WO2014082879A1 - Composés de [1,2,4]triazole substitués - Google Patents

Composés de [1,2,4]triazole substitués Download PDF

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WO2014082879A1
WO2014082879A1 PCT/EP2013/074008 EP2013074008W WO2014082879A1 WO 2014082879 A1 WO2014082879 A1 WO 2014082879A1 EP 2013074008 W EP2013074008 W EP 2013074008W WO 2014082879 A1 WO2014082879 A1 WO 2014082879A1
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compounds
alkyl
line
combination
cycloalkyl
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PCT/EP2013/074008
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Wassilios Grammenos
Ian Robert CRAIG
Nadege Boudet
Bernd Müller
Jochen Dietz
Erica May Wilson LAUTERWASSER
Jan Klaas Lohmann
Thomas Grote
Egon Haden
Ana Escribano Cuesta
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Basf Se
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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

Definitions

  • the present invention relates to substituted [1 ,2,4]triazol compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound.
  • the invention also relates to processes for preparing these compounds, intermediates, processes for preparing preparing such intermediates, and to compositions comprising at least one compound I.
  • EP 0 126 430 A2 relates to a process for the preparation of 1 -triazolylethylether derivatives.
  • EP 0 1 13 640 A2 relates to 1 -azolyl-2-aryl-3-fluoroalkan-2-ols as microbiocides.
  • DE 3801233 relates to 1 -phenoxyphenyl-2-triazolyl-ethanolethers as microbiocides.
  • EP 0 275 955 A1 relates to 1 -phenoxyphenyl-1 -triazolylmethyl-carbinols as microbiocides having the formula
  • GB 2 130 584 A is directed to microbiocidal 1 -carbonyl- 1 -phenoxyphenyl-2-azolylethanol-derivatives.
  • PCT/EP2012/063526, PCT/EP2012/063635, PCT/EP2012/063620, PCT/EP2012/065835, PCT/EP2012/065834, PCT/EP2012/065850, PCT/EP2012/065836, PCT/EP2012/065848, PCT/EP2012/065847, PCT/EP2012/065852 and EP 1 1 177556.5 are directed to specific fungicidal substituted 2-[2-halogen-4-phenoxy-phenyl]-1 - [1 ,2,4]triazol-1 -yl-ethanol compounds.
  • WO 2013/007767 A1 (PCT/EP2012/063626) is directed to fungicidal substituted 2-[2-halogenalkyl-4-phenoxy-phenyl]-1 -[1 ,2,4]-triazol-1 -yl-ethanol compounds.
  • J. Agric. Food. Chem. 2009, 57, 4854-4860 relates to the synthesis and fungicidal evaluation of certain 2-arylphenyl ether-3-(1 H-1 ,2,4-triazol-1 -yl)propan-2-ol derivatives.
  • the compounds of this reference always contain exactly one substituent, namely always 2-chloro, in the inner phenyl.
  • EP 0 440 950 A2 is directed to halgenallyl-azolyl-derivatives of the formula
  • R 1 can be, for example, a (substituted) phenoxy-phenyl unit, that is, however, always either unsubstituted or only mono-substituted in the inner phenyl- ring that is next to the alcohol/carbon atom of the basic structure.
  • EP 0 1 17 378 relates to 1 -carbonyl-1 -phenoxyphenyl-2-azolyl-ethanol derivatives as microbiocides and intermediates therefor.
  • EP 0 077 479 relates to phenoxyphenyl-azolylmethyl-ketons and -carbinols, processes for their preparation and their useas fungicides and intermediates.
  • the fungicidal activity of the known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phyto- pathogenic harmful fungi.
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl- Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl;
  • R 2 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl- Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl;
  • aliphatic moieties of R 1 and/or R 2 may carry one, two, three or up to the maximum possible number of identical or different groups R 12a which independently of one another are selected from:
  • R 12a halogen, OH, CN, nitro, Ci-C4-alkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C1-C4- halogenalkoxy;
  • cycloalkyl and/or phenyl moieties of R 1 and/or R 2 may carry one, two, three, four, five or up to the maximum number of identical or different groups R 12b which independently of one another are selected from:
  • R 12b halogen, OH, CN, nitro, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl and Ci-C4-halogenalkoxy;
  • R 31 is halogen
  • n is 1 , 2 or 3;
  • R 3 is independently selected from halogen, CN, NO2, OH, SH, Ci-C6-alkyl, Ci-C6-alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , S(0) P (Ci-C 4 -alkyl),
  • R 3a is independently selected from halogen, CN, N0 2 , OH, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C 3 -C 3 - cycloalkyl, C 3 -C8-halocycloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -haloalkoxy; and wherein
  • p 0, 1 or 2;
  • n 0, 1 , 2, 3, 4 or 5;
  • R 4 is independently selected from the substituents as defined for R 3 ; wherein said R 4 are un- substituted or further substituted by one, two, three or four R 4a , wherein each R 4a is independently selected from the substituents as defined for R 3a ;
  • the compounds according to the present invention structurally differ from those described in the abovementioned publications inter alia because of the specific substitution pattern of the inner phenyl ring carrying ortho-halogen as R 31 and at least one further substituent.
  • the compounds I can be obtained by various routes in analogy to prior art processes known (cf. J.Agric. Food Chem. (2009) 57, 4854-4860; EP 0 275 955 A1 ; DE 40 03 180 A1 ; EP 0 1 13 640 A2; EP 0 126 430 A2) and by the synthesis routes shown in the following schemes and in the experimental part of this application.
  • the resulting compounds IVa , in particular IV are then transformed into Grignard reagents by the reaction with transmetallation reagents such as iso- propylmagnesium halides and subsequently reacted with acetyl chloride preferably under anhydrous conditions and preferably in the presence of a catalyst such as CuCI, CuCI 2 , AICI3, LiCI and mixtures thereof, in particular CuCI, to obtain acetophenones V.
  • transmetallation reagents such as iso- propylmagnesium halides
  • acetyl chloride preferably under anhydrous conditions and preferably in the presence of a catalyst such as CuCI, CuCI 2 , AICI3, LiCI and mixtures thereof, in particular CuCI
  • These compounds V can be halogenated e.g. with bromine, preferably in an organic solvent such as diethyl ether, methyl tert. -butyl ether (MTBE), methanol or acetic acid.
  • organic solvent such as diethyl ether, methyl tert. -butyl ether (MTBE), methanol or acetic acid.
  • halogen such as e.g. Br or CI.
  • Compounds VI can subsequently reacted with 1 H-1 ,2,4-triazole preferably in the presence of a solvent such as tetrahydrofuran (THF), dimethylformamide (DMF), toluene, and in the presence of a base such as potassium carbonate, sodium hydroxide or sodium hydride to obtain comounds VII.
  • a solvent such as tetrahydrofuran (THF), dimethylformamide (DMF), toluene
  • a base such as potassium carbonate, sodium hydroxide or sodium hydride
  • These triazole keto compounds VII can be reacted with a Grignard reagent such as R 1 MgBr or an organolithium reagent R 1 Li preferably under anhydrous conditions to obtain compounds I wherein R 2 is hydrogen, which compounds are of formula 1.1.
  • a Lewis acid such as LaC x2 LiCI or MgBr2xOEt2 can be used. If appropriate, these compounds 1.1 can subsequently be transformed e.g.
  • LG represents a nucleophilically replaceable leaving group such as halogen, alkylsulfonyl, alkylsulfonyloxy and arylsulfonyloxy, preferably chloro, bromo or iodo, particularly preferably bromo, preferably in the presence of a base, such as for example, NaH in a suitable solvent such as THF, to form other compounds I.
  • a base such as for example, NaH in a suitable solvent such as THF
  • a halo derivative Ilia wherein X 2 is halogen, in particular F, and X 3 is halogen, in particular Br, is reacted with a transmetallation agent such as e.g. isopropylmagnesium bromide followed by an acyl chloride agent R 1 COCI (e.g. acetyl chloride) preferably under anhydrous conditions and optionally in the presence of a catalyst such as CuCI, CuC , AlC , LiCI and mixtures thereof, in articular CuCI, to obtain ketones VIII.
  • a transmetallation agent such as e.g. isopropylmagnesium bromide
  • R 1 COCI e.g. acetyl chloride
  • a catalyst such as CuCI, CuC , AlC , LiCI and mixtures thereof, in articular CuCI
  • ketones VIII are reacted with phenoles II preferably in the presence of a base to obtain compounds Va wherein R 1 is as defined and preferably defined, respectively, herein.
  • Compounds Va may also be obtained in analogy to the first process described for compounds V (preferred conditions for the process step, see above . This is illustrated as follows:
  • Ethers IVb can be synthesized by nucleophilic substitution of X group in compound Illc (An- revieweddte Chemie, International Edition, 45(35), 5803-5807; 2006, US 20070088015 A1 , Jour- nal of the American Chemical Society, 134(17), 7384-7391 ; 2012 ). Then, a Lewis acid catalyzed addition of an acid halide, preferably will lead to compounds Va (Journal of Chemical Research, Synopses, (8), 245; 1992, WO2010096777 A1 ).
  • intermediates Va are reacted with trimethylsulf(ox)onium halides, preferably iodide, preferably in the presence of a base such as sodium hydroxide.
  • the epoxide ring of intermediates IX is cleaved by reaction with alcohols R 2 OH referably under acidic conditions.
  • halogenating agents or sulfonating agents such as PBr3, PC mesyl chloride, tosyl chloride or thionyl chloride, to obtain compounds XI wherein LG is a nucleophilically replaceable leaving group such as halogen, alkyl- sulfonyl, alkylsulfonyloxy and arylsulfonyloxy, preferably chloro, bromo or iodo, particularly preferably bromo or alkylsulfonyl.
  • compounds XI are reacted with 1 H-1 ,2,4-triazole to obtain compounds I. halogenating or sulfonating agent
  • inventive compounds cannot be directly obtained by the routes described above, they can be prepared by derivatization of other inventive compounds.
  • the N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or oxone (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ).
  • the oxidation may lead to pure mono-N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
  • the variables R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Formulae I .A, I.B, I.C in combination with Table B below, wherein each line of lines B-1 to B-1536 of Table B corresponds to one specific embodiment for (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m.
  • the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formulae Va and V (see above), wherein the variables R 1 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined and preferably defined for formula I herein.
  • variables R 1 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Tables 1 a to 70a, Tables 1 b to 70b and Tables 1 c to 70c for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula VI (see above), wherein variables R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are are as defined and preferably defined for formula I herein, and wherein Hal stands for halogen, in particular CI or Br. According to one preferred embodiment, Hal in compounds VI stands for Br.
  • the variables R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Formulae I.A, I.B, I.C in combination with Table B below, wherein each line of lines B-1 to B-1536 of Table B corresponds to one specific embodiment for (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m.
  • the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula VII (see above), wherein the variables variables R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined and preferably de- fined for formula I herein.
  • the variables R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Formulae I.A, I.B, I.C in combination with Table B below, wherein each line of lines B-1 to B-1536 of Table B corresponds to one specific embodiment for (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m.
  • the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula IX (see above), wherein the variables R 1 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined and preferably defined for formula I herein.
  • the variables R 1 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Tables 1 a to 70a, Tables 1 b to 70b and Tables 1 c to 70c for compounds I, wherein the substituents are specific embodi- ments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula X, wherein the variables R 1 , R2, R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined and preferably defined for formula I herein.
  • the variables R 1 , R 2 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Tables 1 a to 70a, Tables 1 b to 70b and Tables 1 c to 70c for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • a further embodiment of the present invention is compounds of formula XI, wherein the variables R 1 , R 2 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined and preferably defined for formula I herein, and LG stands for a leaving group as defined above.
  • the variables R 1 , R 2 , R 31 , (R 3 ) n (R 32 , R 33 , R 34 ), R 4 and m are as defined in Tables 1 a to 70a, Tables 1 b to 70b and Tables 1 c to 70c for compounds I, wherein the substituents are specific embodiments independently of each other or in any combination.
  • C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
  • halogen refers to fluorine, chlorine, bromine and iodine.
  • Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl,
  • Ci-C4-alkyl refers to a straight-chained or branched alkyl group having 1 to 4 carbon atoms, such as methyl, ethyl, propyl (n-propyl), 1 -methylethyl (iso- propoyl), butyl, 1 -methylpropyl (sec.
  • C2-C4-alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1 -methylethyl (iso-propoyl), butyl, 1 - methylpropyl (sec. -butyl), 2-methylpropyl (iso-butyl), 1 ,1 -dimethylethyl (tert. -butyl).
