AR104808A1 - Amidas cíclicas sustituidas como herbicidas - Google Patents

Amidas cíclicas sustituidas como herbicidas

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Publication number
AR104808A1
AR104808A1 ARP160101556A ARP160101556A AR104808A1 AR 104808 A1 AR104808 A1 AR 104808A1 AR P160101556 A ARP160101556 A AR P160101556A AR P160101556 A ARP160101556 A AR P160101556A AR 104808 A1 AR104808 A1 AR 104808A1
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Argentina
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alkyl
ring
independently
haloalkyl
cycloalkyl
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ARP160101556A
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English (en)
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Duncan Satterfield Andrew
James Campbell Matthew
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Du Pont
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Publication of AR104808A1 publication Critical patent/AR104808A1/es

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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • 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
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
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    • 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
    • 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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • 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
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

Se describen, además, composiciones que contienen los compuestos de fórmula (1) y métodos para controlar vegetación no deseada; los métodos comprenden poner la vegetación no deseada o su entorno en contacto con una cantidad eficaz de un compuesto o una composición de la presente. Reivindicación 1: Un compuesto seleccionado de fórmula (1), N-óxidos y sales de estos, en donde: A es una cadena saturada, parcialmente insaturada o completamente insaturada que contiene de 2 a 3 átomos seleccionados de hasta 3 átomos de carbono, hasta 1 átomo de O, hasta 1 átomo de S y hasta 2 átomos de N, en donde hasta 2 miembros de carbono se seleccionan independientemente de C(=O) y C(=S), y el miembro de átomo de azufre se selecciona de S(=O)ᵘ(=NR⁸)ᵛ; esa cadena está sustituida opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R¹⁵ en átomos de carbono y R¹⁶ en átomos de nitrógeno; Q¹ es un anillo fenilo o un sistema de anillo naftalenilo; cada anillo o sistema de anillo está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R⁷; o un anillo heteroaromático de 5 a 6 miembros o un sistema de anillo bicíclico heteroaromático de 8 a 10 miembros; cada anillo o sistema de anillo contiene miembros de anillo seleccionados de átomos de carbono y de 1 a 4 heteroátomos seleccionados independientemente de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros de anillo que son carbono se seleccionan independientemente de C(=O) y C(=S), y los miembros de anillo que son átomos de azufre se seleccionan independientemente de S(=O)ᵘ(=NR⁸)ᵛ; cada anillo o sistema de anillo está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R⁷ en miembros de anillo que son átomos de carbono y seleccionados de R⁹ en miembros de anillo que son átomos de nitrógeno; Q² es un anillo fenilo o un sistema de anillo naftalenilo; cada anillo o sistema de anillo está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R¹⁰; o un anillo heteroaromático de 5 a 6 miembros o un sistema de anillo bicíclico heteroaromático de 8 a 10 miembros; cada anillo o sistema de anillo contiene miembros de anillo seleccionados