AR094840A1 - FUNGICIDE PIRAZOLS - Google Patents

FUNGICIDE PIRAZOLS

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Publication number
AR094840A1
AR094840A1 ARP140100538A ARP140100538A AR094840A1 AR 094840 A1 AR094840 A1 AR 094840A1 AR P140100538 A ARP140100538 A AR P140100538A AR P140100538 A ARP140100538 A AR P140100538A AR 094840 A1 AR094840 A1 AR 094840A1
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Argentina
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independently selected
ring
alkyl
atoms
annular members
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ARP140100538A
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Spanish (es)
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Edmund Taggi Andrew
Francis Bereznak James
Keith Long Jeffrey
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Du Pont
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Publication of AR094840A1 publication Critical patent/AR094840A1/en

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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D405/10—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 aromatic rings
    • 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
    • C07D405/12—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

Abstract

Además, se describen composiciones que contienen a éstos compuestos y métodos para controlar enfermedades de las plantas causadas por un patógeno fúngico; el método comprende aplicar una cantidad eficaz de un compuesto o una composición de los aquí reivindicados. Reivindicación 1: Un compuesto seleccionado de la fórmula (1), N-óxidos y sales de estos, caracterizada porque Q¹ es un anillo de fenilo o un sistema anular de naftalenilo, cada anillo o sistema anular opcionalmente sustituido con hasta 5 sustituyentes independientemente seleccionados de R³ᵃ y R³ᵇ; o un anillo heterocíclico totalmente insaturado de 5 a 6 miembros o un sistema anular bicíclico heteroaromático de 8 a 10 miembros, cada anillo o sistema anular contiene miembros anulares seleccionados de átomos de carbono y 1 a 4 heteroátomos independientemente seleccionados de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros anulares de carbono se seleccionan independientemente de C(=O) y C(=S), y los miembros anulares del átomo de azufre se seleccionan independientemente de S(=O)ᵘ(=NR²⁷)ᵛ, cada anillo o sistema anular opcionalmente sustituido con hasta 5 sustituyentes independientemente seleccionados de R³ᵃ y R³ᵇ en los miembros anulares del átomo de carbono y seleccionados de 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 y dialquilaminoalquilo C₃₋₄ en los miembros anulares del átomo de nitrógeno; Q² es un anillo de fenilo o un sistema anular de naftalenilo, cada anillo o sistema anular opcionalmente sustituido con hasta 5 sustituyentes independientemente seleccionados de R³ᵃ y R³ᵇ; o un anillo heterocíclico totalmente insaturado de 5 a 6 miembros o un sistema anular bicíclico heteroaromático de 8 a 10 miembros, cada anillo o sistema anular contiene miembros anulares seleccionados de átomos de carbono y 1 a 4 heteroátomos independientemente seleccionados de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros anulares de carbono se seleccionan independientemente de C(=O) y C(=S), y los miembros anulares del átomo de azufre se seleccionan independientemente de S(=O)ᵘ(=NR²⁷)ᵛ, cada anillo o sistema anular opcionalmente