AR090098A1 - FUNGICIDE PIRAZOLS - Google Patents

FUNGICIDE PIRAZOLS

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Publication number
AR090098A1
AR090098A1 ARP130100510A ARP130100510A AR090098A1 AR 090098 A1 AR090098 A1 AR 090098A1 AR P130100510 A ARP130100510 A AR P130100510A AR P130100510 A ARP130100510 A AR P130100510A AR 090098 A1 AR090098 A1 AR 090098A1
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Argentina
Prior art keywords
ring
alkyl
haloalkyl
independently selected
optionally substituted
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ARP130100510A
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Spanish (es)
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Keith Long Jeffrey
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Du Pont
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Publication of AR090098A1 publication Critical patent/AR090098A1/en

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18One oxygen or sulfur atom
    • C07D231/20One oxygen atom attached in position 3 or 5
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond

Abstract

Se describen composiciones que contienen los compuestos de la fórmula (1) 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 la presente. Reivindicación 1: Un compuesto seleccionado de la fórmula (1), N-óxidos y sales de estos, caracterizado porque Q¹ es un anillo o sistema anular de fenilo o naftalenilo; cada anillo o sistema anular está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R³; o un anillo heterocíclico de 5 a 6 miembros totalmente insaturado o un sistema anular bicíclico heteroaromático de 8 a 10 miembros; cada anillo o sistema anular contiene miembros de anillo seleccionados de átomos de carbono y hasta 4 heteroátomos seleccionados independientemente de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros de anillo de carbono se seleccionan independientemente de C(=O) y C(=S) y los miembros de anillo de átomos de azufre se seleccionan independientemente de S(=O)ᵘ(=NR¹⁴)ᵛ; cada anillo o sistema anular está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R³ en miembros de anillo de átomos de carbono y seleccionados de ciano, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alcoxi C₁₋₆, alcoxialquilo C₂₋₆, alquilcarbonilo C₂₋₆, alcoxicarbonilo C₂₋₆, alquilaminoalquilo C₂₋₆ y dialquilaminoalquilo C₃₋₆ en miembros de anillo de átomos de nitrógeno; Q² es un anillo o sistema anular de fenilo o naftalenilo; cada anillo o sistema anular está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R³; o un anillo heterocíclico de 4, 5 ó 6 miembros saturado, parcialmente insaturado o totalmente insaturado o un sistema anular bicíclico heteroaromático de 8 a 10 miembros; cada anillo o sistema anular contiene miembros de anillo seleccionados de átomos de carbono y hasta 4 heteroátomos seleccionados independientemente de hasta 2 átomos de O, hasta 2 átomos de S y hasta 4 átomos de N, en donde hasta 3 miembros de anillo de carbono se seleccionan independientemente de C(=O) y C(=S), y los miembros de anillo de átomos de azufre se seleccionan independientemente de S(=O)ᵘ(=NR¹⁴)ᵛ; cada anillo o sistema anular está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R³ en miembros de anillo de átomos de carbono y seleccionados de ciano, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₆, alcoxi C₁₋₆, alcoxialquilo C₂₋₆, alquilcarbonilo C₂₋₆, alcoxicarbonilo