de átomos de carbono y de 1 a 4 heteroátomos seleccionados independientemente de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros de anillo que son carbono se seleccionan independientemente de C(=O) y C(=S), y los miembros de anillo que son átomos de azufre se seleccionan independientemente de S(=O)ᵘ(=NR⁸)ᵛ; cada anillo o sistema de anillo está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R¹⁰ en miembros de anillo que son átomos de carbono y seleccionados de R¹¹ en miembros de anillo que son átomos de nitrógeno; Y¹ e Y² son, cada uno independientemente, O, S o NR¹²; J es -CR²R³-; o -CR²R³-CR²ᵃR³ᵃ- en donde la entidad -CR²R³- está conectada directamente al N; R¹ es H, hidroxilo, amino, ciano, formilo, alquilcarbonilalquilo C₃₋₈, -C(alquilo C₁₋₄)=N-O(alquilo C₁₋₄), -C(O)NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, cianoalquilo C₂₋₆, cicloalquilo C₃₋₆, cicloalquilalquilo C₄₋₈, alcoxialquilo C₂₋₈, alcoxialcoxialquilo C₃₋₈, haloalcoxialquilo C₂₋₈, haloalquenilalquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, cicloalquilcarbonilalquilo C₅₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminoalquilo C₂₋₈, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, cicloalquiltio C₃₋₈, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfinilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈, trialquilsililo C₃₋₁₀; o arilcarbonilo, arilalquenilalquilo, arilcarbonilalquilo o -CPh=N-O(C₁₋₄ alquilo), cada uno sustituido opcionalmente en miembros de anillo con hasta 5 sustituyentes seleccionados independientemente de R¹³; o G¹; R² y R³ son, cada uno, independientemente, H, halógeno, hidroxilo, alquilo C₁₋₄, haloalquilo C₁₋₄ o alcoxi C₁₋₄; o R² y R³ se consideran en conjunto con el átomo de carbono al cual están unidos para formar un anillo cicloalquilo C₃₋₇; R²ᵃ y R³ᵃ son, cada uno independientemente H, halógeno o alquilo C₁₋₄; o R²ᵃ y R³ᵃ se consideran en conjunto con el átomo de carbono al cual están unidos para formar un anillo cicloalquilo C₃₋₇; cada R⁴ es, independientemente, H, halógeno, hidroxilo, alcoxi C₁₋₄ o alquilo C₁₋₄; cada R⁵ es, independientemente, H, halógeno, hidroxilo, alcoxi C₁₋₄, ciano o alquilo C₁₋₄; R⁶ es H, hidroxilo, amino, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, alcoxialcoxialquilo C₃₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, cicloalquiltio C₃₋₈, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfinilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R⁷ es, independientemente, halógeno, hidroxilo, ciano, nitro, alquilo C₁₋₈, cianoalquilo C₂₋₈, cianoalcoxi C₁₋₈, haloalquilo C₁₋₈, alquenilo C₂₋₈, haloalquenilo C₂₋₈, alquinilo C₂₋₈, haloalquinilo C₂₋₈, nitroalquilo C₁₋₈, nitroalquenilo C₂₋₈, alcoxialquilo C₂₋₈, alcoxialcoxialquilo C₃₋₈, haloalcoxialquilo C₂₋₈, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₁₀, alquilcicloalquilo C₄₋₁₀, alcoxi C₁₋₈, haloalcoxi C₁₋₈, alqueniloxi C₂₋₈, haloalqueniloxi C₂₋₈, alquiniloxi C₃₋₈, haloalquiniloxi C₃₋₈, cicloalcoxi C₃₋₈, alquiltio C₁₋₈, haloalquiltio C₁₋₈, alquilsulfinilo C₁₋₈, haloalquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilsulfonilo C₁₋₈, hidroxilo, formilo, alquilcarbonilo C₂₋₈, alquilcarboniloxi C₂₋₈, alquilsulfoniloxi C₁₋₈, haloalquilsulfoniloxi C₁₋₈, amino, alquilamino C₁₋₄, dialquilamino C₂₋₄, formilamino, alquilcarbonilamino C₂₋₄, -SF₅, -SCN, cicloalquilalcoxi C₄₋₁₀, cicloalquilalquilo C₄₋₁₀, alqueniloxi C₂₋₈, haloalqueniloxi C₂₋₈, alcoxialcoxi C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilsulfoniloxi C₁₋₈, haloalquilsulfoniloxi C₁₋₈, alquiltio C₁₋₈, haloalquiltio C₁₋₈, cicloalquiltio C₃₋₈, alquilsulfinilo