Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides

A compound of formula I:

• wherein n is 0, 1, 2, 3 or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1,
• R1 is nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, phenyl or phenoxy which may have 1 to 5 halogen atoms or 1 to 3 of the following radicals:
• halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
• or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals:
• halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
• R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.

A process for controlling harmful fungi, which comprises treating the harmful fungi, their environment or the plants or materials to be kept free of harmful fungi with a fungicidally effective amount of a compound of formula I

• wherein
• n is 0, 1, 2, 3, or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1;
• X is O or S;
• Y is a five-membered heteroaromatic ring which has 1-3 nitrogens and 2-4 carbons or 1-2 nitrogens, 1 oxygen or 1 sulfur, and 2-3 carbons which can be substituted with one or two radicals selected from the group consisting of Cl, CH3, CF3 and OCH3;
• R1 is nitro;
• cyano;
• halogen;
• C1-C4-alkyl;
• C1-C4-haloalkyl;
• C1-C4-alkoxy;
• C1-C4-haloalkoxy;
• C1-C4-alkylthio;
• phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
• or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
• R2 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted phenyl, cyano, acetyl or unsubstituted or substituted aromatic heterocycles containing one to three nitrogen and/or an oxygen or sulfur atom.

A compound of formula I:

• wherein n is 0 or 1, and wherein R1 is nitro, cyano, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, phenyl or phenoxy which may have 1 to 5 halogen atoms or 1 to 3 of the following radicals:
• halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
• or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two of the following radicals:
• halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy and C1-C4 alkylthio;
• R2 is 4-Cl—C6H4.

A compound of formula I

• wherein
• n is 0, 1, 2, 3, or 4, or, when R1 is nitro or cyano, n is 1 or 2, and wherein R1 can be the same or different if n is greater than 1;
• X is O or S;
• Y is a 1,2,4-triazole;
• R1 is nitro;
• cyano;
• halogen;
• C1-C4-alkyl;
• C1-C4-haloalkyl;
• C1-C4-alkoxy;
• C1-C4-haloalkoxy;
• C1-C4-alkylthio;
• phenyl or phenoxy, the aromatic rings may carry one to five halogen atoms or one to three radicals selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
• or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which is bonded to two adjacent C atoms of the phenyl radical and which may carry one to four halogen atoms or one or two radicals selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
• R2 is unsubstituted or substituted phenyl.