N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl)phenyl]methylene}-(thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-10071967-B2
Application number	US-201415101380-A
Country	US
Kind code	B2
Filing date	Dec 4, 2014
Priority date	Dec 5, 2013
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

Abstract

The present invention relates to fungicidal N-cycloalkyl-N-{[2-(1-substitutedcycloalkyl)phenyl]methylene} carboxamide derivatives and their thiocarbonyl derivatives, their process of preparation and intermediate compounds for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
A is a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R that can be the same or different, provided that A is not a 3-(dihalogenomethyl)-5-halogeno-1-methyl-1H-pyrazol-4-yl group wherein the halogeno atoms are independently a fluoro or chloro atom;
T is O or S;
n is 0, 1, 2, 3 or 4;
m is 0, 1, 2, 3, 4, 5 or 6;
p is 1;
Z 1 is a non-substituted C 3 -C 7 -cycloalkyl or a C 3 -C 7 -cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that are selected from the list consisting of halogen atoms, cyano, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxy, C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkoxycarbonyl, C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different, C 1 -C 8 -alkylaminocarbonyl and di-C 1 -C 8 -alkylaminocarbonyl;
Z 2 and Z 3 , which can be the same or different, are a hydrogen atom; substituted or non-substituted C 1 -C 8 -alkyl; substituted or non-substituted C 2 -C 8 -alkenyl; substituted or non-substituted C 2 -C 8 -alkynyl; cyano; isonitrile; nitro; a halogen atom; substituted or non-substituted C 1 -C 8 -alkoxy; substituted or non-substituted C 2 -C 8 -alkenyloxy; substituted or non-substituted C 2 -C 8 -alkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; amino; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; or substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxy-carbamoyl; or
Z 2 and Z 3 are taken together with the carbon atom to which they are linked to form a substituted or non-substituted C 3 -C 7 -cycloalkyl;
Z 4 is a halogen atom; hydroxy; cyano; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 5 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; formyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; carboxy; or substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
X independently is a halogen atom; non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; aryl phenyl that can be substituted by up to 6 C 1 -C 8 -alkyl which can be the same or different; or
Z 4 and its vicinal substituent X are taken together with the carbon atom to which they are linked to form a substituted or non-substituted C 4 -C 7 -cycloalkyl;
Y independently is a halogen atom; C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 9 halogen atoms; or substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
R independently is hydrogen atom; halogen atom; nitro; cyano; hydroxy; amino; sulfanyl; pentafluoro-λ 6 -sulfanyl; substituted or non-substituted (C 1 -C 8 -alkoxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted (benzyloxyimino)-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl having 1 to 9 halogen atoms; substituted or non-substituted C 2 -C 8 -alkynyl; C 2 -C 8 -halogenoalkynyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; C 1 -C 8 -halogenoalkylsulfanyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfinyl; C 1 -C 8 -halogenoalkylsulfinyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylamino; substituted or non-substituted di-C 1 -C 8 -alkylamino; substituted or non-substituted C 2 -C 8 -alkenyloxy; substituted or non-substituted C 3 -C 8 -alkynyloxy; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 9 halogen atoms; substituted or non-substituted tri(C 1 -C 8 )alkylsilyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl having 1 to 9 halogen atoms; substituted or non-substituted C 1 -C 8 -alkylcarbamoyl; substituted or non-substituted di-C 1 -C 8 -alkylcarbamoyl; phenoxy; phenylsulfanyl; phenylamino; benzyloxy; benzylsulfanyl; or benzylamino;

or a salt, N-oxide, metal complex, metalloid complex, optically active isomer or geometric isomer thereof.

2. The compound according to claim 1 , or a salt, N-oxide, metal complex, metalloid complex, optically active isomer or geometric isomer thereof, wherein A is selected from the list consisting of:
a heterocycle of formula (A 1 )

wherein:
R 1 to R 3 that can be the same or different are a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 2 )

wherein:
R 4 to R 6 that can be the same or different are a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 3 )

wherein:
R 7 is a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 5 -alkoxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 8 is a hydrogen atom or a substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 4 )

wherein:
R 9 to R 11 that can be the same or different are a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alky

Assignees

• Bayer Cropscience Ag

Inventors

• Cristau Pierre
• Desbordes Philippe
• Geist Julie
• Nicolas Lionel
• Rinolfi Philippe
• Schmidt Jan-Peter
• Tsuchiya Tomoki
• Vors Jean-Pierre
• Wachendorff-Neumann Ulrike

Classifications

• C07D249/06

  with aryl radicals directly attached to ring atoms · CPC title

• C07D307/54

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• A01N35/04

  containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals · CPC title

• C07D231/16

  Halogen atoms or nitro radicals · CPC title

• C07F7/0803

  Compounds with Si-C or Si-Si linkages · CPC title