Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1994-07-29
1996-06-18
Daus, Ronald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544240, A01N 4358
Patent
active
055277985
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel pyridazinone derivatives, and insecticidal and miticidal compositions containing said derivatives as an active ingredient.
PRIOR ART
Of pyridazinone derivatives, some are known as effective insecticidal and miticidal compounds. For example, Japanese Unexamined Patent Publication No. 17570/1986 discloses 2-t-butyl-4-chloro-5-(4-n-hexyl)benzylthio-3(2H)-pyridazinone, etc., and Japanese Unexamined Patent Publication No. 27736/1987 discloses 2-t-butyl-4-chloro-5-(4-vinyl)benzylthio-3(2H)-pyridazinone, etc. However, these compounds are unsatisfactory in potency.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a novel pyridazinone derivative having a high insecticidal and miticidal activity against various agricultural noxious insects.
In view of the foregoing situation, the inventors of the present invention conducted extensive research on pyridazinone derivatives to develop compounds having a high insecticidal and miticidal activity against various agricultural noxious insects and found that a pyridazinone derivative represented by the formula (1) ##STR2## wherein R is a hydrogen atom, an alkyl group, an alkoxyalkyl group or a phenyl group which may have 1 or 2 substituents in an optional position is a novel compound undisclosed in literature and has a potent insecticidal and miticidal activity. Then the inventors confirmed that the compound of the formula (1) gives a potent killing effect on resistant vermin which have caused agricultural problems and the compound has a low toxicity. The present invention has been completed on the basis of this novel finding.
The compound of the formula (1) according to the present invention is useful as an insecticidal and miticidal agent. The compound of the invention shows a particularly high insecticidal activity against noxious insects such as those of the order Lepidoptera, e.g. Adoxophyes sp., Plutella xylostella, Pieris rapae crucivora, Autographa nigrisigna, Spodoptera exigua, Spodoptera litura, etc., the order Coleoptera, e.g. Cororado potato beetle, Mexican bean beetle, etc., the order Hemiptera, e.g. Myzus persicae, Aphis gossypii, Aphis craccivora, Nephotettix cincticeps, Empoasca onukii, Laodelphax striatellus, Sogatella furcifera, Nilaparvata lugens, Trialeurodes vaporariorum, Bemisia tabaci, etc., the order Thysanoptera, e.g. Thrips palmi, Scirtothrips dorsalis, etc., the order Tetranychidae, e.g. Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, etc., the order Eriophyidae, e.g. Aculus pelekassi, etc., the order Tarsonemidae, e.g. Hemitarsonemus latus, etc.
The compound of the present invention is advantageous in effectively exterminating a wide range of vermin as compared with conventional pyridazinone derivatives. The compound of the invention displays a potent insecticidal activity also against insecticide-resistant noxious insects which conventional pyridazinone derivatives have been unable to fully control. The compound of the invention can produce an immediate insecticidal effect on, among other vermin, the order Lepidoptera such as Plutella xylostella, Spodoptera litura, etc.
The compound of the invention has also an activity to diminish the appetite of said vermin for food and an activity to hinder their growth.
The compound of the invention shows not only an activity to kill adults of said vermin but an effect of restraining their hatch.
Among the compounds of the invention, the pyridazinone derivatives of the formula (1) wherein R is a straight or branched chain alkyl group having 1 to 5 carbon atoms, preferably 4 carbon atoms, are desirable because they have a potent insecticidal effect on a wide range of noxious insects and other properties.
The compound of the invention is prepared by the process illustrated below by Reaction Scheme 1: ##STR3## wherein R is as defined above, and X is a halogen atom.
That is, the compound of the invention is prepared by reacting a pyridazinone derivative of the formula (2) with a benzyl halide of
REFERENCES:
patent: 4571397 (1986-02-01), Taniguichi
patent: 5278163 (1994-01-01), Ogura
Tada Isao
Takao Hisashi
Daus Ronald G.
Otsuka Kaguku Kabushiki Kaisha
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