C₁₋₈, haloalquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, o haloalquilsulfonilo C₁₋₈, alquinilo C₂₋₈, haloalquinilo C₂₋₈, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, haloalcoxialcoxi C₃₋₈, haloalcoxihaloalquilo C₂₋₈, haloalquilo C₁₋₈, halocicloalquilo C₃₋₈, alquilcarboniloxi C₂₋₈, haloalquilcarboniloxi C₂₋₈, trialquilsililo C₃₋₁₂, trimetilsililmetilo o trimetilsililmetoxi; o G²; o R¹⁷ON=CR¹⁷ᵃ-, (R¹⁸)₂C=NO, (R¹⁹)₂NN=CR¹⁷ᵃ-, (R¹⁸)₂C=NNR²⁰ᵃ-, R²⁰N=CR¹⁷ᵃ-, (R¹⁸)₂C=N-, R¹⁷ON=CR¹⁷ᵃC(R²³ᵇ)₂- o (R¹⁸)₂C=NOC(R²⁴ᵃ)₂-, en donde el enlace doble que se proyecta hacia la derecha indica el punto de conexión a Q¹; o dos R⁷ adyacentes se consideran en conjunto con los átomos de carbono a los cuales están unidos para formar un anillo cicloalquilo C₃₋₇; cada R¹⁰ es, independientemente, halógeno, hidroxilo, ciano, nitro, alquilo C₁₋₈, cianoalquilo C₂₋₈, cianoalcoxi C₁₋₈, haloalquilo C₁₋₃, alquenilo C₂₋₈, haloalquenilo C₂₋₈, alquinilo C₂₋₈, haloalquinilo C₂₋₈, nitroalquilo C₁₋₈, nitroalquenilo C₂₋₈, alcoxialquilo C₂₋₈, alcoxialcoxialquilo C₃₋₈, haloalcoxialquilo C₂₋₈, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₁₀, alquilcicloalquilo C₄₋₁₀, alcoxi C₁₋₈, haloalcoxi C₁₋₈, alqueniloxi C₂₋₈, haloalqueniloxi C₂₋₈, alquiniloxi C₃₋₈, haloalquiniloxi C₃₋₈, cicloalcoxi C₃₋₈, alquiltio C₁₋₈, haloalquiltio C₁₋₈, alquilsulfinilo C₁₋₈, haloalquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilsulfonilo C₁₋₈, hidroxilo, formilo, alquilcarbonilo C₂₋₈, alquilcarboniloxi C₂₋₈, alquilsulfoniloxi C₁₋₈, haloalquilsulfoniloxi C₁₋₈, amino, alquilamino C₁₋₄, dialquilamino C₂₋₄, formilamino, alquilcarbonilamino C₂₋₄, -SF₅, -SCN, cicloalquilalcoxi C₄₋₁₀, cicloalquilalquilo C₄₋₁₀, alqueniloxi C₂₋₈, haloalqueniloxi C₂₋₈, alcoxialcoxi C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilsulfoniloxi C₁₋₈, haloalquilsulfoniloxi C₁₋₈, alquiltio C₁₋₈, haloalquiltio C₁₋₈, cicloalquiltio C₃₋₈, alquilsulfinilo C₁₋₈, haloalquilsulfinilo C₁₋₈, alquilsulfonilo C₁₋₈, haloalquilsulfonilo C₁₋₈, alquinilo C₂₋₈, haloalquinilo C₂₋₈, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, haloalcoxialcoxi C₃₋₈, haloalcoxihaloalquilo C₂₋₈, haloalquilo C₁₋₈, halocicloalquilo C₃₋₈, alquilcarboniloxi C₂₋₈, haloalquilcarboniloxi C₂₋₈, trialquilsililo C₃₋₁₂, trimetilsililmetilo o trimetilsililmetoxi; o G²; o R¹⁷ON=CR¹⁷ᵃ-, (R¹⁸)₂C=NO-, (R¹⁹)₂NN=CR¹⁷ᵃ-, (R¹⁸)₂C=NNR²⁰ᵃ-, R²⁰N=CR¹⁷ᵃ-, (R¹⁸)₂C=N-, R¹⁷ON=CR¹⁷ᵃC(R²³ᵇ)₂- o (R¹⁸)₂C=NOC(R²⁴ᵃ)₂-, en donde el enlace doble que se proyecta hacia la derecha indica el punto de conexión a Q²; o dos R¹⁰ adyacentes se consideran en conjunto con los átomos de carbono a los cuales están unidos para formar un anillo cicloalquilo C₃₋₇; cada R⁸ es, independientemente, H, ciano, alquilcarbonilo C₂₋₃ o haloalquilcarbonilo C₂₋₃; cada R⁹ y R¹¹ es, independientemente, ciano, alquilo C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, cicloalquilo C₃₋₆, alcoxialquilo C₂₋₃, alcoxi C₁₋₃, alquilcarbonilo C₂₋₃, alcoxicarbonilo C₂₋₃, alquilaminoalquilo C₂₋₃ o dialquilaminoalquilo C₃₋₄; cada R¹² es, independientemente, H, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, -(C=O)CH₃ o -(C=O)CF₃; cada G¹ es, independientemente, fenilo, fenilmetilo, piridinilmetilo, fenilcarbonilo, fenoxi, feniletinilo, fenilsulfonilo, fenilcarbonilalquilo, 2-, 3- ó 4-piridiniloxi o un anillo heteroaromático de 5 ó 6 miembros; cada uno está sustituido opcionalmente en los miembros anulares con hasta 5 sustituyentes seleccionados independientemente de R¹³; cada G² es, independientemente, fenilo, fenilmetilo, piridinilmetilo, fenilcarbonilo, fenilcarbonilalquilo, fenoxi, feniletinilo, fenilsulfonilo, 2-, 3- ó 4-piridiniloxi