  • Ci-C6-haloalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Examples are "Ci-C2-haloalkyl” groups such as chloromethyl, bro- momethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro- fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 - fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,
  • C2-C6-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical 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 (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
  • C2-C6-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- alkynyl” groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl (propargyl), but-1 -ynyl, but-2-ynyl, but-3-ynyl, 1 -methyl-prop-2-ynyl.
  • Cs-Cs-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 8 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • C3-C8-cycloalkyl-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
  • Ci-C6-alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group.
  • Examples are “C1-C4- alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 - methyhpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
  • Ci-C4-alkoxy refers to a straight-chain or branched alkyl group having 1 to 4 carbon atoms which is bonded via an oxygen, at any position in the alkyl group, examples are methoxy, ethoxy, n-propoxy, 1 - methylethoxy, butoxy, 1 -methyhpropoxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
  • Ci-C6-haloalkoxy refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
  • Examples are "Ci-C4-haloalkoxy” groups, such as OCH2F, OCH F2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoro- ethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-tri- chloro-"ethoxy, OC2F5, 2-fluoro
  • OCF2-C2F5 1 -fluoromethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2- bromo-'ethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
  • phenyl-Ci-C6-alkyl refers to alkyl having 1 to 6 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a phenyl radical.
  • phenyl-C2-C6-alkenyl and “phenyl-C2-C6-alkynyl” refer to alkenyl and alkynyl, respectively, wherein one hydrogen atom of the aforementioned radicals is replaced by a phenyl radical.
  • Ci-C4-alkoxy-Ci-C6-alkyl refers to alkyl having 1 to 6 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy radical having 1 to 4 carbon atoms (as defined above).
  • Ci-C4-alkoxy-C2-C6-alkenyl refers to alkenyl having 2 to 6 carbon atoms (as defined above), wherein one hydrogen atom of the alkenyl radical is replaced by a Ci-C4-alkoxy radical having 1 to 4 carbon atoms (as defined above).
  • Ci-C4-alkoxy-C2-C6-alkynyl refers to alkynyl having 2 to 6 carbon atoms (as defined above), wherein one hydrogen atom of the alkynyl radical is replaced by a Ci-C4-alkoxy radical having 1 to 4 carbon atoms (as defined above).
  • Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds.
  • Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammoni- um, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phos- phonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, prefer- ably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, prefera- bly of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
  • the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure diastereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
  • R 1 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3- Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl, wherein the aliphatic moieties of R 1 may carry one, two, three or up to the maximum possible number of identical or different groupsR 123 which independently of one another are selected from halogen, OH, CN, nitro, Ci-C4-alkoxy, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl and Ci-C4-halogenalkoxy; and wherein the cycloalkyl and/or phenyl moieties of R 1 may carry one,
  • R 1 is selected from hydrogen, Ci-C6-alkyl, C1-C4- alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-C2- C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-Ci- C4-alkoxy-Ci-C4-alkyl, phenyl-C2-C6-alkenyl, phenyl-Ci-C4-alkoxy-C2-C6-alkenyl, phenyl-C2-C6- alkynyl, phenyl-Ci-C4-alkoxy-C2-C6-alkeny
  • R 1 is selected from hydrogen, Ci-C6-alkyl, Ci-C4-alkoxy-Ci- C6-alkyl, C2-C6-alkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, C3-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C6-alkyl, wherein the aliphatic moieties of R 1 are not further substituted or carry one, two or three identical or different groups R 12a1 which independently of one another are selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C4-halogenalkoxy; and wherein the cycloalkyl moieties of R 1 may carry one, two, three, four or five identical or different groups R 12a1 which independently
  • R 1 is H.
  • R 1 is selected from Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyI, C3-C8-cycloalkyl-Ci-C4-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl and phenyl-C2-C4-alkynyl, wherein the R 1 are in each case unsubstituted or are substituted by R 12a and/or R 12b as defined and preferably defined herein. Specific embodiments thereof can be found in the below Table P1.
  • R 1 is Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, C1-C4- alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, Cs-Cs-cycloalkyI, C3-C8- cycloalkyl-Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl-C2- C6-alkenyl, phenyl-Ci-C4-alkoxy-C2-C6-alkenyl, phenyl-C2-C6-alkynyl, phenyl-Ci-C4-alkoxy-C2- C6-alkynyl,
  • R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C 4 -alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, Ci-C 4 -alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C 4 -alkoxy-C2-C6- alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl, phenyl, phenyl-Ci-C 4 -alkyl, phenyl-Ci-C 4 - alkoxy-Ci-C 4 -alkyl, phenyl-C2-C6-alkenyl, phenyl-Ci-C 4 -alkoxy-C2-C6-alkenyl, phenyl-C2-C6-alkeny
  • R 1 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as CH3, C2H5, CH(CH3)2 or C(CH3)3. According to one embodiment, this R 1 is not further substituted.
  • a further embodiment relates to compounds, wherein R 1 is Ci-C6-alkyl, in particular C1-C4- alkyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a , as defined and preferably defined herein.
  • R 1 is Ci-C6-haloalkyl, in particular Ci-C 4 -haloalkyl, more particularly C1-C2- haloalkyl such as CF3 or CHF2.
  • R 1 can be haloalkyl
  • R 1 is CF3.
  • R 1 is Ci-C 4 -alkoxy-Ci-C6-alkyl, in particular Ci-C 4 -alkoxy-Ci-C 4 -alkyl, such as CH2-OCH3. Further specific embodiments thereof can be found in the below Table P1 .
  • R 1 is C3-Cs-cycloalkyl-Ci-C6-alkyl, in particular C3-C6- cycloalkyl-Ci-C 4 -alkyl.
  • a further embodiment relates to compounds, wherein R 1 is C3-C8- cycloalkyl-Ci-C6-alkyl, in particular C3-C6-cycloalkyl-Ci-C 4 -alkyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a in the alkyl moiety and/or substituted by one, two, three four or five or up to the maximum possible number of identical or different groups R 12b in the cycloalkyl moiety.
  • R 12a and R 12b are in each case as defined and preferably defined herein. Specific embodiments thereof can be found in the below Table P1 .
  • a further embodiment relates to compounds, wherein R 1 is C2-C6- alkenyl, in particular C2-C 4 -alkenyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a as defined and preferably defined herein. According to a specific embodiment thereof, R 1 is C2-C6-haloalkenyl, in particular C2-C4- haloalkenyl.
  • R 1 can be haloalkenyl
  • said haloalkenyl contains exactly one halogen selected from Br, CI and F.
  • R 1 is C3-C8-cycloalkyl-C2-C6-alkenyl or C3-C8-halocycloalkyl-C2-C6-alkenyl, in par- ticular C3-C6-cycloalkyl-C2-C4-alkenyl or C3-C6-halocycloalkyl-C2-C4-alkenyl. Further specific embodiments thereof can be found in the below Table P1.
  • R 1 is C2-C6-alkynyl, in particular C2-C4-alkynyl, such as C ⁇ CH, C ⁇ CCH 3 , CH 2 -C ⁇ C-H or CH 2 -C ⁇ C-CH 3 . According to one embodiment, this R 1 is not further substituted.
  • a further embodiment relates to compounds, wherein R 1 is C2-C6-alkynyl, in particular C2-C4-alkynyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a , as defined and preferably defined herein.
  • R 1 is C2-C6-haloalkynyl, in particular C2-C4-haloalkynyl.
  • R 1 is C3-C8-cycloalkyl-C2-C6-alkynyl or C3-C8- halocycloalkyl-C2-C6-alkynyl, in particular C3-C6-cycloalkyl-C2-C4-alkynyl or C3-C6-halocycloalkyl- C2-C4-alkynyl. Further specific embodiments thereof can be found in the below Table P1 .
  • R 1 is phenyl-Ci-C4-alkyl, in particular phenyl-Ci-C2-alkyl, such as benzyl, wherein the alkyl moiety in each case is unsubstituted or carries one, two or three R 12a as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3, and CN, and wherein the phenyl in each case is unsubstituted or carries one, two or three R 12b as as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, C1-C4- alkyl, in particular CH3 or C2H5, and CN. Specific embodiments thereof can be found in the below Table P1 .
  • R 1 is phenyl-C2-C4-alkenyl, in particular phenyl-C2-C3- alkenyl, such as phenylethenyl, wherein the alkenyl moiety in each case is unsubstituted or carries one, two or three R 12a as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3, and CN, and wherein the phenyl in each case is unsubstituted or carries one, two or three R 12b as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C2H5, and CN.
  • R 1 is phenyl-C2-C4-alkynyl, in particular phenyl-C2-C3-alkynyl
  • R 1 is Cs-Cs-cycloalkyl, in particular C3-C6-cycloalkyl, such as C3H5 (cyclopropyl), C4H7 (cyclobutyl), cyclopentyl or cyclohexyl.
  • a further embodiment relates to compounds, wherein R 1 is Cs-Cs-cycloalkyl, in particular C3-C6-cycloalkyl, such as C3H5 (cyclopropyl) or C4H7 (cyclobutyl), that is substituted by one, two, three four or five or up to the maximum possible number of identical or different groups R 12b as defined and preferably defined herein.
  • R 1 is Cs-Cs-halocycloalkyl, in particu- lar C3-C6-halocycloalkyl, such as halocyclopropyl, in particular 1 -F-cyclopropyl or 1 -CI- cyclopropyl.
  • R 1 is C3-Cs-cycloalkyl-C3-Cs- cycloalkyl, in particular C3-C6-cycloalkyl-C3-C6-cycloalkyl, wherein each of said cycloalkyl- cycloalkyl moieties is unsubstituted or carries one, two or three R 12b as defined and preferably defined herein, such as 1 -cyclopropyl-cyclopropyl or 2-cyclopropyl-cyclopropyl. Specific embodiments thereof can be found in the below Table P1.
  • R 1 is phenyl, wherein the phenyl is unsubstituted or carries one, two, three, four or five independently selected R 12b as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C2H5, and CN. Specific embodiments thereof can be found in the below Table P1 .
  • R 1 is selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl and C3-C6-cycloalkyl, wherein the R 1 are in each case unsubstituted or are substituted by R 12a and/or R 12b as defined and preferably defined herein.
  • the substituents may also have the preferred meanings for the respective substituent as defined above. Specific embodiments thereof can be found in the below Table P1 .
  • R 1 is selected from hydrogen, Ci-C6-alkyl, C1-C4- alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and C3-C6-cycloalkyl, wherein the R 1 are in each case unsubstituted or are substituted by R 12a1 and/or R 12b as defined and preferably defined herein.
  • the substituents may also have the preferred meanings for the respective substituent as defined above. Specific embodiments thereof can be found in the below Table P1 .
  • R 1 is selected from Ci-C6-alkyl, Ci-C4-alkoxy-Ci- C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl and C3-C6-cycloalkyl, wherein the R 1 are in each case unsubstituted or are substituted by R 12a1 and/or R 12b as defined and preferably defined herein.
  • the substituents may also have the preferred meanings for the respective substituent as defined above. Specific embodiments thereof can be found in the below Table P1 .
  • R 1 is selected from hydrogen, Ci-C6-alkyl, CF3, Ci- C4-alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6- alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6- alkyl, C3-C8-cycloalkyl-Ci-C6-haloalkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-Ci-C4-haloalkyl, phenyl-Ci-C4-alkoxy-Ci-C4-alkyl, phen
  • R 1 is selected from hydrogen, Ci-C6-alkyl, CF3, C1-C4- alkoxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C6-alkyl and C3-C8-cycloalkyl-Ci-C6-haloalkyl, in particular hydrogen, Ci-C6-alkyl, CF3, Ci-C4-alkoxy-Ci- C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkyny
  • R 1 is selected from Ci-C6-alkyl, CF3, Ci-C4-alkoxy- Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl, C3-C8- cycloalkyl-Ci-C6-haloalkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-Ci-C4-haloalkyl, phenyl-Ci-C4- alkoxy-Ci-C4-alkyl, pheny
  • R 1 is selected from Ci-C6-alkyl, CF3, Ci-C4-alkoxy-Ci-C6- alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C4-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl, Ci-C4-alkoxy-C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C6-alkyl and C3- Cs-cycloalkyl-Ci-C6-haloalkyl, in particular Ci-C6-alkyl, CF3, Ci-C4-alkoxy-Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-
  • R 1 Particularly preferred embodiments of R 1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1 -160 corresponds to one particular embodiment of the invention, wherein P1 -1 to P1 -160 are also in any combination a preferred embodiment of the present invention.
