AR119510A1 - HERBICIDE COMPOUNDS - Google Patents

HERBICIDE COMPOUNDS

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AR119510A1
AR119510A1 ARP200102120A ARP200102120A AR119510A1 AR 119510 A1 AR119510 A1 AR 119510A1 AR P200102120 A ARP200102120 A AR P200102120A AR P200102120 A ARP200102120 A AR P200102120A AR 119510 A1 AR119510 A1 AR 119510A1
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Argentina
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alkyl
alkoxy
group
hydrogen
haloalkyl
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ARP200102120A
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Spanish (es)
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Alan Joseph Hennessy
Elizabeth Pearl Jones
Suzanna Jane Dale
Alexander William Gregory
Ian Thomas Tinmouth Houlsby
Yunas Bhonoah
Julia Comas-Barcelo
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Syngenta Crop Protection Ag
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Publication of AR119510A1 publication Critical patent/AR119510A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/12—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • 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
    • A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-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
    • 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
    • A01N47/08—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 one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • 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
    • 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
    • C07D401/10—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 aromatic rings

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

Abstract

Reivindicación 1: Un compuesto de fórmula (1) donde R¹ se selecciona de metilo, etinilo, 1-propinilo, fenilo y un heteroarilo de 5 ó 6 miembros que comprende uno o dos heteroátomos de nitrógeno, estando dicho fenilo y heteroarilo opcionalmente sustituidos con uno o dos sustituyentes R¹⁵; R² se selecciona del grupo constituido por metilo, etilo, metoxi y cloro; R³ se selecciona del grupo constituido por metilo, etilo, metoxi y cloro; R⁴ se selecciona del grupo que consiste en alquilo C₁₋₄, alcoxilo C₁₋₄, haloalquilo C₁₋₄, -C(=O)alquilo C₁₋₄, -C(=O)haloalquilo C₁₋₄, -S(O)ₙ-alquilo C₁₋₆, -S(O)ₙ-haloalquilo C₁₋₆, -S(O)ₙ-(CH₂)ₙ-cicloalquilo C₃₋₆, -S(O)ₙC(R¹¹)R¹²R¹³, -C(O)H, -C(O)-(CH₂)ₙ-cicloalquilo C₃₋₆, -C(O)C(R¹¹)R¹²R¹³, -C(O)alquenilo C₂₋₄, -C(O)(CR⁹R¹⁰)CN, -C(O)(CR⁹R¹⁰)(CR⁹R¹⁰)CN, -C(O)CH₂C(O)-alquilo C₁₋₆, - C(O)CH₂OC(O)-alquilo C₁₋₆, -C(O)O-alquilo C₁₋₆, -C(O)O-haloalquilo C₁₋₆, -C(O)(CH₂)ₙS(O)ₙ-alquilo C₁₋₆, -C(O)-alcoxi C₁₋₃-alquilo C₁₋₆, -C(O)alcoxi C₁₋₃-alquenilo C₂₋₆, -C(O)alcoxi C₁₋₃-alquinilo C₂₋₆, -C(O)alcoxi C₁₋₃- haloalquilo C₁₋₆, -C(O)alcoxi C₁₋₃-cicloalquilo C₃₋₆, -C(O)O-alcoxi C₁₋₃-alquilo C₁₋₆, -C(O)alcoxi C₁₋₃-alcoxi C₁₋₃-alquilo C₁₋₆, -C(O)(CH₂)ₙNR⁵R⁶, -C(O)-(CH₂)ₙ-NR⁷C(O)R⁸, -C(O)-(CH₂)ₙ-O-N=CR⁵R⁵, -CN, -S(O)₂NR¹⁶R¹⁷, -S(O)(=NR¹⁸)R¹⁹, -C(O)C(O)R²⁰, -C(O)C(R²³)=N-O-R²⁴ o -C(O)C(R²³)=N-NR²⁵R²⁶, -(CH₂)ₙ-fenilo, -C(O)-(CH₂)ₙ-fenilo, -S(O)ₙ-(CH₂)ₙ-fenilo, -heterociclilo, -C(O)-(CH₂)ₙ-heterociclilo, -C(O)(CH₂)ₙO-(CH₂)ₙ-heterociclilo, -S(O)ₙ-(CH₂)ₙ-heterociclilo, donde