AR098627A1 - Derivados de n-cicloalquil-n-{[2-(1-cicloalquil sustituido)fenil]metilen}-(tio)carboxamida - Google Patents

Derivados de n-cicloalquil-n-{[2-(1-cicloalquil sustituido)fenil]metilen}-(tio)carboxamida

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AR098627A1
AR098627A1 ARP140104527A ARP140104527A AR098627A1 AR 098627 A1 AR098627 A1 AR 098627A1 AR P140104527 A ARP140104527 A AR P140104527A AR P140104527 A ARP140104527 A AR P140104527A AR 098627 A1 AR098627 A1 AR 098627A1
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Argentina
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substituted
unsubstituted
alkyl
halogen atoms
halogen
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Nicolas Lionel
Desbordes Philippe
Cristau Pierre
Tsuchiya Tomoki
Vors Jean
Pierre - Schmidt Jan
Peter - Rinolfi Philippe
Wachendorff-Neumann Ulrike
Geist Julie
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Bayer Cropscience Ag
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Publication of AR098627A1 publication Critical patent/AR098627A1/es

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Abstract

La presente se refiere a derivados fungicidas de N-cicloalquil-N-{[2-(1-cicloalquil sustituido)fenil]metilen}carboxamida y sus derivados de tiocarbonilo, a sus procedimientos de preparación y a compuestos intermedios para su preparación, a su uso como fungicidas, particularmente en la forma de composiciones fungicidas y a métodos para el control de hongos fitopatógenos de plantas que usan estos compuestos o sus composiciones. Reivindicación 1: Un compuesto de fórmula (1) en donde A representa un grupo heterociclilo de 5 miembros, insaturado o parcialmente saturado, unido a carbono, que puede sustituirse por hasta cuatro grupos R que pueden ser iguales o diferentes, con tal que A no represente un grupo 3-(dihalógenometil)-5-halógeno-1-metil-1H-pirazol-4-ilo, en donde los átomos de halógeno pueden representar independientemente un átomo de flúor o cloro; T representa O ó S; n representa 0, 1, 2, 3 ó 4; m representa 0, 1, 2, 3, 4, 5 ó 6; p representa 1, 2, 3, 4 o 5; Z¹ representa un cicloalquilo C₃₋₇ no sustituido o un cicloalquilo C₃₋₇ sustituido con hasta 10 átomos o grupos que pueden ser iguales o diferentes y que pueden seleccionarse de la lista que consiste en átomos de halógeno, ciano, alquilo C₁₋₈, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈ carbonilo, halógenoalcoxi C₁₋₈ carbonilo que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquil C₁₋₈ aminocarbonilo y di-alquil C₁₋₈ aminocarbonilo; Z² y Z³, que pueden ser iguales o diferentes, representan un átomo de hidrógeno; alquilo C₁₋₈ sustituido o no sustituido; alquenilo C₂₋₈ sustituido o no sustituido; alquinilo C₂₋₈ sustituido o no sustituido; ciano; isonitrilo; nitro; un átomo de halógeno; alcoxi C₁₋₈ sustituido o no sustituido; alqueniloxi C₂₋₈ sustituido o no sustituido; alquiniloxi C₂₋₈ sustituido o no sustituido; cicloalquilo C₃₋₇ sustituido o no sustituido; alquil C₁₋₈ sulfanilo sustituido o no sustituido; alquil C₁₋₈ sulfonilo sustituido o no sustituido; alquil C₁₋₈ sulfinilo sustituido o no sustituido; amino; alquil C₁₋₈ amino sustituido o no sustituido; dialquil C₁₋₈ amino sustituido o no sustituido; alcoxi C₁₋₈ carbonilo sustituido o no sustituido; alquil C₁₋₈ carbamoilo sustituido o no sustituido; dialquil C₁₋₈ carbamoilo sustituido o no sustituido; o N-alquil C₁₋₈-alcoxi C₁₋₈-carbamoilo sustituido o no sustituido; o Z² y Z³ junto con el átomo de carbono al que están unidos pueden formar un cicloalquilo C₃₋₇ sustituido o no sustituido; Z⁴ representa un átomo de halógeno; hidroxi; ciano; alquilo C₁₋₈ sustituido o no sustituido; halógenoalquilo C₁₋₈ que tiene de 1 a 5 átomos de halógeno; alquenilo C₂₋₈ sustituido o no sustituido; halógenoalquenilo C₂₋₈ que tiene de 1 a 5 átomos de halógeno; alquinilo C₂₋₈ sustituido o no sustituido; halógenoalquinilo C₂₋₈ que tiene de 1 a 5 átomos de halógeno; alcoxi C₁₋₈ sustituido o no sustituido; halógenoalcoxi C₁₋₈ que tiene de 1 a 5 átomos de halógeno; alquil C₁₋₈ sulfanilo sustituido o no sustituido; formilo; alquil C₁₋₈ carbonilo sustituido o no sustituido; carboxi; o alcoxi C₁₋₈ carbonilo sustituido o no sustituido; X representa independientemente