C₂₋₆, alquilaminoalquilo C₂₋₆ y dialquilaminoalquilo C₃₋₆ en miembros de anillo de átomos de nitrógeno; o alquilo C₁₋₁₂, alquenilo C₂₋₁₂, alquinilo C₂₋₁₂, cicloalquilo C₃₋₁₂ o cicloalquenilo C₃₋₁₂; cada uno está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de R³; X es O, NR⁴ o CR¹⁵R¹⁶; R¹ es H, halógeno, alquilo C₁₋₆, haloalquilo C₁₋₆, alquenilo C₂₋₄, alquinilo C₂₋₄, cicloalquilo C₃₋₇, CO₂R⁵, C(O)NR⁶R⁷, ciano, alcoxi C₁₋₆, haloalcoxi C₁₋₆ o alcoxialquilo C₂₋₅; o R¹ es fenilo sustituido opcionalmente con hasta 3 R⁸; o un heterociclo aromático de cinco o seis miembros que contiene nitrógeno sustituido opcionalmente con hasta 3 sustituyentes seleccionados independientemente de R⁹ᵃ en miembros de anillo de átomos de carbono y R⁹ᵇ en miembros de anillo de átomos de nitrógeno; 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, alquenilo C₂₋₃ o alquinilo C₂₋₃; cada R³ se selecciona independientemente de halógeno, ciano, nitro, amino, metilamino, dimetilamino, formilamino, alquilcarbonilamino C₂₋₃, alquilo C₁₋₄, haloalquilo C₁₋₄, alcoxi C₁₋₃, haloalcoxi C₁₋₃, alquiltio C₁₋₃, haloalquiltio C₁₋₃, alquilsulfinilo C₁₋₃, haloalquilsulfinilo C₁₋₃, alquilsulfonilo C₁₋₃, haloalquilsulfonilo C₁₋₃, alquilsulfoniloxi C₁₋₂, haloalquilsulfoniloxi C₁₋₂, cicloalquilo C₃₋₄, cicloalcoxi C₃₋₇, alquilcicloalquilo C₄₋₆, cicloalquilalquilo C₄₋₆, halocicloalquilo C₃₋₇, alquenilo C₂₋₄, alquinilo C₂₋₄, hidroxi, formilo, alquilcarbonilo C₂₋₃, alquilcarboniloxi C₂₋₃, -SF₅, -SCN, C(=S)NR¹⁹R²⁰, C(=NOR²⁷)R²⁸ o -U-V-T; R⁴ es H, formilo, alquenilo C₂₋₅, alquinilo C₃₋₅, cicloalquilo C₃₋₇, -SO₃⁻M⁺, -S(=O)ₜR¹⁰, -(C=W)R¹¹, NH₂ o OR²¹; o alquilo C₁₋₆ o haloalquilo C₁₋₆; cada uno está sustituido opcionalmente con hasta 2 R¹²; R⁵ es H, alquilo C₁₋₆ o haloalquilo C₁₋₆; R⁶ y R⁷ se seleccionan independientemente de H, alquilo C₁₋₆, haloalquilo C₁₋₆, cicloalquilo C₃₋₇, cicloalquilalquilo C₄₋₈ y alquilcicloalquilo C₄₋₈; o R⁶ y R⁷ se toman junto con el átomo de nitrógeno al cual están conectados para formar un anillo heterocíclico no aromático de cuatro a siete miembros que contiene miembros de anillo, además del átomo de nitrógeno del anillo conector, seleccionados de átomos de carbono y, opcionalmente, hasta un miembro de anillo seleccionado de O, S(O)ₙ y NR¹³; cada R⁸, R⁹ᵃ y R⁹ᵇ se selecciona independientemente de halógeno, alquilo C₁₋₂, haloalquilo C₁₋₂, alcoxi C₁₋₂, haloalcoxi C₁₋₂, ciano, nitro, SCH₃, S(O)CH₃ y S(O)₂CH₃; R¹⁰ es alquilo C₁₋₆ o haloalquilo C₁₋₆; cada R¹¹ es independientemente alquilo C₁₋₆, alcoxi C₁₋₆, alcoxialquilo C₂₋₇, alquilaminoalquilo C₂₋₇, dialquilaminoalquilo C₂₋₈, alquiltio C₁₋₆ o alquiltioalquilo C₂₋₇; cada R¹² es independientemente cicloalquilo C₃₋₇, alcoxi C₁₋₄, haloalcoxi C₁₋₄, alquiltio C₁₋₄, alquilsulfinilo C₁₋₄, alquilsulfonilo C₁₋₄ o ciano; R¹³ es H, alquilo C₁₋₃ o haloalquilo C₂₋₃; cada R¹⁴ es independientemente H, ciano, alquilo C₁₋₃ o haloalquilo C₁₋₃; R¹⁵ es H o alquilo C₁₋₄; R¹⁶ es F, Cl o OR¹⁸; cada R¹⁸ es independientemente H, formilo, cicloalquilo C₃₋₇, -SO₃⁻M⁺ o -(C=W)R¹¹; o alquilo C₁₋₆ o haloalquilo C₁₋₆ cada uno está sustituido opcionalmente con hasta 2 R¹²; cada R¹⁹ y R²⁰ es independientemente H o CH₃; R²¹ es H, formilo, cicloalquilo C₃₋₇, -SO₃⁻M⁺ o -(C=W)R¹¹; o alquilo C₁₋₆ o haloalquilo C₁₋₆; cada uno está sustituido opcionalmente con hasta 2 R¹²; cada U es independientemente O, S(=O)ʷ, NR²² o un enlace directo; cada V es independientemente alquileno C₁₋₆, alquenileno