Fungicidal 3-[(pyridin-2-ylmethoxyimino)(phenyl)methyl]-2-substituted-1,2,4-oxadiazol-5(2H)-one derivatives

Patent metadata

Field	Value
Publication number	US-9556158-B2
Application number	US-201214369148-A
Country	US
Kind code	B2
Filing date	Dec 19, 2012
Priority date	Dec 29, 2011
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The present invention relates to 3-[(pyridin-2-ylmethoxyimino)(phenyl)methyl]-2-substituted-1,2,4-oxadiazol-5(2H)-one derivatives of formula (I), their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
the X-shaped carbon-nitrogen bond is a double bond wherein formula (I) is in either E or Z configuration;
X 1 represents a substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted C 1 -C 8 -alkylcarbonyl;
Z 1 represents a hydrogen atom, a halogen atom, a nitro group, an amino group, an hydroxyamino group, a cyano group, a carboxylic acid group, substituted or non-substituted C 1 -C 8 -alkoxyamino group, substituted or non-substituted C 1 -C 8 -alkylamino, substituted or non-substituted C 3 -C 10 -cycloalkylamino, substituted or non-substituted C 3 -C 10 -cycloalkenylamino, substituted or non-substituted C 5 -C 12 -fused bicycloalkylamino, substituted or non-substituted C 3 -C 10 -cycloalkyl-C 1 -C 8 -alkylamino, substituted or non-substituted aryl-C 1 -C 8 -alkylamino, substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkylamino, substituted or non-substituted C 5 -C 12 -fused bicycloalkenylamino, substituted or non-substituted di-C 1 -C 8 -alkylamino, substituted or non-substituted phenylamino, substituted or non-substituted heterocyclylamino, or a group of formula QC(═U)NR a —
wherein:

