AR114165A1 - Derivados de bencimidazol y benzotiazol para utilizar en el combate de plagas de invertebrados - Google Patents
Derivados de bencimidazol y benzotiazol para utilizar en el combate de plagas de invertebradosInfo
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- AR114165A1 AR114165A1 ARP180103773A ARP180103773A AR114165A1 AR 114165 A1 AR114165 A1 AR 114165A1 AR P180103773 A ARP180103773 A AR P180103773A AR P180103773 A ARP180103773 A AR P180103773A AR 114165 A1 AR114165 A1 AR 114165A1
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- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- 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
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- A01N47/42—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 containing —N=CX2 groups, e.g. isothiourea
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- 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
- C07D401/12—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 chain containing hetero atoms as chain links
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
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Abstract
Éstos compuestos son útiles para combatir o controlar plagas de invertebrados, en particular plagas de artrópodos y nematodos. También se provee un método para controlar plagas de invertebrados mediante el uso de éstos compuestos, a un material de propagación vegetal y a una composición agrícola y veterinaria que comprende dichos compuestos. Reivindicación 1: Un compuesto caracterizado por la fórmula (1), en donde A¹ es N o CRA; A² es N o CRB; A³ es N o CRB¹; W es O, S(=O)ₘ, o NR⁶; RA, RB y RB¹ son, independientemente entre sí, H, halógeno, N₃, OH, CN, NO₂, -SCN, -SF₅, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalcoxi, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₁₋₄-alquil-C₃₋₆-cicloalcoxi, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, NRᵇRᶜ, C₁₋₆-alquilen-NRᵇRᶜ, O-C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, NH-C₁₋₆-alquilen-NRᵇRᶜ, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ, o S(=O)ₘRᵉ, fenilo, fenoxi, fenilcarbonilo, feniltio, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Q es -N=C(X)-, -N(R²)-C(=NR)-, o -N(R²)-C(=S)-; en donde Ar está unido a cualquier lado de Q; X es idéntico o diferente, H, halógeno, SR⁷, OR⁸, N(R³)₂, -CR⁴=N(OCH₃), CN, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₃₋₆-cicloalquilo, en donde las porciones alquilo, alquenilo, alquinilo y cicloalquilo son no sustituidas o sustituidas con halógeno; fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con R⁵; R⁵ es halógeno, N₃, OH, CN, NO₂, -SCN, -SF₅, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalcoxi, C₃₋₆-cicloalquiltio, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquiltio, alquenilo, alquinilo, cicloalquilo, cicloalcoxi y cicloalquiltio son no sustituidas o sustituidas con halógeno, C(O)-ORᵃ, NRᵇRᶜ, C₁₋₆-alquilen-NRᵇRᶜ, O-C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, NH-C₁₋₆-alquilen-NRᵇRᶜ, C(O)-NRᵇRᶜ, C(O)-Rᵈ, SO₂NRᵇRᶜ, o S(=O)ₘRᵉ; R² es H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(O)-ORᵃ, C₁₋₆-alquil-C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(O)-NRᵇRᶜ, C(O)-Rᵈ, SO₂NRᵇRᶜ, S(=O)ₘRᵉ, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; R es idéntico o diferente, H, CN, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₃₋₆-cicloalquilo, en donde las porciones alquilo, alquenilo, alquinilo y cicloalquilo son no sustituidas o sustituidas con