AR093771A1 - METHOD TO CONTROL INSECTICIDE RESISTANT INSECTS - Google Patents

METHOD TO CONTROL INSECTICIDE RESISTANT INSECTS

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Publication number
AR093771A1
AR093771A1 ARP130103518A ARP130103518A AR093771A1 AR 093771 A1 AR093771 A1 AR 093771A1 AR P130103518 A ARP130103518 A AR P130103518A AR P130103518 A ARP130103518 A AR P130103518A AR 093771 A1 AR093771 A1 AR 093771A1
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Argentina
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alkyl
alkoxy
group
radicals
partially
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ARP130103518A
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Spanish (es)
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Basf Se
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Publication of AR093771A1 publication Critical patent/AR093771A1/en

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    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • 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
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring

Abstract

Reivindicación 1: Un método para controlar insectos que son resistentes a un insecticida, caracterizado porque comprende aplicar a los insectos resistentes a insecticidas al menos un compuesto de antranilamida activo como plaguicida de la fórmula (1) en donde R¹ se selecciona del grupo que consiste en halógeno, metilo y halometilo; R² se selecciona del grupo que consiste en hidrógeno, halógeno, halometilo y ciano; R³ se selecciona de hidrógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆, haloalquinilo C₂₋₆, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alcoxi C₁₋₄-alquilo C₁₋₄, haloalcoxi-alquilo C₁₋₄; C(=O)Rᵃ, C(=O)ORᵇ y C(=O)NRᶜRᵈ; R⁴ es hidrógeno o halógeno; R⁵, R⁶ se seleccionan, independientemente entre sí, del grupo que consiste en hidrógeno, alquilo C₁₋₁₀, cicloalquilo C₃₋₈, alquenilo C₂₋₁₀, alquinilo C₂₋₁₀, en donde los radicales alifáticos y cicloalifáticos antes mencionados se pueden sustituir con 1 a 10 sustituyentes Rᵉ, y fenilo, que es no sustituido o tiene de 1 a 5 sustituyentes Rᶠ; o R⁵ y R⁶ juntos representan cadenas de alquileno C₂₋₇, alquenileno C₂₋₇ o alquinileno C₆₋₉ que forman, junto con el átomo de azufre al que están unidas, un anillo saturado, parcialmente insaturado o totalmente insaturado de 3, 4, 5, 6, 7, 8, 9 ó 10 miembros, en donde de 1 a 4 de los grupos CH₂ en la cadena de alquileno C₂₋₇, de 1 a 4 de cualquiera de los grupos CH₂ o CH en la cadena de alquenileno C₂₋₇, o de 1 a 4 de cualquiera de los grupos CH₂ en la cadena de alquinileno C₆₋₉ se pueden reemplazar por 1 a 4 grupos seleccionados independientemente del grupo que consiste en C=O, C=S, O, S, N, NO, SO, SO₂ y NH, y en donde los átomos de carbono y/o nitrógeno en las cadenas de alquileno C₂₋₇, alquenileno C₂₋₇ o alquinileno C₆₋₉ se pueden sustituir con 1 a 5 sustituyentes seleccionados independientemente del grupo que consiste en halógeno, ciano, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, haloalquil C₁₋₆tio, cicloalquilo C₃₋₈, halocicloalquilo C₃₋₈, alquenilo C₂₋₆, haloalquenilo C₂₋₆, alquinilo C₂₋₆ y haloalquinilo C₂₋₆; estos sustituyentes son idénticos o diferentes entre sí si hay más de un sustituyente presente; R⁷ se selecciona del grupo que consiste en bromo, cloro, difluorometilo, trifluorometilo, nitro, ciano, OCH₃, OCHF₂, OCH₂F, OCH₂CF₃, S(=O)ₙCH₃ y S(=O)ₙCF₃; Rᵃ se selecciona del grupo que consiste en alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, en donde uno o más grupos CH₂ de los radicales antes mencionados se pueden reemplazar