecticide molecules in such way they are deactivated and become harmless to the insects and easily excretable.
• Esterases Catalyze the hydrolysis of ester-insecticides into their respective acid and alcohol compounds. This process increases the polarity of the compounds making them easier to ex crete. Esterases can also sequester some insecticides in such way that they are not available for interaction with the insect proteins making them non-toxic to the insect.
• One of the most known examples is the insecticide detoxification by the overproduction of a specific carboxyles- terase in the green peach aphid Myzus persicae (Hemiptera: Aphididae). (Field et al., 1988; Bizzaro et al., 2005; Rivi et al., 2013).
• Glutathione S-transferases GST. Insect GSTs are divided into two different groups (microso mal and cytosolic) according to their location within the cell, but only the latter has been impli cated in the metabolism of insecticides.
• the GST pathway catalyzes the conjugation of the reucked form of glutathione to xenobiotic substrates for the purpose of detoxification and then easy excretion.
• DDT deactivation by DDT- dehydrochlorinase GST which also has been reported as being responsible for DDT resistance in houseflies and mosquitoes (Enayati et al., 2005).
• Puinean AM Foster SP, Oliphant L, Denholm I, Field LM, Millar NS et al.
• Amplification of a cy tochrome P450 gene is associated with resistance to neonicotinoid insecticides in the aphid Myzus persicae. PLOS Genet 6:e1000999, 2010.
• the present invention relates to a compound of formula (I)
• R 2 is OR 7 , N0 2 , NR 8 R 9 , (CR 5 R 6 ) n C3-Ci2-cycloalkyl whereby C3-Ci 2 -cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0 2 or together with R 3 forms C3-Ci2-cycloalkyl whereby C3-Ci 2 -cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0 2 ;
• R 7 is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R 12e which are independently selected from the group consisting of F, Cl, Br, I , OH, SH , CN , N0 2 , N R 10 R 11 , O-C1-C12-alkyl, 0-C 2 -Ci 2 -alkenyl, 0-C 4 -C 6 -alkynyl, Ci-Ci 2 -alkyl, C 2 -Ci 2 -alkenyl
• R 8 and R 9 are selected from the group consisting of H, OH , N R 10 R 11 ,
• R 3 is selected from group consisting of Ci-Ci 2 -alkyl, C 2 -Ci 2 -alkenyl, C 2 -Ci 2 -alkynyl, (CR 5 R 6 ) n C 5 - Ci 4 -aryl, (CR 5 R 6 ) n Cs-Ci4-heteroaryl, (CR 5 R 6 ) n C3-Ci 2 -cycloalkyl, (CR 5 R 6 ) n C3-Ci 2 -heterocycloalkyl, (CR 5 R 6 ) n C3-Ci2-heterocycloalkenyl and (CR 5 R 6 ) n C3-Ci 2 -heterocycloalkynyl; whereby R 3 is un substituted or further substituted by 1 , 2, 3 or 4 identical or different groups R 12 a which are inde pendently selected from the group consisting of F, Cl, Br, I , OH , SH, CN
• R 10 and R 11 are H, C3-Ci2-cycloalkyl, C2-C 12-alkenyl, C2-Ci2-alkynyl or Ci- C12 alkyl or R 10 together with R 11 forms C 5 -Ci 2 -membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or C 5 -Ci4-membered heteroaryl;
• R 12 and R 13 are H, C3-Ci2-cycloalkyl, C 2 -C 12-alkenyl, C 2 -Ci 2 -alkynyl or Ci- C12 alkyl or R 12 together with R 13 forms C5-Ci2-membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or Cs-C M -membered heteroaryl;
• R 4’ is C1-C6 alkyl, C5-C6 cycloalkyl, C 2 -C6 alkenyl.
• the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.
• the term “consisting of' is considered to be a preferred embodiment of the term “comprising of. If hereinafter a group is defined to com prise at least a certain number of embodiments, this is meant to also encompass a group which preferably consists of these embodiments only. Furthermore, the terms “first”, “second”, “third” or “(a)”, “(b)”, “(c)”, “(d)” etc. and the like in the description and in the claims, are used for distin guishing between similar elements and not necessarily for describing a sequential or chronolog ical order.
• C u -C w indicates the number of carbon atom possible in each case.
• Ci-Ci 2 -alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 12 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,
• C 2 -Ci2-alkenyr refers to a straight-chain or branched unsaturated hydrocarbon radi cal having 2 to 6 carbon atoms and a double bond in any position.
• Examples are "C 2 -C4-alkenyl” groups, such as ethenyl, 1 -propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1 -methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.
• C 2 -Ci 2 -alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
• Examples are "C 2 -C 4 al- kynyl” groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl, but-1 -ynyl, but-2-ynyl, but-3-ynyl, 1 - methyl-prop-2-ynyl.
• C3-Ci 2 -cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
• Cs-Cn-aryl refers to monocyclic and polycyclic aromatic radicals, for example C5-C6- aryl radicals, for example phenyl or cyclopenta-1 ,3-diene, or, C «rCi 4 -aryl radicals, for example, naphthalene or anthracene.
• C 5 -Ci 4 -heteroaryl means an aryl group where at least one carbon atom on the hy drocarbon chain normally carrying 5 to 14 carbon atoms is substituted by another atom selected from N, O, oxo or S, for example, pyridyl, pyridinone, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazol- yl, thiadiazolyl, oxadiazolyl and tetrazolyl rings. Any monocyclic which has the characteristics of aromaticity in terms of electron distribution throughout the ring system is included in this defini tion.
• C5-Ci 4 -membered heterocycloalkenyl refers to 5 to 14 membered monocyclic ring system having one or more heteroatoms, such as O, N, oxo, S as ring members and one or more double bonds.
• C5-C6-heterocycloalkenyl refers to a cyclic unsatu rated hydrocarbon residue with 5 or 6 carbon atoms, which comprises at least one double bond, and wherein, one or more C atoms are replaced by heteroatoms independently selected from O, N, oxo or S, for example, (2,3)-dihydrofuranyl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1 ,4)-dihydropyridin-1-yl, di- hydropyranyl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3- dihydropyrazol-4-yl, 2,3-d
• C 5 -Ci4-membered heterocycloalkyl means a non-aromatic monocyclic or polycyclic ring comprising 5 to 14 carbon atoms and at least one heteroatom selected from O, S, oxo and N.
• a heterocycloalkyl group can have one or more carbon-carbon double bonds or carbon- heteroatoms double bonds in the ring as long as the ring is not rendered aromatic by their pres ence.
• heterocycloalkyl groups include aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl and pyranyl.
• Another embodiment of the present invention relates to the compound of formula (I), wherein R 1 is H or OCH 3 and R 4 is H, or
• R 1 is H or OCH 3 and R 4 is halogen, or
• R 1 is halogen and R 4 is H, or
• R 1 is halogen and R 4 is halogen
• R 2 is OR 7 or N R 8 R 9 , wherein
• R 7 is H, Ci-Ci2-alkyl, (CR 5 R 6 ) n C5-Ci 4 -aryl, (CR 5 R 6 ) n C5-Ci 4 -heteroaryl or (CR 5 R 6 ) n C 5 -Ci 4 -aryl- C 3 - Ci2-membered heterocycloalkyl;
• R 8 and R 9 are selected fromH and (CR 5 R 6 ) n C5-Ci 4 -aryl;
• R 3 is selected from the group consisting of C1-C 12-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl and C 3 - C 12 -cycloalkyl; whereby R 3 is unsubstituted or further substituted by 1 , 2 or 3 identical or differ ent groups R 12 a which are independently selected from the group consisting of F, Cl, Br, I, C2- Ci2-alkenyl, C 2 -Ci2-alkynyl, C3-Ci 2 -cycloalkyl, C 5 -Ci 4 -aryl, C 5 -Ci 4 -heteroaryl, S-(CR 5 R 6 ) n -C 5 -Ci 4 - aryl and S0 2 (CR 5 R 6 )n(C 5 -Ci 4 -aryl); and n is 0,1 ,2 or 3.
• X is F, Cl, Br or I and R 5 is selected from the group consisting of H, F, Cl,
• C 0(Ci-Ci 2 -alkyl), CrCi 2 -alkyl, C 2 -Ci 2 -alkenyl and C 2 -Ci2-alkynyl;
• X a is F, Cl or I.
• the present invention relates to an agrochemical mixture comprising at least one compound of formula (I) in free form or in the form of a stereoisomer or an agricultur ally acceptable salt or a tautomer or an isotopic form or a N-oxide or a S-oxide or a prodrug thereof, and at least one insecticidally active substance.
• the present invention relates to a composition
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer or an agriculturally ac ceptable salt or a tautomer or an isotopic form of a N-oxide or a S-oxide or a prodrug thereof, and an auxiliary.
• the compounds according to the present invention may be provided as mixtures with at least one mixing partner such as an insecticide, herbicide or biopesticide, or as compositions com prising an auxiliary and at least one compound of the present invention or a mixture thereof. Suitable formulations will be described further below.
• the compound of the formula (I) may have one or more centres of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
• the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.
• Suitable compounds of the formula (I) also include all possible ge ometrical stereoisomers (cis/trans isomers) and mixtures thereof.
• Cis/trans isomers may be pre sent with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
• the term "stereoisomer(s)” encompasses both optical isomers, such as enantio mers or diastereomers, the latter existing due to more than one centre of chirality in the mole cule, as well as geometrical isomers (cis/trans isomers).
• tautomer refers to the coexistence of two (or more) compounds that differ from each other only in the position of one (or more) mobile atoms and in electron distribution, for example, keto-enol tautomers.
• Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic function ality.
• suitable“agriculturally useful salts” or“agriculturally acceptable salts” are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
• Suitable cations are in particular the ions of the alkali metals, preferably lithi um, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH 4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C 4 -alkyl, Ci-C 4 -hydroxyalkyl, Ci-C 4 -alkoxy, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, hydroxy-Cr C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl.
• substituted ammonium ions comprise me- thylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trime- thylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sul- fonium ions, preferably tri(Ci-C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C 4 - alkyl)sulfoxonium.
• Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
• the compound of formula (I) may be present in the form of their N-oxides.
• N-oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
• N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
• a suitable oxidizing agent such as peroxo carboxylic acids or other peroxides.
• the compounds of the present invention may be amorphous or may exist in one or more differ ent crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
• the present invention includes both amorphous and crystalline compounds of formula (I), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
• isotopic forms or “isotopically labeled forms” is a general term used for isotopic forms of compounds of formula, wherein one or more atoms of compounds of formula (I) are replaced by their respective iso topes. All isotopes of any particular atom or element as specified are contemplated within the scope of the compounds of the invention.
• isotopes that may be incorporated into the compounds disclosed herein include, but are not limited to, isotopes of hydrogen such as 2 H (deuterium or D) and 3 H, carbon such as 11 C, 13 C and 14 C, nitrogen such as 13 N and 15 N, oxygen such as 15 0, 17 0 and 18 0, chlorine such as 36 CI, fluorine such as 18 F and sul-phur such as 35 S.
• isotopic forms of the compounds of formula (I) may include, without limitation, deuterated compounds of formula (I).
• deuterated as used herein, by itself or used to modify a compound or group, refers to replacement of one or more hydrogen at- om(s), which is attached to carbon(s), with a deuterium atom.
• co-crystal denotes a complex of the compounds according to the invention or a ste reoisomer, salt, tautomer or N-oxide thereof, with one or more other molecules (preferably one molecule type), wherein usually the ratio of the compound according to the invention and the other molecule is a stoichiometric ratio.
• solvate denotes a co-complex of the compounds according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof, with solvent molecules.
• the solvent is usually liquid. Examples of solvents are methanol, ethanol, toluol, xylol.
• a preferred solvent which forms solvates is water, which solvates are referred to as“hydrates”.
• a solvate or hydrate is usually characterized by the presence of a fixed number of n molecules solvent per m molecules com pound according to the invention.
• active compound denotes one or more compound selected compound of formula (I) and/or insecticide and/or herbicide.
• the term“pesticidally active compound” denotes one or more compound selected from insecti cide and/or biopesticide and/or herbicide.
• Agronomically acceptable salts of the compound(s) of formula (I) can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
• resistance therefore means that the original activity of a pesticide against the target organisms (arthropods, insects) decreases or is even lost, due to genetic ad aptation of the target organism.
• “Resistant” to an insecticide and/or herbicide is understood to mean resistant to at least one insecticide and/or herbicide respectively, i.e. the insect and/or undesired vegetation may be resistant to only one, but also to several insecticides and/or herbicide respectively.
• the resistance may be also against an insecticidal effect which is due to a genetic modification of a plant (modified or transgenic plant), which caused a resistance of the plant or crop to cer tain pests, especially insect pests, in susceptible insects.
• insecticidal proteins especially those mentioned herein, es pecially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, Crylll B(b1 ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal pro teins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., and so on.
• VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
• the compounds of formula (I) of the present invention can be applied in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions compris ing said mixtures as defined above.
• the components of said mixture can be applied simultane ously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture“in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
• the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
• Suitable application methods include inter alia soil treatment, seed treatment, in furrow applica tion, and foliar application.
• Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
• Seed treatment tech niques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
• furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying at least one compound of formula (I) and pesticidally active com pound to the furrow, and closing the furrow.
• Foliar application refers to the application of the compound of formula (I) and pesticidally active compound to plant foliage, e.g. through spray equipment.
• pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as https://www.pherobase.com.
• contacting includes both direct contact (applying the com
• animal pest includes arthropods, gastropods, and nematodes.
• Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop in sect pests.
• crop refers to both, growing and harvested crops.
• plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
• iceberg lettuce chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cu curbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
• Preferred plants include potatoes sugar beets, tobacco, wheat, rye, bar-ley, oats, rice, corn, cotton, soybeans, rapeseed, leg umes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cu cumbers, tomatoes, beans or squashes.
• plant is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a com bination thereof. Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
• rapeseed e.g. oilseed rape
• one or more genes have been mutagenized or integrated into the genetic material of the plant.
• the one or more mutagenized or inte-grated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1 , and ppo5.
• the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered
• herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
• Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape be ing tolerant to imidazolinones, e.g. imazamox.
• Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increas ing importance.
• plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhi zomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
• seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
• pesticide refers to insecticides and/or herbicides.
• pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
• the pesticidally effective amount can vary for the various com
• a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and dura tion, weather, target species, locus, mode of application, and the like.
• the quantity of active ingredients ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
• the rate of application of the active in gredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hec tare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
• the compounds of the formula (I) of invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects.
• the invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pre-germination with a composition comprising at least one compound of formula (I) of the invention and at least one active ingredient selected from insecticide.
• the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.
• seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
• seed treatment application of the compound of formula (I) is carried out by spraying or by dusting the seeds before sowing of the plants and before emer gence of the plants.
• the invention also comprises seeds coated with or containing at least one compound of formula (I) of the invention and at least one active ingredient selected from insecticide.
• coated with and/or containing generally signifies that the active ingredients are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of applica tion. When the said propagation product is (re)planted, it may absorb the active ingredients.
• Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, orna mentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, ba nanas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucum bers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
• the at least one compound of formula (I) of the invention may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineer ing, and which e.g. tolerate the action of herbicides or insecticides. Such modified plants have been described in detail above.
• Conventional seed treatment formulations include for example flowable concentrates FS, solu tions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the lat ter. Preferably, the formulations are applied such that germination is not included.
• a FS formulation is used for seed treatment.
• a FS formu lation may comprise 1-800 g/l of active ingredient selected from at least one compound of for mula (I), 1-200 g/l Surfactant, 0 to 200 g/l anti-freezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
• Especially preferred FS formulations of the compounds of the invention for seed treatment usu ally comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient selected from at least one compound of formula (I), from 0.1 to 20 % by weight (1 to 200 g/l) of at least one sur factant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
• a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and op tionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
• a binder sticker /adhesion agent
• a preservative such as a biocide, antioxidant or the like
• the application rates of the compounds of formula (I) of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
• the invention therefore also relates to seed comprising a compound of the invention, or an agri culturally useful salt thereof, as defined herein.
• the amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
• the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.
• the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.
• the present invention provides a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant.
• the present invention provides a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which insects are resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which insects are resistant.
• the present invention provides a method of protecting a crop of useful plants susceptible to and/or under attack by insects, which are resistant to an insecticide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insecticide resistant insects, a composition comprising at least one com pound formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.
• a composition comprising at least one com pound formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insect
• the present invention provides a method of controlling resistance to one or more insecticides in insects, which comprises alternately or simultaneously applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the insecticide, towards which the insects are re sistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects.
• the present invention provides a method, which process comprises treating the insect, the plant, or the plant propagation material selected from the group consist ing of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against insect attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with an effective amount of at least one compound of formula (I) in free form or in the form of a stereoi somer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, to wards which insects are resistant.
• the plant propagation material selected from the group consist ing of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against insect attack
• the present invention provides a method, wherein the step of treat ing the seed is followed by a treatment of the emerged host plants with a composition comprising at least one compound of formula (I), in free form or in the form of a stereoisomer, an agri culturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a de rivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.
• a composition comprising at least one compound of formula (I), in free form or in the form of a stereoisomer, an agri culturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a de rivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.
• the present invention provides a method of controlling resistance to one or more insecticides in insects, which comprises alternately or simultaneously applying at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the insecticide, towards which the insects are resistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects; wherein the insecticide to which the insect is resistant is from the following list of pesticides, grouped and numbered according the Mode of Action Classification of the Insecti cide Resistance Action Committee (I RAC).
• I RAC Mode of Action Classification of the Insecti cide Resistance Action Committee
• M.1 Acetylcholine esterase (AChE) inhibitors M.1A carbamates, e.g.
• aldicarb alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
• methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;
• M.2. GABA-gated chloride channel antagonists M .2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
• M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
• M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
• M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
• M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;
• M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
• M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
• M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
• chlorfenapyr DNOC, or sulfluramid
• Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
• M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
• Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
• Octopamin receptor agonists e.g. amitraz
• M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
• M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and in secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;
• M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]- , ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]- , methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetra
• M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
• Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
• M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
• M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
• M.28.3 cyclaniliprole
• M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl ⁇ -'amino)benzoyl]-1 ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-'carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)
• M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
• M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,
• M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
• M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
• M.UN.8 fluazaindolizine ; M .UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-
• M .UN .9.b fluxametamide
• M.UN.10 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
• M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-Htrifluoromethyl ⁇ ethyll-O- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S- ⁇ -iodo ⁇ -ll ⁇ -tetrafluoro-l-Ctrifluoromethy -'ethyll-e-
• M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ⁇ -tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoylJ-'phenyll ⁇ -methyl- benzamide; M.UN.
• M.UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;
• M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c)
• M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
• M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M.UN.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
• M.U N.16h N-methyl-1-(2-fluoro-1-methyl-propyl
• M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M.UN.17c N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide
• M.UN.17d 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide
• M.UN.17e 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide
• M.UN.17f methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydr
• M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
• M. UN.18b N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
• M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
• M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
• M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4FI-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
• M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456.
• M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839.
• M.4A.2, guadipyr is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO
• M.22B.1 is described in CN 10171577 and M.22B.2 in CN 102126994.
• Spiropidion M.23.1 is known from WO 2014/191271.
• M .28.1 and M .28.2 are known from W02007/101540.
• M.28.3 is described in W02005/077934.
• M.28.4 is described in W02007/043677.
• M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO
• M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911.
• M.UN.5 is de scribed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672.
• M.U N.8 is known from WO2013/055584.
• M .UN .9.a) is described in WO2013/050317.
• M.UN.9.b) is described in WO2014/126208.
• M.UN.10 is known from WO2010/060379.
• Broflanilide and M.UN.H .b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO 2010/127926.
• M.UN.12.a) to M.UN.12.C) are known from WO2010/006713
• M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO
• M. UN.14a) and M. UN.14b) are known from W02007/101369.
• M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
• M. UN.17a) to M.UN.17 ) are described in WO2015/038503.
• M.UN.18a) to M.UN.18d) are described in US2014/0213448.
• M.UN.19 is de-scribed in WO2014/036056.
• M.UN.20 is known from WO2014/090918.
• M.UN.21 is known from EP2910126.
• M. UN.22a and M. UN.22b are known from WO2015/059039 and W02015/190316.
• M.UN.23a and M .UN .23b are known from WO2013/050302.
• M.UN.24a and M. UN.24b are known from WO2012/126766.
• Acynonapyr M.U N.25 is known from WO
• Benzpyrimoxan M .UN.26 is known from W02016/104516.
• M.UN.27 is known from WO2016174049.
• the present invention provides a method, wherein the resistant in sects developed resistance against insecticides, avermectins, milbemycins, cyclodienes, phos phines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta- ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators or antifeedants.
• the resistant insects developed resistance against pyrethrums, pyrethroids, spynosins and/or anthranilamide.
• a method of controlling insects which are resistant to a neonicotinoid insecticide comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof to said resistant insects as cytochrome P450 inhibitor and the neonicotinoid insecticide.
• a method of controlling insects which are resistant to a pyrethroid insecticide such as such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, e
• a pyrethroid insecticide such
• a method of controlling insects which are resistant to an organophosphate insecticide such as primicarb, which method com prises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the organophosphate insecticide, to said resistant insects.
• the present invention provides a method of controlling insects, which are resistant to an insecticide, are from the order Lepidoptera, from the order Coleoptera, from the order Diptera, from the order Thysanoptera, from the order Hemiptera, from the order Hymenop- tera, from the order Orthoptera, from the class Arachnida, from the Phylum Nematoda, from the order Isoptera, from the order Blattodea from the order Siphonoptera, from the order Thysanura, from the class Chilopoda, from the class Diplopoda, from the class Symphyla, from the order Dermaptera, from the order Collembola, from the order Isopoda, from the order anoplura, from the Phylum Mollusca or from the order Phthiraptera, which method comprises applying a com position comprising at least one compound of formula (I) in free form or in the form of a stereoi somer, an agriculturally acceptable
• Lepidoptera such as Plutella maculipennis, Plutella xylostella, Trichophaga tapetzella, Trichop- lusia spp.
• the method of the present invention control pests of the suborder of Arachnida including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. such as P. ulmi, P. citri; Me- tatetranychus spp.
• Eotetranychus spp. Eutetranychus spp.
• Oligonychus spp. Oligonychus spp.
• Petrobia latens Tetranychus spp.
• Tetranychus spp. such as T. cinnabarinus, T. evansi
• Another embodiment of the invention provides a method of controlling species of insects, which have shown resistance effects against insecticides, in particular from the order of Hemiptera with their suborder of Homoptera and Heteroptera, but also from the orders Thysanoptera, Lep idoptera, Coleoptera or Diptera.
• the method of the present invention may further control pests of the suborder heteroptera including bugs, such as shield bugs, seed bugs, assassin bugs, flower bugs, stink bugs, sweetpotato bugs and the water bugs.
• bugs such as shield bugs, seed bugs, assassin bugs, flower bugs, stink bugs, sweetpotato bugs and the water bugs.
• the invention also provides a method of protecting a crop of useful plants, wherein said crop is susceptible to and/or under attack from insects, which are resistant towards insecticide.
• Such a method involves applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a composition comprising at least one compound of formu la (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cyto chrome P450 inhibitor and the insecticide, towards which insects are resistant.
• the compound of formula (I) of the present invention are effective through both contact and ingestion.
• the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
• the compounds of the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
• insects from the order of Lepidoptera for example Achroia grisella, Ac/eris spp. such as A. fim- briana, A. g!overana, A. variana; Acro/epiopsis assectella, Acronicta major, A doxophyes spp. such as A. cyrtosema, A. orana; Aedia leucometas, Agrotis spp. such as A. exdamationis, A. fucosa, A. ipsi/on, A. orthogoma, A. segetum, A.
• Cactoblastis cactorum Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, ChHo pp. such as C. Indi- cus, C. suppressa/is, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conf!ictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C.
• kuehniella kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiellas ., Eulia spp., EupoecHia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. such as F. subterra nean; Galleria mellonella, Gracillariaspp., Grapholitaspp. such as G. funebrana, G. mo!esta, G.
• H. armigera Heliothis armigera
• H. zea Heliothis zea
• He/iothis spp. such as H. assulta, H. subftexa, H. virescens
• Hellula spp. such as H. undalis, H.
• Lymantria spp. such as L. dispar, L. monacha; Lyonetia cierkeiia, Lyonetia prunifoiieiia, Maiaco- soma spp. such as M. americanum, M. caiifornicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quin- quemacuiata, M.
• Marasmia spp Marmara s ., Maruca testuiaiis, Megaiopyge ianata, Meianchra picta, Meianitis ieda, Mods spp. such as M. iapites, M.
• nubiiaiis nubiiaiis; Ouiema oryzae, Paieacrita vernata, Panoiis fiammea, Parnara spp., Papaipema nebris, Papiiio cresphontes, Paramyeiois transiteiia, Paranthrene regaiis, Paysandisia archon, Pectinophora spp. such as P. gossypieiia; Peridroma saucia, Pierieucoptera spp., such as P. coffeella; Phaiera bucephaia, Phryganidia caiifornica, Phthorimaea spp. such as P.
• opercuieiia Phyiiocnistis citreiia, Phyiionorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; PHocrocis tripunctata, Piathy- pena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P.
• insects from the order of Coleoptera for example Acaiymma vittatum, Acanthoscehdes obtec- tus, Adoretus spp., Ageiastica aini, Agriius spp. such as A. anxius, A. pianipennis, A. sinuatus; Agriotes spp. such as A. fuscicoiiis, A. iineatus, A.
• Aiphitobius diaperinus Amphimai- ius soistitiaiis, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomaia corpuien- ta, Anomaia rufocuprea, Anopiophora spp. such as A. giabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogo- nia spp., Athous haemorrhoidaiis, Atomaria spp. such as A.
• Attagenus spp. Auia- cophora femoraiis, Biastophagus piniperda, BHtophaga undata, Bruchidius obtectus, Bruchus spp. such as B. ientis, B. pisorum, B. rufimanus; Byctiscus betuiae, Callidiellum rufipenne, Cai- iopistria f/oridensis, Caiiosobruchus chinensis, Cameraria ohrideiia, Cassida nebuiosa, Ceroto- ma trifurcata, Cetonia aurata, Ceuthorhynchus spp.
• C. assimiiis such as C. assimiiis, C. napi; Chaetocnema tibialis, Cieonus mendicus, Conoderus spp. such as C. vespertinus; Conotracheius nenuphar, Cosmopolites spp., Costeiytra zeaiandica, Crioceris asparagi, Cryptoiestes ferrugineus, Cryp- torhynchus iapathi, Ctenicera spp. such as C.
• Curcu/io spp. Cyiindrocopturus spp., Cyciocephaia spp., Dactyiispa baiyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. iongicornis, D. semipunctata, D.
• Diaprepes ab breviates, Dichoc rods spp., Diciadispa armigera, Diioboderus abderus, Diocaiandra frumenti (Diocaiandra stigmaticoiiis), Enaphaiodes rufuius, Epi/achna spp. such as E. varivestis, E vigintioctomacuiata; Epitrix spp.
• hypomeces squamosus Hypothenemus spp., ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lath- rid ius spp., Lema spp. such as L. biiineata, L meianopus; Leptinotarsa spp. such as L. decem- iineata; Leptispa pygmaea, Limonius catifornicus, Lissorhoptrus oryzophiius, Lixus spp., Lu- perodes spp., Lyctus spp. such as L.
• aiternatus Naupactus xanthographus, Niptus holo/eucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephiius surinamensis, Oryzaphagus oryzae, Otiorrhyn- chus su/catus, Otiorrhynchus ova t us, Otiorrhynchus su/catus, Ouiema meianopus, Ouiema ory zae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P.
• vuineratus Sudperda Candida, Sco/ytus schevyrewi, Scyphophorus acupunctatus, Sitona iineatus, Sitophiius spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. ievis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphy/etes spp., Tanymecus spp., Tenebrio moiitor, Tenebrioides mauretanicus, Tribolium spp.
• T castaneum such as T castaneum; Trogoderma spp., Tychius spp., Xyiotrechus spp. such as X. pyrrhoderus; and, Za- brus spp. such as Z. tenebrioides;
• insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha iudens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gambiae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A.
• Aedes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha iudens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gambiae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacu
• G. intestinalis such as G. intestinalis; Geomyza tipunctata, Giossina spp. such as G. fusci- pes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippeiates spp., Hylemyia spp. such as H. piatura; Hypoderma spp. such as H. Hneata; Hyppo- bosca spp., Hydrellia phiiippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifo- iii; Luc i Ha spp.
• L. caprina such as L. caprina, L. cuprina, L. sericata; Lycoria pectora!is, Mansonia titillanus, Mayetio/a spp.
• Musca spp. such as M. autumnalis , M. domestica; Musci- na stabu!ans, Oestrus s . such as O. ovis; Opomyza ftorum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. anti- qua, P. brassicae, P.
• T. atratus such as T. atratus, T bovinus, T. iineoia, T simiiis; Tannia spp., Thecodi- piosis japonensis, Tipuia oieracea, Tipuia paiudosa, and Wohifahrtia spp;
• insects from the order of Thysanoptera for example, Baiiothrips biformis, Dichromothrips cor- betti, Dichromothrips ssp., Echinothrips americanus, Enneothrips Havens, Frankiimaschineia spp. such as F. fusca, F. occidentaiis, F.
• Heiiothrips spp. Hercinothrips femoraiis, Kakothrips spp., Microcephaiothrips abdominaiis, Neohydatothrips samayunkur, Pezothrips keiiyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchae- tothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. such as T. imagi nes, T. hawaiiensis, T. oryzae, T. paimi, T. parvispinus, T. tabaci;
• insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hiiare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Ade/ges iaricis, Ade/ges tsugae,
• a del phoc oris spp. such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Au- iacorthum soiani, Aieurocanthus wogiumi, Aieurodes spp., Aieurodicus disperses, Aleurofobus barodensis, Aieurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis car- dui, Aonidieiia spp., Aphanostigma piri, Aphiduia nasturtii, Aphis spp.
• Bliss us spp. such as B. ieu- copterus
• Brachycaudus spp. such as B. cardui, B. heiichrysi, B. persicae, B. prunicoia
• Brachy- co/us spp. Brachycoryneiia asparagi, Brevicoryne brassicae, Cacopsyiia spp. such as C. fuigu- raiis, C.
• Chrysomphaius aonidum Chrysomphaius aonidum, Cryptomyzus ribis, Ctenarytaina spatuiata, Cyrtopeitis notatus, Daibu- ius spp., Dasynus piperis, Diaieurodes spp. such as D. citrifoiii; Daibuius maidis, Diaphorina spp. such as D. citri; Dias pis spp. such as D.
• cerasi M. nicotianae, M. persicae, M. varians
• Nasonovia ribis-nigri Neotoxoptera formosana
• Neomega/otomus spp Nephotettlx spp.
• Nephotettlx spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens
• Nezara spp. such as N. viridula
• NHaparvata lugens Nysius huttoni, Oeba!us spp.
• P. devastatrix Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopuivi- naria pyriformis, Psa/lus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudo coccus spp. such as P. comstocki; Psylla spp. such as P.
• Pteromalus spp. PuMnaria amygda/i, Pyri/la spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastro- coccus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascaloni cus, Rhopa!osiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R.
• T. accerra, T perditor such as T. accerra, T perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Triaieurodes spp. such as T. abutiionea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhiocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifoiii, Insects from the order Hymenoptera for example Acanthomyops interjectus, Athaiia rosae, Atta spp. such as A. capiguara, A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens,
• testudinea iridomyrmex humiiis, Lasius spp. such as L. niger, Linepithema humiie, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nyiandria fuiva, Pachycondyia chinensis, Paratre- china longicornis, Para vespula s p p . , such as P. germanica, P. pennsy!vanica, P. vulgaris; Phei- doie spp. such as P. megacephaia; Pogonomyrmex s p p .
• Insects from the order Orthoptera for example Acheta domesticus, Caiiiptamus itaiicus, Chor- toicetes terminifera, Ceuthophi/us spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryiiotaipa spp. such as G. africana, G. gryiiotaipa; Gryiius spp., Hierogiyphus daganensis, Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardaiina; Meianopius spp. such as M. bivittatus, M.
• Boophiius spp. such as B. annuiatus, B. decoioratus, B. mi- cropius, Dermacentor spp. such as D.siivarum, D. andersoni, D. variabiiis, Hyaiomma spp. such as H. truncatum, ixodes spp. such as i. ricinus, i. rubicundus, i. scapuiaris, i. hoiocycius, i.
• pacificus Rhipicephaius sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gaiiinae, Psoroptes spp. such as P. ovis, Rhipicephaius spp. such as R. sanguineus, R. appendicuiatus, Rhipicephaius evertsi, Rhizogiyphus spp., Sarcoptes spp. such asS. Scabiei, and Family Eriophyidae including Aceria spp. such as A.
• Steneotarsonemus spinki Family Tenuipalpidae including Brevi- palpus spp. such as B. Phoenicia, Family Tetranychidae including Eotetranychus spp., Eute- tranychus spp., Oiigonychus spp., Petrobia iatens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseuius, T. teiarius and T. urticae, Bryobia praetiosa, Panonychus spp. such as P. uimi, P.
• O. pratensis O. perseae
• Vasates iycopersici Raoieiia indica, F3 ⁇ 4/??//yCarpoglyphidae including Carpogiyphus spp.
• Penthaieidae spp. such as Haiotydeus destructor, Family Demodicidae with species such as Demodex spp.
• Family Trombicidea including Trombicuia spp.
• Family Macro- nyssidae including Ornothonyss us spp.
• Family Pyemotidae including Pyemotes tritici, Tyropha- gus putrescentiae, Family Acaridae including Acarus sira, Family Araneida including Latrodec- tus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosce/es red us a,
• Pests from the Phylum Nematoda for example, plant parasitic nematodes such as root-knot nematodes, Meioidogyne spp. such as M. hapia, M. incognita, M. javanica; cyst-forming nema todes, Giobodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. gly cines, H. schachtii, H. trifoiii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Apheienchoides spp. such as A.
• plant parasitic nematodes such as root-knot nematodes, Meioidogyne spp. such as M. hapia, M. incognita, M. javanica; cyst-forming nema todes, Giobod
• Awl nematodes Dotichodorus spp.
• Spiral nematodes Hetiocotytenchus mu/ticinctus
• Sheath and sheathoid nematodes Hem- icyctiophora spp. and Hemicriconemoides spp. / Hirshmannietta spp.
• Lance nematodes Hop- toaimus spp.
• False rootknot nematodes Nacobbus spp.
• Needle nematodes Longidorus spp. such as L etongatus
• Lesion nematodes Pratytenchus spp.
• Stunt nematodes Tytencho- rhynchus spp. such as T daytoni, T dubius
• Citrus nematodes Tylenchulus spp.
• T. semipenetrans agger nematodes, Xiphinema s p p .
• a n d other plant parasitic nematode spe cies ;
• Neotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticot/is, Z. nevadensis, Reticu/itermes spp. such as R. hesperus, R. tibialis, R. speratus, R. fiavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natatensis, Insects from the order Blattaria for example Btatta spp.
• B. orientatis such as B. lateralis; Biattei- /aspp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchiora nivea, Periplaneta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuligginosa, P. japonica; Supeiia longipalpa, Parcoblatta pennsyivanica, Eurycotis floridana, Pycnosce/us surinamensis,
• Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. such as C. feiis, C. canis, Xenopsylla cheopis, Puiex irritans, Tricho- dectes canis, Tunga penetrans, and Nosopsy/lus fasciatus,
• Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Thermobia domestica
• Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,
• Pests from the class Diplopoda for example Blaniulus guttulatus, Ju/us spp., Narceus spp.,
• Pests from the class Symphyla for example Scutigerella immacu/ata
• Insects from the order Collembola for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus ase/lus, Porcellio scaber,
• Insects from the order Phthiraptera for example Damaiinia spp., Pediculus spp. such as Pe- diculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and So/enopotes capillatus, Trichodectes spp.,
• Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, for example, Arion spp., Biomphaiaria spp. , Bu/inus spp., Deroceras spp., Gaiba spp., Lymnaea spp., Oncome/ania spp . , Pomacea canaliclata, Succinea spp.
• helminths for example, Ancylostoma duodenaie, Ancyiostoma ceyianicum, Acylostoma brazHiensis, Ancy- lostoma spp., Ascaris lubricoides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., Chabertia spp., C/onorchis spp., Cooperiaspp., DicrocoeHum spp., Dictyocaulus fi/aria, Diphyi- lobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus muitiiocu- iaris, Enterobius vermicu/aris, Facioia spp., Haemonchus spp.
• Haemonchus contortus such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrong ulus spp., Loa Loa, Nematodirus spp., Oesoph- agostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongy!oides stercora /is, Stronyioides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichineiia nativa, Trichineiia britovi, Trichi- neiia neisoni, Trichineiia pseudopsiraiis, Trichostronguius spp., Trichuris trichuria
• resistant pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroas- ca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminife- ra, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum , Diatrea saccharalis, Dichelops furcatus, Dicladisp
• Dilobo- derus abderus such as Dilobo- derus abderus; Edessa spp., Epinotia spp., Formici-dae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Flalotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia orato-rius , Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma-rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocis latipes, Murgantia spp
• Orseolia oryzae such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triacifer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris cas- tanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga inno- tata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp.
• the methods of the invention are particularly applicable to the control of resistant insects (and resistance in insects) of the family Aphididae, such as: Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangu-lae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus heli- chrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Erio- soma lanigerum, Hyalopterus pruni, Li-paphis erysimi, Macrosiphum avenae, Macrosiphum eu- phorbiae, Macrosiphum rosae
• the methods of the invention are particularly applicable for the control of neonicotinoid resistant insects (and the neonicotinoid resistance in such insects) of these families.
• neonicotinoid resistant aphids include Acyrthosiphum pisum, Aphis citrico la, Aphis craccivora, Aphis fabae, Aphis frangulae, Aphis glycines, Aphis gossypii, Aphis na- sturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hy alopterus pruni, Lipaphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae,
• Macrosiphum rosae Myzus cerasi F., Myzus nicotianae, Myzus persicae, Nasonovia ribisnigri, Pemphigus bursarius, Phorodon humuli, Rhopalosiphum insertum Wa, Rhopalosiphum Aidis Fitch, Rhopalosiphum padi L, Schizaphis graminum Rond., Sitobion avenae, Toxoptera au rantii, Toxoptera citricola, and Phylloxera vitifoliae.
• a resistant aphid controlled by the compound of the invention is also resistant to pyrethroid insecticides, such as Lambda-cyhalothrin.
• the in sect may be resistant to neonicotionid insecticide and/or pyrethroid insecticides.
• the method of invention is particularly useful for controlling chewing-biting pests, in particular insects from the order of Lepidoptera and Coleoptera, which method com prises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.
• the method of invention is particularly useful for controlling sucking or pierc ing insects, in particular insects from the order Diptera, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a ste reoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.
• a composition comprising at least one compound of formula (I) in free form or in the form of a ste reoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.
• the insecticide resistant insect is from the order Lepi doptera and is selected from Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatah ' s, Argyresthia conjugella, Autographa gamma , Bupa!us piniarius, Cacoecia murinana, Capua reticu!ana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidenta!is, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiose /- la, Earias insuiana, Elasmopalpus iignose/ius, EupoeciHa ambiguella, Evetria bou/iana, Fe!tia subterranea, Galleria mell
• the insecticide resistant insect is from the order Cole- optera (beetles) and is selected from Agri/us sinuatus, Agriotes iineatus, Agriotes obscurus, Amphimaiius so/stitia/is, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aph- thona euphoridae, Athous haemorrhoidaiis, Atomaria linearis, Biastophagus piniperda, Biitoph- aga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betuiae, Cassida nebuiosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimi/is, Ceuthorrhynchus napi, Chaetocnema tibialis, Con
• the method of invention is particularly useful for controlling the insecticide resistant insect is a potato beetle, more specifically the Colorado potato beetle, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibi tor and the insecticide, towards which insects are resistant, to said resistant insects.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibi tor and the insecticide, towards which insects are resistant, to said resistant insects.
• the insecticide resistant insect is from the order Diptera and is selected from Aedes aegypti, Aedes aibopictus, Aedes vexans, Anastrepha iudens, Anopheles macuiipennis, Anopheles crucians, Anopheles aibimanus, Anopheles gambiae, Anopheles freeborni, Anopheles ieucosphyrus, Anopheles minimus, Anopheles quadrimacuia- tus, Caiiiphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya maceiiaria, Chrysops discalis, Chrysops siiacea, Chrysops atianticus, Cochiiomyia hominivorax, Contarinia sorghicoia Cordyiobia anthropophag
• the method of invention is particularly useful for controlling the insecticide resistant insect is selected from thrips, hoppers and whitefly, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant, to said resistant insects.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant, to said resistant insects.
• the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Spodoptera littoralis, Spodoptera frugiperda, Crocidolomia pavonana, Cnaphalocerus medinalis, Sesamia inferens, Chilo suppressalis, Pyrausta furnacalis, Thermesia gemmatalis, Liriomyza sp., Lep- tinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Meligethes aeneus, Hypera brun- neipennis; Nilaparvata lugens, Nephotettix virens; Acyrthosiphum pisum, Bemisia tabaci, Be- misia argentifolii, Eusch
• the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Chilo suppres salis, Liriomyza sp., Leptinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Franklinella occidentalis, Bemisia tabaci, Bemisia argentifolii, Agrotis ypsilon.
• the insecticide resistant insect is one or more of Agrotis ypsilon, Heliothis virescens, Plutella xylostella, Agriotes lineatus, Dia brotica virgifera, Hypera brunneipennis, Leptinotarsus decemlineata, Phyllotreta striolata.
• the invention relates to a method for controlling or combating non-crop pests, which are resistant to an insecticide, comprising applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta- ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop pests are resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta- ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop pests
• the invention relates to a method for controlling or combating non-crop pests, which are resistant to an insecticide, comprising applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop pests are resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop pests are resistant.
• the invention further relates to the use of compounds of formula (I) as P450 inhibitor for the protection of non-living organic materials against non-crop pests.
• the invention provides the method of controlling resistance to one or more insecticides in non-crop pests, which comprises alternately or simultaneously applying com pound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop pests are resistant, to said non-crop pests or to a crop of useful plants susceptible to and/or under attack from said non crop pests.
• the invention provides the method wherein the resistant non-crop pests developed resistance against insecticides selected from avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, be- ta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acari- cides, insect growth regulators or antifeedants.
• insecticides selected from avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, be- ta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acari- cides, insect growth regulators or
• the invention provides the method for controlling or combating non-crop pests, which are resistant to an insecticide, comprises applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) as cytochrome P450 inhibitor and the insecticide, towards which non crop pests are resistant.
• the non-crop pests which are resistant to an insecticide, are pests of the classes Chilopoda and Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthop- tera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
• the present invention provides a method for controlling or combating following non-crop pests, which are resistant to an insecticide:
• centipedes Chilopoda
• Scutigera coleoptrata centipedes
• spiders e.g. Latrodectus mactans, and Loxosceles reclusa
• scabies e.g. sarcoptes sp
• ticks and parasitic mites ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocy- clus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor vari- abilis, Amblyomma americanum, Ambryomma maculatum, Orni- thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g.
• cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta aus- tralasiae, and Blatta orientalis,
• mosquitoes e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anatrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus,
• Anopheles gambiae Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hom- inis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipe
• Earwigs e.g. forficula auricularia
• Hemiptera true bugs e.g. Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius prolixus, and Arilus critatus,
• Vespula squamosa Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa crabro, Polistes ru- biginosa, Camponotus floridanus, and Li- nepithema humile,
• crickets grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca ameri cana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Callip- tamus italicus, Cho oicetes terminifera, and Locustana pardaliria,
• fleas e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,
• silverfish, firebrat e.g. Lepisma saccharina and Thermobia domestica
• Pediculus humanus capitis e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi- rus pu bis, Haematopinus eurystemus, Haematopinus suis, Linognathus vituli, Bovlcola bovis, Meno- pon gallinae, Menacanthus stramineus and Solenopotes capillatus.
• the hydrazine derivatives of formula (I) which can be used according to the invention are known from and can be prepared according to preparation methods described or referenced in EP-A 604 798. This document relates to plant protection in the agricultural field and discloses the insecticidal and acaricidal activity of compounds of fomula I and other compounds against crop pests of the Coleoptera, Lepidoptera and Acarina orders.
• the invention provides the method of controlling non-crop pests, which are resistant to an insecticide, wherein non-crop pests are pests of the classes Chilopoda and Dilopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hy- menoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
• non-crop pests are pests of the classes Chilopoda and Dilopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hy- menoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.
• the invention provides a method, which process comprises treating the non-crop insect, which are resistant to an insecticide, the plant, or the plant propagation materi al selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against non-crop pest attack, the stored materials or harvest, or alternately, the locus or soil or soil sub stituents or surfaces therefrom, with an effective amount of at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tau tomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.
• an insecticide the plant, or the plant propagation materi al selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and
• in yet another embodiment of the present invention relates to a method of controlling resistance to one or more insecticides in non-crop pests, wherein the resistant non-crop pests developed resistance against against following insecticides:
• M.1 Acetylcholine esterase (AChE) inhibitors M .1 A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxam-yl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
• GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
• M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
• M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
• M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
• M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;
• M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
• M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;
• M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
• M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
• chlorfenapyr DNOC, or sulfluramid
• Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
• M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
• Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide; M.19 Octopamin receptor agonists, e.g. amitraz;
• M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M .20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
• M.21 Mitochondrial complex I electron transport inhibitors e.g. M .21A METI acaricides and in- sec-ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;
• M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-'ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-'methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.
• M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
• Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
• M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
• M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
• M.28.3 cyclaniliprole
• M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-ylJcarbonyl ⁇ aminoJbenzoyll-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-Oarbamoyll-phenyll ⁇ -iS-chloro ⁇ -pyridy -S-itri
• M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
• M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- noTnethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,
• M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
• M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
• M.UN.8 fluazaindolizine
• M .UN.9.a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide
• M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)- , ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S- ⁇ -iodo ⁇ -ll ⁇ -tetrafluoro-l-itrifluoromethy -'ethyll-e-
• M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ⁇ -tetrafluoro-l-Ctrifluoromethy ethyllphenyllcarbamoylJ-'phenyll ⁇ -methyl- benzamide; M.UN.
• M. UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;
• M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16c)
• M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
• M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M.UN.16 ⁇ 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
• M .U N .16h N-methyl-1 -(2-fluoro-1 -methyl
• M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
• M. UN.18b N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
• M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 , 1 ,2, 2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
• M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
• M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
• M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456.
• M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839.
• M .4A.2, guadipyr is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO
• M.22B.1 is described in CN 10171577 and M .22B.2 in CN 102126994.
• Spiropidion M.23.1 is known from WO 2014/191271.
• M.28.1 and M.28.2 are known from W02007/101540.
• M.28.3 is described in W02005/077934.
• M.28.4 is described in W02007/043677.
• M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO
• M.28.5i is described in WO2011/085575, M.28.5j) in W02008/134969, M.28.5k) in US2011/046186 and M .28.5I) in WO2012/034403.
• M.28.6 can be found in WO2012/034472.
• M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911.
• M .UN.5 is de- scrhbed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672.
• M.U N.8 is known from WO2013/055584.
• M.UN.9.a is described in WO2013/050317.
• M.UN.9.b is described in WO2014/126208.
• M. UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO
• M.UN.12.a) to M.UN.12.C) are known from WO2010/006713
• M .UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO 2010/129497 .
• M. UN.14a) and M. UN.14b) are known from W02007/101369.
• M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497.
• M.UN.17a) to M.UN.17 ) are described in WO2015/038503.
• M.UN.18a) to M.UN.18d) are described in US2014/0213448.
• M.UN.19 is de-scribed in WO2014/036056.
• M. UN.20 is known from WO2014/090918.
• M.UN.21 is known from EP2910126.
• M. UN.22a and M. UN.22b are known from WO2015/059039 and W02015/190316.
• M.UN.23a and M.UN.23b are known from WO2013/050302.
• M .UN .24a and M. UN.24b are known from WO2012/126766.
• Acynonapyr M.U N.25 is known from WO
• Benzpyrimoxan M.UN.26 is known from W02016/104516.
• M.UN.27 is known from WO2016174049.
• the non-crop pest which are resistant to insecticide, is selected from flies, mosquitoes (Diptera).
• the invention relates to the method of controlling resistance to one or more insecticides in non-crop pests, which comprises applying compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which the non-crop pests are resistant, to said non-crop pests pref erably selected from flies and mosquitoes.
• compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which the non-crop pests are resistant, to said non-crop pests pref erably selected from flies and
• the non-crop pest is selected from: Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculi- pennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadhmaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex
• the non-crop pest, which are resistant to insecticide is selected from termites (Isoptera). More pref erably, the non-crop pest, which are resistant to insecticide, is selected from: Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus.
• the invention relates to a method for controlling resistance in non-crop pest, which are resistant to insecticide, is selected from termites, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.
• the non-crop pest, which are resistant to insecticide is selected from ants (Hymenoptera). More preferably, the non-crop pest, which are resistant to insecticide, is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis gemi- nata, Sole- nopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Po- go-nomyrmex californicus, Dasymutilla occidentalis, Bombus spp.
• ants Hymenoptera
• the non-crop pest, which are resistant to insecticide is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis gemi- nata, Sole- nopsis invicta
• Vespula squamosa Para- vespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula macu- lata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile.
• the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from ants, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.
• the non-crop pest which are resistant to insecticide, is selected from crickets, grasshoppers, lo custs (Orthoptera). More preferably, the non-crop pest, which are resistant to insectide, is se lected from: Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivitta- tus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca ame-ricana, Schistocerca gregaria, Doci- ostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera
• the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from crickets, grasshoppers, locusts (Orthop- tera), which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, to wards which insects are resistant.
• the invention relates to the method according to the inven tion, wherein the non-crop pest is selected from flies, mosquitoes (Diptera).
• Netting or textile material impregnated with a compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, to wards which insects are resistant, as defined herein.
• Method according to the invention wherein stored products are protected from pests, especially a method according to the inven tion, wherein the stored product is selected from tobacco, nuts, cocoa, fruits, wood.
