AR098626A1 - 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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AR098626A1
AR098626A1 ARP140104526A ARP140104526A AR098626A1 AR 098626 A1 AR098626 A1 AR 098626A1 AR P140104526 A ARP140104526 A AR P140104526A AR P140104526 A ARP140104526 A AR P140104526A AR 098626 A1 AR098626 A1 AR 098626A1
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substituted
unsubstituted
alkyl
halogen atoms
halogen
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Cristau Pierre
Desbordes Philippe
Geist Julie
Nicolas Lionel
Rinolfi Philippe
Vors Jean
Pierre - Schmidt Jan
Peter - Tsuchiya Tomoki
Wachendorff-Neumann Ulrike
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Bayer Cropscience Ag
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—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
    • 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
    • C07D231/16—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/12—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

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 X¹ y X² que pueden ser iguales o diferentes, representan un átomo de cloro o flúor; 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 ó 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; W 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 C₂₋₈ 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 W 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; además de sus sales, N-óxidos, complejos metálicos, complejos metaloides e isómeros ópticamente activos o isómeros geométricos de los mismos. Reivindicación 13: Un compuesto de fórmula (2), además de sus sales aceptables, en donde Z¹, Z², Z³, Z⁴, n, m, p, W e Y son como se define en cualquiera de las reivindicaciones 1 a 12. Reivindicación 14: Un compuesto de fórmula (3) en donde Z⁴, n, m, p, W e Y son como se definen en cualquiera de las reivindicaciones 1 a 12, 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, y (1S,2R)-2-etoxi-2-(2-formilfenil)ciclopropanocarboxilato de metilo. Reivindicación 15: Un compuesto de fórmula (4), en donde U² es un halógeno y Z⁴, n, m, p, W e Y son como se definen en esta memoria, con tal que el 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, y 1-[2-(bromometil)fenil]ciclopentanocarbonitrilo.
ARP140104526A 2013-12-05 2014-12-05 Derivados de n-cicloalquil-n-{[2-(1-cicloalquil sustituido)fenil]metilen}-(tio)carboxamida AR098626A1 (es)

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TW201607929A (zh) 2013-12-05 2016-03-01 拜耳作物科學公司 Ｎ－環烷基－ｎ－｛［２－（１－經取代環烷基）苯基］亞甲基｝－（硫代）甲醯胺衍生物
CA2986492A1 (en) * 2015-05-21 2016-11-24 Bayer Cropscience Aktiengesellschaft Fungicidal n-cycloalkyl-n-{[ortho-(1-substituted-cycloalkyl)heteroaryl]methyl}pyrazole(thio)carboxamids

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