Pyrazole derivatives and insecticidal compositions containing th

Details Pyrazole derivatives and insecticidal compositions containing th Pyrazole derivatives and insecticidal compositions containing th

1997-06-10

1998-04-14

Ramsuer, Robert W.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

5462761, 5483664, 5483661, 5483674, 5483681, 5483701, 5483704, 5483711, A61K 31415, C07D23120

Patent

active

057390835

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP96/02946 filed Oct. 9, 1996.


TECHNICAL FIELD

The present invention relates to pyrazole derivatives and insecticidal compositions containing the derivative as their active component.


BACKGROUND ART

With insecticides in use for many years, pest insects have acquired resistance in recent years and become difficult to control with conventional insecticides. Some of the insecticides have a high toxicity and some are persistent, disturbing the ecological system. Accordingly it is expected to develop novel insecticides having a low toxicity and less persistence.
Up to date, some types of pyrazole derivatives are known to have herbicidal activity. For example, JP-A-163063/1991 discloses 3-phenyl-5-alkylsulfenylpyrazoles. 5-Phenyl-3-alkylsulfenylpyrazoles are also disclosed in JP-A-509103/1993. However, no studies whatever have been conducted on the insecticidal activity of these compounds and analogues thereof.
An object of the present invention is to provide novel insecticides which are low in toxicity and persistence and yet have an extremely high insecticidal efficacy.


DISCLOSURE OF THE INVENTION

The present invention provides pyrazole derivatives represented by the formula (1), and an insecticidal composition comprising the derivative as its active component ##STR2## wherein A is CH, N or C-halogen atom, R.sup.1 is hydrogen atom, lower alkyl, lower haloalkyl, benzyl or phenyl, R.sup.2 is lower alkyl, lower haloalkyl, lower alkenyl, lower alkynyl, benzyl or phenyl, R.sup.3 is hydrogen atom, a halogen atom, lower alkyl, lower haloalkylthio, phenyl, cyano, nitro or amino, R.sup.4 is halogen atom, R.sup.5 is lower haloalkyl, R.sup.6 is hydrogen atom, lower alkyl, lower haloalkyl or benzyl, R.sup.1 and R.sup.6 being not hydrogen atoms at the same time, 1 is 0 or 1, m is 0 or 1 and n is a number of 0 to 2.
The inventors of the present invention have conducted detailed research on the insecticidal activity of pyrazole derivatives. Consequently, they have found that the pyrazole derivatives of the formula (1) are very useful compounds having very high insecticidal activity but almost no injury to mammals, fishes, crustaceans and beneficial insects such as honeybees and accomplished the present invention.
When used at a low dose or concentration, the compounds of the present invention effectively control pest insects of the orders Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera and Isoptera, mites and lice. More specific examples of harmful organisms controllable with the compound of the invention are agricultural harmful insects such as Nephotettix cincticeps, Nilaparvata lugens, Myzus persicae, Epilachna vigintioctopunctata, Spodoptera litura, Cnaphalocrocis medinalis and Plutlla xylostella, spider mites such as Tetranychus urticae, Panonychus citri and Tetranychus kanzawai, sanitary insect pest such as Culex pipfens pallens, Musca domestica, Blattella germanica, ants, fleas and lice, insects harmful to storage such as Sitophilus oryzae, Tribolium castaneum and Ephestia cautella, household harmful insects such as termites, insects harmful to cattle such as mites, fleas and lice, household mites such as acarid mites, house dust mites, cheyletid mites, and mollusks such as slugs and snails.
The compounds (1) of the invention include the compounds (1A) and (1B) given below ##STR3## wherein A and R.sup.1 to R.sup.5 are the same as above ##STR4## wherein A and R.sup.2 to R.sup.6 are the same as above.
Examples of each group shown by A, R.sup.1 .about.R.sup.6 in the formula (1) are as follows.
Halogen atoms include fluorine, chlorine, bromine and iodine atoms. Lower alkyl groups are preferably straight-chain or branched alkyl having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl and hexyl. Lower haloalkyl groups are preferably straight-chain or branched haloalkyl having 1 to 6 carbon atoms in which the above halogen atom is substituted on the above alkyl group. Lower alkenyl groups are preferab

REFERENCES:
WO 92/02509, Feb. 1992, Mischke et al.
Brunner et al, Chemical Abstracts, vol. 126 No. 144273 (1997).

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