AR114331A1 - DERIVATIVES OF 1- (5-SUBSTITUTE IMIDAZOL-1-IL) BUT-3-EN AND THEIR USES AS FUNGICIDES - Google Patents

DERIVATIVES OF 1- (5-SUBSTITUTE IMIDAZOL-1-IL) BUT-3-EN AND THEIR USES AS FUNGICIDES

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AR114331A1
AR114331A1 ARP190100429A ARP190100429A AR114331A1 AR 114331 A1 AR114331 A1 AR 114331A1 AR P190100429 A ARP190100429 A AR P190100429A AR P190100429 A ARP190100429 A AR P190100429A AR 114331 A1 AR114331 A1 AR 114331A1
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Argentina
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alkyl
cycloalkyl
halogen
tri
silyl
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ARP190100429A
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Spanish (es)
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Vincent Thomas
Dominique Loque
Philippe Kennel
Stephane Brunet
Pierre Genix
Pierre Coqueron
- Bernier David Yves
Miller Ricarda Dr
Lamprecht Sybille Dr
Meissner Ruth Dr
Grtz Andreas Dr
Webster Robert Alan Dr
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Bayer Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/68—Halogen atoms

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

Abstract

Reivindicación 1: Compuesto de fórmula (1), donde R¹ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₃₋₈-cicloalquilo, C₃₋₈-cicloalquil-C₁₋₄-alquilo, C₁₋₈-alcoxi, C₁₋₈-alquiltio, C₆₋₁₄-arilo, C₆₋₁₄-aril-C₁₋₄-alquilo, C₆₋₁₄-aril-C₂₋₄-alquenilo o C₆₋₁₄-aril-C₂₋₄-alquinilo; donde los restos alifáticos, excluidos restos cicloalquilo, de R¹ pueden contener 1, 2, 3 o hasta la cantidad máxima posible de grupos Rᵃ idénticos o diferentes que, independientemente uno del otro, se seleccionan de halógeno, CN, nitro, C₁₋₄-alcoxi y C₁₋₄-haloalcoxi; y donde los restos cicloalquilo y/o arilo de R¹ pueden contener 1, 2, 3, 4, 5 o hasta la cantidad máxima posible de grupos Rᵇ idénticos o diferentes que, independientemente uno del otro, se seleccionan de halógeno, CN, nitro, C₁₋₄-alquilo, C₁₋₄-alcoxi, C₁₋₄-haloaquilo y C₁₋₄-haloalcoxi; R² representa hidrógeno, halógeno, ciano o -OR²ᵃ, donde R²ᵃ representa hidrógeno, C₁₋₈-alquilo, -Si(R⁶ᵃ)(R⁶ᵇ)(R⁶ᶜ), -P(O)(OH)₂, -CH₂-O-P(O)(OH)₂, -C(O)-C₁₋₈-alquilo, -C(O)-C₃₋₇-cicloalquilo, -C(O)NH-C₁₋₈-alquilo, -C(O)N-di-C₁₋₈-alquilo, o -C(O)O-C₁₋₈-alquilo, donde el -C(O)-C₁₋₈-alquilo, -C(O)-C₃₋₇-cicloalquilo, -C(O)NH-C₁₋₈-alquilo, -C(O)N-di-C₁₋₈-alquilo y -C(O)O-C₁₋₈-alquilo está insustituido o sustituido por uno o más grupos seleccionados de halógeno y C₁₋₈-alcoxi, donde R⁶ᵃ, R⁶ᵇ, R⁶ᶜ representan, independientemente uno del otro fenilo o C₁₋₈-alquilo; R³ representa halógeno, hidroxilo, ciano, isociano, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, carboxaldehído, hidroxicarbonilo C₂₋₈-alquil, C₁₋₈-haloalquilo, C₁₋₈-cianoalquil, C₁₋₈-alquiloxi, C₁₋₈-haloalquiloxi, tri(C₁₋₈-alquil)sililo, tri(C₁₋₈-alquil)silil-C₁₋₈-alquilo, C₃₋₇-cicloalquilo, C₃₋₇-halocicloalquilo, C₃₋₇-cicloalquenilo, C₃₋₇-halocicloalquenilo, C₄₋₁₀-cicloalquilalquilo, C₄₋₁₀-halocicloalquillalquilo, C₆₋₁₂-cicloalquilcicloalquilo, C₁₋₈-alquil-C₃₋₇-cicloalquilo, C₁₋₈-alcoxi-C₃₋₇-cicloalquilo, tri(C₁₋₈-alquil)silil-C₃₋₇-cicloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₂₋₈-alqueniloxi, C₂₋₈-haloalqueniloxi, C₃₋₈-alquiniloxi, C₃₋₈-haloalquiniloxi, C₁₋₈-alquilamino, C₁₋₈-haloalquilamino, C₁₋₈-cianoalcoxi, C₄₋₈-cicloalquilalcoxi, C₃₋₆-cicloalcoxi, C₁₋₈-alquilsulfanilo, C₁₋₈-haloalquilsulfanilo, C₁₋₈-alquilcarbonilo, C₁₋₈-haloalquilcarbonilo, arilcarbonilo, aril-C₁₋₆-alquilcarbonilo, C₃₋₈-cicloalquilcarbonilo, C₃₋₈-halocicloalquilcarbonilo, carbamoilo, C₁₋₈-alquilcarbamoilo, di-C₁₋₈-alquilcarbamoilo, N-C₁₋₈-alquiloxicarbamoilo, C₁₋₈-alcoxicarbamoilo, N-C₁₋₈-alquil-C₁₋₈-alcoxicarbamoilo, aminotiocarbonilo, C₁₋₈-alcoxicarbonilo, C₁₋₈-haloalcoxicarbonilo, C₃₋₈-cicloalcoxicarbonilo, C₂₋₈-alcoxialquilcarbonilo, C₂₋₈-haloalcoxialquilcarbonilo, C₃₋₁₀-cicloalcoxialquilcarbonilo, C₁₋₈-alquilaminocarbonilo, di-C₁₋₈-alquilaminocarbonilo, C₃₋₈-cicloalquilaminocarbonilo, C₁₋₈-alquilcarboniloxi, C₁₋₈-haloalquilcarboniloxi, C₃₋₈-cicloalquicarboniloxi, C₁₋₈-alquilcarbonilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₈-alquilaminocarboniloxi, di-C₁₋₈-alquilaminocarboniloxi, C₁₋₈-alquiloxicarboniloxi, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₁₋₈-alquilsulfoniloxi, C₁₋₈-haloalquilsulfoniloxi, C₁₋₈-alquilaminosulfamoilo, di-C₁₋₈-alquilaminosulfamoilo, (C₁₋₈-alcoxiimino)-C₁₋₈-alquilo, (C₃₋₇-cicloalcoxiimino)-C₁₋₈-alquilol, hidroxiimino-C₁₋₈-alquilo, (C₁₋₈-alcoxiimino)-C₃₋₇-cicloalquilo, hidroxiimino-C₃₋₇-cicloalquilo, (C₁₋₈-alquilimino)-oxi, (C₁₋₈-alquilimino)-oxi-C₁₋₈-alquilo, (C₃₋₇-cicloalquilimino)-oxi-C₁₋₈-alquil, (C₁₋₆-alquilimino)-oxi-C₃₋₇-cicloalquilo, (C₁₋₈-alqueniloxiimino)-C₁₋₈-alquilo, (C₁₋₈-alquiniloxiimino)-C₁₋₈-alquilo, (benciloxiimino)-C₁₋₈-alquilo, C₁₋₈-alcoxialquilo, C₁₋₈-alquiltioalquilo, C₁₋₈-alcoxialcoxialquilo, C₁₋₈-haloalcoxialquilo, bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, benciloxi, feniloxi, bencilsulfanilo, bencilamino, fenilsulfanilo o fenilamino, donde el bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, benciloxi o feniloxi está sustituido o insustituido por uno o más grupos que se seleccionan de halógeno, hidroxilo, ciano, isociano, amino, sulfanilo, pentafluoro-l⁶-sulfanilo, carboxaldehído, hidroxicarbonilo, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₁₋₈-cianoalquilo, C₁₋₈ alquiloxi, C₁₋₈-haloalquiloxi, tri(C₁₋₈-alquil)sililo, tri(C₁₋₈-alquil)silil-C₁₋₈-alquilo, C₃₋₇-cicloalquilo, C₃₋₇-halocicloalquilo, C₃₋₇-cicloalquenilo, C₃₋₇-halocicloalquenilo, C₄₋₁₀ cicloalquilalquilo, C₄₋₁₀-halocicloalquilalquilo, C₆₋₁₂-cicloalquilcicloalquilo, C₁₋₈-alquil-C₃₋₇-cicloalquilo, C₁₋₈-alcoxi-C₃₋₇-cicloalquilo, tri(C₁₋₈-alquil)silil-C₃₋₇-cicloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₂₋₈-alqueniloxi, C₁₋₈-haloalqueniloxi, C₃₋₈-alquiniloxi, C₃₋₈-haloalquiniloxi, C₁₋₈-alquilamino, C₁₋₈-haloalquilamino, C₁₋₈-cianoalcoxi, C₄₋₈-cicloalquilalcoxi, C₃₋₆-cicloalcoxi, C₁₋₈-alquilsulfanilo, C₁₋₈-haloalquilsulfanilo, C₁₋₈-alquilcarbonilo, C₁₋₈-haloalquilcarbonilo, arilcarbonilo, aril-C₁₋₆-alquilcarbonilo, C₃₋₈-cicloalquilcarbonilo, C₃₋₈-halocicloalquilcarbonilo, C₁₋₈-alquilcarbamoilo, di-C₁₋₈-alquilcarbamoilo, N-C₁₋₈-alquiloxicarbamoilo, C₁₋₈-alcoxicarbamoilo, N-C₁₋₈-alquil-C₁₋₈-alcoxicarbamoilo, aminotiocarbonilo, C₁₋₈-alcoxicarbonilo, C₁₋₈-haloalcoxicarbonilo, C₃₋₈-cicloalcoxicarbonilo, C₂₋₈-alcoxialquilcarbonilo, C₂₋₈-haloalcoxialquilcarbonilo, C₃₋₁₀-cicloalcoxialquilcarbonilo, C₁₋₈-alquilaminocarbonilo, di-C₁₋₈-alquilaminocarbonilo, C₃₋₈-cicloalquilaminocarbonilo, C₁₋₈-alquilcarboniloxi, C₁₋₈-haloalquilcarboniloxi, C₃₋₈-cicloalquilcarboniloxi, C₁₋₈-alquilcarbonilamino, C₁₋₈-haloalquilcarbonilamino, C₁₋₈-alquilaminocarboniloxi, di-C₁₋₈-alquilaminocarboniloxi, C₁₋₈-alquiloxicarboniloxi, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₁₋₈-alquilsulfoniloxi, C₁₋₈-haloalquilsulfoniloxi, C₁₋₈-alquilaminosulfamoilo, di-C₁₋₈-alquilaminosulfamoilo, (C₁₋₈-alcoxiimino)-C₁₋₈-alquilo, (C₃₋₇-cicloalcoxiimino)-C₁₋₈-alquilo, hidroxiimino-C₁₋₈-alquilo, (C₁₋₈-alcoxiimino)-C₃₋₇-cicloalquilo, hidroxiimino-C₃₋₇-cicloalquilo, (C₁₋₈-alquilimino)-oxi, (C₁₋₈-alquilimino)-oxi-C₁₋₈-alquilo, (C₃₋₇-cicloalquilimino)-oxi-C₁₋₈-alquilo, (C₁₋₆-alquilimino)-oxi-C₃₋₇-cicloalquilo, (C₁₋₈-alqueniloxiimino)-C₁₋₈-alquilo, (C₁₋₈-alquiniloxiimino)-C₁₋₈-alquilo, (benciloxiimino)-C₁₋₈-alquilo, C₁₋₈-alcoxialquilo, C₁₋₈-alquiltioalquilo, C₁₋₈-alcoxialcoxialquilo, C₁₋₈-haloalcoxialquilo, bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, benciloxi, feniloxi, bencilsulfanilo, bencilamino, fenilsulfanilo