halógeno, SR⁷, OR⁸, N(R³)₂, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con R⁵; R⁴ es H, halógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ, R⁷ es C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; R⁸ es C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; R³, R⁶ son, idénticos o diferentes, H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquil-C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(O)-NRᵇRᶜ, C(O)-Rᵈ, SO₂NRᵇRᶜ, S(=O)ₘRᵉ, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Ar es fenilo o hetarilo de 5 ó 6 miembros, que son no sustituidos o sustituidos con RAʳ, en donde RAʳ es halógeno, N₃, OH, CN, NO₂, -SCN, -SF₅, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalcoxi, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, NRᵇRᶜ, C₁₋₆-alquilen-NRᵇRᶜ, O-C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, NH-C₁₋₆-alquilen-NRᵇRᶜ, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ o S(=O)ₘRᵉ, fenilo, fenoxi, fenilcarbonilo, feniltio o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; R¹ es una porción de la fórmula Y-Z-T-R¹¹ o Y-Z-T-R¹²; en donde Y es -CRʸᵃ=N-, en donde N está unido a Z; -NRʸᶜ-C(=O)-, en donde C(=O) está unido a Z; o -NRʸᶜ-C(=S)-, en donde C(=S) está unido a Z; Z es un enlace simple; -NRᶻᶜ-C(=O)-, en donde C(=O) está unido a T; -NRᶻᶜ-C(=S)-, en donde C(=S) está unido a T; -N=C(S-Rᶻᵃ)-, en donde T está unido al átomo de carbono; o -NRᶻᶜ-C(S-Rᶻᵃ)=, en donde T está unido al átomo de carbono; T es O, N o N-RT; R¹¹ es C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₁₋₄-alquil-C₃₋₆-cicloalcoxi, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, arilo, aril-carbonilo, aril-C₁₋₄-alquilo, ariloxi-C₁₋₄-alquilo, hetarilo, carbonil-hetarilo, hetaril-C₁₋₄-alquilo o hetariloxi-C₁₋₄-alquilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᵍ y en donde el hetarilo es un hetarilo monocíclico de 5 ó 6 miembros o un hetarilo bicíclico de 8, 9 ó 10 miembros; R¹² es un radical de la fórmula (2); en donde # indica el punto de unión a T; R¹²¹, R¹²², R¹²³ son, idénticos o diferentes, H, halógeno, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi, C₂₋₆-alqueniloxi, C₂₋₆-alquiniloxi, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₁₋₆-alquilcarbonlioxi, C₁₋₆-alquenilcarbonlioxi, C₃₋₆-cicloalquilcarbonlioxi, en donde las porciones alquilo, alcoxi, alquenilo, alqueniloxi, alquinilo, alquiniloxi y cicloalquilo son no sustituidas o sustituidas con halógeno, o NRᵇRᶜ, o uno de R¹²¹, R¹²², R¹²³ también puede ser oxo; R¹²⁴ es H, C₁₋₆-alquilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi o C₂₋₆-alqueniloxi, en donde las porciones alquilo, alcoxi, alquenilo y alqueniloxi son no sustituidas o sustituidas con halógeno; y en donde Rʸᵃ es H, halógeno, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₁₋₄-alquil-C₃₋₆-cicloalquilo, C₁₋₄-alquil-C₃₋₆-cicloalcoxi, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ, S(=O)ₘRᵉ, fenilo o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rʸᶜ, Rᶻᶜ son, idénticos o diferentes, H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₄-alquil-C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, o C₁₋₄-alquil-C₃₋₆-cicloalquilo, C₁₋₄-alquil-C₃₋₆-cicloalcoxi, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno; RT es H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₄-alquil-C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ, S(=O)ₘRᵉ, fenilo o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rᶻᶜ junto con RT, si está presente, puede formar C₁₋₆-alquileno o un