por un grupo C=O, y/o las porciones alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, parcial o totalmente halogenadas y/o pueden tener 1 ó 2 sustituyentes seleccionados de alcoxi C₁₋₄; fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden tener 1, 2 ó 3 sustituyentes seleccionados de alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, (alcoxi C₁₋₆)carbonilo, alquil C₁₋₆amino y di-(alquil C₁₋₆)amino; Rᵇ se selecciona del grupo que consiste en alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, alcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, en donde uno o más grupos CH₂ de los radicales antes mencionados se pueden reemplazar por un grupo C=O, y/o las porciones alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, parcial o totalmente halogenadas y/o pueden tener 1 ó 2 sustituyentes seleccionados de alcoxi C₁₋₄; fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden tener 1, 2 ó 3 sustituyentes seleccionados de alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆ y (alcoxi C₁₋₆)carbonilo; Rᶜ, Rᵈ se seleccionan, independientemente entre si e independientemente de cada caso, del grupo que consiste en hidrógeno, ciano, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde uno o más grupos CH₂ de los radicales antes mencionados se pueden reemplazar por un grupo C=O, y/o las porciones alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, parcial o totalmente halogenadas y/o pueden tener 1 ó 2 radicales seleccionados de alcoxi C₁₋₄; alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, haloalquil C₁₋₆tio, fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales mencionados pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden tener 1, 2 ó 3 sustituyentes seleccionados de alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆ y (alcoxi C₁₋₆)carbonilo; o Rᶜ y Rᵈ, junto con el átomo de nitrógeno al que están unidos, pueden formar un anillo heterocíclico saturado, parcialmente insaturado o totalmente insaturado de 3, 4, 5, 6 ó 7 miembros, que también puede contener 1 ó 2 heteroátomos o grupos de heteroátomos adicionales seleccionados de N, O, S, NO, SO y SO₂, como miembros del anillo, en donde el anillo heterocíclico se puede sustituir opcionalmente con halógeno, haloalquilo C₁₋₄, alcoxi C₁₋₄ o haloalcoxi C₁₋₄; Rᵉ se selecciona independientemente del grupo que consiste en halógeno, ciano, nitro, -OH, -SH, -SCN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde uno o más grupos CH₂ de los radicales antes mencionados se pueden reemplazar por un grupo C=O, y/o las porciones alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, pueden ser parcial o totalmente halogenadas y/o pueden tener 1 ó 2 radicales seleccionados de alcoxi C₁₋₄; alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, haloalquil C₁₋₆tio, -ORᵃ, -NRᶜRᵈ, S(O)ₙRᵃ, -S(O)ₙNRᶜRᵈ, -C(=O)Rᵃ, -C(=O)NRᶜRᶜ, -C(=O)ORᵇ, -C(=S)Rᵃ, -C(=S)NRᶜRᵈ, -C(=S)ORᵇ, -C(=S)SRᵇ, -C(=NRᶜ)Rᵇ, -C(=NRᶜ)NRᶜRᵈ, fenilo, bencilo, piridilo y fenoxi, en donde los cuatro últimos radicales mencionados pueden ser no sustituidos, parcial o totalmente halogenados y/o pueden tener 1, 2 ó 3 sustituyentes seleccionados de alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆ y haloalcoxi C₁₋₆; o dos radicales vecinos Rᵉ forman juntos un grupo =O, =CH(alquilo C₁₋₄), =C(alquil C₁₋₄)alquilo C₁₋₄, =N(alquilo C₁₋₆) o =NO(alquilo C₁₋₆); Rᶠ se selecciona independientemente del grupo que consiste en halógeno, ciano, nitro, -OH, -SH, -SCN, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₈, en donde uno o más grupos CH₂ de los radicales antes mencionados se pueden reemplazar por un grupo C=O, y/o las