N-acyl-2-(cyclo)alkypyrrolidines and piperidines useful as fungicides

Patent metadata

Field	Value
Publication number	US-9357778-B2
Application number	US-201314391441-A
Country	US
Kind code	B2
Filing date	Apr 11, 2013
Priority date	Apr 12, 2012
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

Abstract

The present invention relates to fungicidal 1-(pyrazolylcarbonyl)piperidines or pyrrolidines, 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
T represents O or S;
n represents 0, 1, 2 or 3;
p represents 1 or 2;
Q 1 represents a direct bond; O; S; SO; or SO 2 ; provided that when n represents 0 then Q 1 represents a direct bond; Z 1 and Z 2 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
two substituents Z 1 and Z 2 , together with the carbon atom to which they are linked can form a 3-, 4-, 5- or 6-membered saturated carbocycle that can be substituted by up to four C 1 -C 8 -alkyl groups;
Z 3 represents a hydrogen atom; or substituted or non-substituted C 1 -C 8 -alkyl;
B represents a 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 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylsulfanyl-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylsulfinyl-C 1 -C 8 -alkyl; substituted or non-substituted C 1 -C 8 -alkylsulfonyl-C 1 -C 8 -alkyl; substituted or non-substituted C 3 -C 7 -cycloalkyl; C 3 -C 7 -halogenocycloalkyl having 1 to 9 halogen atoms; substituted or non-substituted (C 3 -C 7 -cycloalkyl)-C 1 -C 8 -alkyl; substituted or non-substituted C 4 -C 7 -cycloalkenyl; C 4 -C 7 -halogenocycloalkenyl having 1 to 9 halogen atoms; substituted or non-substituted (C 4 -C 7 -cycloalkenyl)-C 1 -C 8 -alkyl; substituted or non-substituted bicyclo[2.2.1]heptanyl; substituted or non-substituted bicyclo[2.2.1]hept-2-enyl; substituted or non-substituted bicyclo[2.2.2]octanyl; substituted or non-substituted bicyclo[2.2.2]oct-2-enyl; substituted or non-substituted adamantyl; provided that when n represents 0 and Q 1 represents a direct bond then B is not methyl or ethyl;
R 1 and R 3 independently represent a 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;
R 2 represents a 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 -alkylearbamoyl; phenoxy; phenylsulfanyl; phenylamino; benzyloxy; benzylsulfanyl; or benzylamino;

as well as its salts, N-oxides, metal complexes, metalloid complexes and optically active isomers, provided that the following compounds are excluded:
[2-(chloromethyl)pyrrolidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
[2-(chloromethyl)piperidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
[2-(3-chloropropyl)pyrrolidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
(3-tert-butyl-1-methyl-1H-pyrazol-4-yl)[2-(2-hydroxyethyl)piperidin-1-yl]methanone
(3-tert-butyl-1-isopropyl-1H-pyrazol-4-yl)[2-(2-hydroxyethyl)piperidin-1-yl]methanone
(1,3-dimethyl-1H-pyrazol-4-yl)[2-(2-hydroxyethyl)piperidin-1-yl]methanone
[2-(2-hydroxyethyl)piperidin-1-yl](1-isopropyl-3-methyl-1H-pyrazol-4-yl)methanone
{1-[(1,3,5-trimethyl-1H-pyrazol-4-yl)carbonyl]pyrrolidin-2-yl}acetic acid
[2-(hydroxymethyl)pyrrolidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
{2-[(methylamino)methyl]piperidin-1-yl}(1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
[2-(2-chloroethyl)piperidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
[(2S)-2-(chloromethyl)pyrrolidin-1-yl][3-(difluoromethyl)-1 -methyl-1H-pyrazol-4-yl]methanone
[3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl][(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone
[2-(methoxymethyl)piperidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
[2-(2-hydroxyethyl)piperidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone
{1-[(1,3,5-trimethyl-1H-pyrazol-4-yl)carbonyl]piperidin-2-yl}acetic acid
methyl{1-[(1,3,5-trimethyl-1H-pyrazol-4-yl)carbonyl]piperidin-2-yl}acetate
[2-(hydroxymethyl)piperidin-1-yl](1,3,5-trimethyl-1H-pyrazol-4-yl)methanone.

2. A compound according to claim 1 wherein R 1 represents a 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; R 2 represents a hydrogen atom, or a halogen atom; and R 3 represents a substituted or non-substituted C 1 -C 8 -alkyl.

3. A compound according to claim 2 wherein R 1 represents difluoromethyl; R 2 represents a chlorine atom, or a fluorin

Assignees

• Braun Christoph
• Cristau Pierre
• Desbordes Philippe
• Bayer Cropscience Ag

Inventors

• Braun Christoph
• Cristau Pierre
• Desbordes Philippe

Classifications

• A01N43/56 Primary

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

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N43/06

  five-membered rings · CPC title

• C07D403/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• A01N43/36

  five-membered rings · CPC title