  • Table P1 line R 1 line R 1
  • P1-25 CH2CH2CH2CN, P1-64 CH CH(C 4 H 7 )
  • P1-29 CH 2 OCH 3 P1-68 CH CH(1-F-C 4 H 6 )
  • P1-38 CH CH 2 P1-77 C ⁇ C(C 4 H 7 )
  • R 2 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs- Cs-cycloalkyl, C3-C8-cycloalkyl-Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl, wherein the aliphatic groups of R 2 may carry one, two, three or up to the maximum possible number of identical or different groups R 12a which independently of one another are selected from halogen, OH, CN, nitro, Ci-C4-alkoxy, Cs-Cs-cycloalkyl, C3-C8- halocycloalkyl and Ci-C4-halogenalkoxy; and wherein the cycloalkyl and/or
  • R 2 is H.
  • R 2 is selected from Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-Cs-cycloalkyl-Ci-C4-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl and phenyl-C2-C4-alkynyl, wherein the R 2 are in each case unsubstituted or are substituted by R 12a and/or R 12b as defined and preferably defined herein. Specific embodiments thereof can be found in the below Table P2.
  • R 2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CHs, C 2 H 5 , CH(CHs) 2 , CH2CH2CH3, CH2CH2CH2CH3, CH 2 CH(CH 3 ) 2 .
  • a further embodiment relates to compounds, wherein R 2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a , as defined and preferably defined herein.
  • R 2 is C1-C6- haloalkyl, in particular Ci-C4-haloalkyl, more particularly Ci-C2-haloalkyl.
  • R 2 is Ci-C4-alkoxy-Ci-C6-alkyl, in particular Ci-C4-alkoxy-Ci-C4- alkyl, such as CH2OCH3 or CH2CH2OCH3.
  • R 2 is hydroxy-Ci-C6-alkyl, in particular hydroxyl-Ci-C4-alkyl, such as CH2CH2OH. Further specific embodiments thereof can be found in the below Table P2
  • R 2 is C3-Cs-cycloalkyl-Ci-C6-alkyl, in particular C3-C6- cycloalkyl-Ci-C4-alkyl.
  • a further embodiment relates to compounds, wherein R 2 is C3-C8- cycloalkyl-Ci-C6-alkyl, in particular C3-C6-cycloalkyl-Ci-C4-alkyl, more particularly C3-C6- cycloalkyl-Ci-C2-alkyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a in the alkyl moiety and/or substituted by one, two, three four or five or up to the maximum possible number of identical or different groups R 12b in the cycloalkyl moiety.
  • R 12a and R 12b are in each case as defined and preferably defined herein. Specific embodiments thereof can be found in the below Table P2.
  • R 2 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as
  • R 2 is C3-C8-cycloalkyl-C2-C6-alkenyl or C3-C8-halocycloalkyl-C2-C6- alkenyl, in particular C3-C6-cycloalkyl-C2-C4-alkenyl or C3-C6-halocycloalkyl-C2-C4-alkenyl. Further specific embodiments thereof can be found in the below Table P2.
  • R 2 is C2-C6-alkynyl, in particular C2-C4-alkynyl, such as CH2C ⁇ CH or CH2C ⁇ CCH3.
  • a further embodiment relates to compounds, wherein R 2 is C2-C6- alkynyl, in particular C2-C4-alkynyl, that is substituted by one, two or three or up to the maximum possible number of identical or different groups R 12a , as defined and preferably defined herein.
  • R 2 is C2-C6-haloalkynyl, in particular C2-C4- haloalkynyl.
  • R 2 is C3-C8-cycloalkyl-C2-C6- alkynyl or C3-C8-halocycloalkyl-C2-C6-alkynyl, in particular C3-C6-cycloalkyl-C2-C4-alkynyl or C3- C6-halocycloalkyl-C2-C4-alkynyl. Specific embodiments thereof can be found in the below Table P2.
  • R 2 is phenyl-Ci-C4-alkyl, in particular phenyl-Ci-C2-alkyl, such as benzyl, wherein the alkyl moiety in each case is unsubstituted or carries one, two or three R 12a as defined and preferably defined herein, in particular selected from halogen, in par- ticular F and CI, Ci-C4-alkoxy, in particular OCH3, and CN, and wherein the phenyl in each case is unsubstituted or carries one, two or three R 12b as as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, C1-C4- alkyl, in particular CH3 or C2H5, and CN. Specific embodiments thereof can be found in the below Table P2.
  • R 2 is phenyl-C2-C4-alkenyl, in particular phenyl-C2-C3- alkenyl, such as phenylethenyl, wherein the alkenyl moiety in each case is unsubstituted or carries one, two or three R 12a as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3, and CN, and wherein the phenyl in each case is unsubstituted or carries one, two or three R 12b as defined and preferably de- fined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C2H5, and CN.
  • R 12a as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3, Ci-
  • R 2 is phenyl-C2-C4-alkynyl, in particular phenyl-C2-C3- alkynyl, such as phenylethinyl, wherein the alkynyl moiety in each case is unsubstituted or carries one, two or three R 12a , as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3, and CN, and wherein the phenyl in each case is unsubstituted or carries one, two or three R 12b as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCH3, Ci-C4-alkyl, in particular CH3 or C2H5, and CN.
  • R 12a as defined and preferably defined herein, in particular selected from halogen, in particular F and CI, Ci-C4-alkoxy, in particular OCH3,
  • R 2 is Cs-Cs-cycloalkyl, in particular C3-C6-cycloalkyl, such as C3H5 (cyclopropyl), C4H7 (cyclobutyl), cyclopentyl or cyclohexyl.
  • a further embodiment relates to compounds, wherein R 2 is Cs-Cs-cycloalkyl, in particular C3-C6-cycloalkyl, such as C3H5 (cyclopropyl) or C4H7 (cyclobutyl), that is substituted by one, two, three four or five or up to the maximum possible number of identical or different groups R 12b as defined and preferably defined herein.
  • R 2 is Cs-Cs-halocycloalkyl, in particular C3-C6-halocycloalkyl, such as halocyclopropyl, in particular 1-F-cyclopropyl or 1-CI- cyclopropyl.
  • R 2 is C3-Cs-cycloalkyl-C3-Cs- cycloalkyl, in particular C3-C6-cycloalkyl-C3-C6-cycloalkyl, wherein each of said cycloalkyl- cycloalkyl moieties is unsubstituted or carries one, two or three R 12b as defined and preferably defined herein.
  • R 2 is phenyl, wherein the phenyl is unsubstituted or carries one, two, three, four or five independently selected R 12b as defined and preferably defined herein, in particular selected from halogen, in particular CI and F, Ci-C4-alkoxy, in particular OCHs, Ci-C 4 -alkyl, in particular CH 3 or C 2 H 5 , and CN.
  • R 2 is selected from hydrogen, Ci-C6-alkyl, C2-C6- alkenyl and C2-C6-alkynyl, wherein the R 2 are in each case unsubstituted or are substituted by R 12a and/or R 12b as defined and preferably defined herein.
  • the substituents may also have the preferred meanings for the respective substituent as defined above. Specific embodiments thereof can be found in the below Table P2.
  • R 2 Particularly preferred embodiments of R 2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-88 corresponds to one particular embodiment of the inven tion, wherein P2-1 to P2-88 are also in any combination a preferred embodiment of the present invention.
  • each line of lines A-1 to A-70 corresponds to one particular embodiment of the invention, wherein A-1 to A-70 are also in any combination a preferred em- bodiment for combinations of R 1 and R 2 of the present invention.
  • R 12a or, more specifically, R 12a1 are the possible substituents for any aliphatic moiety of R 1 and/or R 2 and can independently be defined for R 1 and R 2 .
  • the respective R 1 is not further substituted with R 12a .
  • the respective R 1 contains one, two, three or up to the maximum pos- sible number of identical or different groups R 12a or R 12a1 .
  • the respective R 1 contains one, two or three identical or different groups R 12a or R 12a1 .
  • the respective R 1 contains one group R 12a or R 12a1 .
  • the respective R 1 contains one or two identical or different groups R 12a or R 12a1 .
  • the respective R 2 is not further substituted with R 12a .
  • the respective R 2 contains one, two, three or up to the maximum possible number of identical or different groups R 12a .
  • the respective R 2 contains one, two or three identical or different groups R 12a .
  • the respective R 2 contains one group R 12a .
  • the respective R 2 contains one or two identical or different groups R 12a .
  • R 12a according to the invention is independently selected from halogen, OH, CN, nitro, Ci-C 4 - alkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and Ci-C4-halogenalkoxy.
  • R 12a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and Ci-C2-halogenalkoxy.
  • R 12a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl and Ci-C2-halogenalkoxy.
  • R 12a is independently selected from halogen, OH, CN, C3-C6- cycloalkyl and C3-C6-halocycloalkyl. Specifically, R 12a is independently selected from F, CI, OH, CN, cyclopropyl, 1 -F-cyclopropyl and 1 -CI-cyclopropyl.
  • R 12a1 are independently of one another selected from halogen, OH, CN, nitro, Cs-Cs-cycloalkyl, C3-Cs-halocycloalkyl and Ci-C4-halogenalkoxy, in particular halogen, OH, CN, C3-C6-cycloalkyl and Cs-Cs-halocycloalkyl.
  • R 12a1 is independently selected from F, CI, OH, CN, cyclopropyl, 1 -F-cyclopropyl and 1 -CI-cyclopropyl.
  • R 12b are the possible substituents for any cycloalkyi and/or phenyl moiety of R 1 and/or R 2 and can independently be defined for R 1 and R 2 .
  • the respective R 1 is not further substituted with R 12b .
  • the respective R 1 contains one, two, three or up to the maximum possible number of identical or different groups R 12b .
  • the respective R 1 contains one, two or three identical or different groups R 12b .
  • the respective R 1 contains one group R 12b .
  • the respective R 1 contains one or two identical or different groups R 12b .
  • the respective R 2 is not further substituted with R 12b .
  • the respective R 2 contains one, two, three or up to the maximum possible number of identical or different groups R 12b .
  • the respective R 2 contains one, two or three identical or different groups R 12b .
  • the respective R 2 contains one group R 12b .
  • the respective R 2 contains one or two identical or different groups R 12b .
  • R 12b according to the invention is is independently selected from halogen, OH, CN, nitro, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C1-C4- halogenalkoxy.
  • R 12b is independently selected from halogen, CN, nitro, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and C1-C2- halogenalkoxy.
  • R 12b is independently selected from F, CI, OH, CN, nitro, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl and halogenmethoxy.
  • R 31 according to the invention is halogen, in particular F, CI, Br or I, more preferably F (compounds of formula I.A below), CI (compounds of formula I.A below) or Br (compounds of formula I.A below).
  • n 1 .
  • n is 2 or 3. According to one specific embodiment thereof, n is 2, according to a further specific embodiment, n is 3.
  • one R 3 is attached to the 3-position (R 32 ).
  • n 1 , according to a further specific
  • n is 2.
  • one R 3 is attached to the 5-position (R 33 ).
  • n is 1 , according to a further specific
  • n is 2.
  • n is 1 , 2 or 3 and one R 3 is in 3- or 5-position.
  • one R 3 is attached to the 6-position (R 34 ).
  • n is 1 , according to a further specific
  • n is 2.
  • two R 3 are attached in 3, 5-position.
  • n is 2, according to a further specific
  • n 3.
  • two R 3 are attached in 3, 6-position.
  • n is 2, according to a further specific
  • n 3.
  • two R 3 are attached in 5, 6-position.
  • n is 2, according to a further specific
  • n 3.
  • n is 1 , 2 or 3 and (R 3 ) n is 3-(R 3 )i , 5-(R 3 )i , 3,5- (R 3 ) 2 , 3,6-(R 3 ) 2 , 5,6-(R 3 ) 2 or 3,5,6-(R 3 ) 3 , in particular, n is 1 or 2 and (R 3 ) n is 3-(R 3 )i , 5-(R 3 )i , 3,5- (R 3 ) 2 , 3,6-(R 3 ) 2 or 5,6-(R 3 ) 2 . More specifically, n is 1 or 2 and (R 3 ) n is 3-(R 3 )i , 5-(R 3 )i or 3,5-(R 3 ) 2 .
