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WO2016066639A1 - N-(2-phényléhyle 2-substitué)carboxamides et n-(2-phényléhyle 2-substitué)-thiocarboxamides utilisés comme fongicides - Google Patents

N-(2-phényléhyle 2-substitué)carboxamides et n-(2-phényléhyle 2-substitué)-thiocarboxamides utilisés comme fongicides Download PDF

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Publication number
WO2016066639A1
WO2016066639A1 PCT/EP2015/074864 EP2015074864W WO2016066639A1 WO 2016066639 A1 WO2016066639 A1 WO 2016066639A1 EP 2015074864 W EP2015074864 W EP 2015074864W WO 2016066639 A1 WO2016066639 A1 WO 2016066639A1
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halogen atoms
alkyl
halogen
halogenoalkyl
formula
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Inventor
Anne Decor
Stephen David Lindell
Lothar Willms
Hans-Georg Schwarz
Alexander Sudau
Jörg GREUL
Jürgen BENTING
Pierre-Yves Coqueron
Philippe Desbordes
Norio Sasaki
Valérie TOQUIN
Philippe Rinolfi
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Bayer CropScience AG
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Bayer CropScience AG
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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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
    • A—HUMAN NECESSITIES
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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • the present invention relates to the use of N-(2-substituted 2-phenylethyl)carboxamides and N-(2- substituted 2-phenylethyl)thiocarboxamides for the control of phytopathogenic microorganisms in agriculture, wherein a compound of formula (I) is applied to the phytopathogenic microorganisms, their habitat, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown in an effective amount.
  • the present invention further relates to compositions containing such compounds and methods for the control of phytopathogenic microorganisms on plants, the habitat of such microorganims, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown.
  • Phytopathogenic microorganisms cause a substantial loss in agricultural production including food and industrial crops and are control with compounds having fungicidal activity. To be useful in agriculture these compounds should have a high activity against phytopathogenic microorganisms, a broad spectrum activity against different species of phytopathogenic microorganisms and should be able to be applied in an environmentally safe way.
  • R can represent an hydroxyl or an alkoxy group.
  • R can represent an hydroxyl or an alkoxy group.
  • X can represent a halogen atom or a trifluoromethyl group and R 1 can represent an hydrogen atom or an C1-C4 alkyl group.
  • R 1 can represent an hydrogen atom or an C1-C4 alkyl group.
  • R 7 can be a Ci-Cs-alkyl, C 2 -C8-alkenyl, C 2 -C8-alkynyl, C3-C6- cycloalkyl.
  • this document discloses pyrazole-4-carboxamide derivatives which are substituted with a halogenmethyl at position 3 of the pyrazol.
  • A can represent a Ci-Cs alkylene chain, possibly interrupted by an heteroatom, possibly substituted by a halogen atom, a Ci-Ce alkyl or C3-C6 cycloalkyl, Z can be a carbon atom.
  • Z can be a carbon atom.
  • B can represent a ring and W can, amongst other groups, represent CZ 4 Z 5 , in particular Z 4 or Z 5 can represent an alkoxy group or the like.
  • W can, amongst other groups, represent CZ 4 Z 5 , in particular Z 4 or Z 5 can represent an alkoxy group or the like.
  • this document also discloses pyrazole-4- carboxamide derivatives which are substituted with a halogenmethyl at position 3 of the pyrazol.
  • T oxygen or sulphur
  • n 0, 1, 2, 3, 4 or 5
  • X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, sulfanyl, pentafluoro ⁇ 6 -sulfanyl, formyl, formyloxy, formylamino, (hydroxyimino)-Ci-Cg-alkyl, (Ci- C8-alkoxyimino)-Ci-C8-alkyl, (C2-C8-alkenyloxyimino)-Ci-C8-alkyl, (C3-C8-alkynyloxyimino)-Ci-C8- alkyl, (benzyloxyimino)-Ci-C8-alkyl, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 9 halogen atoms, C2-C8-al
  • Z 1 represents hydrogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs- alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl;
  • Z 2 and Z 3 independently represent hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 6 groups Q which can be the same or different;
  • Z a represents Ci-Cs-alkyl, C3-Cs-alkenyl, C3-Cs-alkynyl, C3-C7-cycloalkyl, (C3-C7-cycloalkyl)-Ci- C8-alkyl, aryl-Ci-Cs-alkyl, optionally substituted by 1 to 6 groups Q which can be the same or different, Ci-C6-alkylideneamino;
  • Q represents halogen, cyano, nitro, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 9 halogen atoms, Ci- C8-alkoxy, Ci-Cs-halogenoalkoxy having 1 to 9 halogen atoms, Ci-Cs-alkylsulfanyl, Ci-Cs- halogenoalkylsulfanyl having 1 to 9 halogen atoms, tri-(Ci-C8-alkyl)-silyl, tri-(Ci-C8-alkyl)-silyl-Ci- C8-alkyl, Ci-Cs-alkoxyimino-Ci-Cg-alkyl, (benzyloxyimino)-Ci-Cg-alkyl;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 ) - -
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 3 )
  • R 7 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 8 represents hydrogen or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, amino, C1-C5- alkoxy, Ci-Cs-alkylsulfanyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or C1-C5- halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 ) - -
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, amino, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, amino, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-Cs-alkoxycarbonyl, C1-C5- alkyl, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 7 )
  • R 19 represents hydrogen or substituted or unsubstitued Ci-Cs-alkyl, and . .
