N-cycloalkyl-N-[(bicyclylphenyl)methylene]-(thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-9770022-B2
Application number	US-201414900735-A
Country	US
Kind code	B2
Filing date	Jun 24, 2014
Priority date	Jun 26, 2013
Publication date	Sep 26, 2017
Grant date	Sep 26, 2017

Abstract

The present invention relates to fungicidal N-cycloalkyl-N-[(bicyclylphenyl)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 selected from the group consisting of:
a heterocycle of formula (A 4 )

wherein:
R 9 to R 11 that can be the same or different represent a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; amino; substituted or non-substituted C 1 -C 5 -alkoxy; substituted or non-substituted C 1 -C 5 -alkylsulfanyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 5 )

wherein:
R 12 and R 13 that can be the same or different represent a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 14 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; amino; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 6 )

wherein:
R 15 represents a hydrogen atom; a halogen atom; a cyano; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 16 and R 18 that can be the same or different represent a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkoxycarbonyl; substituted or non-substituted C 1 -C 5 -alkyl; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 17 represents a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 7 )

wherein:
R 19 represents a hydrogen atom or a C 1 -C 5 -alkyl;
R 20 to R 22 that can be the same or different represent a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 12 )

wherein:
R 31 represents a hydrogen atom or a substituted or non-substituted C 1 -C 5 -alkyl;
R 32 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
R 33 represents a hydrogen atom; a halogen atom; a nitro; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 1 -C 5 -alkoxy; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different;
a heterocycle of formula (A 13 )

wherein:
R 34 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 3 -C 5 -cycloalkyl; 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; substituted or non-substituted C 2 -C 5 -alkynyloxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 35 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; a cyano; substituted or non-substituted C 1 -C 5 -alkoxy; substituted or non-substituted C 1 -C 5 -alkylsulfanyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; substituted or non-substituted C 1 -C 5 -alkylamino or substituted or non-substituted di(C 1 -C 5 -alkyl)amino;
R 36 represents a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 14 )

wherein:
R 37 and R 38 that can be the same or different represent 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 a substituted or non-substituted C 1 -C 5 -alkylsulfanyl;
R 39 represents a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl;
a heterocycle of formula (A 26 )

wherein:
R 65 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; substituted or non-substituted C 3 -C 5 -cycloalkyl; 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; substituted or non-substituted C 1 -C 5 -alkynyloxy or C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different;
R 63 represents a hydrogen atom; a halogen atom; substituted or non-substituted C 1 -C 5 -alkyl; a cyano; substituted or non-substituted C 1 -C 5 -alkoxy; substituted or non-substituted C 1 -C 5 -alkylsulfanyl; C 1 -C 5 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C 1 -C 5 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; substituted or non-substituted C 1 -C 5 -alkylamino or di(C 1 -C 5 -alkyl)amino;
R 64 represents a hydrogen atom or substituted or non-substituted C 1 -C 5 -alkyl;
T represents O or S;
n represents 0, 1, 2, 3 or 4;
L represents a direct bond or CZ 4 Z 5 ;
B represents a substituted or non-substituted bicyclo[2.2.1]heptyl; substituted or non-substituted bicyclo[2.2.1]hept-2-enyl; substituted or non-substituted bicyclo[2.2.2]octyl; substituted or non-substituted bicyclo[2.2.2]oct-2-enyl; substituted or non-substituted 7-oxabicyclo[2.2.1]heptyl; substituted or non-substituted 7-oxabicyclo[2.2.1]hept-2-enyl; substituted or non-substituted bicyclo[3.1.0]hexyl; substituted or non-substituted bicyclo[4.1.0]heptyl; substituted or non-substituted bicyclo[5.1.0]octyl; substituted or non-substituted bicyclo[3.3.0]octyl; substituted or non-substituted bicyclo[4.3.0]nonyl; or substituted or non-substituted bicyclo[4.4.0]decyl; that can be substituted by up to 6 groups Y which can be the same or different;
Z 1 represents a non-substituted cyclopropyl or a cyclopropyl substituted by up to 5 C 1 -C 8 -alkyl;
Z 2 and Z 3 , which can be the same or different, represent a hydrogen atom; non-substituted C 1 -C 8 -alkyl;

Z 4 and Z 5 independently represe

Assignees

• Bayer Cropscience Ag

Inventors

• Benting Jurgen
• Cristau Pierre
• Dahmen Peter
• Desbordes Philippe
• Gary Stephanie
• Rinolfi Philippe
• Tsuchiya Tomoki
• Wachendorff-Neumann Ulrike

Classifications

• A01N33/04 Primary

  Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms · CPC title

• C07D231/14

  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 · CPC title

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N43/36

  five-membered rings · CPC title

• A01N43/10 Primary

  with sulfur as the ring hetero atom · CPC title