Q represents a hydrogen atom, substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, a substituted or non-substituted C 2 -C 8 -alkenyl, substituted or non-substituted C 3 -C 8 -cycloalkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, 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 1 -C 8 -alkylamino, substituted or non-substituted C 1 -C 8 -alkylsulfenyl, substituted or non-substituted C 2 -C 8 -alkenylsulfenyl, substituted or non-substituted C 2 -C 8 -alkynylsulfenyl, substituted or non-substituted arylsulfenyl, substituted or non-substituted aryl, substituted or non-substituted heterocyclyl, substituted or non-substituted C 5 -C 12 -fused bicycloalkyl, substituted or non-substituted C 5 -C 12 -fused bicycloalkenyl, substituted or non-substituted C 5 -C 12 -benzofused carbocyclyl, substituted or non-substituted C 5 -C 12 -benzofused heterocyclyl, substituted or non-substituted cycloalkoxy; substituted or non-substituted cycloalkenyloxy, substituted or non-substituted aryloxy; substituted or non-substituted heterocyclyloxy, substituted or non-substituted C 5 -C 12 -fused bicycloalkoxy, substituted or non-substituted C 5 -C 12 -fused bicycloalkenyloxy, substituted or non-substituted C 5 -C 12 -benzofused carbocyclyloxy, substituted or non-substituted C 5 -C 12 -benzofused heterocyclyloxy, substituted or non-substituted C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl-C 1 -C 8 -alkoxy, substituted or non-substituted C 3 -C 8 -cycloalkoxy-C 1 -C 8 -alkyl, substituted or non-substituted heterocyclyl-C 1 -C 8 -alkyl, substituted or non-substituted aryl-C 1 -C 8 -alkyl, substituted or non-substituted aryl-C 1 -C 8 -alkoxy, substituted or non-substituted aryloxy-C 1 -C 8 -alkyl, substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy, substituted or non-substituted aryloxy-C 1 -C 8 -alkoxy, substituted or non-substituted C 1 -C 8 -alkoxyaryloxy, substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, substituted or non-substituted aryl-C 1 -C 8 -alkynyloxy, substituted or non-substituted C 1 -C 8 -alkylaryl, substituted or non-substituted C 1 -C 8 -alkoxyaryl, substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkoxy, substituted or non-substituted C 1 -C 8 -alkyl-C 3 -C 8 -cycloalkoxy, substituted or non-substituted C 1 -C 8 -alkyl-C 3 -C 8 -cycloalkyl;
U represents a oxygen atom or a sulfur atom;
R a represents a hydrogen atom, a hydroxy group, substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, a substituted or non-substituted C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted C 1 -C 8 -alkoxy, substituted or non-substituted C 3 -C 10 -cycloalkenyl, substituted or non-substituted C 5 -C 12 -fused bicycloalkyl, substituted or non-substituted C 5 -C 12 -fused bicycloalkenyl, substituted or non-substituted aryl, or substituted or non-substituted heterocyclyl, substituted or non-substituted C 1 -C 8 -alkylcarbonyl, substituted or non-substituted aryloxycarbonyl, substituted or non-substituted C 1 -C 8 -alkoxycarbonyl;
Z 2 , Z 3 and Z 4 independently represent a hydrogen atom, a halogen atom, substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted C 1 -C 8 -alkoxy;
Y 1 to Y 5 independently represent a hydrogen atom, a halogen atom, a nitro group, a a cyano group, a substituted or non-substituted carbaldehyde O—(C 1 -C 8 -alkyl)oxime, a pentafluoro-λ 6 -sulfenyl group, substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl, substituted or non-substituted C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, a C 2 -C 8 -alkenyl, substituted or non-substituted C 2 -C 8 -alkynyl, substituted or non-substituted C 1 -C 8 -alkoxy, substituted or non-substituted C 1 -C 8 -halogenoalkoxy having 1 to 5 halogen atoms, substituted or non-substituted C 1 -C 8 -alkylsulfenyl, substituted or non-substituted C 2 -C 8 -alkenyloxy, substituted or non-substituted C 3 -C 8 -alkynyloxy, substituted or non-substituted N—(C 1 -C 8 -alkoxy)-C 1 -C 8 -alkanimidoyl, substituted or non-substituted N—(C 1 -C 8 -alkoxy)-C 1 -C 8 -halogenoalkanimidoyl having 1 to 5 halogen atoms, substituted or non-substituted C 1 -C 8 -alkoxycarbonyl, substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy, substituted or non-substituted C 1 -C 8 -alkylsulfinyl, substituted or non-substituted C 1 -C 8 -alkylsulfonyl, substituted or non-substituted phenoxy, substituted or non-substituted phenylsulfenyl, substituted or non-substituted aryl, substituted or non-substituted tri(C 1 -C 8 -alkyl)-silyloxy, substituted or non-substituted tri(C 1 -C 8 -alkyl)-silyl, substituted or non-substituted heterocyclyl, substituted or non-substituted heterocyclyloxy;

as well as salts, N-oxides, metallic complexes and metalloidic complexes thereof or (E) and (Z) isomers and mixtures thereof.

2. A compound according to claim 1 wherein X 1 represents substituted or non-substituted C 1 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cycloalkyl or a substituted or non-substituted C 2 -C 8 -alkenyl.

3. A compound according to claim 1 wherein X 1 represents a methyl group, an ethyl group, a n-propyl group, an isopropyl group or a cyclopropyl group.

4. A compound according to claim 1 wherein Z 1 represents a hydrogen atom, a halogen atom, a nitro group, an amino group, an hydroxyamino group, substituted or non-substituted C 1 -C 8 -alkoxyamino group, substituted or non-substituted C 1 -C 8 -alkylamino, substituted or non-substituted C 3 -C 10 -cycloalkylamino, substituted or non-substituted C 3 -C 10 -cycloalkenylamino, substituted or non-substituted C 5 -C 12 -fused bicycloalkylamino, substituted or non-substituted C 5 -C 12 -fused bicycloalkenylamino, substituted or non-substituted di-C 1 -C 8 -alkylamino, substituted or non-substituted phenylamino, substituted or non-substituted heterocyclylamino, or a group of formula QC(═U)NR a —.

5. A compound acco

Assignees

• Bayer Ip Gmbh

Inventors

• Braun Christoph
• Coqueron Pierre-Yves
• Dubost Christophe
• Lachaise Helene
• Maechling Simon
• Rebstock Anne-Sophie
• Rinolfi Philippe
• Sawada Haruko
• Wachendorff-Neumann Ulrike

Classifications

• C07D413/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D213/75

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title