  • R 20 to R 22 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C 1 -C5- halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 8 )
  • R 23 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 24 represents hydrogen or Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or A represents a heterocycle of formula (A 9 )
  • R 25 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 26 represents hydrogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di-(Ci- C5-alkyl)-amino; or
  • A represents a heterocycle of formula (A 11 ) - -
  • R 29 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di-(Ci- C5-alkyl)-amino; or
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-Cs-alkyl
  • R 32 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, nitro, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 )
  • R 34 represents hydrogen, halogen, Ci-Cs-alkyl, C3-Cs-cycloalkyl, Ci-Cs-alkoxy, C3-Cs-alkynyloxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, and . .
  • R 35 represents hydrogen, halogen, Ci-Cs-alkyl, cyano, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di-(Ci-C5-alkyl)-amino, and
  • R 36 represents a hydrogen atom or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, C 1 -C5- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy or a Ci-Cs-alkylsulfanyl, and
  • R 39 represents hydrogen or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 15 )
  • R 40 and R 41 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C 1 -C5- halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 16
  • R 42 and R 43 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, C 1 -C5- halogenoalkyl comprising 1 to 9 halogen atoms or amino; or
  • A represents a heterocycle of formula (A 17 ) - -
  • R 44 and R 45 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 18 )
  • R 47 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 46 represents hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-Cs-alkylsulfanyl; or
  • A represents a heterocycle of formula (A 19 )
  • R 49 and R 48 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci- C5-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 20 )
  • R 50 and R 51 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl, Ci-Cs-alkoxy, Ci- C5-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 21 )
  • R 52 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 22 )
  • R 53 represents hydrogen, halogen, Ci-Cs-alkyl or Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 23 )
  • R 54 and R 56 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 55 represents hydrogen or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 24 ) _ .
  • R 57 and R 59 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5 halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 58 represents hydrogen or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 25 )
  • R 60 and R 61 independently from each other represent hydrogen, halogen, Ci-Cs-alkyl or C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 62 represents a hydrogen atom or Ci-Cs-alkyl
  • A represents a heterocycle of formula (A 26 )
  • R 63 represents hydrogen, halogen, Ci-Cs-alkyl, cyano, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, C1-C5- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-Cs-alkylamino or di(Ci-C5-alkyl)amino, and
  • R 64 represents hydrogen or Ci-Cs-alkyl
  • R represents hydrogen, halogen, Ci-Cs-alkyl, C3-Cs-cycloalkyl, Ci-Cs-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-Cs-alkoxy, C3-Cs-alkynyloxy or Ci-Cs-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula A 27 )
  • R 66 represents hydrogen, halogen, hydroxy, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, Ci-C i-alkylsulfanyl, Ci-C i-halogenoalkylsulfanyl having 1 to 5 halogen atoms and Ci-C i-halogenoalkoxy having 1 to 5 halogen atoms, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, cyano, Ci-C i-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, SCi-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-Cs-alkylsulfanyl, C2-C5-alkenylsulfanyl, C1-C4- halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, hydroxy, cyano, Ci- C i-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-, -SO-, -S0 2 - and -CH 2 -, and
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl; or
  • A represents a heterocycle of formula (A 31 )
  • R 81 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms;
  • A represents a heterocycle of formula (A 32 ) in which
  • R 82 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms;
  • SO represents a sulfoxyde group
  • SO2 represents a sulfone group
  • an alkyl group, an alkenyl group and an alkynyl group as well as moieties containing these terms can be linear or branched.
  • aryl also in terms like arylalkyl, arylalkenyl, arylalkynyl, aryloxy means phenyl or naphthyl, wherein phenyl is optionally substituted by 1 to 5 groups Q, and naphtyl is optionally substituted by 1 to 6 groups Q.
  • heterocyclyl means a saturated or unsaturated 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered ring comprising 1 to 4 heteroatoms selected from the list consisting of oxygen (O), nitrogen (N), and sulphur (S).
  • Heteroatom means an atom selected from the group consisting of O, N, and S.
  • halogenated radical like e.g. halogenoalkyl, halogenoalkoxy
  • those halogen atoms can be the same or different.
  • Ci-Cs-alkyl comprises the largest range defined here for an alkyl radical. Specifically, this definition comprises the meanings methyl, ethyl, n , isopropyl, n , iso , sec , tert-butyl, and also in each case all isomeric pentyls, hexyls, heptyls and octyls, such as methyl, ethyl, propyl, 1 -me-thylethyl, butyl, 1 -methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1 -methylbutyl, 2-methylbutyl, 3- methylbutyl, 1 ,2-dimethylpropyl, 1 , 1 -dimethylpropyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1- methylpentyl, 2-methylpent
  • a preferred range is Cl-C4-alkyl, such as methyl, ethyl, n , isopropyl, n , iso , sec , tert-butyl.
  • the definition Cl-C3-alkyl comprises methyl, ethyl, n , isopropyl.
  • halogen comprises fluorine, chlorine, bromine and iodine.
  • Ci-Cs-halogenoalkyl - represents, for example, Ci-Cs-alkyl as defined above substituted by one or more halogen substituents which can be the same or different.
  • Ci-Cs-haloalkyl represents chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 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, 2,2,2-trichloroethyl, pentafluoroethyl, 1-fluoro-l-methylethyl, 2-fluoro-l,l-dimethylethyl, 2-chloro-l,l-dimethylethyl, 2-fluoro-l -fluoromethyl- 1 -methylethyl, 2- fluoro
  • C2-C8-alkenyl comprises the largest range defined here for an alkenyl radical. Specifically, this definition comprises the meanings ethenyl, n , isopropenyl, n , iso , sec , tert-butenyl, and also in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls, 1 -methyl- 1-propenyl, 1- ethyl-l-butenyl, 2,4-dimethyl-l-pentenyl, 2,4-dimethyl-2-pentenyl.
  • Halogen-substituted alkenyl - referred to as C2-C8-halogenoalkenyl - represents, for example, C2-C8-alkenyl as defined above substituted by one or more halogen substituents which can be the same or different.
