WO2020120694A1 - Composés hétéroaromatiques bicycliques à action pesticide - Google Patents

Composés hétéroaromatiques bicycliques à action pesticide Download PDF

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WO2020120694A1
WO2020120694A1 PCT/EP2019/084936 EP2019084936W WO2020120694A1 WO 2020120694 A1 WO2020120694 A1 WO 2020120694A1 EP 2019084936 W EP2019084936 W EP 2019084936W WO 2020120694 A1 WO2020120694 A1 WO 2020120694A1
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alkyl
spp
methyl
ccn
optionally substituted
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PCT/EP2019/084936
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Aurelien BIGOT
Jürgen Harry SCHAETZER
Pierre Joseph Marcel Jung
André Stoller
Julien Daniel Henri GAGNEPAIN
Roger Graham Hall
Stefano RENDINE
Nicola COMPAGNONE
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Syngenta Participations Ag
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Publication of WO2020120694A1 publication Critical patent/WO2020120694A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to pesticidally active, in particular insecticidally active fused bicyclic heterocyclic compounds, to compositions comprising those compounds, and to their use for controlling animal pests (including arthropods and in particular insects or representatives of the order Lepidoptera and Hemiptera).
  • Insecticidally-active fused bicyclic heteroaromatic compounds are known, for example, from WO 2013/149903, WO 2007/1 15647, WO 2012/136751 , WO 2013/144088, WO 2013/1501 15, WO 2012/152741 and WO 2014/076272.
  • W is O or S
  • R 1 is Ci-C6alkyl optionally substituted by 1 or 2 substituents independently selected from Ui or a single substituent selected from U2, or Ci-C6haloalkyl optionally substituted by 1 or 2 substituents independently selected from Ui or a single substituent selected from U2;
  • C2-C6alkenyl optionally substituted by 1 or 2 substituents independently selected from Ui or a single substituent selected from U2, or C2-C6haloalkenyl optionally substituted by 1 or 2 substituents independently selected from Ui or a single substituent selected from U2;
  • R 2 is independently selected from halogen, cyano, amino, hydroxyl, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 haloalkoxy, Ci-C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C1-C4 alkylsulfanyl, Ci-C 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 haloalkylsulfanyl, Ci-C 4 haloalkylsulfinyl, Ci- C 4 haloalkylsulfonyl and cyclopropyl;
  • a compound according to Formula (I) as an insecticide, acaricide, nematicide or molluscicide.
  • the use may exclude methods forthe treatment ofthe human or animal body by surgery or therapy.
  • amino means an -NH2 group.
  • Ci-C6alkylsulfanyl refers to a radical of the formula RxS- wherein R x is a Ci-C6alkyl radical as generally defined above.
  • Ci-C6haloalkylaminocarbonyl refers to a Ci-C6alkylaminocarbonyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • U2 is phenyl, thienyl, thiazolyl, pyridinyl, pyrimidinyl or pyrazinyl, each optionally substituted by (i) 1 , 2 or 3 independently selected halogen groups, or (ii) a single L4 group selected from cyano and Ci-C 4 haloalkoxy.
  • U3 is selected from halogen, Ci-C 4 alkyl or Ci-C 4 haloalkyl. More preferably, U3 is selected from fluoro, chloro, bromo, methyl, ethyl, trifluoromethyl.
  • U4 is nitro, cyano, amino, hydroxyl, -SCN, -CO2H, Ci-C 4 alkyl, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkyl-Ci-C 4 alkyl, C3-C6halocycloalkyl-Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 alkoxy, Ci-C 4 alkoxy- Ci-C 4 alkyl, Ci-C 4 alkoxy-Ci-C 4 alkoxy, cyano-Ci-C 4 alkyl, cyano-Ci-C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, Ci-C 4 haloalkoxy, Ci-C 4 haloalk
  • n 0, 1 or 2. In some embodiments of the invention, m is 0. In some embodiments of the invention, m is 1 . In some embodiments of the invention, m is 2. Preferably, m is 0 or 1 , and more preferably, m is 0.