  • n is 1 or 2 and one R 3 is attached to the 5-position (R 33 ), wherein said R 33 is selected from halogen, CN, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3- Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C3-Cs-cycloalkyl-Ci-C 4 -alkyl, wherein each of R 33 does not contain any further substituents or is further substituted by one, two, three or four R 33a ; wherein R 33a is independently selected from halogen, CN, OH, Ci-C 4 -alkyl, Cs-Cs-cycloalkyl, Cs-Cs- halocycloalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
  • One embodiment of the invention relates to the compounds I, having the formula 1-1
  • R 32 and R 33 are hydrogen or independently selected from the substituents as defined and preferably defined herein for R 3 and/or R 32 and R 33 , wherein the possible substituents of R 32 and R 33 , respectively, R 32a and R 33a , are selected from the substituents as defined and prefera- bly defined for R 3a
  • R 34 is selected from hydrogen, halogen, CN, NO2, OH, SH, d-Ce-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl that is substituted by one, two, three or four halogen, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C 2 - C6-haloalkynyl, Cs-Cs-cycloalkyl, Cs--cycl
  • R 34 does not contain any further substituents or is further substituted by one, two, three or four R 34a ; wherein R 34a is independently selected from CN, N0 2 , OH, Ci-C4-alkyl, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; wherein at least one of R 32 , R 33 and R 34 is not hydrogen.
  • R 34 and R 34a the embodiments and preferences as detained for R 3 also apply accordingly.
  • R 34 is selected from hydrogen, halogen, CN, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C 2 - C6-alkynyl, C 2 -C6-haloalkynyl, C3-C6-cycloalkyl, Cs-Cs-halocycloalkyl, Cs-Ce-cycloalkyl-Ci-d- alkyl,; wherein each of R 34 does not contain any further substituents or is further substituted by one, two, three or four R 34a , independently selected from CN, OH, Ci-C4-alkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
  • R 34 is hydrogen
  • R 3 (or R 32 , R 33 , R 34 , respectively) that is present in the inventive compounds
  • the following embodiments and preferences apply independently of the meaning of any other R 3 (or R 32 , R 33 , R 34 , respectively) that may be present in the phenyl ring.
  • R 3 is independently selected from halogen, CN, N0 2 , OH, SH, d-Ce-alkyl, Ci-C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Cs-Cs-cycloalkyl, Cs-Cs- cycloalkyloxy, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 ,
  • R 3 is independently selected from F, CI, Br, CN, C1-C4- alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, S(Ci-C 4 -alkyl), S(0)(Ci-C 4 -alkyl) and S(0) 2 (Ci-C 4 -alkyl).
  • R 3 is halogen, in particular Br, F or CI, more specifically F or CI.
  • R 3 is CN
  • R 3 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 .
  • R 3 is Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2 or CH 2 CI.
  • R 3 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH 3 or OCH2CH 3 .
  • R 3 is Ci-C6-haloalkoxy, in particular C1-C4- haloalkoxy, more specifically Ci-C 2 -haloalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCb.
  • R 3 is C2-C6-alkynyl or C2-C6-haloalkynyl, in particular C2-C4-alkynyl or C2-C4-haloalkynyl, such as C CH.
  • R 3 is selected from S(Ci-C2-alkyl), S(0)(Ci-C2-alkyl) and S(0) 2 (Ci-C 2 -alkyl), in particular SCH 3 , S(0)(CH 3 ) and S(0) 2 (CH 3 ).
  • R 3a is independently selected from halogen, CN, NO2, OH, Ci-C4-alkyl, Ci-C4-haloalkyl, C 3 -C 3 - cycloalkyl, C 3 -C8-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, CN, Ci-C2-alkyl, Ci-C2-haloalkyl, C 3 -C6-cycloalkyl, C 3 -C6-halocycloalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy.
  • R 3a is independently selected from F, CI, CN, OH, CH 3 , halomethyl, cyclopropyl, halocyclopropyl, OCH 3 and halogenmethoxy.
  • R 4 there can be zero, one, two, three, four or five R 4 present, namely for m is 0, 1 , 2, 3, 4 or 5.
  • m is 0, 1 , 2, 3 or 4.
  • m is 0.
  • m is 1 , 2, 3 or 4, in particular 1 , 2 or 3, more specifically 1 or 2. According to one specific embodiment thereof, m is 1 , according to a further specific embodiment, m is 2.
  • m is 2, 3 or 4.
  • m is 3.
  • one R 4 is attached to the para-position (4- position).
  • one R 4 is attached to the meta-position (3- position).
  • one R 4 is attached to the ortho-position (2- position).
  • two R 4 are attached in 2,4-position.
  • two R 4 are attached in 2,3-position.
  • two R 4 are attached in 2,5-position.
  • two R 4 are attached in 2,6-position.
  • two R 4 are attached in 3,4-position.
  • two R 4 are attached in 3,5-position.
  • R 4 are attached in 2,4,6-position.
  • the following embodiments and preferences apply independently of the meaning of any other R 4 that may be present in the phenyl ring.
  • each of R 4 is unsubstituted or further substituted by one, two, three or four independently selected R 4a , wherein R 4a is as defined and preferably defined herein.
  • R 4 is independently selected from F, CI, Br, CN, Ci-C4-alkyl, Ci-C 4 -haloalkyl, Ci-C 4 -alkoxy, Ci-C 4 -haloalkoxy, S(Ci-C 4 -alkyl), S(0)(Ci-C 4 -alkyl) and S(0) 2 (Ci- C 4 -alkyl).
  • R 4 is independently selected from halogen, in particular from Br, F and CI, more specifically from F and CI.
  • R 4 is CN
  • R 4 is NO2.
  • R 4 is OH.
  • R 4 is SH.
  • R 4 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. Further appropriate alkyls are ethyl, n-propyl, i-propyl, n-butyl, i-butyl and t-butyl.
  • R 4 is Ci-C6-haloalkyl, in particular Ci-C4-haloalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2 or CH 2 CI.
  • R 4 is Ci-C6-alkyl, preferably Ci-C4-alkyl, substituted by OH, more preferably CH 2 OH, CH 2 CH 2 OH, CH 2 CH 2 CH 2 OH, CH(CH 3 )CH 2 OH,
  • R 4 is CH 2 CH(CH 3 )OH, CH2CH2CH2CH2OH.
  • R 4 is CH 2 OH.
  • R 4 is Ci-C6-alkyl, preferably Ci-C4-alkyl substituted by CN, more preferably CH 2 CN, CH 2 CH 2 CN, CH 2 CH 2 CH 2 CN, CH(CH 3 )CH 2 CN, CH 2 CH(CH 3 )CN, CH 2 CH- 2CH2CH2CN.
  • R 4 is CH2CH2CN.
  • R 4 is CH(CH 3 )CN.
  • R 4 is Ci-C4-alkoxy-Ci-C6-alkyl, more preferably Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 4 is CH20CH 3 .
  • R 4 is CH 2 CH 2 OCH 3 .
  • R 4 is CH(CH 3 )OCH 3 .
  • R 4 is CH(CH 3 )OCH2CH 3 .
  • R 4 is CH2CH20CH2CH 3 .
  • R 4 is Ci-C4-haloalkoxy-Ci-C6- alkyl, more preferably Ci-C4-alkoxy-Ci-C4-alkyl.
  • R 4 is CH20CF 3 .
  • R 4 is CH2CH2OCF3.
  • R 4 is CH2OCCI3.
  • R 4 is CH2CH2OCCI3.
  • R 4 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
  • R 4 is Ci-C6-haloalkoxy, in particular C1-C4- haloalkoxy, more specifically Ci-C 2 -haloalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCb.
  • R 4 is C 3 -C 8 -cycloalkyl-C2-C 6 - alkenyl, preferably C3-C6-cycloalkyl-C2-C 4 -alkenyl.
  • R 4 is C3-C6-halocycloalkyl-C2-C 4 -alkenyl, preferably C3-C8-halocycloalkyl-C2-C6-alkenyl.
  • R 4 is C2-C6-alkynyl or C2-C6-haloalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -haloalkynyl, such as C ⁇ CH, CH 2 CCH or CH2CCCH3.
  • R 4 is C2-C6-alkynyl, preferably C2-C 4 -alkynyl, substituted by OH, more preferably, CCOH, CH 2 CCOH. In a special embodiment R 4 is CCOH. In a further special embodiment R 4 is CH2CCOH. According to a further specific embodiment R 4 is Ci-C 4 -alkoxy-C2-C6-alkynyl, more preferably Ci-C 4 -alkoxy-C2-C 4 -alkynyl. In a special embodiment R 4 is CCOCH3. In a further special embodiment R 4 is CH2CCOCH3.
  • R 4 is Ci-C 4 -haloalkoxy-C2-C6-alkynyl, more preferably Ci-C 4 -haloalkoxy- C2-C 4 -alkynyl.
  • R 4 is CCOCF3.
  • R 4 is CH2CCOCF3.
  • R 4 is CCOCCI3.
  • R 4 is CH2CCOCCI3.
  • R 4 is C3-C8-cycloalkyl-C2-C6- alkynyl, preferably C3-C6-cycloalkyl-C2-C 4 -alkynyl.
  • R 4 is C3-C6-halocycloalkyl-C2-C 4 -alkynyl, preferably C3-C8-halocycloalkyl-C2-C6-alkynyl.
  • R 4 is Cs-Cs-cycloalkyl, preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, in particular cyclopropyl or cyclobutyl.
  • R 4 is cyclopropyl.
  • R 4 is cyclobutyl.
  • R 4 is cyclopentyl.
  • R 4 is cyclohexyl.
  • R 4 is Cs-Cs-cycloalkoxy, preferably C3-C6-cycloalkoxy.
  • R 4 is O-cyclopropyl.
  • R 4 is Cs-Cs-halocycloalkyl, more preferably fully or partially halogenated C3-C6-cycloalkyl.
  • R 4 is fully or partially halogenated cyclo- propyl.
  • R 4 is 1 -CI-cyclopropyl.
  • R 4 is 2-CI-cyclopropyl.
  • R 4 is 1 -F-cyclopropyl.
  • R 4 is 2-F-cyclopropyl. In a further special embodiment R 4 is fully or partially halogenated cyclobutyl. In a further special embodiment R 4 is 1 -CI-cyclobutyl. In a further special embodiment R 4 is 1 -F-cyclobutyl. In a further special embodiment R 4 is 3,3-Cl2-cyclobutyl. In a further special embodiment R 4 is 3,3-F2-cyclobutyl. According to a specific embodiment R 4 is C3- Cs-cycloalkyl substituted by Ci-C4-alkyl, more preferably is C3-C6-cycloalkyl substituted by Ci- C4-alkyl.
  • R 4 is 1 -CH3-cyclopropyl.
  • R 4 is C3-C8-cycloalkyl substituted by CN, more preferably is C3-C6-cycloalkyl substituted by CN.
  • R 4 is 1 -CN-cyclopropyl.
  • R 4 is C3-C8-cycloalkyl-C3-C8-cycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-cycloalkyl.
  • R 4 is cyclopropyl-cyclopropyl.
  • R 4 is 2-cyclopropyl- cyclopropyl.
  • R 4 is Cs-Cs-cycloalkyl-Cs-Cs- halocycloalkyl, preferably C3-C6-cycloalkyl-C3-C6-halocycloalkyl.
  • R 4 is C3-C8-cycloalkyl-Ci-C4-alkyl, preferably C3-C6- cycloalkyl-Ci-C4-alkyl.
  • R 4 is CH(CH3)(cyclopropyl).
  • R 4 is CH2-(cyclopropyl).
  • R 4 is C3-C8-cycloalkyl-Ci-C4-alkyl wherein the alkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R a as defined and preferably herein and the cycloalkyl moiety can be substituted by one, two, three or up to the maximum possible number of identical or different groups R b as defined and preferably herein.
  • R 4 is C3-C8-cycloalkyl-Ci-C4-haloalkyl, C3-C6-cycloalkyl-Ci- C4-haloalkyl. According to a specific embodiment R 4 is C3-C8-halocycloalkyl-Ci-C4-alkyl, C3-C6- halocycloalkyl-Ci-C4-alkyl. In a special embodiment R 4 is fully or partially halogenated cyclopro- pyl-Ci-C4-alkyl. In a further special embodiment R 4 is 1 -CI-cyclopropyl-Ci-C4-alkyl. In a further special embodiment R 4 is 1 -F-cyclopropyl-Ci-C4-alkyl.
  • R 4 is N H2.
  • R 4 is NH(Ci-C4-alkyl). According to a specific embodiment R 4 is NH(CH3). According to a specific embodiment R 4 is NH(CH2CH3). According to a specific embodiment R 4 is NH(CH2CH2CH3). According to a specific embodiment R 4 is
  • R 4 is NI-KCI-bCI-bCI-bCHs). According to a specific embodiment R 4 is NH(C(CH 3 ) 3 ).
  • R 4 is N(Ci-C4-alkyl)2. According to a specific embodiment R 4 is N(CH3)2. According to a specific embodiment R 4 is N(CH2CH3)2. According to a specific embodiment R 4 is N(CH2CH 2 CI-l3)2. According to a specific embodiment R 4 is N(CH(CH 3 )2)2.