cada heterociclilo es un heterociclilo de 5 ó 6 miembros que puede ser aromático, estar saturado o parcialmente saturado y puede contener de 1 a 4 heteroátomos, cada uno seleccionado independientemente del grupo que consiste en oxígeno, nitrógeno y azufre, y donde dichos grupos heterociclilo o fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxilo C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R⁵ se selecciona del grupo constituido por hidrógeno y alquilo C₁₋₆; R⁶ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, hidroxil-, alcoxi C₁₋₆, cicloalquilo C₃₋₆, -(alcoxi C₁₋₄)(alquilo C₁₋₆), -(alcoxi C₁₋₃)(haloalquilo C₁₋₆), -(CR⁹R¹⁰)(haloalquilo C₁₋₆), -(CR⁹R¹⁰)C(O)NR⁵R⁵, fenilo, -piridilo, donde el fenilo y el piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; o R⁵ y R⁶ conjuntamente forman -CH₂CH₂OCH₂CH₂-; y R⁷ se selecciona del grupo constituido por hidrógeno y alquilo C₁₋₆; R⁸ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, fenilo, -piridilo, donde el fenilo y piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R⁹ es hidrógeno o metilo; R¹⁰ es hidrógeno o metilo; o R⁹ y R¹⁰ conjuntamente forman -CH₂CH₂-; y R¹¹ es hidrógeno o metilo; R¹² se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, hidroxilo y (alcoxi C₁₋₆)-; R¹³ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, hidroxilo y alcoxi C₁₋₆; o R¹² y R¹³ juntos forman -CH₂-X-CH₂-; y X se selecciona del grupo que consiste en O, S y N-R¹⁴; R¹⁴ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₃ y alcoxi C₁₋₃-; R¹⁵ se selecciona independientemente del grupo constituido por alquilo C₁₋₄, haloalquilo C₁₋₄, ciano y halógeno; R¹⁶ es hidrógeno o alquilo C₁₋₆; y R¹⁷ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆, (alcoxi C₁₋₆)-(alquil C₁₋₃)-,-C(O)(alquilo C₁₋₆), -C(O)O(alquilo C₁₋₆) y CH₂CN; o R¹⁶ y R¹⁷ juntos forman -CH₂CH₂OCH₂CH₂-, -CH₂CH₂S(O)₂CH₂CH₂-; R¹⁸ es hidrógeno o alquilo C₁₋₆; R¹⁹ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, fenilo, -piridilo, donde el fenilo y piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²⁰ se selecciona del grupo constituido por alquilo C₁₋₆, haloalquilo C₁₋₆, (alcoxi C₁₋₆)-, haloalcoxi C₁₋₆, -NR²¹R²², fenilo y -piridilo, donde el fenilo y piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²¹ se selecciona del grupo constituido por hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, (alcoxi C₁₋₆)(alquil C₁₋₃)-, cicloalquilo C₃₋₆, (haloalquil C₁₋₆)- y (haloalcoxi C₁₋₆)-, -C(O)(alquilo C₁₋₆), fenilo, -piridilo, donde el fenilo y piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²² es hidrógeno o alquilo C₁₋₆; o R²¹ y R²² juntos forman -CH₂CH₂OCH₂CH₂-; R²³ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxilo C₁₋₆ y haloalcoxilo C₁₋₆; R²⁴ se selecciona del grupo constituido por hidrógeno, alquiloC₁₋₆, (alcoxi C₁₋₆)(alquil C₁₋₃)-, cicloalquilo C₃₋₆, -CH₂CN, tetrahidropiranil-, fenilo y -piridilo, donde el fenilo y piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²⁵ es hidrógeno o alquilo C₁₋₆; R²⁶ es hidrógeno o alquilo C₁₋₆; G se selecciona entre el grupo que consiste en hidrógeno, -(CH₂)ₙ-Rᵃ, -C(O)-Rᵃ, -C(O)-(CRᶜRᵈ)ₙ-O-Rᵇ, -C(O)NRᵃRᵃ, -S(O)₂-Rᵃ y alcoxi C₁₋₈-alquilo C₁₋₃-; Rᵃ se selecciona