  • R 2 is independently selected from halogen, cyano, amino, hydroxyl, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci- C 4 haloalkoxy, Ci-C 4 alkoxy, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C1-C4 alkylsulfanyl, Ci-C 4 alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 haloalkylsulfanyl, Ci-C 4 haloalkylsulfinyl, Ci- C 4 haloalkylsulfonyl and cyclopropyl.
  • R 3a and R 3b are independently selected from hydrogen, halogen, Ci-C 4 alkyl, Ci-C 4 haloalkyl, Ci- C 4 alkoxy, Ci-C 4 haloalkoxy and cyano.
  • R 3a is hydrogen and R 3b is selected from hydrogen, chloro, fluoro, methyl, ethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, methoxy or ethoxy. More preferably, R 3a is hydrogen and R 3b is hydrogen or methyl. Most preferably, R 3a is hydrogen and R 3b is hydrogen.
  • R 4 is selected from one of Y1 to Y4;
  • R4 is selected from one of Y2 or Y3. In one embodiment of the invention, R4 is Y2. In another embodiment of the invention, R4 is Y3.
  • R 1 is defined in accordance with the present invention, and X represents hydrogen or R 2 as methyl.
  • the compound of Formula (I) is:
  • R 1 is defined in accordance with the present invention, and X represents hydrogen or R 2 as methyl.
  • the compound according to Formula (I) is selected from a compound 1 .001 to 1 .140 listed in Table 1 (below) or a compound A1 to A42 listed in Table A (below).
  • compounds of formula (II) wherein R 2 , R 3a , R 3b , R 4 and m are as defined for formula (I), may be prepared by the reaction of a compound of formula (III) and a compound of formula (IV), wherein LG is a leaving group such as, for example, halide, in the presence, or not, of a suitable base, such as for example sodium carbonate, potassium carbonate or cesium carbonate, or lithium alkoxide, sodium alkoxide or potassium alkoxide, in suitable solvents that may include, for example, acetonitrile, DMF, 1 ,4-dioxane, and usually upon heating of the reaction mixture at temperatures between room temperature and 200°C, and preferably between 20°C to the boiling point of the reaction mixture, optionally under microwave heating conditions.
  • a catalyst may be used in this reaction, including sodium iodide or tert-butylammonium iodide.
  • compounds of formula (III) could be prepared as described in Scheme 2.
  • compounds of formula (III) wherein R 2 and m are defined as forformula (I) may be prepared by a Curtius rearrangement from compounds of formula (X) which are commercially available, wherein R 2 and m are as described for formula (I), by treatment with diphenylphosphoryl azide (DPPA), in the presence of a suitable base, such as for example trimethylamine, in suitable solvents that may include, for example, ethanol, tert-butanol, 1 ,4-dioxane, tetrahydrofuran, usually upon heating at temperatures between room temperature and 200°C, and preferably between 20°C to the boiling point of the reaction mixture.
  • DPPA diphenylphosphoryl azide
  • suitable solvents that may include, for example, ethanol, tert-butanol, 1 ,4-dioxane, tetrahydrofuran, usually upon heating at temperatures between room temperature and 200°
  • compounds of formula (II) wherein R 2 , R 3a , R 3b , R 4 and m are defined as forformula (I) can be prepared by the reaction of compounds of formula (V) and compounds of formula (VI), wherein LGi and LG2 are independently leaving groups, such as, for example, halide, an aryloxy group or imidazolyl group.