  • C2-C8-alkynyl comprises the largest range defined here for an alkynyl radical. Specifically, this definition comprises the meanings ethynyl, n , isopropynyl, n , iso , sec , tert-butynyl, and also in each case all isomeric pentynyls, hexynyls, heptynyls, octynyls.
  • Halogen-substituted alkynyl - referred to as C2-C8-halogenoalkynyl - represents, for example, C2-C8— alkynyl as defined above substituted by one or more halogen substituents which can be the same or different.
  • C3-C7-cycloalkyl comprises monocyclic saturated hydrocarbyl groups having 3 to 7 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • halogen-substituted cycloalkyl and halocycloalkyl comprises monocyclic saturated hydrocarbyl groups having 3 to 7 carbon ring members, such as 1 -fluoro-cyclopropyl, 1-chloro- cyclopropyl, 1 -bromo-cyclopropyl, 2,2-dichloro- 1 -methyl-cyclopropyl, 2,2-dibromo-l-methyl- cyclopropyl, 1 -fluoro-cyclobutyl, 1 -chloro-cyclobutyl, 1 -fluoro-cyclopentyl, 1 -chloro-cyclopentyl, 1- fluoro-cyclohexyl or 1 -chloro-cyclohexyl.
  • Compounds of the present invention can exist in one or more optical or chiral isomer forms depending on the number of asymmetric centres in the compound.
  • the invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic” denotes a mixture of enantiomers in different proportions) and to the mixtures of all the possible stereoisomers, in all proportions.
  • the diastereoisomers and/or the optical isomers can be separated according to the methods which are known per se by the man ordinary skilled in the art.
  • Compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound.
  • the invention thus relates equally to all geometric _ _ isomers and to all possible mixtures, in all proportions.
  • the geometric isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.
  • Compounds of the present invention can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents of ring B.
  • the invention thus relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions.
  • the syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.
  • any of the compounds of formula (I) wherein X represents a hydroxy, a sulfanyl or an amino may be found in its tautomeric form resulting from the shift of the proton of said hydroxy, sulfanyl or amino group.
  • Such tautomeric forms of such compounds are also part of the present invention. More generally speaking, all tautomeric forms of compounds of formula (I) wherein X represents a hydroxy, a sulfanyl group or an amino group, as well as the tautomeric forms of the compounds which can optionally be used as intermediates in the preparation processes and which will be defined in the description of these processes, are also part of the present invention.
  • Agriculture shall encompass the production of food and feed crops, forestry, the protection of stored products including food, feed but also other materials of plant origin.
  • Preferably agriculture shall encompass the production of food and feed crops, forestry, the protection of stored products being food, feed, and materials of plant origin.
  • Plant product mean any product derived from a plant.
  • control of phytopathogenic microorganisms means a reduction in infestation by phytopathogenic microorganisms, compared with the untreated plant, the seed of a plant, the plant propagation material or the plant product, measured as efficacy, preferably a reduction by 25-50 %, compared with the untreated plant, the seed of a plant, the plant propagation material or the plant product (100 %), more preferably a reduction by 40-79 %, compared with the the untreated plant, the seed of a plant, the plant propagation material or the plant product (100 %); even more preferably, the infection by phytopathogenic microorganisms is entirely suppressed (by 70-100 %).
  • the control may be curative, i.e. for treatment of the plant, the seed of a plant, the plant propagation material or the plant product or protective, for protection of the untreated plant, the seed of a plant, the plant propagation material or the plant product, which have not yet been infected.
  • an "effective amount” means an amount of the inventive compound which is sufficient to control the phytopathogenic microorganism in a satisfactory manner or to eradicate the phytopathogenic microorganism completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example on the phytopathogenic microorganism to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions. _ _
  • Phytopathogenic microorganisms mean fungi and bacteria capable of infecting a plant, a seed of a plant, a plant propagation material or a plant product.
  • phytopathogenic microorganisms mean phytopathogenic fungi.
  • Fungi mean Plasmodiophoromycetes, Peronosporomycetes (Syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (Syn. Fungi imperfecti).
  • Bacteria mean species of the phylum baceteria including Pseudomonadaceae, Rhizobiaceae, Enter obacteriaceae, Corynebacteriaceae and Streptomycetaceae capable of infecting a plant, a seed of a plant, a plant propagation material or a plant product.
  • the formula (I) provides a general definition of the N-(2-substituted 2-phenylethyl)carboxamides and N- (2-substituted 2-phenylethyl)thiocarboxamides according to the invention. Preferred radical definitions for the formula (I) shown above are given below.
