Fungicidal N-bicycloalkyl and N-tricycloalkyl pyrazole-4-(thio)carboxamide derivatives

Patent metadata

Field	Value
Publication number	US-9725414-B2
Application number	US-201214361534-A
Country	US
Kind code	B2
Filing date	Nov 29, 2012
Priority date	Nov 30, 2011
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

The present invention relates to fungicidal N-bicycloalkyl and N-tricycloalkyl pyrazole-4-(thio)carboxamide derivatives of formula (I), wherein T represents O or S; n represents 0 or 1; and B represents where the bond marked by * is attached to the (CZ2Z3)n-N amide moiety, 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
T represents O or S;
n represents 1;
B represents

 where the bond marked by * is attached to the (CZ 2 Z 3 ) n —N amide moiety;
m represents 0 or 1;
p represents 0, 1, 2 or 3; providing that m+p is equal to 1 to 3;
t represents 1 or 2;
u represents 1, 2, 3 or 4;
Q 1 represents a direct bond, CZ 7 Z 8 , O, S, SO, SO 2 , NZ 11 , —C(═V)—, —C(═NZ 12 )—, a non-substituted C 1 -C 8 -alkylidene or a substituted C 1 -C 8 -alkylidene substituted by up to 10 atoms or groups that can be the same or different and that can be selected in 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; providing that
when Q 1 is not a direct bond then t+u is equal to 2 to 4; or
when Q 1 is a direct bond then u is equal to 3 or 4; or
when t is equal to 2 then [Q 1 ] 2 is not a peroxide group;

Q 2 represents CZ 9 Z 10 or —CH═CH—;
V represents O or S;
Z 1 represents a hydrogen atom; a formyl group; a substituted or non-substituted C 1 -C 8 -alkyl; 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 can be selected in 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; provided that—when Z 1 represents a hydrogen atom, n represents 0, T represents O and B represents a optionally mono alkyl-substituted, saturated or partially unsaturated, decahydronaphthalenyl group, octahydro-1H-inden-4-yl group or octahydro-1H-inden-5-yl group then R 1 and R 3 are not simultaneously a methyl group when R 2 is a fluorine atom;
Z 2 and Z 3 independently represent a hydrogen atom; a halogen atom; 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 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; or substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; or Z 2 and Z 3 are a C 2 -C 5 -alkylene group that can be substituted by up to four C 1 -C 8 -alkyl groups;
Z 4 , Z 5 , Z 6 , Z 7 , Z 9 or Z 10 independently represent a hydrogen atom; a halogen atom; 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 1 -C 8 -alkoxy; substituted or non-substituted C 1 -C 8 -alkylsulfanyl; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; or benzyl group;
Z 11 represents a hydrogen atom; a substituted or non-substituted C 1 -C 8 -alkyl; a C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 2 -C 8 -alkenyl; C 2 -C 8 -halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 3 -C 8 -alkynyl; C 3 -C 8 -halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogeno-cycloalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl-C 1 -C 8 -alkyl; formyl; substituted or non-substituted C 1 -C 8 -alkylcarbonyl; C 1 -C 8 -halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 8 -alkoxycarbonyl; C 1 -C 8 -halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 8 -alkylsulfonyl; C 1 -C 8 -halogenoalkylsulfonyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted benzyl; or substituted or non-substituted phenylsulfonyl;
Z 12 represents a hydrogen atom, a substituted or non-substituted C 1 -C 8 -alkyl; C 1 -C 8 -halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 1 -C 8 -alkoxy; C 1 -C 8 -halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogeno-cycloalkyl comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted C 3 -C 7 -cycloalkoxy; C 3 -C 7 -halogenocycloalkoxy comprising up to 9 halogen atoms that can be the same or different; substituted or non-substituted benzyl; substituted or non-substituted phenyl; substituted or non-substituted benzyloxy; or substituted or non-substituted phenoxy;
R 1 , R 2 and R 3 independently represents a hydrogen atom; halogen atom; non-substituted C 1 -C 8 -alkyl or C 1 -C 8 -halogenoalkyl having 1 to 9 halogen atoms; wherein not more than one of R 1 , R 2 and R 3 is hydrogen
Provided that the compound is not:
5-chloro-N,1,3-trimethyl-N-(tricycle[3.3.1.13,7]dec-1-ylmethyl)-1H-pyrazole-4-carboxamide;
N-(adamantan-1-ylmethyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, or
5-benzyl-1,3-dimethyl-1H-pyrazole-4-carboxylic acid (adamantan-1-ylmethyl)-amide
N-(adamantan-1-ylmethyl)-5-chloro-1-(4-fluorobenzyl)-3-methyl- 1H-pyrazole-4-carboxamide;
1-benzyl-N-[1-(bicyclo[2.2.1]hept-2-yl)ethyl]-5-chloro-3-methyl-1H-pyrazole-4-carboxamide;
N-(adamantan-1-ylmethyl)-1-benzyl-5-chloro-3-methyl-1H-pyrazole-4-carboxamide;
N-(adamantan-1-ylmethyl)-5-chloro-3-methyl-1-(4-methylbenzyl)- 1H-pyrazole -4-carboxamide;
N-(adamantan-l-ylmethyl)-5-chloro-N,1,3-trimethyl-1H-pyrazole-4-carboxamide;
N-[1-(adamantan-1-yl)ethyl]-1-benzyl-5-chloro-3-methyl-1 H-pyrazole-4-carboxamide;
N-[1-(bicyclo[2.2.1]hept-2-yl)ethyl]-1-ethyl-3-methyl-1H-pyrazole-4-carboxamide; or
N-[1-(bicyclo[2.2.1]hept-2-yl)ethyl]-5-chloro-3-methyl-1-(4-methylbenzyl)-1H-pyrazole-4-carboxamide,

as well as its salts, N-oxides, metal complexes, metalloid complexes and optically active isomers.

2. A compound according to claim 1 wherein R 1 represents a 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 2 represents a hydrogen atom, or a halogen atom; and R 3 represents a non-substituted C 1 -C 5 -alkyl.

3. A compound according to claim 1 wherein R 1 represents C 1 -C 5 -alkyl or C 1 -C 5 -halogenoalkyl comprising up to 3 halogen atoms that can be the same or different; R 2 represents a hydrogen atom, a chlorine atom, or a fluorine atom; and R 3 represents a methyl.

4. A compound according to claim 1 wherein T represents O.

5. A compound according to claim 1 wherein B represents B 1 ; Q 1 represents a direct bond; u is equal to 3 or 4; and m+p is equal to 2 or 3.

6. A compound according to claim 1 wherein B represents a substituted or non-substituted decahydronaphthalenyl group, a substituted or

Assignees

• Bayer Ip Gmbh

Inventors

• Benting Jurgen
• Brunet Stephane
• Coqueron Pierre-Yves
• Cristau Pierre
• Dahmen Peter
• Desbordes Philippe
• Gary Stephanie
• Greul Jorg
• Lachaise Helene
• Schmidt Jan-Peter
• Rinolfi Philippe
• Vors Jean-Pierre
• Wachendorff-Neumann Ulrike

Classifications

• A61P31/10

  Antimycotics · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07D231/16

  Halogen atoms or nitro radicals · CPC title

• A61P17/00

  Drugs for dermatological disorders · CPC title

• C07C211/38

  containing condensed ring systems · CPC title