  • R 4 is N(CH2CH2CH2CH3)2. According to a specific embodi- ment R 4 is NH(C(CH 3 ) 3 )2. According to one another embodiment R 4 is NH(C3-C8-cycloalkyl) preferably NH(C3-C6- cycloalkyl). According to a specific embodiment R 4 is NH(cyclopropyl). According to a specific embodiment R 4 is NH(cyclobutyl). According to a specific embodiment R 4 is NH(cyclopentyl). According to a specific embodiment R 4 is NH(cyclohexyl).
  • R 4 is N(C3-C8-cycloalkyl)2 preferably N(C3-C6- cycloalkyl)2. According to a specific embodiment R 4 is N(cyclopropyl)2. According to a specific embodiment R 4 is N(cyclobutyl)2. According to a specific embodiment R 4 is N(cyclopentyl)2.
  • R 4 is N(cyclohexyl)2.
  • R 4 is selected from S(Ci-C2-alkyl), S(0)(Ci-C2-alkyl) and S(0) 2 (Ci-C 2 -alkyl), in particular SCH 3 , S(0)(CH 3 ) and S(0) 2 (CH 3 ).
  • R 4 is SO2CF3.
  • R 4 Particularly preferred embodiments of R 4 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-16 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-16 are also in any combination with one another a preferred embodiment of the present invention.
  • these specific embodiments and preferences apply independently of the meaning of any other R 4 that may be present in the phenyl ring:
  • P4-62 4-CHs P4-100 2,3-(OCH 3 ) 2 P4-138 3,4,5-(OCH 2 CH 3 )3
  • P4-65 4-CH 2 CH 3 P4-103 2,6-(OCH 3 ) 2 P4-141 2,4,5-(OCF 3 ) 3
  • P4-68 4-CFs P4-106 3,4-(OCH 2 CH 3 ) 2 P4-144 2,3,4-(OCHF 2 ) 3
  • R 31 is F, corresponding to compounds I.A:
  • R 31 is CI, corresponding to compounds I.B:
  • R 31 is Br, corresponding to compounds I.C:
  • Table 1 a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.A.A1 .B1 to I.A.A1 .B1536).
  • Table 2a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-2 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A2.B1 to I.A.A2.B1536).
  • Table 3a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-3 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A3.B1 to I.A.A3.B1536).
  • Table 4a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-4 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A4.B1 to I.A.A4.B1536).
  • Table 5a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-5 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.A.A5.B1 to I.A.A5.B1536).
  • Table 6a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-6 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.A.A6.B1 to I.A.A6.B1536).
  • Table 7a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-7 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A7.B1 to I.A.A7.B1536).
  • Table 8a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-8 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A8.B1 to I.A.A8.B1536).
  • Table 9a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-9 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A9.B1 to I.A.A9.B1536).
  • Table 10a Compounds of the formula I.A in which the combination of R 1 and R 2 corre- sponds to line A-10 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A10.B1 to I.A.A10.B1536).
  • Table 1 1 a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-1 1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A1 1 .B1 to I.A.A1 1 .B1536).
  • Table 12a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-12 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A12.B1 to I.A.A12.B1536).
  • Table 13a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-13 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A13.B1 to I.A.A13.B1536).
  • Table 14a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-14 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A14.B1 to I.A.A14.B1536).
  • Table 15a Compounds of the formula I.A in which the combination of R 1 and R 2 corre- sponds to line A-15 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A15.B1 to I.A.A15.B1536).
  • Table 16a ompounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-16 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A16.B1 to I.A.A16.B1536).
  • Table 17a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-17 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A17.B1 to I.A.A17.B1536).
  • Table 18a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-18 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A18.B1 to I.A.A18.B1536).
  • Table 19a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-19 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A19.B1 to I.A.A19.B1536).
  • Table 20a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-20 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A20.B1 to I.A.A20.B1536).
  • Table 21 a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-21 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A21 .B1 to I.A.A21 .B1536).
  • Table 22a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-22 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A22.B1 to I.A.A22.B1536).
  • Table 23a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-23 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A23.B1 to I.A.A23.B1536).
  • Table 24a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-24 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A24.B1 to I.A.A24.B1536).
  • Table 25a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-25 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A25.B1 to I.A.A25.B1536).
  • Table 26a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-26 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A26.B1 to I.A.A26.B1536).
  • Table 27a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-27 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A27.B1 to I.A.A27.B1536).
  • Table 28a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-28 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A28.B1 to I.A.A28.B1536).
  • Table 29a Compounds of the formula I .A in which the combination of R 1 and R 2 corresponds to line A-29 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A29.B1 to I.A.A29.B1536).
  • Table 30a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-30 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA30.B1 to I.A.A30.B1536).
  • Table 31 a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-31 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA31 .B1 to I.AA31 .B1536).
  • Table 32a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-32 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA32.B1 to I.AA32.B1536).
  • Table 33a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-33 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A33.B1 to I.AA33.B1536).
  • Table 34a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-34 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA34.B1 to I.AA34.B1536).
  • Table 35a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-35 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA35.B1 to I.AA35.B1536).
  • Table 36a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-36 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA36.B1 to I.AA36.B1536).
  • Table 37a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-37 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.AA37.B1 to I.AA37.B1536).
  • Table 38a Compounds of the formula I.A in which the combination of R 1 and R 2 corresponds to line A-38 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A38.B1 to I.A.A38.B1536).
  • Table 39a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-39 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A39.B1 to I.A.A39.B1536).
  • Table 40a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-40 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A40.B1 to I.A.A40.B1536).
  • Table 41 a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-41 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A41 .B1 to I.A.A41 .B1536).
  • Table 42a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-42 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A42.B1 to I.A.A42.B1536).
  • Table 43a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-43 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A43.B1 to I.A.A43.B1536).
  • Table 44a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-44 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A44.B1 to I.A.A44.B1536).
  • Table 45a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-45 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A45.B1 to I.A.A45.B1536).
  • Table 46a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-46 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A46.B1 to I.A.A46.B1536).
  • Table 47a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-47 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A47.B1 to I.A.A47.B1536).
  • Table 48a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-48 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A48.B1 to I.A.A48.B1536).
  • Table 49a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-49 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A49.B1 to I.A.A49.B1536).
  • Table 50a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-50 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A50.B1 to I.A.A50.B1536).
  • Table 51 a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-51 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A51 .B1 to I.A.A51 .B1536).
  • Table 52a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-52 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A52.B1 to I.A.A52.B1536).
  • Table 53a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-53 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A53.B1 to I.A.A53.B1536).
  • Table 54a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-54 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A54.B1 to I.A.A54.B1536).
  • Table 55a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-55 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A55.B1 to I.A.A55.B1536).
  • Table 56a Compounds of the formula I .A in which the combination of R 1 and R 2 corresponds to line A-56 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A56.B1 to I.A.A56.B1536).
  • Table 57a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-57 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A57.B1 to I.A.A57.B1536).
  • Table 58a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-58 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A58.B1 to I.A.A58.B1536).
  • Table 59a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-59 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A59.B1 to I.A.A59.B1536).
  • Table 60a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-60 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A60.B1 to I.A.A60.B1536).
  • Table 61 a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-61 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A61 .B1 to I.A.A61 .B1536).
  • Table 62a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-62 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A62.B1 to I.A.A62.B1536).
  • Table 63a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-63 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A63.B1 to I.A.A63.B1536).
  • Table 64a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-64 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A64.B1 to I.A.A64.B1536).
  • Table 65a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-65 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A65.B1 to I.A.A65.B1536).
  • Table 66a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-66 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A66.B1 to I.A.A66.B1536).
  • Table 67a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-67 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A67.B1 to I.A.A67.B1536).
  • Table 68a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-68 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A68.B1 to I.A.A68.B1536).
  • Table 69a Compounds of the formula I. A in which the combination of R 1 and R 2 corresponds to line A-69 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A69.B1 to I.A.A69.B1536).
  • Table 70a Compounds of the formula I. A in which the combination of R 1 and R 2 corre- sponds to line A-70 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.A.A70.B1 to I.A.A70.B1536).
  • Table 1 b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.B.A1 .B1 to I.B.A1 .B1536).
  • Table 2b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-2 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.B.A2.B1 to I.B.A2.B1536).
  • Table 3b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-3 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A3.B1 to I.B.A3.B1536).
  • Table 4b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-4 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A4.B1 to I.B.A4.B1536).
  • Table 5b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-5 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A5.B1 to I.B.A5.B1536).
  • Table 6b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-6 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A6.B1 to I.B.A6.B1536).
  • Table 7b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-7 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.B.A7.B1 to I.B.A7.B1536).
  • Table 8b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-8 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A8.B1 to I.B.A8.B1536).
  • Table 9b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-9 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A9.B1 to I.B.A9.B1536).
  • Table 10b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-10 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A10.B1 to I.B.A10.B1536).
  • Table 1 1 b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-1 1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A1 1 .B1 to I.B.A1 1 .B1536).
  • Table 12b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-12 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A12.B1 to I.B.A12.B1536).
  • Table 13b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-13 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A13.B1 to I.B.A13.B1536).
  • Table 14b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-14 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A14.B1 to I.B.A14.B1536).
  • Table 15b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-15 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A15.B1 to I.B.A15.B1536).
  • Table 16b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-16 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A16.B1 to I.B.A16.B1536).
  • Table 17b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-17 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A17.B1 to I.B.A17.B1536).
  • Table 18b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-18 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A18.B1 to I.B.A18.B1536).
  • Table 19b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-19 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A19.B1 to I.B.A19.B1536).
  • Table 20b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-20 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A20.B1 to I.B.A20.B1536).
  • Table 21 b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-21 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A21 .B1 to I.B.A21 .B1536).
  • Table 22b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-22 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A22.B1 to I.B.A22.B1536).
  • Table 24b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-24 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A24.B1 to I.B.A24.B1536).
  • Table 25b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-25 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A25.B1 to I.B.A25.B1536).
  • Table 26b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-26 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A26.B1 to I.B.A26.B1536).
  • Table 27b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-27 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A27.B1 to I.B.A27.B1536).
  • Table 28b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-28 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A28.B1 to I.B.A28.B1536).
  • Table 29b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-29 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A29.B1 to I.B.A29.B1536).
  • Table 30b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-30 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A30.B1 to I.B.A30.B1536).
  • Table 31 b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-31 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A31 .B1 to I.B.A31 .B1536).
  • Table 32b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-32 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A32.B1 to I.B.A32.B1536).
  • Table 33b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-33 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A33.B1 to I.B.A33.B1536).
  • Table 34b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-34 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A34.B1 to I.B.A34.B1536).
  • Table 35b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-35 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A35.B1 to I.B.A35.B1536).
  • Table 36b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-36 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A36.B1 to I.B.A36.B1536).
  • Table 37b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-37 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A37.B1 to I.B.A37.B1536).
  • Table 38b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-38 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A38.B1 to I.B.A38.B1536).
  • Table 39b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-39 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A39.B1 to I.B.A39.B1536).
  • Table 40b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-40 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A40.B1 to I.B.A40.B1536).
  • Table 41 b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-41 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A41 .B1 to I.B.A41 .B1536).
  • Table 42b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-42 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A42.B1 to I.B.A42.B1536).
  • Table 43b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-43 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A43.B1 to I.B.A43.B1536).
  • Table 44b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-44 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A44.B1 to I.B.A44.B1536).
  • Table 45b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-45 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A45.B1 to I.B.A45.B1536).
  • Table 46b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-46 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A46.B1 to I.B.A46.B1536).
  • Table 47b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-47 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A47.B1 to I.B.A47.B1536).
  • Table 48b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-48 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A48.B1 to I.B.A48.B1536).
  • Table 49b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-49 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A49.B1 to I.B.A49.B1536).
  • Table 50b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-50 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A50.B1 to I.B.A50.B1536).
  • Table 51 b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-51 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A51 .B1 to I.B.A51 .B1536).
  • Table 52b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-52 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A52.B1 to I.B.A52.B1536).
  • Table 53b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-53 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A53.B1 to I.B.A53.B1536).
  • Table 54b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-54 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A54.B1 to I.B.A54.B1536).
  • Table 55b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-55 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A55.B1 to I.B.A55.B1536).
  • Table 56b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-56 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A56.B1 to I.B.A56.B1536).
  • Table 57b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-57 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A57.B1 to I.B.A57.B1536).
  • Table 58b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-58 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A58.B1 to I.B.A58.B1536).
  • Table 59b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-59 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A59.B1 to I.B.A59.B1536).
