Fungicidal 3-{phenyl[heterocyclylmethoxy)imino]methyl}-oxadiazolone derivatives

Patent metadata

Field	Value
Publication number	US-9743665-B2
Application number	US-201414767445-A
Country	US
Kind code	B2
Filing date	Mar 3, 2014
Priority date	Mar 4, 2013
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

The present invention provides 4-substituted-3-{phenyl[(heterocyclylmethoxy)imino]methyl}-1,2,4-oxadiazol-5(4H)-one derivatives of formula (I)

Wherein A and X 1 to X 3 and Y1 to Y 5 represent various substituents.

First claim

The invention claimed is:

1. A compound of formula (I)

and/or a salt, N-oxide, metallic complex, and/or metalloidic complex thereof and/or an (E) and/or (Z) isomer and/or a mixture thereof,
wherein
X 1 represents a hydrogen atom, 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;
X 2 and X 3 represent O or C═O, provided that X 2 represents O when X 3 is C═O and X 2 represents C═O when X 3 is O;
A is

wherein
Z 1 represents a hydrogen atom, a halogen atom, a nitro group, an amino group, a carbamoyl group, 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 aryl-C 2 -C 8 -alkynyl, substituted or non-substituted C 3 -C 8 -cycoalkyl-C 2 -C 8 -alkynyl, substituted or non-substituted N—C 1 -C 8 -alkyl-carbamoyl, substituted or non-substituted N—C 3 -C 8 -cycloalkyl-carbamoyl, substituted or non-substituted N-aryl-carbamoyl, 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 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 aryl, substituted or non-substituted heterocyclyl, substituted or non-substituted C 5 -C 12 -benzofused heterocyclyl, substituted or non-substituted aryl-C 1 -C 8 -alkyl, substituted or non-substituted aryloxy-C 1 -C 8 -alkyl, or substituted or non-substituted C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl,
wherein optional substituents for Q are selected from the group consisting of a halogen atom, a cyano group, a C 1 -C 8 -alkyl group, and a C 1 -C 8 -alkoxy group;
U represents a oxygen atom; and
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, or substituted or non-substituted C 1 -C 8 -alkoxy;
Z 2 represents 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, or substituted or non-substituted C 1 -C 8 -alkoxy; and
Y 1 to Y 5 independently represent a hydrogen atom, a halogen atom, C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -halogenoalkyl having 1 to 5 halogen atoms, or C 1 -C 8 -alkoxy.

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

3. A compound according to claim 1 wherein Z 1 represents a halogen atom, a nitro group, a carboxylic acid, an amino group, substituted or non-substituted C 2 -C 8 -alkynyl, or a group of formula QC(═U)NR a .

4. A compound according to claim 1 wherein R a represents a hydrogen atom.

5. A compound according to claim 1 wherein Q represents a substituted or non-substituted C 4 -C 8 -alkyl, substituted or non-substituted C 3 -C 8 -cyclo-alkyl, substituted or non-substituted C 4 -C 8 -alkenyl, substituted or non-substituted C 4 -C 8 -alkoxy, substituted or non-substituted C 4 -C 8 -alkenyloxy, substituted or non-substituted C 4 -C 8 -alkynyloxy, alkynyloxy, substituted or non-substituted aryl, or substituted or non-substituted heterocyclyl.

6. A compound according to claim 1 wherein Q represents a C 5 -C 12 -benzofused hetercyclyl.

7. A compound according to claim 1 wherein Z 2 , Z 3 and Z 4 independently represent a hydrogen atom, a halogen atom, or substituted or non-substituted C 1 -C 8 -alkyl.

8. A compound according to claim 1 wherein Y 1 to Y 5 each represents a hydrogen atom.

9. A compound according to claim 1 wherein Q represents 3,4-dihydro-2H-chromen-2-yl.

10. A compound of formula (I) according to claim 1

and/or a salt, N-oxide, metallic complex, and/or metalloidic complex thereof and/or an (E) and/or (Z) isomer and/or a mixture thereof, wherein A is

X 1 is methyl, X 2 is CO, X 3 is O, Y 1 is hydrogen, Y 2 is hydrogen, Y 3 is hydrogen, Y 4 is hydrogen, Y 5 is hydrogen, Z 1 is (3,4-dihydro-2H-chromen-2-ylcarbonyl)amino, and Z 2 is hydrogen.

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A61P31/10

  Antimycotics · CPC title

• C07D277/24

  Radicals substituted by oxygen atoms · CPC title

• C07D277/56

  Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen · CPC title

• A01N43/78

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

• C07D417/12

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