AR105324A1 - Hidrazidas de ácido carboxílico arilo y heteroarilo cíclicas sustituidas o sus sales y su uso para aumentar la tolerancia al estrés en plantas - Google Patents

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

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AR105324A1
AR105324A1 ARP160102038A ARP160102038A AR105324A1 AR 105324 A1 AR105324 A1 AR 105324A1 AR P160102038 A ARP160102038 A AR P160102038A AR P160102038 A ARP160102038 A AR P160102038A AR 105324 A1 AR105324 A1 AR 105324A1
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Argentina
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alkyl
aryl
heteroaryl
cycloalkyl
heterocyclyl
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ARP160102038A
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Inventor
Pedro Ruiz-Santaella Moreno Juan
Heinemann Ines
Schmutzler Dirk
Jeffrey Hills Martin
Bickers Udo
Dittgen Jan
Adelt Isabelle
Lehr Stefan
Helmke Hendrik
Brnjes Marco
Bojack Guido
Franckenpohl Jens
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Bayer Cropscience Ag
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Publication of AR105324A1 publication Critical patent/AR105324A1/es

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Abstract

La presente solicitud se refiere a hidrazidas de ácido carboxílico arilo y heteroarilo cíclicas sustituidas 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 arilo y heteroarilo cíclicas sustituidas de la fórmula general (1) o sales de los mismos, donde R¹, R² y R³⁸ representan independientemente hidrógeno, halógeno, ciano, nitro, NR³⁹R⁴⁰, OR⁴¹, S(O)ₙR⁴², 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, COOR⁴², CONR³⁹R⁴⁰, COR⁴¹, -C=NOR⁴¹, R⁴¹OOC-C₁₋₈-alquilo, arilo-C₁₋₈-alquinilo, heteroarilo-C₁₋₈-alquinilo, heterociclilo-C₁₋₈-alquinilo, tris-[C₁₋₈-alquilo]sililo-C₂₋₈-alquinilo, bis-[C₁₋₈-alquilo](arilo)sililo-C₂₋₈-alquinilo, bis-arilo[C₁₋₈-alquilo]sililo-C₂₋₈-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-alquilamino sulfonilamino, C₃₋₈-cicloalquilamino sulfonilamino, diazo, diazo arilo, tris-[C₁₋₈-alquilo]sililo, bis-[C₁₋₈-alquilo](arilo)sililo, bis-arilo[C₁₋₈-alquilo]sililo; X¹, X², X³ y X⁴ son iguales o diferentes y representan independientemente N (nitrógeno) o la agrupación C-R², sin embargo en ningún caso más de dos átomos N son adyacentes, y en el que R² en la agrupación C-R² tiene los mismos o diferentes significados respectivamente según se define a continuación, y en el que R¹ y R² no son simultáneamente hidrógeno si X¹, X², X³ y X⁴ representan C-R²; 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-R³⁸, sin embargo en ningún caso más de dos átomos N son adyacentes, y en el que R³⁸ en la agrupación C-R³⁸ tiene los mismos o diferentes significados respectivamente según la definición anterior; Q junto con el grupo CR³R⁴ y el átomo de nitrógeno al que están unidos forman un anillo de 3 - 7 miembros totalmente saturado, parcialmente saturado o totalmente insaturado, opcionalmente interrumpido por heteroátomos y además opcionalmente sustituido y además representa a los grupos Q-1 a Q-15 del grupo de fórmulas (2) en el que R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, R²⁰, R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹, R³², R³³, R³⁴, R³⁵, R³⁶ y R³⁷ tiene cada uno el significado según las siguientes definiciones y donde la flecha representa un enlace con