sustituido con hasta 5 sustituyentes independientemente seleccionados de R³ᵃ y R³ᵇ en los miembros anulares del átomo de carbono y seleccionados de 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 y dialquilaminoalquilo C₃₋₄ en los miembros anulares del átomo de nitrógeno; X es O, S(=O)ₘ, NR⁴ o CR⁵ᵃOR⁵ᵇ; R¹ es H, ciano, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alcoxialquilo C₂₋₆, alcoxi C₁₋₆, haloalcoxi C₁₋₆, C₍₌O₎OR⁶ o C(=O)NR⁷R⁸; R¹ᵃ es H; o R¹ᵃ y R¹ se toman junto con el átomo de carbono al cual están unidos para formar un anillo de ciclopropilo sustituido opcionalmente con hasta 2 sustituyentes seleccionados independientemente de halógeno y metilo; R² es H, ciano, halógeno, alquilo C₁₋₃, alquenilo C₂₋₃, alquinilo C₂₋₃, haloalquilo C₁₋₃, haloalquenilo C₂₋₃, cianoalquilo C₂₋₃, hidroxialquilo C₁₋₃, alcoxi C₁₋₃ o alquiltio C₁₋₃ o ciclopropilo opcionalmente sustituido con hasta 2 sustituyentes independientemente seleccionados de halógeno y metilo; cada R³ᵃ es independientemente ciano, halógeno, hidroxi, nitro, alquilo C₁₋₄, haloalquilo C₁₋₄, alquenilo C₂₋₄, alquinilo C₂₋₄, cicloalquilo C₃₋₄, halocicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₆, alquilcicloalquilo C₄₋₆, alquiltio C₁₋₃, haloalquiltio C₁₋₃, alquilsulfinilo C₁₋₃, haloalquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, haloalquilsulfonilo C₁₋₃, alcoxi C₁₋₃, haloalcoxi C₁₋₃, cicloalcoxi C₃₋₇, alquilsulfoniloxi C₁₋₂, haloalquilsulfoniloxi C₁₋₂, alquilcarboniloxi C₂₋₃, alquilcarbonilo C₂₋₃, amino, metilamino, dialquilamino C₂₋₄, alquilcarbonilamino C₂₋₃, -CH(=O), -NHCH(=O), -SF₅, -SCºN, -C(=S)NR⁹ᵃR⁹ᵇ o -U-V-T; cada R³ᵇ es independientemente alquilo C₅₋₈, haloalquilo C₅₋₈, alquenilo C₅₋₈, alquinilo C₅₋₈, haloalquenilo C₂₋₈, haloalquinilo C₂₋₈, nitroalquilo C₁₋₈, nitroalquenilo C₂₋₈, cicloalquilo C₅₋₈, alquilcicloalquilo C₇₋₈, cicloalquilalquilo C₇₋₈, cicloalquilalquenilo C₅₋₁₂, cicloalquilalquinilo C₅₋₁₂, cicloalquilcicloalquilo C₆₋₁₂, alquiltio C₄₋₈, haloalquiltio C₄₋₈, alquilsulfinilo C₄₋₈, haloalquilsulfinilo C₄₋₈, alquilsulfonilo C₄₋₈, haloalquilsulfonilo C₄₋₈, alcoxi C₄₋₈, haloalcoxi C₅₋₈, alqueniloxi C₂₋₈, haloalqueniloxi C₂₋₈, alquiniloxi C₃₋₈, haloalquiniloxi C₃₋₈, cianoalcoxi C₂₋₈, cicloalcoxi C₈₋₁₂, halocicloalcoxi C₃₋₁₂, cicloalquilalcoxi C₄₋₁₂, cicloalquilalqueniloxi C₅₋₁₂, cicloalquilalquiniloxi C₅₋₁₂, alquilsulfoniloxi C₃₋₈, haloalquilsulfoniloxi C₃₋₈, alquilcarboniloxi C₄₋₈, alquilcarbonilo C₄₋₈, alquilamino C₂₋₈, alquilcarbonilamino C₄₋₈, trialquilsililo C₃₋₁₂, trialquilsililalquilo C₄₋₁₂, trialquilsililalcoxi C₄₋₁₂, -C(=NR⁹ᵃ)NR⁹ᵃOR⁹ᵃ, -CR¹⁰ᵃ=NOR¹⁰ᵇ, -CR¹⁰ᶜ=NNR⁹ᵃR⁹ᵇ, -NR⁹ᵃN=CR¹¹ᵃR¹¹ᵇ o -ON=CR¹¹ᵃR¹¹ᵇ; o cada R³ᵇ es independientemente -A(CR¹²ᵃR¹²ᵇ)ₙW; cada A es independientemente O ó un enlace directo; cada W es independientemente un anillo heterocíclico de 3 a 7 miembros que contiene miembros anulares seleccionados de átomos de carbono y 1 a 4 heteroátomos independientemente seleccionados de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros anulares del átomo de carbono se seleccionan independientemente de C(=O) y C(=S), el anillo opcionalmente sustituido con hasta 3 sustituyentes independientemente seleccionados de R¹³ en los miembros anulares del átomo de carbono y R¹⁴ en los miembros anulares del átomo de nitrógeno; R⁴ es H, amino, alquenilo C₂₋₆, alquinilo C₃₋₆, cicloalquilo C₃₋₆, -CH(=O), -S(=O)₂OM, -S(=O)ₘR¹⁵, -(C=Z)R¹⁶ u OR¹⁷; o alquilo C₁₋₆ o haloalquilo