  • the reaction can be performed at 0°C to the boiling point of the solvent and preferably in the presence, or not, of a base, which may be, for example, ammonia, pyridine, Hiinig’s base, triethylamine or sodium carbonate and in a solvent such as, for example, dichloromethane or a mixture of solvents, such as methanol and dichloromethane
  • a base which may be, for example, ammonia, pyridine, Hiinig’s base, triethylamine or sodium carbonate
  • a solvent such as, for example, dichloromethane or a mixture of solvents, such as methanol and dichloromethane
  • Compounds of formula (V) wherein R 2 , R 3a , R 3b , R 4 and m are defined as for formula (I) may be prepared by the hydrolysis of compounds of formula (IX) by treatment with a suitable strong acid, such as, for example a 37% concentrated aqueous solution of HCI, usually upon heating at temperatures between room temperature and 200°C, and preferably between 20°C to the boiling point of the reaction mixture, and optionally under microwave heating conditions.
  • a suitable strong acid such as, for example a 37% concentrated aqueous solution of HCI
  • compounds of formula (V) wherein R 2 , R 3a , R 3b R 4 and m are defined as forformula (I) may be prepared by the hydrolysis of compounds of formula (VIII), by treatment with a suitable strong acid, like, for example a 37% concentrated aqueous solution of hydrogen bromide, usually upon heating at temperatures between room temperature and 200°C, preferably between 20°C to the boiling point of the reaction mixture, and optionally under microwave heating conditions.
  • a suitable strong acid like, for example a 37% concentrated aqueous solution of hydrogen bromide
  • Compounds of formula (IX) wherein R 2 , R 3a , R 3b R 4 and m are defined as for formula (I), may be prepared by hydrolysis of compounds of formula (VIII) by treatment with a suitable acid, such as, for example trifluoroacetic acid (TFA), in suitable solvents that may include, for example, dichloromethane or 1 ,2-dichloroethane, and usually upon heating at temperatures between room temperature and 200°C, preferably between 20°C to the boiling point of the reaction mixture, optionally under microwave heating conditions.
  • a suitable acid such as, for example trifluoroacetic acid (TFA)
  • suitable solvents may include, for example, dichloromethane or 1 ,2-dichloroethane, and usually upon heating at temperatures between room temperature and 200°C, preferably between 20°C to the boiling point of the reaction mixture, optionally under microwave heating conditions.
  • Compounds of formula (VIII) wherein R 2 , R 3a , R 3b R 4 and m are as defined for formula (I), may be prepared by reaction between compounds of formula (VII) and compounds of formula (IV), wherein LG is a leaving group such as, for example, halide, in the presence, or not, of a suitable base, such as for example sodium carbonate, potassium carbonate or cesium carbonate, or lithium ethanoate, sodium ethanoate or potassium ethanoate, in suitable solvents that may include, for example, acetonitrile, DMF, 1 ,4-dioxane, and usually upon heating at temperatures between room temperature and 200°C, preferably between 20°C to the boiling point of the reaction mixture, and optionally under microwave heating conditions.
  • a suitable base such as for example sodium carbonate, potassium carbonate or cesium carbonate, or lithium ethanoate, sodium ethanoate or potassium ethanoate
  • suitable solvents may include, for example, acet
  • compounds of formula (VII) wherein R 2 and m are defined as for formula (I) may be prepared from compounds of formula (XII) by treatment with, for example, di-tert-butyl dicarbonate ((BOC)20), in a suitable solvent that may include, for example, dichloromethane, 1 ,2-dichloroethane, tetrahydrofuran or by performing the reaction in molten di-tert-butyl dicarbonate, usually upon heating at temperatures between room temperature and 200°C, and preferably between 20°C to the boiling point of the reaction mixture.
  • An alternative protecting group could be used such as, eg, benzyl.
  • Compounds of formula (XII) may be prepared by the reaction of compounds of formula (XI) and compounds of formula (XIII), wherein LGi and LG2 are independently from each other leaving groups, like, for example amino, halide or imidazole.
  • the reaction can be performed at 0°C to the boiling point of the solvent and preferably in the presence of a base, which could be, for example, pyridine, Hiinig’s base, triethylamine or sodium carbonate.
  • a base which could be, for example, pyridine, Hiinig’s base, triethylamine or sodium carbonate.
