AR117291A1 - HETEROCYCLIC CYANAMIDE COMPOUNDS WITH PESTICIDE ACTIVITY - Google Patents

HETEROCYCLIC CYANAMIDE COMPOUNDS WITH PESTICIDE ACTIVITY

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AR117291A1
AR117291A1 ARP190103601A ARP190103601A AR117291A1 AR 117291 A1 AR117291 A1 AR 117291A1 AR P190103601 A ARP190103601 A AR P190103601A AR P190103601 A ARP190103601 A AR P190103601A AR 117291 A1 AR117291 A1 AR 117291A1
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Argentina
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alkyl
alkoxy
haloalkyl
cyano
haloalkoxy
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ARP190103601A
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Spanish (es)
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Nicola Compagnone
Andr Stoller
Stefano Rendine
Julien Daniel Henri Gagnepain
Aurelien Bigot
Pierre Joseph Marcel Jung
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Syngenta Crop Protection Ag
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Publication of AR117291A1 publication Critical patent/AR117291A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-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
    • A01N43/72—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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Abstract

Reivindicación 1: Un compuesto de fórmula (1), en donde: A es un enlace directo, O ó S(O)ₚ, en donde p se selecciona entre 0, 1 ó 2; R¹ es alquilo C₁₋₆ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre U¹ o un solo sustituyente seleccionado entre U², o haloalquilo C₁₋₆ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre U¹ o un solo sustituyente seleccionado entre U²; o alquenilo C₂₋₆ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre U¹ o un solo sustituyente seleccionado entre U² o haloalquenilo C₂₋₆; o alquinilo C₂₋₇ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre U¹ o un solo sustituyente seleccionado entre U² o haloalquinilo C₂₋₆; o cicloalquilo C₃₋₆, en donde la fracción cicloalquilo está opcionalmente sustituida con 1 ó 2 sustituyentes seleccionados independientemente entre U³ o un solo sustituyente seleccionado entre U²; o ciano, nitro, halógeno, -C(O)R⁵, -C(O)NR⁶R⁷ o -C(R⁶)=NOR⁶; U¹ es nitro, ciano, amino, hidroxilo, CO₂H, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxi C₁₋₂-alcoxi C₁₋₂, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, alquilcarbonilo C₁₋₄, alcoxicarbonilo C₁₋₄, haloalquilcarbonilo C₁₋₄, haloalcoxicarbonilo C₁₋₄, cicloalquilcarbonilo C₃₋₄, =N-O(alquilo C₁₋₄), =N-O(haloalquilo C₁₋₄), -Si(alquilo C₁₋₄)₃, -OSi(alquilo C₁₋₄)₃, (haloalquil C₁₋₄)NH-, (haloalquil C₁₋₄)₂N-, (haloalquil C₁₋₄)(alquilo C₁₋₄)N-, (alquil C₁₋₄)NH-, (alquil C₁₋₄)₂N-, (cicloalquil C₃₋₆)NH-, (cicloalquil C₃₋₆)(alquilo C₁₋₄)N-, (PhCH₂)NH-, (PhCH₂)(alquil C₁₋₄)N-, alquilcarbonilo C₁₋₄, en donde el grupo alquilo está sustituido opcionalmente con ciano, alcoxicarbonilamino C₁₋₄, haloalquilcarbonilamino C₁₋₄, alquilaminocarbonilo C₁₋₄, cicloalquilaminocarbonilo C₁₋₆, haloalquilaminocarbonilo C₁₋₄, halocicloalquilaminocarbonilo C₃₋₆, -SPh, -OC(O)R⁶, -O-pirazina o -C(O)NH₂; U² es fenilo, heteroarilo, en donde la fracción heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre nitrógeno, oxígeno y azufre, o un anillo heterocíclico saturado o parcialmente saturado de 4 a 6 miembros, en donde el anillo