Fungicidal 3--oxadiazolone derivatives

Patent metadata

Field	Value
Publication number	US-2016000078-A1
Application number	US-201414771667-A
Country	US
Kind code	A1
Filing date	Mar 3, 2014
Priority date	Mar 4, 2013
Publication date	Jan 7, 2016
Grant date	—

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, X 1 to X 3 , Y 1 to Y 5 represent various substituents

First claim

1 . A compound of formula (I)

wherein
X 1 represents a hydrogen atom, a formyl 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, or substituted or non-substituted C 1 -C 8 -alkylcarbonyl;
X 2 and X 3 independently represents 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 selected in the list consisting of A 1 to A 2 :

wherein
Z 1 represents a hydroxy group, a sulfenyl group, a formyl group, a substituted or non-substituted carbaldehyde O—(C 1 -C 8 -alkyl)oxime, a formyloxy group, a carbamoyl group, a N-hydroxycarbamoyl group, sulfenylthioylamino, a pentafluoro- 6 -sulfenyl group, substituted or non-substituted (C 1 -C 8 -alkylamino)-amino group, substituted or non-substituted N—C 1 -C 8 -alkyl-(C 1 -C 8 -alkylamino)-amino group, a substituted or non-substituted (hydroxyimino)-C 1 -C 6 -alkyl 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 -cycloalkyl-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 3 -C 8 -alkynyloxy, substituted or non-substituted C 1 -C 8 -alkylcarbonyl, substituted or non-substituted N—(C 1 -C 8 -alkoxy)-C 1 -C 8 -alkanimidoyl, substituted or non-substituted N—C 1 -C 8 -alkyl-carbamoyl, substituted or non-substituted N,N′-di-C 1 -C 8 -alkyl-carbamoyl, substituted or non-substituted N—C 1 -C 8 -alkyloxycarbamoyl, substituted or non-substituted C 1 -C 8 -alkoxycarbamoyl, substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamoyl, substituted or non-substituted C 1 -C 8 -alkoxycarbonyl, substituted or non-substituted C 1 -C 8 -alkylcarbonyloxy, substituted or non-substituted N—C 1 -C 8 -alkylaminocarbonyloxy, substituted or non-substituted N,N′-di-C 1 -C 8 -alkylaminocarbonyloxy, substituted or non-substituted N—C 1 -C 8 -alkylcarbamothioyl, substituted or non-substituted N,N′-di-C 1 -C 8 -alkylcarbamothioyl, substituted or non-substituted N—C 1 -C 8 -alkyloxycarbamothioyl, substituted or non-substituted C 1 -C 8 -alkoxycarbamothioyl, substituted or non-substituted N—C 1 -C 8 -alkyl-C 1 -C 8 -alkoxycarbamothioyl, substituted or non-substituted (C 1 -C 8 -alkyl-carbamothioyl)-oxy, substituted or non-substituted substituted or non-substituted (di-C 1 -C 8 -alkyl-carbamothioyl)-oxy, substituted or non-substituted C 1 -C 8 -alkylsulfenyl, substituted or non-substituted C 1 -C 8 -halogenoalkylsulfenyl having 1 to 5 halogen atoms, substituted or non-substituted C 1 -C 8 -alkylsulfinyl, substituted or non-substituted C 1 -C 8 -alkylsulfonyl, substituted or non-substituted C 1 -C 8 -alkylaminosulfamoyl, substituted or non-substituted (C 1 -C 6 -alkoxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (benzyloxyimino)-C 1 -C 6 -alkyl, 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 C 1 -C 8 -alkylsulfenylamino, substituted or non-substituted C 1 -C 8 -alkylsulfonylamino, substituted or non-substituted C 1 -C 8 -alkoxysulfonylamino, substituted or non-substituted tri(C 1 -C 8 -alkyl)-silyl, substituted or non-substituted (C 1 -C 6 -alkylideneamino)oxy, substituted or non-substituted (C 1 -C 6 -alkenylideneamino)oxy, substituted or non-substituted (C 1 -C 6 -alkynylideneamino)oxy, substituted or non-substituted (benzylideneamino)oxy, substituted or non-substituted (N-hydroxy-C 1 -C 6 -alkanimidoyl)amino, or substituted or non-substituted (N—C 1 -C 6 -alkoxy-C 1 -C 6 -alkanimidoyl)amino;
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, or 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 cyano group, a substituted or non-substituted carbaldehyde O—(C 1 -C 8 -alkyfloxime, a pentafluoro- 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, or substituted or non-substituted heterocyclyloxy;

wherein said compound can comprise a salt, N-oxide, metallic complex and/or metalloidic complex thereof and/or an (E) and/or (Z) isomer and/or a mixture thereof.

2 . A compound according to claim 1 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.

3 . A compound according to claim 2 wherein X 1 represents a hydrogen atom, 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 substituted or non-substituted carbaldehyde O—(C 1 -C 8 -alkyl)oxime, a substituted or non-substituted (hydroxyimino)-C 1 -C 6 -alkyl group, 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 6 -alkoxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (C 1 -C 6 -alkynyloxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (benzyloxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (N-hydroxy-C 1 -C 6 -alkanimidoyl)amino, or substituted or non-substituted (N—C 1 -C 6 -alkoxy-C 1 -C 6 -alkanimidoyl)amino.

5 . A compound according to claim 4 wherein Z 1 represents 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 6 -alkoxyimino)-C 1 -C 6 -alkyl, substituted or non-substituted (C 1 -C 6 -alkenyloxyimino)-C 1 -C 6 -alkyl, subst

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A61P31/10

  Antimycotics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• A01N43/50

  1,3-Diazoles; Hydrogenated 1,3-diazoles · CPC title

• C07D413/12

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

• A01N43/82 Primary

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