• a compound of formula (I) in free form or in the form of a stereoisomer an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, as defined herein, or a composition comprising said compound of formula (I) ,
• the compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an iso topic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, and compo sitions comprising them are used for the protection of non-living organic materials, including but are not limited to house-hold goods such as fats, oils, mono- oligo- or polyorganosaccharides, proteins, or fresh or decaying fruits; cellulose-containing materials e.g. wooden materials such as houses, trees, board fences, or sleepers and also paper; and also construction materials, furniture, leathers, animal, plant and synthetic fibers, vinyl articles, electric wires and cables as well as styrene foams.
• house-hold goods such as fats, oils, mono- oligo- or polyorganosaccharides, proteins, or fresh or decaying fruits
• cellulose-containing materials e.g. wooden materials such
• the invention relates to use of compounds of formula (I) according to the inven tion, for the protection of human beings and animals against mosquitos.
• the in vention especially relates to textile materials, foils or nettings which comprise or incorporate a compound according to the invention in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which mosquitos are re sistant.
• "incorporated” means embedded.
• "incorporated” means comprised in impregnated form.
• the invention also relates to above-mentioned textile material for the protection of plants or crops, e.g. tobacco, nuts, fruits, trees, wood.
• the foils or nettings can also be used as mulch foil in the protection of crops.
• the invention relates to a netting, which comprises use of compound of formula I in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor.
• the invention relates to a method for protecting humans from insects, which are resistant to insecticides, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop insects are resistant.
• the invention relates to a method for protecting stored goods from non-crop insects, which are resistant to insecticide, whichmethod comprises applying the compound of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.
• the invention relates to a method for protecting stored goods which are selected from tobacco, nuts, cocoa, fruits, wood; which method comprises applying a compound of for mula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.
• a compound of for mula (I) in the free form or in the form of a stereoisomer an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.
• the present invention also relates to a method for the protection of non-living organic materials against non-crop pests, which are resistant to insecticides, preferably against non-crop pests selected from the group consisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, and Thysanura, com prising contacting the pests or their food supply, habitat, breeding grounds, their locus or the non-living organic materials themselves with at least one compound of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in the free form or in
• compounds of formula (I) in the free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an iso topic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the in secticide, towards which non-crop insects are resistant, are preferably used for protecting cellu lose-containing non-living organic materials:
• compounds of formula (I) in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop insects are resistant, are used for protecting cellulose-containing non-living organic materials against resistant non-crop pests from the Isoptera, Diptera, Blattaria (Blattodea), Hy- menoptera, and Orthoptera orders, most preferably the Isoptera orders
• the present invention also provides a method for protecting cellulose-containing non-living or ganic materials against non-crop pests, which are resistant to insecticides, preferably from the Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the cellulose containing non-living organic materials themselves with at least one of a compound of formula (I) in free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt
• use of compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, or a composition comprising it are used for protecting mono- oligo- or polysaccharides and proteins.
• compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof, or a composition comprising it, as p450 inhibitors, for protecting mono- oligo- or polysaccharides and proteins against non-crop pests selected from the Dermap- tera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blattodea), and Hymenoptra orders.
• the present invention also provides a method for protecting mono- oligo- or polysaccharides and proteins against non-crop pests, which are resistant to insecticides, pref erably selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hyme- noptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blat todea), and Hymenoptra orders, comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with at least one compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecti cide, towards which non-crop insects are resistant , or a composition comprising at least
• compounds of formula (I) in free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecti cide, towards which non-crop insects are resistant, are preferably used for protection of animals against non-crop pest, which are resistant towards insecticides, of the class Chilopoda, and of the orders Araneida, Hemiptera, Diptera, Phthirap
• compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant are used for protection of animals against resistant non-crop pest of the Diptera, Phthiraptera, Siphonaptera, and Parasitiformes orders.
• Animals include warm-blooded animals, including humans and fish.
• Compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor are preferably used for protection of warm-blooded animals such as cattle, sheep, swine, cam els, deer, horses, poultry, rabbits, goats, dogs and cats.
• the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I) of the present invention or a mixture thereof.
• the compounds of formula (I) of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
• agro-chemical compositions e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
• composi-tion types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g.
• compositions types are de fined in the“Catalogue of pesticide formulation types and international coding system”, Tech nical Mono-graph No. 2, 6th Ed. May 2008, CropLife International.
• compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
• auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive col loids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
• suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive col loids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants
• Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-'hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
• mineral oil frac tions of medium to high boiling point e.g. kerosene, diesel oil
• oils of vegetable or animal origin oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthal
• lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
• Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. am monium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
• mineral earths e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
• polysaccharide powders e.g. cellulose, star
• Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
• Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof.
• sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates.
• sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox ylated alcohols, or of fatty acid esters.
• phosphates are phosphate esters. Exam- pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth oxy I ates.
• Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
• alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
• Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
• Exam ples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
• esters are fatty acid esters, glycerol esters or monoglycerides.
• sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides.
• polymeric surfactants are homo- or copolymers of vinyl pyrrol i- done, vinylalcohols, or vinylacetate.
• Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
• Suitable amphoteric surfactants are alkylbetains and imidazolines.
• Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
• Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.
• Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target.
• examples are surfactants, mineral or vegetable oils, and other auxi- laries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
• Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorgan-ic clays (organically modified or unmodified), polycarboxylates, and silicates.
• Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
• Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
• Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
• Suitable colorants are pigments of low water solubility and water- soluble dyes.
• examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
• Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, pol yacrylates, biological or synthetic waxes, and cellulose ethers.
• the present invention relates to the agrochemical compositions comprising at least one P450 inhibitor compound of formula (I) may be combined/mixed with the pre prepared formulation of an active ingredient, for example, insecticide.
• the present invention relates to the agrochemical compositions comprising at least one com pound of formula (I) as P450 inhibitor and pre-prepared formulation of at least one insecticide.
• the present invention provides the agrochemical compositions comprising at least one compound of formula (I) as P450 inhibitor and at least one active ingredient, for example, insecticide.
• oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi ately prior to use (tank mix).
• pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
• These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10: 1 .
• composition types and their preparation are:
• a compound of formula (I) and 5-15 wt% wetting agent e.g. alcohol alkoxylates
• a water-soluble solvent e.g. alcohols
• a compound of formula (I) and 1-10 wt% dispersant e. g. polyvi-nylpyrrolidone
• a compound of formula (I) and 1-10 wt% dispersant e. g. polyvi-nylpyrrolidone
• organic solvent e.g. cyclohexanone
• emulsifiers e.g. calcium dodecylben- zenesulfonate and castor oil ethoxylate
• water-insoluble organic solvent e.g. aromatic hydrocarbon
• Emulsions (EW, EO, ES)
• a compound of formula (I) and 1-10 wt% emulsifiers e.g. calcium dodecylbenzene- sulfonate and castor oil ethoxylate
• emulsifiers e.g. calcium dodecylbenzene- sulfonate and castor oil ethoxylate
• 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon.
• This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
• a compound of formula (I) 20-60 wt% of a compound of formula (I) are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substances.
• dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
• 0,1-2 wt% thickener e.g. xanthan gum
• up to 100 wt% water 100 wt% water
• Dilution with water gives a stable suspension of the active substances.
• binder e.g. polyvinylalcohol
• wt% of a compound of formula (I) are ground finely with addition of up to 100 wt% disper sants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substances.
• disper sants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
• wt% of a compound of formula (I) are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solu tion of the active substances.
• dispersants e.g. sodium lignosulfonate
• wetting agents e.g. alcohol ethoxylate
• solid carrier e.g. silica gel
• a compound of formula (I) In an agitated ball mill, 5-25 wt% of a compound of formula (I) are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub stance. Dilution with water gives a stable suspension of the active substances.
• dispersants e.g. sodium lignosulfonate
• 1-5 wt% thickener e.g. car- boxymethylcellulose
• wt% of a compound of formula (I) are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alko-hol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
• organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
• surfactant blend e.g. alko-hol ethoxylate and arylphenol ethoxylate
• An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% water insoluble or ganic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacry late, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protec tive colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
• a protec tive colloid e.g. polyvinyl alcohol
• an oil phase comprising 5- 50 wt% of a compound of formula (I) and optionally active compound selected from insecticide, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate mon omer (e.g. diphenylme-thene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
• a polyamine e.g. hexamethylenedia- mine
• the monomers amount to 1 -10 wt%.
• the wt% relate to the total CS composition.
• Dustable powders (DP, DS)
• 1-10 wt% of a compound of formula (I) are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
• 0.5-30 wt% of a compound of formula (I) is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
• solid carrier e.g. silicate
• a compound of formula (I) 1-50 wt% are dissolved in up to 100 wt% organic solvent, e.g. ar omatic hydrocarbon.
• organic solvent e.g. ar omatic hydrocarbon.
• compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col orants.
• auxiliaries such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col orants.
• the agrochemical compositions generally comprise between 0.01 and 95%, preferably be tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substances.
• the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
• the user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
• the agrochemi cal composition is made up with water, buffer, and/or further auxiliaries to the desired applica tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
• 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
• composition according to the in vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
• either individual components of the composition according to the in vention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
• either individual components of the composition according to the in vention or partially premixed components e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
• the application of the the compounds of formula (I) of the present invention, or an acceptable salt, an isotopic form, a derivative or mix ture thereof, is preferably as explained in the following.
• the animal pest also referred to as "invertebrate pest"
• insect pest i.e. the insects, arachnids and nema todes
• contacting includes both direct con tact (applying the compounds/compositions directly on the animal pest and indirect contact (ap plying the compounds/compositions to the locus of the animal pest).
• the compounds of the present invention are employed in form of compositions by treating the insects’ surfaces, materials or rooms to be protected from insecticidal attack with an insecticidal- ly effective amount of the insecticide towards which insects are resistant.
• the application can be carried out both before and after the infection of the surfaces, materials or rooms by the insects.
• the present invention also includes a method of combating or controlling animal pests which comprises contacting the animal pests, which are resistant towards insecticides, their habitat, breeding ground, food supply, area, material or environment in which the animal pests are growing or may grow, or the materials, surfaces or spaces to be protected from animal attack or infestation with at least one compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which animal pests are resistant.
• animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with an effective amount of compounds of formula (I) or an ac ceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecti cide, towards which target pests are resistant.
• the application may be carried out be fore or after the infection of the locus by the pest.
• the compounds of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant, can also be applied preventively to places at which occurrence of the resistant pests are expected.
• “Locus” means a habitat, breeding ground, area, material or environment in which a pest or parasite is growing or may grow.
• the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
• Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compounds per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .
• compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an iso topic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant.
• the compounds of formula (I) are effective through both contact (via glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).
• compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant are preferably used in a bait composition.
• the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
• Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks.
• Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources.
• Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.
• the bait employed in the composition is a product, which is sufficiently attractive to incite in sects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it.
• the attractiveness can be manipulated by using feeding stimulants or sex pheromones.
• Food stimu'ants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey.
• Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.
• Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.
• the typical content of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant is from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5%.
• At least one compound of formula (I) in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof, are present in the formulation form of an aerosol.
• insecti cide such as flies, fleas, ticks, mosquitos or cockroaches.
• Aerosol recipes are preferably com posed of the active compounds, solvents such as lower alcohols (e.g. methanol, ethanol, pro panol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
• solvents such as lower alcohols (e.g. methanol, ethanol, pro panol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g.
• ker osenes having boiling ranges of approximately 50 to 250°C, dimethylformamide, N- methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propel'ants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.
• emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7
• the oil spray formulations differ from the aerosol recipes in that no propellants are used.
• the content of active ingredients is from 0.001 to 80 weights %, pref erably from 0.01 to 50 weight% and most preferably from 0.01 to 15 weight %.
• the compounds of formula (I) and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems.
• the methods to control infectious diseases transmitted by insects e.g.
• compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant , op tionally a repellent and at least one binder.
• Suitable repellents for example are N, N-Diethyl- meta-toluamide (DEET), N.Ndiethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2- methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-l ,3-hexandiol, inda- lone, Methylneodecanamide (M N DA), a pyrethroid not used for insect control such as ⁇ (+/-)-3- allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent de rived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (-)-1 -epi- eucamalol or crude plant extract
• Suitable binders are selected for example from polymers and copolymers of vinyl esters of ali phatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di- ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadi ene.
• vinyl esters of ali phatic acids such as such as vinyl acetate and vinyl versatate
• acrylic and methacrylic esters of alcohols such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate
• mono- and di- ethylenically unsaturated hydrocarbons such as styrene
• aliphatic diens such as butadi ene.
• the impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.
• the compounds of formula (I) and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, which are resistant to insecticide, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).
• the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.
• a method of controlling undesired vegeta tion which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is resistant.
• a composition comprising at least one compound of formula (I) in free form or the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is resistant.
• a method of controlling undesired vegeta tion which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.
• the present invention provides a method of controlling undesired vegeta tion, which are resistant to an herbicide, which method comprises applying to undesired vegeta tion, which are resistant to an herbicide, a composition comprising at least one compound of formula (I) as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is resistant.
• a method of controlling undesired vegeta tion which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.
• a method of protecting a crop of useful plants susceptible to and/or under attack by undesired vegetation, which are resistant to a herb icide comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said undesired vegetation, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vege tation is resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or
• a method of controlling resistance to one or more herbicides in undesired vegetation which comprises alternately or simultaneously ap plying compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the herbicide, towards which the undesired vegetation are resistant, to said undesired vegetation or to a crop of useful plants susceptible to and/or under attack from said undesired vegetation.
• a method of controlling undesired vegeta tion which are resistant to a herbicide, which method comprises treating the undesired vegeta tion, the plant, or the plant propagation material selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seed lings and young plants to be protected against undesired vegetation attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with at least one compound of formula (I) ) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one herbicide, towards which the un desired vegetation are resistant.
• the resistant undesired vegetation developed re sistance against herbicide selected from the following list of herbicides
• ALS inhibitors acetolactate synthase inhibitors
• EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
• DHP inhibitors 7,8-dihydropteroate synthase inhibitors
• VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
• herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MS
• herbicidal compounds B and/or the safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
• the herbicidal compounds B and/or the safeners C as described herein have one or more cen ters of chirality and, as a consequence, are present as enantiomers or diastereomers, it is pos- sible to use both, the pure enantiomers and diastereomers and their mixtures, in the composi tions according to the invention.
• herbicidal compounds B and/or the safeners C as described herein have ionizable func tional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
• the herbicide to which the undesired vegetation are re sistant is from the following list of herbicides:
• ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-eth
• ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thio- bencarb, tiocarbazil, triallate and vernolate;
• sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
• imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
• pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8),
• sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
• compositions comprising at least one imidazolinone herbicide
• inhibitors of the photosystem II e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1 -(5-tert-butyl-1-methyl- pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS
• a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herb icide. Among these, likewise a preferred embodiment of the invention relates to those composi tions comprising at least one nitrile herbicide;
• acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sul
• PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5
• glyphosate glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate);
• bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium;
• compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, com pounds of group K1 , in particular dinitroanilines are preferred;
• chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazoli- nones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, 11.3, 11.4, II.5, II.6, II.7, ll.8 and II.9
• isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;
• VLCFA inhibitors preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors:
• 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8; MCPA and its salts and esters, MCPA-thioethyl, MCPB and
• Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C 4 -alkyl, hydroxy-Ci-C 4 -alkoxy-Ci-C 4 -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisoprop- ylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammoni- um, dodecylammoni
• Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensul- fate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4- alkanoic acids, preferably formate, acetate, propionate and butyrate.
• Herbicidal compounds B and/or safeners C as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, pro- pargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Ci 0 -alkylthio esters.
• amides such as mono- and di-Ci-Ce-alkylamides or arylamides
• esters for example as allyl esters, pro- pargyl esters, Ci-Cio-alkyl esters, alkoxyalky
• Preferred mono- and di-Ci-C 6 - alkylamides are the methyl and the dimethylamides.
• Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
• Preferred alkyl esters are, for example, the methyl, ethyl, pro pyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methyl hexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethyl hexyl) esters.
• Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight- chain or branched Ci-C 4 -alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
• An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
• a method of protecting a crop of useful plants susceptible to and/or under attack by undesired vegetation, which are resistant to a herb icide comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said undesired vegetation, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vege tation is resistant.
• a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or
• the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one inhibitor of the lipid biosynthesis (herbi cide b1 ).
• ACC herbicides acetylCoA carboxylase
• non-ACC herbicides a different mode of action
• the ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
• the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one ALS inhibitor (herbicide b2).
• the herbi- cidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
• These inhibitors belong to the group B of the HRAC classification system.
• compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one inhibitor of photosynthesis (herbicide b3).
• the herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on divert ing the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
• PSII inhibitors are preferred.
• the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one bleacher-herbicide (herbicide b5).
• the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
• PDS inhibitors compounds which inhibit carotenoid biosynthesis by inhibition of phytoene de- saturase
• HPPD inhibitors compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase
• DOXsynthase group F4 of HRAC class
• compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
• the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one mitosis inhibitor (herbicide b9).
• the her bicidal activity of these compounds is based on the disturbance or inhibition of microtubule for- mation or organization, and thus on the inhibition of mitosis.
• These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.
• compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b5 and b9.
• compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2 and b5.
• compositions according to the present invention comprise at least one compound of formula (I) and at least one safener C.
• Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the pre sent compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant.
• the safeners and the at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and/or the herbicides B can be applied simultaneously or in succession.
• Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phos- phorthiolates and N-alkyl-O-phenyl
• the active compounds B of groups b1) to b15) and the active compounds C are known herbi cides and safeners, see, for example, The Compendium of Pesticide Common Names
• Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agricul turally acceptable derivative in the compositions according to the invention.
• suitable salts include those, where the counterion is an agriculturally acceptable cation.
• suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
• a suitable ester are dicamba-methyl and dicamba-butotyl.
• Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium.
• esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D- 3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D- isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
• Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium.
• Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.
• Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
• Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
• a suitable salt of MCPB is MCPB sodium.
• a suitable ester of MCPB is MCPB-ethyl.
• Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium.
• Example of suitable esters of clopyralid is clopyralid-methyl.
• Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
• Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
• a suitable ester of picloram is picloram-isoctyl.
• a suitable salt of triclopyr is triclopyr-triethylammonium.
• Suitable esters of triclopyr are for ex ample triclopyr-ethyl and triclopyr-butotyl.
• Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
• Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
• Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
• Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).
• a suitable salt of glufosinate is for example glufosinate-ammonium.
• a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
• Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
• Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
• Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
• Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
• a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
• a suitable salt of naptalam is for example naptalam-sodium.
• Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
• a suitable salt of quinclorac is for example quinclorac-dimethylammonium.
• a suitable salt of quinmerac is for example quinmerac-dimethylammonium.
• a suitable salt of imazamox is for example imazamox-ammonium.
• Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
• Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
• a suitable salt of imazaquin is for example imazaquin-ammonium.
• Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
• a suitable salt of topramezone is for example topramezone-sodium.
• the composition comprises as component I at least one, preferably exactly one compound of formula (I), and as component II at least one, preferably exactly one, herbicide B.
• the composition comprises as component I at least one, preferably exactly one compound of formula (I) as cytochrome P450 inhibitor, and as component II at least two, preferably exactly two, herbicides B different from each other.
• compositions comprising one or more, for example 1 , 2 or 3, compounds of the formula (I) and either one or more, for example 1 , 2 or 3, herbicides B or one or more safeners C.
• ternary compositions includes compositions comprising one or more, for example 1 , 2 or 3, compounds of the formula (I), one or more, for example 1 , 2 or 3, herbicides B and one or more, for example 1 , 2 or 3, safeners C.
• the weight ratio of the active compounds kherbicide B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
• the weight ratio of the active compounds l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
• the relative proportions by weight of the components l:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
• the weight ratio of the components l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
• the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
• the weight ratio of the components B:C is generally in the range of from 1
• the relative proportions by weight of the components l:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1
• the weight ratio of the components l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1
• the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from the range of from
• the weight ratio of compo nents I + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
• herbicides B are the herbicides B as defined above; in particular the herb icides B.1 - B.202 listed below in table B:
• the safeners C which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
• compositions 1.1 to 1.3671 comprising the at least compound of for mula (I) as P450 inhibitor and the substance(s) as defined in the respective row of table 1 :
• Table 1 compositions 1.1 to 1.3671 :
• weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
• compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
• compositions according to the invention control vegetation on non-crop areas very efficient ly, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
• compositions according to the invention are applied to the plants mainly by spraying the leaves.
• the application can be carried out using, for example, water as carrier by custom ary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha).
• the herbicidal compositions may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.
• herbicidal compositions according to the present invention can be done be fore, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
• the herbicidal compositions according to the present invention can be applied pre- or post emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds (I) as P450 inhibitor and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
• the composition according to the invention can be applied by treating seed.
• the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom.
• the herbicidal compositions can be applied diluted or undiluted.
• seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
• seed describes corns and seeds.
• the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
• Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
• the compound of formula (I) and B and, if appropriate, C without formulation auxiliaries are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
• the application rate of the compound of formula (I) as P450 inhibitor and B and, if appropriate, C is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
• the rates of application of the compound of formula (I) according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
• the application rates of the compound of for mula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
• the application rate of the compound of for mula (I) is 0.1 to 1000 g/ha, preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.
• the required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
• the required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
• amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant prop agation material (preferably seeds) are generally required.
• the amounts of active substances applied i.e. compound of formula (I) and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
• the amount of the compound of formula (I) as P450 inhibitor applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the compound of formula (l)per cubic meter of treated material. In the methods of the present invention it is immaterial whether the compound of formula (I) as P450 inhibitor, and the further herbicide component B and/or the herbicide safener compound C are formulated and applied jointly or separately.
• the compound of formula (I) as P450 inhibitor and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.
• compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants.
• suitable crops are the following:
• Preferred crops are Arachis hypogaea, Beta vulgaris spec altissima, Brassica napus var. na pus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossy pium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum
• Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, pota toes, peanuts or permanent crops.
• compositions according to the invention can also be used in crops which have been modi fied by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
• crops as used herein includes also (crop) plants which have been modified by muta genesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
• Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
• Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
• Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
• one or more genes are integrated into the ge nome of a plant in order to add a trait or improve a trait.
• transgenic plants These integrated genes are also re ferred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
• the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants com prising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been intro prised in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
• Herbicide tolerance has been created by using mutagenesis as well as using genetic engineer ing. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbi cides by conventional methods of mutagenesis and breeding comprise plant varieties commer cially available under the name Clearfield ® . However, most of the herbicide tolerance traits have been created via the use of transgenes.
• ALS acetolactate synthase
• Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbi cides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
• HPPD 4- hydroxyphenylpyruvate dioxygenase
• Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1 -2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1 -2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
• Transgenic corn events comprising herbicide tolerance genes are for example, but not exclud ing others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO- 01981 -5, 676, 678, 680, 33121 , 41 14, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
• Transgenic soybean events comprising herbicide tolerance genes are for example, but not ex cluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
• Transgenic cotton events comprising herbicide tolerance genes are for example, but not exclud ing others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN 1021 1 , BXN 10215, BXN 10222, BXN 10224, MON1445, MON 1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
• Transgenic canola events comprising herbicide tolerance genes are for example, but not ex cluding others, MON88302, HCR-1 , HCN 10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.
• Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro teins to plants.
• Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1 A, crylAb, cry1Ab-Ac, cryl Ac, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20.
• genes of plant origin have been transferred to other plants.
• In particu lar genes coding for protease inhibitors like CpTI and pinll.
• a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
• An example for such a transgene is dvsnf7.
• Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt1 1 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON8741 1 , MON88017, MON89034, 33121 , 41 14, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.
• Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.
• Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON 15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB1 19 and SGK321.
• Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
• Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1 -A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
• Tolerance to abiotic conditions has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IN D-00410-5. Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide toler ance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi cide tolerance and tolerance to abiotic conditions.
• Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
• detailed information as to the mutagenized or inte grated genes and the respective events are available from websites of the organizations“Inter national Service for the Acquisition of Agri-biotech Applications (ISAAA)”
• compositions according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might in volve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, ear ly or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spec trum or content.
• plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material produc tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
• a modified amount of ingredients or new ingredients specifically to improve raw material produc tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
• compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cot ton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
• crop plants such as cot ton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
• compositions have been found for the desiccation and/or defoliation of plants, provics for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
• compositions according to the invention are suitable in particular for desic cating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soy bean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
• the present invention also relates to a mixture of at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor of the present invention with at least one mixing partner as defined herein after.
• Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
• components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
• Mixing partners can be selected from pesticides, in particular insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
• Preferred mixing component II partners are insecticides, nematicides, herbicides and fungicides.
• the fol lowing list of pesticides (component II) e. g. insecticides, nematicides, herbicides, fungicides and biopesticides
• insecticides, nematicides, herbicides, fungicides and biopesticides in conjunction with which the compounds of formula (I) can be used, is in tended to illustrate the possible combinations but does not limit them:
• Inhibitors of complex III at Q 0 site azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mande- strobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyra- clostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)
• inhibitors of complex II benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), bos- calid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyrox- ad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrazi- flumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), inpyrfluxam (A.3.22), pyrapropoyn
• C14 demethylase inhibitors triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromu- conazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1.6), dinicona- zole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazo
• Deltal 4-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);
• phenylamides or acyl amino acid fungicides benalaxyl (C.1.1 ), benalaxyl-M (C.1.2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);
• nucleic acid synthesis inhibitors hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
• tubulin inhibitors benomyl (D.1.1 ), carbendazim (D.1.2), fuberidazole (D1.3), thia bendazole (D.1.4), thiophanate-methyl (D.1 .5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5- phenyl-pyridazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7), /V-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), /V-ethyl-2-[(3-ethynyl- 8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinol- yl)oxy]
• methionine synthesis inhibitors cyprodinil (E.1.1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);
• blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hy drochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
• MAP / histidine kinase inhibitors fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);
• G protein inhibitors quinoxyfen (F.2.1 );
• Phospholipid biosynthesis inhibitors edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);
• lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
• phospholipid biosynthesis and cell wall deposition dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
• inorganic active substances Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1 .4), copper oxychloride (H.1 .5), basic copper sulfate (H.1.6), sul fur (H.1.7);
• thio- and dithiocarbamates ferbam (H.2.1), mancozeb (H .2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
• organochlorine compounds anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H .3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1);
• guanidines and others guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 7,5/f[1 ,4]di- thiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2 -/,6/ )-tetraone (H.4.10);
• inhibitors of glucan synthesis validamycin (1.1.1), polyoxin B (1.1.2);
• melanin synthesis inhibitors pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (I.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);
• acibenzolar-S-methyl J.1 .1
• probenazole J.1 .2
• isotianil J.1.3
• tiadinil J.1.4
• prohexa- dione-calcium J.1.5
• phosphonates fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11 ), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-/V-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J .1 .10);
• bronopol K.1.1
• chinomethionat K.1 .2
• cyflufenamid K.1 .3
• cymoxanil K.1.4
• dazomet K.1.5
• debacarb K.1.6
• diclocymet K.1.7
• diclomezine K.1.8
• difenzoquat K.1 .9
• di- fenzoquat-methylsulfate K.1.10
• diphenylamin K.1.1 1
• fenitropan K.1.12
• fenpyrazamine K.1.13
• flumetover K.1.14
• flusulfamide K.1.15)
• flutianil K.1.16)
• harpin K.1 .17
• metha- sulfocarb K.1.18)
• nitrapyrin K.1.19
• nitrothal-isopropyl K.1 .20
• tolprocarb K.1.21
• Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampelomyces quisqua/is, Aspergillus fiavus, Aureobasidium memeiuians, Bacillus aititudi- nis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumi/us, B. simplex,
• catenu- iate also named Giiociadium catenuiatum
• Giiociadium roseum also named Lysobacter antibioticus
• L enzymogenes Metschnikowia fructicoia, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor aibus, Paenibaciiius aivei, Paenibaciiius epiphyticus, P. poiymyxa, Pantoea vagans, Peniciiiium biiaiae, Ph/ebiopsis gigantea, Pseudomonas s p .
• Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity harpin protein, Reynoutria sachaiinensis extract;
• Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israe/ensis, B. t. ssp. gaiieriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beau- veria bassiana, B. brongniartii, Burkhoideria s p p .
• Chromobacterium subtsugae Chromobacterium subtsugae, Cydia pomonei- /a granulovirus (CpGV), Cryptophiebia ieucotreta granulovirus (CrleGV), Fia vobacterium s p p .
• Heiicoverpa armigera nucleopolyhedrovirus HearNPV
• Heiicoverpa zea nucleopolyhedrovirus HzNPV
• Heiicoverpa zea single capsid nucleopolyhedrovirus Heterorhabditis bac- teriophora
• isaria fumosorosea Lecaniciiiium iongisporum, L.
• Microbial pesticides with plant stress reducing, plant growth regulator, plant growth pro moting and/or yield enhancing activity Azospirillum amazonense, A. brasiiense, A. iipoferum, A. irakense, A. haiopraeferens, Bradyrhizobium s pp . , B. eikanii, B. japonicum, B. iiaoningense, B. lupin i, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium iegumi- nosarum bv. phaseoii, R. i. bv. trifoiii, R. i. bv. viciae, R. tropici, Sinorhizobium meiiioti,
• M.1 Acetylcholine esterase (AChE) inhibitors M .1 A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
• methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;
• GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
• M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
• M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
• M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
• M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M .8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;
• M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
• M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;
• M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
• M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
• chlorfenapyr DNOC, or sulfluramid
• Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
• M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
• Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
• Octopamin receptor agonists e.g. amitraz
• M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate
• M.21 Mitochondrial complex I electron transport inhibitors e.g. M .21A METI acaricides and in- sec-ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;
• M.22 Voltage-dependent sodium channel blockers e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-'ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]- , methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat;
• M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
• Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
• M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
• M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
• M.28.3 cyclaniliprole
• M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonyl ⁇ aminoJbenzoylJ-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-'carbamoylJ-phenylJ ⁇ S-chloro ⁇ -pyridy -S-i
• M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
• M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,
• M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
• M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
• M.UN.8 fluazaindolizine
• M.UN.9.a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide
• M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ⁇ -tetrafluoro-Htrifluoromethyl ⁇ ethyll-O- (trifluoromethyl)phenyl]annino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)-ethyl]-6-
• M.UN.1 1.m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.U N.1 1.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ⁇ -tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoyll-'phenyll ⁇ -methyl- benzamide; M.UN.
• M. UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol;
• M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16c)
• M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
• M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M.UN.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
• M .U N .16h N-methyl-1 -(2-fluoro-1 -methyl
• M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
• M .U N .18b N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
• M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
• M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
• M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
• Lipid biosynthesis inhibitors alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-
• b.2 ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazo- sulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, ortho
• protoporphyrinogen-IX oxidase inhibitors acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-sodium,
• b.5 Bleacher herbicides beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
• EPSP synthase inhibitors glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);
• Glutamine synthase inhibitors bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
• Mitosis inhibitors benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pen- dimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlor- thal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flam- prop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham; b.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethen- amid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenyl
• b.1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (175899-01-1 ); b.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
• b.13 Auxinic herbicides 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its
• abscisic acid (0.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, /V-6-benzyladenine, paclobutrazol, prohexadione, prohexadio- ne-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorot
• component II The active substances referred to as component II, their preparation and their activity e. g. against harmful insects and/or undesired vegetation and/or fungi are known (cf.:
• WO 12/84812 CN 1907024, WO 09094442, WO 14/60177, WO 13/116251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511 , WO 1 1/081 174, WO 13/47441 ).
• Some compounds are identified by their CAS Registry Number which is sepa rated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.
• the present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component II) and/or select ed from groups M.1 to M.29.
• agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component II) and/or select ed from groups M.1 to M.29.
• the compounds of formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one further active substance simultaneously, e.g. se lected from groups M .1. to M.29, can be applied either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s).
• the order of application is not essential for working of the present invention.
• the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible rang ing from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In case of a mix ture comprising a component II selected from group L), it is preferred that the pesticide II is ap plied as last treatment.
• the present invention provides an agricultural mixture comprising at least one compound of formula (I), and
• M.1 Acetylcholine esterase (AChE) inhibitors M.1A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
• methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;
• GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
• M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
• M.4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine
• M.4A.2 (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide
• M4.A.3 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezo
• M.7 Juvenile hormone mimics such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;
• M.8 miscellaneous non-specific (multi-site) inhibitors e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;
• M.9 Chordotonal organ TRPV channel modulators e.g. M.9B pymetrozine; pyrifluquinazon;
• M.10 Mite growth inhibitors e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;
• M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;
• M.12 Inhibitors of mitochondrial ATP synthase e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;
• chlorfenapyr DNOC, or sulfluramid
• Nicotinic acetylcholine receptor (nAChR) channel blockers e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;
• M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;
• M.16 Inhibitors of the chitin biosynthesis type 1 e.g. buprofezin;
• Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;
• Octopamin receptor agonists e.g. amitraz
• M.20 Mitochondrial complex III electron transport inhibitors e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;
• M.21 Mitochondrial complex I electron transport inhibitors e.g. M.21A METI acaricides and in secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone; M.22 Voltage-dependent sodium channel blockers, e.g.
• M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]- , ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]- , methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion
• M.24 Mitochondrial complex IV electron transport inhibitors e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;
• Mitochondrial complex II electron transport inhibitors such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;
• M.28 Ryanodine receptor-modulators from the class of diamides e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
• M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
• M.28.3 cyclaniliprole
• M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl ⁇ - , amino)benzoyl]-1 ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-'carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5
• M.29 Chordotonal organ Modulators - undefined target site, e.g. flonicamid;
• M.UN. insecticidal active compounds of unknown or uncertain mode of action e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,
• M.UN.4 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one
• M.UN.5 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);
• M.UN.6 flupyrimin
• M.UN.8 fluazaindolizine
• M .UN.9.a) 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide
• M.UN.10 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;
• M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)- , ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S- ⁇ -iodo ⁇ -ll ⁇ -tetrafluoro-l-itrifluoromethy -ethyll-O-
• M.UN.1 1.m N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ⁇ -tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoy ⁇ phenyll ⁇ -methyl- benzamide; M.UN.1 1.p)
• UN.14a 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;
• M. UN.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxannide; M. UN.16c)
• M.UN.16d 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
• M.UN.16e N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M.UN.16 ⁇ 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
• M .UN.16g 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide
• M .U N .16h N-methyl-1 -(2-fluoro-1 -methyl
• M. UN.17a N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.17b N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide
• M. UN.18a N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide
• M. UN.18b N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide
• M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 , 1 ,2, 2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ;
• M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;
• M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M.
• M.1 Acetylcholine esterase (AChE) inhibitors M .1 A carbamates, e.g. aldicarb, alanycarb, ben- diocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g.
• methamidophos methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos,prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;
• GABA-gated chloride channel antagonists M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;
• M.3 Sodium channel modulators from the class of M.3A pyrethroids e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofen
• M.4 Nicotinic acetylcholine receptor agonists M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine
• Nicotinic acetylcholine receptor allosteric activators spinosyns, e.g. spinosad or spinetoram; M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 - ⁇ 2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1-methyl-2-methylsulfonylethyl)phthalamid,
• M .28.2 (S)-3-Chloro-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl ⁇ -N2-(1 - methyl-2-methylsulfonylethyl)phthalamid
• M.28.3 cyclaniliprole
• M.28.4 methyl-2-[3,5- dibromo-2-( ⁇ [3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonylJ-'aminoJbenzoyll-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5
• the present invention relates to use of agricultural mixture comprising compound of formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and at least one pesticidal compound selected from group M for controlling or combating insects and/or non-crop pests.
• the present invention provides an agricultural mixture comprising at least one compound of formula (I), and
• ALS inhibitors acetolactate synthase inhibitors
• EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
• DHP inhibitors 7,8-dihydropteroate synthase inhibitors
• VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
• herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MS
• the present invention relates to use of agricultural mixture comprising compound of formula (I) and at least one herbicidal compound selected from group b for con trolling or combating undesired vegetation.
• the solid material (dry matter) of the biopesticides (with the excep tion of oils such as Neem oil) are considered as active components (e. g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).
• the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).
• the total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1 x 1010 CFU equals one gram of total weight of the respective active component.
• Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells.
• CFU may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Stei- nernema feltiae.
• the weight ratio of the com ponent I) and the component II) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1.
• the weight ratio of the component I) and the component II) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1.
• the weight ratio of the component I) and the component II) usually is in the range of from 20,000:1 to 1 :10, often in the range of from 10,000:1 to 1 :1 , regularly in the range of from 5,000:1 to 5:1 , preferably in the range of from 5,000:1 to 10:1 , more preferably in the range of from 2,000:1 to 30:1 , even more preferably in the range of from 2,000:1 to 100:1 and in particular in the range of from 1 ,000:1 to 100:1 .
• the weight ratio of the component I) and the component II) usually is in the range of from 10:1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.
• the weight ratio of the component I) and the component II) usually is in the range of from 10:1 to 1 :20,000, often in the range of from 1 :1 to 1 :10,000, regularly in the range of from 1 :5 to 1 :5,000, preferably in the range of from 1 : 10 to 1 :5,000, more preferably in the range of from 1 :30 to 1 :2,000, even more preferably in the range of from 1 :100 to 1 :2,000 to and in particular in the range of from 1 :100 to 1 :1 ,000.
• the weight ratio of component I) and component II) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component I) and component III) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1.
• Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the com ponent I).
• the application rates preferably range from about 1 x 106 to 5 x 1016 (or more) CFU/ha, preferably from about 1 x 108 to about 1 x 1013 CFU/ha, and even more preferably from about 1 x 109 to 5 x 1015 CFU/ha and particularly preferred even more preferably from 1 x 1012 to 5 x 1014 CFU/ha.
• (entomopathogenic) nematodes as microbial pesticides (e. g.
• the application rates preferably range inform about 1 x 105 to 1 x 1012 (or more), more prefera bly from 1 x 108 to 1 x 101 1 , even more preferably from 5 x 108 to 1 x 1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.
• the application rates with respect to plant propagation material preferably range from about 1 x 106 to 1 x 1012 (or more) CFU/seed.
• the concentration is about 1 x 106 to about 1 x 109 CFU/seed.
• the application rates with respect to plant propagation material also preferably range from about 1 x 107 to 1 x 1014 (or more) CFU per 100 kg of seed, preferably from 1 x 109 to about 1 x 1012 CFU per 100 kg of seed.
• the biopesticides from group L1 ) and/or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity.
• the biopesticides from group L3) and/or L4) may also have fun gicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regula tor, plant growth promoting and/or yield enhancing activity.
• the biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.
• CNCM 1-1582 a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009/126473, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01 ; e. g. PRO MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tra- cheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B.
• pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pu milus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B 30087; e. g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B.
• subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Mi crobiol. 27, 372-379, 2004; US 2010/0260735; WO 201 1/109395); B. thurin-giensis ssp. aiza- wai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG 6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Miinsingen, Germany), B. t. ssp.
• israeltaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent BioSci- ences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B- 50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp.
• tenebrionis NB-176-1 a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.L, Italy), B.
• DSM 5480 Tenebrio molitor
• EP 585 215 B1 e. g. Novodor® from Valent BioSciences, Switzerland
• Beauveria bassiana GHA ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA
• B. bassiana JW-1
• bassiana PPRI 5339 isolated from the larva of the tortoise beetle Con- chyloctenia punctata (N RRL 50757; e. g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMI A 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e. g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B.
• japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661 -666, 1990; e. g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 201 1); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol.

