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N-heteroarylmethylpyrimidinamine compound, preparation method and applications thereof

A technology of heteroarylmethylpyrimidine amines and compounds, applied in the directions of botanical equipment and methods, applications, organic chemistry, etc.

Active Publication Date: 2018-05-08
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many pest / mite and harmful bacteria control agents on the market, due to the continuous expansion of the market, foreign pests / mite and harmful bacteria, resistance of pests / mite and harmful bacteria, drug service life, drug economy and other issues As well as people's increasing attention to the environment, scientists need to continue to study, and then develop new high-efficiency, safe, economical, environmentally compatible and new varieties of insecticides / mite and fungicides with different modes of action

Method used

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  • N-heteroarylmethylpyrimidinamine compound, preparation method and applications thereof
  • N-heteroarylmethylpyrimidinamine compound, preparation method and applications thereof
  • N-heteroarylmethylpyrimidinamine compound, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Embodiment 1 This embodiment illustrates the preparation method of compound 21 in Table 1

[0087]

[0088] 4-Chloromethyl-2-(4-methylphenyl)thiazole 1.3 dichloroacetone (170mmol), 4-methylthiobenzamide (150mmol), ethanol (150mL) and THF (75mL) at reflux and After reacting for 5-8 hours under stirring conditions. Most of the solvent was removed, cooled, the reaction solution was poured into ice water, extracted with ethyl acetate, the organic phase was washed with water, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 28 g of the yellow liquid title product.

[0089] 4-aminomethyl-2-(4-methylphenyl)thiazole 4-chloromethyl-2-(4-methylphenyl)thiazole (45mmol), potassium phthalimide (50mmol) React with N,N-dimethylformamide (DMF, 100mL) at 60-80°C with stirring for 2-5 hours, then cool to room temperature, pour the reaction solution into ice water, and precipitate a solid. Filter the precipitated solid, react with hydr...

Embodiment 2

[0094] Embodiment 2 This embodiment illustrates the preparation method of compound 37 in Table 1

[0095] With reference to the method of Example 1, replace 4-methylthiobenzamide in Example 1 with 2-methylthiobenzamide, and compound 5-chloro-6-ethyl-2- Methyl-N-((2-(2-methylphenyl)thiazol-4-yl)methyl)pyrimidin-4-amine (37).

Embodiment 3

[0096] Example 3 This example illustrates the preparation of compound 273 in Table 1

[0097]

[0098] 4-Chloromethyl-2-(2-methylphenyl)oxazole 1.3 dichloroacetone (150mmol) and 2-methylbenzamide (120mmol), react 3-8 at 60-120°C with stirring After 1 hour to complete, 24.9 g of the title product was obtained as a viscous solid, which was directly used in the next step.

[0099] 4-aminomethyl-2-(2-methylphenyl) oxazole 4-chloromethyl-2-(2-methylphenyl) oxazole (120mmol), potassium phthalimide ( 150mmol) and N,N-dimethylformamide (DMF, 200mL) were reacted at 60-80°C with stirring for 6-10 hours, then cooled to room temperature, and the reaction solution was poured into ice water to precipitate a solid. Filter the precipitated solid and react with hydrazine hydrate (250mmol) and ethanol (200mL) under reflux and stirring conditions for 3-5 hours, then cool and filter. After most of the ethanol was removed from the filtrate, it was extracted with ethyl acetate, the organic pha...

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Abstract

The invention discloses an N-heteroarylmethylpyrimidinamine compound represented by a formula (I), a preparation method and applications thereof, wherein R, R<1>, R<2>, R<3>, R<4>, X and n in the formula (1) are defined in the specification. According to the present invention, the compound represented by the formula (I) has insecticidal / mite killing and / or bactericidal biological activity, and particularly provides high activity against Homoptera pests such as aphids, planthoppers and the like.

Description

technical field [0001] The invention belongs to the field of insecticide / mite and fungicides, and specifically relates to N-heteroarylmethylpyrimidinamine compounds with insecticide / mite and bactericide biological activities, their preparation method, insecticide / mite containing the compound, Fungicide composition, and use and method of controlling pests / mite and harmful germs with these compounds. Background technique [0002] The control of pests / mites and harmful germs is very important in the process of achieving efficient agriculture. At the same time, the prevention and control of pests / mite and harmful bacteria is also very important in the fields of forestry, animal husbandry, sideline, fishery and public health. Although there are many pest / mite and harmful bacteria control agents on the market, due to the continuous expansion of the market, foreign pests / mite and harmful bacteria, resistance of pests / mite and harmful bacteria, drug service life, drug economy and o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D413/12A01N43/76A01N43/78A01P7/02A01P7/04A01P1/00A01P3/00
CPCA01N43/76A01N43/78C07D413/12C07D417/12
Inventor 柳爱平刘卫东裴晖曹胜文黄丹灵任叶果项军朱锦涛李建明刘民华
Owner HUNAN CHEM RES INST