porciones alifáticas y cicloalifáticas de los radicales antes mencionados pueden ser no sustituidas, pueden ser parcial o totalmente halogenadas y/o pueden tener 1 ó 2 radicales seleccionados de alcoxi C₁₋₄; alcoxi C₁₋₆, haloalcoxi C₁₋₆, alquil C₁₋₆tio, alquil C₁₋₆sulfinilo, alquil C₁₋₆sulfonilo, haloalquil C₁₋₆tio, -ORᵃ, -NRᶜRᵈ,Claim 1: A method for controlling insects that are resistant to an insecticide, characterized in that it comprises applying to insecticide resistant insects at least one active anthranilamide compound as a pesticide of the formula (1) wherein R¹ is selected from the group consisting of halogen, methyl and halomethyl; R² is selected from the group consisting of hydrogen, halogen, halomethyl and cyano; R³ is selected from hydrogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₂₋₆ haloalkynyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₁₋₄ alkoxy -C₁₋₄ alkyl, haloalkoxy-C₁₋₄ alkyl; C (= O) Rᵃ, C (= O) ORᵇ and C (= O) NRᶜRᵈ; R⁴ is hydrogen or halogen; R⁵, R⁶ are independently selected from the group consisting of hydrogen, C₁₋₁₀ alkyl, C₃₋₈ cycloalkyl, C₂₋₁₀ alkenyl, C₂₋₁₀ alkynyl, wherein the aforementioned aliphatic and cycloaliphatic radicals can be substituted with 1 to 10 Rᵉ substituents, and phenyl, which is unsubstituted or has 1 to 5 Rᶠ substituents; or R⁵ and R⁶ together represent chains of C₂₋₇ alkylene, C₂₋₇ alkenylene or C₆₋₉ alkynylene which form, together with the sulfur atom to which they are attached, a saturated, partially unsaturated or fully unsaturated ring of 3, 4, 5, 6, 7, 8, 9 or 10 members, where 1 to 4 of the CH₂ groups in the C₂₋₇ alkylene chain, 1 to 4 of any of the CH₂ or CH groups in the C₂ alkenylene chain ₋₇, or 1 to 4 of any of the CH₂ groups in the C₆₋₉ alkynylene chain can be replaced by 1 to 4 groups independently selected from the group consisting of C = O, C = S, O, S, N , NO, SO, SO₂ and NH, and wherein the carbon and / or nitrogen atoms in the C₂₋₇ alkylene, C₂₋₇ alkenylene or C₆₋₉ alkynylene chains may be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, haloalkoxy C₁₋₆, C₁₋₆thio alkyl, C₁₋₆thio haloalkyl, C₃₋₈ cycloalkyl, C₃₋₈ halocycloalkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl and C₂₋₆ haloalkynyl; these substituents are identical or different from each other if more than one substituent is present; R⁷ is selected from the group consisting of bromine, chlorine, difluoromethyl, trifluoromethyl, nitro, cyano, OCH₃, OCHF₂, OCH₂F, OCH₂CF₃, S (= O) ₙCH₃ and S (= O) ₙCF₃; Rᵃ is selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₁₋₆ alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, wherein one or more CH₂ groups of the aforementioned radicals may be replaced by a C = O group, and / or the aliphatic and cycloaliphatic portions of the aforementioned radicals may be unsubstituted, partially or totally halogenated and / or may have 1 or 2 substituents selected from C₁₋₄ alkoxy; phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals may be unsubstituted, partially or totally halogenated and / or may have 1, 2 or 3 substituents selected from C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy , C₁₋₆ haloalkoxy, (C₁₋₆ alkoxy) carbonyl, C₁₋₆amino alkyl and di- (C₁₋₆ alkyl) amino; Rᵇ is selected from the group consisting of C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, C₁₋₆ alkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, wherein one or more CH₂ groups of the aforementioned radicals may be replaced by a C = O group, and / or the aliphatic and cycloaliphatic portions of the aforementioned radicals may be unsubstituted, partially or totally halogenated and / or