Benzohydroximoylazole derivatives and insecticide including the

Details Benzohydroximoylazole derivatives and insecticide including the Benzohydroximoylazole derivatives and insecticide including the

1992-07-28

1994-11-22

Morris, Patricia L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514 63, 548110, 5482624, A01N 43653, C07D24908

Patent

active

053669886

DESCRIPTION:

BRIEF SUMMARY
RELATED APPLICATIONS

This application was filed as PCT application No. PCT/JP91/01614 on Nov. 25, 1991.
1. Field of the Invention
The present invention relates to a benzohydroximoylazole derivative and to an insecticide containing the same as an active ingredient.
2. Background of the Invention
Heretofore, it has been known that compounds such as 1-(O-ethyl-4-butylbenzohydroximoyl)-1H-1,2,4-triazole and the like have insecticidal activities (for example, as described in Japanese Patent Application First Publication No. 1-308260).


Disclosure of the Invention

Such compounds disclosed in the above-mentioned patent application do not have the sufficient insecticidal effect. Recently, strains of harmful insects exhibiting resistance to conventional insecticides have appeared due no extensive and prolonged use thereof, and for this reason, the effectiveness of conventional insecticides are being lowered. In particular, the harmful insects in the order hemiptera such as the Delphacidae, Deltocephalidae, Aphididae, Pseudococcidae, Aleyrodidae, Pentatomidae, and the like have caused considerable damage to trees and to crops such as rice, wheat, potatoes, and the like.
Therefore, it is desirable to develop an insecticide having both superior insecticidal effect at low rates of application and effectiveness against the resistant strains of harmful insects described above.
The present inventors have synthesized various benzohydroximoylazole derivatives and have carried out extensive research in connection with the physiological activities thereof. As a result, they have found that the compounds according to the present invention wherein special substituents are bonded to the phenyl rings of the benzohydroximoylazole derivatives have extremely superior insecticidal activities against the various harmful insects, especially the harmful hemiptera such as Delphacidae, Deltocephalidae, Aphididae, Pentatomidae, and the like. The insecticidal activities of the compounds according to the present invention are superior to those of the compounds disclosed in Japanese Patent Application First Publication No. 1-308260. In addition, the compounds of the present invention exhibit improved insecticidal activities against the harmful resistant insects described above.
The present invention provides the following benzohydroximoylazol derivatives represented by formula [I] and an insecticide including the same as an active ingredient: ##STR2## wherein R is a branched alkyl group having not fewer than 3 carbon atoms, a fluorine-substituted alkyl group having not fewer than 2 carbon atoms, a branched alkoxy group having not fewer than 3 carbon atoms, a halogen-substituted alkoxy group having not fewer than 3 carbon atoms, a cycloalkyl group, a cycloalkylmethyl group which may be substituted with one or two alkyl groups, a substituted silylalkyl group, a substituted silylalkyloxy group, a cycloalkyloxy group which may be substituted with one or two alkyl groups, an alkylthio group, a halogen-substituted alkyloxyalkyl group, an alkynyl group, or a halogen-substituted alkenyloxy group;
In formula [I], a branched alkyl group having not fewer than 3 carbon atoms includes, for example, isopropyl, isobutyl, s-butyl, t-butyl, isopentyl, 1-methylbutyl, 2-methylbutyl, neopentyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 5-methylhexyl, 3,3-dimethylpentyl, 4,4-dimethylpentyl, 1,3,3-trimethylbutyl, 2,3,3-trimethylbutyl, 3,3-dimethylhexyl, 1,1,3,3-tetramethylbutyl, or the like.
A branched alkoxy group having not fewer than 3 carbon atoms includes, for example, isopropoxy, isobutoxy, s-butoxy, t-butoxy, i-pentyloxy, neopentyloxy, 1-methylbutoxy, 2-methylbutoxy, 1,2-dimethylpropoxy, 2-ethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 2,3,3-trimethylpropoxy, 2,2-dimethylpentyloxy, 1,3,3-trimethylbutoxy, 1-ethyl-2,2-dimethylpropoxy, 1-isopropoxy-2-methylpropoxy, or the like.
A fluorine-substituted alkyl group having not fewer than 2 carbon atoms includes, for example, perfluor

REFERENCES:
patent: 4360526 (1982-11-01), Zeeh et al.
patent: 4599348 (1986-07-01), Schmetzer et al.
patent: 4771065 (1988-09-01), Kramer et al.
Hokari et al.; "Preparation of hydroximoylimidazoles, etc" CA 116:2318 x (1992).

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