el átomo-N del grupo hidrazida; R³, R⁴, R¹⁷, R¹⁸, R¹⁹ y R²⁰ representan independientemente hidrógeno, C₁₋₈-alquilo, halógeno, NR³⁹R⁴⁰, S(O)ₙR⁴², ciano, nitro, ciano-C₁₋₈-alquilo, C₃₋₁₀-cicloalquilo, C₃₋₁₀-halocicloalquilo, C₄₋₁₀-cicloalquenilo, C₄₋₁₀-halocicloalquenilo, C₁₋₁₀-haloalquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₂₋₈-haloalquinilo, C₂₋₈-alquinilo, C₂₋₈-alquenilo, C₂₋₈-haloalquenilo, heterociclilo, heterociclilo-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, COR⁴¹, COOR⁴¹, CONR³⁹R⁴⁰, 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, C₁₋₈-alquilcarbonilo-C₁₋₈-alquilo o junto al átomo al que están unidos forman un grupo oxo; 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, COOR⁴¹, CONR³⁹R⁴⁰, 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; R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, R³⁰, R³¹, R³², R³³, R³⁴, R³⁵ y R³⁶ representan independientemente hidrógeno, ciano, nitro, halógeno, hidroxi, C₁₋₈-alquilo, C₁₋₈-alcoxi, C₁₋₈-alquiltio, C₁₋₈-haloalcoxi, C₁₋₈-haloalquiltio, C₃₋₁₀-cicloalquilo, C₁₋₁₀-haloalquilo, arilo, arilo-C₁₋₈-alquilo, heteroarilo, heteroarilo-C₁₋₈-alquilo, C₃₋₈-cicloalquilo-C₁₋₈-alquilo, C₂₋₈-haloalquinilo, C₂₋₈-alquinilo, C₂₋₈-alquenilo, C₂₋₈-haloalquenilo, heterociclilo, heterociclilo-C₁₋₈-alquilo, C₁₋₈-alquiltio-C₁₋₈-alquilo, C₁₋₈-haloalcoxi-C₁₋₈-alquilo, C₁₋₈-haloalquiltio-C₁₋₈-alquilo, COR⁴¹, COOR⁴¹, CONR³⁹R⁴⁰; R³⁷ representa hidrógeno, C₁₋₈-alquilo, C₂₋₈-alquenilo, C₂₋₈-alquinilo C₃₋₁₀-cicloalquilo, C₄₋₁₀-cicloalquenilo, C₁₋₁₀-haloalquilo, C₁₋₈-alcoxi, C₂₋₈-alqueniloxi, arilo, heteroarilo, heterociclilo, COR⁴¹, COOR⁴¹, CONR³⁹R⁴⁰, S(O)ₙR⁴²; n es 0, 1 ó 2; R³⁹ y R⁴⁰ 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, COR⁴¹, SO₂R⁴², 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; R⁴¹ 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 R⁴² 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, NR³⁹R⁴⁰; Y es un enlace o representa los grupos Y-1 a Y-7 del grupo de fórmulas (3) en el que R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷, R⁴⁸, R⁴⁹, R⁵⁰, R⁵¹, R⁵², R⁵³ y R⁵⁴ 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; R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷, R⁴⁸, R⁴⁹, R⁵⁰, R⁵¹, R⁵², R⁵³ y R⁵⁴ representan independientemente hidrógeno, 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; 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 instaurado, 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 instaurado, opcionalmente interrumpido por heteroátomos, con los átomos a los que están unidos; 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; R³ y R⁴ con el átomo al que están unidos, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos, opcionalmente sustituidos; R⁵ y R⁶ con el átomo al que están unidos, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos, opcionalmente sustituidos; R³ y R²³ con el átomo al que están unidos, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos, opcionalmente sustituidos; R⁹ y R¹⁰ con el átomo al que están unidos, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos, opcionalmente sustituidos; y R¹⁵ y R¹⁶ con el átomo al que están unidos, forman un anillo de 5 - 7 miembros opcionalmente sustituido, totalmente saturado o parcialmente saturado, opcionalmente interrumpido por heteroátomos, opcionalmente sustituidos.
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