grupo C₂₋₆-alquenileno lineal, donde, en el C₁₋₆-alquileno lineal y el C₂₋₆-alquenileno lineal, una porción CH₂ se puede reemplazar con un carbonilo o un C=N-R y/o en donde 1 ó 2 porciones CH₂ se pueden reemplazar con O ó S y/o en donde C₁₋₆-alquileno lineal y C₂₋₆-alquenileno lineal pueden ser no sustituidos o sustituidos con Rʰ; Rᶻᵃ es H, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₄-alquil-C₁₋₆-alcoxi, C₃₋₆-cicloalquilo, C₁₋₄-alquil-C₃₋₆-cicloalcoxi, C₁₋₄-alquil-C₃₋₆-cicloalquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, fenilo, fenilcarbonilo o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rᶻᵃ junto con RT, si está presente, puede formar C₁₋₆-alquileno o un grupo C₂₋₆-alquenileno lineal, donde, en el C₁₋₆-alquileno lineal y el C₂₋₆-alquenileno lineal, una porción CH₂ se puede reemplazar con un carbonilo o un C=N-R y/o en donde 1 ó 2 porciones CH₂ se pueden reemplazar con O ó S y/o en donde C₁₋₆-alquileno lineal y C₂₋₆-alquenileno lineal pueden ser no sustituidos o sustituidos con Rʰ; Rᵃ, Rᵇ y Rᶜ son, idénticos o diferentes, H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C₁₋₆-alquilen-CN, fenilo o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rᵈ es H, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, fenilo, o -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rᵉ es C₁₋₆-alquilo, C₃₋₆-cicloalquilo, C₃₋₆-cicloalquil-C₁₋₄-alquilo, en donde las porciones alquilo, cicloalquilo son no sustituidas o sustituidas con halógeno, fenilo y -CH₂-fenilo, en donde los anillos de fenilo son no sustituidos o sustituidos con Rᶠ; Rᶠ es halógeno, N₃, OH, CN, NO₂, -SCN, -SF₅, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalcoxi, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, NRᵇRᶜ, C₁₋₆-alquilen-NRᵇRᶜ, O-C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, NH-C₁₋₆-alquilen-NRᵇRᶜ, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ o S(=O)ₘRᵉ; Rᵍ es halógeno, N₃, OH, CN, NO₂, -SCN, -SF₅, C₁₋₆-alquilo, C₁₋₆-alcoxi, C₂₋₆-alquenilo, tri-C₁₋₆-alquilsililo, C₂₋₆-alquinilo, C₁₋₆-alcoxi-C₁₋₄-alquilo, C₁₋₆-alcoxi-C₁₋₄-alcoxi, C₃₋₆-cicloalquilo, C₃₋₆-cicloalcoxi, C₃₋₆-cicloalquil-C₁₋₄-alquilo, C₃₋₆-cicloalcoxi-C₁₋₄-alquilo, en donde las porciones alquilo, alcoxi, alquenilo, alquinilo, cicloalquilo y cicloalcoxi son no sustituidas o sustituidas con halógeno, C(=O)-ORᵃ, NRᵇRᶜ, C₁₋₆-alquilen-NRᵇRᶜ, O-C₁₋₆-alquilen-NRᵇRᶜ, C₁₋₆-alquilen-CN, NH-C₁₋₆-alquilen-NRᵇRᶜ, C(=O)-NRᵇRᶜ, C(=O)-Rᵈ, SO₂NRᵇRᶜ o S(=O)ₘRᵉ; Rʰ es halógeno, OH, C₁₋₆-alquilo, C₃₋₆-cicloalquilo, o CN; m es 0, 1 ó 2; siempre que cuando Z es un enlace simple, RT no sea H; y los N-óxidos, estereoisómeros, tautómeros y las sales aceptables en la agricultura o veterinaria de aquel.
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CN111491925A (zh) | 2020-08-04 |
CL2020001680A1 (es) | 2020-09-21 |
RU2020123130A (ru) | 2022-01-21 |
AU2018387639B2 (en) | 2023-09-07 |
IL275382B2 (en) | 2023-06-01 |
IL275382A (en) | 2020-07-30 |
KR102660151B1 (ko) | 2024-04-24 |
CN111491925B (zh) | 2023-12-29 |
US11512054B2 (en) | 2022-11-29 |
JP2021507910A (ja) | 2021-02-25 |
EP3728199A1 (en) | 2020-10-28 |
CA3086083A1 (en) | 2019-06-27 |
AU2018387639A1 (en) | 2020-06-18 |
KR20200102449A (ko) | 2020-08-31 |
US20210070713A1 (en) | 2021-03-11 |
BR112020012566B1 (pt) | 2024-03-05 |
UA127604C2 (uk) | 2023-11-01 |
JP7285844B2 (ja) | 2023-06-02 |
WO2019121159A1 (en) | 2019-06-27 |
BR112020012566A2 (pt) | 2020-11-24 |
MX2020006566A (es) | 2020-09-25 |
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