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Abstract

Description

NEW CATECHOL MOLECULES AND THEIR USE AS INHIBITORS TO P450 RELATED METABOLIC PATHWAYS

Field of the Invention

The present invention relates to the new catechol molecules and their use as inhibitors to P450 related metabolic pathways. The invention further relates to a method of controlling crop pests and/or non-crop pests that are resistant to one or more insecticide(s) and method of controlling undesired vegetation that are resistant to one or more herbicide(s) by applying at least one in hibitor to P450 related metabolic pathways of formula (I).

Background of the Invention

Resistance

The World Health Organization has defined resistance as“the development of an ability in a strain of insects to tolerate dose of toxicant that would prove lethal to the majority of individuals in a normal population of the same species”. According to the Insecticide Resistance Action Committee (IRAC), resistance may be defined as‘a heritable change in the sensitivity of a pest population that is reflected in the repeated failure of a product to achieve the expected level of control when used according to the label recommendation for that pest species’ (www.irac- online.org). Cross-resistance occurs when resistance to one insecticide confers resistance to another insecticide, even where the insect has not been exposed to the latter product. Clearly, because pest insect populations are usually large in size and they breed quickly, there is always a risk that insecticide resistance may evolve, especially when insecticides are misused or over used. Pesticide resistance and herbicide resistance is therefore to be similarly construed.

The resistant may be partial or complete and it will be appreciated that all degrees of resistance are included the meaning of this term, whether they be very low resistance, low resistance, high resistance, very high resistance or total resistance.

It did not take long after the introduction of synthetic organic pesticides, for example insecticides and herbicides till the first cases of resistance were detected and confirmed. With every new pesticide introduction, cases of resistance appeared after a certain period thereafter in some of key pest species, for example insects and undesired vegetation. This phenomenon has been described as the‘pesticide treadmill’. As a result of continued applications over time the pest evolves resistance to the insecticide and the resistant strain becomes increasingly difficult to control at the labeled rate and frequency. This in turn has often led to more frequent applica tions of the insecticide. The phenomena of intensity of the resistance and the frequency of pes- ticides-resistant individuals in the population are both still increasing and problems of control continue worsen when product is applied. Eventually users may switch to another pesticide if one is available. The genetics of the heritable resistance traits and the intensive repeated appli cation of pesticides and herbicides, together are responsible for the rapid build-up of resistance in most pests and undesired vegetation respectively.

Natural selection by a pesticide allows some naturally occurring, pre-adapted pests with re sistance genes to survive and to pass-on the resistance trait to their offspring. Through contin ued application of pesticides with the same MoA, selection for the resistant individuals persists so the proportion of resistant pests in the population increases, while susceptible individuals are eliminated by the pesticide. Under this permanent selection pressure, resistant pests outnumber susceptible ones and the pesticide is no longer effective. The speed with which resistance de velops depends on several factors, including how fast the pests reproduce/grow, the migration and host range of the pest, the availability of nearby susceptible populations, the persistence and specificity of the crop protection product, and the rate, timing and number of applications made. Resistance increases e.g. in greenhouses, where pests reproduce/grow quickly and when there is little or no immigration of susceptible individuals and the user may spray frequent ly (https://www.irac-online.org/about/resistance/).

There are several mechanisms of resistance development. The most common is metabolic re sistance. The insecticide resistant insects can detoxify by destruction or excretion in comparison to normal non-resistant insects, e.g. due to their metabolism such as their enzyme systems. Metabolic resistance is very often dependent on the structure of the active ingredient. There fore, the metabolic resistance is most likely overcome by actives with a different chemical struc ture. Another resistance mechanism is a modification of the target structure (protein, receptor, ion channel, etc.) of the insecticide. The insecticidal activity is reduced by a change in the bind ing site, e.g. due to point mutations, which are passed on. Further, there is also resistance due to behavioral change and penetration resistance (the outer shell of the insect developed barriers that slow down the penetration of insecticides in the body of the insect). In resistant pests, a combination of several of these resistance mechanisms can be found.

Whether or not a resistance mechanism that is responsible for the resistance of a pest to a par ticular insecticide, these pests also faces a new insecticide resistant making (cross-) resistance, is difficult because of the different resistance mechanisms before-seen. Particularly in cases where the mechanism of action of the new insecticide or is not known, or where the resistance by mechanisms other than by changing the binding site, for example by metabolic resistance is mediated, the prediction of a cross-resistance is difficult. Piperonyl butoxide (PBO) is a com pound that was discovered in the 1950’s as a synergist for pyrethroid type insecticides. PBO acts as an insecticide synergist by inhibiting the natural defense mechanisms of the insect, the most important of which is the mixed-function oxidase system, (MFOs) also known as the cyto chrome P450 system. The MFO system is the primary route of detoxification in insects, and causes the oxidative breakdown of insecticides such as pyrethrins and the synthetic pyre- throids. It’s effect on GST pathway is very limited (Casida, J. E. (1970). MFO involvement in the biochemistry of insecticide synergists. J. Agric. Food Chem. 18, 753-772).

The management of insecticide resistance (Insecticide Resistance Management or IRM) is an important task in agriculture and is recommended as a critical component of integrated pest management (IPM). The most important measure in the context of IRM is to reduce the selec tion pressure for resistant pests. This is achieved by the alternate use of various chemical clas ses of insecticides with different mechanisms of action, whereby the development of resistance can be slowed or prevented entirely.

Insects have several pathways to metabolize exogenous molecules that they are exposed to. These molecular transformations can either activate an insecticide, such is the case of pro drugs. Alternatively, these mechanisms can also confer the insect what is known as metabolic resistance. In this instance, the metabolism of the insect transforms the insecticide molecules in such way they are deactivated and become harmless to the insects and easily excretable.

There are three pathways that represent the majority of the metabolic resistance to insecticides: Esterases, Mix function oxidases, and glutathione S-transferases.

Esterases: Catalyze the hydrolysis of ester-insecticides into their respective acid and alcohol compounds. This process increases the polarity of the compounds making them easier to ex crete. Esterases can also sequester some insecticides in such way that they are not available for interaction with the insect proteins making them non-toxic to the insect. One of the most known examples is the insecticide detoxification by the overproduction of a specific carboxyles- terase in the green peach aphid Myzus persicae (Hemiptera: Aphididae). (Field et al., 1988; Bizzaro et al., 2005; Rivi et al., 2013).

Mix function oxidases: This is a large family of enzymes that participate in the detoxification of xenobiotics and some hormones. They transform lipophilic compounds into polar metabolites than can be easily eliminated. Cytochrome P450 monooxygenases (P450s) belong to this group. The name is derived from their absorbance peak at 450 nm (Soret peak) in their reduced form. Due to the large number of enzymes and their substrate specificity, P450s are able to cat alyze different reactions such as epoxidation, hydroxylation, N-dealkylation, O-dealkylation or desulphurization. For that reason they play an important role in plant-insect interactions, as well as in the metabolism of many insecticide classes, including carbamates, organophosphates, pyrethroids and neonicotinoids (Yu, 2008; Philippou et al., 2010; Puinean, 2010).

Glutathione S-transferases (GST). Insect GSTs are divided into two different groups (microso mal and cytosolic) according to their location within the cell, but only the latter has been impli cated in the metabolism of insecticides. The GST pathway catalyzes the conjugation of the re duced form of glutathione to xenobiotic substrates for the purpose of detoxification and then easy excretion. One of the most known examples is the DDT deactivation by DDT- dehydrochlorinase GST, which also has been reported as being responsible for DDT resistance in houseflies and mosquitoes (Enayati et al., 2005).

Field LM , Devonshire AL, Forde BG. Molecular evidence that insecticide resistance in peach- potato aphids (Myzus persicae Sulz.) results from amplification of an esterase gene. Biochem.

J. 251 : 309-312, 1988.

Bizzaro D, Mazzoni E, Barbolini E, Giannini S, Cassanelli S, Pavesi F, et al. Relationship among expression, amplification and methylation of FE4 esterase genes in Italian populations of Myzus persicae (Sulzer) (Flomoptera: Aphididae). Pest. Bioch. Physiol. 81 : 51 -58, 2005.

Rivi M, Monti V, Mazzoni E, Cassanelli S, Panini M, Anaclerio M, et al. A1-3 chromosomal translocations in Italian populations of the peach potato aphid Myzus persicae (Sulzer) not linked to esterase-based insecticide resistance. Bull. Entomol. Res. 103: 278-285, 2013. Yu SJ. The toxicology and biochemistry of insecticide. CRC Press. Boca Raton, FL, USA, pp XVI+276, 2008.

Puinean AM, Foster SP, Oliphant L, Denholm I, Field LM, Millar NS et al. Amplification of a cy tochrome P450 gene is associated with resistance to neonicotinoid insecticides in the aphid Myzus persicae. PLOS Genet 6:e1000999, 2010.

Enayati AA, Ranson H and Hemingway J (2005) Insect glutathione transferases and in secticide resistance. Insect MolBio 14: 3-8.

US 9,386,767 provides derivatives of Dillapiole having properties to inhibit cytochrome P450 enzymes such as human CYP3A4. It further suggests that these derivatives can be used as synergists for pyrethrin class of pesticides.

It an object of the presently claimed invention to provide new compounds and their uses, meth ods and compositions for controlling these pesticide, both crop and non-crop pests, resistant and herbicide resistant induced diseases in crops.

Description of the Invention

In one embodiement the present invention relates to a compound of formula (I)

Formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof; wherein

R¹ is selected from group consisting of H, halogens, CN, N0₂, SH, S(C₂-Ci₂-alkyl), Ci-Ci₂-alkyl, 0-Ci-C₇-alkyi, C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkenyi, C₂-Ci₂-alkynyl, C=0(OH), C=0(NR¹²R¹³), 0-C₅- Ci₂-alkynyl, , C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C=0(0)C₅-Ci₄- aryl, S(0₂)-C₂-Ci₂-aikyl, S(0)Ci-Ci₂-aikyl, S(0)(CR⁵R⁶)_n-C₅-C₁₄-aryi , (CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)_nC3-Ci₂-cycloalkyl, (CR⁵R⁶)_nCs-Ci₄-heteroaryl and (CR⁵R⁶)_nC3-Ci₂-heterocycloalkyl; whereby halogens are F, Cl and I;

R⁴ is selected from group consisting of H, halogens, CN, N0₂, SH, S(Ci-Ci₂-alkyl), Ci-Ci₂-alkyl, 0-Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, 0-C₂-Ci₂-aikenyl, C₂-Ci₂-alkynyl, C=0(OH), C=0(NR¹²R¹³), O- C₅-Ci₂-alkynyl, C=0(H), C=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C⁼0(0)C₅-Ci₄-aryl, S(0₂)-C₂-Ci₂-aikyl, S(0)Ci-Ci₂-aikyl, S(CR⁵R^®)_n-Cs-Ci₄- aryl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl, S(0₂)(CR⁵R⁶)_n-C₅-Ci₄-aryl, (CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)_nC₃-Ci₂- cycloalkyl, (CR⁵R⁶)_nC5-Ci4-heteroaryl and (CR⁵R⁶)_nC3-Ci2-heterocycloalkyl; whereby halogens are F, Cl and I ;

R² is OR⁷, N0₂, NR⁸R⁹, (CR⁵R⁶)_nC3-Ci2-cycloalkyl whereby C3-Ci₂-cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0₂ or together with R³ forms C3-Ci2-cycloalkyl whereby C3-Ci₂-cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0₂;

R⁷ is selected from group consisting of H, Ci-Ci₂-alkyl, C₂-Ci2-alkenyl, C₂-Ci2-alkynyl, C=0(C₅- Ci4-aryl), (CR⁵R⁶)_nC5-Ci₄-aryl, (CR⁵R⁶)_nC5-Oi4-heteroaryl, (CR⁵R⁶)_nC3-Ci₂-cycloalkyl,

(CR⁵R⁶)_nC5-Ci4-aryl- C3-Ci2-membered heterocycloalkyl, (CR⁵R⁶)_nC5-Ci2-membered heterocy cloalkyl, (CR⁵R⁶)_n-1 ,3-benzodioxolyl and (CR⁵R⁶)_nC5-Ci₄-membered heterocycloalkenyl; where by R⁷ is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12e which are independently selected from the group consisting of F, Cl, Br, I , OH, SH , CN , N0₂, N R¹⁰R¹¹, O-C1-C12-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₄-C₆-alkynyl, Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C2-C12- alkynyl, C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C=0(0)C₅-Ci₄-aryl, C=0(H), C3-Ci2-cycloalkyl, C=0(C₁-Ci₂-aikyl), C=0(OH), C=0(NR¹²R¹³), C3-Ci2-halocycloalkyl, Cs-Ci₄-aryl, Cs-Ci₄-heteroaryl, S(0₂)-Ci-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR⁵R⁶)_n-C5-Ci₄-aryl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl, 1 ,3-benzodioxolyl, (CR⁵R⁶)_n-0-(1 ,3-benzodioxolyl) and

S(0₂)(CR⁵R⁶)n-C₅-Ci₄-aryl;

R⁸ and R⁹, identical or different, are selected from the group consisting of H, OH , N R¹⁰R¹¹,

(C R⁵ R⁶)n C5-C 1₄-ary I , C=0(CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)nCs-Ci₄-heteroaryl, S(0₂)(CR⁵R^®)_n-C₅-Ci₄- aryl, S(0₂)-Ci-Ci₂-alkyl, C=0(Ci-Ci₂-alkyl), Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl,

(CR⁵R⁶)_nC₅-Ci -aryl, (CR⁵R⁶)nC₅-Ci2-membered heterocycloalkyl, (CR⁵R⁶)nC₅-Ci -membered heterocycloalkenyl and (CR⁵R⁶)_nC3-Ci2-cycloalkyl; whereby R⁸ and R⁹ are unsubstituted or fur ther substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12f which are independently se lected from the group consisting of F, Cl, Br, I , OH , SH, CN , N0₂, NR¹⁰R¹¹ , C=0(Ci-Ci₂-alkyl), C=0(OH), C=0(NR¹²R¹³), C=0(H), 0-Ci-Ci₂-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkynyl,

C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryi), C=0(0)C₅-Ci₄-aryi, (CR⁵R⁶)_nC₅- Ci₄-aryl, Cs-Cs-cycloalkyl, (CR⁵R⁶)_nC3-Ci2-heterocycloalkyl, (CR⁵R⁶)_nCs-Ci₄-heteroaryl, Ci-Ci₂- alkyl, C₂-Ci₂-alkenyl and C₂-Ci₂-alkynyl, S(0₂)-Ci-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR⁵R⁶)_n-C₅-Ci₄- aryl, S(0)(CR⁵R⁶)n-Cs-Ci₄-aryl and S(0₂)(CR⁵R⁶)_n-C₅-Ci₄-aryl;

R³ is selected from group consisting of Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl, (CR⁵R⁶)_nC₅- Ci₄-aryl, (CR⁵R⁶)_nCs-Ci4-heteroaryl, (CR⁵R⁶)_nC3-Ci₂-cycloalkyl, (CR⁵R⁶)_nC3-Ci₂-heterocycloalkyl, (CR⁵R⁶)_nC3-Ci2-heterocycloalkenyl and (CR⁵R⁶)_nC3-Ci₂-heterocycloalkynyl; whereby R³ is un substituted or further substituted by 1 , 2, 3 or 4 identical or different groups R¹²a which are inde pendently selected from the group consisting of F, Cl, Br, I , OH , SH, CN , N0₂, NR¹⁰R¹¹ , O-C1- Ci2-alkyl, 0-C₂-Ci₂-alkenyl, 0-Cg-Ci₂-aikynyl, Ci-Ci₂-alkyl, C₂-Ci2-alkenyl, 0(CR⁵R⁶)nC₅-Ci₄-aryl, C₂-Ci₂-alkynyl, C=0(OH), C=0(N R¹²R¹³), C=0(H), OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyi), OC=0(C₃-Ci₂-cycloalkyl), C=0(0)( C3-Ci₂-cycloalkyl), 0C=0(C₂-Ci₂-alkenyl), C=0(0)(C₂-Ci₂- alkenyl), 0C=0(CR⁵R⁶)_nC₅-Ci₄-aryi, C=0(0)(CR⁵R⁶)_nC₅-Ci -aryi, 0C=0(H)(CR⁵R⁶)_n,

C=0(0)(H)(CR⁵R⁶)_n, C₃-C 12-cycloalkyl, C=0(Ci-Ci₂-alkyl), (CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)_nC₅-Ci₄- heteroaryl, S-(CR⁵R⁶)_n-C5-Ci₄-aryl, S(0₂)(CR⁵R⁶)_n(C₅-Ci₄-aryl), OC=0(1 ,3-benzodioxolyl), (CR⁵R⁶)_n-1 ,3-benzodioxolyl ;

R⁵ and R⁶, identical or different, are selected from the group consisting of H, F, Cl, Br, I, OH, CN, SH, N0₂, NR¹⁰R¹¹, 0-Ci-Ci₂-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkynyl, OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyl), OC=0(C₃-Ci₂-cycloalkyl), C=0(0)( C3-Ci₂-cycloalkyl), 0C=0(C₂-Ci₂- alkenyl), C=0(0)(C₂-Ci₂-alkenyl), 0C=0(C₅-Ci₄-aryl), C=0(0)Cs-Ci₄-aryl, C=0(Ci-Ci₂-alkyi), C=0(OH), C=0(NR¹²R¹³), C=0(H), C3-Ci₂-cycloalkyl, C₅-Ci₄-aryl, C3-Ci₂-heterocycloalkyl, C₅- Ci4-heteroaryl, S(0₂)-Ci-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR¹⁴R¹⁵)_n-C₅-Ci₄-aryl, S(0)(CR¹⁴R¹⁵)_n- C5-Ci4-aryl, S(0₂)(CR¹⁴R¹⁵)_n-C₅-Ci₄-aryl, Ci-Ci2-alkyl, C₂-C 12-alkenyl and C2-Ci2-alkynyl;

R¹⁰ and R¹¹, identical or different, are H, C3-Ci2-cycloalkyl, C2-C 12-alkenyl, C2-Ci2-alkynyl or Ci- C12 alkyl or R¹⁰ together with R¹¹ forms C₅-Ci₂-membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or C₅-Ci4-membered heteroaryl;

R¹² and R¹³, identical or different, are H, C3-Ci2-cycloalkyl, C₂-C 12-alkenyl, C₂-Ci₂-alkynyl or Ci- C12 alkyl or R¹² together with R¹³ forms C5-Ci2-membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or Cs-C_M-membered heteroaryl;

R¹⁴ and R¹⁵, identical or different, are H, C3-Ci2-cycloalkyl, C₂-C 12-alkenyl, C2-Ci2-alkynyl or Ci- C12 alkyl; whereby R^12e, R^12f or R¹²a are unsubstituted or further substituted by 1 , 2, 3 or 4 identical or dif ferent groups which are independently selected from the group consisting of F, Cl, Br, I, OH, SH, CN, NO2, NR¹⁰R¹¹, 0-Ci-Ci₂-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-aikynyl, Ci-Ci2-alkyl, C2-C12- alkenyl, C₂-Ci₂-alkynyl, OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyl) and C=0(H); and n is 0, 1 , 2, 3, 4, 5 or 6. with proviso that when R¹ is H, OCH₃, CH₂CH=CH₂; R⁴ is H and R² is OH , OCH₃, OCH₂R wherein R is benzene ring substituted with one or more of F, Cl, Br, CH₃, OCH₃ then R³ is not CH2CH=CH2 or a structure of the following type:

where R^4’ is C1-C6 alkyl, C5-C6 cycloalkyl, C₂-C6 alkenyl. In one embodiment, the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.

Although the present invention will be described with respect to particular embodiments, this description is not to be construed in a limiting sense.

