JPH0615531B2 - Pyrazole derivative and insecticide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a pyrazole derivative represented by the following general formula and an insecticide containing the compound as an active ingredient.

[However, X is hydrogen or a halogen atom, R ₁ is (CH ₃ ).
₂ NCH = N- or HON = CHNH-, R ₂ is hydrogen or a group R ₃ CO- (R ₃ is alkyl, alkenyl, phenyl, substituted phenyl, alkoxy, phenoxy, alkylthio, alkylamino, dialkylamino, phenylamino. Substituted phenylamino is shown). The compound of the present invention is generally synthesized as follows. That is, 3-tert-butyl-5-aminopyrazole and dimethylformamide are reacted with phosphorus oxychloride according to a conventional method to give 3-tert-butyl-5
-Dimethylaminomethyleneaminopyrazole is obtained.

This compound was further refluxed with hydroxylamine hydrochloride in methanol to give 3-tert-butyl-5
-Hydroxyiminomethyleneamino-pyrazole is obtained. Further, these compounds are further reacted with acid chloride, isocyanate, chloroformate or the like to give a nitrogen atom at the 1-position of the pyrazole ring to R ₂ in the above formula as R ₃
A compound that is CO- is obtained.

A typical synthesis example will be shown below and more specifically described.

Synthesis Example (1) 3-tert-butyl-5-dimethylaminomethyleneamino-1-methylcarbamoylpyrazole 3-tert-butyl-5-dimethylaminomethyleneaminopyrazole 1.9 g was dissolved in benzene 30 m, and methylisocyanate 0.6 g was added. In addition, the mixture was refluxed for 6 hours, cooled, washed with an aqueous solution of sodium hydrogen carbonate and water, and dehydrated and concentrated to obtain white crystals. Further, recrystallization from benzene-hexane gives 2.0 g of a target white crystal.

(2) 3-tert-butyl-5-hydroxyiminomethyleneamino-1-acetylpyrazole 3-tert-butyl-5-hydroxyiminomethyleneaminopyrazole (1.8 g) was dissolved in 50 m of tetrahydrofuran to give 0.8 g of acetyl chloride and 1.5 g of triethylamine. Plus 4
After the reaction is refluxed for an hour, the mixture is cooled, benzene is added, the mixture is washed with an aqueous sodium hydrogen carbonate solution and water, and dehydrated and concentrated to obtain a solid. When recrystallized with benzene-hexane,
1.7 g of white crystals are obtained.

A compound of the above general formula is synthesized by a similar method,
Representative compounds are illustrated in Table 1.

The compound of the present invention, as an insecticide, harmful or unpleasant pests in the fields of agriculture and horticulture and public health, for example, orthoptera such as Cobainigo, reticulates such as German cockroaches, chewing insects such as Pseudococcidae, lice such as lice Eyes, Hemiptera such as Aedes aegypti, Aphis gossypii, All-winged wing such as Pleurotus cornucopia, Lepidoptera such as Hasmonyoto and Konaga, Diptera such as housefly and onion fly, Concealed wing such as fleas, and Lepidoptera It is effective for the control of Hymenoptera, etc., and Coleoptera, such as Azuki bean weevils, Aphididae, etc.

The compound of the present invention is used as an insecticide as described above, but as it is or as a mixture with a carrier (diluent), a powder formulation,
It is used as a granule, a wettable powder, an emulsion, an oil, and other suitable agents commonly used in agricultural chemical formulations. In this case, a spreading agent, an emulsifying agent, a wetting agent, a fixing agent, etc. are appropriately used, if necessary.
Also used in combination with other types of fungicides, insecticides, herbicides, fertilizers, etc.
It can also be mixed.

Example 1 (Emulsion) Compound in Table 50 parts Xylene 15 parts Solpol (Emulsifier trade name) 35 parts The above components are mixed to form a uniform emulsion. Dilute with water before use.

Example 2 (Wettable powder) Compound in the table 20 parts Diatomaceous earth, clay mixture 75 parts Polyoxyethylene alkylphenol ether emulsifier 5 parts The above is mixed and pulverized into a wettable powder, which is suspended in water before use and sprayed. To do.

Example 3 (powder) Compound in the table 2 parts Mixture of talc and clay 98 parts The above components are mixed and pulverized to form a powder, which is sprayed as it is.

The amount used is not necessarily limited, but usually 500-1
Spray once or several times at a concentration of 000ppm.

Hereinafter, the effects of the present invention will be described in more detail by showing representative test examples, but it is needless to say that the present invention is not limited to these.

Test Example 1 Effect on adult mosquito planthoppers A chemical solution of each test compound having a concentration of 1000 ppm was prepared. Rice seedlings having a size of about 18 cm were soaked in it, air-dried, and then placed in a test tube containing 10 cc of water, and the adults of Astragalus chinensis were released. The test tube was allowed to stand in a thermostatic chamber at 25 ° C, and after 48 hours, life or death was discriminated and the mortality rate was calculated. The results are shown as an average value of 3 replicates.

Test Example 2 Effect on the eggs and adults of Nami-dani mite The melted agar was poured into a plastic cup having a diameter of 7 cm, and a kidney bean leaf cut out into a circle having a diameter of 3.5 cm was placed thereon, and after the agar had hardened, an adult Nami-dani mite was inoculated. . After leaving it in a constant temperature room at 25 ℃ for 24 hours,
The chemical solution with a concentration of 500 ppm was sprayed for 3 m. After 2 days, the life and death of the adult was discriminated and removed, and after 7 days, the life and death of the egg and the egg larva were discriminated, and the mortality rate of each was calculated.
The results are shown as an average value of 3 replicates.

Claims (2)

[Claims] 1. A general formula [However, X is hydrogen or a halogen atom, R ₁ is (CH ₃ ).
₂ NCH = N- or HON = CHNH-, R ₂ is hydrogen or a group R ₃ CO- (R ₃ is alkyl, alkenyl, phenyl, substituted phenyl, alkoxy, phenoxy, alkylthio, alkylamino, dialkylamino, phenylamino, or Substituted phenylamino is shown). ] The pyrazole derivative represented by these. 2. General formula [However, X is hydrogen or a halogen atom, R ₁ is (CH ₃ ).
₂ NCH = N- or HON = CHNH-, R ₂ is hydrogen or a group R ₃ CO- (R ₃ is alkyl, alkenyl, phenyl, substituted phenyl, alkoxy, phenoxy, alkylthio, alkylamino, dialkylamino, phenylamino, or Substituted phenylamino is shown). ] An insecticide containing the pyrazole derivative represented by the above as an active ingredient.