o fenilamino; R⁴ representa hidrógeno, halógeno, C₁₋₈-alquilo, C₁₋₈-haloaquilo, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi, C₁₋₈-alquiltio o C₁₋₈-haloalquiltio; R⁵ representa hidrógeno, halógeno, C₁₋₈-alquilo, C₁₋₈-haloaquilo, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi, C₁₋₈-alquiltio o C₁₋₈-haloalquiltio; y Q representa un ciclo aromático de 6 miembros de fórmula (2), donde U¹ representa CX¹ o N; U² representa CX² o N; U³ representa CX³ o N; U⁴ representa CX⁴ o N; U⁵ representa CX⁵ o N; donde X¹, X², X³, X⁴ y X⁵ independientemente unos de otros representan hidrógeno, halógeno, nitro, ciano, sulfanilo, pentafluoro-l⁶-sulfanilo, C₁₋₈-alquilo, C₁₋₈-haloalquilo con 1 a 5 átomos de halógeno, C₃₋₈-cicloalquilo, C₃₋₈-halocicloalquilo con 1 a 5 átomos de halógeno, C₁₋₈-haloalquil-C₃₋₇-cicloalquilo, C₃₋₇-cicloalquenilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₆₋₁₂-bicicloalquilo, C₃₋₈-cicloalquil-C₂₋₈-alquenilo, C₃₋₈-cicloalquil-C₂₋₈-alquinilo, C₁₋₈-alcoxi, C₁₋₈-haloalcoxi con 1 a 5 átomos de halógeno, C₁₋₈-alcoxicarbonilo, C₁₋₈-haloalcoxicarbonilo, C₁₋₈-alquilsulfenilo, C₂₋₈-alqueniloxi, C₃₋₈-alquiniloxi, C₃₋₆-cicloalcoxi, C₁₋₈-alquilsulfinilo, C₁₋₈-alquilsulfonilo, tri(C₁₋₈-alquil)-sililoxi, tri(C₁₋₈-alquil)-sililo, tri(C₁₋₈-alquil)-silil-C₂₋₈-alquinilo, tri(C₁₋₈-alquil)-silil-C₂₋₈-alquiniloxi, C₆₋₁₄-arilo, C₆₋₁₄-ariloxi, C₆₋₁₄-arilsulfenilo, heteroarilo de 5 ó 6 miembros o heteroariloxi de 5 ó 6 miembros, donde el C₆₋₁₄-arilo, C₆₋₁₄-ariloxi, C₆₋₁₄-arilsulfenilo, heteroarilo de 5 ó 6 miembros, heteroariloxi de 5 ó 6 miembros está sustituido o insustituidos por uno o más grupos que se seleccionan de halógeno, cianosulfanilo, pentafluoro-l⁶-sulfanilo, C₁₋₈-alquilo, C₁₋₈-haloalquilo, C₁₋₈-cianoalquilo, C₁₋₈-alquiloxi, C₁₋₈-haloalquiloxi, tri(C₁₋₈-alquil)sililo, tri(C₁₋₈-alquil)silil-C₁₋₈-alquilo, C₃₋₇-cicloalquilo, C₃₋₇-halocicloalquilo, C₃₋₇-cicloalquenilo, C₃₋₇-halocicloalquenilo, C₄₋₁₀-cicloalquinilo, C₄₋₁₀-halocicloalquinilo, C₆₋₁₂-cicloalquilcicloalquilo, C₁₋₈-alquil-C₃₋₇-cicloalquilo, C₁₋₈-alcoxi-C₃₋₇-cicloalquilo, tri(C₁₋₈-alquil)silil-C₃₋₇-cicloalquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₂₋₈-alqueniloxi, C₂₋₈-haloalqueniloxi, C₃₋₈-alquiniloxi, C₃₋₈-haloalquiniloxi, C₁₋₈-cianoalcoxi, C₄₋₈-cicloalquilalcoxi, C₃₋₆-cicloalcoxi, C₁₋₈-alquilsulfanilo, C₁₋₈-haloalquilsulfanilo, C₁₋₈-alquilsulfinilo, C₁₋₈-haloalquilsulfinilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, C₁₋₈-alquilsulfoniloxi, C₁₋₈-haloalquilsulfoniloxi, C₁₋₈-alcoxialquilo, C₁₋₈-alquiltioalquilo, C₁₋₈-alcoxialcoxialquilo, C₁₋₈-haloalcoxialquilo, bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, heteroariloxi de 6 miembros, benciloxi, feniloxi, bencilsulfanilo y fenilsulfanilo, donde el bencilo, fenilo, heteroarilo de 5 miembros, heteroarilo de 6 miembros, heteroariloxi de 6 miembros, benciloxi, feniloxi, bencilsulfanilo y fenilsulfanilo están insustituidos o sustituidos por uno o más grupos que se seleccionan de halógeno, CN, nitro, C₁₋₈-alquilo, C₁₋₄-haloalquilo, C₁₋₄-alcoxi, C₁₋₄-haloalcoxi y pentafluoro-l⁶-sulfanilo; y donde como mucho dos de U¹, U², U³, U⁴ y U⁵ representan N; o U¹ y U² o U² y U³ o U³ y U⁴ forman juntos un anillo insustituidos o sustituido de C₁₋₈-alquilo o halógeno de 4 a 6 miembros saturado o insaturado adicional; y sus sales y N-óxidos.Claim 1: Compound of formula (1), where R¹ represents hydrogen, C₁₋₈-alkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₃₋₈-cycloalkyl, C₃₋₈-cycloalkyl-C₁₋₄-alkyl , C₁₋₈-alkoxy, C₁₋₈-alkylthio, C₆₋₁₄-aryl, C₆₋₁₄-aryl-C₁₋₄-alkyl, C₆₋₁₄-aryl-C₂₋₄-alkenyl or C₆₋₁₄-aryl-C₂ ₋₄-alkynyl; where aliphatic moieties, excluding cycloalkyl moieties, of R¹ may contain 1, 2, 3 or up to the maximum possible amount of identical or different Rᵃ groups which, independently of each other, are selected from halogen, CN, nitro, C₁₋₄- alkoxy and C₁₋₄-haloalkoxy; and where the cycloalkyl and / or aryl moieties of R¹ can contain 1, 2, 3, 4, 5 or up to the maximum possible amount of identical or different Rᵇ groups that, independently of each other, are selected from halogen, CN, nitro, C₁₋₄-alkyl, C₁₋₄-alkoxy, C₁₋₄-haloakyl and C₁₋₄-haloalkoxy; R² represents hydrogen, halogen, cyano or -OR²ᵃ, where R²ᵃ represents hydrogen, C₁₋₈-alkyl, -Si (R⁶ᵃ) (R⁶ᵇ) (R⁶ᶜ), -P (O) (OH) ₂, -CH₂-OP (O ) (OH) ₂, -C (O) -C₁₋₈-alkyl, -C (O) -C₃₋₇-cycloalkyl, -C (O) NH-C₁₋₈-alkyl, -C (O) N- di-C₁₋₈-alkyl, or -C (O) O-C₁₋₈-alkyl, where -C (O) -C₁₋₈-alkyl, -C (O) -C₃₋₇-cycloalkyl, -C (O) NH-C₁₋₈-alkyl, -C (O) N-di-C₁₋₈-alkyl and -C (O) O-C₁₋₈-alkyl is unsubstituted or substituted by one or more groups selected from halogen and C₁₋₈-alkoxy, where R⁶ᵃ, R⁶ᵇ, R⁶ᶜ represent, independently of each other, phenyl or C₁₋₈-alkyl; R³ represents halogen, hydroxyl, cyano, isocyan, amino, sulfanyl, pentafluoro-l⁶-sulfanyl, carboxaldehyde, C₂₋₈-alkyl hydroxycarbonyl, C₁₋₈-haloalkyl, C₁₋₈-cyanoalkyl, C₁₋₈-alkyloxy, C₁₋₈ -haloalkyloxy, tri (C₁₋₈-alkyl) silyl, tri (C₁₋₈-alkyl) silyl-C₁₋₈-alkyl, C₃₋₇-cycloalkyl, C₃₋₇-halocycloalkyl, C₃₋₇-cycloalkenyl, C₃₋₇ -halocycloalkenyl, C₄₋₁₀-cycloalkylalkyl, C₄₋₁₀-halocycloalkylalkyl, C₆₋₁₂-cycloalkylcycloalkyl, C₁₋₈-alkyl-C₃₋₇-cycloalkyl, C₁₋₈-alkoxy-C₃₋₇-cycloalkyl, tri (C₁₋₈ -alkyl) silyl-C₃₋₇-cycloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₂₋₈-alkenyloxy, C₂₋₈-haloalkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-haloalkynyloxy, C₁₋₈ -alkylamino, C₁₋₈-haloalkylamino, C₁₋₈-cyanoalkoxy, C₄₋₈-cycloalkylalkoxy, C₃₋₆-cycloalkoxy, C₁₋₈-alkylsulfanyl, C₁₋₈-haloalkylsulfanyl, C₁₋₈-alkylcarbonyl, C₁₋₈-haloalkylcarbonyl , arylcarbonyl, aryl-C₁₋₆-alkylcarbonyl, C₃₋₈-cycloalkylcarbonyl, C₃₋₈-halocycloalkylcarbonyl, carbamoyl, C₁₋₈-alkylcarbamoyl, di-C ₁₋₈-alkylcarbamoyl, N-C₁₋₈-alkyloxycarbamoyl, C₁₋₈-alkoxycarbamoyl, N-C₁₋₈-alkyl-C₁₋₈-alkoxycarbamoyl, aminothiocarbonyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxycarbonyl, C₃₋ ₈-cycloalkoxycarbonyl, C₂₋₈-alkoxyalkylcarbonyl, C₂₋₈-haloalkoxyalkylcarbonyl, C₃₋₁₀-cycloalkoxyalkylcarbonyl, C₁₋₈-alkylaminocarbonyl, di-C₁₋₈-alkylaminocarbonyl, C₃₋₈-cycloalkylaminocarbonyl, C₁₋₈-alkylcarbonyloxy, C₁₋ ₈-haloalkylcarbonyloxy, C₃₋₈-cycloalkycarbonyloxy, C₁₋₈-alkylcarbonylamino, C₁₋₈-haloalkylcarbonylamino, C₁₋₈-alkylaminocarbonyloxy, di-C₁₋₈-alkylaminocarbonyloxy, C₁₋₈-alkyloxycarbonyloxy, C₁₋₈-alkylsulfinyl, C₁₋ ₈-haloalkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₁₋₈-alkylsulfonyloxy, C₁₋₈-haloalkylsulfonyloxy, C₁₋₈-alkylaminosulfamoyl, di-C₁₋₈-alkylaminosulfamoyl, (C₁₋₈-alkoxyimino) - C₁₋₈-alkyl, (C₃₋₇-cycloalkoxyimino) -C₁₋₈-alkylol, hydroxyimino-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino) -C₃₋₇-cycloalkyl, hydroxyimino-C₃₋₇-cycloalkyl, (C₁₋₈-alkyl mino) -oxy, (C₁₋₈-alkylimino) -oxy-C₁₋₈-alkyl, (C₃₋₇-cycloalkylimino) -oxy-C₁₋₈-alkyl, (C₁₋₆-alkylimino) -oxy-C₃₋₇ -cycloalkyl, (C₁₋₈-alkenyloxyimino) -C₁₋₈-alkyl, (C₁₋₈-alkynyloxyimino) -C₁₋₈-alkyl, (benzyloxyimino) -C₁₋₈-alkyl, C₁₋₈-alkoxyalkyl, C₁₋₈ -alkylthioalkyl, C₁₋₈-alkoxyalkoxyalkyl, C₁₋₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino, phenylsulfanyl, or phenylamino, where benzyl, phenyl, heteroaryl of member, 6-membered heteroaryl, benzyloxy, or phenyloxy is substituted or unsubstituted by one or more groups selected from halogen, hydroxyl, cyano, isocyan, amino, sulfanyl, pentafluoro-l⁶-sulfanyl, carboxaldehyde, hydroxycarbonyl, C₁₋₈-alkyl , C₁₋₈-haloalkyl, C₁₋₈-cyanoalkyl, C₁₋₈ alkyloxy, C₁₋₈-haloalkyloxy, tri (C₁₋₈-alkyl) silyl, tri (C₁₋₈-alkyl) silyl-C₁₋₈-alkyl, C₃₋₇-cycloalkyl, C₃₋₇-halocycloalkyl, C₃₋₇-cycloalkenyl, C₃₋₇-halocycloalk uenyl, C₄₋₁₀ cycloalkylalkyl, C₄₋₁₀-halocycloalkylalkyl, C₆₋₁₂-cycloalkylcycloalkyl, C₁₋₈-alkyl-C₃₋₇-cycloalkyl, C₁₋₈-alkoxy-C₃₋₇-cycloalkyl, tri (C₁₋₈-alkyl ) silyl-C₃₋₇-cycloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₂₋₈-alkenyloxy, C₁₋₈-haloalkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-haloalkynyloxy, C₁₋₈-alkylamino , C₁₋₈-haloalkylamino, C₁₋₈-cyanoalkoxy, C₄₋₈-cycloalkylalkoxy, C₃₋₆-cycloalkoxy, C₁₋₈-alkylsulfanyl, C₁₋₈-haloalkylsulfanyl, C₁₋₈-alkylcarbonyl, C₁₋₈-haloalkylcarbonyl, arylcarbonyl , aryl-C₁₋₆-alkylcarbonyl, C₃₋₈-cycloalkylcarbonyl, C₃₋₈-halocycloalkylcarbonyl, C₁₋₈-alkylcarbamoyl, di-C₁₋₈-alkylcarbamoyl, N-C₁₋₈-alkyloxycarbamoyl, C₁₋₈-alkoxycarbamoyl, N -C₁₋₈-alkyl-C₁₋₈-alkoxycarbamoyl, aminothiocarbonyl, C₁₋₈-alkoxycarbonyl, C₁₋₈-haloalkoxycarbonyl, C₃₋₈-cycloalkoxycarbonyl, C₂₋₈-alkoxyalkylcarbonyl, C₂₋₈-haloalkoxyalkylcarbonyl, C₃₋₁₀-cycloalkoxyalkylcarbonyl , C₁₋₈-alkylaminocarbonyl, di-C₁₋₈-alkylaminocarbonyl, C₃₋₈-cycloal kylaminocarbonyl, C₁₋₈-alkylcarbonyloxy, C₁₋₈-haloalkylcarbonyloxy, C₃₋₈-cycloalkylcarbonyloxy, C₁₋₈-alkylcarbonylamino, C₁₋₈-haloalkylcarbonylamino, C₁₋₈-alkylaminocarbonyloxy, di-C₁₋₈-alkylaminocarbonyloxy, C₁₋₈- alkyloxycarbonyloxy, C₁₋₈-alkylsulfinyl, C₁₋₈-haloalkylsulfinyl, C₁₋₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₁₋₈-alkylsulfonyloxy, C₁₋₈-haloalkylsulfonyloxy, C₁₋₈-alkylaminosulfamoyl, di-C₁₋₈- alkylaminosulfamoyl, (C₁₋₈-alkoxyimino) -C₁₋₈-alkyl, (C₃₋₇-cycloalkoxyimino) -C₁₋₈-alkyl, hydroxyimino-C₁₋₈-alkyl, (C₁₋₈-alkoxyimino) -C₃₋₇- cycloalkyl, hydroxyimino-C₃₋₇-cycloalkyl, (C₁₋₈-alkylimino) -oxy, (C₁₋₈-alkylimino) -oxy-C₁₋₈-alkyl, (C₃₋₇-cycloalkylimino) -oxy-C₁₋₈- alkyl, (C₁₋₆-alkylimino) -oxy-C₃₋₇-cycloalkyl, (C₁₋₈-alkenyloxyimino) -C₁₋₈-alkyl, (C₁₋₈-alkynyloxyimino) -C₁₋₈-alkyl, (benzyloxyimino) - C₁₋₈-alkyl, C₁₋₈-alkoxyalkyl, C₁₋₈-alkylthioalkyl, C₁₋₈-alkoxyalkoxyalkyl, C₁₋₈-haloalkoxyalkyl, benzyl, phenyl, 5m heteroaryl members, 6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino, phenylsulfanyl, or phenylamino; R⁴ represents hydrogen, halogen, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-alkoxy, C₁₋₈-haloalkoxy, C₁₋₈-alkylthio or C₁₋₈-haloalkylthio; R⁵ represents hydrogen, halogen, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-alkoxy, C₁₋₈-haloalkoxy, C₁₋₈-alkylthio or C₁₋₈-haloalkylthio; and Q represents a 6-membered aromatic ring of formula (2), where U¹ represents CX¹ or N; U² represents CX² or N; U³ represents CX³ or N; U⁴ represents CX⁴ or N; U⁵ represents CX⁵ or N; where X¹, X², X³, X⁴ and X⁵ independently of each other represent