Before describing in detail exemplary embodiments of the present invention, definitions im portant for understanding the present invention are given. As used in this specification and in the appended claims, the singular forms of "a" and "an" also include the respective plurals un less the context clearly dictates otherwise. In the context of the present invention, the terms "about" and "approximately" denote an interval of accuracy that a person skilled in the art will understand to still ensure the technical effect of the feature in guestion. The term typically indi cates a deviation from the indicated numerical value of ±20 %, preferably ±15 %, more prefera bly ±10 %, and even more preferably ±5 %. It is to be understood that the term "comprising" is not limiting. For the purposes of the present invention the term "consisting of' is considered to be a preferred embodiment of the term "comprising of. If hereinafter a group is defined to com prise at least a certain number of embodiments, this is meant to also encompass a group which preferably consists of these embodiments only. Furthermore, the terms "first", "second", "third" or "(a)", "(b)", "(c)", "(d)" etc. and the like in the description and in the claims, are used for distin guishing between similar elements and not necessarily for describing a sequential or chronolog ical order. It is to be understood that the terms so used are interchangeable under appropriate circumstances and that the embodiments of the invention described herein are capable of oper ation in other sequences than described or illustrated herein. In case the terms "first", "second", "third" or "(a)", "(b)", "(c)", "(d)", "i", "ii" etc. relate to steps of a method or use or assay there is no time or time interval coherence between the steps, that is, the steps may be carried out sim ultaneously or there may be time intervals of seconds, minutes, hours, days, weeks, months or even years between such steps, unless otherwise indicated in the application as set forth herein above or below. It is to be understood that this invention is not limited to the particular method ology, protocols, reagents etc. described herein as these may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention that will be limited only by the ap pended claims. Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art.

Unless otherwise indicated, the following definitions are set forth to illustrate and define the meaning and scope of the various terms used to describe the invention herein and the append ed claims. These definitions should not be interpreted in the literal sense as they are not intend ed to be general definitions and are relevant only for this application.

The term "independently" when used in the context of selection of substituents for a variable, it means that where more than one substituent is selected from a number of possible substitu ents, those substituents may be the same or different.

The organic moieties or groups mentioned in the above definitions of the variables are collective terms for individual listings of the individual group members. The term "C_u-C_w" indicates the number of carbon atom possible in each case. The term "Ci-Ci₂-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 12 carbon atoms, for example, methyl, ethyl, propyl, 1-methylethyl, butyl, 1- methylpropyl, 2-methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2- dimethylbutyl, 1 ,3-dim ethyl butyl, 2, 2-dim ethyl butyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methyl propyl .

The term "C₂-Ci2-alkenyr refers to a straight-chain or branched unsaturated hydrocarbon radi cal having 2 to 6 carbon atoms and a double bond in any position. Examples are "C₂-C4-alkenyl" groups, such as ethenyl, 1 -propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3- butenyl, 1 -methyl-1 -propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl. The term "C₂-Ci₂-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C₂-C₄ al- kynyl" groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl, but-1 -ynyl, but-2-ynyl, but-3-ynyl, 1 - methyl-prop-2-ynyl.

The term "C3-Ci₂-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.

The term“Cs-Cn-aryl" refers to monocyclic and polycyclic aromatic radicals, for example C5-C6- aryl radicals, for example phenyl or cyclopenta-1 ,3-diene, or, C«rCi₄-aryl radicals, for example, naphthalene or anthracene.

The term "C₅-Ci₄-heteroaryl" means an aryl group where at least one carbon atom on the hy drocarbon chain normally carrying 5 to 14 carbon atoms is substituted by another atom selected from N, O, oxo or S, for example, pyridyl, pyridinone, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, thienyl, furanyl, pyrrolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, imidazolyl, triazol- yl, thiadiazolyl, oxadiazolyl and tetrazolyl rings. Any monocyclic which has the characteristics of aromaticity in terms of electron distribution throughout the ring system is included in this defini tion.

The term“C5-Ci₄-membered heterocycloalkenyl” refers to 5 to 14 membered monocyclic ring system having one or more heteroatoms, such as O, N, oxo, S as ring members and one or more double bonds. For example, the term”C5-C6-heterocycloalkenyl” refers to a cyclic unsatu rated hydrocarbon residue with 5 or 6 carbon atoms, which comprises at least one double bond, and wherein, one or more C atoms are replaced by heteroatoms independently selected from O, N, oxo or S, for example, (2,3)-dihydrofuranyl, (2,3)-dihydrothienyl, (2,3)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,5)-dihydropyrrolyl, (2,3)-dihydroisoxazolyl, (1 ,4)-dihydropyridin-1-yl, di- hydropyranyl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3- dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3- yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3- yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3- yl, 3,4-dihydrooxazol-4-yl, 4,5-dihydropyrazol-2-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol- 4-yl, 4,5-dihydropyrazol-5-yl, 2,5-dihydrothienyl and (1 ,2,3,4)-tetrahydropyridin-1 -yl. Heterocy- cloalkenyl residues may preferably comprise 1 , 2, or 3 heteroatom(s) mutually independently selected from the group consisting of O, S, oxo and N as ring members.

The term " C₅-Ci4-membered heterocycloalkyl " means a non-aromatic monocyclic or polycyclic ring comprising 5 to 14 carbon atoms and at least one heteroatom selected from O, S, oxo and N. A heterocycloalkyl group can have one or more carbon-carbon double bonds or carbon- heteroatoms double bonds in the ring as long as the ring is not rendered aromatic by their pres ence. Examples of heterocycloalkyl groups include aziridinyl, pyrrolidinyl, pyrrolidino, piperidinyl, piperidino, piperazinyl, piperazino, morpholinyl, morpholino, thiomorpholinyl, thiomorpholino, tetrahydrofuranyl, tetrahydrothiofuranyl, tetrahydropyranyl and pyranyl.

Another embodiment of the present invention relates to the compound of formula (I), wherein R¹ is H or OCH₃ and R⁴ is H, or

R¹ is H or OCH₃ and R⁴ is halogen, or

R¹ is halogen and R⁴ is H, or

R¹ is halogen and R⁴ is halogen;

R² is OR⁷ or N R⁸R⁹, wherein

R⁷ is H, Ci-Ci2-alkyl, (CR⁵R⁶)_nC5-Ci₄-aryl, (CR⁵R⁶)_nC5-Ci₄-heteroaryl or (CR⁵R⁶)_nC₅-Ci₄-aryl- C₃- Ci2-membered heterocycloalkyl;

R⁸ and R⁹, identical or different are selected fromH and (CR⁵R⁶)_nC5-Ci₄-aryl;

whereby R⁷ is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12e which are independently selected from the group consisting of F, Cl, Br, I, 0-Ci-Ci₂-alkyl, Ci-Ci2-alkyl, 1 ,3-benzodioxolyl, C₅-Ci₄-heteroaryl and C=0(0)(Ci-Ci₂-aikyl);

R³ is selected from the group consisting of C1-C 12-alkyl, C2-Ci2-alkenyl, C2-Ci2-alkynyl and C₃- C₁₂-cycloalkyl; whereby R³ is unsubstituted or further substituted by 1 , 2 or 3 identical or differ ent groups R¹²a which are independently selected from the group consisting of F, Cl, Br, I, C2- Ci2-alkenyl, C₂-Ci2-alkynyl, C3-Ci₂-cycloalkyl, C₅-Ci₄-aryl, C₅-Ci₄-heteroaryl, S-(CR⁵R⁶)_n-C₅-Ci₄- aryl and S0₂(CR⁵R⁶)n(C₅-Ci₄-aryl); and n is 0,1 ,2 or 3.

Yet another preferred embodiment of the invention relates to the compound of formula (I), wherein, the compound of formula (I) is:

10

wherein X is F, Cl, Br or I and R⁵ is selected from the group consisting of H, F, Cl,

SH, N0₂, N R¹⁰R¹¹, 0-Ci-Ci₂-alkyl, C=0(0)(Ci-Ci₂-alkyl), C=0(0H), C=0(NR¹²R¹³)

C=0(Ci-Ci₂-alkyl), CrCi₂-alkyl, C₂-Ci₂-alkenyl and C₂-Ci2-alkynyl; and

X^a is F, Cl or I.

In one embodiment, the present invention relates to an agrochemical mixture comprising at least one compound of formula (I) in free form or in the form of a stereoisomer or an agricultur ally acceptable salt or a tautomer or an isotopic form or a N-oxide or a S-oxide or a prodrug thereof, and at least one insecticidally active substance.

In one embodiment, the present invention relates to a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer or an agriculturally ac ceptable salt or a tautomer or an isotopic form of a N-oxide or a S-oxide or a prodrug thereof, and an auxiliary.

The compounds according to the present invention may be provided as mixtures with at least one mixing partner such as an insecticide, herbicide or biopesticide, or as compositions com prising an auxiliary and at least one compound of the present invention or a mixture thereof. Suitable formulations will be described further below. The compound of the formula (I) may have one or more centres of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures. Suitable compounds of the formula (I) also include all possible ge ometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be pre sent with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term "stereoisomer(s)" encompasses both optical isomers, such as enantio mers or diastereomers, the latter existing due to more than one centre of chirality in the mole cule, as well as geometrical isomers (cis/trans isomers).

Within the context of the present invention and as used herein, the term“tautomer” refers to the coexistence of two (or more) compounds that differ from each other only in the position of one (or more) mobile atoms and in electron distribution, for example, keto-enol tautomers.

Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic function ality.

In general, suitable“agriculturally useful salts” or“agriculturally acceptable salts” are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithi um, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C₄-alkyl, Ci-C₄-hydroxyalkyl, Ci-C₄-alkoxy, Ci-C₄-alkoxy-Ci-C₄-alkyl, hydroxy-Cr C₄-alkoxy-Ci-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise me- thylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trime- thylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2- hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sul- fonium ions, preferably tri(Ci-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C₄- alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The compound of formula (I) may be present in the form of their N-oxides. The term “N-oxide” includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides. The person skilled in the art knows if and in which positions compounds of the formula (I) of the present invention may form N-oxides. The compounds of the present invention may be amorphous or may exist in one or more differ ent crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of formula (I), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.

Within the context of this present application and as used herein, the term“isotopic forms” or “isotopically labeled forms” is a general term used for isotopic forms of compounds of formula, wherein one or more atoms of compounds of formula (I) are replaced by their respective iso topes. All isotopes of any particular atom or element as specified are contemplated within the scope of the compounds of the invention. Examples of isotopes that may be incorporated into the compounds disclosed herein include, but are not limited to, isotopes of hydrogen such as ²H (deuterium or D) and ³H, carbon such as ¹¹C, ¹³C and ¹⁴C, nitrogen such as ¹³N and ¹⁵N, oxygen such as ¹⁵0, ¹⁷0 and ¹⁸0, chlorine such as ³⁶CI, fluorine such as ¹⁸F and sul-phur such as ³⁵S. Representative examples of isotopic forms of the compounds of formula (I) may include, without limitation, deuterated compounds of formula (I). The term "deuterated" as used herein, by itself or used to modify a compound or group, refers to replacement of one or more hydrogen at- om(s), which is attached to carbon(s), with a deuterium atom.

The term“co-crystal” denotes a complex of the compounds according to the invention or a ste reoisomer, salt, tautomer or N-oxide thereof, with one or more other molecules (preferably one molecule type), wherein usually the ratio of the compound according to the invention and the other molecule is a stoichiometric ratio.

The term“solvate” denotes a co-complex of the compounds according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof, with solvent molecules. The solvent is usually liquid. Examples of solvents are methanol, ethanol, toluol, xylol. A preferred solvent which forms solvates is water, which solvates are referred to as“hydrates”. A solvate or hydrate is usually characterized by the presence of a fixed number of n molecules solvent per m molecules com pound according to the invention.

The term“active compound” denotes one or more compound selected compound of formula (I) and/or insecticide and/or herbicide.

The term“compound(s) of the invention” denotes at least one compound of formula (I).

The preparation of the compounds of formula (I) above may lead to them being obtained as isomer mixtures. If desired, these can be resolved by the methods customary for this purpose, such as crystallization or chromatography, also on optically active adsorbate, to give the pure isomers.

The term“pesticidally active compound” denotes one or more compound selected from insecti cide and/or biopesticide and/or herbicide.

Agronomically acceptable salts of the compound(s) of formula (I) can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.

Although the present invention will be described with respect to particular embodiments, this de scription is not to be construed in a limiting sense. As explained herein above, resistance therefore means that the original activity of a pesticide against the target organisms (arthropods, insects) decreases or is even lost, due to genetic ad aptation of the target organism.

“Resistant” to an insecticide and/or herbicide is understood to mean resistant to at least one insecticide and/or herbicide respectively, i.e. the insect and/or undesired vegetation may be resistant to only one, but also to several insecticides and/or herbicide respectively.

The resistance may be also against an insecticidal effect which is due to a genetic modification of a plant (modified or transgenic plant), which caused a resistance of the plant or crop to cer tain pests, especially insect pests, in susceptible insects.

This is to be understood to include plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those mentioned herein, es pecially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, Crylll B(b1 ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal pro teins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., and so on.

The compounds of formula (I) of the present invention can be applied in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions compris ing said mixtures as defined above. The components of said mixture can be applied simultane ously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture“in situ” on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

The application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.

Suitable application methods include inter alia soil treatment, seed treatment, in furrow applica tion, and foliar application. Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection. Seed treatment tech niques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting. In furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying at least one compound of formula (I) and pesticidally active com pound to the furrow, and closing the furrow. Foliar application refers to the application of the compound of formula (I) and pesticidally active compound to plant foliage, e.g. through spray equipment. For foliar applications, it can be advantageous to modify the behavior of the pests by use of pheromones in combination with the compounds of the present invention. Suitable pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as https://www.pherobase.com.

As used herein, the term "contacting" includes both direct contact (applying the com

pounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habi tat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant). The term“animal pest” includes arthropods, gastropods, and nematodes. Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects. Insects, which are of particular relevance for crops, are typically referred to as crop in sect pests.

The term "crop" refers to both, growing and harvested crops.

The term“plant” includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g. apples, pears, plums, peaches, nec tarines, almonds, cherries, papayas, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as beans, lentils, peas, alfalfa or soybeans; oil plants, such as rape- seed (oilseed rape), turnip rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, pumpkins, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as eggplant, spinach, lettuce (e.g. iceberg lettuce), chicory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cu curbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g. carnation, petunias, geranium/pelargoniums, pansies and impati- ens), shrubs, broad-leaved trees (e.g. poplar) or evergreens, e.g. conifers; eucalyptus; turf; lawn; grass such as grass for animal feed or ornamental uses. Preferred plants include potatoes sugar beets, tobacco, wheat, rye, bar-ley, oats, rice, corn, cotton, soybeans, rapeseed, leg umes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cu cumbers, tomatoes, beans or squashes.

The term“plant” is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a com bination thereof. Plants, which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice. In plants, which have been modified by mutagenesis or genetic engineering, one or more genes have been mutagenized or integrated into the genetic material of the plant. The one or more mutagenized or inte-grated genes are preferably selected from pat, epsps, crylAb, bar, cry1 Fa2, crylAc, cry34Ab1 , cry35AB1 , cry3A, cryF, cry1 F, mcry3a, cry2Ab2, cry3Bb1 , cry1A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asn1 , and ppo5. The mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant. Such properties, also known as traits, include abiotic stress tolerance, altered

growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quali ty, and pollination control. Of these properties, herbicide tolerance, e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance, is of particular importance. Several plants have been rendered tolerant to herbicides by mutagenesis, for example Clearfield® oilseed rape be ing tolerant to imidazolinones, e.g. imazamox. Alter-natively, genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available un der the trade names RoundupReady® (glyphosate) and Lib-ertyLink® (glufosinate). Further more, insect resistance is of importance, in particular lepidopteran insect resistance and coleop- teran insect resistance. Insect resistance is typically achieved by modifying plants by integrating cry and/or vip genes, which were isolated from Bacillus thurin-giensis (Bt), and code for the re spective Bt toxins. Genetically modified plants with insect re-sistance are commercially available under trade names including WideStrike®, Bollgard®, Agri-sure®, Herculex®, YieldGard®, Ge nuity®, and Intacta®. Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increas ing importance. In general, all relevant modified plants in connection with singular or stacked traits as well as detailed information as to the mutagenized or integrated genes and the respec tive events are available from websites of the organizations“International Service for the Acqui sition of Agri-biotech Applications (ISAAA)” (https://www.isaaa.org/gmapprovaldatabase) and “Center for Environmental Risk Assessment (CERA)” (https://cera-gmc.org/GMCropDatabase). Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which al ready have become resistant to the insecticidal trait of a plant and/or modified plant.

The term "plant propagation material" refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhi zomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.

The term“seed” embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.

The term“pesticide” refers to insecticides and/or herbicides.

In general, "pesticidally effective amount" means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various com

pounds/compositions used in the invention. A pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and dura tion, weather, target species, locus, mode of application, and the like.

In the case of soil treatment, in furrow application or of application to the pests dwelling place or nest, the quantity of active ingredients ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

For use in treating crop plants, e.g. by foliar application, the rate of application of the active in gredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hec tare, 30 to 40 g per hectare, or 40 to 50 g per hectare.

The compounds of the formula (I) of invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling’s roots and shoots against soil pests and foliar insects. The invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pre-germination with a composition comprising at least one compound of formula (I) of the invention and at least one active ingredient selected from insecticide. The protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling’s shoots from piercing and sucking insects, chewing insects and nematodes.

The term“seed treatment” comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods. Preferably, the seed treatment application of the compound of formula (I) is carried out by spraying or by dusting the seeds before sowing of the plants and before emer gence of the plants.

The invention also comprises seeds coated with or containing at least one compound of formula (I) of the invention and at least one active ingredient selected from insecticide. The term "coated with and/or containing" generally signifies that the active ingredients are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of applica tion. When the said propagation product is (re)planted, it may absorb the active ingredients. Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, orna mentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, ba nanas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucum bers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the at least one compound of formula (I) of the invention may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineer ing, and which e.g. tolerate the action of herbicides or insecticides. Such modified plants have been described in detail above.

Conventional seed treatment formulations include for example flowable concentrates FS, solu tions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the lat ter. Preferably, the formulations are applied such that germination is not included.

The compounds of formula (I) of the invention concentrations in ready-to-use formulations, which may be obtained after two-to-tenfold dilution, are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight. In a preferred embodiment, a FS formulation is used for seed treatment. Typically, a FS formu lation may comprise 1-800 g/l of active ingredient selected from at least one compound of for mula (I), 1-200 g/l Surfactant, 0 to 200 g/l anti-freezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Especially preferred FS formulations of the compounds of the invention for seed treatment usu ally comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient selected from at least one compound of formula (I), from 0.1 to 20 % by weight (1 to 200 g/l) of at least one sur factant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g. 1 to 40 % by weight of a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and op tionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.

In the treatment of seed, the application rates of the compounds of formula (I) of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.

The invention therefore also relates to seed comprising a compound of the invention, or an agri culturally useful salt thereof, as defined herein. The amount of the compound of the invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

In one embodiment, the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.

Method of controlling insecticide resistant insects

In one embodiment, the present invention relates to the use of the compound of Formula (I) as cytochrome P450 inhibitor.

In one embodiment, the present invention provides a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant.

In one embodiment, the present invention provides a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which insects are resistant. In another embodiment, the present invention provides a method of protecting a crop of useful plants susceptible to and/or under attack by insects, which are resistant to an insecticide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insecticide resistant insects, a composition comprising at least one com pound formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.

In another embodiment, the present invention provides a method of controlling resistance to one or more insecticides in insects, which comprises alternately or simultaneously applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the insecticide, towards which the insects are re sistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects.

In another embodiment, the present invention provides a method, which process comprises treating the insect, the plant, or the plant propagation material selected from the group consist ing of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against insect attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with an effective amount of at least one compound of formula (I) in free form or in the form of a stereoi somer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, to wards which insects are resistant.

In yet another embodiment, the present invention provides a method, wherein the step of treat ing the seed is followed by a treatment of the emerged host plants with a composition compris ing at least one compound of formula (I), in free form or in the form of a stereoisomer, an agri culturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a de rivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.

In one embodiment, the present invention provides a method of controlling resistance to one or more insecticides in insects, which comprises alternately or simultaneously applying at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the insecticide, towards which the insects are resistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects; wherein the insecticide to which the insect is resistant is from the following list of pesticides, grouped and numbered according the Mode of Action Classification of the Insecti cide Resistance Action Committee (I RAC).

The following list M of pesticides, grouped and numbered according the Mode of Action Classi fication of the Insecticide Resistance Action Committee (I RAC), together with which the com pounds of the invention can be used and with which potential synergistic effects might be pro duced, is intended to illustrate the possible combinations, but not to impose any limitation: M.1 Acetylcholine esterase (AChE) inhibitors: M.1A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M .2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M AC sulfoxaflor; M AD flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon; M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;

M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M.21A METI acaricides and in secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-^,ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-^,methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}-'amino)benzoyl]-1 ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-'carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro-'methyl)pyrazole-3- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-

2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine ; M .UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-

3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN .9.b): fluxametamide ; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11 .c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M .U N .1 1.d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;

M . U N .1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;

M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ^^-tetrafluoro-Htrifluoromethyl^ethyll-O- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S-^^-iodo^-ll ^^^-tetrafluoro-l-Ctrifluoromethy -'ethyll-e-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.UN.1 1.i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 j) 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethy -'propyllphenyl^-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; M.UN.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;

M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ^^^-tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoylJ-'phenyll^-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M .U N .12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M .UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5- yl]pyridine-2-carboxamide; M.U N.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide ; M.UN.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN .12.g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio- propanamide; M .U N .12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N ,2-dimethyl-3-methylthio- propanamide; M .U N.12.1) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M .U N.12.m) N-^-Chloro^-CS-pyri-'dy thiazol-S-yll-N-ethyl-S-methylthio- propanamide ;

M.UN.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;

M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; M.UN.16e) N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.UN.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M .UN.16g) 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide; M.U N.16h) N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.U N.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide,

M. UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M. UN.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide; M. UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide; M. UN.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M .U N .18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;

M.UN.19 sarolaner , M.UN.20 lotilaner ;

M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ; M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;

M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4FI-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazole-3-carboxamide ; M.UN.25 acynonapyr ; M.UN.26 benzpy-rimoxan ; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)-4- (trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide .

The commercially available compounds of the group M listed above may be found in The Pes ticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015) among other publications. The online Pesticide Manual is updated regularly and is accessible through https://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common names is

https://www.alanwood.net/pesticides.

The M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456. M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839. M.4A.2, guadipyr , is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO

2007/101369. M.22B.1 is described in CN 10171577 and M.22B.2 in CN 102126994. Spiropidion M.23.1 is known from WO 2014/191271. M .28.1 and M .28.2 are known from W02007/101540. M.28.3 is described in W02005/077934. M.28.4 is described in W02007/043677. M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO

2013/024010, M.28.5Ϊ) is described in WO2011/085575, M.28.5j) in W02008/134969, M.28.5k) in US2011/046186 and M .28.5I) in WO2012/034403. M.28.6 can be found in WO2012/034472.

M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911. M.UN.5 is de scribed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672. M.U N.8 is known from WO2013/055584. M .UN .9.a) is described in WO2013/050317. M.UN.9.b) is described in WO2014/126208. M.UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO 2010/127926. M.UN.12.a) to M.UN.12.C) are known from WO2010/006713, M.UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO

2010/129497 . M. UN.14a) and M. UN.14b) are known from W02007/101369. M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497. M. UN.17a) to M.UN.17 ) are described in WO2015/038503. M.UN.18a) to M.UN.18d) are described in US2014/0213448. M.UN.19 is de-scribed in WO2014/036056. M.UN.20 is known from WO2014/090918. M.UN.21 is known from EP2910126. M. UN.22a and M. UN.22b are known from WO2015/059039 and W02015/190316. M.UN.23a and M .UN .23b are known from WO2013/050302. M.UN.24a and M. UN.24b are known from WO2012/126766. Acynonapyr M.U N.25 is known from WO

201 1/105506. Benzpyrimoxan M .UN.26 is known from W02016/104516. M.UN.27 is known from WO2016174049.

In yet another embodiment, the present invention provides a method, wherein the resistant in sects developed resistance against insecticides, avermectins, milbemycins, cyclodienes, phos phines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta- ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators or antifeedants. In particular, wherein the resistant insects developed resistance against pyrethrums, pyrethroids, spynosins and/or anthranilamide.

Thus, in an embodiment of the invention there is provided a method of controlling insects which are resistant to a neonicotinoid insecticide, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof to said resistant insects as cytochrome P450 inhibitor and the neonicotinoid insecticide.

Thus, in another embodiment of the invention there is provided, a method of controlling insects which are resistant to a pyrethroid insecticide, such as such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyre- thrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin, which method comprises applying a composition comprising at least one com pound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the pyrethroid insecticide, to said resistant insects. Thus, in another embodiment of the invention there is provided a method of controlling insects which are resistant to an organophosphate insecticide, such as primicarb, which method com prises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the organophosphate insecticide, to said resistant insects. Thus, in yet another embodiment of the invention there is provided a method of controlling in sects which are resistant to a feeding blocker insecticide, such as pymetrozine, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibi tor and the feeding blocker insecticide, to said resistant insects.

In one embodiment, the present invention provides a method of controlling insects, which are resistant to an insecticide, are from the order Lepidoptera, from the order Coleoptera, from the order Diptera, from the order Thysanoptera, from the order Hemiptera, from the order Hymenop- tera, from the order Orthoptera, from the class Arachnida, from the Phylum Nematoda, from the order Isoptera, from the order Blattodea from the order Siphonoptera, from the order Thysanura, from the class Chilopoda, from the class Diplopoda, from the class Symphyla, from the order Dermaptera, from the order Collembola, from the order Isopoda, from the order anoplura, from the Phylum Mollusca or from the order Phthiraptera, which method comprises applying a com position comprising at least one compound of formula (I) in free form or in the form of a stereoi somer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof to said resistant insects as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant.

In another embodiment, the method of the present invention controls insects of the suborder Lepidoptera, such as Plutella maculipennis, Plutella xylostella, Trichophaga tapetzella, Trichop- lusia spp. such as T. ni; Tuta (=Scrobipalpula) absoluta.

In another embodiment, the method of the present invention control pests of the suborder of Arachnida including Eotetranychus spp., Eutetranychus spp., Oligonychus spp., Petrobia latens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseulus, T. telarius and T. urticae; Bryobia praetiosa; Panonychus spp. such as P. ulmi, P. citri; Me- tatetranychus spp.

Another embodiment of the invention provides a method of controlling species of insects, which have shown resistance effects against insecticides, in particular from the order of Hemiptera with their suborder of Homoptera and Heteroptera, but also from the orders Thysanoptera, Lep idoptera, Coleoptera or Diptera.

In another embodiment, the method of the present invention may further control pests of the suborder heteroptera including bugs, such as shield bugs, seed bugs, assassin bugs, flower bugs, stink bugs, sweetpotato bugs and the water bugs.

By virtue of the surprising ability of the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as inhibitors to p450 related metabolic path ways, the invention also provides a method of protecting a crop of useful plants, wherein said crop is susceptible to and/or under attack from insects, which are resistant towards insecticide. Such a method involves applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a composition comprising at least one compound of formu la (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cyto chrome P450 inhibitor and the insecticide, towards which insects are resistant. The compound of formula (I) of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.

In another embodiment of the invention, the compounds of the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:

insects from the order of Lepidoptera, for example Achroia grisella, Ac/eris spp. such as A. fim- briana, A. g!overana, A. variana; Acro/epiopsis assectella, Acronicta major, A doxophyes spp. such as A. cyrtosema, A. orana; Aedia leucometas, Agrotis spp. such as A. exdamationis, A. fucosa, A. ipsi/on, A. orthogoma, A. segetum, A. subterranea; Alabama argillacea, A/eurodicus dispersus, Alsophila pometaria, Ampelophaga rubiginosa, Amye!ois transitella, Anacampsis sarcitella, Anagasta kuehniella, Anarsia lineatella, Anisota senatoria, Antheraea pernyi, Anticar- sia (=Thermesia) spp. such as A. gemmata!is; Apamea spp. , Aproaerema modicella, Archips spp. such as A. argyrospi!a, A. fuscocupreanus, A. rosana, A. xyloseanus; Argyresthia conjuge!- la, A rgyroploce spp., Argyrotaenia spp. such as A. ve!utinana; Athetis mindara, Austroasca vi- ridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedel Ha spp., Bon- agota salubricola, Borbo cinnara, Bucculatrix thurberiella, Bupa!us piniarius, Busseo/a spp., Cacoecia spp. such as C. murinana, C. podana; Cactoblastis cactorum, Cadra cautella, Calingo braziliensis, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, ChHo pp. such as C. Indi- cus, C. suppressa/is, C. partellus; Choreutis pariana, Choristoneura spp. such as C. conf!ictana, C. fumiferana, C. longicellana, C. murinana, C. occidentalis, C. rosaceana; Chrysodeixis (=Pseudoplusia) spp. such as C. eriosoma, C. inc/udens; Cirphis unipuncta, C!ysia ambiguella, Cnapha!ocerus spp., Cnaphalocrocis medinalis, Cnephasiasp ., Cochyl/s hospes, Coleophora spp., Colias eurytheme, Conopomorpha spp., Conotrache!us spp., Copitarsia spp., Corcyra cepha/onica, Crambus caliginosellus, Crambus teterrellus, Crocidosema (=Epinotia) aporema, Cydalima (=Diaphania) perspectalis, Cydia (=Carpocapsa) spp. such as C. pomonella, C.

latiferreana; Da!aca noctuides, Datana integerrima, Dasychira pinicola, DendroHmus spp. such as D. pini, D. spectabilis, D. sibiricus; Desmia funeralis, Diaphania spp. such as D. nitidalis, D. hyalinata; Diatraea grandiosella, Diatraea saccharalis, Diphthera festiva, Earias spp. such as E. insu/ana, E. vittella; Ecdytolopha aurantianu, Egira (=Xylomyges) curialis, Elasmopalpus Hgno- se/lus, Eldana saccharina, Endopiza viteana, Ennomos subsignaria, Eoreuma loftini, Ephestia spp. such as E. cautella, E. elutella, E. kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiellas ., Eulia spp., EupoecHia ambiguella, Euproctis chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Feltia spp. such as F. subterra nean; Galleria mellonella, Gracillariaspp., Grapholitaspp. such as G. funebrana, G. mo!esta, G. inopinata; Halysidota spp., Harrisina americana, Hedyleptas ., Helicoverpas p. such as H. armigera (=Heliothis armigera), H. zea (=Heliothis zea); He/iothis spp. such as H. assulta, H. subftexa, H. virescens; Hellula spp. such as H. undalis, H. rogata!is; He/ocoverpa ge/otopoeon, Hemileuca o!iviae, Herpetogramma licarsisalis, Hibernia defo!iaria, Hofmannophila pseu- dospretella, Homoeosoma electellum, Homona magnanima, Hypena scabra, Hyphantria cunea, Hyponomeuta pad el la, Hyponomeuta m aline Hus, Kakivoria flavofasciata, Keiferia lycopersicella, Lambdina fiscellaria fiscellaria, Lambdina fiscellaria lugubrosa, Lamprosema indicata,

Laspeyresia mo!esta, Leguminivora glycinivorella, Lerodea eufa!a, Leucinodes orbona!is, Leu- coma saiicis, Leucoptera spp. such as L. coffeella, L. scitella; Leuminivora lycinivorella, LithocoHetis blancardella, Lithophane antennata, Uattia octo (=Amyna axis), Lobesia botrana, Lophocampa spp., Loxagrotis a!bicosta, Loxostege spp. such as L. sticticalis, L cereralis;

Lymantria spp. such as L. dispar, L. monacha; Lyonetia cierkeiia, Lyonetia prunifoiieiia, Maiaco- soma spp. such as M. americanum, M. caiifornicum, M. constrictum, M. neustria; Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quin- quemacuiata, M. sexta; Marasmia spp, Marmara s ., Maruca testuiaiis, Megaiopyge ianata, Meianchra picta, Meianitis ieda, Mods spp. such as M. iapites, M. repanda; Mods iatipes, Mon- ochroa fragariae, Mythimna separata, Nemapogon doaceiia, Neoieucinodes eiegantaiis, Nepytiaspp., Nymphu/a spp., Oike ficus spp., Omiodes indicata, Omphisa anastomosaiis, Oper- ophtera brumata, Orgyia pseudotsugata, Oria spp., Orthaga thyrisaiis, Ostrinia spp. such as O. nubiiaiis; Ouiema oryzae, Paieacrita vernata, Panoiis fiammea, Parnara spp., Papaipema nebris, Papiiio cresphontes, Paramyeiois transiteiia, Paranthrene regaiis, Paysandisia archon, Pectinophora spp. such as P. gossypieiia; Peridroma saucia, Periieucoptera spp., such as P. coffeella; Phaiera bucephaia, Phryganidia caiifornica, Phthorimaea spp. such as P. opercuieiia; Phyiiocnistis citreiia, Phyiionorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; Pieris spp. such as P. brassicae, P. rapae, P. napi; PHocrocis tripunctata, Piathy- pena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P. stultana; P!atyptiHa cardui- dactyla, P!ebejus argus, Piodia interpunctella, Plusia spp, Plutella maculipennis, Plutella xy- lostella, Pontia protodica, Prays spp., Prodenia spp., Proxenus /epigone, Pseuda!etia spp. such as P. sequax, P. unipuncta; Pyrausta nubiiaiis, Rachipiusia nu, Richia albicosta, Rhizobius ven- tra!is, Rhyacionia frustrana, Sabulodes aegrotata, Schizura concinna, Schoenobius spp., Schreckensteinia festaliella, Scirpophaga spp. such as S. incertulas, S. innotata; Scotia segetum, Sesamia spp. such as S. inferens, Seudyra subfiava, Sitotroga cereaieiia, Spargan- othis piiieriana, Spiionota iechriaspis, S. oceiiana, Spodoptera (=Lamphygma) spp. such as S. eridania, S. exigua, S. frugiperda, S. iatisfascia, S. iittoraiis, S. iitura, S. omithogaiii; Stigme/la spp., Stomopteryx subseciveila, Strymon bazochii, Syiepta derogata, Synanthedon spp. such as S. exitiosa, Tecia soianivora, Teiehin iicus, Thaumatopoea pityocampa, Thaumatotibia