  • the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture,
  • T oxygen
  • n 0, 1, 2, 3, 4 or 5
  • X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, sulfanyl, pentafluoro ⁇ 6 -sulfanyl, formyl, formyloxy, formylamino, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, C2- C4-alkenyl, C 2 -C4-halogenoalkenyl having 1 to 9 halogen atoms, C 2 -C4-alkynyl, C 2 -C4-halogenoalkynyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkylamino, di-(Ci-
  • Z 1 represents hydrogen, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- alkoxy, Ci-C4-alkylsulfanyl, or Ci-C4-alkoxycarbonyl;
  • Z 2 and Z 3 independently represent hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, or Ci-C4-alkoxycarbonyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 6 groups Q which can be the same or different;
  • Z a represents Ci-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl, C3-C7-cycloalkyl, (C3-C7-cycloalkyl)-Ci- C4-alkyl, aryl-Ci-C4-alkyl, optionally substituted by 1 to 6 groups Q which can be the same or different, Ci-C4-alkylideneamino;
  • Q represents halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci- C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkylsulfanyl having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)-silyl, tri-(Ci-C4-alkyl)-silyl-Ci- C4-alkyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, (benzyloxyimino)-Ci-C4-alkyl;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, amino, C 1 -C4- alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or C1-C4- halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and - -
  • R and R independently from each other represent hydrogen, halogen, Ci-C i-alkoxycarbonyl, C 1 -C4- alkyl, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-C4-alkylamino or di-(Ci- C4-alkyl)-amino; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-C4-alkylamino or di-(Ci- C4-alkyl)-amino; or
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C i-alkyl
  • R 32 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 )
  • R represents hydrogen, halogen, Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, C3-C4-alkynyloxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, cyano, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-C4-alkylamino or di-(Ci-C4-alkyl)-amino, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R and R independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or a Ci-C4-alkylsulfanyl, and
  • R 39 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 27 ) - -
  • R 66 represents hydrogen, halogen, hydroxy, cyano, Ci-C i-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkylsulfanyl having 1 to 5 halogen atoms and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, SCi-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C2-C4-alkenylsulfanyl, C1-C4- halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, hydroxy, cyano, Ci- C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-alkylsulfanyl, - -
  • Ci-C4-halogenoalkylsulfanyl having 1 to 5 halogen atoms Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, Ci-C4-alkylsulfinyl and Ci-C4-alkylsulfonyl; or
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-, -SO-, -S0 2 - and -CH 2 -, and
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl
  • the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture,
  • T oxygen
  • n 0, 1, 2, 3, 4 or 5
  • X independently from each other X represents halogen, nitro, cyano, isonitrile, hydroxy, amino, carboxy, carbamoyl, thiocarbamoyl, N-hydroxycarbamoyl, carbamate, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 9 halogen atoms, C 2 -C4-alkenyl, C 2 -C4-halogenoalkenyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkylamino, di-(Ci-C4-alkyl)-amino, C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 9 halogen atoms, C3- Cv-cycloalkoxy, (C3-C 7 -cycloalky
  • Z 1 represents hydrogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- alkoxy, or Ci-C4-alkoxycarbonyl; _ _
  • Z 2 and Z 3 independently represent hydrogen, halogen, cyano, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C i-alkoxy, or Ci-C i-alkoxycarbonyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle, which is optionally substituted by 1 to 4 groups Q which can be the same or different;
  • Z a represents Ci-C i-alkyl, C3-C i-alkenyl, C3-C i-alkynyl, Cs-Cs-cycloalkyl, (C3-C5-cycloalkyl)-Ci- C i-alkyl, aryl-Ci-C i-alkyl, optionally substituted by 1 to 6 groups Q which can be the same or different;
  • Q represents halogen, cyano, nitro, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 9 halogen atoms, Ci- C i-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)-silyl;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-alkoxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, amino, C 1 -C4- alkoxy, Ci-C4-alkylsulfanyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or C1-C4- halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C4-alkoxycarbonyl, C 1 -C4- alkyl, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-C4-alkylamino or di-(Ci- C4-alkyl)-amino; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, Ci-C4-alkylamino or di-(Ci- C4-alkyl)-amino; or
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl
  • R 32 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, nitro, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 ) - -
  • R 34 represents hydrogen, halogen, Ci-C i-alkyl, C3-C i-cycloalkyl, Ci-C4-alkoxy, C3-C4-alkynyloxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, cyano, Ci-C4-alkoxy, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino, C1-C4- alkylamino or di-(Ci-C4-alkyl)-amino, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, or Ci-C4-alkoxy, and
  • R 39 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 27 )
  • R 66 represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms, and - -
  • R , R and R independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula A 28 )
  • R 70 represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, hydroxy, cyano, Ci- C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-, -SO-, -SO2- and -CH 2 -, and
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl
  • the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture,
  • T oxygen
  • n 0, 1 , 2, 3 or 4;
  • X independently from each other X represents halogen, nitro, cyano, hydroxy, amino, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 9 halogen atoms, C 2 -C i-alkenyl, C 2 -C4-halogenoalkenyl having 1 to 9 halogen atoms, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy having 1 to 9 halogen atoms, Ci-C4-alkylamino C3-C7-cycloalkyl, C3-C7-halogenocycloalkyl having 1 to 9 halogen atoms;
  • Z 1 represents hydrogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms;
  • Z 2 and Z 3 independently represent hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, or Ci-C4-alkoxycarbonyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 4-membered, saturated carbocycle, which is optionally substituted by 1 to 4 groups Q which can be the same or different;
  • Z a represents Ci-C4-alkyl, C3-C4-alkenyl, C3-C4-alkynyl, C3-C4-cycloalkyl, (C3-C4-cycloalkyl)-Ci- C 2 -alkyl, aryl-Ci-C 2 -alkyl;
  • Q represents halogen, cyano, nitro, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms, Ci- C4-alkoxy;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, or Ci-C4-alkoxy; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, or Ci-C4-alkoxy; or
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, amino, C1-C4- alkoxy, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-alkoxy, amino, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and R 17 represents hydrogen or Ci-C i-alkyl; or
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C i-halogenoalkoxy comprising 1 to 9 halogen atoms, amino; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-alkoxy, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, amino; or
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl
  • R 32 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and - -
  • R represents hydrogen, halogen, nitro, Ci-C i-alkyl, Ci-C i-alkoxy, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 )
  • R represents hydrogen, halogen, Ci-C4-alkyl, C3-C4-cycloalkyl, Ci-C4-alkoxy, C3-C4-alkynyloxy or Ci-C4-halogenoalkoxy comprising 1 to 9 halogen atoms, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, cyano, Ci-C4-alkoxy, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, or Ci-C4-alkoxy, and
  • R 39 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula A 27 )
  • Ci-C4-alkyl represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy, and - -
  • R , R and R independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, hydroxy, cyano, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogen, cyano, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, hydroxy, cyano, Ci- C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C4-alkoxy; or
  • A represents a heterocycle of formula A 30 )
  • X 1 represents -S-
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl
  • the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in . . agriculture,
  • T oxygen
  • n 0, 1 , 2 or 3;
  • X independently from each other X represents halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 9 halogen atoms, Ci-C i-alkoxy, Ci-C i-halogenoalkoxy having 1 to 9 halogen atoms;
  • Z 1 represents hydrogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms;
  • Z 2 and Z 3 independently represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a cyclopropyl
  • Z a represents Ci-C i-alkyl, C3-C i-alkenyl, C3-C4-alkynyl, C3-C4-cycloalkyl, (C3-C4-cycloalkyl)-Ci- C2-alkyl, benzyl-Ci-C2-alkyl;
  • Q represents halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 9 halogen atoms;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 4 ) - -
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 10 ) . .