  • Compounds of formula (XV) wherein R 2 , R 1 and m are defined as for formula (I) can be prepared by the reaction of compounds of formula (XIV) and compounds of formula (VI), wherein LGi and LG2 are independently from each other leaving groups, such as, for example, halide such as chloride, an aryloxy group or imidazolyl.
  • the reaction can be performed at 0°C to the boiling point of the solvent and preferably in the presence of a base, which may be, for example, pyridine, Hiinig’s base, triethylamine or sodium carbonate.
  • compounds of formula (XV) wherein R 2 , R 3a , R 3b , R 4 and m are defined as for formula (I) can be prepared by the reaction of compounds of formula (XIV) and compounds of formula (VI), wherein LGi and LG2 are identical such as, for example urea.
  • the reaction can be performed at 50°C to 200°C or to the boiling point of the reaction mixture. In presence or not of a solvent such as dimethyl formamide or tetrahydrofuran.
  • Examples which may be mentioned are sodium hydroxide, sodium hydride, sodium amide, sodium methoxide, sodium acetate, sodium carbonate, potassium tert-butoxide, potassium hydroxide, potassium carbonate, potassium hydride, lithium diisopropylamide, potassium bis(trimethylsilyl)amide, calcium hydride, triethylamine, diisopropylethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N,N-dimethylamine, N,N- diethylaniline, pyridine, 4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine, benzyltrimethylammonium hydroxide and 1 ,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
  • DBU ,8-diazabicyclo[5.4.0]undec-7-ene
  • Reactions are advantageously carried out in a temperature range from approximately -80 °C to approximately 140 °C, preferably from approximately -30 °C to approximately 100 °C, in many cases in the range between ambient temperature and approximately 80 °C.
  • a compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) in the customary manner by (an)other substituent(s) according to the invention.
  • Salts of compounds of formula (I) can be prepared in a manner known per se.
  • acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion exchanger reagent and salts with bases are obtained by treatment with a suitable base or with a suitable ion exchanger reagent.
  • Salts of compounds of formula (I) can be converted in the customary manner into the free compounds (I), acid addition salts, for example, by treatment with a suitable basic compound or with a suitable ion exchanger reagent and salts with bases, for example, by treatment with a suitable acid or with a suitable ion exchanger reagent.
  • Salts of compounds of formula (I) can be converted in a manner known per se into other salts of compounds of formula (I), acid addition salts, for example, into other acid addition salts, for example by treatment of a salt of inorganic acid such as hydrochloride with a suitable metal salt such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt which forms, for example silver chloride, is insoluble and thus precipitates from the reaction mixture.
  • a salt of inorganic acid such as hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the compounds of formula (I), which have salt-forming properties can be obtained in free form or in the form of salts.
  • the compounds of formula (I) and, where appropriate, the tautomer’s thereof, in each case in free form or in salt form, can be present in the form of one of the isomers which are possible or as a mixture of these, for example in the form of pure isomers, such as antipodes and/or diastereomers, or as isomer mixtures, such as enantiomer mixtures, for example racemates, diastereomer mixtures or racemate mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms which occur in the molecule and/or depending on the configuration of non-aromatic double bonds which occur in the molecule, the invention relates to the pure isomers and also to all isomer mixtures which are possible and is to be understood in each case in this sense hereinabove and herein below, even when stereochemical details are not mentioned specifically in each case.
  • Diastereomeric mixtures or racemic mixtures of compounds of formula (I), in free form or in salt form, which can be obtained depending on which starting materials and procedures have been chosen can be separated in a known manner into the pure diastereomers or racemates on the basis of the physicochemical differences of the components, for example by fractional crystallization, distillation and/or chromatography.