(=Cryptophiebia) ieucotreta, Thaumetopoea pityocampa, Theda spp., Theresimima am- peiophaga, Thyrinteina spp, Tiidenia inconspicueiia, Tinea spp. such as T doaceiia, T pei- iioneiia; Tineoia bissei/iel/a, Tortrix spp. such as T. viridana; Trichophaga tapetzeiia, Trichopiu- sia spp. such as T. ni; Tuta (=Scrobipaipuia) absoiuta, Udea spp. such as U. rubigaiis, U. rubi- gaiis; Virachoia spp., Yponomeuta padeiia, and Zeiraphera canadensis;

insects from the order of Coleoptera, for example Acaiymma vittatum, Acanthoscehdes obtec- tus, Adoretus spp., Ageiastica aini, Agriius spp. such as A. anxius, A. pianipennis, A. sinuatus; Agriotes spp. such as A. fuscicoiiis, A. iineatus, A. obscurus; Aiphitobius diaperinus, Amphimai- ius soistitiaiis, Anisandrus dispar, Anisopiia austriaca, Anobium punctatum, Anomaia corpuien- ta, Anomaia rufocuprea, Anopiophora spp. such as A. giabripennis; Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogo- nia spp., Athous haemorrhoidaiis, Atomaria spp. such as A. linearis; Attagenus spp., Auia- cophora femoraiis, Biastophagus piniperda, BHtophaga undata, Bruchidius obtectus, Bruchus spp. such as B. ientis, B. pisorum, B. rufimanus; Byctiscus betuiae, Callidiellum rufipenne, Cai- iopistria f/oridensis, Caiiosobruchus chinensis, Cameraria ohrideiia, Cassida nebuiosa, Ceroto- ma trifurcata, Cetonia aurata, Ceuthorhynchus spp. such as C. assimiiis, C. napi; Chaetocnema tibialis, Cieonus mendicus, Conoderus spp. such as C. vespertinus; Conotracheius nenuphar, Cosmopolites spp., Costeiytra zeaiandica, Crioceris asparagi, Cryptoiestes ferrugineus, Cryp- torhynchus iapathi, Ctenicera spp. such as C. destructor; Curcu/io spp., Cyiindrocopturus spp., Cyciocephaia spp., Dactyiispa baiyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunctata, D. speciosa, D. iongicornis, D. semipunctata, D. virgifera; Diaprepes ab breviates, Dichoc rods spp., Diciadispa armigera, Diioboderus abderus, Diocaiandra frumenti (Diocaiandra stigmaticoiiis), Enaphaiodes rufuius, Epi/achna spp. such as E. varivestis, E vigintioctomacuiata; Epitrix spp. such as E hirtipennis, E simiiaris; Eutheoia humi/is, Eu- tinobothrus brasi/iensis, Faustinus cubae, Gibbium psyiioides, Gnathocerus cornutus, Heiiuia undaiis, Heteronychus arator, Hyiamorpha eiegans, Hyiobius abietis, Hyiotrupes bajuius, Hy- pera spp. such as H. brunneipennis, H. postica; Hypomeces squamosus, Hypothenemus spp., ips typographus, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lath- rid ius spp., Lema spp. such as L. biiineata, L meianopus; Leptinotarsa spp. such as L. decem- iineata; Leptispa pygmaea, Limonius catifornicus, Lissorhoptrus oryzophiius, Lixus spp., Lu- perodes spp., Lyctus spp. such as L. bruneus; Liogenys fuscus, Macrodactyius spp. such as M. subspinosus; Maiadera matrida, Megapiatypus mutates, Megasceiis spp., Meianotus com munis, Meiigethes spp. such as M. aeneus; Meioiontha spp. such as M. hippocastani, M. meioi- ontha; Metamasius hemipterus, Microtheca spp., Migdoius spp. such as M. fryanus, Monocha- mus spp. such as M. aiternatus; Naupactus xanthographus, Niptus holo/eucus, Oberia brevis, Oemona hirta, Oryctes rhinoceros, Oryzaephiius surinamensis, Oryzaphagus oryzae, Otiorrhyn- chus su/catus, Otiorrhynchus ova t us, Otiorrhynchus su/catus, Ouiema meianopus, Ouiema ory zae, Oxycetonia jucunda, Phaedon spp. such as P. brassicae, P. cochieariae; Phoracantha re- curva, Phyiiobius pyri, Phyiiopertha horticoia, Phyiiophaga spp. such as P. heiieri; Phyiiotreta spp. such as P. chrysocephaia, P. nemorum, P. strioiata, P. vittuia; Phyiiopertha horticoia, Pop- iiiia japonica, Premnotrypes spp., Psacothea hiiaris, Psyf/iodes chrysocephaia, Prostephanus truncates, Psyiiiodes spp., P tin us spp., Pulga saitona, Rhizopertha dominica, Rhynchophorus spp. such as R. biiiineatus, R. ferrugineus, R. paimarum, R. phoenicis, R. vuineratus; Saperda Candida, Sco/ytus schevyrewi, Scyphophorus acupunctatus, Sitona iineatus, Sitophiius spp. such as S. granaria, S. oryzae, S. zeamais; Sphenophorus spp. such as S. ievis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphy/etes spp., Tanymecus spp., Tenebrio moiitor, Tenebrioides mauretanicus, Tribolium spp. such as T castaneum; Trogoderma spp., Tychius spp., Xyiotrechus spp. such as X. pyrrhoderus; and, Za- brus spp. such as Z. tenebrioides;

insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. aibopictus, A. vexans; Anastrepha iudens, Anopheles spp. such as A. aibimanus, A. crucians, A. freeborni, A. gambiae, A. ieucosphyrus, A. macuiipennis, A. minimus, A. quadrimacuiatus, A. sinensis; Bac- trocera invade ns, Bibio hortuianus, Caiiiphora erythrocephaia, Caiiiphora vicina, Ceratitis capi- tata, Chrysomyia spp. such as C. bezziana, C. hominivorax, C. maceiiaria; Chrysops atianticus, Chrysops discaiis, Chrysops siiacea, Cochiiomyia spp. such as C. hominivorax; Contarinia spp. such as C. sorghicoia; Cordyiobia anthropophaga, Cut ex spp. such as C. nigripaipus, C.

pipiens, C. quinquefasciatus, C. tarsaiis, C. tritaeniorhynchus; Cu/icoides furens, Cuiiseta inor nate, Cuiiseta meianura, Cuterebra spp., Dacus cucurbitae, Dacus oieae, Dasineura brassicae, Dasineura oxycoccana, Delia spp. such as D. antique, D. coarctata, D. piatura, D. radicum; Dermatobia hominis, Drosophila spp. such as D. suzukii, Fannia spp. such as F. canicuiaris; Gastraphilus spp. such as G. intestinalis; Geomyza tipunctata, Giossina spp. such as G. fusci- pes, G. morsitans, G. palpalis, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippeiates spp., Hylemyia spp. such as H. piatura; Hypoderma spp. such as H. Hneata; Hyppo- bosca spp., Hydrellia phiiippina, Leptoconops torrens, Liriomyza spp. such as L. sativae, L. trifo- iii; Luc i Ha spp. such as L. caprina, L. cuprina, L. sericata; Lycoria pectora!is, Mansonia titillanus, Mayetio/a spp. such as M. destructor; Musca spp. such as M. autumnalis , M. domestica; Musci- na stabu!ans, Oestrus s . such as O. ovis; Opomyza ftorum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. anti- qua, P. brassicae, P. coarctata; Phytomyza gymnostoma, Prosimulium mixtum, Psi/a rosae, Psorophora cotumbiae, Psorophora discolor, Rhagoietis spp. such as R. cerasi, R. cingulate, R. indifferens, R. mendax, R. pomoneiia; Riveiiia quadrifasciata, Sarcophaga spp. such as S. haemorrhoidaiis; Simuiium vittatum, Sitodip/osis moseiiana, Stomoxys spp. such as S. caici- trans; Tabanus spp. such as T. atratus, T bovinus, T. iineoia, T simiiis; Tannia spp., Thecodi- piosis japonensis, Tipuia oieracea, Tipuia paiudosa, and Wohifahrtia spp;

insects from the order of Thysanoptera for example, Baiiothrips biformis, Dichromothrips cor- betti, Dichromothrips ssp., Echinothrips americanus, Enneothrips Havens, Frankiinieiia spp. such as F. fusca, F. occidentaiis, F. tritici; Heiiothrips spp., Hercinothrips femoraiis, Kakothrips spp., Microcephaiothrips abdominaiis, Neohydatothrips samayunkur, Pezothrips keiiyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S. citri, S. dorsalis, S. perseae; Stenchae- tothrips spp, Taeniothrips cardamoni, Taeniothrips inconsequens, Thrips spp. such as T. imagi nes, T. hawaiiensis, T. oryzae, T. paimi, T. parvispinus, T. tabaci;

insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hiiare; Acyrthosipon spp. such as A. onobrychis, A. pisum; Ade/ges iaricis, Ade/ges tsugae,

A del phoc oris spp., such as A. rapidus, A. superbus; Aeneolamia spp., Agonoscena spp., Au- iacorthum soiani, Aieurocanthus wogiumi, Aieurodes spp., Aieurodicus disperses, Aleurofobus barodensis, Aieurothrixus spp., Amrasca spp., Anasa tristis, Antestiopsis spp., Anuraphis car- dui, Aonidieiia spp., Aphanostigma piri, Aphiduia nasturtii, Aphis spp. such as A. cracc/Vora, A. fabae, A. forbesi, A. gossypii, A. grossuiariae, A. maidiradicis, A. pomi, A. sambuci, A. schnei- deri, A. spiraecoia; Arboridia apicaiis, Ariius critatus, Aspidieiia spp., Aspidiotus spp., Atanus spp., Auiacaspis yasumatsui, Auiacorthum soiani, Bactericera cockereiii (Paratrioza cockereiii), Bemisia spp. such as B. argentifoiii, B. tabaci (Aieurodes tabaci); Bliss us spp. such as B. ieu- copterus; Brachycaudus spp. such as B. cardui, B. heiichrysi, B. persicae, B. prunicoia; Brachy- co/us spp., Brachycoryneiia asparagi, Brevicoryne brassicae, Cacopsyiia spp. such as C. fuigu- raiis, C. pyricoia (Psyiia piri); Caiiigypona marginata, Caiocoris spp., Campyiomma iivida, Capi- tophorus horni, Carneocephaia fuigida, Cave/erius spp., Cerapiastes spp., Ceratovacuna ianig- era, Ceropiastes ceriferus, Cerosipha gossypii, Chaetosiphon fragaefoiii, Chionaspis tegaiensis, Chiorita onukii, Chromaphis jugiandicoia, Chrysomphaius ficus, Cicaduiina mbiia, Cimex spp. such as C. hemipterus, C. iectuiarius; Coccomytiius haiii, Coccus spp. such as C. hesperidum,

C. pseudomagnoiiarum, Corythucha arcuata, Creontiades di/utus, Cryptomyzus ribis,

Chrysomphaius aonidum, Cryptomyzus ribis, Ctenarytaina spatuiata, Cyrtopeitis notatus, Daibu- ius spp., Dasynus piperis, Diaieurodes spp. such as D. citrifoiii; Daibuius maidis, Diaphorina spp. such as D. citri; Dias pis spp. such as D. bromeiiae; Dicheiops furcatus, Diconocoris hewet- ti, Doratis spp., Dreyfusia nordmannianae, Dreyfusia piceae, Drosichaspp., Dys aphis spp. such as D. piantaginea, D. pyri, D. radicoia; Dysauiacorthum pseudosoiani, Dysdercus spp. such as D. cingulatus, D. intermedius; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp. such as E. fabae, E. soiana; Epidiaspis ieperii, Eriosoma spp. such as E. ianigerum, E. pyricoia; Erythroneura spp., Eurygaster spp. such as E. integriceps; Euscelis bilobatus, Euschistus spp. such as E. herns, E. impictiventris, E. servus; Fiorinia theae, Geococcus coffeae, Glycaspis brimblecombei, Halyomorpha spp. such as H. halys; He/iope/tis spp., Homalodisca vitripennis (=H. coagu/ata), Horcias nobilellus, Hya/opterus pruni, Hyperomyzus lactucae, lcerya spp. such as /. purchase; Idiocerus spp. , Idioscopus spp., Laode!phax striate/lus, Lecanium spp ., Lecanoideus floccissimus, Lepidosaphes spp. such as L. u!tni; L eptocorisa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L. hesperus, L. Uneo!aris, L. pratensis; Ma- cone/licoccus hirsutus, Marchalina hellenica, Macropes excavatus, Macrosiphum spp. such as M. rosae, M. a venae, M. euphorbiae; Macros teles quadrilineatus, Mahanarva fimbriolata, Meg- acopta cribraria, Megoura viciae, Melanaphis pyrarius, Metanaphis sacchari, Melanocallis (=Tinocallis) caryaefo!iae, Metcafieiia spp., Metopolophium dirhodum, Monellia costa!is, Monet- liopsis pecanis, Myzocallis coryli, Murgantia spp., Myzus spp. such as M. ascalonicus, M.

cerasi, M. nicotianae, M. persicae, M. varians; Nasonovia ribis-nigri, Neotoxoptera formosana, Neomega/otomus spp, Nephotettlx spp. such as N. malayanus, N. nigropictus, N. parvus, N. virescens; Nezara spp. such as N. viridula; NHaparvata lugens, Nysius huttoni, Oeba!us spp. such as O. pugnax; Oncometopia spp., Orthezia praelonga, Oxycaraenus hya!inipennis, Para- bemisia myricae, Pariatoria spp., Parthenolecanium spp. such as P. corni, P. persicae; Pemphi gus spp. such as P. bursarius, P. populivenae; Peregrinus maidis, Perkinsiella saccharicida, Phenacoccus spp. such as P. aceris, P. gossypii; Ph/oeomyzus passerinii, Phorodon humuli, Phylloxera s . such as P. devastatrix, Piesma quadrata, Piezodorus spp. such as P. guildinii; Pinnaspis aspidistrae, Planococcus spp. such as P. citri, P. ficus; Prosapia bicincta, Protopuivi- naria pyriformis, Psa/lus seriatus, Pseudacysta persea, Pseudaulacaspis pentagona, Pseudo coccus spp. such as P. comstocki; Psylla spp. such as P. mall; Pteromalus spp., PuMnaria amygda/i, Pyri/la spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastro- coccus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascaloni cus, Rhopa!osiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R. padi; Saga- t odes spp., Sahibergeiia singuiaris, Saissetia spp., Sappaphis maia, Sappaphis maii, Scapto- coris spp., Scaphoides titanus, Schizaphis graminum, Schizoneura lanuginosa, Scotinophora spp., Se/enaspidus articu/atus, Sitobion avenae, Sogata spp., Sogateiia furcifera, So/ubea insu la ris, S pi ssi stilus festinus (=Stictocephaia festina), Stephanitis nashi, Stephanitis pyrioides, Stephanitis takeyai, Tenaiaphara maiayensis, Tetraieurodes perseae, Therioaphis maculate, Thyanta spp. such as T. accerra, T perditor; Tibraca spp., Tomaspis spp., Toxoptera spp. such as T. aurantii; Triaieurodes spp. such as T. abutiionea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhiocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifoiii, Insects from the order Hymenoptera for example Acanthomyops interjectus, Athaiia rosae, Atta spp. such as A. capiguara, A. cephaiotes, A. cephaiotes, A. laevigata, A. robusta, A. sexdens,

A. texana, Bom bus spp., Brachymyrmex spp., Camponotus spp. such as C. Horidanus, C. pennsyivanicus, C. modoc; Cardiocondyia nuda, Chaiibion sp, Crematogaster spp., Dasymutiiia occidentaiis, Diprion spp., Doiichovespuia macuiata, Dorymyrmex spp., Dryocosmus kuriphiius, Formica spp., Hopiocampa spp. such as H. minuta, H. testudinea; iridomyrmex humiiis, Lasius spp. such as L. niger, Linepithema humiie, Liometopum spp., Leptocybe invasa, Monomorium spp. such as M. pharaonis, Monomorium, Nyiandria fuiva, Pachycondyia chinensis, Paratre- china longicornis, Para vespula s p p . , such as P. germanica, P. pennsy!vanica, P. vulgaris; Phei- doie spp. such as P. megacephaia; Pogonomyrmex s p p . such as P. barbatus, P. caiifornicus, Po/istes rubiginosa, Prenoiepis impairs, Pseudomyrmex gracilis, Sche!ipron spp., Sirex cya- neus, Sotenopsis spp. such as S. geminata, S.invicta, S. moiesta, S. richteri, S. xyioni, Sphe- cius speciosus, Sphex spp., Tapinoma spp. such as T. meianocephaium, T. sessile; Tetramori- um spp. such as T. caespitum, T. bicarinatum, Vespa s . such as V crabro; Vespuia spp. such as V. squamosal; Wasmannia auropunctata, Xyiocopa sp\

Insects from the order Orthoptera for example Acheta domesticus, Caiiiptamus itaiicus, Chor- toicetes terminifera, Ceuthophi/us spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryiiotaipa spp. such as G. africana, G. gryiiotaipa; Gryiius spp., Hierogiyphus daganensis, Kraussaria anguiifera, Locusta spp. such as L. migratoria, L. pardaiina; Meianopius spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M. spretus; Nomadacris sep- temfasciata, Oeda/eus senega/ensis, Scapteriscus spp., Schistocerca spp. such as S. america- na, S. gregaria, Stemopeimatus spp., Tachycines asynamorus, and Zonozerus variegatus; Pests from the Class Arachnida for example Acari.e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Ambiyomma spp. (e.g. A. americanum, A. variegatum, A. macuiatum), Argas spp. such as A. persicu ), Boophiius spp. such as B. annuiatus, B. decoioratus, B. mi- cropius, Dermacentor spp. such as D.siivarum, D. andersoni, D. variabiiis, Hyaiomma spp. such as H. truncatum, ixodes spp. such as i. ricinus, i. rubicundus, i. scapuiaris, i. hoiocycius, i. pacificus, Rhipicephaius sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gaiiinae, Psoroptes spp. such as P. ovis, Rhipicephaius spp. such as R. sanguineus, R. appendicuiatus, Rhipicephaius evertsi, Rhizogiyphus spp., Sarcoptes spp. such asS. Scabiei, and Family Eriophyidae including Aceria spp. such as A. she/doni, A. anthocoptes, Acaititus spp., Acuiops spp. such as A. iycopersici, A. pe/ekassi, Acufus spp. such as A. schiechtendaii; Coiomerus vitis, Epitrimerus pyri, Phyiio- coptruta oieivora; Eriophytes ribis and Eriophyes spp. such as Eriophyes she/doni, Family Tar- sonemidae including Hemitarsonemus spp., Phytonemus paiiidus and Poiyphagotarsonemus iatus, Stenotarsonemus spp. Steneotarsonemus spinki, Family Tenuipalpidae including Brevi- palpus spp. such as B. Phoenicia, Family Tetranychidae including Eotetranychus spp., Eute- tranychus spp., Oiigonychus spp., Petrobia iatens, Tetranychus spp. such as T. cinnabarinus, T. evansi, T. kanzawai, T, pacificus, T. phaseuius, T. teiarius and T. urticae, Bryobia praetiosa, Panonychus spp. such as P. uimi, P. citrr, Metatetranychus spp. and Oiigonychus spp. such as O. pratensis, O. perseae, Vasates iycopersici, Raoieiia indica, F¾/??//yCarpoglyphidae including Carpogiyphus spp.; Penthaieidae spp. such as Haiotydeus destructor, Family Demodicidae with species such as Demodex spp.; Family Trombicidea including Trombicuia spp. ; Family Macro- nyssidae including Ornothonyss us spp. ; Family Pyemotidae including Pyemotes tritici, Tyropha- gus putrescentiae, Family Acaridae including Acarus sira, Family Araneida including Latrodec- tus mactans, Tegenaria agrestis, Chiracanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosce/es red us a,

Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Meioidogyne spp. such as M. hapia, M. incognita, M. javanica; cyst-forming nema todes, Giobodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. gly cines, H. schachtii, H. trifoiii; Seed gall nematodes, Anguina spp.; Stem and foliar nematodes, Apheienchoides spp. such as A. besseyi; Sting nematodes, Beionoiaimus spp. such as B. ion- gicaudatus; Pine nematodes, Bursaphelenchus spp. such as B. lignicolus, B. xylophilus; Ring nematodes, Criconem a spp., Criconemella spp. such as C. xenopiax and C. ornata; and, Criconemoides spp. such as Criconemoides informis; Mesocriconema spp.; Stem and bulb nematodes, Dityienchus spp. such as D. destructor, D. dipsaci; Awl nematodes, Dotichodorus spp.; Spiral nematodes, Hetiocotytenchus mu/ticinctus; Sheath and sheathoid nematodes, Hem- icyctiophora spp. and Hemicriconemoides spp. / Hirshmannietta spp.; Lance nematodes, Hop- toaimus spp.; False rootknot nematodes, Nacobbus spp.; Needle nematodes, Longidorus spp. such as L etongatus; Lesion nematodes, Pratytenchus spp. such as P. brachyurus, P. neglec- tus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopho/us spp. such as R. sim/l/s; Rhadopho/us spp.; Rhodopho!us spp.; Reniform nematodes, Roty/enchus spp. such as R. robustus, R. reniformis; Scutellonema spp.; Stubby-root nematode, Trichodorus spp. such as T. obtusus, T primitivus; Paratrichodorus spp. such as P. minor; Stunt nematodes, Tytencho- rhynchus spp. such as T daytoni, T dubius; Citrus nematodes, Tylenchulus spp. such as T. semipenetrans; Dagger nematodes, Xiphinema s p p .; a n d other plant parasitic nematode spe cies;

Insects from the order Isoptera for example Catotermes ftavicottis, Coptotermes spp. such as C. formosanus, C. gestroi, C. acinaciformis; Cornitermes cumutans, Cryptotermes spp. such as C. brevis, C. cavifrons; Giobitermes sulfureus, Heterotermes spp. such as H. aureus, H. tongiceps, H. tenuis; Leucotermes ftavipes, Odontotermes spp., tncisitermes spp. such as /. minor, i.

Snyder, Marginitermes hubbardi, Mastotermes spp. such as M. darwiniensis Neocapritermes spp. such as N. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. such as Z. angusticot/is, Z. nevadensis, Reticu/itermes spp. such as R. hesperus, R. tibialis, R. speratus, R. fiavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natatensis, Insects from the order Blattaria for example Btatta spp. such as B. orientatis, B. lateralis; Biattei- /aspp. such as B. asahinae, B. germanica; Leucophaea maderae, Panchiora nivea, Periplaneta spp. such as P. americana, P. austraiasiae, P. brunnea, P. fuligginosa, P. japonica; Supeiia longipalpa, Parcoblatta pennsyivanica, Eurycotis floridana, Pycnosce/us surinamensis,

Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Ctenocephalides spp. such as C. feiis, C. canis, Xenopsylla cheopis, Puiex irritans, Tricho- dectes canis, Tunga penetrans, and Nosopsy/lus fasciatus,

Insects from the order Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Thermobia domestica,

Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,

Pests from the class Diplopoda for example Blaniulus guttulatus, Ju/us spp., Narceus spp.,

Pests from the class Symphyla for example Scutigerella immacu/ata,

Insects from the order Dermaptera, for example Forficula auricularia,

Insects from the order Collembola, for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus ase/lus, Porcellio scaber,

Insects from the order Phthiraptera, for example Damaiinia spp., Pediculus spp. such as Pe- diculus humanus capitis, Pediculus humanus corporis, Pediculus humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus suis, Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and So/enopotes capillatus, Trichodectes spp.,

Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dreissena spp.; class Gastropoda, for example, Arion spp., Biomphaiaria spp. , Bu/inus spp., Deroceras spp., Gaiba spp., Lymnaea spp., Oncome/ania spp . , Pomacea canaliclata, Succinea spp. /from the class of the helminths, for example, Ancylostoma duodenaie, Ancyiostoma ceyianicum, Acylostoma brazHiensis, Ancy- lostoma spp., Ascaris lubricoides, Ascaris spp., Brugia maiayi, Brugia timori, Bunostomum spp., Chabertia spp., C/onorchis spp., Cooperiaspp., DicrocoeHum spp., Dictyocaulus fi/aria, Diphyi- lobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus muitiiocu- iaris, Enterobius vermicu/aris, Facioia spp., Haemonchus spp. such as Haemonchus contortus; Heterakis spp., Hymenolepis nana, Hyostrong ulus spp., Loa Loa, Nematodirus spp., Oesoph- agostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongy!oides stercora /is, Stronyioides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichineiia nativa, Trichineiia britovi, Trichi- neiia neisoni, Trichineiia pseudopsiraiis, Trichostronguius spp., Trichuris trichuria, Wuchereria bancrofti.

In another embodiment of the invention, further examples of resistant pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroas- ca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes terminife- ra, Cnaphalocroci medinalis, Cnaphalocrosis spp., Colias eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus maidis, Deraceras reticulatum , Diatrea saccharalis, Dichelops furcatus, Dicladispa armigera , Diloboderus spp. such as Dilobo- derus abderus; Edessa spp., Epinotia spp., Formici-dae, Geocoris spp., Globitermes sulfureus, Gryllotalpidae, Flalotydeus destructor, Hipnodes bicolor, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia orato-rius , Liogenys fuscus, Lucillia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma-rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, Microtheca spp., Mocis latipes, Murgantia spp., Mythemina separata , Neocapritermes opacus, Neocapritermes parvus, Neomegalotomus spp., Neotermes spp., Nymphula depunctalis, Oebalus pugnax, Orseolia spp. such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plusia spp., Pomacea canaliculata, Procornitermes ssp, Procornitermes triacifer , Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris cas- tanea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga inno- tata; Scotinophara spp. such as Scotinophara coarctata; Sesamia spp. such as Sesamia infe- rens, Sogaella frucifera, Solenapsis geminata, Spissistilus spp., Stalk borer, Stenchaetothrips biformis, Steneotarsonemus spinki, Sylepta derogata, Telehin licus, Trichostrongylus spp..

In another embodiment, the methods of the invention are particularly applicable to the control of resistant insects (and resistance in insects) of the family Aphididae, such as: Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangu-lae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus heli- chrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Erio- soma lanigerum, Hyalopterus pruni, Li-paphis erysimi, Macrosiphum avenae, Macrosiphum eu- phorbiae, Macrosiphum rosae, Myzus cerasi F., Myzus nicotianae, Myzus persicae, Nasonovia ribisnigri, Pemphigus bursarius, Phorodon humuli, Rhopalosiphum insertum Wa, Rhopalo- siphum Aidis Fitch, paddy L Rhopalosiphum, Schizaphis graminum Rond., Sitobion avenae, Toxoptera aurantii, Toxoptera citricola, Phylloxera vitifoliae, Acyrthosiphon dirhodum, Acyrthosi- phon solani, Aphis forbesi, Aphis grossulariae, Aphis idaei, Aphis illinoisensis, Aphis maidiradi- cis, Aphis ruborum, Aphis schneideri, Brachycaudus persicaecola, Cavariella aegopodii Scop., Cryptomyzus galeopsidis, Cryptomyzus ribis, Hyadaphis pseudobrassicae, Hyalopterus amyg- dali, Hyperomyzus pallidus, Macrosiphoniella sanborni, Metopolophium dirhodum, Myzus ma- lisuctus, Myzus varians, Neotoxoptera sp, Nippolachnus piri Mats., Oregma lanigera Zehnter, Rhopalosiphum fitchii Sand, Rhopalosiphum nymphaeae, Rhopalosiphum saccharata that, Sappaphis piricola ln-stant. + T, Schizaphis piricola, Toxoptera Sch theobromae, and Phylloxera coccinea.

In another embodiment, the methods of the invention are particularly applicable for the control of neonicotinoid resistant insects (and the neonicotinoid resistance in such insects) of these families.

Specific examples of neonicotinoid resistant aphids include Acyrthosiphum pisum, Aphis citrico la, Aphis craccivora, Aphis fabae, Aphis frangulae, Aphis glycines, Aphis gossypii, Aphis na- sturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hy alopterus pruni, Lipaphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae,

Macrosiphum rosae, Myzus cerasi F., Myzus nicotianae, Myzus persicae, Nasonovia ribisnigri, Pemphigus bursarius, Phorodon humuli, Rhopalosiphum insertum Wa, Rhopalosiphum Aidis Fitch, Rhopalosiphum padi L, Schizaphis graminum Rond., Sitobion avenae, Toxoptera au rantii, Toxoptera citricola, and Phylloxera vitifoliae.

In another embodiment of the invention, a resistant aphid controlled by the compound of the invention is also resistant to pyrethroid insecticides, such as Lambda-cyhalothrin. Thus, the in sect may be resistant to neonicotionid insecticide and/or pyrethroid insecticides.

In one embodiment, the method of invention is particularly useful for controlling chewing-biting pests, in particular insects from the order of Lepidoptera and Coleoptera, which method com prises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.

In one embodiment, the method of invention is particularly useful for controlling sucking or pierc ing insects, in particular insects from the order Diptera, , which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a ste reoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecticide, towards which insects are resistant, to said resistant insects.

In another embodiment of the invention, the insecticide resistant insect is from the order Lepi doptera and is selected from Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatah^'s, Argyresthia conjugella, Autographa gamma , Bupa!us piniarius, Cacoecia murinana, Capua reticu!ana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidenta!is, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiose /- la, Earias insuiana, Elasmopalpus iignose/ius, EupoeciHa ambiguella, Evetria bou/iana, Fe!tia subterranea, Galleria mellonella, Grapho/itha funebrana, Grapho/itha molesta, Heh^'othis armige- ra, Heliothis virescens, Heliothis zea, Hellula unda!is, Hibernia defoiiaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia iycopersiceiia, Lambdina fisceiiaria, Laphygma exigua, Leu- coptera coffeeiia, Leucoptera sciteiia, Lithocoiietis biancardeiia, Lobesia botrana, Loxostege stictica/is, Lymantria dispar, Lymantria monacha, Lyonetia cierkeiia, Maiacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubiiaiis, Panoiis fiammea, Pectinophora gossypieiia, Peridroma saucia, Phaiera bucephaia, Phthorimaea opercuieiia, Phyiiocnistis citrei- ia, Pieris brassicae, Piathypena scabra, Piuteiia xyiosteiia, Pseudopiusia inc/udens, Rhyacionia frustrana, Scrobipaipuia absoiuta, Sitotroga cereaieiia, Sparganothis pWeriana, Spodoptera fru- giperda, Spodoptera iittoraiis, Spodoptera iitura, Thaumatopoea pityocampa, Tortrix viridana, Trichopiusia /7/and Zeiraphera canadensis.

In another embodiment of the invention, the insecticide resistant insect is from the order Cole- optera (beetles) and is selected from Agri/us sinuatus, Agriotes iineatus, Agriotes obscurus, Amphimaiius so/stitia/is, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aph- thona euphoridae, Athous haemorrhoidaiis, Atomaria linearis, Biastophagus piniperda, Biitoph- aga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betuiae, Cassida nebuiosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimi/is, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Dia- brotica iongicornis, Diabrotica semi punctata, Diabrotica 12-punctata Diabrotica speciosa, Dia- brotica virgifera, Epiiachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiiiensis, Hyiobius abietis, Hypera brunneipennis, Hypera postica, ips typographus, Lema biiineata, Lema meiano- pus, Leptinotarsa decemiineata, Limonius caiifornicus, Lissorhoptrus oryzophiius, Meianotus communis, Meiigethes aeneus, Meioiontha hippocastani, Meioiontha meioiontha, Ouiema ory- zae, Otiorrhynchus su/catus, Otiorrhynchus ovatus, Phaedon cochieariae, Phyiiobius pyri, Phyi- iotreta chrysocephaia, Phyiiophaga sp., Phyiiopertha horticoia, Phyiiotreta nemorum, Phyiiotreta strioiata, PopiHia japonica, Sitona iineatus and Sitophi/us granaria.

In one embodiment, the method of invention is particularly useful for controlling the insecticide resistant insect is a potato beetle, more specifically the Colorado potato beetle, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibi tor and the insecticide, towards which insects are resistant, to said resistant insects.

In another embodiment of the invention, the insecticide resistant insect is from the order Diptera and is selected from Aedes aegypti, Aedes aibopictus, Aedes vexans, Anastrepha iudens, Anopheles macuiipennis, Anopheles crucians, Anopheles aibimanus, Anopheles gambiae, Anopheles freeborni, Anopheles ieucosphyrus, Anopheles minimus, Anopheles quadrimacuia- tus, Caiiiphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya maceiiaria, Chrysops discalis, Chrysops siiacea, Chrysops atianticus, Cochiiomyia hominivorax, Contarinia sorghicoia Cordyiobia anthropophaga, Cu/icoides furens, Cuiex pipiens, Cuiex nigripaipus, Cuiex quinquefasciatus, Cuiex tarsaiis, Cuiiseta inornata, Cuiiseta meianura, Dacus cucurbitae, Dacus oieae, Dasineura brassicae, Delia antique, Delia coarctata, Delia pia- tura, Delia radicum, Dermatobia hominis, Fannia canicuiaris, Geomyza Tripunctata, Gasterophi- ius intestina/is, G/ossina morsitans, Glossina pa/pa/is, G/ossina fuscipes, G/ossina tachinoides, Haematobia irritans, Hap/odip/osis equestr/s, Hippe/ates spp., Hy/emyia p/atura, Hypoderma Hneata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifo/ii, Luci/ia caprina, Lucih^'a cu- prina, Luci/ia sericata, Lycoria pectora/is, Mansonia tit/Hanus, Mayetio/a destructor, Musca au- tumna/is, Mu sc a domestic a, Muscina stabuians, Oestrus ovis, Opomyza fiorum, Oscineiia frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phiebotomus ar- gentipes, Psorophora coiumbiae, Psiia rosae, Psorophora discolor, Prosimuiium mixtum, Rhag- oietis cerasi, Rhagoletis pomoneiia, Sarcophaga haemorrhoidaiis, Sarcophaga spp., Simulium vittatum, Stomoxys caicitrans, Tabanus bovinus, Tabanus atratus, Tabanus iineoia, and Taba- nus simi/is, Tipuia oieracea, and Tipuia paiudosa.

In one embodiment, the method of invention is particularly useful for controlling the insecticide resistant insect is selected from thrips, hoppers and whitefly, which method comprises applying a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the insecti cide, towards which insects are resistant, to said resistant insects.

In particular, in the methods and uses according to the invention, the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Spodoptera littoralis, Spodoptera frugiperda, Crocidolomia pavonana, Cnaphalocerus medinalis, Sesamia inferens, Chilo suppressalis, Pyrausta furnacalis, Thermesia gemmatalis, Liriomyza sp., Lep- tinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Meligethes aeneus, Hypera brun- neipennis; Nilaparvata lugens, Nephotettix virens; Acyrthosiphum pisum, Bemisia tabaci, Be- misia argentifolii, Euschistus heros, Nezara viridula, Piezodurus guildingi, Lygus hesperus, thrips spp., Frankliniella occidentalis; Agriothes sp., Agrotis ypsilon, Phyllotreta spp. Cydia po moneiia, Elasmopalpus lignosellus, Heliothis armigera, Heliothis virescens, Heliothis zea; Agri- otes lineatus, Agriotes obscurus,, Anthonomus grandis, Diabrotica longicornis, Diabrotica semi- punctata, Diabrotica 12-punctata, Diabrotica speciosa, Diabrotica virgifera, Epitrix hirtipennis, Phaedon cochlearieae, Phyllotreta striolata.

In particular, in the methods and uses according to the invention, the insecticide resistant insect is one or more of Tuta absoluta, Pieris rapae, Trichoplusia ni, Plutella xylostella, Chilo suppres salis, Liriomyza sp., Leptinotarsus decemlineata, Epitrix sp., Phyllotreta cruciferae, Franklinella occidentalis, Bemisia tabaci, Bemisia argentifolii, Agrotis ypsilon.

In particular, in the methods and uses according to the invention, the insecticide resistant insect is one or more of Agrotis ypsilon, Heliothis virescens, Plutella xylostella, Agriotes lineatus, Dia brotica virgifera, Hypera brunneipennis, Leptinotarsus decemlineata, Phyllotreta striolata.

Method of controlling insecticide resistant non-crop pests

In one embodiment, the invention relates to a method for controlling or combating non-crop pests, which are resistant to an insecticide, comprising applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta- ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop pests are resistant.

In one embodiment, the invention relates to a method for controlling or combating non-crop pests, which are resistant to an insecticide, comprising applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop pests are resistant.

In another embodiment, the invention further relates to the use of compounds of formula (I) as P450 inhibitor for the protection of non-living organic materials against non-crop pests.

In one embodiment, the invention provides the method of controlling resistance to one or more insecticides in non-crop pests, which comprises alternately or simultaneously applying com pound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop pests are resistant, to said non-crop pests or to a crop of useful plants susceptible to and/or under attack from said non crop pests.

In another embodiment, the invention provides the method wherein the resistant non-crop pests developed resistance against insecticides selected from avermectins, milbemycins, cyclodienes, phosphines, carbamates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, be- ta-ketonitrile derivatives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acari- cides, insect growth regulators or antifeedants.

In one embodiement, the invention provides the method for controlling or combating non-crop pests, which are resistant to an insecticide, comprises applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) as cytochrome P450 inhibitor and the insecticide, towards which non crop pests are resistant.

In preferred embodiment, the non-crop pests, which are resistant to an insecticide, are pests of the classes Chilopoda and Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthop- tera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.

In another embodiment, the present invention provides a method for controlling or combating following non-crop pests, which are resistant to an insecticide:

centipedes (Chilopoda), e.g. Scutigera coleoptrata,

millipedes (Diplopoda), e.g. Narceus spp.,

spiders (Araneida), e.g. Latrodectus mactans, and Loxosceles reclusa,

scabies (Acaridida): e.g. sarcoptes sp,

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocy- clus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor vari- abilis, Amblyomma americanum, Ambryomma maculatum, Orni- thodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Orni- thonyssus bacoti and Dermanyssus galli- nae, termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Re- ticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus,

cockroaches (Blattaria - Blattodea), e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta aus- tralasiae, and Blatta orientalis,

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anatrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus,

Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hom- inis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hip- pelates spp., Hypoderma lineata, Lep- toconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia se cata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar- gentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarco- phaga haemorrhoidalis, Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Ta- banus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis,

Earwigs (Dermaptera), e.g. forficula auricularia,

true bugs (Hemiptera), e.g. Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius prolixus, and Arilus critatus,

ants, bees, wasps, sawflies (Hymenoptera), e.g. Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis geminata, Sole- nopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogo- nomyrmex californicus, Dasymutilla occidentalis, Bombus spp. Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula maculata, Vespa crabro, Polistes ru- biginosa, Camponotus floridanus, and Li- nepithema humile,

crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca ameri cana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Callip- tamus italicus, Cho oicetes terminifera, and Locustana pardaliria,

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi- rus pu bis, Haematopinus eurystemus, Haematopinus suis, Linognathus vituli, Bovlcola bovis, Meno- pon gallinae, Menacanthus stramineus and Solenopotes capillatus. The hydrazine derivatives of formula (I) which can be used according to the invention are known from and can be prepared according to preparation methods described or referenced in EP-A 604 798. This document relates to plant protection in the agricultural field and discloses the insecticidal and acaricidal activity of compounds of fomula I and other compounds against crop pests of the Coleoptera, Lepidoptera and Acarina orders.

