AR105360A1 - Hidrazidas de ácido carboxílico heteroarilo sustituidas o sus sales y su uso para aumentar la tolerancia al estrés en plantas - Google Patents

Hidrazidas de ácido carboxílico heteroarilo sustituidas o sus sales y su uso para aumentar la tolerancia al estrés en plantas

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AR105360A1
AR105360A1 ARP160102142A ARP160102142A AR105360A1 AR 105360 A1 AR105360 A1 AR 105360A1 AR P160102142 A ARP160102142 A AR P160102142A AR P160102142 A ARP160102142 A AR P160102142A AR 105360 A1 AR105360 A1 AR 105360A1
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Argentina
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alkyl
aryl
heteroaryl
alkoxycarbonyl
cycloalkyl
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ARP160102142A
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Desbordes Philippe
Schmutzler Dirk
Dittgen Jan
Mosrin Marc
Tiebes Jrg
Brchner Peter
Lehr Stefan
Helmke Hendrik
Brnjes Marco
Bojack Guido
Franckenpohl Jens
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Bayer Cropscience Ag
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Publication of AR105360A1 publication Critical patent/AR105360A1/es

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    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/82—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 five-membered rings with three ring hetero atoms
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    • C07D231/14—Heterocyclic 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
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    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Para aumentar la tolerancia al estrés abiótico, así como para aumentar el crecimiento de las plantas y/o para aumentar el rendimiento de la planta. Reivindicación 1: Hidrazidas de ácido carboxílico heteroarilo sustituidas de la formula general (1) o sales de los mismos, donde R¹, R² y R⁷ son independientemente hidrógeno, halógeno, ciano, nitro, NR²¹R²², OR²³, S(O)ₙR²⁴, tiocianato, isotiocianato, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, pentafluortio, C₁₋₈-alcoxi-C₁₋₈-haloalquilo, C₁₋₈-haloalcoxi-C₁₋₈-haloalquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₄₋₁₀-cicloalquenilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, C₁₋₈-alquilcarbonilo-C₁₋₈-alquilo, COOR²³, CONR²¹R²², COR²³, -C=NOR²³, R²¹R²²N-C₁₋₈-alquilo, R²³OOC-C₁₋₈-alquilo, arilo-C₁₋₈-alquinilo, heteroarilo-C₁₋₈-alquinilo, heterociclilo-C₁₋₈-alquinilo, tris-[C₁₋₈-alquilo]sililC₂₋₈-alquinilo, bis-[C₁₋₈-alquilo](aril)sililC₂₋₈-alquinilo, bis-aril[C₁₋₈-alquilo]sililC₂₋₈-alquinilo, C₃₋₈-cicloalquilo-C₂₋₈-alquinilo, arilo-C₂₋₈-alquenilo, heteroarilo-C₂₋₈-alquenilo, heterociclilo-C₂₋₈-alquenilo, C₃₋₈-cicloalquilo-C₂₋₈-alquenilo, C₁₋₈-alcoxi-C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquilaminosulfonilamino, C₃₋₈-cicloalquilamino sulfonilamino, diazo, diazo arilo, tris-[C₁₋₈-alquilo]sililo, bis-[C₁₋₈-alquilo](aril)silil, bis-aril[C₁₋₈-alquilo]silil; X¹, X² y X³ son iguales o diferentes y representan independientemente O (oxígeno), S (azufre), N (nitrógeno), la agrupación C-R² o la agrupación N-R²⁰, sin embargo en ningún caso un átomo O y un átomo S son adyacentes y en ningún caso uno o mas átomos O ó átomos S está contenido en el anillo formado de 5 miembros y donde R² en la agrupación C-R² y R²⁰ en la agrupación N-R²⁰ tienen significados idénticos o diferentes según se define anteriormente o a continuación; W es O (oxígeno) o S (azufre); A¹, A², A³, A⁴ y A⁵ son iguales o diferentes y representan independientemente N (nitrógeno) o la agrupación C-R⁷, sin embargo en ningún caso más de dos átomos N son adyacentes, y en el que R⁷ en la agrupación C-R⁷ tiene los mismos o diferentes significados respectivamente según la definición anterior; R³ representa C₁₋₈-alquilo, ciano-C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, R²¹R²²N-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alcoxi-C₁₋₈-alquilo; R⁴ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, C₁₋₈-alquilamino-C₁₋₈-alquilo, bis-[C₁₋₈-alquilo]amino-C₁₋₈-alquilo, C₃₋₈-cicloalquilamino-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alcoxi-C₁₋₈-alquilo, COR²³, C₁₋₈-alcoxicarbonilo, C₂₋₈-alqueniloxicarbonilo, C₂₋₈-alquiniloxicarbonilo, arilo-C₁₋₈-alcoxicarbonilo, heteroarilo-C₁₋₈-alcoxicarbonilo, C₃₋₈-cicloalquilo-C₁₋₈-alcoxicarbonilo, CONR²¹R²², SO₂R²⁴, hidroxicarbonilo-C₁₋₈-alquilo, C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, C₂₋₈-alqueniloxicarbonilo-C₁₋₈-alquilo, C₂₋₈-alquiniloxicarbonilo-C₁₋₈-alquilo, arilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, heteroarilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, heterociclilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, C₁₋₈-alquilcarbonilo-C₁₋₈-alquilo, C₁₋₈-alquilsulfonilo-C₁₋₈-alquilo, C₁₋₈-alquilsulfinilo-C₁₋₈-alquilo; R⁵ y R⁶ representan independientemente hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, COOR²³, CONR²¹R²², hidroxicarbonilo-C₁₋₈-alquilo, C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, C₂₋₈-alqueniloxicarbonilo-C₁₋₈-alquilo, C₂₋₈-alquiniloxicarbonilo-C₁₋₈-alquilo, arilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, heteroarilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, heterociclilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo; R³ y R⁴ junto con el átomo de nitrógeno al que están unidos forman un anillo de 3 a 7 miembros totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos y opcionalmente adicionalmente sustituido; R¹ y X¹, si X¹ representa un grupo C-R², forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; X¹ y X², si ambos representan un grupo C-R², forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; A¹ y A², si ambos representan un grupo C-R⁷, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; A² y A³, si ambos representan un grupo C-R⁷, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; y A³ y A⁴, si ambos representan un grupo C-R⁷, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; Y es un enlace o representa los grupos Y-1 a Y-7 del grupo de fórmulas (2), en el que R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸ y R¹⁹ tiene cada uno el significado que se define a continuación y en el que la flecha representa un enlace del anillo de 6 miembros con los grupos A¹, A², A³, A⁴ y A⁵; R⁸ R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ R¹⁶, R¹⁷ R¹⁸ y R¹⁹ representan independientemente hidrógeno, halógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, COOR²³; R⁵ y R⁶ junto con el átomo al que están unidos forman un anillo de 5 a 7 miembros totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos y opcionalmente adicionalmente sustituido; R²⁰ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₄₋₁₀-cicloalquenilo, C₁₋₈-alcoxi, arilo, heteroarilo, heterociclilo, C₁₋₈-alquilcarbonilo, arilo-C₁₋₈-alquilcarbonilo, C₃₋₈-cicloalquilcarbonilo, arilcarbonilo, heteroarilcarbonilo, C₁₋₈-alcoxicarbonilo, C₂₋₈-alqueniloxicarbonilo, arilo-C₁₋₈-alcoxicarbonilo, heteroarilo-C₁₋₈-alcoxicarbonilo, C₃₋₈-cicloalquilo-C₁₋₈-alcoxicarbonilo, C₁₋₈-alquilsulfonilo, C₁₋₈-haloalquilsulfonilo, arilsulfonilo, heteroarilsulfonilo, C₃₋₈-cicloalquilsulfonilo, C₁₋₈-alquilsulfinilo, arilsulfinilo, heteroarilsulfinilo, C₃₋₈-cicloalquilsulfinilo; n es 0, 1 ó 2; R²¹ y R²² son iguales o diferentes y representan independientemente hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₈-cianoalquilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-haloalquilo arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₄₋₁₀-cicloalquenilo-C₁₋₈-alquilo, COR²³, SO₂-R²⁴, C₁₋₈-alquilo-HNO₂S-, C₃₋₈-cicloalquilo-HNO₂S-, heterociclilo, C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, C₁₋₈-alcoxicarbonilo, arilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, arilo-C₁₋₈-alcoxicarbonilo, heteroarilo-C₁₋₈-alcoxicarbonilo, C₂₋₈-alqueniloxicarbonilo, C₂₋₈-alquiniloxicarbonilo, heterociclilo-C₁₋₈-alquilo; R²³ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₈-cianoalquilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-haloalquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₄₋₁₀-cicloalquenilo-C₁₋₈-alquilo, C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo,C₂₋₈-alqueniloxicarbonilo-C₁₋₈-alquilo, arilo-C₁₋₈-alcoxicarbonilo-C₁₋₈-alquilo, hidroxicarbonilo-C₁₋₈-alquilo, heterociclilo, heterociclilo-C₁₋₈-alquilo; y R²⁴ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo, C₁₋₈-cianoalquilo, C₁₋₁₀-haloalquilo, C₂₋₈-haloalquenilo, C₂₋₈-haloalquinilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, C₁₋₈-alcoxi-C₁₋₈-alquilo, C₁₋₈-alcoxi-C₁₋₈-haloalquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, heterociclilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₄₋₁₀-cicloalquenilo-C₁₋₈-alquilo, NR²¹R²².
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