may have 1 or 2 substituents selected from C₁₋₄ alkoxy; phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals may be unsubstituted, partially or totally halogenated and / or may have 1, 2 or 3 substituents selected from C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy , C₁₋₆ haloalkoxy and (C₁₋₆ alkoxy) carbonyl; Rᶜ, Rᵈ are selected, independently of each other and independently of each case, from the group consisting of hydrogen, cyano, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, wherein one or more groups CH₂ of the aforementioned radicals may be replaced by a group C = O, and / or the aliphatic and cycloaliphatic portions of the aforementioned radicals may be unsubstituted, partially or totally halogenated and / or may have 1 or 2 radicals selected from alkoxy C₁₋₄; C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, haloC₁₋₆tio alkyl, phenyl, benzyl, pyridyl and phenoxy, wherein the last four radicals mentioned may be unsubstituted, partially or totally halogenated and / or may have 1, 2 or 3 substituents selected from C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy and (C₁₋₆ alkoxy) carbonyl; or Rᶜ and Rᵈ, together with the nitrogen atom to which they are attached, can form a saturated, partially unsaturated or fully unsaturated heterocyclic ring of 3, 4, 5, 6 or 7 members, which can also contain 1 or 2 heteroatoms or groups of additional heteroatoms selected from N, O, S, NO, SO and SO₂, as ring members, wherein the heterocyclic ring can be optionally substituted with halogen, C₁₋₄ haloalkyl, C₁₋₄ alkoxy or C₁₋₄ haloalkoxy; Rᵉ is independently selected from the group consisting of halogen, cyano, nitro, -OH, -SH, -SCN, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, wherein one or more groups CH₂ of the aforementioned radicals may be replaced by a group C = O, and / or the aliphatic and cycloaliphatic portions of the aforementioned radicals may be unsubstituted, may be partially or totally halogenated and / or may have 1 or 2 radicals selected C₁₋₄ alkoxy; C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆tio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, haloC₁₋₆tio alkyl, -ORᵃ, -NRᶜRᵈ, S (O) ₙRᵃ, -S (O) ₙNRᶜRᵈ, - C (= O) Rᵃ, -C (= O) NRᶜRᶜ, -C (= O) ORᵇ, -C (= S) Rᵃ, -C (= S) NRᶜRᵈ, -C (= S) ORᵇ, -C ( = S) SRᵇ, -C (= NRᶜ) Rᵇ, -C (= NRᶜ) NRᶜRᵈ, phenyl, benzyl, pyridyl and phenoxy, where the last four radicals mentioned may be unsubstituted, partially or totally halogenated and / or may have 1, 2 or 3 substituents selected from C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy and C₁₋₆ haloalkoxy; or two neighboring radicals Rᵉ together form a group = O, = CH (C₁₋₄ alkyl), = C (C₁₋₄ alkyl) C₁₋₄ alkyl, = N (C₁₋₆ alkyl) or = NO (C₁₋₆ alkyl ); Rᶠ is independently selected from the group consisting of halogen, cyano, nitro, -OH, -SH, -SCN, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₈ cycloalkyl, wherein one or more groups CH₂ of the aforementioned radicals may be replaced by a group C = O, and / or the aliphatic and cycloaliphatic portions of the aforementioned radicals may be unsubstituted, may be partially or totally halogenated and / or may have 1 or 2 radicals selected C₁₋₄ alkoxy; C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆thio alkyl, C₁₋₆sulfinyl alkyl, C₁₋₆sulfonyl alkyl, C₁₋₆tio haloalkyl, -ORᵃ, -NRᶜRᵈ,

ARP130103518A 2012-10-01 2013-09-27 METHOD TO CONTROL INSECTICIDE RESISTANT INSECTS AR093771A1 (en)

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US201261729349P 2012-11-22 2012-11-22
US201361763987P 2013-02-13 2013-02-13
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