In preferred embodiment, the invention provides the method of controlling non-crop pests, which are resistant to an insecticide, wherein non-crop pests are pests of the classes Chilopoda and Dilopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hy- menoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.

In one embodiment, the invention provides a method, which process comprises treating the non-crop insect, which are resistant to an insecticide, the plant, or the plant propagation materi al selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants to be protected against non-crop pest attack, the stored materials or harvest, or alternately, the locus or soil or soil sub stituents or surfaces therefrom, with an effective amount of at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tau tomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.

In yet another embodiment of the present invention relates to a method of controlling resistance to one or more insecticides in non-crop pests, wherein the resistant non-crop pests developed resistance against against following insecticides:

The following list M of pesticides, grouped and numbered according the Mode of Action Clas sification of the Insecticide Resistance Action Committee (IRAC), together with which the com pounds of the invention can be used and with which potential synergistic effects might be pro duced, is intended to illustrate the possible combinations, but not to impose any limitation:

M.1 Acetylcholine esterase (AChE) inhibitors: M .1 A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxam-yl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyri- fos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicroto- phos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenami- phos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimi- phos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; MAC sulfoxaflor; MAD flupyradifurone; MAE triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide; M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, M .20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M .21A METI acaricides and in- sec-ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-'ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-'methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-ylJcarbonyl^aminoJbenzoyll-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-Oarbamoyll-phenyll^-iS-chloro^-pyridy -S-itrifluoromethy pyrazole-S- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylideneJcarbamoylJ-phenyl^-iS-chloro^-pyridy -S-itrifluoro-Tnethy pyrazole-S- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- noTnethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 ,4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine ; M .UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN.9.b): fluxametamide ; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.b) 3-(benzoylmethylannino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11 .c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M .U N .1 1.d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;

M . U N .1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;

M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)-^,ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S-^^-iodo^-ll ^^^-tetrafluoro-l-itrifluoromethy -'ethyll-e-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.UN.1 1.i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 .j) 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethyO^propylJphenylJ^-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; M.UN.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;

M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ^^^-tetrafluoro-l-Ctrifluoromethy ethyllphenyllcarbamoylJ-'phenyll^-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M .U N .12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5- yl]pyridine-2-carboxamide; M.U N.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide ; M.UN.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN .12.g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .UN.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio- propanamide; M .U N .12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N ,2-dimethyl-3-methylthio- propanamide; M . U N.12.1) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M.UN.12.m) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-ethyl-3-methylthio- propanamide ;

M. UN.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;

M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; M.UN.16e) N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.UN.16†) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M .UN.16g) 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide; M .U N .16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.U N.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide,

M. UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17c) N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M. UN.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide; M. UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide; M. UN.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M .U N .18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;

M.UN.19 sarolaner , M.UN.20 lotilaner ;

M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 , 1 ,2, 2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ; M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;

M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazole-3-carboxamide ; M.UN.25 acynonapyr ; M.UN.26 benzpy-rimoxan ; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide .

The commercially available compounds of the group M listed above may be found in The Pes ticide Manual, 17th Edition, C. MacBean, British Crop Protection Council (2015) among other publications. The online Pesticide Manual is updated regularly and is accessible through https://bcpcdata.com/pesticide-manual.html.

Another online data base for pesticides providing the ISO common names is

https://www.alanwood.net/pesticides.

The M.4 cycloxaprid is known from WO2010/069266 and WO201 1/069456. M.4A.1 is known from CN 103814937; CN 105367557, CN 105481839. M .4A.2, guadipyr , is known from WO 2013/003977, and M.4A.3 (approved as paichongding in China) is known from WO

2007/101369. M.22B.1 is described in CN 10171577 and M .22B.2 in CN 102126994. Spiropidion M.23.1 is known from WO 2014/191271. M.28.1 and M.28.2 are known from W02007/101540. M.28.3 is described in W02005/077934. M.28.4 is described in W02007/043677. M .28.5a) to M.28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and WO

2013/024010, M.28.5i) is described in WO2011/085575, M.28.5j) in W02008/134969, M.28.5k) in US2011/046186 and M .28.5I) in WO2012/034403. M.28.6 can be found in WO2012/034472. M.UN.3 is known from W02006/089633 and M.UN.4 from W02008/067911. M .UN.5 is de- scrhbed in W02006/043635, and biological control agents on the basis of bacillus firmus are described in W02009/124707. Flupyrimin is described in WO2012/029672. M.U N.8 is known from WO2013/055584. M.UN.9.a) is described in WO2013/050317. M.UN.9.b) is described in WO2014/126208. M. UN.10 is known from WO2010/060379. Broflanilide and M.UN.H .b) to M.UN.1 1.h) are described in W02010/018714, and M.UN.11 i) to M.UN.1 1 .p) in WO

2010/127926. M.UN.12.a) to M.UN.12.C) are known from WO2010/006713, M .UN.12.d) and M.UN.12.e) are known from WO2012/000896, and M.UN.12.f) to M.UN.12.m) from WO 2010/129497 . M. UN.14a) and M. UN.14b) are known from W02007/101369. M.UN.16.a) to M.UN.16h) are de-scribed in WO2010/034737, WO2012/084670, and WO2012/143317, resp., and M.UN.16i) and M.UN.16j) are described in WO2015/055497. M. UN.17a) to M.UN.17 ) are described in WO2015/038503. M.UN.18a) to M.UN.18d) are described in US2014/0213448. M.UN.19 is de-scribed in WO2014/036056. M. UN.20 is known from WO2014/090918. M.UN.21 is known from EP2910126. M. UN.22a and M. UN.22b are known from WO2015/059039 and W02015/190316. M.UN.23a and M.UN.23b are known from WO2013/050302. M .UN .24a and M. UN.24b are known from WO2012/126766. Acynonapyr M.U N.25 is known from WO

201 1/105506. Benzpyrimoxan M.UN.26 is known from W02016/104516. M.UN.27 is known from WO2016174049.

In another embodiment of the invention, in the methods and uses according to the invention, the non-crop pest, which are resistant to insecticide, is selected from flies, mosquitoes (Diptera).

In yet another embodiment, the invention relates to the method of controlling resistance to one or more insecticides in non-crop pests, which comprises applying compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which the non-crop pests are resistant, to said non-crop pests pref erably selected from flies and mosquitoes. More preferably, the non-crop pest is selected from: Aedes aegypti, Aedes albopictus, Aedes vexans, Anas- trepha ludens, Anopheles maculi- pennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadhmaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inor- nata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intes- tinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Lep- to- conops torrens, Lucilia caprina, Lucilia cuprina, Lucilia se cata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus ar- gentipes, Psoropho- ra columbiae, Psorophora discolor, Prosimulium mixtum, Sarco- phaga haemorrhoidalis, Sar- cophaga sp., Simulium vittatum,Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Taba- nus lineola, and Tabanus si.

In another embodiment of the invention, in the methods and uses according to the invention, the non-crop pest, which are resistant to insecticide, is selected from termites (Isoptera). More pref erably, the non-crop pest, which are resistant to insecticide, is selected from: Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus.

In one embodiment, the invention relates to a method for controlling resistance in non-crop pest, which are resistant to insecticide, is selected from termites, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.

In another embodiment of the invention, in the methods and uses according to the invention, the non-crop pest, which are resistant to insecticide, is selected from ants (Hymenoptera). More preferably, the non-crop pest, which are resistant to insecticide, is selected from: Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Monomo urn pharaonis, Solenopsis gemi- nata, Sole- nopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Po- go-nomyrmex californicus, Dasymutilla occidentalis, Bombus spp. Vespula squamosa, Para- vespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolicho- vespula macu- lata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile.

In one embodiment, the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from ants, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant.

In another embodiment of the invention, in the methods and uses according to the invention, the non-crop pest, which are resistant to insecticide, is selected from crickets, grasshoppers, lo custs (Orthoptera). More preferably, the non-crop pest, which are resistant to insectide, is se lected from: Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivitta- tus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca ame-ricana, Schistocerca gregaria, Doci- ostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Callip-tamus italicus, Chooicetes terminifera, and Locustana pardaliria.

In one embodiment, the invention relates to a method for controlling or combating non-crop pest, which are resistant to insecticide, is selected from crickets, grasshoppers, locusts (Orthop- tera), which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, to wards which insects are resistant.

Therefore, in another embodiment, the invention relates to the method according to the inven tion, wherein the non-crop pest is selected from flies, mosquitoes (Diptera).

Netting or textile material, impregnated with a compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, to wards which insects are resistant, as defined herein. Method according to the invention, wherein stored products are protected from pests, especially a method according to the inven tion, wherein the stored product is selected from tobacco, nuts, cocoa, fruits, wood.

Method according to the invention, wherein the stored product is protected by a netting or textile material, impregnated with a compound of formula (I) in free form or in the form of a stereoiso mer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S- oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non crop insects are resistant, as defined herein.

In an embodiment, the method or use of a compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, as defined herein, or a composition comprising said compound of formula (I) ,

for controlling non-crop pests, and/or

for controlling flies, mosquitoes (Diptera), and/or

for protecting stored products, and/or

for protecting stored tobacco, nuts, cocoa, fruits, wood.

In a preferred embodiment of the present invention, the compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an iso topic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, and compo sitions comprising them, are used for the protection of non-living organic materials, including but are not limited to house-hold goods such as fats, oils, mono- oligo- or polyorganosaccharides, proteins, or fresh or decaying fruits; cellulose-containing materials e.g. wooden materials such as houses, trees, board fences, or sleepers and also paper; and also construction materials, furniture, leathers, animal, plant and synthetic fibers, vinyl articles, electric wires and cables as well as styrene foams.

More preferably, method or use of compounds of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N- oxide, a S-oxide, a derivative or a mixture thereof, and compositions comprising them, for the protection of non-living organic materials against non-crop pests selected from the group con sisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermap- tera, Hemiptera, Hymenoptera, Orthoptera, and Thysanura. Most preferably, the invention relates to use of compounds of formula (I) according to the inven tion, for the protection of human beings and animals against mosquitos. In this respect, the in vention especially relates to textile materials, foils or nettings which comprise or incorporate a compound according to the invention in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which mosquitos are re sistant. In one aspect, "incorporated" means embedded. In another aspect, "incorporated" means comprised in impregnated form.

The invention also relates to above-mentioned textile material for the protection of plants or crops, e.g. tobacco, nuts, fruits, trees, wood.

The foils or nettings can also be used as mulch foil in the protection of crops.

Furthermore, there is a broad use of the compounds of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor according to the invention and the insecticide, towards which non-crop insects are resistant, e.g. for protecting stored goods in a container as described e.g. in W02013/000907.

In one embodiment, the invention relates to a netting, which comprises use of compound of formula I in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor.

In one embodiment, the invention relates to a method for protecting humans from insects, which are resistant to insecticides, which method comprises applying the compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop insects are resistant.

In one embodiment, the invention relates to a method for protecting stored goods from non-crop insects, which are resistant to insecticide, whichmethod comprises applying the compound of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant. In preferred embodiment, the invention relates to a method for protecting stored goods which are selected from tobacco, nuts, cocoa, fruits, wood; which method comprises applying a compound of for mula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.

The present invention also relates to a method for the protection of non-living organic materials against non-crop pests, which are resistant to insecticides, preferably against non-crop pests selected from the group consisting of the class Diplopoda and of the orders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, and Thysanura, com prising contacting the pests or their food supply, habitat, breeding grounds, their locus or the non-living organic materials themselves with at least one compound of formula (I) in the free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in the free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.

Moreover, compounds of formula (I) in the free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an iso topic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the in secticide, towards which non-crop insects are resistant, are preferably used for protecting cellu lose-containing non-living organic materials:

Preferably, compounds of formula (I) in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the insecticide, towards which non-crop insects are resistant, are used for protecting cellulose-containing non-living organic materials against resistant non-crop pests from the Isoptera, Diptera, Blattaria (Blattodea), Hy- menoptera, and Orthoptera orders, most preferably the Isoptera orders.

The present invention also provides a method for protecting cellulose-containing non-living or ganic materials against non-crop pests, which are resistant to insecticides, preferably from the Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, and Orthoptera orders, most preferably the Isoptera orders, comprising contacting the pests or their food supply, habitat, breeding grounds, their locus or the cellulose containing non-living organic materials themselves with at least one of a compound of formula (I) in free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an iso topic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the in secticide, towards which non-crop insects are resistant.

In one embodiment of the present invention, use of compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor, or a composition comprising it, are used for protecting mono- oligo- or polysaccharides and proteins.

Preferably, use of compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof, or a composition comprising it, as p450 inhibitors, for protecting mono- oligo- or polysaccharides and proteins against non-crop pests selected from the Dermap- tera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hymenoptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blattodea), and Hymenoptra orders. In one embodiment, the present invention also provides a method for protecting mono- oligo- or polysaccharides and proteins against non-crop pests, which are resistant to insecticides, pref erably selected from the Dermaptera, Diplopoda, Isoptera, Diptera, Blattaria (Blattodea), Hyme- noptera, Orthoptera and Tysanura orders, most preferably the Isoptera, Diptera, Blattaria (Blat todea), and Hymenoptra orders, comprising contacting the pests or their food supply, habitat, breeding grounds or their locus with at least one compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecti cide, towards which non-crop insects are resistant , or a composition comprising at least one compound of formula (I), in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant.. Furthermore, compounds of formula (I) in free form or in the form of a stereoisomer, an agricul turally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a deriva tive or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant, or a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecti cide, towards which non-crop insects are resistant, are preferably used for protection of animals against non-crop pest, which are resistant towards insecticides, of the class Chilopoda, and of the orders Araneida, Hemiptera, Diptera, Phthiraptera, Siphonaptera, Parasitiformes and Acaridida by treatment of the pests in water bodies and / or in and around buildings, including but not limited to walls, ground, manure piles, turf grass, pastures, sewers and materials used in the construction of buildings and also mattresses and bedding. Most preferably, compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which non-crop insects are resistant, are used for protection of animals against resistant non-crop pest of the Diptera, Phthiraptera, Siphonaptera, and Parasitiformes orders.

Animals include warm-blooded animals, including humans and fish. Compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor are preferably used for protection of warm-blooded animals such as cattle, sheep, swine, cam els, deer, horses, poultry, rabbits, goats, dogs and cats.

Formulations

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of formula (I) of the present invention or a mixture thereof.

The compounds of formula (I) of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composi-tion types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further compositions types are de fined in the“Catalogue of pesticide formulation types and international coding system”, Tech nical Mono-graph No. 2, 6th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Examples for suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive col loids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil frac tions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclo-'hexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. am monium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective col loid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1 : Emulsifiers & De tergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyhnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox ylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Exam- pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth oxy I ates.

Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam ples of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or al- kylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinyl pyrrol i- done, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or pol- yethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present invention on the target. Examples are surfactants, mineral or vegetable oils, and other auxi- laries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorgan-ic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, pol yacrylates, biological or synthetic waxes, and cellulose ethers.

In one embodiment, the present invention relates to the agrochemical compositions comprising at least one P450 inhibitor compound of formula (I) may be combined/mixed with the pre prepared formulation of an active ingredient, for example, insecticide. In preferred embodiment, the present invention relates to the agrochemical compositions comprising at least one com pound of formula (I) as P450 inhibitor and pre-prepared formulation of at least one insecticide.

In another embodiment, the present invention provides the agrochemical compositions compris ing at least one compound of formula (I) as P450 inhibitor and at least one active ingredient, for example, insecticide.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi ately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 : 100 to 100: 1 , preferably 1 : 10 to 10: 1 .

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound of formula (I) and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to 100 wt%. The ac tive substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound of formula (I) and 1-10 wt% dispersant (e. g. polyvi-nylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound of formula (I) and 5-10 wt% emulsifiers (e.g. calcium dodecylben- zenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt% of a compound of formula (I) and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzene- sulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into up to 100 wt% water by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.

v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound of formula (I) are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substances. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound of formula (I) are ground finely with addition of up to 100 wt% disper sants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substances. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of a compound of formula (I) are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dispersion or solu tion of the active substances.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound of formula (I) are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. car- boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub stance. Dilution with water gives a stable suspension of the active substances.

ix) Microemulsion (ME)

5-20 wt% of a compound of formula (I) are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alko-hol ethoxylate and arylphenol ethoxylate), and water up to 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound of formula (I), 0-40 wt% water insoluble or ganic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacry late, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protec tive colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5- 50 wt% of a compound of formula (I) and optionally active compound selected from insecticide, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate mon omer (e.g. diphenylme-thene-4,4’-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenedia- mine) results in the formation of a polyurea microcapsule. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS)

1-10 wt% of a compound of formula (I) are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.

xii) Granules (GR, FG)

0.5-30 wt% of a compound of formula (I) is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.

xiii) Ultra-low volume liquids (UL)

1-50 wt% of a compound of formula (I) are dissolved in up to 100 wt% organic solvent, e.g. ar omatic hydrocarbon.

The compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1 -1 wt% col orants.

The agrochemical compositions generally comprise between 0.01 and 95%, preferably be tween 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active substances. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemi cal composition is made up with water, buffer, and/or further auxiliaries to the desired applica tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the in vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in vention or partially premixed components, e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined below, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in vention or partially premixed components, e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

In the methods and/or uses according to the invention, the application of the the compounds of formula (I) of the present invention, or an acceptable salt, an isotopic form, a derivative or mix ture thereof, is preferably as explained in the following.

The animal pest (also referred to as "invertebrate pest"), i.e. the insects, arachnids and nema todes, can be contacted with the present compounds of formula (I) or composition(s) comprising them by any application method known in the art. As such, "contacting" includes both direct con tact (applying the compounds/compositions directly on the animal pest and indirect contact (ap plying the compounds/compositions to the locus of the animal pest).

The compounds of the present invention are employed in form of compositions by treating the insects’ surfaces, materials or rooms to be protected from insecticidal attack with an insecticidal- ly effective amount of the insecticide towards which insects are resistant. The application can be carried out both before and after the infection of the surfaces, materials or rooms by the insects.

The present invention also includes a method of combating or controlling animal pests which comprises contacting the animal pests, which are resistant towards insecticides, their habitat, breeding ground, food supply, area, material or environment in which the animal pests are growing or may grow, or the materials, surfaces or spaces to be protected from animal attack or infestation with at least one compound of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which animal pests are resistant.

Moreover, animal pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with an effective amount of compounds of formula (I) or an ac ceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecti cide, towards which target pests are resistant. As such, the application may be carried out be fore or after the infection of the locus by the pest.

The compounds of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which non-crop insects are resistant, can also be applied preventively to places at which occurrence of the resistant pests are expected.

"Locus" means a habitat, breeding ground, area, material or environment in which a pest or parasite is growing or may grow.

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compounds per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .

The compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an iso topic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant.

The compounds of formula (I) are effective through both contact (via glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part).

For use against non-crop pests, which are resistant towards insecticide, compounds of formula (I) or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistant, are preferably used in a bait composition.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). Solid baits can be formed into various shapes and forms suitable to the respective application e.g. granules, blocks, sticks, disks. Liquid baits can be filled into various devices to ensure proper application, e.g. open containers, spray devices, droplet sources, or evaporation sources. Gels can be based on aqueous or oily matrices and can be formulated to particular necessities in terms of stickyness, moisture retention or aging characteristics.

The bait employed in the composition is a product, which is sufficiently attractive to incite in sects such as ants, termites, wasps, flies, mosquitos, crickets etc. or cockroaches to eat it. The attractiveness can be manipulated by using feeding stimulants or sex pheromones. Food stimu'ants are chosen, for example, but not exclusively, from animal and/or plant proteins (meat-, fish- or blood meal, insect parts, egg yolk), from fats and oils of animal and/or plant origin, or mono-, oligo- or polyorganosaccharides, especially from sucrose, lactose, fructose, dextrose, glucose, starch, pectin or even molasses or honey. Fresh or decaying parts of fruits, crops, plants, animals, insects or specific parts thereof can also serve as a feeding stimulant.

Sex pheromones are known to be more insect specific. Specific pheromones are described in the literature and are known to those skilled in the art.

For use in bait compositions, the typical content of at least one compound of formula (I) of the invention or an acceptable salt, stereoisomers, an isotopic form, a derivative or mixture thereof and the insecticide, towards which pests are resistantis from 0.001 weight % to 15 weight %, desirably from 0.001 weight % to 5%.

In a preferred embodiment of the invention, in the methods and uses according to the invention, at least one compound of formula (I) in free form or in the form of a stereoisomer, an agricultur ally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof, are present in the formulation form of an aerosol.

Formulations of compounds of formula (I) in free form or in the form of a stereoisomer, an agri culturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a de rivative or a mixture thereof f as P450 inhibitor and the insecticide, towards which pests are re sistant, as aerosols (e.g in spray cans), oil sprays or pump sprays are highly suitable for the professional and non-professional user for controlling pests, which are resistant towards insecti cide, such as flies, fleas, ticks, mosquitos or cockroaches. Aerosol recipes are preferably com posed of the active compounds, solvents such as lower alcohols (e.g. methanol, ethanol, pro panol, butanol), ketones (e.g. acetone, methyl ethyl ketone), paraffin hydrocarbons (e.g. ker osenes) having boiling ranges of approximately 50 to 250°C, dimethylformamide, N- methylpyrrolidone, dimethyl sulfoxide, aromatic hydrocarbons such as toluene, xylene, water, furthermore auxiliaries such as emulsifiers such as sorbitol monooleate, oleyl ethoxylate having 3-7 mol of ethylene oxide, fatty alcohol ethoxylate, perfume oils such as ethereal oils, esters of medium fatty acids with lower alcohols, aromatic carbonyl compounds, if appropriate stabilizers such as sodium benzoate, amphoteric surfactants, lower epoxides, triethyl orthoformate and, if required, propel'ants such as propane, butane, nitrogen, compressed air, dimethyl ether, carbon dioxide, nitrous oxide, or mixtures of these gases.

The oil spray formulations differ from the aerosol recipes in that no propellants are used. For use in spray compositions, the content of active ingredients is from 0.001 to 80 weights %, pref erably from 0.01 to 50 weight% and most preferably from 0.01 to 15 weight %.

The compounds of formula (I) and its respective compositions can also be used in mosquito and fumigating coils, smoke cartridges, vaporizer plates or long-term vaporizers and also in moth papers, moth pads or other heat-independent vaporizer systems. In one embodiment, the methods to control infectious diseases transmitted by insects (e.g. ma laria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with compounds of for mula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereofand the insecticide, towards which insects are resistant and its respective compositions also com prise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. The compositions for application to fibers, fabric, knitgoods, nonwovens, netting material or foils and tarpaulins preferably comprise at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant , op tionally a repellent and at least one binder. Suitable repellents for example are N, N-Diethyl- meta-toluamide (DEET), N.Ndiethylphenylacetamide (DEPA), 1-(3-cyclohexan-1-yl-carbonyl)-2- methylpiperine, (2-hydroxymethylcyclohexyl) acetic acid lactone, 2-ethyl-l ,3-hexandiol, inda- lone, Methylneodecanamide (M N DA), a pyrethroid not used for insect control such as {(+/-)-3- allyl-2-methyl-4-oxocyclopent-2-(+)-enyl-(+)-trans-chrysantemate (Esbiothrin), a repellent de rived from or identical with plant extracts like limonene, eugenol, (+)-Eucamalol (1), (-)-1 -epi- eucamalol or crude plant extracts from plants like Eucalyptus maculata, Vitex rotundifolia, Cymbopogan martinii, Cymbopogan citratus (lemon grass), Cymopogan nartdus (citronella). Suitable binders are selected for example from polymers and copolymers of vinyl esters of ali phatic acids (such as such as vinyl acetate and vinyl versatate), acrylic and methacrylic esters of alcohols, such as butyl acrylate, 2-ethylhexylacrylate, and methyl acrylate, mono- and di- ethylenically unsaturated hydrocarbons, such as styrene, and aliphatic diens, such as butadi ene.

The impregnation of curtains and bednets is done in general by dipping the textile material into emulsions or dispersions of the insecticide or spraying them onto the nets.

The compounds of formula (I) and its compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, which are resistant to insecticide, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities). The compounds of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as P450 inhibitor and the insecticide, towards which insects are resistant ,are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the ant controller of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like. Method of controlling herbicide resistant undesired vegetation

In one embodiment of the invention there is provided a method of controlling undesired vegeta tion, which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is resistant.

In one embodiment of the invention there is provided a method of controlling undesired vegeta tion, which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.

In one embodiment, the present invention provides a method of controlling undesired vegeta tion, which are resistant to an herbicide, which method comprises applying to undesired vegeta tion, which are resistant to an herbicide, a composition comprising at least one compound of formula (I) as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is resistant.

In one embodiment of the invention there is provided a method of controlling undesired vegeta tion, which are resistant to a herbicide, which method comprises applying to said herbicide re sistant undesired vegetation a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tauto mer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and the herbicide, towards which undesired vegetation is resistant.

In one embodiment of the invention there is provided a method of protecting a crop of useful plants susceptible to and/or under attack by undesired vegetation, which are resistant to a herb icide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said undesired vegetation, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vege tation is resistant.

In one embodiment of the invention there is provided a method of controlling resistance to one or more herbicides in undesired vegetation, which comprises alternately or simultaneously ap plying compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor, and the herbicide, towards which the undesired vegetation are resistant, to said undesired vegetation or to a crop of useful plants susceptible to and/or under attack from said undesired vegetation. In one embodiment of the invention there is provided a method of controlling undesired vegeta tion, which are resistant to a herbicide, which method comprises treating the undesired vegeta tion, the plant, or the plant propagation material selected from the group consisting of seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seed lings and young plants to be protected against undesired vegetation attack, the stored materials or harvest, or alternately, the locus or soil or soil substituents or surfaces therefrom, with at least one compound of formula (I) ) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one herbicide, towards which the un desired vegetation are resistant.

In another embodiment of the invention, the resistant undesired vegetation developed re sistance against herbicide selected from the following list of herbicides

b1 ) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

b9) mitosis inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11 ) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxinic herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;

including their agriculturally acceptable salts or derivatives;

and

C) safeners.

If the herbicidal compounds B and/or the safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.

If the herbicidal compounds B and/or the safeners C as described herein have one or more cen ters of chirality and, as a consequence, are present as enantiomers or diastereomers, it is pos- sible to use both, the pure enantiomers and diastereomers and their mixtures, in the composi tions according to the invention.

If the herbicidal compounds B and/or the safeners C as described herein have ionizable func tional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.

In yet another preferred embodiment, the herbicide to which the undesired vegetation are re sistant is from the following list of herbicides:

b1 ) from the group of the lipid biosynthesis inhibitors:

ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalo- fop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,

4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy-

2.2.6.6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'- Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2^',4'- dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5- (Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2^',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6- dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4- ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-

2.2.6.6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thio- bencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfu- ron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifen- sulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, tri- flusulfuron-methyl and tritosulfuron,

imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,

pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8),

sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;

among these, a preferred embodiment of the invention relates to those compositions comprising at least one imidazolinone herbicide;

b3) from the group of the photosynthesis inhibitors:

amicarbazone, inhibitors of the photosystem II, e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1 -(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1 -(5-tert-butyl-1-methyl- pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1 - methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4- hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8) , 1 -(5-tert-butyl isoxazol-3-yl)-4-ethoxy-5-hydroxy-3-m ethyl-i m idazol id i n-2-one (CAS 1844836-64-1), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, met- amitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phen- medipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibi tors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Among these, a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herb icide. Among these, likewise a preferred embodiment of the invention relates to those composi tions comprising at least one nitrile herbicide;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfen- trazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6- trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6; S-3100, N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 7-pyrazole- 1 -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4- trifluoromethylphenoxy)-5-methyl-1 /fpyrazole-1 -carboxamide (CAS 915396-43-9), N-ethyl-3-(2- chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 /-pyrazole-l -carboxamide (CAS 452099- 05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A/-pyrazole- 1 -carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2- (2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro- isoindole-1 ,3-dione (CAS 1300118-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4- prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05- 0), methyl (£)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1 /7-methyl-pyrazol-3-yl]-4-fluoro- phenoxy]-3-methoxy-but-2-enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2- (trifluoromethyl)-l H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);

b5) from the group of the bleacher herbicides:

PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71-0), 2-(2,4-dichlorophenyl)methyW,4- dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3- isoxazolidinone (CAS 81778-66-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitosis inhibitors: compounds of group K1 : dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, com pounds of group K1 , in particular dinitroanilines are preferred;

b10) from the group of the VLCFA inhibitors:

chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazoli- nones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, 11.3, 11.4, II.5, II.6, II.7, ll.8 and II.9

the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576;

among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5- pentafluorphenyloxy-1⁴-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1 );

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxinic herbicides:

2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8; MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72- 9)and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium; b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3 and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, inda- nofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, me thyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.

Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C₄-alkyl, hydroxy-Ci-C₄-alkoxy-Ci-C₄-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisoprop- ylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammoni- um, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethyl ammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxyeth-1 -oxy)eth-1- ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2- hydroxyethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltrime- thylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), fur thermore phosphonium ions, sulfonium ions, preferably tri(Ci-C₄-alkyl)sulfonium, such as trime- thylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensul- fate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C1-C4- alkanoic acids, preferably formate, acetate, propionate and butyrate.

Herbicidal compounds B and/or safeners C as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, pro- pargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Ci₀-alkylthio esters. Preferred mono- and di-Ci-C₆- alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, pro pyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methyl hexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethyl hexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight- chain or branched Ci-C₄-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester. An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.

In one embodiment of the invention there is provided a method of protecting a crop of useful plants susceptible to and/or under attack by undesired vegetation, which are resistant to a herb icide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said undesired vegetation, a composition comprising at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally ac ceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and the herbicide, towards which undesired vege tation is resistant. In another embodiment of the invention, the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one inhibitor of the lipid biosynthesis (herbi cide b1 ). These are compounds that inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides). The ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.

In yet another preferred embodiment of the invention, the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one ALS inhibitor (herbicide b2). The herbi- cidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.

In yet another preferred embodiment of the invention, the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one inhibitor of photosynthesis (herbicide b3). The herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on divert ing the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis. Amongst these, PSII inhibitors are preferred.

In yet another preferred embodiment of the invention, the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one bleacher-herbicide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene de- saturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).

In yet another preferred embodiment of the invention, the compositions contain at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally accepta ble salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one mitosis inhibitor (herbicide b9). The her bicidal activity of these compounds is based on the disturbance or inhibition of microtubule for- mation or organization, and thus on the inhibition of mitosis. These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.

As to the given mechanisms of action and classification of the active substances, see e.g.

"HRAC, Classification of Herbicides According to Mode of Action",

https://www.plantprotection.org/hrac/MOA.html).

Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b5 and b9.

Particular preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2 and b5.

In one embodiment of the present invention the compositions according to the present invention comprise at least one compound of formula (I) and at least one safener C.

Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the pre sent compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant. The safeners and the at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and/or the herbicides B can be applied simultaneously or in succession.

Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1 -phenyl-4, 5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phos- phorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group. In particular, benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicy- clonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31 -4), metcamifen and BPCMS (CAS 54091-06-4).

The active compounds B of groups b1) to b15) and the active compounds C are known herbi cides and safeners, see, for example, The Compendium of Pesticide Common Names

(https://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edi tion, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine [CAS No. 52836-31 -4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.

The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this sub stance was only assigned to one mechanism of action. Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agricul turally acceptable derivative in the compositions according to the invention.

In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Ex amples of a suitable ester are dicamba-methyl and dicamba-butotyl.

Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium. Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D- 3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D- isopropyl, 2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.

Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.

A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.

Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.

Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.

Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for ex ample triclopyr-ethyl and triclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.

Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium. Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate).

A suitable salt of glufosinate is for example glufosinate-ammonium.

A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.

Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.

Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.

Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

A suitable salt of naptalam is for example naptalam-sodium.

Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.

A suitable salt of quinclorac is for example quinclorac-dimethylammonium.

A suitable salt of quinmerac is for example quinmerac-dimethylammonium.

A suitable salt of imazamox is for example imazamox-ammonium.

Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.

Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.

A suitable salt of imazaquin is for example imazaquin-ammonium.

Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.

A suitable salt of topramezone is for example topramezone-sodium.

According to yet another preferred embodiment of the invention, the composition comprises as component I at least one, preferably exactly one compound of formula (I), and as component II at least one, preferably exactly one, herbicide B.

According to another preferred embodiment of the invention, the composition comprises as component I at least one, preferably exactly one compound of formula (I) as cytochrome P450 inhibitor, and as component II at least two, preferably exactly two, herbicides B different from each other.

Here and below, the term“binary compositions” includes compositions comprising one or more, for example 1 , 2 or 3, compounds of the formula (I) and either one or more, for example 1 , 2 or 3, herbicides B or one or more safeners C. Correspondingly, the term“ternary compositions” includes compositions comprising one or more, for example 1 , 2 or 3, compounds of the formula (I), one or more, for example 1 , 2 or 3, herbicides B and one or more, for example 1 , 2 or 3, safeners C.

In binary compositions comprising at least one compound of the formula (I) as component I and at least one herbicide B, the weight ratio of the active compounds kherbicide B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1. In binary compositions comprising at least one compound of the formula (I) as component I and at least one safener C, the weight ratio of the active compounds l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.

In ternary compositions comprising at least one compound of formula (I) as component I, at least one herbicide B and optionally one safener C, the relative proportions by weight of the components l:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , the weight ratio of the components l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , and the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1. The weight ratio of components I + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.

In ternary compositions comprising at least inhibitor of formula (I) as P450 inhibitor as compo nent I, at least one herbicide B and optionally one safener C, the relative proportions by weight of the components l:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , the weight ratio of the components l:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particu lar in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , and the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1. The weight ratio of compo nents I + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.

Particularly preferred herbicides B are the herbicides B as defined above; in particular the herb icides B.1 - B.202 listed below in table B:

Table B:

The safeners C, which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:

Table C

Particularly preferred are compositions 1.1 to 1.3671 , comprising the at least compound of for mula (I) as P450 inhibitor and the substance(s) as defined in the respective row of table 1 : Table 1 (compositions 1.1 to 1.3671 ):

The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.

The compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).

The compositions according to the invention control vegetation on non-crop areas very efficient ly, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

The compositions according to the invention are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by custom ary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The herbicidal compositions may also be applied by the low-volume or the ultra-low-volume method, or in the form of microgranules.

Application of the herbicidal compositions according to the present invention can be done be fore, during and/or after, preferably during and/or after, the emergence of the undesirable plants.

The herbicidal compositions according to the present invention can be applied pre- or post emergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds (I) as P450 inhibitor and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the composition according to the invention can be applied by treating seed. The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.

The term“seed” comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods. Moreover, it may be advantageous to apply the compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for con trolling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

When employed in plant protection, the compound of formula (I) and B and, if appropriate, C without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.

In another embodiment of the invention, the application rate of the compound of formula (I) as P450 inhibitor and B and, if appropriate, C, is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).

In another preferred embodiment of the invention, the rates of application of the compound of formula (I) according to the present invention (total amount of compound of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.

In another preferred embodiment of the invention, the application rates of the compound of for mula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.

In another preferred embodiment of the invention, the application rate of the compound of for mula (I) is 0.1 to 1000 g/ha, preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.

The required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.

The required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant prop agation material (preferably seeds) are generally required.

In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. compound of formula (I) and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

When used in the protection of materials or stored products, the amount of the compound of formula (I) as P450 inhibitor applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the compound of formula (l)per cubic meter of treated material. In the methods of the present invention it is immaterial whether the compound of formula (I) as P450 inhibitor, and the further herbicide component B and/or the herbicide safener compound C are formulated and applied jointly or separately.

In the case of separate application it is of minor importance, in which order the application takes place. It is only necessary, that the compound of formula (I) as P450 inhibitor and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 14 days, in particular at most 7 days.

Depending on the application method in question, the compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec altissima, Beta vulgaris spec rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossy- pium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vul- gare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Ni- cotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vul garis, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, So- lanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

Preferred crops are Arachis hypogaea, Beta vulgaris spec altissima, Brassica napus var. na pus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossy pium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays

Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, pota toes, peanuts or permanent crops.