  • Enantiomeric mixtures such as racemates, which can be obtained in a similar manner can be resolved into the optical antipodes by known methods, for example by recrystallization from an optically active solvent, by chromatography on chiral adsorbents, for example high-performance liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific, immobilized enzymes, via the formation of inclusion compounds, for example using chiral crown ethers, where only one enantiomer is complexed, or by conversion into diastereomeric salts, for example by reacting a basic end-product racemate with an optically active acid, such as a carboxylic acid, for example camphor, tartaric or malic acid, or sulfonic acid, for example camphorsulfonic acid, and separating the diastereomer mixture which can be obtained in this manner, for example by fractional crystallization based on their differing solubilities, to give the di
  • Pure diastereomers or enantiomers can be obtained according to the invention not only by separating suitable isomer mixtures, but also by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials of a suitable stereochemistry.
  • the biologically more effective isomer for example enantiomer or diastereomer, or isomer mixture, for example enantiomer mixture or diastereomer mixture, if the individual components have a different biological activity.
  • the compounds of formula (I) and, where appropriate, the tautomers thereof, in each case in free form or in salt form, can, if appropriate, also be obtained in the form of hydrates and/or include other solvents, for example those which may have been used for the crystallization of compounds which are present in solid form.
  • the compounds of formula (I) according to the invention are preventively and/or curatively valuable active ingredients in the field of pest control, even at low rates of application, which have a very favorable biocidal spectrum and may be well-tolerated by warm-blooded species, fish and plants.
  • the compounds of formula (I) may have a beneficial safety profile towards non-target species, such as bees, and accordingly a good toxicity profile.
  • the active ingredients according to the invention may act against all or individual developmental stages of normally sensitive, but also resistant pests, such as insects or representatives of the order Acarina.
  • the insecticidal or acaricidal activity of the active ingredients according to the invention can manifest itself directly, i. e. in destruction of the pests, which takes place either immediately or only after some time has elapsed, for example during ecdysis, or indirectly, for example in a reduced oviposition and/or hatching rate.
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp., from the order Coleoptera, for example,
  • Agriotes spp. Amphimallon majale, Anomala orientalis, Anthonomus spp., Aphodius spp., Astylus atromaculatus, Ataenius spp., Atomaria linearis, Chaetocnema tibialis, Cerotoma spp., Conoderus spp., Cosmopolites spp., Cotinis nitida, Curculio spp., Cyclocephala spp., Dermestes spp., Diabrotica spp., Diloboderus abderus, Epilachna spp., Eremnus spp., Heteronychus arator, Hypothenemus hampei, Lagria vilosa, Leptinotarsa decemLineata, Lissorhoptrus spp., Liogenys spp., Maecolaspis spp., Maladera
  • Thysanoptera for example
  • the invention may also relate to a method of controlling damage to plant and parts thereof by plant parasitic nematodes (Endoparasitic-, Semiendoparasitic- and Ectoparasitic nematodes), especially plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne arenaria and other Meloidogyne species, cyst-forming nematodes, Globodera rostochiensis and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species, Seed gall nematodes, Anguina species, Stem and foliar nematodes, Aphelenchoides species, Sting nematodes, Belonolai
  • H. aperta Limax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus), Lymnaea, Milax (M. gagates, M. marginatus, M. sowerbyi), Opeas, Pomacea (P. canaticulata), Vallonia and Zanitoides.
  • Compounds according to Formula (I) may find utility in controlling resistant populations of insects previously sensitive to the neonicotinoid class of pesticidal (insecticidal) agents (the “neonicotinoids”). Accordingly, the present invention may relate to a method of controlling insects which are resistant to a neonicotinoid insecticide comprising applying a compound of Formula (I) (eg, a single compound selected from compounds 1 .001 to 1 .140 listed in Table 1 (below) or a compound A1 to A42 listed in Table A (below)) to a neonicotinoid-resistant insect.
  • a compound of Formula (I) eg, a single compound selected from compounds 1 .001 to 1 .140 listed in Table 1 (below) or a compound A1 to A42 listed in Table A (below)
  • the present invention may relate to the use of a compound of Formula (I) (eg, a single compound selected from compounds 1 .001 to 1 .140 listed in Table 1 (below) or a compound A1 to A42 listed in Table A (below) as an insecticide against neonicotinoid-resistant insects.