  • R 27 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C i-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, amino; or
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl
  • R 32 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 ) - -
  • R 34 represents hydrogen, halogen, Ci-C i-alkyl, C3-C4-cycloalkyl, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 39 represents hydrogen or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 27 )
  • R 66 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 28 ) - -
  • R 70 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogenCi-C4-alkyl, or C 1 -C4- halogenoalkyl having 1 to 5 halogen atom; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl
  • the present invention provides the use of a compound of formula (I) as defined above or an N-oxide or optically active isomer thereof, for control of phytopathogenic microorganisms in agriculture,
  • T oxygen
  • n 0, 1 or 2; _ _
  • X independently from each other X represents fluorine, chlorine
  • Z 1 represents hydrogen
  • Z 2 and Z 3 independently represent hydrogen, Ci-C2-alkyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a cyclopropyl
  • Z a represents Ci-C i-alkyl, allyl, prop-2-yn-l -yl, methylbenzyl, cyclopropylmethyl;
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C2-alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C2-alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C2-alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 5 ) _ _
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 14 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 17 represents hydrogen or Ci-C 2 -alkyl
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • R 28 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • A represents a heterocycle of formula (A 11 ) - -
  • R 29 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • R 30 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C 2 -alkyl
  • R 32 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • R 33 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl
  • A represents a heterocycle of formula (A 13 )
  • R 34 represents hydrogen, halogen, Ci-C 2 -alkyl
  • R 35 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and R 36 represents a hydrogen atom or Ci-C 2 -alkyl;
  • A represents a heterocycle of formula (A 14 ) - -
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 39 represents hydrogen or Ci-C 2 -alkyl
  • A represents a heterocycle of formula A 27 )
  • R 66 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl; or
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-
  • R 78 represents Ci-C 2 -alkyl, fluoromethyl, difluoromethyl, trifluoromethyl, and
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C 2 -alkyl
  • Q represents halogen, cyano, nitro, Ci- C i-alkyl, Ci- C i-halogenoalkyl having 1 to 5 halogen atoms, Ci-C C i-alkoxy, Ci- C i-halogenoalkoxy having 1 to 9 halogen atoms, tri-(Ci-C4-alkyl)- silyl, tri-(Ci-C4-alkyl)-silyl-Ci-C4-alkyl, Ci-C4-alkoxyimino-Ci-C4-alkyl, (benzyloxyimino)-Ci-C4-alkyl.
  • Q represents halogen, cyano, nitro, Ci- C4-alkyl, Ci- C4-halogenoalkyl having 1 to 5 halogen atoms, Ci-C C4-alkoxy, Ci- C4-halogenoalkoxy having 1 to 9 halogen atoms, tri-(Ci-C4- alkyl)-silyl, tri-(Ci-C 4 -alkyl)-silyl-Ci-C 4 -alkyl.
  • Q represents halogen, cyano, Ci- C3-alkyl, Ci- C3-halogenoalkyl having 1 to 5 halogen atoms, Ci-C C3-alkoxy, Ci- C3-halogenoalkoxy having 1 to 9 halogen atoms.
  • Q represents fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 1 ) - -
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms;
  • n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms;
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 1 )
  • R 1 to R 3 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 2 )
  • R 4 to R 6 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms;
  • n, T, X, Z 1 ,Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, or C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 4 )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above. - -
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A )
  • R 9 to R 11 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 5 )
  • R 12 and R 13 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, or C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 14 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; n, T, X, Z 1 ,Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and . .
  • R 17 represents hydrogen or Ci-C i-alkyl
  • n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, or C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-C i-alkyl
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 6 )
  • R 15 represents hydrogen, halogen, cyano, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 16 and R 18 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, or C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 17 represents hydrogen or Ci-C4-alkyl
  • the compound of fonnula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C i-alkyl, C i-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, C i-C4-halogenoalkyl comprising 1 to 9 halogen atoms, amino;
  • n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 11 )
  • R 29 represents hydrogen, halogen, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, amino;
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 10 )
  • R 27 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 28 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 11 ) - -
  • R 29 represents hydrogen, halogen, Ci-C i-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 30 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, amino;
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl
  • R 32 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 )
  • R represents hydrogen, halogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and . .
  • R 35 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 36 represents a hydrogen atom or Ci-C i-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 39 represents hydrogen or Ci-C4-alkyl;n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl
  • R 32 represents hydrogen, halogen, Ci-C4-alkyl or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, Ci-C4-alkyl, or Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 ) - -
  • R 34 represents hydrogen, halogen, Ci-C i-alkyl, C3-C4-cycloalkyl, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C 1 -C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 39 represents hydrogen or Ci-C4-alkyl;n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 12 )
  • R 31 represents hydrogen or Ci-C4-alkyl, and . .