hydrogen, halogen, nitro, cyano, sulfanyl, pentafluoro-l⁶-sulfanyl, C₁₋₈-alkyl, C₁₋₈-haloalkyl with 1 to 5 halogen atoms, C₃₋₈-cycloalkyl, C₃₋₈-halocycloalkyl with 1 to 5 halogen atoms, C₁₋₈-haloalkyl-C₃₋₇-cycloalkyl, C₃₋₇-cycloalkenyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₆ ₋₁₂-bicycloalkyl, C₃₋₈-cycloalkyl-C₂₋₈-alkenyl, C₃₋₈-cycloalkyl-C₂₋₈-alkynyl, C₁₋₈-alkoxy, C₁₋₈-haloalkoxy with 1 to 5 halogen atoms, C₁₋ ₈-alkoxycarbonyl, C₁₋₈-haloalkoxycarbonyl, C₁₋₈-alkylsulfenyl, C₂₋₈-alkenyloxy, C₃₋₈-alkynyloxy, C₃₋₆-cycloalkoxy, C₁₋₈-alkylsulfinyl, C₁₋₈-alkylsulfonyl, tri (C₁₋ ₈-alkyl) -silyloxy, tri (C₁₋₈-alkyl) -silyl, tri (C₁₋₈-alkyl) -silyl-C₂₋₈-alkynyl, tri (C₁₋₈-alkyl) -silyl-C₂₋₈- alkynyloxy, C₆₋₁₄-aryl, C₆₋₁₄-aryloxy, C₆₋₁₄-arylsulfenyl, 5- or 6-membered heteroaryl or 5- or 6-membered heteroaryloxy, where the C₆₋₁₄-aryl, C₆₋₁₄-aryloxy, C₆₋ ₁₄-arylsulfenyl, heteroaryl of 5 or 6-membered, 5- or 6-membered heteroaryloxy is substituted or unsubstituted by one or more groups selected from halogen, cyanosulfanyl, pentafluoro-l⁶-sulfanyl, C₁₋₈-alkyl, C₁₋₈-haloalkyl, C₁₋₈-cyanoalkyl, C₁₋₈-alkyloxy, C₁₋₈-haloalkyloxy, tri (C₁₋₈-alkyl) silyl, tri (C₁₋₈-alkyl) silyl-C₁₋₈-alkyl, C₃₋₇-cycloalkyl, C₃₋₇-halocycloalkyl, C₃₋₇-cycloalkenyl, C₃₋₇-halocycloalkenyl, C₄₋₁₀-cycloalkynyl, C₄₋₁₀-halocycloalkynyl, C₆₋₁₂-cycloalkylcycloalkyl, C₁₋₈-alkyl-C₃₋₇-cycloalkyl, C₁₋₈-C₃₋-alkoxy ₇-cycloalkyl, tri (C₁₋₈-alkyl) silyl-C₃₋₇-cycloalkyl, C₂₋₈-alkenyl, C₂₋₈-alkynyl, C₂₋₈-alkenyloxy, C₂₋₈-haloalkenyloxy, C₃₋₈-alkynyloxy, C₃₋₈-haloalkynyloxy, C₁₋₈-cyanoalkoxy, C₄₋₈-cycloalkylsulfinyl, C₃₋₆-cycloalkoxy, C₁₋₈-alkylsulfanyl, C₁₋₈-haloalkylsulfanyl, C₁₋₈-alkylsulfinyl, C₁₋₈-haloalkylsulfinyl, C₁₋ ₈-alkylsulfonyl, C₁₋₈-haloalkylsulfonyl, C₁₋₈-alkylsulfonyloxy, C₁₋₈-haloalkylsulfonyloxy, C₁₋₈-alkoxyalkyl, C₁₋₈-alkylthioalkyl, C₁₋₈-alkoxyalkoxyalkyl, C₁₋₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl and phenylsulfanyl, where benzyl, phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy, phenyloxy, benzylsulfanyl, and phenylsulfanyl are unsubstituted or substituted by one or more groups selected from halogen, CN, nitro, C₁₋₈-alkyl, C₁₋₄-haloalkyl, C₁₋ ₄-alkoxy, C₁₋₄-haloalkoxy and pentafluoro-l⁶-sulfanyl; and where at most two of U¹, U², U³, U⁴ and U⁵ represent N; or U¹ and U² or U² and U³ or U³ and U⁴ together form an unsubstituted or substituted C₁₋₈-alkyl or additional saturated or unsaturated 4 to 6-membered halogen ring; and its salts and N-oxides.

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