  • Table 60b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-60 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A60.B1 to I.B.A60.B1536).
  • Table 61 b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-61 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A61 .B1 to I.B.A61 .B1536).
  • Table 62b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-62 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A62.B1 to I.B.A62.B1536).
  • Table 63b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-63 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A63.B1 to I.B.A63.B1536).
  • Table 64b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-64 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A64.B1 to I.B.A64.B1536).
  • Table 65b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-65 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A65.B1 to I.B.A65.B1536).
  • Table 66b Compounds of the formula I.B in which the combination of R 1 and R 2 corre- sponds to line A-66 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A66.B1 to I.B.A66.B1536).
  • Table 67b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-67 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A67.B1 to I.B.A67.B1536).
  • Table 68b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-68 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A68.B1 to I.B.A68.B1536).
  • Table 69b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-69 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A69.B1 to I.B.A69.B1536).
  • Table 70b Compounds of the formula I.B in which the combination of R 1 and R 2 corresponds to line A-70 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.B.A70.B1 to I.B.A70.B1536).
  • Table 1 c Compounds of the formula I .C in which the combination of R 1 and R 2 corresponds to line A-1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A1.B1 to I.C.A1 .B1536).
  • Table 2c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-2 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A2.B1 to I.C.A2.B1536).
  • Table 3c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-3 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.C.A3.B1 to I.C.A3.B1536).
  • Table 4c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-4 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A4.B1 to I.C.A4.B1536).
  • Table 5c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-5 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A5.B1 to I.C.A5.B1536).
  • Table 6c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-6 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A6.B1 to I.C.A6.B1536).
  • Table 7c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-7 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A7.B1 to I.C.A7.B1536).
  • Table 8c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-8 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each indi- vidual compound corresponds in each case to one line of Table B (compounds I.C.A8.B1 to I.C.A8.B1536).
  • Table 9c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-9 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A9.B1 to I.C.A9.B1536).
  • Table 10c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-10 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A10.B1 to I.C.A10.B1536).
  • Table 1 1 c Compounds of the formula I .C in which the combination of R 1 and R 2 corre- sponds to line A-1 1 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A1 1 .B1 to I.C.A1 1 .B1536).
  • Table 12c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-12 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A12.B1 to I.C.A12.B1536).
  • Table 13c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-13 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A13.B1 to I.C.A13.B1536).
  • Table 14c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-14 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A14.B1 to I.C.A14.B1536).
  • Table 15c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-15 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A15.B1 to I.C.A15.B1536).
  • Table 16c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-16 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A16.B1 to I.C.A16.B1536).
  • Table 17c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-17 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A17.B1 to I.C.A17.B1536).
  • Table 18c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-18 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A18.B1 to I.C.A18.B1536).
  • Table 19c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-19 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A19.B1 to I.C.A19.B1536).
  • Table 20c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-20 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A20.B1 to I.C.A20.B1536).
  • Table 21 c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-21 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A21.B1 to I.C.A21 .B1536).
  • Table 22c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-22 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A22.B1 to I.C.A22.B1536).
  • Table 23c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-23 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A23.B1 to I.C.A23.B1536).
  • Table 24c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-24 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A24.B1 to I.C.A24.B1536).
  • Table 25c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-25 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A25.B1 to I.C.A25.B1536).
  • Table 26c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-26 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A26.B1 to I.C.A26.B1536).
  • Table 27c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-27 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A27.B1 to I.C.A27.B1536).
  • Table 28c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-28 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A28.B1 to I.C.A28.B1536).
  • Table 29c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-29 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A29.B1 to I.C.A29.B1536).
  • Table 30c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-30 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A30.B1 to I.C.A30.B1536).
  • Table 31 c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-31 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A31 .B1 to I.C.A31 .B1536).
  • Table 32c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-32 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A32.B1 to I.C.A32.B1536).
  • Table 33c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-33 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A33.B1 to I.C.A33.B1536).
  • Table 34c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-34 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A34.B1 to I.C.A34.B1536).
  • Table 35c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-35 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A35.B1 to I.C.A35.B1536).
  • Table 36c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-36 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A36.B1 to I.C.A36.B1536).
  • Table 37c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-37 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A37.B1 to I.C.A37.B1536).
  • Table 38c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-38 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A38.B1 to I.C.A38.B1536).
  • Table 39c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-39 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A39.B1 to I.C.A39.B1536).
  • Table 40c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-40 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A40.B1 to I.C.A40.B1536).
  • Table 41 c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-41 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A41.B1 to I.C.A41 .B1536).
  • Table 42c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-42 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A42.B1 to I.C.A42.B1536).
  • Table 43c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-43 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A43.B1 to I.C.A43.B1536).
  • Table 44c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-44 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A44.B1 to I.C.A44.B1536).
  • Table 45c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-45 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A45.B1 to I.C.A45.B1536).
  • Table 46c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-46 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A46.B1 to I.C.A46.B1536).
  • Table 47c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-47 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A47.B1 to I.C.A47.B1536).
  • Table 48c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-48 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A48.B1 to I.C.A48.B1536).
  • Table 49c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-49 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A49.B1 to I.C.A49.B1536).
  • Table 50c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-50 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A50.B1 to I.C.A50.B1536).
  • Table 51 c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-51 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A51.B1 to I.C.A51 .B1536).
  • Table 52c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-52 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A52.B1 to I.C.A52.B1536).
  • Table 53c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-53 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A53.B1 to I.C.A53.B1536).
  • Table 54c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-54 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A54.B1 to I.C.A54.B1536).
  • Table 55c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-55 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A55.B1 to I.C.A55.B1536).
  • Table 56c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-56 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A56.B1 to I.C.A56.B1536).
  • Table 57c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-57 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A57.B1 to I.C.A57.B1536).
  • Table 58c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-58 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A58.B1 to I.C.A58.B1536).
  • Table 59c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-59 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A59.B1 to I.C.A59.B1536).
  • Table 60c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-60 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A60.B1 to I.C.A60.B1536).
  • Table 61 c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-61 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A61.B1 to I.C.A61 .B1536).
  • Table 62c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-62 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A62.B1 to I.C.A62.B1536).
  • Table 63c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-63 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A63.B1 to I.C.A63.B1536).
  • Table 64c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-64 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A64.B1 to I.C.A64.B1536).
  • Table 65c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-65 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A65.B1 to I.C.A65.B1536).
  • Table 66c Compounds of the formula I.C in which the combination of R 1 and R 2 corre- sponds to line A-66 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A66.B1 to I.C.A66.B1536).
  • Table 67c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-67 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A67.B1 to I.C.A67.B1536).
  • Table 68c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-68 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A68.B1 to I.C.A68.B1536).
  • Table 69c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-69 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A69.B1 to I.C.A69.B1536).
  • Table 70c Compounds of the formula I.C in which the combination of R 1 and R 2 corresponds to line A-70 of Table A and the meaning for the combination of (R 4 ) m , R 32 , R 33 and R 34 for each individual compound corresponds in each case to one line of Table B (compounds I.C.A70.B1 to I.C.A70.B1536).

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Abstract

La présente invention porte sur des composés de [1,2,4]triazole substitués de formule (I), dans laquelle les substituants sont tels que décrits dans les revendications et la description, et les N-oxydes et sels de ceux-ci, pour lutter contre des champignons phytopathogènes, sur l'utilisation et des procédés pour lutter contre des champignons phytopathogènes et sur des semences enrobées d'au moins un tel composé. L'invention porte également sur des procédés pour préparer ces composés, sur des intermédiaires, sur des procédés pour préparer de tels intermédiaires et sur des compositions comprenant au moins un composé (I).
