Oxime derivative and bactericide containing the same as active i

Details Oxime derivative and bactericide containing the same as active i Oxime derivative and bactericide containing the same as active i

1996-08-21

2000-04-11

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514380, 514274, 548240, 548243, 548247, 544316, C07D23112, C07D23310, C07D23361, C07D30752

Patent

active

060488859

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to an oxime derivative, particularly a heterocyclic compound substituted with .alpha.-(O-substituted oxyimino)-2-substituted benzyl, a process for producing it, intermediates therefor, and a bactericide (fungicide) containing it as an active ingredient.


BACKGROUND ART

Compounds containing .alpha.-(O-substituted oxyimino)-benzyl known so far include benzohydroxymoylazole derivatives having insecticidal activity (JP-A 1-308260, JP-A 5-1046, W092/09581, JP-A 5-331011, JP-A 5-331012, JP-A 6-41086), oxime derivatives having insecticidal activity (JP-A 3-68559), 1-azolyl-substituted oxime ethers having fungicidal activity (JP-A 60-87269), etc.
The present invention is to provide a compound having more potent fungicidal activity, higher utility, etc., than the known compounds as well as low toxicity.


DISCLOSURE OF INVENTION

The present inventors have intensively studied to achieve the above object. As a result, it has been found that a heterocyclic compound substituted with (.alpha.-(O-substituted oxyimino)-2-substituted benzyl has potent fungicidal activity. After further studies, the present invention has been completed.
The present invention provides:
1. A compound of the formula (I): ##STR2## wherein R.sup.1 is optionally substituted aryl, an optionally substituted heterocyclic group, mono or disubstituted methyleneamino, optionally substituted (substituted imino)methyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, substituted carbonyl or substituted sulfonyl; R.sup.2 is alkyl, alkenyl, alkynyl or cycloalkyl; R.sup.3 is an optionally substituted heterocyclic group; R.sup.4 is hydrogen, alkyl, alkoxy, halogen, nitro, cyano or halogenated alkyl; M is an oxygen atom, S(O)i (in which i is 0, 1 or 2), NR.sup.16 (in which R.sup.16 is hydrogen, alkyl or acyl) or a single bond; n is 0 or 1, provided that, when R.sup.3 is imidazol-1-yl or 1H-1,2,4-triazol-1-yl, n is 1; and .about. indicates an E- or Z-isomer or a mixture thereof; or a salt thereof;
2. A compound according to the above item 1, wherein the optionally substituted heterocyclic group represented by R.sup.1 is pyridyl, pyrimidinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, pyridazinyl, pyrrolyl, pyrazolyl, furyl, thienyl, imidazolyl, oxazolyl, thiazolyl, oxadiazolyl, triazolyl, quinolyl, indolyl, benzisothiazolyl, benzisoxazolyl or pyrazinyl, each of which is unsubstituted or substituted, or a salt thereof;
3. A compound according to the above item 1, wherein R.sup.1 is phenyl or a heterocyclic group, each of which is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of halogen, lower alkyl, halogenated lower alkyl, lower alkoxy, lower alkylthio, phenyl, phenoxy and nitro, or a salt thereof;
4. A compound according to the above item 1, wherein R.sup.1 is phenyl; phenyl substituted with halogen and/or lower alkyl; or pyridyl substituted with halogen and/or halogenated lower alkyl; or a salt thereof:
5. A compound according to the above item 1, wherein R.sup.1 is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 4-chloro-2-methylphenyl, 2-chloropyridin-3-yl, 3,5-dichloropyridin-2-yl, 5-trifluoromethylpyridin-2-yl, 5-trifluoromethyl-3-chloropyridin-2-yl or 3-trifluoromethyl-5-chloropyridin-2-yl, or a salt thereof;
6. A compound according to the above item 1, wherein R.sup.1 is a group of the formula (a): ##STR3## wherein R.sup.9 and R.sup.10 are the same or different and are hydrogen, optionally substituted alkyl, acyl, alkylthio, alkylsulfinyl alkylsulfonyl, optionally substituted amino, cycloalkyl, optionally substituted aryl or an optionally substituted heterocyclic group, or R.sup.9 and R.sup.10 are linked together to form a monocyclic or polycyclic ring which may contain a heteroatom, or a salt thereof;
7. A compound according to the above item 1, wherein R.sup.9 and

REFERENCES:
patent: 5206956 (1993-05-01), Clough et al.
patent: 5238956 (1993-08-01), Clough et al.

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