un átomo de halógeno; nitro; ciano; isonitrilo; hidroxi; amino; sulfanilo; pentafluoro-l⁶-sulfanilo; formilo; formiloxi; formilamino; (hidroxiimino)-alquilo C₁₋₈ sustituido o no sustituido; (alcoxiimino C₁₋₈)-alquilo C₁₋₈ sustituido o no sustituido; (alqueniloxi C₂₋₈ imino)-alquilo C₁₋₈ sustituido o no sustituido; (alquiniloxi C₂₋₈ imino)-alquilo C₁₋₈ sustituido o no sustituido; (benciloxiimino)-alquilo C₁₋₈ sustituido o no sustituido; carboxi; carbamoilo; N-hidroxicarbamoilo; carbamato; alquilo C₁₋₈ sustituido o no sustituido; halógenoalquilo C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquenilo C₂₋₈ sustituido o no sustituido; halógenoalquenilo C₂₋₈ que tiene de 1 a 9 átomos de halógeno; alquinilo C₂₋₈ sustituido o no sustituido; halógenoalquinilo C₂₋₈ que tiene de 1 a 9 átomos de halógeno; alcoxi C₁₋₈ sustituido o no sustituido; halógenoalcoxi C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfanilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfanilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfinilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfinilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfonilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfonilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ amino sustituido o no sustituido; dialquil C₁₋₈ amino sustituido o no sustituido; alqueniloxi C₂₋₈ sustituido o no sustituido; halógenoalqueniloxi C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquiniloxi C₃₋₈ sustituido o no sustituido; halógenoalquiniloxi C₂₋₈ que tiene de 1 a 9 átomos de halógeno; cicloalquilo C₃₋₇ sustituido o no sustituido; halógenocicloalquilo C₃₋₇ que tiene de 1 a 9 átomos de halógeno; (cicloalquil C₃₋₇)-alquilo C₁₋₈ sustituido o no sustituido; cicloalquenilo C₄₋₇ sustituido o no sustituido; halógenocicloalquenilo C₄₋₇ que tiene de 1 a 9 átomos de halógeno; (cicloalquil C₃₋₇)-alquenilo C₂₋₈ sustituido o no sustituido; (cicloalquil C₃₋₇)-alquinilo C₂₋₈ sustituido o no sustituido; biciclo[2.2.1]heptanilo, sustituido o no sustituido; biciclo[2.2.1]heptenilo, sustituido o no sustituido; tri(alquil C₁₋₈)sililo sustituido o no sustituido; tri(alquil C₁₋₈)silil-alquilo C₁₋₈ sustituido o no sustituido; alquil C₁₋₈ carbonilo sustituido o no sustituido; halógenoalquil C₁₋₈ carbonilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ carboniloxi sustituido o no sustituido; halógenoalquil C₁₋₈ carboniloxi que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ carbonilamino sustituido o no sustituido; halógenoalquil C₁₋₈ carbonilamino que tiene de 1 a 9 átomos de halógeno; alcoxi C₁₋₈ carbonilo sustituido o no sustituido; halógenoalcoxi C₁₋₈ carbonilo que tiene de 1 a 9 átomos de halógeno; alquiloxi C₁₋₈ carboniloxi sustituido o no sustituido; halógenoalcoxi C₁₋₈ carboniloxi que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ carbamoilo sustituido o no sustituido; dialquil C₁₋₈ carbamoilo sustituido o no sustituido; alquil C₁₋₈ aminocarboniloxi sustituido o no sustituido; dialquil C₁₋₈ aminocarboniloxi sustituido o no sustituido; N-(alquil C₁₋₈)hidroxicarbamoilo sustituido o no sustituido; alcoxi C₁₋₈ carbamoilo sustituido o no sustituido; N-(alquil C₁₋₈)-alcoxi C₁₋₈ carbamoilo sustituido o no sustituido; arilo que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquilo C₁₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquenilo C₂₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquinilo C₂₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; ariloxi que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilsulfanilo que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilamino que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquiloxi C₁₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquilsulfanilo C₁₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; arilalquilamino C₁₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; heteroarilalquilo C₁₋₈ que puede estar sustituido por hasta 6 grupos Q que pueden ser iguales o diferentes; heteroarilo que puede estar sustituido por hasta 4 grupos Q; o heteroariloxi que puede estar sustituido por hasta 4 grupos Q; o Z⁴ y su sustituyente X vecino, junto con el átomo de carbono al que están unidos, pueden formar un cicloalquilo