  • R 32 represents hydrogen, halogen, Ci-C i-alkyl or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 33 represents hydrogen, halogen, Ci-C i-alkyl, or Ci-C i-halogenoalkyl comprising 1 to 9 halogen atoms; or
  • A represents a heterocycle of formula (A 13 )
  • R represents hydrogen, halogen, Ci-C4-alkyl, C3-C4-cycloalkyl, and
  • R 35 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 36 represents a hydrogen atom or Ci-C4-alkyl
  • A represents a heterocycle of formula (A 14 )
  • R 37 and R 38 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C1-C4- halogenoalkyl comprising 1 to 9 halogen atoms, and
  • R 39 represents hydrogen or Ci-C4-alkyl
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula A 27 )
  • R 66 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, Ci-C/i-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogenCi-C4-alkyl, or C1-C4- halogenoalkyl having 1 to 5 halogen atom; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms;
  • n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 27 )
  • R 66 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and . .
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, Ci-C i-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 28 )
  • R 70 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogenCi-C4-alkyl, or C1-C4- halogenoalkyl having 1 to 5 halogen atom; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms;
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula A 27 )
  • R 66 represents hydrogen, halogen, Ci-C4-alkyl, Ci-C4-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 67 , R 68 and R 69 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms; or
  • A represents a heterocycle of formula (A 28 ) _ _
  • R 70 represents hydrogen, halogen, Ci-C i-alkyl, Ci-C i-halogenoalkyl having 1 to 5 halogen atoms, and
  • R 71 , R 72 and R 73 independently from each other represent hydrogen, halogenCi-C4-alkyl, or C1-C4 halogenoalkyl having 1 to 5 halogen atom; or
  • A represents a heterocycle of formula (A 29 )
  • R 74 , R 75 , R 76 and R 77 independently from each other represent hydrogen, halogen, Ci-C4-alkyl, C1-C4 halogenoalkyl having 1 to 5 halogen atoms;
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-
  • R 78 represents Ci-C4-alkyl and Ci-C4-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C4-alkyl
  • n, T, X, Z 1 and Z 2 , Z 3 , Z a and Q have the preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 30 ) - -
  • X 1 represents -S-
  • R 78 represents Ci-C i-alkyl and Ci-C i-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C i-alkyl
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the more preferred meaning described above.
  • the compound of formula (I) as defined above is a compound
  • A represents a heterocycle of formula (A 30 )
  • X 1 represents -S-
  • R 78 represents Ci-C i-alkyl and Ci-C i-halogenoalkyl having 1 to 5 halogen atoms
  • R 79 and R 80 independently from each other represent hydrogen and Ci-C i-alkyl
  • n, T, X, Z 1 , Z 2 , Z 3 , Z a and Q have the even more preferred meaning described above.
  • the compounds disclosed in the present invention can be preparted, according to a process PI as herein- defined and wherein T represents O and that comprises reaction of an amine of formula (II- 1) or one of its salts
  • Z 2 and Z 3 independently represent halogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl, or _ .
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 6 groups Q which can be the same or different,
  • Amine derivatives of formula (II- 1) are known or can be prepared by known processes such as reductive amination of aldehydes or ketones (Organic Reactions (Hoboken, NJ, United States) (2002), 59,), or reduction of oximesnitro and azido groups, or nucleophilic substitution of a halogen, mesylate or tosylate (Journal of Medicinal Chemistry (2002), 45, 3887).
  • Carboxylic acid derivatives of formula (III-l) are known or can be prepared by known processes.
  • Suitable condensing agent may be selected in the non-limited list consisting of acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as ⁇ , ⁇ '-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, ⁇ , ⁇ '-carbonyl-diimidazole, 2-ethoxy-N- ethoxycarbonyl-l,2-dihydroquinoline
  • acid halide former such as phosgene, phosphorous tribromide, phospho
  • Process PI is conducted in the presence of a catalyst.
  • Suitable catalyst may be selected in the list consisting of N,N-dimethylpyridin-4-amine, 1-hydroxy-benzotriazole or N,N-dimethylformamide.
  • process PI is conducted in the presence of an acid binder.
  • Suitable acid binders for carrying out process PI according to the invention are in each case all inorganic and organic bases that are customary for such reactions.
  • Suitable solvents for carrying out process PI can be customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane; ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1 ,2-dimethoxyethane, 1 ,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile,
  • the amine derivative of formula (II) can be employed as its salt, such as chlorhydrate or any other convenient salt.
  • reaction components in other ratios. Work-up is carried out by known methods.
  • Z 2 and Z 3 independently represent halogen, cyano, Ci-Cs-alkyl, Ci-Cs-halogenoalkyl having 1 to 5 halogen atoms, Ci-Cs-alkoxy, Ci-Cs-alkylsulfanyl, or Ci-Cs-alkoxycarbonyl, or
  • Z 2 and Z 3 form together with the carbon atom to which they are attached a 3- to 6-membered, saturated carbocycle or saturated heterocycle, which is optionally substituted by 1 to 6 groups Q which can be the same or different,
  • Process P2 according to the invention is performed in the presence of a thionating agent.
  • Amide derivatives of formula (I) wherein T represents O can be prepared according to process PI .
  • Suitable thionating agents for carrying out process P2 according to the invention can be sulfur (S), sulfhydric acid (H2S), sodium sulfide (Na2S), sodium hydrosulfide (NaHS), boron trisulfide (B2S3), bis(diethylaluminium) sulfide ((AlEt2)2S), ammonium sulfide ((NH ⁇ S), phosphorous pentasulfide (P2S5), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-l ,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer-supported thionating reagent such as described in Journal of the Chemical Society, Perkin 1 (2001), 358, in the optionally presence of a catalytic or stoichiometric or excess amount, quantity of a base such as an inorganic and organic base.
  • alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate
  • heterocyclic aromatic bases such as pyridine, picoline, lutidine, collidine
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, ⁇ , ⁇ -dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine.
  • Suitable solvents for carrying out process P2 can be customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichlorethane or trichlorethane, ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1 ,2-dimethoxyethane or 1 ,2-diethoxyethane, nitriles, such as acetonitrile, propionitrile, n-
  • Processes PI and P2 are generally carried out under atmospheric pressure. It is also possible to operate under elevated or reduced pressure.
  • reaction temperatures can be varied within a relatively wide range. In general, these processes are carried out at temperatures from 0 °C to 200 °C, preferably from 10 °C to 160 °C.
  • a way to control the temperature for the processes according to the invention is to use micro-wave technology.
  • reaction mixture is concentrated under reduced pressure.
  • residue that remains can be freed by known methods, such as chromatography or crystallization, from any impurities that can still be present.
  • reaction mixture is treated with water and the organic phase is separated and, after drying, concentrated under reduced pressure. If appropriate, any impurities that may still be present the remaining residue can be removed by customary methods, such as chromatography, crystallization or distillation.
  • the compound according to the present invention can be prepared according to the processes described above. It will nevertheless be understood that, on the basis of his general knowledge and of available publications, the skilled worker will be able to adapt this method according to the specifics of each of the compounds, which it is desired to synthesize.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the microorganisms and/or in their habitat.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the plant or plant parts.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to plant propagation material.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the seed.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown.
  • the invention also relates to a method for controlling phytopathogenic microorganisms, characterized in that a compound of the formula (I) is applied to the microorganisms and/or in their habitat.
  • the invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to the plant or plant parts.
  • the invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to plant propagation material.
  • the invention also relates to a method for controlling phytopathogenic fungi, characterized in that a compound of the formula (I) is applied to the seed.
  • the invention also relates to a method for controlling phytopathogenic fungi, characterized in a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown.
  • the invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied to the plant or plant parts.
  • the invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied to plant propagation material.
  • the invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is are applied to the seed.
  • the invention also relates to a method for controlling phytopathogenic bacteria, characterized in that a compound of the formula (I) is applied the soil on which the plants are grown or intended to be grown.
  • the invention further relates to seed which has been treated with at least one compound of the formula (I).
  • the invention finally provides a method for protecting seed against phytopathogenic microorganisms by using seed treated with at least one compound of the formula (I).
  • the compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic microorganisms in agriculture.
  • a compound of the formula (I) can be used for control of phytopathogenic microorganisms in crop protection and in the protection of materials.
  • the compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic fungi in agriculture.
  • a compound of the formula (I) can be used for control of phytopathogenic fungi in crop protection and in the protection of materials.
  • the compounds of the formula (I) have potent microbicidal activity and can be used for control of phytopathogenic bacteria in agriculture.
  • a compound of the formula (I) can be used for control of phytopathogenic bacteria in crop protection and in the protection of materials.
  • the compounds of the formula (I) can be used for curative or protective control of phytopathogenic microorganisms.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic microorganisms by the use of the inventive active ingredients or compositions, which are applied to the the phytopathogenic microorganisms, their habitat, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown.
  • the compounds of the formula (I) can be used for curative or protective control of phytopathogenic bacteria.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic bacteria by the use of the inventive active ingredients or compositions, which are applied to the the phytopathogenic bacteria, their habitat, the plant, the seed thereof, plant parts, plant propagation material or the soil on which the plants are grown or intended to be grown.
  • the compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic microorganisms, in particular phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the phytopathogenic fungi, their habitat, the plant, the seed thereof, plant propagation material or the soil on which the plants are grown or intended to be grown.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights.
  • Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
  • Plants which can be treated in accordance with the invention include the following plants from the group of the useful plants, ornamentals, turfs, generally used trees which are employed as ornamentals in the public _ _ and domestic sectors, and forestry trees.
  • Forestry trees comprise trees for the production of timber, cellulose, paper and products made from parts of the trees.
  • useful plants refers to crop plants which are employed as plants for obtaining foodstuffs, feedstuffs, fuels or for industrial purposes.
  • the useful plants include for example the following types of plants: turf, vines, cereals, for example wheat, barley, rye, oats, rice, maize and millet/sorghum, corn, maize; beet, for example sugar beet and fodder beet; fruits, for example pome fruit, stone fruit and soft fruit, for example apples, pears, plums, peaches, almonds, cherries and berries, for example strawberries, raspberries, blackberries; legumes, for example beans, lentils, peas and soybeans; oil crops, for example oilseed rape, winter oilseed rape, spring oilseed rap, canola, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cacao and peanuts; cucurbits, for example pumpkin/squash, cucumbers and melons; fibre plants, for example cotton, flax, hemp and jute; citrus fruit, for example oranges, lemons, grapefruit and tangerines; vegetables, for example spinach, lettuce, asparagus, cabbage species
  • the following plants are considered to be particularly suitable target crops: cotton, aubergine, turf, pome fruit, stone fruit, soft fruit, maize, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybeans, oilseed rape, tomato, bell pepper, melons, cabbage, potato and apple.
  • trees are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp..
  • Examples of turf grasses are including cool-season turf grasses and warm-season turf grasses.