o un anillo heteroaromático de 5 ó 6 miembros; cada uno está sustituido opcionalmente en los miembros anulares con hasta 5 sustituyentes seleccionados independientemente de R¹⁴; cada R¹³ y R¹⁴ es, independientemente, halógeno, ciano, hidroxilo, amino, nitro, CHO, -C(=O)OH, -C(=O)NH₂, -SO₂NH₂, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, alcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, cicloalquilalcoxicarbonilo C₅₋₁₂, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquilcarboniloxilo C₂₋₈, alquiltio C₁₋₆, haloalquiltio C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈, trialquilsililo C₃₋₁₀, alquilamino C₁₋₆, dialquilamino C₂₋₈, alquilcarbonilamino C₂₋₈, alquilsulfonilamino C₁₋₆, fenilo, piridinilo o tienilo; cada R¹⁵ es, independientemente, halógeno, ciano, hidroxilo, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxialquilo C₂₋₄, alquilcarbonilo C₂₋₄, alcoxicarbonilo C₂₋₄, cicloalquilo C₃₋₆ o cicloalquilalquilo C₄₋₈; o dos R¹⁵ adyacentes se consideran en conjunto con el o los átomos de carbono a los cuales están unidos para formar un anillo cicloalquilo C₃₋₇; cada R¹⁶ es, independientemente, ciano, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₄, alquilcarbonilo C₂₋₄, alcoxicarbonilo C₂₋₄ o cicloalquilo C₃₋₆; cada R¹⁷ es, independientemente, H, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfinilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R¹⁷ᵃ es, independientemente, H, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, cicloalquiltio C₃₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R¹⁸ es, independientemente, H, hidroxilo, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsufinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alcoxi C₁₋₆, alquiltio C₁₋₆, haloalquiltio C₁₋₆, cicloalquiltio C₃₋₈, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfinilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R¹⁹ es, independientemente, H, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alcoxi C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R²⁰ es, independientemente, H, hidroxilo, amino, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alquilcarbonilo C₂₋₈, haloalquilcarbonilo C₂₋₈, cicloalquilcarbonilo C₄₋₁₀, alcoxicarbonilo C₂₋₈, haloalcoxicarbonilo C₂₋₈, cicloalcoxicarbonilo C₄₋₁₀, alquilaminocarbonilo C₂₋₈, dialquilaminocarbonilo C₃₋₁₀, cicloalquilaminocarbonilo C₄₋₁₀, alcoxi C₁₋₆, alquilsulfinilo C₁₋₆, haloalquilsulfinilo C₁₋₆, cicloalquilsulfinilo C₃₋₈, alquilsulfonilo C₁₋₆, haloalquilsulfonilo C₁₋₆, cicloalquilsulfonilo C₃₋₈, alquilaminosulfonilo C₁₋₆, dialquilaminosulfonilo C₂₋₈ o trialquilsililo C₃₋₁₀; o G¹; cada R²⁰ᵃ es, independientemente, H, alquilo C₁₋₆, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, alcoxialquilo C₂₋₈, haloalcoxialquilo C₂₋₈, alquiltioalquilo C₂₋₈, alquilsulfinilalquilo C₂₋₈, alquilsulfonilalquilo C₂₋₈, alcoxi C₁₋₆ o trialquilsililo C₃₋₁₀; G o G¹; cada R²³ᵇ es, independientemente, H, halógeno, ciano, hidroxilo, alquilo C₁₋₄, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxialquilo C₂₋₄, alquilcarbonilo C₂₋₄, alcoxicarbonilo C₂₋₄ o cicloalquilo C₃₋₆; cada R²⁴ᵃ es, independientemente, H, alquilo C₁₋₄, cicloalquilo C₃₋₈, cicloalquilalquilo C₄₋₈, haloalquilo C₁₋₄, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alcoxialquilo C₂₋₄, alquilcarbonilo C₂₋₄, alcoxicarbonilo C₂₋₄ o cicloalquilo C₃₋₆; y cada u y v son independientemente 0, 1 ó 2 en cada instancia de S(=O)ᵘ(=NR⁸)ᵛ, siempre que la suma de u y v sea 0, 1 ó 2; siempre que A sea S y Q¹ sea fenilo no sustituido, Q² es distinto del fenilo no sustituido.
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