PCT/EP2013/074008 2012-11-27 2013-11-18 Composés de [1,2,4]triazole substitués WO2014082879A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
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US9815798B2 (en) 2014-03-26 2017-11-14 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10053432B2 (en) 2013-12-12 2018-08-21 Basf Se Substituted [1,2,4]triazole and imidazole compounds
US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
US10450279B2 (en) 2014-06-06 2019-10-22 Basf Se Substituted [1,2,4]triazole compounds

Citations (109)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
EP0077479A2 (fr) 1981-10-10 1983-04-27 Bayer Ag Phénoxyphényl-azolylméthyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides et intermédiaires
GB2130584A (en) 1982-11-23 1984-06-06 Ciba Geigy Ag Microbicidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol-derivatives
EP0113640A2 (fr) 1982-12-14 1984-07-18 Ciba-Geigy Ag 1-Azolyl-2-aryl-3-fluoralcane-2-ols microbicides
EP0126430A2 (fr) 1983-05-19 1984-11-28 Ciba-Geigy Ag Procédé pour la préparation de dérivés de 1-triazolyléthyléthers, composés microbicides contenant des dérivés nouveaux de 1-triazolyl-phenoxyphényléthyléther comme ingrédients actifs et leur application
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0275955A1 (fr) 1987-01-21 1988-07-27 Ciba-Geigy Ag Composition microbicide
DE3801233A1 (de) 1987-01-21 1988-08-04 Ciba Geigy Ag Mikrobizides mittel
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
DE4003180A1 (de) 1990-02-03 1991-08-08 Bayer Ag Halogenallyl-azolyl-derivate
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
US5248500A (en) 1990-12-21 1993-09-28 Del Monte Corporation Slow-release biodegradable granules of pasteuria penetrans
US5403584A (en) 1993-06-30 1995-04-04 Idaho Research Foundation, Inc. Use of Streptomyces WYEC 108 to control plant pathogens
US5422107A (en) 1992-12-25 1995-06-06 Hokkaido Green Kosan, Incorporated Trichoderma harzianum SK-55 fungus, fungicide containing it, and method of manufacture of the same and its use
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
EP0585215B1 (fr) 1989-11-17 1999-09-15 Abbott Laboratories Mutants ou variants de bacillus thuringiensis produisant des quantites elevees d'endotoxine delta
US5968503A (en) 1993-06-30 1999-10-19 Idaho Research Foundation, Inc. Use of streptomyces bacteria to control plant pathogens and degrade turf thatch
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
WO2001040441A2 (fr) 1999-11-29 2001-06-07 Wolfgang Arndt Traitement de semences et de plantes avec des bacteries utiles
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
US20020031495A1 (en) 1998-04-29 2002-03-14 Esperanza Morales Pesticidally active isolate of beauveria bassiana, methods of preparing and using same for pest control in agriculture
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003016303A1 (fr) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Derive de tetrazoyle oxime et produit chimique agricole contenant ledit derive comme principe actif
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003057861A2 (fr) 2002-01-07 2003-07-17 Manas Ranjan Banerjee Rhizobacteries sulfo-oxydantes favorisant la croissance des plantes pour ameliorer le rendement du canola
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
US6955912B2 (en) 2000-03-31 2005-10-18 Yasuharu Sasaki Process for producing Trichoderma harzianum ferm BP-4346
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
US6994849B2 (en) 2001-03-14 2006-02-07 State Of Israel, Ministry Of Agriculture, Agricultural Research Organization Yeast Metschnikowia fructicola NRRL Y-30752 for inhibiting deleterious microorganisms on plants
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2007006670A1 (fr) 2005-07-07 2007-01-18 Basf Aktiengesellschaft Composes de n-thio-anthranilamide et utilisations comme pesticides
US20070088015A1 (en) 2005-10-19 2007-04-19 Roche Palo Alto Llc Non-nucleoside reverse transcriptase inhibitors
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
US7262151B2 (en) 2001-07-06 2007-08-28 Mcgill University Methods and compositions for production of lipo-chito oligosaccharides by rhizobacteria
WO2008002371A1 (fr) 2006-06-23 2008-01-03 Becker Underwood Inc. Durée de conservation avant vente améliorée et stabilisation sur graine d'inoculats bactériens liquides
WO2009090181A2 (fr) 2008-01-15 2009-07-23 Bayer Cropscience Sa Composition pesticide comprenant un dérivé de tétrazolyloxime et une substance active fongicide ou insecticide
WO2009124707A2 (fr) 2008-04-07 2009-10-15 Bayer Cropscience Ag Combinaisons d'agents de lutte biologique et insecticides ou fongicides
WO2009126473A1 (fr) 2008-04-07 2009-10-15 Bayer Cropscience Lp Formulation aqueuse stable contenant des spores
WO2010069882A1 (fr) 2008-12-17 2010-06-24 Syngenta Participations Ag Dérivés d'isoxazole en tant que fongicides
WO2010080169A1 (fr) 2009-01-12 2010-07-15 Bong William L Système et procédé de soudage sous laitier électro-conducteur de colonnes de boîte verticales collées
WO2010080619A2 (fr) 2008-12-19 2010-07-15 Pasteuria Bioscience, Inc. Matériels et méthodes de lutte contre les nématodes avec des spores de pasteuria dans des enrobages de graines
WO2010085795A2 (fr) 2009-01-26 2010-07-29 Pasteuria Bioscience, Inc. Nouvelle souche de pasteuria
WO2010096777A1 (fr) 2009-02-23 2010-08-26 Presidio Pharmaceuticals, Inc. Inhibiteurs du ns5a du vhc
US20100260735A1 (en) 2009-04-13 2010-10-14 University of Delawre Methods for promoting plant health
WO2010146114A1 (fr) * 2009-06-18 2010-12-23 Basf Se Composés de triazole portant un substituant soufré
WO2011022809A1 (fr) 2009-08-28 2011-03-03 University Of Saskatchewan Lutte biologique contre fusarium et les mycotoxines de fusarium
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
WO2011109395A2 (fr) 2010-03-01 2011-09-09 University Of Delaware Compositions et procédés pour l'augmentation de la biomasse, de la concentration en fer et de la résistance aux agents pathogènes dans les plantes
WO2012064527A1 (fr) 2010-11-09 2012-05-18 Pasteuria Bioscience, Inc. Nouvelle souche de pasteuria et ses applications
WO2012079073A1 (fr) 2010-12-10 2012-06-14 Auburn University Agents d'inoculation incluant des bactéries bacillus pour l'induction de la production de composés organiques volatils chez les végétaux
US8206972B2 (en) 2006-12-01 2012-06-26 The United States Of America, As Represented By The Secretary Of Agriculture Growth media and saprophytic use for Pichia anomala
US8221736B2 (en) 1999-12-10 2012-07-17 Rothamsted Research Limited Semiochemical
WO2012168188A1 (fr) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Combinaisons de composés actifs
WO2013007767A1 (fr) 2011-07-13 2013-01-17 Basf Se Composés fongicides 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol substitués
WO2013010862A1 (fr) 2011-07-15 2013-01-24 Basf Se Composés fongicides de 2-[2-chloro-4-(4-chloro-phénoxy)-phényl]-1-[1,2,4]triazol-1-yl-éthanol substitué par alkyle
US20130035230A1 (en) 2009-11-27 2013-02-07 Suchanek Martin Use of fungal organism pythium oligandrum
WO2013024009A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013024010A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013047441A1 (fr) 2011-09-26 2013-04-04 日本曹達株式会社 Composition bactéricide pour l'agriculture et l'horticulture
WO2013047749A1 (fr) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
WO2013127704A1 (fr) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Associations de composés actifs contenant une thiazoylisoxazoline et un fongicide

Patent Citations (113)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325503A (en) 1965-02-18 1967-06-13 Diamond Alkali Co Polychloro derivatives of mono- and dicyano pyridines and a method for their preparation
US3296272A (en) 1965-04-01 1967-01-03 Dow Chemical Co Sulfinyl- and sulfonylpyridines
EP0077479A2 (fr) 1981-10-10 1983-04-27 Bayer Ag Phénoxyphényl-azolylméthyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides et intermédiaires
GB2130584A (en) 1982-11-23 1984-06-06 Ciba Geigy Ag Microbicidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol-derivatives
EP0117378A1 (fr) 1982-11-23 1984-09-05 Ciba-Geigy Ag Dérivés microbicides du 1-carbonyl-1-phénoxyphényl-2-azolyl-éthanol, et leurs intermédiaires
EP0113640A2 (fr) 1982-12-14 1984-07-18 Ciba-Geigy Ag 1-Azolyl-2-aryl-3-fluoralcane-2-ols microbicides
EP0126430A2 (fr) 1983-05-19 1984-11-28 Ciba-Geigy Ag Procédé pour la préparation de dérivés de 1-triazolyléthyléthers, composés microbicides contenant des dérivés nouveaux de 1-triazolyl-phenoxyphényléthyléther comme ingrédients actifs et leur application
EP0141317A2 (fr) 1983-10-21 1985-05-15 BASF Aktiengesellschaft 7-Amino-azolo[1,5-a]pyrimidines et fongicides les contenant
EP0152031A2 (fr) 1984-02-03 1985-08-21 Shionogi & Co., Ltd. Dérivés azolyl cycloalkanols et fongicides agricoles
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
EP0226917A1 (fr) 1985-12-20 1987-07-01 BASF Aktiengesellschaft Esters acryliques et fongicides contenant ces composés
EP0243970A1 (fr) 1986-05-02 1987-11-04 Stauffer Chemical Company Imidates de pyridyle fongicides
EP0256503A2 (fr) 1986-08-12 1988-02-24 Mitsubishi Kasei Corporation Dérivés de pyridinecarboxamide et leur utilisation comme fongicides
EP0275955A1 (fr) 1987-01-21 1988-07-27 Ciba-Geigy Ag Composition microbicide
DE3801233A1 (de) 1987-01-21 1988-08-04 Ciba Geigy Ag Mikrobizides mittel
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0428941A1 (fr) 1989-11-10 1991-05-29 Agro-Kanesho Co., Ltd. Dérivés de l'hexahydrotriazine et insecticides
EP0585215B1 (fr) 1989-11-17 1999-09-15 Abbott Laboratories Mutants ou variants de bacillus thuringiensis produisant des quantites elevees d'endotoxine delta
DE4003180A1 (de) 1990-02-03 1991-08-08 Bayer Ag Halogenallyl-azolyl-derivate
EP0440950A2 (fr) 1990-02-03 1991-08-14 Bayer Ag Dérivés d'halogénoallyl-azole
US5248500A (en) 1990-12-21 1993-09-28 Del Monte Corporation Slow-release biodegradable granules of pasteuria penetrans
EP0532022A1 (fr) 1991-09-13 1993-03-17 Ube Industries, Ltd. Composés acryliques, procédé pour leur préparation et fongicides les contenant
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
US5422107A (en) 1992-12-25 1995-06-06 Hokkaido Green Kosan, Incorporated Trichoderma harzianum SK-55 fungus, fungicide containing it, and method of manufacture of the same and its use
US5403584A (en) 1993-06-30 1995-04-04 Idaho Research Foundation, Inc. Use of Streptomyces WYEC 108 to control plant pathogens
US5968503A (en) 1993-06-30 1999-10-19 Idaho Research Foundation, Inc. Use of streptomyces bacteria to control plant pathogens and degrade turf thatch
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
US6406690B1 (en) 1995-04-17 2002-06-18 Minrav Industries Ltd. Bacillus firmus CNCM I-1582 or Bacillus cereus CNCM I-1562 for controlling nematodes
DE19650197A1 (de) 1996-12-04 1998-06-10 Bayer Ag 3-Thiocarbamoylpyrazol-Derivate
WO1998046608A1 (fr) 1997-04-14 1998-10-22 American Cyanamid Company Trifluoromethylalkylamino-triazolopyrimidines fongicides
WO1999014187A1 (fr) 1997-09-18 1999-03-25 Basf Aktiengesellschaft Derives de benzamidoxime, produits intermediaires et procedes pour les preparer et les utiliser comme fongicides
WO1999024413A2 (fr) 1997-11-12 1999-05-20 Bayer Aktiengesellschaft Amides d'acide isothiazol carboxylique et leur utilisation pour la protection de plantes
WO1999027783A1 (fr) 1997-12-04 1999-06-10 Dow Agrosciences Llc Compositions fongicides, procedes correspondants, composes et procedes concourant a leur elaboration
US20020031495A1 (en) 1998-04-29 2002-03-14 Esperanza Morales Pesticidally active isolate of beauveria bassiana, methods of preparing and using same for pest control in agriculture
WO2000029404A1 (fr) 1998-11-17 2000-05-25 Kumiai Chemical Industry Co., Ltd. Derives de pyrimidinylbenzimidazole et de triazinylbenzimidazole et bactericides agricoles/horticoles
EP1028125A1 (fr) 1998-11-30 2000-08-16 Isagro Ricerca S.r.l. Dipeptides ayant une activité fungizide et leur utilisation agronomique
WO2000046148A1 (fr) 1999-02-02 2000-08-10 Sintokogio, Ltd. Gel de silice a photocatalyseur fortement concentre a base d'oxyde de titane et procede de fabrication correspondant
EP1035122A1 (fr) 1999-03-11 2000-09-13 Rohm And Haas Company Isoxazolidines substituées par des hétérocycles et leur utilisation comme fongicides
WO2000065913A1 (fr) 1999-04-28 2000-11-09 Takeda Chemical Industries, Ltd. Derives de sulfamide
EP1201648A1 (fr) 1999-08-05 2002-05-02 Kumiai Chemical Industry Co., Ltd. Derives de carbamate et bactericides destines a l'agriculture et a l'horticulture
WO2001040441A2 (fr) 1999-11-29 2001-06-07 Wolfgang Arndt Traitement de semences et de plantes avec des bacteries utiles
US8221736B2 (en) 1999-12-10 2012-07-17 Rothamsted Research Limited Semiochemical
DE10021412A1 (de) 1999-12-13 2001-06-21 Bayer Ag Fungizide Wirkstoffkombinationen
WO2001054501A2 (fr) 2000-01-25 2001-08-02 Syngenta Participations Ag Composition herbicide