C₁₋₆, cada uno opcionalmente sustituido con hasta 2 sustituyentes independientemente seleccionados de R¹⁸; R⁵ᵃ es H o alquilo C₁₋₆; R⁵ᵇ es H, -CH(=O), alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₃₋₆, haloalquilo de C₁₋₆, cicloalquilo C₃₋₆, halocicloalquilo C₃₋₆, alcoxialquilo C₂₋₆, cianoalquilo C₂₋₆, alquilcarbonilo C₂₋₆, alcoxicarbonilo C₂₋₆, (alquiltio)carbonilo C₂₋₆, cicloalquilcarbonilo C₄₋₈, cicloalcoxicarbonilo C₄₋₈, (cicloalquiltio)carbonilo C₄₋₈, alcoxi(tiocarbonilo) C₂₋₆ o cicloalcoxi(tiocarbonilo) C₄₋₈; R⁶ es H, alquilo C₁₋₆ o haloalquilo C₁₋₆; R⁷ y R⁸ son cada uno independientemente H, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₆, cicloalquilalquilo C₄₋₈ o alquilcicloalquilo C₄₋₈ ; o R⁷ y R⁸ se toman junto con eIn addition, compositions containing these compounds and methods for controlling plant diseases caused by a fungal pathogen are described; The method comprises applying an effective amount of a compound or a composition of those claimed herein. Claim 1: A compound selected from the formula (1), N-oxides and salts thereof, characterized in that Q¹ is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 independently selected substituents of R³ᵃ and R³ᵇ; or a fully unsaturated 5 to 6 membered heterocyclic ring or an 8 to 10 membered heteroaromatic bicyclic ring system, each ring or ring system contains annular members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O atoms, up to 2 atoms of S and up to 4 atoms of N, where up to 3 annular carbon members are independently selected from C (= O) and C (= S), and the annular members of the sulfur atom are independently selected from S ( = O) ᵘ (= NR²⁷) ᵛ, each ring or ring system optionally substituted with up to 5 substituents independently selected from R³ᵃ and R³ᵇ on the annular members of the carbon atom and selected from cyano, C₁₋₃ alkyl, C₂₋₃ alkenyl, C₂₋₃ alkynyl, C₃₋₆ cycloalkyl, C₂₋₃ alkoxyalkyl, C₁₋₃ alkoxy, C₂₋₃ alkylcarbonyl, C₂₋₃ alkoxycarbonyl, C₂₋₃ alkylaminoalkyl and dialkylaminoalkyl C₃₋₄ in the annular members of the nitrogen atom; Q² is a phenyl ring or a naphthalenyl ring system, each ring or ring system optionally substituted with up to 5 substituents independently selected from R³ᵃ and R³ᵇ; or a fully unsaturated 5 to 6 membered heterocyclic ring or an 8 to 10 membered heteroaromatic bicyclic ring system, each ring or ring system contains annular members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O atoms, up to 2 atoms of S and up to 4 atoms of N, where up to 3 annular carbon members are independently selected from C (= O) and C (= S), and the annular members of the sulfur atom are independently selected from S ( = O) ᵘ (= NR²⁷) ᵛ, each ring or ring system optionally substituted with up to 5 substituents independently selected from R³ᵃ and R³ᵇ on the annular members of the carbon atom and selected from cyano, C₁₋₃ alkyl, C₂₋₃ alkenyl, C₂₋₃ alkynyl, C₃₋₆ cycloalkyl, C₂₋₃ alkoxyalkyl, C₁₋₃ alkoxy, C₂₋₃ alkylcarbonyl, C₂₋₃ alkoxycarbonyl, C₂₋₃ alkylaminoalkyl and dialkylaminoalkyl C₃₋₄ in the annular members of the nitrogen atom; X is O, S (= O) ₘ, NR⁴ or CR⁵ᵃOR⁵ᵇ; R¹ is H, cyano, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, C₂₋₆ alkoxyalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy ₌O₎OR⁶ or C (= O) NR⁷R⁸; R¹ᵃ is H; or R¹ᵃ and R¹ are taken together with the carbon atom to which they are attached to form a cyclopropyl ring optionally