AR119399A1 - Compuestos herbicidas - Google Patents

Compuestos herbicidas

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Publication number
AR119399A1
AR119399A1 ARP200101969A ARP200101969A AR119399A1 AR 119399 A1 AR119399 A1 AR 119399A1 AR P200101969 A ARP200101969 A AR P200101969A AR P200101969 A ARP200101969 A AR P200101969A AR 119399 A1 AR119399 A1 AR 119399A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
alkoxy
hydrogen
haloalkyl
Prior art date
Application number
ARP200101969A
Other languages
English (en)
Inventor
Alan Joseph Hennessy
Elizabeth Pearl Jones
Suzanna Jane Dale
Alexander William Gregory
Ian Thomas Tinmouth Houlsby
Yunas Bhonoah
Julia Comas-Barcelo
Original Assignee
Syngenta Crop Protection Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Crop Protection Ag filed Critical Syngenta Crop Protection Ag
Publication of AR119399A1 publication Critical patent/AR119399A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • A—HUMAN NECESSITIES
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/34—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
    • A01N43/42—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 condensed with carbocyclic rings
    • 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
    • A01N43/34—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
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    • 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
    • A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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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
    • A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
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    • 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
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
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    • C07D498/10—Spiro-condensed systems

Abstract

Reivindicación 1: Un compuesto de fórmula (1) en 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 es hidrógeno, metilo, etilo, metoxi o cloro; R³ se selecciona del grupo que consiste en metilo, etilo, metoxi y cloro; R⁴ se selecciona del grupo que consiste en D1, D2, D3, D4, D5, D6, D7, D8, D9, D10, D11, D12, D13, D14, D15, D16, D17, D18, D19, D20, D21 D22, D23, D24, D25, D26, D27, D28, D29, D30, D31, D32, D33, D34, D35 y D36 del grupo de fórmulas (2); Y se selecciona del grupo que consiste en O, CR²⁷R²⁸ y N-R²⁹; Z es N o CH; R⁴ᶜ se selecciona del grupo que consiste en hidrógeno, 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, en donde cada heterociclilo es un heterociclilo de 5 ó 6 miembros que puede ser aromático, saturado o parcialmente saturado y puede contener de 1 a 4 heteroátomos seleccionados cada uno independientemente entre el grupo que consiste en oxígeno, nitrógeno y azufre y en donde dichos grupos heterociclilo o fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R⁵ se selecciona del grupo que consiste en hidrógeno y alquilo C₁₋₆; R⁶ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, haloalquilo C₁₋₆, hidroxilo, 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, en donde el fenilo y el piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; o R⁵ y R⁶ juntos forman -CH₂CH₂OCH₂CH₂-; y R⁷ se selecciona del grupo que consiste en hidrógeno y alquilo C₁₋₆; R⁸ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, fenilo, -piridilo, en donde el fenilo y el piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en 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 juntos forman -CH₂CH₂-; y R¹¹ es hidrógeno o metilo; R¹² se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, hidroxilo y alcoxi C₁₋₆; R¹³ se selecciona del grupo que consiste en 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 que consiste en alquilo C₁₋₄, haloalquilo C₁₋₄, ciano y halógeno; R¹⁶ es hidrógeno o alquilo C₁₋₆; y R¹⁷ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, cicloalquilo C₃₋₆, alcoxi C₁₋₆-alquilo 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 que consiste en hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, fenilo, -piridilo, en donde el fenilo y el piridilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²⁰ se selecciona del grupo que consiste en alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆-, haloalcoxi C₁₋₆, -NR²¹R²², fenilo y -piridilo, en donde el fenilo y el piridilo están opcionalmente sustituidos por uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; R²¹ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆, alcoxi C₁₋₆alquilo C₁₋₃-, cicloalquilo C₃₋₆, haloalquilo C₁₋₆- y haloalcoxi C₁₋₆-, -C(O) alquilo C₁₋₆, fenilo, -piridilo, en donde el fenilo y el piridilo están opcionalmente sustituidos por uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en 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 que consiste en hidrógeno, alquilo C₁₋₆, alcoxi C₁₋₆ alquilo C₁₋₃, cicloalquilo C₃₋₆, -CH₂CN, tetrahidropiranilo-, fenilo y -piridilo, en donde el fenilo y el piridilo están opcionalmente sustituidos por uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en 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; R²⁷ es hidrógeno o alquilo C₁₋₄; R²⁸ es hidrógeno o alquilo C₁₋₄; R²⁹ se selecciona del grupo que consiste en hidrógeno, alquilo C₁₋₄, alcoxi C₁₋₄-, haloalquilo C₁₋₄, -C(=O) alquilo C₁₋₄, -C(=O) haloalquilo C₁₋₄; y R³⁰ y R³¹ se seleccionan independientemente del grupo que consiste en hidrógeno, halógeno, alquilo C₁₋₃, haloalquilo C₁₋₃ y alcoxi C₁₋₃pero en donde ambos R³⁰ y R³¹ no son hidrógeno; G se selecciona del grupo que consiste en hidrógeno, -(CH₂)ₙ-Rᵃ, -C(O)-Rᵃ, -C(O)-(CRᶜRᵈ)ₙ-O-Rᵇ, -C(O)-(CRᶜRᵈ)ₙ-S-Rᵇ, -C(O)NRᵃRᵃ, -S(O)₂-Rᵃ y alcoxi C₁₋₈-alquilo C₁₋₃-; Rᵃ se selecciona independientemente del grupo que consiste en hidrógeno, alquilo C₁₋₈, haloalquilo C₁₋₃, alquenilo C₂₋₈, alquinilo C₂₋₈, cicloalquilo C₃₋₆, heterociclilo y fenilo, en donde dichos grupos heterociclilo y fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en alquilo C₁₋₃, haloalquilo C₁₋₃, alcoxi C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, halógeno, ciano y nitro; Rᵇ se selecciona del grupo que consiste en alquilo C₁₋₈, haloalquilo C₁₋₃, alquenilo C₂₋₈, alquinilo C₂₋₈, cicloalquilo C₃₋₆, heterociclilo y fenilo, en donde dichos grupos heterociclilo y fenilo están opcionalmente sustituidos con uno, dos o tres sustituyentes seleccionados independientemente del grupo que consiste en 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 del mismo.
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