Benzylsulfide derivative, process for its production and pestici

Details Benzylsulfide derivative, process for its production and pestici Benzylsulfide derivative, process for its production and pestici

1996-12-19

1998-03-17

Lambkin, Deborah

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514354, 514357, 514639, 514247, 544239, 544240, 544224, 544241, 546343, 564 31, 564 32, 564 38, 564 42, A01N 4358, A01N 4340, C07D23702, C07C33500

Patent

active

057286990

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel benzylsulfide derivative, a process for its production and a pesticide containing it as an active ingredient.


BACKGROUND ART

Heretofore, it has been reported, for example, in U.S. Pat. No. 3,732,307 and Japanese Unexamined Patent Publications No. 122261/1979 and No. 45452/1981 that benzohydrazonophenylsulfide derivatives are useful as insecticides. However, the benzylsulfide derivative of the present invention has not been known.
In recent years, some of conventional commercial insecticides have been restricted in their use in view of problems such as the residual effects, accumulation or environmental pollution, and some have become not so effective as the pests have acquired resistance during their use for a long period of time. Therefore, it has been desired to develop a new insecticide which is highly effective at a low dose and which is excellent in safety.
The present inventors have synthesized various benzylsulfide derivatives and have studied their physiological activities. As a result, it has been found that the compound of the present invention exhibits outstanding pesticidal activities against various pests, particularly against agricultural and horticultural pests including lepidopteran injurious insects represented by diamond back (Plutella xylostella), Asiatic rice borer (Chio suppressalis) and beat armyworm (Spodoptera exigua), hemipteran injurious insects represented by brown planthopper (Nilaparvata lugens), green rice leafhopper (Nephotetlix cincticeps) and cotton aphid (Aphis gossypii) and elytron injurious insects represented by adzuki bean weevil (Callosobrunchus chinensis). The present invention has been accomplished on the basis of this discovery.


DISCLOSURE OF INVENTION

That is, the present invention provides (1) a benzylsulfide derivative of the formula (I) or its salt: ##STR2## wherein R.sup.1 is a C.sub.1-6 alkyl group, a C.sub.1-4 cyanoalkyl group, a C.sub.1-4 hydroxyalkyl group, a C.sub.3-6 cycloalkyl group, a C.sub.1-6 haloalkyl group, a C.sub.2-4 alkenyl group, a C.sub.2-4 alkynyl group, a phenyl group (which may be substituted by a halogen atom or a C.sub.1-4 alkyl group), a cyano group, a benzyl group (which may be substituted by a halogen atom), a thiazolyl group, a C.sub.1-4 alkylcarbamoyl group or a group of the formula --N(R.sup.5)R.sup.6 ; each of R.sup.2 and R.sup.3 which are independent of each other, is a hydrogen atom, a halogen atom, a cyano group, a C.sub.1-4 alkyl group, a C.sub.1-3 haloalkyl group, a C.sub.1-4 alkylthio group, a C.sub.1-4 alkylcarbonyl group, a carboxyl group, or a C.sub.1-4 alkoxycarbonyl group; or R.sup.2 and R.sup.3 may form a 3- to 6-membered ring together with the carbon atom to which they are bonded; or R.sup.1 and R.sup.2 may form a 3- to 8-membered ring having one or more hetero atoms, together with the sulfur and carbon atoms to which they are respectively bonded; R.sup.4 is a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, a C.sub.1-4 haloalkyl group, a C.sub.1-4 alkoxy group or a C.sub.1-4 haloalkoxy group; each of R.sup.5 and R.sup.6 which are independent of each other, is a hydrogen atom, a C.sub.1-6 alkyl group or a C.sub.1-4 haloalkyl group; or R.sup.5 and R.sup.6 may together form a group of the formula .dbd.CR.sup.7 R.sup.8 ; or R.sup.5 and R.sup.6 may form a 4- to 8-membered ring having one or more hetero atoms, together with the nitrogen atom to which they are bonded; R.sup.7 is a hydrogen atom, a C.sub.1-3 alkyl group or a C.sub.1-3 alkylthio group; R.sup.8 is a C.sub.1-3 alkylthio group or a C.sub.1-3 alkylamino group; or R.sup.7 and R.sup.8 may form a saturated or unsaturated 4- to 8-membered ring together with the carbon atom to which they are bonded; A is a hydrazinoaralkyl or hydrazonoaralkyl group of the formula (A1) or (A2): ##STR3## R.sup.9 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a C.sub.1-4 alkyl group, a C.sub.1-4 haloalkyl group, a C.sub.1-4 alkoxy group, a C.sub.1-4 haloalkoxy group, a C.sub.1-4 alkylthio group, a C.

REFERENCES:
patent: 3732307 (1973-05-01), Middleton et al.
Kornblum et al., Journal of the American Chemical Society, vol. 101, No. 3, pp. 647-657, 1979.

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