  • a compound of Formula (I) eg, a single compound selected from compounds 1 .001 to 1 .140 listed in Table 1 (below) or a compound A1 to A42 listed in Table A (below) as an insecticide against neonicotinoid-resistant insects.
  • Such neonicotinoid-resistant insects may include insects from the order Lepidoptera or Hemiptera, in particular from the family Aphididae.
  • 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 containing an insecticidal active ingredient to achieve the expected level of control when used according to the label recommendation for that pest species” (IRAC).
  • Cross- resistance occurs when resistance to one insecticide confers resistance to another insecticide via the same biochemical mechanism. This can happen within insecticide chemical groups or between insecticide chemical groups. Cross- resistance may occur even if the resistant insect has never been exposed to one of the chemical classes of insecticide.
  • Xenorhabdus spp. such as Photorhabdus luminescens, Xenorhabdus nematophilus, toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins, toxins produced by fungi, such as Streptomycetes toxins, plant lectins, such as pea lectins, barley lectins or snowdrop lectins, agglutinins, proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors, ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin, steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP- glycosyl-transferase, cholesterol oxidases, ecd
  • 5-endotoxins for example CrylAb, CrylAc, Cry1 F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1 , Vip2, Vip3 or Vip3A
  • Vip vegetative insecticidal proteins
  • Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701 ).
  • Truncated toxins for example a truncated CrylAb, are known.
  • Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.
  • Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651 .
  • the toxin contained in the transgenic plants imparts to the plants tolerance to harmful insects.
  • insects can occur in any taxonomic group of insects, but are especially commonly found in the beetles (Coleoptera), two-winged insects (Diptera) and moths (Lepidoptera).
  • transgenic crops are:
  • MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G- protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.
  • MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a Cry3Bb1 toxin and has resistance to certain Coleoptera insects.
  • NK603 x MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1 150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810.
  • NK603 c MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylAb toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, include the European corn borer.
  • crops is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225).
  • PRPs pathogenesis-related proteins
  • Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191 .
  • the methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.
  • Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.
  • fungal for example Fusarium, Anthracnose, or Phytophthora
  • bacterial for example Pseudomonas
  • viral for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus
  • Crops that are tolerance to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.
  • Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins, stilbene synthases, bibenzyl synthases, chitinases, glucanases, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225), antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).
  • ion channel blockers such as blockers for sodium and calcium channels
  • the viral KP1 , KP4 or KP6 toxins stilbene synthases, bibenzyl synthases, chitinases, glucanases, the so-called
  • compositions according to the invention are the protection of stored goods and store ambients and the protection of raw materials, such as wood, textiles, floor coverings or buildings, and also in the hygiene sector, especially the protection of humans, domestic animals and productive livestock against pests of the mentioned type.
  • compositions to a substrate such as non-woven or a fabric material in the form of (or which can be used in the manufacture of) netting, clothing, bedding, curtains and tents.
  • a substrate selected from nonwoven and fabric material comprising a composition which contains a compound of formula I.
  • compositions according to the invention are the field of tree injection/trunk treatment for all ornamental trees as well all sort of fruit and nut trees.
  • the compounds according to the present invention are especially suitable against wood-boring insects from the order Lepidoptera as mentioned above and from the order Coleoptera, especially against woodborers listed in the following Table:
  • the present invention may be also used to control any insect pests that may be present in turfgrass, including for example beetles, caterpillars, fire ants, ground pearls, millipedes, sow bugs, mites, mole crickets, scales, mealybugs ticks, spittlebugs, southern chinch bugs and white grubs.
  • the present invention may be used to control insect pests at various stages of their life cycle, including eggs, larvae, nymphs and adults.