heterocíclico comprende de 1 a 3 heteroátomos seleccionados entre nitrógeno, oxígeno y azufre, y en donde cada anillo de fenilo, heteroarilo o heterocíclico está sustituido opcionalmente con: (i) 1, 2, 3, 4 ó 5 grupos halógenos seleccionados independientemente, o (ii) 1 ó 2 grupos seleccionados independientemente entre U⁴ y, opcionalmente, un grupo halógeno; U³ es halógeno, nitro, ciano, amino, hidroxilo, CO₂H, alquilo C₁₋₄, haloalquilo C₁₋₄, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, halocicloalquil C₃₋₆-alquilo C₁₋₄, cicloalquil C₃₋₆-alquilo C₁₋₄, alcoxi C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, haloalcoxi C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, ciano-alquilo C₁₋₄, ciano-haloalquilo C₁₋₄, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, alquilcarbonilo C₁₋₄, alcoxicarbonilo C₁₋₄, haloalquilcarbonilo C₁₋₄, haloalcoxicarbonilo C₁₋₄ y -C(O)NH₂; U⁴ es nitro, ciano, amino, hidroxilo, -SCN, -CO₂H, alquilo C₁₋₄, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, cicloalquil C₃₋₆-alquilo C₁₋₄, halocicloalquil C₃₋₆-alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, alcoxi C₁₋₄-alcoxi C₁₋₄, ciano-alquilo C₁₋₄, ciano-haloalquilo C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, haloalcoxi C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, alquilcarbonilo C₁₋₄, alcoxicarbonilo C₁₋₄, haloalquilcarbonilo C₁₋₄, haloalcoxicarbonilo C₁₋₄, (alquil C₁₋₄)NH-, (alquil C₁₋₄)₂N-, (cicloalquil C₃₋₆)NH-, (cicloalquil C₃₋₆)₂N-, alquilcarbonilamino C₁₋₄, cicloalquilcarbonilamino C₃₋₄, haloalquilcarbonilamino C₁₋₄, halocicloalquilcarbonilamino C₃₋₆, alquilaminocarbonilo C₁₋₄, cicloalquilaminocarbonilo C₃₋₆, haloalquilaminocarbonilo C₁₋₄, halocicloalquilaminocarbonilo C₃₋₆, cicloalquilcarbonilo C₃₋₆, halocicloalquilcarbonilo C₃₋₆, -SF₅ o -C(O)NH₂; m es 0, 1 ó 2; R² se selecciona independientemente entre halógeno, ciano, amino, hidroxilo, alquilo C₁₋₄, haloalquilo C₁₋₄, haloalcoxi C₁₋₄, alcoxi C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄ y ciclopropilo; R³ᵃ y R³ᵇ se seleccionan independientemente entre hidrógeno, halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄ y ciano; R⁴ se selecciona de uno Y1 a Y4 del grupo de fórmulas (2), en donde n es 0, 1 ó 2; U se selecciona independientemente entre halógeno, ciano, nitro, hidroxilo, amino, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, formilo, ciclopropilo, alquilcarbonilo C₁₋₄ o cicloalquilcarbonilo C₃₋₆; y R⁵ es hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, haloalquilo C₁₋₆, haloalquenilo C₂₋₆, haloalquinilo C₂₋₆, ciano-alquilo C₁₋₆, nitro-alquilo C₁₋₄, alcoxi C₁₋₄-alquilo C₁₋₄, haloalcoxi C₁₋₄-alquilo C₁₋₄, alquilsulfinil C₁₋₄-alquilo C₁₋₄, alquilsulfonil C₁₋₄-alquilo C₁₋₄, haloalquilsulfanil C₁₋₄-alquilo C₁₋₄, haloalquilsulfinil C₁₋₄-alquilo C₁₋₄, haloalquilsulfonil C₁₋₄-alquilo C₁₋₄ y cicloalquil C₃₋₆-alquilo C₁₋₄, o R⁵ es alquilo C₁₋₄ o haloalquilo C₁₋₄ sustituido con fenilo o heteroarilo, en donde la fracción heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre nitrógeno, oxígeno y azufre, y en donde cada anillo fenilo o heteroarilo está sustituido opcionalmente con 1 ó 2 grupos seleccionados independientemente entre halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄ y haloalquilsulfonilo C₁₋₄; R⁵ es alcoxi C₁₋₆ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre ciano, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, cicloalquilo C₃₋₆ y fenilo o heteroarilo, en donde la fracción heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados entre nitrógeno, oxígeno y azufre, y en donde cada anillo de fenilo o heteroarilo está sustituido opcionalmente con 1 ó 2 grupos seleccionados independientemente entre halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄ y haloalquilsulfonilo C₁₋₄, o R⁵ es haloalcoxi C₁₋₆ sustituido opcionalmente con 1 ó 2 sustituyentes seleccionados independientemente entre ciano, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquenilo C₂₋₄, haloalquenilo C₂₋₄, alquinilo C₂₋₄, haloalquinilo C₂₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄, haloalquilsulfonilo C₁₋₄, cicloalquilo C₃₋₆ y fenilo o heteroarilo, en donde la fracción heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre nitrógeno, oxígeno y azufre, y en donde cada anillo de fenilo o heteroarilo está sustituido opcionalmente con 1 ó 2 grupos seleccionados independientemente entre halógeno, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquilsulfanilo C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄, haloalquilsulfanilo C₁₋₄, haloalquilsulfinilo C₁₋₄ y haloalquilsulfonilo C₁₋₄, o R⁵ es cicloalcoxi C₃₋₆; R⁶ es hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆; y R⁷ es alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆ o fenilo, heteroarilo, en donde la fracción heteroarilo es un anillo aromático monocíclico de 5 ó 6 miembros que comprende 1, 2, 3 ó 4 heteroátomos seleccionados individualmente entre nitrógeno, oxígeno y azufre, o un anillo heterocíclico saturado o parcialmente saturado de 5 ó 6 miembros en donde el anillo heterocíclico comprende de 1 a 3 heteroátomos seleccionados entre nitrógeno, oxígeno y azufre, y en donde cada anillo de fenilo, heteroarilo o heterocíclico está sustituido opcionalmente con: (i) 1, 2, 3, 4 ó 5 grupos halógenos seleccionados independientemente, o (ii) 1 ó 2 grupos seleccionados independientemente entre U⁴ y, opcionalmente, un grupo halógeno; o una sal, estereoisómero, enantiómero, tautómero o N-óxido agroquímicamente aceptable de los mismos.Claim 1: A compound of formula (1), wherein: A is a direct bond, O or S (O) ₚ, wherein p is selected from 0, 1 or 2; R¹ is C₁₋₆ alkyl optionally substituted with 1 or 2 substituents independently selected from U¹ or a single substituent selected from U², or C₁₋₆ haloalkyl optionally substituted with 1 or 2 substituents independently selected from U¹ or a single substituent selected from U²; or C₂₋₆ alkenyl optionally substituted with 1 or 2 substituents independently selected from U¹ or a single substituent selected from U² or C₂₋₆ haloalkenyl; or C₂₋₇ alkynyl optionally substituted with 1 or 2 substituents independently selected from U¹ or a single substituent selected from U² or C₂₋₆ haloalkynyl; or C₃₋₆ cycloalkyl, wherein the cycloalkyl moiety is optionally substituted with 1 or 2 substituents independently selected from U³ or a single substituent selected from U²; or cyano, nitro, halogen, -C (O) R⁵, -C (O) NR⁶R⁷ or -C (R⁶) = NOR⁶; U¹ is nitro, cyano, amino, hydroxyl, CO₂H, C₃₋₆ cycloalkyl, C₃₋₆ halocycloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₂ alkoxy-C₁₋₂ alkoxy, C₁₋₄ alkylsulfanyl, C₁₋ alkylsulfinyl ₄, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, C₁₋₄ alkylcarbonyl, C₁₋₄ alkoxycarbonyl, C₁₋₄ haloalkylcarbonyl, C₁₋₄ haloalkoxycarbonyl, C₃₋₄ cycloalkylcarbonyl, = NO ( C₁₋₄ alkyl), = NO (C₁₋₄ haloalkyl), -Si (C₁₋₄ alkyl) ₃, -OSi (C₁₋₄ alkyl) ₃, (C₁₋₄ haloalkyl) NH-, (C₁₋₄ haloalkyl) ₂N-, (C₁₋₄ haloalkyl) (C₁₋₄ alkyl) N-, (C₁₋₄ alkyl) NH-, (C₁₋₄ alkyl) ₂N-, (C₃₋₆ cycloalkyl) NH-, (C₃₋₆ cycloalkyl) ) (C₁₋₄ alkyl) N-, (PhCH₂) NH-, (PhCH₂) (C₁₋₄ alkyl) N-, C₁₋₄ alkylcarbonyl, wherein the alkyl group is optionally substituted with cyano, C₁₋₄ alkoxycarbonylamino, haloalkylcarbonylamino C₁₋₄, C₁₋₄ alkylaminocarbonyl, C₁₋₆ cycloalkylaminocarbonyl, C₁₋₄ haloalkylaminocarbonyl, C₃₋₆ halocycloalkylaminocarbonyl, -SPh, -OC (O) R⁶, -O-pyrazin a or -C (O) NH₂; U² is phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3, or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur, or a saturated or partially saturated heterocyclic ring of 4 to 6 members, wherein the heterocyclic ring comprises 1 to 3 heteroatoms selected from nitrogen, oxygen, and sulfur, and wherein each phenyl, heteroaryl, or heterocyclic ring is optionally substituted with: (i) 1, 2, 3, 4 or 5 independently selected halogen groups, or (ii) 1 or 2 groups independently selected from U⁴ and optionally a halogen group; U³ is halogen, nitro, cyano, amino, hydroxyl, CO₂H, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ halocycloalkyl, C₁₋₄ halocycloalkyl-C₁₋₄ alkyl, C₃₋₆ cycloalkyl-alkyl C₁₋₄, C₁₋₄ alkoxy, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ haloalkoxy, C₁₋₄ haloalkoxy-C₁₋₄ alkyl, cyano-C₁₋₄ alkyl, cyano-C₁₋₄ haloalkyl, C₂ alkenyl ₋₆, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₂₋₆ haloalkynyl, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, C₁ alkylcarbonyl *, C₁₋₄ alkoxycarbonyl, C₁₋₄ haloalkylcarbonyl, C₁₋₄ haloalkoxycarbonyl, and -C (O) NH₂; U⁴ is nitro, cyano, amino, hydroxyl, -SCN, -CO₂H, C₁₋₄ alkyl, C₃₋₆ cycloalkyl, C₃₋₆ halocycloalkyl, C₃₋₆ cycloalkyl-C₁₋₄ alkyl, C₃₋₆ halocycloalkyl-C₁₋₄ alkyl , C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ alkoxy-C₁₋₄ alkoxy, cyano-C₁₋₄ alkyl, cyano-C₁₋₄ haloalkyl, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₁₋₄ haloalkoxy, C₁₋₄ haloalkoxy-C₁₋₄ alkyl, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, C₁₋₄ alkylcarbonyl, C₁₋₄ alkoxycarbonyl, C₁₋₄ haloalkylcarbonyl, C₁₋₄ haloalkoxycarbonyl, (C₁₋₄ alkyl) NH-, (C₁₋₄ alkyl) ₂N-, (cycloalkyl C₃₋₆) NH-, (C₃₋₆ cycloalkyl) ₂N-, C₁₋₄ alkylcarbonylamino, C₃₋₄ cycloalkylcarbonylamino, C₁₋₄ haloalkylcarbonylamino, C₃₋₆ halocycloalkylcarbonylamino, C₁₋₄ alkylaminocarbonyl, C₃₋₆ cycloalkylaminocarbonyl, C₁₋₄ haloalkylaminocarbonyl C₃₋₆, halocycloalkylaminocarbonyl, cycloalkyl C₃₋₆ arbonyl, C₃₋₆ halocycloalkylcarbonyl, -SF₅ or -C (O) NH₂; m is 0, 1 or 2; R² is independently selected from halogen, cyano, amino, hydroxyl, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, C₁₋₄ alkoxy, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂ haloalkynyl ₋₄, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, and cyclopropyl; R³ᵃ and R³ᵇ are independently selected from hydrogen, halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, and cyano; R⁴ is selected from one Y1 to Y4 from the group of formulas (2), where n is 0, 1, or 2; U is independently selected from halogen, cyano, nitro, hydroxyl, amino, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₁₋₄ haloalkoxy-C₁₋₄ alkyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, formyl, cyclopropyl, C₁₋₄ alkylcarbonyl or C₃₋₆ cycloalkylcarbonyl; and R⁵ is hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, C₁₋₆ haloalkyl, C₂₋₆ haloalkenyl, C₂₋₆ haloalkynyl, cyano-C₁₋₆ alkyl, nitro-alkyl C₁₋₄, C₁₋₄ alkoxy-C₁₋₄ alkyl, C₁₋₄ haloalkoxy-C₁₋₄ alkyl, C₁₋₄ alkylsulfinyl-C₁₋₄ alkyl, C₁₋₄ alkylsulfonyl-C₁₋₄ alkyl, C₁₋₄ haloalkylsulfanyl-alkyl C₁₋₄, C₁₋₄ haloalkylsulfinyl-C₁₋₄ alkyl, C₁₋₄ haloalkylsulfonyl-C₁₋₄ alkyl and C₃₋₆ cycloalkyl-C₁₋₄ alkyl, or R⁵ is C₁₋₄ alkyl or C₁₋₄ haloalkyl substituted with phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3, or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur, and wherein each phenyl or heteroaryl ring is optionally substituted with 1 or 2 groups independently selected from halogen, cyano, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, haloal C₁₋₄ kylsulfanyl, C₁₋₄ haloalkylsulfinyl, and C₁₋₄ haloalkylsulfonyl; R⁵ is C₁₋₆ alkoxy optionally substituted with 1 or 2 substituents independently selected from cyano, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₁ alkylsulfanyl ₋₄, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, C₃₋₆ cycloalkyl, and phenyl or heteroaryl, wherein the heteroaryl moiety is a monocyclic aromatic ring of 5 or 6-membered comprising 1, 2, 3 or 4 heteroatoms selected from nitrogen, oxygen and sulfur, and wherein each phenyl or heteroaryl ring is optionally substituted with 1 or 2 groups independently selected from halogen, cyano, C₁₋₄ alkyl, haloalkyl C₁₋₄, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl and C₁₋₄ haloalkylsulfonyl, or R⁵ is C₁₋ haloalkoxy ₆ optionally substituted with 1 or 2 substitutes Independently selected from cyano, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₂₋₄ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₂₋₄ haloalkynyl, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl , C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, C₁₋₄ haloalkylsulfonyl, C₃₋₆ cycloalkyl, and phenyl or heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3, or 4 heteroatoms individually selected from nitrogen, oxygen, and sulfur, and wherein each phenyl or heteroaryl ring is optionally substituted with 1 or 2 groups independently selected from halogen, cyano, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₄ alkoxy, C₁ haloalkoxy ₋₄, C₁₋₄ alkylsulfanyl, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl, C₁₋₄ haloalkylsulfanyl, C₁₋₄ haloalkylsulfinyl, and C₁₋₄ haloalkylsulfonyl, or R⁵ is C₃₋₆ cycloalkoxy; R⁶ is hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy; and R⁷ is C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, or phenyl, heteroaryl, wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring comprising 1, 2, 3 or 4 heteroatoms selected individually from nitrogen, oxygen and sulfur, or a 5- or 6-membered saturated or partially saturated heterocyclic ring wherein the heterocyclic ring comprises 1 to 3 heteroatoms selected from nitrogen, oxygen, and sulfur, and wherein each phenyl ring , heteroaryl or heterocyclic is optionally substituted with: (i) 1, 2, 3, 4 or 5 independently selected halogen groups, or (ii) 1 or 2 groups independently selected from U⁴ and optionally a halogen group; or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

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