  • Cold-season turf grasses are bluegrasses (Poa spp.), such as Kentucky bluegrass (Poa pratensis L.), rough bluegrass (Poa trivialis L.), Canada bluegrass (Poa compressa L.), annual bluegrass (Poa annua L.), upland bluegrass (Poa glaucantha Gaudin), wood bluegrass (Poa nemoralis L.) and bulbous bluegrass (Poa bulbosa L.); bentgrasses (Agrostis spp.) such as creeping bentgrass (Agrostis palustris Huds.), colonial bentgrass (Agrostis tenuis Sibth.), velvet bentgrass (Agrostis canina L.), South German mixed bentgrass (Agrostis spp.
  • ryegrasses such as annual ryegrass (Lolium multiflorum Lara), perennial ryegrass (Lolium perenne L.) and Italian ryegrass (Lolium multiflorum Lam.); and wheatgrasses (Agropyron spp.), such as fairway wheatgrass (Agropyron cristatum (L.) Gaertn.), crested wheatgrass (Agropyron desertorum (Fisch.
  • Warm-season turf grasses are Bermuda grass (Cynodon spp. L. C. Rich), zoysia grass (Zoysia spp. Willd.), St. Augustine grass (Stenotaphrum secundatum Walt Kuntze), centipede grass (Eremochloa ophiuroides Munrohack.), carpetgrass (Axonopus affinis Chase), Bahia grass (Paspalum notatum Flugge), Kikuyu grass (Pennisetum clandestinum Hochst.
  • phytopathogenic microorganisms in particular phytopathogenic fungi which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis; Uromyces species, for example Puccinia
  • Pseudoperonospora humuli or Pseudoperonospora cubensis Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe cirri; Elsinoe species, for example Elsinoe fawcettii; Gloeospor

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Abstract

La présente invention concerne l'utilisation de N-(2-phényléthyle 2-substitué)carboxamides et de N-(2-phényléthyle 2-substitué)thiocarboxamides dans la lutte contre des micro-organismes phytopathogènes en agriculture, les micro-organismes phytopathogènes, leur habitat, la plante, sa semence, le matériau de propagation végétale ou le sol sur lequel les plantes sont cultivées ou doivent être cultivées, étant traités avec les composés selon l'invention en des quantités efficaces.
PCT/EP2015/074864 2014-10-29 2015-10-27 N-(2-phényléhyle 2-substitué)carboxamides et n-(2-phényléhyle 2-substitué)-thiocarboxamides utilisés comme fongicides Ceased WO2016066639A1 (fr)

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CN110642782A (zh) * 2019-10-25 2020-01-03 浙江工业大学 一种(s)-2-(2-氯烟酰氨基)丙基丙酸酯类衍生物及其制备方法和应用

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EP1256569A1 (fr) * 2000-02-16 2002-11-13 Ishihara Sangyo Kaisha, Ltd. Derives de phenacylamine, production de ces derives et agents de lutte contre les ravageurs contenant ces derives
WO2007060166A1 (fr) * 2005-11-22 2007-05-31 Bayer Cropscience Sa Nouveaux derives de n-phenethylcarboxamide
WO2008101976A1 (fr) * 2007-02-22 2008-08-28 Bayer Cropscience Sa Dérivés fongicides de n-(3-phénylpropyl)carboxamide
WO2008148570A1 (fr) * 2007-06-08 2008-12-11 Syngenta Participations Ag Amides d'acide carboxylique de pyrazole utiles comme microbiocides
WO2010012795A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés de n-(2-phénoxyéthyl) carboxamide fongicides et leurs analogues aza, thia et sila
WO2011128989A1 (fr) * 2010-04-14 2011-10-20 アグロカネショウ株式会社 Dérivé de pyrazine-2-carboxamide et fongicides contenant celui-ci en tant que substance active
WO2011151369A1 (fr) * 2010-06-03 2011-12-08 Bayer Cropscience Ag N-[(het)aryléthyl)]pyrazole(thio)carboxamides et leurs analogues hétérosubstitués
WO2014004064A1 (fr) * 2012-06-29 2014-01-03 E. I. Du Pont De Nemours And Company Carboxamides hétérocycliques fongicides

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Publication number Priority date Publication date Assignee Title
EP1256569A1 (fr) * 2000-02-16 2002-11-13 Ishihara Sangyo Kaisha, Ltd. Derives de phenacylamine, production de ces derives et agents de lutte contre les ravageurs contenant ces derives
WO2007060166A1 (fr) * 2005-11-22 2007-05-31 Bayer Cropscience Sa Nouveaux derives de n-phenethylcarboxamide
WO2008101976A1 (fr) * 2007-02-22 2008-08-28 Bayer Cropscience Sa Dérivés fongicides de n-(3-phénylpropyl)carboxamide
WO2008148570A1 (fr) * 2007-06-08 2008-12-11 Syngenta Participations Ag Amides d'acide carboxylique de pyrazole utiles comme microbiocides
WO2010012795A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés de n-(2-phénoxyéthyl) carboxamide fongicides et leurs analogues aza, thia et sila
WO2011128989A1 (fr) * 2010-04-14 2011-10-20 アグロカネショウ株式会社 Dérivé de pyrazine-2-carboxamide et fongicides contenant celui-ci en tant que substance active
WO2011151369A1 (fr) * 2010-06-03 2011-12-08 Bayer Cropscience Ag N-[(het)aryléthyl)]pyrazole(thio)carboxamides et leurs analogues hétérosubstitués
WO2014004064A1 (fr) * 2012-06-29 2014-01-03 E. I. Du Pont De Nemours And Company Carboxamides hétérocycliques fongicides

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110642782A (zh) * 2019-10-25 2020-01-03 浙江工业大学 一种(s)-2-(2-氯烟酰氨基)丙基丙酸酯类衍生物及其制备方法和应用
CN110642782B (zh) * 2019-10-25 2021-04-27 浙江工业大学 一种(s)-2-(2-氯烟酰氨基)丙基丙酸酯类衍生物及其制备方法和应用

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