Method for preparing N-alkoxy carbonyl, thiazolethioketone derivative,s and usage

A technology of oxycarbonyl and thiazolethione, applied in the field of N-oxycarbonyl-2-thiazolethione derivatives, can solve the biological activity research of rare N-oxycarbonyl-2-thiazolethione derivatives And other issues

Inactive Publication Date: 2006-04-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, there are few literature reports on the synthesis and biological activity of N-alkoxycarbonyl-2-thiazolethione derivatives

Method used

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  • Method for preparing N-alkoxy carbonyl, thiazolethioketone derivative,s and usage
  • Method for preparing N-alkoxy carbonyl, thiazolethioketone derivative,s and usage
  • Method for preparing N-alkoxy carbonyl, thiazolethioketone derivative,s and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Synthesis of N-pentyloxycarbonyl-2-thiazolethione

[0025] Add 19.8g (0.067mol) of bis(trichloromethyl)carbonate and 50ml of dichloromethane into a 250ml three-necked flask, and slowly add n-amyl alcohol (0.2mol) under stirring. Under cooling in an ice bath, a solution of triethylamine (0.2 mol) and 10 ml of dichloromethane was slowly added dropwise, maintaining the temperature between 0 and 5°C. After the dropwise addition was completed, the temperature was raised slowly and stirred at 20° C. for 2 hours. Wash with water three times (3×50ml), dry over anhydrous sodium sulfate, filter, concentrate, and distill out n-pentyl chloroformate under reduced pressure. Yield 85.6%.

[0026] Tetrahydrothiazole-2-thione (0.60 g, 5 mmol) and triethylamine (0.72 g, 7 mmol) were dissolved in 10 ml of dichloromethane and stirred. Under cooling in an ice bath, the above n-amyl chloroformate (6 mmol) was added dropwise. After the dropwise addition, react at 0-10°C for 4 ho...

Embodiment 2

[0030] Embodiment 2 Synthesis of N-isoamyloxycarbonyl-2-thiazolethione

[0031] Add 19.8 g (0.067 mol) of bis(trichloromethyl) carbonate and 50 ml of chloroform into a 250 ml three-neck flask, and slowly add isoamyl alcohol (0.2 mol) while stirring. Under cooling in an ice bath, a solution of pyridine (0.2 mol) and 10 ml of chloroform was slowly added dropwise, maintaining the temperature between 0 and 5°C. After the dropwise addition was completed, the temperature was raised slowly and stirred at 25° C. for 2 hours. Wash with water three times (3×50ml), dry over anhydrous sodium sulfate, filter, concentrate, and evaporate isoamyl chloroformate under reduced pressure. Yield 82.7%.

[0032] Tetrahydrothiazole-2-thione (0.60 g, 5 mmol) and triethylamine (0.82 g, 8 mmol) were dissolved in 15 ml of dichloromethane and stirred. Under cooling in an ice bath, the above-mentioned isoamyl chloroformate (6 mmol) was added dropwise. After the dropwise addition, react at 0-10°C for 10...

Embodiment 3

[0036] Example 3 Synthesis of N-n-butoxycarbonyl-2-thiazolethione

[0037] N-pentanol is replaced by n-butanol, and others are the same as in Example 1 to obtain n-butyl chloroformate. Yield 88.3%.

[0038] Tetrahydrothiazole-2-thione (0.60 g, 5 mmol) and pyridine (0.56 g, 7 mmol) were dissolved in 10 ml of chloroform and stirred. Under cooling in an ice bath, the above n-butyl chloroformate (6 mmol) was added dropwise. After the dropwise addition, react at 0-10°C for 3 hours. Washed three times with water, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was separated and purified by column chromatography [V (petroleum ether): V (ethyl acetate) = 3: 1] to obtain 0.95 g of N-butoxycarbonyl-2-thiazolethione as a yellow transparent oil. The yield was 87.0%.

[0039] of the compound 1 H NMR and IR are as follows:

[0040] 1 H NMR (CDCl 3 )δ: 0.95(t, 3H, J=4.8Hz, -CH 2 CH 2 CH 2 CH 3 ), 1.41~1.47 (m, 2H, -CH 2 CH 2 CH 2 CH 3 ), 1.69~1.73 (...

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Abstract

A N-hydrocarbyloxycarbonyl-2-thiazolethione derivative is prepared through condensation reaction between 2-thiazolethione and chlorocarbonate in organic solvent under existence of acid capture, and post-treating. It can be used as the insecticide for red spider and the bactericide for gray mold, powdery mildew, etc.

Description

(1) Technical field [0001] The invention relates to an N-alkoxycarbonyl-2-thiazolethione derivative, a preparation method and use thereof. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. Thiazole compounds are a category that has developed rapidly in recent years, and many commercial insecticides, fungicides, and herbicides belong to this category. For example, the systemic insecticide thiazophos developed by Ishihara Industry Company of Japan has a strong ability to kill various pests that have developed resistance to traditional insecticides; Fenconazole is a systemic fungicide that inhibits the formation of infected filaments on epispora and prevents rice blast. [0003] 2-thiazolethione is not only a useful organic intermediate, but also has certain bactericidal activity itself. At the same time, existing literat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/16A01N43/78A01P3/00
Inventor 翁建全沈德隆谭成侠曹耀艳
Owner ZHEJIANG UNIV OF TECH
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