independientemente del grupo constituido por hidrógeno, alquilo C₁₋₈, haloalquilo C₁₋₃, alquenilo C₂₋₈, alquinilo C₂₋₈, cicloalquilo C₃₋₆, heterociclilo y fenilo, donde dichos grupos heterociclilo y fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; Rᵇ se selecciona del grupo constituido por alquilo C₁₋₈, haloalquilo C₁₋₃, alquenilo C₂₋₈, alquinilo C₂₋₈, cicloalquilo C₃₋₆, heterociclilo y fenilo, donde dichos grupos heterociclilo y fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo constituido por alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; Rᶜ es hidrógeno o alquilo C₁₋₃; Rᵈ es hidrógeno o alquilo C₁₋₃; y n es independientemente 0, 1 ó 2; o una sal aceptable en agricultura de este.Claim 1: A compound of formula (1) wherein R¹ is selected from methyl, ethynyl, 1-propynyl, phenyl and a 5- or 6-membered heteroaryl comprising one or two nitrogen heteroatoms, said phenyl and heteroaryl being optionally substituted with one or two R¹⁵ substituents; R² is selected from the group consisting of methyl, ethyl, methoxy, and chlorine; R³ is selected from the group consisting of methyl, ethyl, methoxy, and chlorine; R⁴ is selected from the group consisting of C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, -C(=O)C₁₋₄ alkyl, -C(=O)C₁₋₄ haloalkyl, -S(O) ₙ-C₁₋₆-alkyl, -S(O)ₙ-C₁₋₆-haloalkyl, -S(O)ₙ-(CH₂)ₙ-C₃₋₆-cycloalkyl, -S(O)ₙC(R¹¹)R¹²R¹³, -C( O)H, -C(O)-(CH₂)ₙ-C₃₋₆-cycloalkyl, -C(O)C(R¹¹)R¹²R¹³, -C(O)C₂₋₄ alkenyl, -C(O)(CR⁹R¹⁰)CN , -C(O)(CR⁹R¹⁰)(CR⁹R¹⁰)CN, -C(O)CH₂C(O)-C₁₋₆ alkyl, -C(O)CH₂OC(O)-C₁₋₆ alkyl, -C(O)O -C₁₋₆-alkyl, -C(O)O-C₁₋₆-haloalkyl, -C(O)(CH₂)ₙS(O)ₙ-C₁₋₆-alkyl, -C(O)-C₁₋₃-alkoxy-C₁-alkyl ₋₆, -C(O)C₁₋₃-alkoxy-C₂₋₆-alkenyl, -C(O)C₁₋₃-alkoxy-C₂₋₆-alkynyl, -C(O)C₁₋₃-alkoxy-C₁₋₆-haloalkyl, -C (O)C₁₋₃-alkoxy-C₃₋₆-cycloalkyl, -C(O)O-C₁₋₃-alkoxy-C₁₋₆-alkyl, -C(O)C₁₋₃-alkoxy-C₁₋₃-alkoxy-C₁₋₆-alkyl, -C(O)(CH₂)ₙNR⁵R⁶, -C(O)-(CH₂)ₙ-NR⁷C(O)R⁸, -C(O)-(CH₂)ₙ-O-N=CR⁵R⁵, -CN, -S(O) ₂NR¹⁶R¹⁷, -S(O)(=NR¹⁸)R¹⁹, -C(O)C(O)R²⁰, -C(O)C(R²³)=N-O-R²⁴ or -C(O)C(R²³)=N- NR²⁵R²⁶, -(CH₂)ₙ-phenyl, -C(O)-(CH₂)ₙ-phenyl, -S(O)ₙ-(CH₂)ₙ-phenyl, -heterocyclyl, -C(O)-(CH₂)ₙ -heterocyclyl, - C(O)(CH₂)ₙO-(CH₂)ₙ-heterocyclyl, -S(O)ₙ-(CH₂)ₙ-heterocyclyl, where each heterocyclyl is a 5- or 6-membered heterocyclyl which may be aromatic, saturated or partially saturated and may contain from 1 to 4 heteroatoms, each independently selected from the group consisting of oxygen, nitrogen and sulfur, and wherein said heterocyclyl or phenyl groups are optionally substituted with one, two or three substituents independently selected from the group consisting of alkyl C₁₋₃, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; R⁵ is selected from the group consisting of hydrogen and C₁₋₆ alkyl; R⁶ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₁₋₆ haloalkyl, hydroxyl-, C₁₋₆ alkoxy, C₃₋₆ cycloalkyl, -(C₁₋₄ alkoxy)( C₁₋₆ alkyl), -(C₁₋₃ alkoxy)(C₁₋₆ haloalkyl), -(CR⁹R¹⁰)(C₁₋₆ haloalkyl), -(CR⁹R¹⁰)C(O)NR⁵R⁵, phenyl, -pyridyl, where phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; or R⁵ and R⁶ together form -CH₂CH₂OCH₂CH₂-; and R⁷ is selected from the group consisting of hydrogen and C₁₋₆ alkyl; R⁸ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkyl, phenyl, -pyridyl, wherein phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; R⁹ is hydrogen or methyl; R¹⁰ is hydrogen or methyl; or R⁹ and R¹⁰ together form -CH₂CH₂-; and R¹¹ is hydrogen or methyl; R¹² is selected from the group consisting of hydrogen, C₁₋₆ alkyl, hydroxy, and (C₁₋₆ alkoxy)-; R¹³ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, hydroxyl, and C₁₋₆ alkoxy; or R¹² and R¹³ together form -CH₂-X-CH₂-; and X is selected from the group consisting of O, S, and N-R¹⁴; R¹⁴ is selected from the group consisting of hydrogen, C₁₋₃-alkyl, and C₁₋₃-alkoxy; R¹⁵ is independently selected from the group consisting of C₁₋₄ alkyl, C₁₋₄ haloalkyl, cyano, and halogen; R¹⁶ is hydrogen or C₁₋₆ alkyl; and R¹⁷ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₃₋₆ cycloalkyl, (C₁₋₆ alkoxy)-(C₁₋₃ alkyl)-,-C(O)(C₁₋₆ alkyl), -C( O)O(C₁₋₆ alkyl) and CH₂CN; or R¹⁶ and R¹⁷ together form -CH₂CH₂OCH₂CH₂-, -CH₂CH₂S(O)₂CH₂CH₂-; R¹⁸ is hydrogen or C₁₋₆ alkyl; R¹⁹ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy, C₃₋₆ cycloalkyl, phenyl, -pyridyl, where phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; R²⁰ is selected from the group consisting of C₁₋₆ alkyl, C₁₋₆ haloalkyl, (C₁₋₆ alkoxy)-, C₁₋₆ haloalkoxy, -NR²¹R²², phenyl, and -pyridyl, where phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano, and nitro; R²¹ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₁₋₆ alkoxy, (C₁₋₆ alkoxy)(C₁₋₃ alkyl)-, C₃₋₆ cycloalkyl, (C₁₋₆ haloalkyl)-, and (C₁₋ haloalkoxy ₆)-, -C(O)(C₁₋₆ alkyl), phenyl, -pyridyl, wherein phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋ haloalkyl ₃, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; R²² is hydrogen or C₁₋₆ alkyl; or R²¹ and R²² together form -CH₂CH₂OCH₂CH₂-; R²³ is selected from the group consisting of hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, and C₁₋₆ haloalkoxy; R²⁴ is selected from the group consisting of hydrogen, C₁₋₆-alkyl, (C₁₋₆-alkoxy)(C₁₋₃-alkyl)-, C₃₋₆-cycloalkyl-, -CH₂CN, tetrahydropyranyl-, phenyl, and -pyridyl, where phenyl and pyridyl are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano and nitro; R²⁵ is hydrogen or C₁₋₆ alkyl; R²⁶ is hydrogen or C₁₋₆ alkyl; G is selected from the group consisting of hydrogen, -(CH₂)ₙ-Rᵃ, -C(O)-Rᵃ, -C(O)-(CRᶜRᵈ)ₙ-O-Rᵇ, -C(O)NRᵃRᵃ, - S(O)₂-Rᵃ and C₁₋₈ alkoxy-C₁₋₃ alkyl-; Rᵃ is independently selected from the group consisting of hydrogen, C₁₋₈ alkyl, C₁₋₃ haloalkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₃₋₆ cycloalkyl, heterocyclyl, and phenyl, wherein said heterocyclyl and phenyl groups are optionally substituted with one , two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano, and nitro; Rᵇ is selected from the group consisting of C₁₋₈ alkyl, C₁₋₃ haloalkyl, C₂₋₈ alkenyl, C₂₋₈ alkynyl, C₃₋₆ cycloalkyl, heterocyclyl and phenyl, wherein said heterocyclyl and phenyl groups are optionally substituted with one, two or three substituents independently selected from the group consisting of C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃ alkoxy, C₂₋₃ alkenyl, C₂₋₃ alkynyl, halogen, cyano, and nitro; Rᶜ is hydrogen or C₁₋₃ alkyl; Rᵈ is hydrogen or C₁₋₃ alkyl; and n is independently 0, 1 or 2; or an agriculturally acceptable salt thereof.

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