C₄₋₇ sustituido o no sustituido; Y representa independientemente un átomo de halógeno; alquilo C₁₋₈; halógenoalquilo C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alcoxi C₁₋₈ sustituido o no sustituido; halógenoalcoxi C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfanilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfanilo que tiene de 1 a 9 átomos de halógeno; o alcoxi C₁₋₈ carbonilo sustituido o no sustituido; Q representa independientemente un átomo de halógeno, ciano, nitro, alquilo C₁₋₈ sustituido o no sustituido, halógenoalquilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alcoxi C₁₋₈ sustituido o no sustituido, halógenoalcoxi C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, alquilsulfanilo C₁₋₈ sustituido o no sustituido, halógenoalquilsulfanilo C₁₋₈ que comprende hasta 9 átomos de halógeno que pueden ser iguales o diferentes, tri(alquil C₁₋₈)sililo sustituido o no sustituido, tri(alquil C₁₋₈)silil-alquilo C₁₋₈ sustituido o no sustituido, (alcoxi C₁₋₈ imino)-alquilo C₁₋₈ sustituido o no sustituido, o (benciloxiimino)-alquilo C₁₋₈ sustituido o no sustituido; R representa independientemente un átomo de hidrógeno; átomo de halógeno; nitro; ciano; hidroxi; amino; sulfanilo; pentafluoro-l⁶-sulfanilo; (alcoxiimino C₁₋₈)-alquilo C₁₋₈ sustituido o no sustituido; (benciloxiimino)-alquilo C₁₋₈ sustituido o no sustituido; alquilo C₁₋₈ sustituido o no sustituido; halógenoalquilo C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquenilo C₂₋₈ sustituido o no sustituido; halógenoalquenilo C₂₋₈ que tiene de 1 a 9 átomos de halógeno; alquinilo C₂₋₈ sustituido o no sustituido; halógenoalquinilo C₂₋₈ que tiene de 1 a 9 átomos de halógeno; alcoxi C₁₋₈ sustituido o no sustituido; halógenoalcoxi C₁₋₈ que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfanilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfanilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfinilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfinilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ sulfonilo sustituido o no sustituido; halógenoalquil C₁₋₈ sulfonilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ amino sustituido o no sustituido; dialquil C₁₋₈ amino sustituido o no sustituido; alqueniloxi C₂₋₈ sustituido o no sustituido; alquiniloxi C₃₋₈ sustituido o no sustituido; cicloalquilo C₃₋₇ sustituido o no sustituido; halógenocicloalquilo C₃₋₇ que tiene de 1 a 9 átomos de halógeno; tri(alquil C₁₋₈)sililo sustituido o no sustituido; alquil C₁₋₈ carbonilo sustituido o no sustituido; halógenoalquil C₁₋₈ carbonilo que tiene de 1 a 9 átomos de halógeno; alcoxi C₁₋₈ carbonilo sustituido o no sustituido; halógenoalcoxi C₁₋₈ carbonilo que tiene de 1 a 9 átomos de halógeno; alquil C₁₋₈ carbamoilo sustituido o no sustituido; dialquil C₁₋₈ carbamoilo sustituido o no sustituido; fenoxi; fenilsulfanilo; fenilamino; benciloxi; bencilsulfanilo; o bencilamino; además de sus sales, N-óxidos, complejos metálicos, complejos metaloides e isómeros ópticamente activos o isómeros geométricos de los mismos. Reivindicación 15: Un compuesto de fórmula (2) además de sus sales aceptables, en donde Z¹, Z², Z³, Z⁴, n, m, p, X e Y son como se definen según cualquiera de las reivindicaciones 1 a 14. Reivindicación 16: Un compuesto de fórmula (3) en donde Z⁴, n, m, p, X e Y son como se definen en cualquiera de las reivindicaciones 1 a 14, con tal que ese compuesto de fórmula (3) no represente: 2-(1-metoxicicloheptil)-5-(trifluorometil)benzaldehído, (1S,2S)-2-etoxi-2-(2-formilfenil)ciclopropanocarboxilato de metilo, o (1S,2R)-2-etoxi-2-(2-formilfenil)ciclopropanocarboxilato de metilo. Reivindicación 17: Un compuesto de fórmula (4), en donde U² es un halógeno y Z⁴, n, m, p, X e Y son como se definen en cualquiera de las reivindicaciones 1 a 14, con tal que ese compuesto de fórmula (4) no represente: 1-[2-(bromometil)-3-clorofenil]ciclobutanol, 1-[2-(bromometil)fenil]ciclopropanocarbonitrilo, 1-[2-(bromometil)-4-(trifluorometil)fenil]cicloheptilmetiléter, 2-(bromometil)-1-(1-metoxiciclopentil)-4-(trifluorometil)benceno, 2-(bromometil)-1-(1-metoxiciclohexil)-4-(trifluorometil)benceno, o 1-[2-(bromometil)fenil]ciclopentanocarbonitrilo.
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