The compositions according to the invention can also be used in crops which have been modi fied by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait. The term "crops" as used herein includes also (crop) plants which have been modified by muta genesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.

Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect. Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the ge nome of a plant in order to add a trait or improve a trait. These integrated genes are also re ferred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants com prising a specific transgene on a specific genomic locus are usually described as comprising a specific“event”, which is referred to by a specific event name. Traits which have been intro duced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.

Herbicide tolerance has been created by using mutagenesis as well as using genetic engineer ing. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbi cides by conventional methods of mutagenesis and breeding comprise plant varieties commer cially available under the name Clearfield^®. However, most of the herbicide tolerance traits have been created via the use of transgenes.

Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbi cides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.

Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601 , gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1 -2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1 -2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.

Transgenic corn events comprising herbicide tolerance genes are for example, but not exclud ing others, DAS40278, MON801 , MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21 , MZHG0JG, HCEM485, VCO- 01981 -5, 676, 678, 680, 33121 , 41 14, 59122, 98140, Bt10, Bt176, CBH-351 , DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

Transgenic soybean events comprising herbicide tolerance genes are for example, but not ex cluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21 , A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.

Transgenic cotton events comprising herbicide tolerance genes are for example, but not exclud ing others, 19-51 a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN 1021 1 , BXN 10215, BXN 10222, BXN 10224, MON1445, MON 1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.

Transgenic canola events comprising herbicide tolerance genes are for example, but not ex cluding others, MON88302, HCR-1 , HCN 10, HCN28, HCN92, MS1 , MS8, PHY14, PHY23, PHY35, PHY36, RF1 , RF2 and RF3.

Insect resistance has mainly been created by transferring bacterial genes for insecticidal pro teins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec and synthetic variants thereof, like cry1 A, crylAb, cry1Ab-Ac, cryl Ac, cry1A.105, cry1 F, cry1 Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1 , cry35Ab1 , cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particu lar genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7.

Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt1 1 , Bt176, MON801 , MON802, MON809, MON810, MON863, MON8741 1 , MON88017, MON89034, 33121 , 41 14, 5307, 59122, TC1507, TC6275, CBH-351 , MIR162, DBT418 and MZIR098.

Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701 , MON87751 and DAS-81419.

Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON1076, MON 15985, 31707, 31803, 31807, 31808, 42317, BN LA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB1 19 and SGK321.

Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.

Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1 , Pj.D6D, Nc.Fad3, fad2-1A and fatb1 -A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.

Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb- 4, comprised by soybean event IN D-00410-5. Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide toler ance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbi cide tolerance and tolerance to abiotic conditions.

Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or inte grated genes and the respective events are available from websites of the organizations“Inter national Service for the Acquisition of Agri-biotech Applications (ISAAA)”

(https://www.isaaa.org/gmapprovaldatabase) and the“Center for Environmental Risk Assess ment (CERA)” (https://cera-gmc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WO2017/011288.

In an embodiment, the use of compositions according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might in volve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, ear ly or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spec trum or content.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material produc tion, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

Furthermore, it has been found that the the compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cot ton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard compositions have been found for the desiccation and/or defoliation of plants, pro cesses for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.

As desiccants, the compositions according to the invention are suitable in particular for desic cating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soy bean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is the facilitation of harvesting, which is made possible by concentrat ing within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

Mixtures

In one embodiment, the present invention also relates to a mixture of at least one compound of formula (I) in free form or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor of the present invention with at least one mixing partner as defined herein after. Preferred are binary mixtures of at least one compound of formula (I) of the present invention as component I with one mixing partner as defined herein after as component II. Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10. In such binary mixtures, components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.

Mixing partners can be selected from pesticides, in particular insecticides, nematicides, acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like. Preferred mixing component II partners are insecticides, nematicides, herbicides and fungicides. The fol lowing list of pesticides (component II) (e. g. insecticides, nematicides, herbicides, fungicides and biopesticides), in conjunction with which the compounds of formula (I) can be used, is in tended to illustrate the possible combinations but does not limit them:

A) Respiration inhibitors

Inhibitors of complex III at Q₀ site: azoxystrobin (A.1.1), coumethoxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1.6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mande- strobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyra- clostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino- /V-methyl-acetamide (A.1.18), pyribencarb (A.1.19), triclopyricarb/chlorodincarb (A.1 .20), fa- moxadone (A.1.21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl-pyrazol-3- yl)oxylmethyl]phenyl]-/V-methoxy-carbamate (A.1.22), 1 -[2-[[1 -(4-chlorophenyl)pyrazo!-3-yi]oxy- methyl]-3-methyi-pheny!]-4-methyl-tetrazo!-5-one (A.1.25), (Z2£)-5-[1 -(2,4-dich!oro- phenyi)pyrazo!-3-y!]-oxy-2-methQxyimino- V,3-dimethy!-pent-3-enamide (A.1.34), (Z 2£)-5-[1 -(4- ch!orophenyi)pyrazoi-3-y!]oxy-2-rnethoxyimino-/V,3-dimethyl-pent-3-enamide (A.1.35), pyrim- inostrobin (A.1.36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylen)phenyl)-3- methoxy-acrylic acid methylester (A.1.38);

inhibitors of complex III at Q, site: cyazofamid (A.2.1), amisulbrom (A.2.2),

[(6S,7/?,8,^-8-benzyi-3-[(3-hydroxy-4-methoxy-pyridine-2-carbony!)amino]-6-methyl-4,9-dioxo- 1 ,5-dioxonan-7-yi] 2-methyipropanoale (A 2.3), fenpicoxamid (A.2.4);

inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), bos- calid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyrox- ad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyrazi- flumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluindapyr (A.3.28), methyl (£)-2-[2-[(5-cyano-2-methyl- phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucypram (A.3.31 ), 2- (difluoromethyl)-/V-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2- (difluoromethyl)-/V-[(3A)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2- (difluoromethyl)-AA(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2- (difluoromethyl)-/V-[(37?)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2- (difluoromethyl)-/V-(1 ,1 -dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2- (difluoromethyl)-/V-[(3/?)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2- (difluoromethyl)-/V-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2- (difluoromethyl)-/V-[(3/?)-3-isobutyl-1 , 1 -dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39); other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.11); silthiofam (A.4.12);

B) Sterol biosynthesis inhibitors (SBI fungicides)

C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromu- conazole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1 .5), diniconazole (B.1.6), dinicona- zole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1.9), fluquinconazole (B.1.10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazole (B.1.20), penconazole (B.1.21 ), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1 .26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1 .30), 2-(2,4-difluorophenyl)-1 ,1 -difluoro-3- (tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4- difluorophenyl)-1 ,1 -difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl] propan-2- ol (B.1.32), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl- 5-(p-tolylmethyl)-1-(1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1 .45), prochloraz (B.1 .46), triflumizol (B.1.47); pyrimidines, pyridines, pipera zines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro-phenyl)-5- (2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52);

Deltal 4-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);

Inhibitors of 3-keto reductase: fenhexamid (B.3.1);

Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1);

C) Nucleic acid synthesis inhibitors

phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1.2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofurace (C.1.6), oxadixyl (C.1.7);

other nucleic acid synthesis inhibitors: hymexazole (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of cell division and cytoskeleton

tubulin inhibitors: benomyl (D.1.1 ), carbendazim (D.1.2), fuberidazole (D1.3), thia bendazole (D.1.4), thiophanate-methyl (D.1 .5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5- phenyl-pyridazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1.7), /V-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), /V-ethyl-2-[(3-ethynyl- 8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinol- yl)oxy]-/V-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-(2-flu- oroethyl)-2-methoxy-acetamide (D.1.11 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-propyl- butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-/V-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-/V-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-/V-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1 .15), 4- (2-bromo-4-fluoro-phenyl)-/V-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16); other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of amino acid and protein synthesis

methionine synthesis inhibitors: cyprodinil (E.1.1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);

protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hy drochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);

F) Signal transduction inhibitors

MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

G protein inhibitors: quinoxyfen (F.2.1 );

G) Lipid and membrane synthesis inhibitors

Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);

lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);

phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 ); inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluoro methyl-1 H- pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3,5-bis(difluoromethyl)-1 7-pyrazol-1-yl]acetyl}piperidin-4- yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1- [2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-/V-tetralin-1-yl-pyridine-2- carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-/V-tetralin-1 - yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1- yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1 -[2-[5-cyclopropyl-3- (difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.7), 4- [1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-/\/-tetralin-1 -yl-pyridine-2- carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4- piperidyl]-/V-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-

1-yl]acetyl]-4-piperidyl]-/V-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl- 3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-/V-tetralin-1-yl-pyridine-2-carboxamide

(G.5.1 1 );

H) Inhibitors with Multi Site Action

inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1 .4), copper oxychloride (H.1 .5), basic copper sulfate (H.1.6), sul fur (H.1.7);

thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H .2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);

organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H .3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1);

guanidines and others: guanidine (H.4.1), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 7,5/f[1 ,4]di- thiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2 -/,6/ )-tetraone (H.4.10);

I) Cell wall synthesis inhibitors

inhibitors of glucan synthesis: validamycin (1.1.1), polyoxin B (1.1.2);

melanin synthesis inhibitors: pyroquilon (1.2.1), tricyclazole (1.2.2), carpropamid (I.2.3), dicyclomet (1.2.4), fenoxanil (1.2.5);

J) Plant defence inducers

acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1 .2), isotianil (J.1.3), tiadinil (J.1.4), prohexa- dione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11 ), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-/V-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J .1 .10);

K) Unknown mode of action

bronopol (K.1.1), chinomethionat (K.1 .2), cyflufenamid (K.1 .3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1.8), difenzoquat (K.1 .9), di- fenzoquat-methylsulfate (K.1.10), diphenylamin (K.1.1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1.15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1 .20), tolprocarb (K.1.21 ), oxin- copper (K.1 .22), proquinazid (K.1 .23), tebufloquin (K.1 .24), tecloftalam (K.1.25), triazoxide (K.1.26), /Vⁱ(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-/V-ethyl-/V-methyl formamidine (K.1.27), /Vⁱ(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-/V-ethyl-/V- methyl formamidine (K.1 .28), /V^l[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]oxy]-2,5- dimethyl-phenyl]-/V-ethyl-/V-methyl-formamidine (K.1.29), /V¹(5-bromo-6-indan-2-yloxy-2-methyl- 3-pyridyl)-/V-ethyl-/V-methyl-formamidine (K.1.30), /V 5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-

2-methyl-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1 .31), L/^d-^oitio-q-^- isopropylcyclohexoxy)-2-methyl-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1.32), /V^S-bromo- 2-methyl-6-(1-phenylethoxy)-3-pyridyl]-/V-ethyl-/V-methyl-formamidine (K.1.33), /V¹(2-methyl-5- trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-/V-ethyl-/V-methyl formamidine (K.1.34), N’- (5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-/V-ethyl-/V-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)- V-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy- acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]-pyridine (K.1 .38), 5-chloro-1-(4,6- dimethoxy-pyrimidin-2-yl)-2-nnethyl-1 /-/-benzoimidazole (K.1.39), ethyl (2)-3-amino-2-cyano-3- phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41 ), pentyl AA[6-[[(2)-[(1-methyltetrazol-5-yl)- phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl L/-[6-[[(Z)-[(1 - methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), 2-[2- [(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8- fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1.45), quinofumelin (K.1.47), 9-fluoro-2,2- dimethyl-5-(3-quinolyl)-3/7-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51 ), dichlobenti- azox (K.1 .52), /V¹(2,5-dimethyl-4-phenoxy-phenyl)-/V-ethyl-/V-methyl-formamidine (K.1 .53), pyri- fenamine (K.1.54);

L) Biopesticides

L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Ampelomyces quisqua/is, Aspergillus fiavus, Aureobasidium puiiuians, Bacillus aititudi- nis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pumi/us, B. simplex,

B. so/isalsl, B. subti!is, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Ciavi- bacter michiganensis (bacteriophages), Coniothyrium minitans, Cryphonectria parasitica, Cryp tococcus aibidus, DHophosphora aiopecuri, Fusarium oxysporum, Cionostachys rosea f . catenu- iate (also named Giiociadium catenuiatum), Giiociadium roseum, Lysobacter antibioticus, L enzymogenes, Metschnikowia fructicoia, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor aibus, Paenibaciiius aivei, Paenibaciiius epiphyticus, P. poiymyxa, Pantoea vagans, Peniciiiium biiaiae, Ph/ebiopsis gigantea, Pseudomonas s p . , Pseudomonas chioraphis, Pseudo- zyma fioccuiosa, Pichia anomaia, Pythium oiigandrum, Sphaerodes mycoparasitica, Streptomy- ces griseoviridis, S. iydicus, S. vioiaceusniger, Taiaromyces flavus, Trichoderma aspereiioides,

T. aspereiium, T. atroviride, T fertile, T. gamsii, T harmatum, T. harzianum, T poiysporum, T stromaticum, T. virens, T. viride, Typhuia phacorrhiza, Uiociadium oudemansii, Verticiiiium dahl ia, zucchini yellow mosaic virus (avirulent strain);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachaiinensis extract;

L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israe/ensis, B. t. ssp. gaiieriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beau- veria bassiana, B. brongniartii, Burkhoideria s p p . , Chromobacterium subtsugae, Cydia pomonei- /a granulovirus (CpGV), Cryptophiebia ieucotreta granulovirus (CrleGV), Fia vobacterium s p p . , Heiicoverpa armigera nucleopolyhedrovirus (HearNPV), Heiicoverpa zea nucleopolyhedrovirus (HzNPV), Heiicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bac- teriophora, isaria fumosorosea, Lecaniciiiium iongisporum, L. muscarium, Metarhizium anisopii- ae, M. anisopiiae var. anisopiiae, M. anisopiiae var. acridum, Nomuraea riieyi, Paeciiomyces fumosoroseus, P. iiiacinus, Paenibaciiius popiiiiae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas f/uorescens, Spodoptera iittoraiis nucleopoly- hedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces gaibus, S. microfiavus,

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nemat- icidal activity: L-carvone, citral, (£, )-7,9-dodecadien-1-yl acetate, ethyl formate, (£ )-2, 4-ethyl decadienoate (pear ester), (Z,Z,E)- 7,11 ,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1 -butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1 -ol, (£ )-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1 - ol, (£)-1-octen-3-ol, pentatermanone, (E,E2)-3,8,11 -tetradecatrienyl acetate, {Z,E)- 9,12- tetradecadien-1 -yl acetate, ( )-7-tetradecen-2-one, (2)-9-tetradecen-1 -yl acetate, {Z) 1 1 - tetradecenal, (Z)-1 1 -tetradecen-1 -ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;

L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth pro moting and/or yield enhancing activity: Azospirillum amazonense, A. brasiiense, A. iipoferum, A. irakense, A. haiopraeferens, Bradyrhizobium s pp . , B. eikanii, B. japonicum, B. iiaoningense, B. lupin i, Delftia acidovorans, Glomus intraradices, Mesorhizobium spp., Rhizobium iegumi- nosarum bv. phaseoii, R. i. bv. trifoiii, R. i. bv. viciae, R. tropici, Sinorhizobium meiiioti,

(M) Insecticides from classes M.1 to M.29

M.1 Acetylcholine esterase (AChE) inhibitors: M .1 A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M .8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;

M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate; M.21 Mitochondrial complex I electron transport inhibitors, e.g. M .21A METI acaricides and in- sec-ticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-'ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-^,methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 ,2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonyl^aminoJbenzoylJ-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-'carbamoylJ-phenylJ^S-chloro^-pyridy -S-itrifluoromethy pyrazole-S- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylideneJcarbamoylJ-phenylJ^-iS-chloro^-pyridyO-S-itrifluoro-Tnethy pyrazole-S- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine ; M.UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN.9.b): fluxametamide ; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11 .c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M.UN.1 1.d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;

M . U N .1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;

M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ^^^-tetrafluoro-Htrifluoromethyl^ethyll-O- (trifluoromethyl)phenyl]annino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)-ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.UN.1 1.i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 .j) 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethy - propyllphenylJ^-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; M.UN.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-l -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;

M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.U N.1 1.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ^^^-tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoyll-'phenyll^-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M .U N .12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M .UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5- yl]pyridine-2-carboxamide; M.U N.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide ; M.UN.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN .12.g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio- propanamide; M .U N .12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N ,2-dimethyl-3-methylthio- propanamide; M .U N.12.1) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M .U N.12.m) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-ethyl-3-methylthio- propanamide ;

M. UN.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol;

M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M. UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; M.UN.16e) N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.UN.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M .UN.16g) 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide; M .U N .16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.U N.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide,

M. UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17c) N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M. UN.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide; M .U N .18b) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide; M. UN.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M .U N .18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;

M.UN.19 sarolaner , M.UN.20 lotilaner ;

M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ; M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;

M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazole-3-carboxamide ; M.UN.25 acynonapyr ; M.UN.26 benzpy-rimoxan ; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)-4- (trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide . N) Herbicides from classes b.1 to b.15

b.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalo- fop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-chloro-4-cyclo-'propyl-2'-fluoro[1 ,1 ^,-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-te- tramethyl-2/f pyran-3(6 /)-one (1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1 ,V-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2/7-pyran-3(6/ )-one (1312337-45-3); 4-(4'-chloro-4-ethyl-2'- fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2A/-pyran-3(6/-/)-one (1033757-93-5); 4- (2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2 ⁱ7-pyran-3,5(4/7,6 /)-dione (1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2/fpyran-3-one (1312337-48-6); 5-(acetyloxy)-4-(2^',4'-dichloro-4- cyclopropyl- [1 ,r-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetrannethyl-2/-/-pyran-3-one; 5-(acetyloxy)- 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2/-/-pyran-3-one (1312340-82-1 ); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 , 1 '-biphenyl]-3-yl)-3,6-dihydro-2, 2,6,6- tetramethyl-2/7-pyran-3-one (1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-

3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2/7-pyran-3-yl carbonic acid methyl ester (1312337- 51-1); 4-(2^',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5- oxo-2 7-pyran-3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)- 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2 pyran-3-yl carbonic acid methyl ester (1312340-83-2);

4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2 7-pyran-3-yl carbonic acid methyl ester (1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate, vernolate;

b.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazo- sulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primi- sulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron- ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, diclosulam, flumetsulam, flo- rasulam, metosulam, penoxsulam, pyrimisulfan, pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methyhethyl ester (420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]-^,methyl]amino]-benzoic acid propyl ester (420138-40-5), /V-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]- benzenemethanamine (420138-01 -8); flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone, thiencarbazone-methyl; triafamone; b.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chlohdazone, cyanazine, desmetryn, dimethametryn,hexazinone, methbuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlo- rotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metam- itron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthi- uron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, bromo- fenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, propanil; diquat, diquat- dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;

b.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3- yl)phenoxy]-2-pyridyloxy]acetate (353292-31-6), /V-ethyl-3-(2,6-dichloro-4-trifluoro- methylphenoxy)-5-methyl-1 A/-pyrazole-1 -carboxamide (452098-92-9), /V-tetrahydrofurfuryl- 3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H- pyrazole-1 -carboxamide (915396-43-9), /V-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 /7-pyrazole-1 -carboxamide (452099-05-7), /V-tetrahydro-^,furfuryl-3-(2-chloro-6-fluoro-4-trifluoro-^,methylphenoxy)-5-methyl- 1 / pyrazole-1 -carboxamide (452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2/7- benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (451484-50-7), 2-(2,2,7- trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2/7-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-

1.3-dione (1300118-96-0), 1-methyl-6-trifluoro-^,methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-

3.4-dihydro-2 ^Lbenzo[1 ,4]oxazin-6-yl)-1 /-/-pyrimidine^, 4-dione (13041 13-05-0), methyl (£)-4-[2- chloro-5-[4-chloro-5-(difluoromethoxy)-1 / -methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy- but-2-enoate (948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 //-benzimidazol-4-yl]-1- methyl-6-(trifluoromethyl)-1 //-pyrimidine-2, 4-dione (212754-02-4);

b.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;

b.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate- potassium, glyphosate-trimesium (sulfosate);

b.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;

b.8 DHP synthase inhibitors: asulam;

b.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pen- dimethalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlor- thal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flam- prop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham; b.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethen- amid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, py- roxasulfone, isoxazoline compounds of the formulae 11.1 , 11.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

b.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (175899-01-1 ); b.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;

b.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5- fluoropyridine-2-carboxylic acid, benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methoxyphenyl)-5-fluoropyridine-2-carboxylate (1390661-72-9); b.14 Auxin transport inhibitors: diflufonzopyr, diflufenzopyr-sodium, naptalam, naptalam-sodium; b.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, di- fenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, meflu- idide, metam, methiozolin (403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridipha- ne;

O) Growth regulators

abscisic acid (0.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, /V-6-benzyladenine, paclobutrazol, prohexadione, prohexadio- ne-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,

2,3,5-tri-iodobenzoic acid , trinexapac-ethyl, uniconazole;

The active substances referred to as component II, their preparation and their activity e. g. against harmful insects and/or undesired vegetation and/or fungi are known (cf.:

https://www.alanwood.net/pesticides/); these substances are commercially available. The com pounds described by IUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412;

DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413;

WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358;

WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286;

WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193;

WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 ,

WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO

10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862,

WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072,

WO 13/092224, WO 11/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897,

WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/116251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/165511 , WO 1 1/081 174, WO 13/47441 ). Some compounds are identified by their CAS Registry Number which is sepa rated by hyphens into three parts, the first consisting from two up to seven digits, the second consisting of two digits, and the third consisting of a single digit.

The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component II) and/or select ed from groups M.1 to M.29.

The compounds of formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof as cytochrome P450 inhibitor and at least one further active substance simultaneously, e.g. se lected from groups M .1. to M.29, can be applied either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.

When applying compound of formula (I) and a component II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also, a broader range is possible rang ing from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1.5 hours to 5 days, even more preferred from 2 hours to 1 day. In case of a mix ture comprising a component II selected from group L), it is preferred that the pesticide II is ap plied as last treatment.

In one embodiment, the present invention provides an agricultural mixture comprising at least one compound of formula (I), and

at least one pesticidal compound selected from group M consisting of

M.1 Acetylcholine esterase (AChE) inhibitors: M.1A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor; M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M.8B chloropicrin, M.8C sulfuryl fluoride, M .8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M.10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: Cry1 Ab, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ;

M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;

M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M.20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M.21A METI acaricides and in secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M .21 B rotenone; M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-^,ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-^,methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-5-yl]carbonyl}-^,amino)benzoyl]-1 ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-'carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro-'methyl)pyrazole-3- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afido-'pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin; M.UN.8: fluazaindolizine ; M .UN.9.a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol- 3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN.9.b): fluxametamide ; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzannide; M.UN.11 .c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M .U N .1 1.d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;

M . U N .1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;

M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)-^,ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S-^^-iodo^-ll ^^^-tetrafluoro-l-itrifluoromethy -ethyll-O-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.UN.1 1.i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 .j) 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1-

(trifluoromethyl^propyllphenyl^-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; M.UN.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;

M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ^^^-tetrafluoro-l-itrifluoromethy ethyllphenyllcarbamoy^phenyll^-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; or M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M .U N .12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M .UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5- yl]pyridine-2-carboxamide; M.U N.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide ; M.UN.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN .12.g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN.12.h) N,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio- propanamide; M .U N .12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N ,2-dimethyl-3-methylthio- propanamide; M .U N.12.1) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M .U N.12.m) N-^-Chloro^-CS-pyri-'dy thiazol-S-yll-N-ethyl-S-methylthio- propanamide ; M. UN.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M. UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a] pyridin-5-ol;

M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxannide; M. UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -mothyl-ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; M.UN.16e) N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.UN.16†) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M .UN.16g) 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide; M .U N .16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.U N.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide,

M. UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17c) N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M. UN.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide; M. UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide; M . UN.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M .U N .18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;

M.UN.19 sarolaner, M.U N.20 lotilaner ;

M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 , 1 ,2, 2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ; M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;

M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide ; M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazole-3-carboxamide ; M.UN.25 acynonapyr ; M.UN.26 benzpy-rimoxan ; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)-4- (trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide. In another preferred embodiment, the present invention relates to agricultural mixtures compris ing

at least one compound of formula (I), and

at least one pesticidal compound selected from group M consisting of

M.1 Acetylcholine esterase (AChE) inhibitors: M .1 A carbamates, e.g. aldicarb, alanycarb, ben- diocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phor-ate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos,prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; MAC sulfoxaflor; MAD flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonylJ-'aminoJbenzoyll-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro-^,methyl)pyrazole-3- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide. In another embodiment, the present invention relates to agricultural mixtures wherein compound of formula (I) is selected from

ı42

and at least one pesticidal compound selected from M .1 to M.29.

In another embodiment, the present invention relates to use of agricultural mixture comprising compound of formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof and at least one pesticidal compound selected from group M for controlling or combating insects and/or non-crop pests.

In one embodiment, the present invention provides an agricultural mixture comprising at least one compound of formula (I), and

at least one herbicidal compound selected from group b consisting of b1 ) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

b9) mitosis inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11 ) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxinic herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and its salts and esters;

including their agriculturally acceptable salts or derivatives.

In another embodiment, the present invention relates to use of agricultural mixture comprising compound of formula (I) and at least one herbicidal compound selected from group b for con trolling or combating undesired vegetation.

According to the invention, the solid material (dry matter) of the biopesticides (with the excep tion of oils such as Neem oil) are considered as active components (e. g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).

In accordance with the present invention, the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).

The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1 x 1010 CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here“CFU” may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Stei- nernema feltiae.

In the binary mixtures and compositions according to the invention the weight ratio of the com ponent I) and the component II) generally depends from the properties of the active components used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1.

According to further embodiments of the binary mixtures and compositions, the weight ratio of the component I) and the component II) usually is in the range of from 1000:1 to 1 :1 , often in the range of from 100: 1 to 1 :1 , regularly in the range of from 50:1 to 1 :1 , preferably in the range of from 20:1 to 1 :1 , more preferably in the range of from 10:1 to 1 :1 , even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1 :1.

According to further embodiments of the mixtures and compositions, the weight ratio of the component I) and the component II) usually is in the range of from 20,000:1 to 1 :10, often in the range of from 10,000:1 to 1 :1 , regularly in the range of from 5,000:1 to 5:1 , preferably in the range of from 5,000:1 to 10:1 , more preferably in the range of from 2,000:1 to 30:1 , even more preferably in the range of from 2,000:1 to 100:1 and in particular in the range of from 1 ,000:1 to 100:1 .

According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component I) and the component II) usually is in the range of from 10:1 to 1 :1000, often in the range of from 1 :1 to 1 :100, regularly in the range of from 1 :1 to 1 :50, preferably in the range of from 1 :1 to 1 :20, more preferably in the range of from 1 :1 to 1 :10, even more preferably in the range of from 1 :1 to 1 :4 and in particular in the range of from 1 :1 to 1 :2.

According to further embodiments of the mixtures and compositions, the weight ratio of the component I) and the component II) usually is in the range of from 10:1 to 1 :20,000, often in the range of from 1 :1 to 1 :10,000, regularly in the range of from 1 :5 to 1 :5,000, preferably in the range of from 1 : 10 to 1 :5,000, more preferably in the range of from 1 :30 to 1 :2,000, even more preferably in the range of from 1 :100 to 1 :2,000 to and in particular in the range of from 1 :100 to 1 :1 ,000.

In the ternary mixtures, i.e. compositions according to the invention comprising the component I) and component II) and a compound III (component III), the weight ratio of component I) and component II) depends from the properties of the active substances used, usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component I) and component III) usually it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50:1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 and in particular in the range of from 1 :4 to 4:1.

Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the com ponent I).

These ratios are also suitable for inventive mixtures applied by seed treatment.

When mixtures comprising microbial pesticides are employed in crop protection, the application rates preferably range from about 1 x 106 to 5 x 1016 (or more) CFU/ha, preferably from about 1 x 108 to about 1 x 1013 CFU/ha, and even more preferably from about 1 x 109 to 5 x 1015 CFU/ha and particularly preferred even more preferably from 1 x 1012 to 5 x 1014 CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e. g. Steinernema feltiae), the application rates preferably range inform about 1 x 105 to 1 x 1012 (or more), more prefera bly from 1 x 108 to 1 x 101 1 , even more preferably from 5 x 108 to 1 x 1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.

When mixtures comprising microbial pesticides are employed in seed treatment, the application rates with respect to plant propagation material preferably range from about 1 x 106 to 1 x 1012 (or more) CFU/seed. Preferably, the concentration is about 1 x 106 to about 1 x 109 CFU/seed. In the case of the microbial pesticides II, the application rates with respect to plant propagation material also preferably range from about 1 x 107 to 1 x 1014 (or more) CFU per 100 kg of seed, preferably from 1 x 109 to about 1 x 1012 CFU per 100 kg of seed.

The biopesticides from group L1 ) and/or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity. The biopesticides from group L3) and/or L4) may also have fun gicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regula tor, plant growth promoting and/or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.

1 ) Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices such as ATCC or DSM refer to the acronym of the respective culture collec tion, for details see e. g. here: https://www. wfcc.info/ccinfo/collection/by_acronym/), are referred to in literature, registered and/or are commercially available: mixtures of Aureobasidium pullu- lans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e. g. blastospores in BlossomProtect® from bio-ferm GmbFI, Austria), Azospirillum brasilense Sp245 originally isolat ed in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 11005; e. g. GEL- FIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e. g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz® from Simbiose-Agro, Brazil; Plant Soil 331 , 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331 ; US 8,445,255); B. amy- loliquefaciens spp. plantarum D747 isolated from air in Kikugawa-shi, Japan (US 20130236522 A1 ; FERM BP 8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefa- ciens spp. plantarum FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e. g. Taegro® from Novozyme Biologicals, Inc., USA), B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil in Brandenburg, Ger many (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciens ssp. plantarum M BI600 isolated from faba bean in Sut ton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B 50595;

US 2012/0149571 A1 ; e. g. Integral® from BASF Corp., USA), B. amyloliquefaciens spp. planta rum QST-713 isolated from peach orchard in 1995 in California, U.S.A. (N RRL B 21661 ; e. g. Serenade® MAX from Bayer Crop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ 1000 isolated in 1992 in South Dakoda, U.S.A. (also called 1 BE; ATCC BAA-390; CA 2471555 A1 ; e. g. QuickRoots™ from TJ Technologies, Watertown, SD, USA), B. firmus CNCM 1-1582, a variant of parental strain EIP-N1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009/126473, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707-01 ; e. g. PRO MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tra- cheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pu milus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B 30087; e. g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Mi crobiol. 27, 372-379, 2004; US 2010/0260735; WO 201 1/109395); B. thurin-giensis ssp. aiza- wai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG 6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Miinsingen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent BioSci- ences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B- 50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1 , a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novodor® from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.L, Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Con- chyloctenia punctata (N RRL 50757; e. g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMI A 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e. g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661 -666, 1990; e. g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 201 1); B. japonicum strains deposited at SEMIA known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASF Agri cultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural var iant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON/M/91-08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e. g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha- beta) protein (Science 257, 85-88, 1992; e. g. Messenger™ or HARP-N Tek from Plant Health Care pic, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011 ; e. g. H el i covex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e. g. Gemstar® from Certis LLC, USA), Heli coverpa zea nucleopolyhedrovirus ABA-NPV-U (e. g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e. g. Nemasys® G from BASF Agricul tural Specialities Limited, U K), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynu- ra in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e. g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhizium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Austria (DSM 3884, ATCC 90448; e. g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolat ed from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e. g. formerly Shem- er® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89/030550; W01991/02051 ; Crop Protection 27, 352-361 , 2008; e. g. BioAct®from Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from a variety of European loca tions including Germany: P. epiphyticus Lu17015 (WO 2016/020371 ; DSM 26971), P. polymyxa ssp. plantarum Lu16774 (WO 2016/020371 ; DSM 26969), P. p. ssp. plantarum strain Lu17007 (WO 2016/020371 ; DSM 26970); Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD 5833; Federal Register 76(22), 5808, February 2, 201 1 ; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA), Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and/or ATCC 22348 (= ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1 ), 91 -102, 1998; US 5,026,417, WO 1995/017806; e. g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e. g. Regalia® SC from Marrone Bioinnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e. g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus NRRL B-50550 (WO

2014/124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41 R isolated in South Africa (N RRL 50759; also referred to as T. fertile; e. g. Trichoplus® from BASF Agricul- tural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

According to one embodiment of the inventive mixtures, the at least one component II is select ed from the groups L1) to L5):

L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1 ), Bacillus amylolique- faciens AP-188 (L.1.2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B. amylo->lique- faciens ssp. plantarum FZB24 (L.1 .4), B. amyloliquefaciens ssp. plantarum FZB42 (L.1 .5), B. amyloliquefaciens ssp. plantarum MBI600 (L.1.6), B. amyloliquefaciens ssp. plantarum QST- 713 (L.1.7), B. amyloliquefaciens ssp. plantarum TJ1000 (L.1 .8), B. pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7 (L.1 .1 1 ), B. pumilus KFP9F (L.1 .12), B. pumilus QST 2808 (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FB17 (L.1 .15), Coniothyrium mini tans CON/M/91 -08 (L.1.16), Metschnikowia fructicola NRRL Y 30752 (L.1.17), Paenibacillus alvei NAS6G6 (L.1.18), P. epiphyticus Lu17015 (L.1.25), P. polymyxa ssp. plantarum Lu16774 (L.1 .26), P. p. ssp. plantarum strain Lu17007 (L.1.27), Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851 (L.1 .20), Penicillium bilaiae ATCC 18309 (L.1 .21 ), Streptomyces micro- flavus NRRL B-50550 (L.1 .22), Trichoderma asperelloides JM41 R (L.1.23), T. harzianum T-22 (L.1 .24);

L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein (L.2.1 ), Reynoutria sachalinensis extract (L.2.2);

L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Bacillus firmus I 1582 (L.3.1); B. thuringiensis ssp. aizawai ABTS-1857 (L.3.2), B. t. ssp.

kurstaki ABTS-351 (L.3.3), B. t. ssp. kurstaki SB4 (L.3.4), B. t. ssp. tenebrionis NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.11 ), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces lilacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema car- pocapsae (L.3.18), S. feltiae (L.3.19);

L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nemat icidal activity: cis-jasmone (L.4.1 ), methyl jasmonate (L.4.2), Quillay extract (L.4.3);

L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth pro moting and/or yield enhancing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1 ), A. bra- silense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), B. elkanii SEMIA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5079 (L.5.7), B. japonicum SEMIA 5080 (L.5.8).

The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound of formula (I) (component I) and at least one biopesticide selected from the group L) (component II), in particular at least one biopesticide selected from the groups L1) and L2), as described above, and if desired at least one suitable auxiliary.

The present invention furthermore relates to agrochemical compositions comprising a mixture of of at least one compound of formula (I) (component I) and at least one biopesticide selected from the group L) (component II), in particular at least one biopesticide selected from the groups L3) and L4), as described above, and if desired at least one suitable auxiliary.

Preference is also given to mixtures comprising as pesticide II (component II) a biopesticide selected from the groups L1), L3) and L5), preferably selected from strains denoted above as (L.1 .2), (L.1 .3), (L.1 .4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11 ), (L.1.12), (L.1 .13), (L.1 .14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1 .21), (L.1.25), (L.1.26), (L.1.27), (L.3.1 ); (L.3.9), (L.3.16), (L.3.17), (L.5.1 ), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2), and (L.4.1 ); even more preferably selected from (L.1.2), (L.1 .6), (L.1 .7), (L.1.8), (L.1.11 ), (L.1 .12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1 .19), (L.1.20), (L.1.21), (L.3.1); (L.3.9),

(L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2), and (L.4.1). These mixtures are partic ularly suitable for treatment of propagation materials, i. e. seed treatment purposes and likewise for soil treatment. These seed treatment mixtures are particularly suitable for crops such as ce reals, corn and leguminous plants such as soybean.

Preference is also given to mixtures comprising as pesticide II (component II) a biopesticide selected from the groups L1 ), L3) and L5), preferably selected from strains denoted above as (L1.1), (L.1.2), (L.1.3), (L.1 .6), (L.1 .7), (L.1 .9), (L.1 .1 1 ), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1 .17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1 .26), (L.1.27), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.1 1 ), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2), (L.1.7), (L.1.11 ), (L.1 .13), (L.1 .14), (L.1.15), (L.1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.1 1), (L.3.12), (L.3.15), and (L.4.2). These mixtures are particularly suitable for foliar treatment.

These mixtures for foliar treatment are particularly suitable for vegetables, fruits, vines, cereals, corn, leguminous crops such as soybeans.

The mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds (I). Concerning usual ingredients of such composi tions reference is made to the explanations given for the compositions containing compounds (I)·

According to one embodiment, the microbial pesticides selected from groups L1 ), L3) and L5) embrace not only the isolated, pure cultures of the respective microorganism as defined herein, but also its cell-free extract, its suspensions in a whole broth culture or as a metabolite- containing culture medium or a purified metabolite obtained from a whole broth culture of the microorganism.

When living microorganisms, such as pesticides II from groups L1 ), L3) and L5), form part of the compositions, such compositions can be prepared as compositions comprising besides the ac tive ingredients at least one auxiliary by usual means (e. g. H.D. Burges: Formulation of Micobi- al Biopesticides, Springer, 1998). Suitable customary types of such compositions are suspen sions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions, capsules, pastes, pastilles, wettable powders or dusts, pressings, granules, insecticidal articles, as well as gel formulations. Herein, it has to be taken into account that each formulation type or choice of auxiliary should not influence the viability of the microorganism during storage of the composition and when finally applied to the soil, plant or plant propagation material. Suitable formulations are e. g. mentioned in WO 2008/002371 ,

US 6955,912, US 5,422,107. According to one embodiment, individual components of the composition according to the in vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in vention or partially premixed components, e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined above, may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.

In a further embodiment, either individual components of the composition according to the in vention or partially premixed components, e. g. components comprising compounds of the pre sent invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.

General synthetic procedures:

¹ H-N M R: The signals are characterized by chemical shift (ppm, [delta]) vs. tetramethylsilane respectively, CDCI₃ or DMSO as solvents, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m = multiplet, q = quartet, t = triplet, d = doublet and s = singlet.

Alkylation of phenols

A solution of the 5-allyl-6- hydroxybenzo[d][1 ,3]dioxole (1 equivalent) and alkyl halide (1 .1 equivalent) were added to a suspension of potassium carbonate (2 equivalent) and a catalytic amount of iodide (0.1 equivalent; either as the sodium or tetrabutylammonium salt). The mixture was refluxed until analytical thin layer chromatography indicated the disappearance of the 5- allyl-6- hydroxybenzo[d][1 ,3]dioxole. The acetone was evaporated and the remaining mixture was portioned between water and ethyl acetate. The organic extracts were dried using anhy drous magnesium sulfate and the solvent was removed to obtain crude product. The crude product was purified by flash silica gel column chromatography. The spectroscopic properties of the purified products were recorded.

With appropriate modification of the starting materials or intermediates, the procedures as de scribed above was used to obtain further compounds of formula (I). The compounds obtained in this manner are listed in the Table A that follows, together with physical data:

Table A: Synthesis Examples

Compound

lb: When insects were exposed to high concentration of the compound (ly), no direct mortality is observed. Insect names are EPPO codes.

2. Total exposure bioassay on Frankliniella occidentalis, with metabolic resistance to spinosad. All doses are at 120 ppm. Mixtures conducted at 1 :1 ratio. Four replicates for each treatment, 20 insects per sample unit.

Conclusions: at the same dose compound (ly) has a significant higher activity on individuals with metabolic resistance to spinosad than the mixture of spinosad with PBO (Piperonyl butox- ide). Mean comparisons used LSD (a= 0.05)

3. Total exposure bioassay on Frankliniella occidentalis, with metabolic resistance to spineto- ram. All doses are at 187 ppm. Mixtures conducted at 1 :1 ratio. Four replicates for each treat- ment, 20 insects per sample unit. Conclusions: at the same dose compound (ly) has a signifi cant higher activity on individuals with metabolic resistance to spinosad than the mixture of spi nosad with PBO. Mean comparisons used LSD (a= 0.05)

lc: When insects were exposed to high concentration of the compound (Iz), no direct mortality is observed. Insect names are EPPO codes.

2. Total exposure bioassay on Frankliniella occidentalis, with metabolic resistance to spinosad All doses are at 120 ppm. Mixtures conducted at 1 :1 ratio. Four replicates for each treatment, 20 insects per sample unit.

Conclusions: at the same dose compound (Iz) has a significant higher activity on individuals with metabolic resistance to spinosad than the mixture of spinosad with PBO. Mean compari sons used LSD (a= 0.05)

2. Total exposure bioassay on Frankliniella occidentalis, with metabolic resistance to spineto- ram. All doses are at 187 ppm. Mixtures conducted at 1 :1 ratio. Four replicates for each treat ment, 20 insects per sample unit.

Conclusions: at the same dose compound (Iz) has a significant higher activity on individuals with metabolic resistance to spinosad than the mixture of spinosad with PBO. Mean compari sons used LSD (a= 0.05)

3. Total exposure bioassay on NHaparvata /ugens, with metabolic resistance to imidacloprid. All doses are at 10 ppm. Mixtures conducted at 1 :1 ratio. Four replicates for each treatment, 10 insects per sample unit.

Conclusions: at the same dose compound (Iz) has a significant higher activity on individuals with metabolic resistance to imidacloprid than the treatment containing the mixture imidacloprid + PBO. Mean comparisons used LSD (a= 0.05)

2a. The following catechol derivatives were assayed for their capacity to inhibit P450:

Bioassay method:

The microsomal P450 activity was determined using the 7-methoxyresorufin C emethylation (MROD) assay, where methoxyresorufin is converted to resorufin by

monooxygenases in the presence of NADPH and oxygen (Liu and Scott, 1998). The resorufin produced was measured fluorometrically in a 96 well microplate spectrofluorometer (Applied Biosystems, Foster City, CA) at 530/590 nm excitation/emission. Each microplate well contained 202 pL of reaction mixture which included 10 pL enzyme (1.5 mg/mL protein content), 10 pL synergist solution (5 pg/mL in methanol for CPB enzyme, and 1 mg/mL in methanol for ECBen- zyme), 0.4 pL methoxyresorufin (1 mM), 2 pL NADPH (0.01 M) and 179.6 pL potassium phos phate buffer (0.1 M, pH 7.8). The percent inhibition by dillapiol or analog was determined rela tive to resorufin produced in the presence of the methanol control. PBO at the same concentra tion was used as the positive control.

Claims

Claims:

1. A compound of formula (I)

Formula (I) or in the form of a stereoisomer, an agriculturally acceptable salt, a pro-drug, a tautomer, an isotopic form, a N-oxide, a S-oxide, a derivative or a mixture thereof; wherein

R¹ is selected from group consisting of H, halogens, CN, NO2, SH, S(C2-Ci2-alkyl), Ci-Ci2-alkyl, 0-Ci-C₇-aikyl, C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl, C=0(OH), C=0(NR¹²R¹³), 0-C₅- Ci2-alkynyl, , C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), OC=0(Cs-Ci₄-aryl), C=0(0)Cs-Ci₄- aryl, S(0₂)-C₂-Ci₂-alkyl, S(0)Ci-Ci₂-aikyl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl, (CR⁵R⁶)_nC5-Ci4-aryl, (CR⁵R⁶)_nC3-C 12-cycloalkyl, (CR⁵R⁶)nC₅-Ci₄-heteroaryl and (CR⁵R⁶)_nC3-Ci₂-heterocycloalkyl; whereby halogens are F, Cl and I;

R⁴ is selected from group consisting of H, halogens, CN, NO2, SH, S(Ci-Ci₂-alkyl), Ci-Ci2-alkyl, 0-Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl, C=0(OH), C=0(NR¹²R¹³), O- C₅-Ci2-alkynyl, C=0(H), C=0(Ci-Ci₂-aikyl), C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C⁼0(0)C₅-Ci₄-aryl, S(0₂)-C₂-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR⁵R^®)_n-C5-Ci4- aryl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl, S(0₂)(CR⁵R⁶)_n-C₅-Ci₄-aryl, (CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)_nC₃-Ci2- cycloalkyl, (CR⁵R⁶)_nCs-Ci4-heteroaryl and (CR⁵R⁶)_nC3-Ci2-heterocycloalkyl; whereby halogens are F, Cl and I;

R² is OR⁷, NO2, NR⁸R⁹, (CR⁵R⁶)_nC3-Ci2-cycloalkyl whereby C3-Ci2-cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0₂ or together with R³ forms C3-Ci₂-cycloalkyl whereby C3-Ci2-cycloalkyl contains besides carbon atoms as ring members, 1 or 2 atoms of S0₂;

R⁷ is selected from group consisting of H, Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci2-alkynyl, C=0(C₅- Ci4-aryl), (CR⁵R⁶)_nC5-Ci4-aryl, (CR⁵R⁶)_nC5-Ci4-heteroaryl, (CR⁵R⁶)_nC3-Ci2-cycloalkyl,

(CR⁵R⁶)_nC5-Ci4-aryl- C3-Ci2-membered heterocycloalkyl, (CR⁵R⁶)_nC5-Ci₂-membered heterocy cloalkyl, (CR⁵R⁶)_n-1 ,3-benzodioxolyl and (CR⁵R⁶)_nC5-Ci4-membered heterocycloalkenyl; where by R⁷ is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12e which are independently selected from the group consisting of F, Cl, Br, I, OH, SH, CN , N0₂, NR¹⁰R¹¹, O-C1-C12-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₄-C₆-alkynyl, Ci-Ci2-alkyl, C2-Ci2-alkenyl, C2-C12- alkynyl, C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C=0(0)C₅-Ci₄-aryl, C=0(H), C₃-Ci2-cycloalkyl, C=0(Ci-Ci₂-alkyl), C=0(OH), C=0(NR¹²R¹³), C₃-Ci2-halocycloalkyl, C₅-Ci4-aryl, C₅-Ci4-heteroaryl, S(0₂)-Ci-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR⁵R⁶)_n-C5-Ci4-aryl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl, 1 ,3-benzodioxolyl, (CR⁵R⁶)_n-0-(1 ,3-benzodioxolyl) and S(0₂)(CR⁵R⁶)_n-C₅-Ci₄-aryl;

R⁸ and R⁹, identical or different, are selected from the group consisting of H, OH, NR¹⁰R¹¹, (CR⁵R⁶)nC₅-Ci4-aryl, C=0(CR⁵R⁶)nC₅-Ci₄-aryl, (CR⁵R⁶)nC₅-Ci4-heteroaryl, S(0₂)(CR⁵R⁶)n-C₅-Ci₄- aryl, S(0₂)-Ci-Ci₂-alkyl, C=0(Ci-Ci₂-alkyl), Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl,

(CR⁵R⁶)_nC5-Ci4-aryl, (CR⁵R⁶)_nC₅-Ci₂-membered heterocycloalkyl, (CR⁵R⁶)_nC5-Ci₄-membered heterocycloalkenyl and (CR⁵R⁶)_nC₃-Ci2-cycloalkyl; whereby R⁸ and R⁹ are unsubstituted or fur ther substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12f which are independently se lected from the group consisting of F, Cl, Br, I, OH, SH, CN, N0₂, NR¹⁰R¹¹, C=0(Ci-Ci₂-alkyl), C=0(OH), C=0(NR¹²R¹³), C=0(H), 0-Ci-Ci₂-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkynyl,

C=0(0)(Ci-Ci₂-alkyl), OC=0(Ci-Ci₂-alkyl), 0C=0(C₅-Ci₄-aryl), C=0(0)C₅-Ci₄-aryl, (CR⁵R⁶)_nC₅- Ci4-aryl, C₃-C₈-cycloalkyl, (CR⁵R⁶)_nC₃-Ci₂-heterocycloalkyl, (CR⁵R⁶)_nCs-Ci4-heteroaryl, C1-C12- alkyl, C₂-Ci₂-alkenyl and C₂-Ci₂-alkynyl, S(0₂)-Ci-Ci₂-alkyl, S(0)Ci-Ci₂-alkyl, S(CR⁵R⁶)_n-C₅-Ci₄- aryl, S(0)(CR⁵R⁶)_n-C₅-Ci₄-aryl and S(0₂)(CR⁵R⁶)n-C₅-Ci₄-aryl;

R³ is selected from group consisting of Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl, (CR⁵R⁶)_nC₅- Ci4-aryl, (CR⁵R⁶)_nCs-Ci4-heteroaryl, (CR⁵R⁶)_nC₃-Ci₂-cycloalkyl, (CR⁵R⁶)_nC₃-Ci₂-heterocycloalkyl, (CR⁵R⁶)_nC₃-Ci₂-heterocycloalkenyl and (CR⁵R⁶)_nC3-Ci₂-heterocycloalkynyl; whereby R³ is un substituted or further substituted by 1 , 2, 3 or 4 identical or different groups R¹²a which are inde pendently selected from the group consisting of F, Cl, Br, I, OH, SH, CN, N0₂, NR¹⁰R¹¹, O-C1- Ci₂-alkyl, 0-C₂-Ci₂-aikenyl, 0-Cg-Ci₂-alkynyl, Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, 0(CR⁵R⁶)_nC₅-Ci₄-aryl, C₂-Ci2-alkynyl, C=0(OH), C=0(NR¹²R¹³), C=0(H), OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyi), OC=0(C₃-Ci₂-cycloalkyl), C=0(0)( C3-Ci₂-cycloalkyl), 0C=0(C₂-Ci₂-aikenyl), C=0(0)(C₂-Ci₂- alkenyl), 0C=0(CR⁵R⁶)_nC₅-Ci₄-aryl, C=0(0)(CR⁵R⁶)_nC₅-Ci₄-aryl, 0C=0(H)(CR⁵R⁶)_n,

C=0(0)(H)(CR⁵R⁶)_n, C₃-Ci₂-cycloalkyl, C=0(Ci-Ci₂-alkyl), (CR⁵R⁶)_nC₆-Ci4-aryl, (CR⁵R⁶)_nC₅-C 14- heteroaryl, S-(CR⁵R⁶)_n-C₅-Ci4-aryl, S(0₂)(CR⁵R⁶)_n(C₅-Ci₄-aryl), OC=0(1 ,3-benzodioxolyl), (CR⁵R⁶)_n-1 ,3-benzodioxolyl ;

R⁵ and R⁶, identical or different, are selected from the group consisting of H, F, Cl, Br, I, OH,

CN, SH, N0₂, NR¹⁰R¹¹, 0-Ci-Ci₂-aikyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkynyl, OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyl), OC=0(C₃-Ci₂-cycloalkyl), C=0(0)( C₃-Ci₂-cycloalkyl), 0C=0(C₂-Ci₂- alkenyl), C=0(0)(C₂-Ci₂-alkenyl), 0C=0(C₅-Ci₄-aryl), C=0(0)C₅-Ci₄-aryl, C=0(Ci-Ci₂-alkyi), C=0(OH), C=0(NR¹²R¹³), C=0(H), C₃-Ci₂-cycloalkyl, C₅-Ci₄-aryl, C₃-Ci₂-heterocycloalkyl, C₅- Cn-heteroaryl, S(0₂)-Ci-Ci₂-alkyl, S(0)CrCi₂-alkyl, S(CR¹⁴R¹⁵)n-C₅-Ci₄-aryl, S(0)(CR¹⁴R¹⁵)_n- C5-Ci₄-aryl, S(0₂)(CR¹⁴R¹⁵)_n-Cs-Ci₄-aryl, Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl and C₂-Ci₂-alkynyl;

R¹⁰ and R¹¹, identical or different, are H, C3-Ci2-cycloalkyl, C2-C 12-alkenyl, C2-Ci2-alkynyl or Ci- C12 alkyl or R¹⁰ together with R¹¹ forms C₅-Ci₂-membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or Cs-Cu-membered heteroaryl;

R¹² and R¹³, identical or different, are H, C3-Ci2-cycloalkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl or Ci- C12 alkyl or R¹² together with R¹³ forms C5-Ci2-membered heterocycloalkyl, C5-Ci2-membered heterocycloalkenyl or Cs-On-membered heteroaryl; R¹⁴ and R¹⁵, identical or different, are H, C3-Ci₂-cycloalkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl or Ci- Ci2 alkyl; whereby R^12e, R^12f or R¹¾ are unsubstituted or further substituted by 1 , 2, 3 or 4 identical or dif- ferent groups which are independently selected from the group consisting of F, Cl, Br, I, OH, SH, CN, N0₂, NR¹⁰R¹¹, 0-Ci-Ci₂-alkyl, 0-C₂-Ci₂-alkenyl, 0-C₂-Ci₂-alkynyl, Ci-Ci₂-alkyl, C₂-Ci₂- alkenyl, C₂-Ci₂-alkynyl, OC=0(Ci-Ci₂-alkyl), C=0(0)(Ci-Ci₂-alkyl) and C=0(H); and n is 0, 1 , 2, 3, 4, 5 or 6. with proviso that when R¹ is H, OCH3, CH₂CH=CH₂; R⁴ is H and R² is OH , OCH3, OCH₂R wherein R is benzene ring substituted with one or more of F, Cl, Br, CH3, OCH3 then R³ is not CH₂CH=CH₂ or a structure of the following type:

where R^4’ is C1-C6 alkyl, C₅-C₆ cycloalkyl, C₂-C₆ alkenyl.

2. The compound of formula (I) of claim 1 , wherein

R¹ is H or OCH3 and R⁴ is H, or

R¹ is H or OCH₃ and R⁴ is halogen, or

R¹ is halogen and R⁴ is H, or

R¹ is halogen and R⁴ is halogen; R² is OR⁷ or NR⁸R⁹, wherein

R⁷ is H, Ci-Ci₂-alkyl, (CR⁵R⁶)_nC₅-Ci₄-aryl, (CR⁵R⁶)_nC₅-Ci4-heteroaryl or (CR⁵R⁶)_nC₅-Ci4-aryl- C3- Ci₂-membered heterocycloalkyl;

R⁸ and R⁹, identical or different are selected fromH and (CR⁵R⁶)_nC5-Ci4-aryl;

whereby R⁷ is unsubstituted or further substituted by 1 , 2, 3, 4 or 5 identical or different groups R^12e which are independently selected from the group consisting of F, Cl, Br, I, 0-Ci-Ci₂-alkyl, Ci-Ci₂-alkyl, 1 ,3-benzodioxolyl, C₅-Ci4-heteroaryl and C=0(0)(Ci-Ci₂-alkyl);

R³ is selected from the group consisting of Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl and C3- Ci₂-cycloalkyl; whereby R³ is unsubstituted or further substituted by 1 , 2 or 3 identical or differ ent groups R¹²a which are independently selected from the group consisting of F, Cl, Br, I, Cr Ci₂-alkyl, C₂-Ci₂-alkenyl, C₂-Ci₂-alkynyl, C3-Ci₂-cycloalkyl, C₅-Ci₄-aryl, C₅-Ci₄-heteroaryl, S- (CR⁵R⁶)_n-C₅-Ci4-aryl and S0₂(CR⁵R⁶)_n(C₅-Ci₄-aryl); and n is 0,1 ,2 or 3.

3. The compound of formula (I) according to claim 1 , wherein the compound of formula (I) is:

wherein X is F, Cl, Br or I and R⁵ is selected from the group consisting of FI, F, Cl, Br, I, OH, CN, SH, N0₂, N R¹⁰R¹¹, 0-Ci-Ci₂-alkyl, C=0(0)(Ci-Ci₂-alkyl), C=0(0H), C=0(NR¹²R¹³), C=0(H), C=0(Ci-Ci₂-alkyl), Ci-Ci₂-alkyl, C₂-Ci₂-alkenyl and C₂-Ci₂-alkynyl; and

X^a is F, Cl or I.

4. A composition comprising at least one compound of formula (I) according to any one of the claims 1 to 3, or in the form of a stereoisomer or an agriculturally acceptable salt or a tauto mer or an isotopic form of a N-oxide or a S-oxide or a prodrug thereof, and an auxiliary. 5. Agricultural mixtures comprising

a) at least one compound of formula (I) according to any one of the claims 1 to 3, and b) at least one pesticidal compound selected from group M consisting of

M.1 Acetylcholine esterase (AChE) inhibitors: M .1 A carbamates, e.g. aldicarb, alanycarb, ben- dio-carb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fen-carb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methimadoyl, phenthoate, phor-ate, phosalone, phosmet, phos- phamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyri- daphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thi- ometon, triazophos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M.4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.6 Chloride channel activators from the class of avermectins and milbemycins, e.g. abamectin, emamectin benzoate, ivermectin, lepimectin, or milbemectin;

M.7 Juvenile hormone mimics, such as M.7A juvenile hormone analogues hydroprene, ki- noprene, and methoprene; or M.7B fenoxycarb, or M.7C pyriproxyfen;

M.8 miscellaneous non-specific (multi-site) inhibitors, e.g. M.8A alkyl halides as methyl bromide and other alkyl halides, M .8B chloropicrin, M.8C sulfuryl fluoride, M.8D borax, or M.8E tartar emetic;

M.9 Chordotonal organ TRPV channel modulators, e.g. M.9B pymetrozine; pyrifluquinazon;

M.10 Mite growth inhibitors, e.g. M.10A clofentezine, hexythiazox, and diflovidazin, or M .10B etoxazole;

M.1 1 Microbial disruptors of insect midgut membranes, e.g. bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. is- raelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, Cryl Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, and Cry34/35Ab1 ; M.12 Inhibitors of mitochondrial ATP synthase, e.g. M.12A diafenthiuron, or M.12B organotin miti-cides such as azocyclotin, cyhexatin, or fenbutatin oxide, M.12C propargite, or M.12D tetrad ifon;

M.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient, e.g.

chlorfenapyr, DNOC, or sulfluramid;

M.14 Nicotinic acetylcholine receptor (nAChR) channel blockers, e.g. nereistoxin analogues ben-sultap, cartap hydrochloride, thiocyclam, or thiosultap sodium;

M.15 Inhibitors of the chitin biosynthesis type 0, such as benzoylureas e.g. bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, or triflumuron;

M.16 Inhibitors of the chitin biosynthesis type 1 , e.g. buprofezin;

M.17 Moulting disruptors, Dipteran, e.g. cyromazine;

M.18 Ecdyson receptor agonists such as diacylhydrazines, e.g. methoxyfenozide, tebufenozide, halofenozide, fufenozide, or chromafenozide;

M.19 Octopamin receptor agonists, e.g. amitraz;

M.20 Mitochondrial complex III electron transport inhibitors, e.g. M.20A hydramethylnon, M.20B acequinocyl, M.20C fluacrypyrim; or M .20D bifenazate;

M.21 Mitochondrial complex I electron transport inhibitors, e.g. M .21A METI acaricides and in secticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfen- pyrad, or M.21 B rotenone;

M.22 Voltage-dependent sodium channel blockers, e.g. M.22A indoxacarb, M.22B metaflumizo- ne, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]-^,ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methyhphenyl)-2- [(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]-^,methylene]-hydrazinecarboxamide; M.23 Inhibitors of the of acetyl CoA carboxylase, such as Tetronic and Tetramic acid deriva tives, e.g. spirodiclofen, spiromesifen, or spirotetramat; M.23.1 spiropidion

M.24 Mitochondrial complex IV electron transport inhibitors, e.g. M.24A phosphine such as alu minium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cyanide;

M.25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, e.g. cyenopyrafen or cyflumetofen;

M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-ylJcarbonylj-'aiTiinoJbenzoylJ-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylidene)-'carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro-'methyl)pyrazole-3- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide; or

M.29: Chordotonal organ Modulators - undefined target site, e.g. flonicamid;

M.UN. insecticidal active compounds of unknown or uncertain mode of action, e.g. afido->pyro- pen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chi- nomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhex- afon, fluopyram, fluralaner , metoxadiazone, piperonyl butoxide, pyflu-bumide, pyridalyl, tioxa- zafen, M .UN .3: 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy- 1 , 4-dioxa-9-azadispiro[4.2.4.2]- tetradec-1 1-en-10-one ,

M.UN.4: 3-(4’-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one , M.UN.5: 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, or actives on basis of bacillus firmus (Votivo, 1-1582);

M.UN.6: flupyrimin;

M.UN.8: fluazaindolizine ; M .UN.9. a): 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-

3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide ; M .UN.9.b): fluxametamide ; M.UN.10: 5-[3-[2,6- dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole;

M.UN.1 1.b) 3-(benzoylmethylamino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 - (trifluoromethyl)propyl]-6-(trifluoromethyl)phenyl]-2-fluoro-benzamide; M.UN.11 .c) 3- (benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]-benzamide; M .U N .1 1.d) N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide;

M . U N .1 1.e) N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6- (trifluoromethyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide;

M.UN.1 1.f) 4-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 ^^^-tetrafluoro-l -^rifluoromethy^ethyll-B- (trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.g) 3-fluoro-N-[2- fluoro-S-^^-iodo^-ll ^^^-tetrafluoro-l-Ctrifluoromethy -'ethyll-e-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]-N-methyl-benzamide; M.UN.1 1.h) 2-chloro-N-[3- [[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-

(trifluoromethyl)phenyl]amino]carbonyl]phenyl]- 3-pyridinecarboxamide; M.UN.1 1.i) 4-cyano-N- [2-cyano-5-[[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.11 j) 4-cyano-3-[(4-cyano-2- methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1- (trifluoromethy -'propyllphenyl^-fluoro-benzamide; M.UN.11.k) N-[5-[[2-chloro-6-cyano-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2- methyl-benzamide; M.UN.1 1.1) N-[5-[[2-bromo-6-chloro-4-[2, 2, 2-trifluoro-1 -hydroxy-1 - (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;

M.UN.1 1.m) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; M.UN.11.n) 4-cyano- N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)- propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; M.UN.1 1.o) 4-cyano-N-[2-cyano-5-[[2,6- dichloro-4-[1 ^^^-tetrafluoro-l- dfluoromethy ethyllphenyllcarbamoyl^phenyll^-methyl- benzamide; M.UN.1 1.p) N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzannide; or M.UN.12. a) 2-(1 ,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; M .U N .12.b) 2-[6-[2-(5- Fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; M.UN.12.C) 2-[6-[2-(3-Pyridinyl)-5- thiazolyl]-2-pyridinyl]-pyrimidine; M .UN.12.d) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5- yl]pyridine-2-carboxamide; M.UN.12.e) N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2- carboxamide ; M.UN.12.f) N-Ethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M.UN .12.g) N-Methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N .12.h) N ,2-Dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.i) N-Ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; M .U N.12.j) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio- propanamide; M .U N .12.k) N-[4-Chloro-2-(3-pyridyl)thiazol-5-yl]-N ,2-dimethyl-3-methylthio- propanamide; M .U N.12.1) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-methyl-3-methylthio- propanamide; M .U N.12.m) N-[4-Chloro-2-(3-pyrhdyl)thiazol-5-yl]-N-ethyl-3-methylthio- propanamide ;

M.UN.14a) 1 -[(6-Chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro- imidazo[1 ,2-a]pyridine; or M.UN.14b) 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol;

M. UN.16a) 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M. UN.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16c)

N,5-dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide;

M.UN.16d) 1 -[1 -(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; M.UN.16e) N-ethyl-1 -(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M.UN.16f) 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; M .UN.16g) 1 -[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin- 4-yl-pyrazole-4-carboxamide; M .U N .16h) N-methyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N- pyridazin-4-yl-pyrazole-4-carboxamide; M.UN.16i) 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl- N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.U N.16j) 1-(4,4-difluorocyclohexyl)-N,5-dimethyl- N-pyridazin-4-yl-pyrazole-4-carboxamide,

M. UN.17a) N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M. UN.17b) N- cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; M.UN.17c) N-cyclohexyl-2-(3-pyridinyl)- 2H-indazole-4-carboxamide; M.UN.17d) 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4- carboxamide; M.UN.17e) 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5- carboxamide; M.UN.17f) methyl 2-[[2-(3-pyridinyl)-2H-indazol-5- yl]carbonyl]hydrazinecarboxylate; M.UN.17g) N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)- 2H-indazole-5-carboxamide; M.UN.17h) N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5- carboxamide; M.UN.17i) 2-(3-pyridinyl )-N-(2-pyrimidinylmethyl )-2H-indazole-5-carboxamide; M.UN.17j) N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide,

M.UN.18a) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3- trifluoropropylsulfanyl)propanamide; M.UN.18b) N-[3-chloro-1-(3-pyridyl)pyrazol-4-yl]-N-ethyl-3- (3,3,3-trifluoropropylsulfinyl)propanamide; M.UN.18c) N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3- [(2,2-difluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; M .U N .18d) N-[3-chloro-1 -(3- pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-propanamide;

M.UN.19 sarolaner , M.UN.20 lotilaner ;

M.UN .21 N-[4-Chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1 ,1 ,2,2,2- pentafluoroethyl)-4-(trifluoromethyl)-1 H-pyrazole-5-carboxamide ; M. UN.22a 2-(3-ethylsulfonyl- 2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, or M. UN.22b 2-[3-ethylsulfonyl-5- (trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine ;

M. UN.23a 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide, or M. UN.23b 4-[5-(3,

5-dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzannide ; M. UN.24a) N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1 , 1 ,2,2, 2-pentafluoroethyl)- 4-(trifluoromethyl)pyrazole-3-carboxamide or M.UN.24b) N-[4-chloro-3-[(1- cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 , 1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazole-3-carboxamide ; M.UN.25 acynonapyr ; M.UN.26 benzpy-rimoxan ; M.UN.27 2-chloro-N-(1-cyanocyclopropyl)-5-[1 -[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4- (trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide.

6. The agricultural mixtures of claim 5, wherein the at least one pesticidal compound is se lected from group M consisting of

M.1 Acetylcholine esterase (AChE) inhibitors: M .1 A carbamates, e.g. aldicarb, alanycarb, ben- diocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethio- fencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or M.1 B organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, az- inphosmethyl, cadu-safos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, couma-phos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dime-thylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam,

methamidophos, methidathion, mevinphos, mono-crotophos, naled, omethoate, oxydemeton- methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazo- phos, trichlorfon, and vamidothion;

M.2. GABA-gated chloride channel antagonists: M.2A cyclodiene organochlorine compounds, e.g. endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), e.g. ethiprole, fipronil, flufiprole, pyrafluprole, and pyriprole;

M.3 Sodium channel modulators from the class of M.3A pyrethroids, e.g. acrinathrin, allethrin, d- cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bio- resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta- cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, me- perfluthrin,metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, and transfluthrin; or M.3B sodium channel modulators such as DDT or methoxychlor;

M.4 Nicotinic acetylcholine receptor agonists (nAChR): M .4A neonicotinoids, e.g. acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or the compounds M .4A.1 4,5-Dihydro-N-nitro-1 -(2-oxiranylmethyl)-1 H-imidazol-2-amine , M.4A.2: (2E-)-1 -[(6-Chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; or M4.A.3: 1-[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1 , 2, 3, 5,6,7- hexahydroimidazo[1 ,2-a]pyridine ; or M.4B nicotine; M.4C sulfoxaflor; M.4D flupyradifurone; M.4E triflumezopyrim;

M.5 Nicotinic acetylcholine receptor allosteric activators:spinosyns, e.g. spinosad or spinetoram; M.28 Ryanodine receptor-modulators from the class of diamides, e.g. flubendiamide, chlor- antraniliprole, cyantraniliprole, tetraniliprole, M.28.1 : (R)-3-Chlor-N 1 -{2-methyl-4-[1 , 2,2,2 - tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamid,

M .28.2: (S)-3-Chloro-N 1 -{2-methyl-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 - methyl-2-methylsulfonylethyl)phthalamid, M.28.3: cyclaniliprole, or M.28.4: methyl-2-[3,5- dibromo-2-({[3-bromo-1 -(3-chlorpyridin-2-yl)-1 H-pyrazol-S-yllcarbonylJ-'aminoJbenzoyll-l ,2- dimethylhydrazine-carboxylate; or M.28.5a) N-[4,6-dichloro-2-[(diethyl-lambda-4- sulfanylideneJ-Oarbamoyll-phenyll^-iS-chloro^-pyridylHHtrifluoromethy pyrazole-S- carboxamide; M.28.5b) N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl- phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide ; M 28.5c) N-[4-chloro- 2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5- (trifluoromethyl)pyrazole-3-carboxamide; M.28.5d) N-[4,6-dichloro-2-[(di-2-propyl-lambda-4- sulfanylideneJcarbamoylJ-phenylJ^-iS-chloro^-pyridy -S-itrifluoro-'methy pyrazole-S- carboxamide; M.28.5h) N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; M 28.5i) N-[2-(5-Amino-1 ,3,4- thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1 H-pyrazole-5- carboxamide; M.28.5j) 3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 - methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole-5-carboxamide; M.28.5k) 3-Bromo-N-[2,4- dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyridyl)-1 H-pyrazole-5-carboxamide;

M .28.51) N-[4-Chloro-2-[[(1 , 1 -dimethylethyl)amino]carbonyl]-6-methyhphenyl]-1 -(3-chloro-2- pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; or

M.28.6: cyhalodiamide.

7. Agricultural mixtures comprising

a) at least one compound of formula (I) according to any one of the claims 1 to 3, and b) at least one herbicidal compound selected from group b consisting of b1 ) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

b9) mitosis inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11 ) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxinic herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and its salts and esters;including their agriculturally acceptable salts or derivatives.

8. Use of the compound of formula (I) according to any one of the claims 1 to 3 as cyto chrome P450 inhibitor.

9. A method of controlling insects, which are resistant to an insecticide, which method com prises applying to said insects, which are resistant to an insecticide, a composition comprising at least one compound of formula (I), according to any one of the claims 1 to 3 as cytochrome P450 inhibitor and the insecticide, towards which the insects are resistant.

10. The method according to claim 9, wherein the insects, which are resistant to an insecti cide, developed resistance against avermectins, milbemycins, cyclodienes, phosphines, carba mates, pyrethroids, spinosyns, neonicotinoids, diamides, anthranilamide, beta-ketonitrile deriva tives, Tetronic and Tetramic acid derivatives, nereistoxin analogues, acaricides, insect growth regulators or antifeedants.

1 1. The method according to claim 9 or 10, wherein insects, which are resistant to an insecti cide, are from the order Lepidoptera, from the order Coleoptera, from the order Diptera, from the order Thysanoptera, from the order Hemiptera, from the order Hymenoptera, from the order Orthoptera, from the class Arachnida, from the Phylum Nematoda, from the order Isoptera, from the order Blattodea from the order Siphonoptera, from the order Thysanura, from the class Chi- lopoda, from the class Diplopoda, from the class Symphyla, from the order Dermaptera, from the order Collembola, from the order Isopoda, from the order anoplura, from the Phylum Mollus- ca or from the order Phthiraptera.

12. A method of controlling undesired vegetation, which are resistant to an herbicide, which method comprises applying to undesired vegetation, which are resistant to an herbicide, a com position comprising at least one compound of formula (I) according to any one of the claims 1 to 3 as cytochrome P450 inhibitor and the herbicide, towards which undesired vegetation is re sistant.

13. The method according to claim 12, wherein undesired vegetation, which are resistant to an herbicide, developed resistance against herbicide selected from b1 ) lipid biosynthesis inhibitors;

b2) acetolactate synthase inhibitors (ALS inhibitors);

b3) photosynthesis inhibitors;

b4) protoporphyrinogen-IX oxidase inhibitors,

b5) bleacher herbicides;

b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

b7) glutamine synthetase inhibitors;

b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

b9) mitosis inhibitors;

b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);

b11 ) cellulose biosynthesis inhibitors;

b12) decoupler herbicides;

b13) auxinic herbicides;

b14) auxin transport inhibitors; and

b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and its salts and esters;

including their agriculturally acceptable salts or derivatives.

14. The method according to 13, wherein the herbicide is selected from the group consisting of trifluralin, diclofop, Chlorsulfuron, Amitrole, Atrazine, Diuron and Chlorsulfuron.

15. A method for controlling or combating non-crop pests, which are resistant to an insecti cide, comprises applying to said non-crop pests or their food supply, habitat, breeding grounds or their locus, a composition comprising at least one compound of formula (I) according to any one of the claims 1 to 3 as cytochrome P450 inhibitor and the insecticide, towards which non crop pests are resistant.

16. The method according to claim 15, wherein the non-crop pests, which are resistant to an insecticide, developed resistance against insecticides as defined in claim 10.

17. The method according to any one of the claims 15 or 16, wherein non-crop pests, which are resistant to an insecticide, are pests of the classes Chilopoda and Dilopoda and of the or ders Isoptera, Diptera, Blattaria (Blattodea), Dermaptera, Hemiptera, Hymenoptera, Orthoptera, Siphonaptera, Thysanura, Phthiraptera, Araneida, Parasitiformes and Acaridida.

18. Use of a mixture according to claim 5 or 6 for controlling or combating insects and/or non crop pests.

19. Use of a mixture according to claim 7 for controlling or combating undesired vegetation.

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