WO2001056358A2 (fr) 2000-01-28 2001-08-09 Rohm And Haas Company Pesticides dotes de proprietes accrues
EP1122244A1 (fr) 2000-02-04 2001-08-08 Sumitomo Chemical Company, Limited Composés d'uracile et leur usage
US6955912B2 (en) 2000-03-31 2005-10-18 Yasuharu Sasaki Process for producing Trichoderma harzianum ferm BP-4346
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2002022583A2 (fr) 2000-09-18 2002-03-21 E. I. Du Pont De Nemours And Company Pyridinyl-amides et pyridinyl-imides utilisés comme fongicides
WO2002040431A2 (fr) 2000-11-17 2002-05-23 Dow Agrosciences Llc Composes presentant une activite fongicide et leurs procedes de preparation et d'utilisation
US6994849B2 (en) 2001-03-14 2006-02-07 State Of Israel, Ministry Of Agriculture, Agricultural Research Organization Yeast Metschnikowia fructicola NRRL Y-30752 for inhibiting deleterious microorganisms on plants
JP2002316902A (ja) 2001-04-20 2002-10-31 Sumitomo Chem Co Ltd 植物病害防除剤組成物
US7262151B2 (en) 2001-07-06 2007-08-28 Mcgill University Methods and compositions for production of lipo-chito oligosaccharides by rhizobacteria
WO2003010149A1 (fr) 2001-07-25 2003-02-06 Bayer Cropscience Ag Carboxanilides de pyrazolyle utilises comme fongicides
WO2003011853A1 (fr) 2001-07-30 2003-02-13 Dow Agrosciences Llc 6-aryl-4-aminopicolinates et leur utilisation comme herbicides
WO2003014103A1 (fr) 2001-08-03 2003-02-20 Bayer Cropscience S.A. Derives de iodobenzopyran-4-one presentant une activite fongicide
WO2003016286A1 (fr) 2001-08-17 2003-02-27 Sankyo Agro Company, Limited Derive de 3-phenoxy-4-pyridazinol et composition herbicide le contenant
WO2003016303A1 (fr) 2001-08-20 2003-02-27 Dainippon Ink And Chemicals, Inc. Derive de tetrazoyle oxime et produit chimique agricole contenant ledit derive comme principe actif
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2003053145A1 (fr) 2001-12-21 2003-07-03 Nissan Chemical Industries, Ltd. Composition bactericide
WO2003057861A2 (fr) 2002-01-07 2003-07-17 Manas Ranjan Banerjee Rhizobacteries sulfo-oxydantes favorisant la croissance des plantes pour ameliorer le rendement du canola
WO2003061388A1 (fr) 2002-01-18 2003-07-31 Sumitomo Chemical Takeda Agro Company, Limited Compose de sulfonyluree heterocyclique fusionne, herbicide contenant ce compose et procede de controle de plantes nuisibles au moyen de cet herbicide
WO2003064572A1 (fr) 2002-01-31 2003-08-07 Exxonmobil Research And Engineering Company Compositions d'huile lubrifiante a proprietes de reduction du frottement ameliorees
WO2003066609A1 (fr) 2002-02-04 2003-08-14 Bayer Cropscience Aktiengesellschaft Thiazolylcarboxanilides disubstitues et leur utilisation comme microbicides
WO2003074491A1 (fr) 2002-03-05 2003-09-12 Syngenta Participations Ag O-cyclopropyle-carboxanilides et leur utilisation comme fongicides
WO2004049804A2 (fr) 2002-11-29 2004-06-17 Syngenta Participations Ag Combinaisons fongicides pour proteger des cultures
WO2004083193A1 (fr) 2003-03-17 2004-09-30 Sumitomo Chemical Company, Limited Compose amide et composition bactericide contenant ledit compose
WO2005063721A1 (fr) 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2005087772A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005087773A1 (fr) 2004-03-10 2005-09-22 Basf Aktiengesellschaft 5,6-dialkyl-7-amino-triazolopyrimidines, procedes pour leur production, leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant
WO2005120234A2 (fr) 2004-06-03 2005-12-22 E.I. Dupont De Nemours And Company Melanges fongicides de composes d'amidinylphenyle
WO2005123689A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft 1-methyl-3-trifluoromethyl-pyrazol-4-acide carboxylique-(ortho-phenyl)-anilides et leur utilisation comme fongicides
WO2005123690A1 (fr) 2004-06-18 2005-12-29 Basf Aktiengesellschaft (ortho-phenyl)-anilides d'acide 1-methyl-3-difluormethyl-pyrazol-4-carboxylique et leur utilisation comme fongicides
WO2006015866A1 (fr) 2004-08-12 2006-02-16 Syngenta Participations Ag Procédé servant à protéger des plantes utiles ou une matière de propagation de plante
WO2006087325A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft 5-alkoxyalkyl-6-alkyl-7-amino-azolopyrimidines, procede de fabrication de ces composes, utilisation dans la lutte contre des champignons parasites et agents les contenant
WO2006087343A1 (fr) 2005-02-16 2006-08-24 Basf Aktiengesellschaft Anilides d'acide carboxylique pyrazole, procedes de production associes et agents les contenant pour la lutte antifongique
DE102005009458A1 (de) 2005-03-02 2006-09-07 Bayer Cropscience Ag Pyrazolylcarboxanilide
WO2007006670A1 (fr) 2005-07-07 2007-01-18 Basf Aktiengesellschaft Composes de n-thio-anthranilamide et utilisations comme pesticides
US20070088015A1 (en) 2005-10-19 2007-04-19 Roche Palo Alto Llc Non-nucleoside reverse transcriptase inhibitors
WO2007082098A2 (fr) 2006-01-13 2007-07-19 Dow Agrosciences Llc 6-(poly-aryl substituté)-4-aminopicolinates et utilisations de ceux-ci comme herbicides
WO2007090624A2 (fr) 2006-02-09 2007-08-16 Syngenta Participations Ag Procede de protection d'une matiere de propagation vegetale, d'un vegetal et/ou d'un organisme vegetal
WO2008002371A1 (fr) 2006-06-23 2008-01-03 Becker Underwood Inc. Durée de conservation avant vente améliorée et stabilisation sur graine d'inoculats bactériens liquides
US8206972B2 (en) 2006-12-01 2012-06-26 The United States Of America, As Represented By The Secretary Of Agriculture Growth media and saprophytic use for Pichia anomala
WO2009090181A2 (fr) 2008-01-15 2009-07-23 Bayer Cropscience Sa Composition pesticide comprenant un dérivé de tétrazolyloxime et une substance active fongicide ou insecticide
WO2009124707A2 (fr) 2008-04-07 2009-10-15 Bayer Cropscience Ag Combinaisons d'agents de lutte biologique et insecticides ou fongicides
WO2009126473A1 (fr) 2008-04-07 2009-10-15 Bayer Cropscience Lp Formulation aqueuse stable contenant des spores
WO2010069882A1 (fr) 2008-12-17 2010-06-24 Syngenta Participations Ag Dérivés d'isoxazole en tant que fongicides
WO2010080619A2 (fr) 2008-12-19 2010-07-15 Pasteuria Bioscience, Inc. Matériels et méthodes de lutte contre les nématodes avec des spores de pasteuria dans des enrobages de graines
WO2010080169A1 (fr) 2009-01-12 2010-07-15 Bong William L Système et procédé de soudage sous laitier électro-conducteur de colonnes de boîte verticales collées
WO2010085795A2 (fr) 2009-01-26 2010-07-29 Pasteuria Bioscience, Inc. Nouvelle souche de pasteuria
WO2010096777A1 (fr) 2009-02-23 2010-08-26 Presidio Pharmaceuticals, Inc. Inhibiteurs du ns5a du vhc
US20100260735A1 (en) 2009-04-13 2010-10-14 University of Delawre Methods for promoting plant health
WO2010146114A1 (fr) * 2009-06-18 2010-12-23 Basf Se Composés de triazole portant un substituant soufré
WO2011022809A1 (fr) 2009-08-28 2011-03-03 University Of Saskatchewan Lutte biologique contre fusarium et les mycotoxines de fusarium
WO2011028657A1 (fr) 2009-09-01 2011-03-10 Dow Agrosciences Llc Compositions fongicides synergiques contenant un dérivé de 5-fluoropyrimidine pour la lutte contre les champignons dans des céréales
US20130035230A1 (en) 2009-11-27 2013-02-07 Suchanek Martin Use of fungal organism pythium oligandrum
WO2011077514A1 (fr) 2009-12-22 2011-06-30 三井化学アグロ株式会社 Composition permettant de lutter contre des maladies végétales et procédé de lutte contre des maladies végétales par application de la composition
WO2011109395A2 (fr) 2010-03-01 2011-09-09 University Of Delaware Compositions et procédés pour l'augmentation de la biomasse, de la concentration en fer et de la résistance aux agents pathogènes dans les plantes
WO2012064527A1 (fr) 2010-11-09 2012-05-18 Pasteuria Bioscience, Inc. Nouvelle souche de pasteuria et ses applications
US20120149571A1 (en) 2010-12-10 2012-06-14 Auburn University Inoculants Including Bacillus Bacteria for Inducing Production of Volatile Organic Compounds in Plants
WO2012079073A1 (fr) 2010-12-10 2012-06-14 Auburn University Agents d'inoculation incluant des bactéries bacillus pour l'induction de la production de composés organiques volatils chez les végétaux
US8445255B2 (en) 2010-12-10 2013-05-21 Auburn University Inoculants including Bacillus bacteria for inducing production of volatile organic compounds in plants
WO2012168188A1 (fr) 2011-06-07 2012-12-13 Bayer Intellectual Property Gmbh Combinaisons de composés actifs
WO2013007767A1 (fr) 2011-07-13 2013-01-17 Basf Se Composés fongicides 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol substitués
WO2013010862A1 (fr) 2011-07-15 2013-01-24 Basf Se Composés fongicides de 2-[2-chloro-4-(4-chloro-phénoxy)-phényl]-1-[1,2,4]triazol-1-yl-éthanol substitué par alkyle
WO2013024009A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013024010A1 (fr) 2011-08-12 2013-02-21 Basf Se Composés n-thio-anthranilamides et leur utilisation comme pesticides
WO2013047441A1 (fr) 2011-09-26 2013-04-04 日本曹達株式会社 Composition bactéricide pour l'agriculture et l'horticulture
WO2013047749A1 (fr) 2011-09-29 2013-04-04 三井化学アグロ株式会社 Procédé de fabrication de dérivé de 4,4-difluoro-3,4-dihydroisoquinoléine
WO2013127704A1 (fr) 2012-02-27 2013-09-06 Bayer Intellectual Property Gmbh Associations de composés actifs contenant une thiazoylisoxazoline et un fongicide

Non-Patent Citations (54)

* Cited by examiner, † Cited by third party
Title
"e-Pesticide Manual V 5.2", 2008
"McCutcheon's, Vol.1: Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
"Melocont® from Agrifutur, Agrianello, Italy, for control of cockchafer", J. APPL. MICROBIOL., vol. 100, no. 5, 2006, pages 1063 - 72
"Technical Monograph No. 2", May 2008, CROPLIFE INTERNATIONAL, article "Catalogue of pesticide formulation types and international coding system"
AN- GEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 45, no. 35, 2006, pages 5803 - 5807
APPL. ENVIRON. MICROBIOL., vol. 44, no. 5, pages 1096 - 1101
AUSTRAL. J. AGRICULT. RES., vol. 58, 2007, pages 708
BIOLOGICAL CONTROL, vol. 31, no. 2, 2004, pages 145 - 154
BIOLOGICAL CONTROL, vol. 45, 2008, pages 288 - 296
BIOLOGICAL CONTROL, vol. 51, 2009, pages 403 - 408
CAN. J. PLANT SCI., vol. 48, no. 6, 1968, pages 587 - 94
CHMIEL: "Bioprozesstechnik 1. Ein- fuhrung in die Bioverfahrenstechnik", 1991, GUSTAV FISCHER VERLAG
CROP PROTECTION, vol. 25, 2006, pages 468 - 475
CROP PROTECTION, vol. 27, 2008, pages 352 - 361
CURR. MICROBIOL., vol. 59, no. 6, 2009, pages 608 - 615
EUR. J. SOIL BIOL, vol. 45, no. 1, 2009, pages 28 - 35
FERTILIZER RES., vol. 39, 1994, pages 97 - 103
H.D. BURGES: "Formulation of Micobial Biopestcides", 1998, SPRINGER
INT. J. MICROBIOL. RES., vol. 3, no. 2, 2011, pages 120 - 130
J. AGRIC. FOOD. CHEM., vol. 57, 2009, pages 4854 - 4860
J. AM. CHEM. SOC., vol. 123, no. 25, 2001, pages 5962 - 5973
J. BACTERIOL., vol. 192, no. 24, 2010, pages 6486 - 6487
J. HETEROCYC. CHEM., vol. 18, no. 7, 1981, pages 1305 - 8
J. INVERTEBR. PATHOL., vol. 113, no. 1, 2013, pages 104 - 14
J. MED. CHEM., vol. 38, no. 11, 1995, pages 1892 - 903
J. MICROBIOL. BIOTECHNOL., vol. 17, no. 2, 2007, pages 280 - 286
J.AGRIC. FOOD CHEM., vol. 57, 2009, pages 4854 - 4860
JOURNAL OF CHEMICAL RESEARCH, SYNOPSES, 1992, pages 245
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 17, 2012, pages 7384 - 7391
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KNOWLES: "Agrow Reports DS256", 2006, T&F INFORMA, article "Adjuvants and additives"
MICROBIOL. RES., vol. 158, pages 107 - 115
MOL GEN GENOMICS, vol. 272, 2004, pages 1 - 17
MOLLET; GRUBE- MANN: "Formulation technology", 2001, WILEY VCH
MYCOLOGIA, vol. 94, no. 2, 2002, pages 297 - 301
NATURE, vol. 280, 1979, pages 697 - 699
NEW PHYTOL, vol. 179, no. 1, 2008, pages 224 - 235
PEST MANAGEM. SCI., vol. 61, 2005, pages 246
PEST MANAGEM. SCI., vol. 61, 2005, pages 258
PEST MANAGEM. SCI., vol. 61, 2005, pages 277
PEST MANAGEM. SCI., vol. 61, 2005, pages 286
PEST MANAGEN SCI, vol. 61, 2005, pages 269
PEST MANAGEN SCI, vol. 64, 2008, pages 326
PEST MANAGEN SCI, vol. 64, 2008, pages 332
PHYTOPARASITICA, vol. 23, no. 3, 1995, pages 231 - 234
PROC. 9TH INT. AND 1ST LATIN AMERICAN PGPR MEETING, 2012, pages 60
PROC. 9TH INT. AND 1ST LATIN AMERICAN PGPR MEETING, QUIMARA, MEDELLIN, COLOMBIA, 2012, pages 60
SCIENCE, vol. 257, 1992, pages 1 - 132
SCIENCE, vol. 316, 2007, pages 1185
SOIL BIOLOGY & BIOCHEMISTRY, vol. 39, 2007, pages 867 - 876
STORHAS: "Bioreaktoren und periphere Einrichtungen", 1994, VIEWEG VERLAG
SYSTEM APPL. MICROBIOL, vol. 27, 2004, pages 372 - 379
WEED SCI., vol. 57, 2009, pages 108
YU GUAN-PING ET AL: "Synthesis and fungicidal evaluation of 2-arylphenyl ether-3-(1H-1,2,4-triazol-1-yl)propan-2-ol derivatives", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 57, no. 11, 10 June 2009 (2009-06-10), pages 4854 - 4860, XP002659633, ISSN: 0021-8561, [retrieved on 20090507], DOI: 10.1021/JF900222S *

Cited By (4)

* Cited by examiner, † Cited by third party
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US10112913B2 (en) 2014-05-13 2018-10-30 Basf Se Substituted [1,2,4]triazole and imidazole compounds as fungicides
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