C₂₋₆, alquinileno C₃₋₆, cicloalquileno C₃₋₆ o cicloalquenileno C₃₋₆, en donde hasta 3 átomos de carbono se seleccionan independientemente de C(=O); cada uno está sustituido opcionalmente con hasta 5 sustituyentes seleccionados independientemente de halógeno, ciano, nitro, hidroxi, alquilo C₁₋₆, haloalquilo C₁₋₆, alcoxi C₁₋₆ y haloalcoxi C₁₋₆; cada T es independientemente ciano, NR²³ᵃR²³ᵇ, OR²⁴ o S(=O)ʸR²⁵; cada R²² es independientemente H, alquilo C₁₋₆, haloalquilo C₁₋₆, alquilcarbonilo C₂₋₆, alcoxicarbonilo C₂₋₆, (alquiltio)carbonilo C₂₋₆, alcoxi(tiocarbonilo) C₂₋₆, cicloalquilcarbonilo C₄₋₈, cicloalcoxicarbonilo C₄₋₈, (cicloalquiltio)carbonilo C₄₋₈ o cicloalcoxi(tiocarbonilo) C₄₋₈; cada R²³ᵃ y R²³ᵇ es independCompositions containing the compounds of the formula (1) 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 the present. Claim 1: A compound selected from the formula (1), N-oxides and salts thereof, characterized in that Q¹ is an annular ring or system of phenyl or naphthalenyl; each ring or annular system is optionally substituted with up to 5 substituents independently selected from R³; 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 selected ring members of carbon atoms and up 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 carbon ring members are selected independently of C (= O) and C (= S) and the ring members of sulfur atoms are independently selected from S (= O) ᵘ (= NR¹⁴) ᵛ; Each ring or annular system is optionally substituted with up to 5 substituents independently selected from R³ in ring members of carbon atoms and selected from cyano, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, alkoxy C₁₋₆, C₂₋₆ alkoxyalkyl, C₂₋₆ alkylcarbonyl, C₂₋₆ alkoxycarbonyl, C₂₋₆ alkylaminoalkyl and C₃₋₆ dialkylaminoalkyl in ring members of nitrogen atoms; Q² is a ring or ring system of phenyl or naphthalenyl; each ring or annular system is optionally substituted with up to 5 substituents independently selected from R³; or a saturated, partially unsaturated or totally unsaturated 4, 5 or 6 membered heterocyclic ring or an 8 to 10 membered heteroaromatic bicyclic ring system; Each ring or ring system contains selected ring members of carbon atoms and up 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 carbon ring members are selected independently of C (= O) and C (= S), and the ring members of sulfur atoms are independently selected from S (= O) ᵘ (= NR¹⁴) ᵛ; Each ring or annular system is optionally substituted with up to 5 substituents independently selected from R³ in ring members of carbon atoms and selected from cyano, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₂₋₆ alkynyl, C₃₋₆ cycloalkyl, alkoxy C₁₋₆, C₂₋₆ alkoxyalkyl, C₂₋₆ alkylcarbonyl, C₂₋₆ alkoxycarbonyl, C₂₋₆ alkylaminoalkyl and C₃₋₆ dialkylaminoalkyl in ring members of nitrogen atoms; or C₁₋₁₂ alkyl, C₂₋₁₂ alkenyl, C₂₋₁₂ alkynyl, C₃₋₁₂ cycloalkyl or C₃₋₁₂ cycloalkenyl; each is optionally substituted with up to 5 substituents independently selected from R³; X is O, NR⁴ or CR¹⁵R¹⁶; R¹ is H, halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, C₃₋₇ cycloalkyl, CO₂R⁵, C (O) NR⁶R⁷, cyano, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy or C₂₋₅ alkoxyalkyl; or R¹ is phenyl optionally substituted with up to 3 R⁸; or a five or six membered aromatic heterocycle containing nitrogen optionally substituted with up to 3 substituents independently selected from R⁹ᵃ in ring members of carbon atoms and R⁹ᵇ in ring members of nitrogen atoms; 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, C₂₋₃ alkenyl or C₂₋₃ alkynyl; each R³ is independently selected from halogen, cyano, nitro, amino, methylamino, dimethylamino, formylamino, C₂₋₃ alkylcarbonylamino, C₁₋₄ alkyl, C₁₋₄ haloalkyl, C₁₋₃ alkoxy, C₁₋₃ haloalkoxy, C₁₋₃ alkylthio, C₁₋₃ haloalkylthio, C₁₋₃ alkylsulfinyl, C₁₋₃ haloalkylsulfinyl, C₁₋₃ alkylsulfonyl, C₁₋₃ haloalkylsulfonyl, C₁₋₂ alkylsulfonyloxy, C₁₋₂ haloalkylsulfonyloxy, C ciclo cycloalkoxy, C₄₋₆ alkylcycloalkyl, C₄₋₆ cycloalkylalkyl, C₃₋₇ halocycloalkyl, C₂₋₄ alkenyl, C₂₋₄ alkynyl, hydroxy, formyl, C₂₋₃ alkylcarbonyl, C₂₋₃ alkylcarbonyloxy, -SF₅, -SCN, C (= S) NR¹⁹R²⁰, C (= NOR²⁷) R²⁸ or -UVT; R⁴ is H, formyl, C₂₋₅ alkenyl, C₃₋₅ alkynyl, C₃₋₇ cycloalkyl, -SO₃⁻M⁺, -S (= O) ₜR¹⁰, - (C = W) R¹¹, NH₂ or OR²¹; or C₁₋₆ alkyl or C₁₋₆ haloalkyl; each is optionally substituted with up to 2 R¹²; R⁵ is H, C₁₋₆ alkyl or C₁₋₆ haloalkyl; R⁶ and R⁷ are independently selected from H, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₃₋₇ cycloalkyl, C₄₋₈ cycloalkylalkyl and C₄₋₈ alkylcycloalkyl; or R⁶ and R⁷ are taken together with the nitrogen atom to which they are connected to form a four to seven membered non-aromatic heterocyclic ring containing ring members, in addition to the nitrogen atom of the linker ring, selected from carbon atoms and, optionally, up to a ring member selected from O, S (O) ₙ and NR¹³; each R⁸, R⁹ᵃ and R⁹ᵇ is independently selected from halogen, C₁₋₂ alkyl, C₁₋₂ haloalkyl, C₁₋₂ alkoxy, C₁₋₂ haloalkoxy, cyano, nitro, SCH₃, S (O) CH₃ and S (O) ₂CH₃; R¹⁰ is C₁₋₆ alkyl or C₁₋₆ haloalkyl; each R¹¹ is independently C₁₋₆ alkyl, C₁₋₆ alkoxy, C₂₋₇ alkoxyalkyl, C₂₋₇ alkylaminoalkyl, C₂₋₈ dialkylaminoalkyl, C₁₋₆ alkylthio or C₂₋₇ alkylthioalkyl; each R¹² is independently C₃₋₇ cycloalkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkoxy, C₁₋₄ alkylthio, C₁₋₄ alkylsulfinyl, C₁₋₄ alkylsulfonyl or cyano; R¹³ is H, C₁₋₃ alkyl or C₂₋₃ haloalkyl; each R¹⁴ is independently H, cyano, C₁₋₃ alkyl or C₁₋₃ haloalkyl; R¹⁵ is H or C₁₋₄ alkyl; R¹⁶ is F, Cl or OR¹⁸; each R¹⁸ is independently H, formyl, C₃₋₇ cycloalkyl, -SO₃⁻M⁺ or - (C = W) R¹¹; or C₁₋₆ alkyl or C₁₋₆ haloalkyl each is optionally substituted with up to 2 R¹²; each R¹⁹ and R²⁰ is independently H or CH₃; R²¹ is H, formyl, C₃₋₇ cycloalkyl, -SO₃⁻M⁺ or - (C = W) R¹¹; or C₁₋₆ alkyl or C₁₋₆ haloalkyl; each is optionally substituted with up to 2 R¹²; each U is independently O, S (= O) ʷ, NR²² or a direct link; each V is independently C₁₋₆ alkylene, C₂₋₆ alkenylene, C₃₋₆ alkynylene, C₃₋₆ cycloalkylene or C₃₋₆ cycloalkenylene, wherein up to 3 carbon atoms are independently selected from C (= O); each is optionally substituted with up to 5 substituents independently selected from halogen, cyano, nitro, hydroxy, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy and C₁₋₆ haloalkoxy; each T is independently cyano, NR²³ᵃR²³ᵇ, OR²⁴ or S (= O) ʸR²⁵; each R²² is independently H, C alquilo alkyl, C₁₋₆ haloalkyl, C₂₋₆ alkylcarbonyl, C₂₋₆ alkoxycarbonyl, C₂₋₆ (alkylthio) carbonyl, C₂₋₆ alkoxy (thiocarbonyl), C₄₋₈ cycloalkylcarbonyl, C₄₋ cycloalkoxycarbonyl ₈, (C-cycloalkylthio) carbonyl or C₄₋₈-cycloalkoxy (thiocarbonyl); each R²³ᵃ and R²³ᵇ is independent

ARP130100510A 2012-02-20 2013-02-19 FUNGICIDE PIRAZOLS AR090098A1 (en)

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