  • the present invention may be used to control insect pests that feed on the roots of turfgrass including white grubs (such as Cyclocephala spp. (e.g. masked chafer, C. lurida), Rhizotrogus spp. (e.g. European chafer, R. majalis), Cotinus spp. (e.g. Green June beetle, C. nitida), Popillia spp. (e.g. Japanese beetle, P. japonica), Phyllophaga spp. (e.g. May/June beetle), Ataenius spp. (e.g. Black turfgrass ataenius, A.
  • white grubs such as Cyclocephala spp. (e.g. masked chafer, C. lurida), Rhizotrogus spp. (e.g. European chafer, R. majalis), Cotinus spp
  • the present invention may also be used to control insect pests ofturfgrass that live above the ground and feed on the turfgrass leaves, including chinch bugs (such as southern chinch bugs, Blissus insularis), Bermudagrass mite (Eriophyes cynodoniensis), rhodesgrass mealybug (Antonina graminis), two-lined spittlebug ( Propsapia bicincta), leafhoppers, cutworms ( Noctuidae family), and greenbugs.
  • chinch bugs such as southern chinch bugs, Blissus insularis
  • Bermudagrass mite Eriophyes cynodoniensis
  • rhodesgrass mealybug Antonina graminis
  • two-lined spittlebug Propsapia bicincta
  • leafhoppers Tricotuidae family
  • cutworms Noctuidae family
  • the active ingredients can also be contained in very fine microcapsules.
  • Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release).
  • Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • an algicide selected from the group of substances consisting of bethoxazin [CCN] + TX, copper dioctanoate (lUPAC name) (170) + TX, copper sulfate (172) + TX, cybutryne [CCN] + TX, dichlone (1052) + TX, dichlorophen (232) + TX, endothal (295) + TX, fentin (347) + TX, hydrated lime [CCN] + TX, nabam (566) + TX, quinoclamine (714) + TX, quinonamid (1379) + TX, simazine (730) + TX, triphenyltin acetate (lUPAC name) (347) and triphenyltin hydroxide (lUPAC name) (347) + TX,
  • TX Steinernematid spp. (Guardian Nematodes®) + TX, Stethorus punctillum (Stethorus®) + TX, Tamarixia radiate + TX, Tetrastichus setifer + TX, Thripobius semiluteus + TX, Torymus sinensis + TX, Trichogramma brassicae (Tricholine b®) + TX, Trichogramma brassicae (Tricho-Strip®) + TX, Trichogramma evanescens + TX, Trichogramma minutum + TX, Trichogramma ostriniae + TX, Trichogramma platneri + TX, Trichogramma pretiosum + TX, Xanthopimpla stemmator, and other biologicals including: abscisic acid + TX, bioSea® + TX, Chondrostereum purpureum (Chontrol Paste®) + TX, Colletotrichum gloeosporio

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un composé de formule (I) dans laquelle les substituants sont tels que définis dans la revendication 1, et des sels, stéréoisomères, énantiomères, tautomères et N-oxydes acceptables sur le plan agrochimique de ces composés, utiles en tant qu'insecticides.
PCT/EP2019/084936 2018-12-14 2019-12-12 Composés hétéroaromatiques bicycliques à action pesticide WO2020120694A1 (fr)

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WO2012152741A1 (fr) 2011-05-10 2012-11-15 Bayer Intellectual Property Gmbh (thio)carbonylamidines bicycliques
WO2013144088A1 (fr) 2012-03-29 2013-10-03 Basf Se Composés hétéro-bicycliques n-substitués et dérivés pour la lutte contre animaux nuisibles
WO2013149903A1 (fr) 2012-04-03 2013-10-10 Basf Se Dérivés furanones hétéro-bicycliques n-substituées pour combattre un animal
WO2013150115A1 (fr) 2012-04-05 2013-10-10 Basf Se Composés hétéro-bicycliques et dérivés pour combattre les animaux nuisibles
WO2014076272A1 (fr) 2012-11-16 2014-05-22 Syngenta Participations Ag Composés pesticides

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