substituted with up to 2 substituents independently selected from halogen and methyl; R² is H, cyano, halogen, C₁₋₃ alkyl, C₂₋₃ alkenyl, C₂₋₃ alkynyl, C₁₋₃ haloalkyl, C₂₋₃ haloalkenyl, C₂₋₃ cyanoalkyl, C₁₋₃ hydroxyalkyl, C₁₋₃ alkoxy or C₁ alkylthio ₋₃ or cyclopropyl optionally substituted with up to 2 substituents independently selected from halogen and methyl; each R³ᵃ is independently cyano, halogen, hydroxy, nitro, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, C₃₋₄ cycloalkyl, C₃₋₇ halocycloalkyl, C₄₋₆ cycloalkylalkyl, C₄₋ alkylcycloalkyl ₆, Cilt alkylthio, C₁₋₃ haloalkylthio, C₁₋₃ alkylsulfinyl, C₁₋₃ haloalkylsulfinyl, C₁₋₃ alkylsulfonyl, C₁₋₃ haloalkylsulfonyl, C₁₋₃ alkoxy, C₁₋₃ haloalkoxy, C₃₋₇ alkylsulfonyloxy ₂, C halo haloalkylsulfonyloxy, C₂₋₃ alkylcarbonyloxy, C₂₋₃ alkylcarbonyl, amino, methylamino, C₂₋₄ dialkylamino, C₂₋₃ alkylcarbonylamino, -CH (= O), -NHCH (= O), -SF₅, -SCºN , -C (= S) NR⁹ᵃR⁹ᵇ or -UVT; each R³ᵇ is independently C₅₋₈ alkyl, C₅₋₈ haloalkyl, C₅₋₈ alkenyl, C₅₋₈ alkynyl, C₂₋₈ haloalkenyl, C₁₋₈ nitroalkyl, C₂₋₈ nitroalkenyl, C₅₋₈ cycloalkyl, alkylcycloalkyl C₇₋₈, C₇₋₈ cycloalkylalkyl, C₅₋₁₂ cycloalkylalkyl, C₅₋₁₂ cycloalkylalkyl, C₄₋₈ alkylthio, C halo haloalkylthio, C₄₋₈ alkylsulfinyl, C₄₋₈ haloalkylsulfinyl, C₄₋₈ alkylsulfonyl, haloalkylsulfonyl C₄₋₈, C₄₋₈ alkoxy, C₅₋₈ haloalkoxy, C₂₋₈ alkenyloxy, C₂₋₈ haloalkyloxy, C₃₋₈ haloyloxy, C₂₋₈ cyanoalkoxy, C₈₋₁₂ cycloalkoxy, C₃₋₁₂ halocycloalkoxy, cycloalkylalkoxy C₄₋₁₂, C₅₋₁₂ cycloalkylalkenyloxy, C₅₋₁₂ cycloalkylalkyloxy, C₃₋₈ alkylsulfonyloxy, C₃₋₈ haloalkylsulfonyloxy, alkyl C₄₋₈ aryloxy, C₄₋₈ alkylcarbonyl, C₂₋₈ alkylamino, C₄₋₈ alkylcarbonylamino, C₃₋₁₂ trialkylsilyl, C₄₋₁₂ trialkylsilylalkyl, C₄₋₁₂ trialkylsilylalkoxy, -C (= NR⁹ᵃ) NR⁹ᵃOR⁹ᵃ, -CR¹⁰ᵃ = NOR¹⁰ᵇ, -CR¹⁰ᶜ = NNR⁹ᵃR⁹ᵇ, -NR⁹ᵃN = CR¹¹ᵃR¹¹ᵇ or -ON = CR¹¹ᵃR¹¹ᵇ; or each R³ᵇ is independently -A (CR¹²ᵃR¹²ᵇ) ₙW; each A is independently O or a direct link; each W is independently a 3- to 7-membered heterocyclic ring containing ring members selected from carbon atoms and 1 to 4 heteroatoms independently selected from up to 2 O atoms, up to 2 S atoms and up to 4 N atoms, where up to 3 annular members of the carbon atom are independently selected from C (= O) and C (= S), the ring optionally substituted with up to 3 substituents independently selected from R¹³ on the annular members of the carbon atom and R¹⁴ on the annular members of the nitrogen atom; R⁴ is H, amino, C₂₋₆ alkenyl, C₃₋₆ alkynyl, C₃₋₆ cycloalkyl, -CH (= O), -S (= O) ₂OM, -S (= O) ₘR¹⁵, - (C = Z) R¹⁶ or OR¹⁷; or C₁₋₆ alkyl or C₁₋₆ haloalkyl, each optionally substituted with up to 2 substituents independently selected from R¹⁸; R⁵ᵃ is H or C₁₋₆ alkyl; R⁵ᵇ is H, -CH (= O), C₁₋₆ alkyl, C₂₋₆ alkenyl, C₃₋₆ alkynyl, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₃₋₆ halocycloalkyl, C₂₋₆ alkoxyalkyl, C₂₋ cyanoalkyl ₆, C₂₋₆ alkylcarbonyl, C₂₋₆ alkoxycarbonyl, (C-alkylthio) carbonyl, C₄₋₈ cycloalkylcarbonyl, C₄₋₈ cycloalkoxycarbonyl, (C₄₋₈ cycloalkylthio) carbonyl, C₂₋₆ alkoxy (thiocarbonyl) or cycloalkoxy (thiocarbonyl) C₄₋₈; R⁶ is H, C₁₋₆ alkyl or C₁₋₆ haloalkyl; R⁷ and R⁸ are each independently H, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₆ cycloalkyl, C₄₋₈ cycloalkylalkyl or C₄₋₈ alkylcycloalkyl; or R⁷ and R⁸ are taken together with e

ARP140100538A 2013-02-20 2014-02-20 FUNGICIDE PIRAZOLS AR094840A1 (en)

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