[1,2,3]-thiobizole derivative and its synthesis process and use

A technology of thiadiazole derivatives and synthesis methods, applied in the field of [1], can solve the problems of few reports on the screening of induced disease-resistant activity, etc.

Inactive Publication Date: 2007-11-07
LIER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Among the [1,2,3]thiadiazole derivatives disclosed in domestic and foreign patent documents, amide derivatives have been reported, but there are few reports on the screening of such compounds to induce disease resistance activity. In order to furthe

Method used

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  • [1,2,3]-thiobizole derivative and its synthesis process and use
  • [1,2,3]-thiobizole derivative and its synthesis process and use
  • [1,2,3]-thiobizole derivative and its synthesis process and use

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Preparation of methyl carbazate

[0041] Add 9 g (0.1 mol) of dimethyl carbonate and 5.4 ml (0.095 mol) of 85% hydrazine hydrate into a 50 ml round-bottomed flask equipped with a condensing reflux tube, reflux at 50°C for 20 minutes, and then stir at 25°C After 20 hours, methanol, water and a small amount of unreacted dimethyl carbonate were evaporated under reduced pressure by a water pump, and the residue was dried to obtain 8.1 g of white crystals, with a yield of 95%.

Embodiment 2

[0043] Preparation of 3-(methoxycarbonylhydrazone)-butyric acid ethyl ester

[0044] A solution of 7.28 g (0.06 mol) of ethyl acetoacetate and 3.7 ml of ethanol was added to a 50 ml three-neck flask, and a solution of 5.02 g (0.06 mol) of methyl carbazate and 16.7 ml of ethanol was slowly added dropwise at room temperature. After the addition, the mixture was stirred at room temperature for 6 hours, and the ethanol was evaporated under reduced pressure to obtain 11.26 g of a white solid with a yield of 100%.

Embodiment 3

[0046] Preparation of ethyl 4-methyl-1,2,3-thiadiazole-5-carboxylate

[0047] Add 44 milliliters of thionyl chloride to a 250 milliliter three-necked flask equipped with a drying tube and an exhaust gas absorption device, and slowly add 40.57 g (0.20 moles) of 3-(methoxycarbonylhydrazone)-butylene under ice-salt bath cooling Ethyl acetate and 45 ml of dichloromethane solution, control the temperature below 20 degrees. After the addition was complete, the mixture was stirred at room temperature for 20 hours. The excess thionyl chloride was first distilled off under normal pressure, and then distilled under reduced pressure to obtain 25.94 g of a light yellow fraction at 400 Pa, 76 to 78 degrees, with a yield of 75%.

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Abstract

The present invention relates to heterocyclic 1, 2-diazole compound, is especially 1, 2, 3-thiabiazole compounds, including 8 types of 1, 2, 3-thiabiazole-5-formamide derivative and their synthesis and farm chemical activity screening, including screening in tobacco mosaic virus (TMV) resisting activity, TMV resistance inducing activity, pesticidal activity and bacteriostasis activity. The present invention also discloses the use and usage of said compounds in resisting TMV, inducing TMV resistance, killing pests and inhibiting plant pathogenic fungi.

Description

technical field [0001] The technical scheme of the present invention relates to heterocyclic compounds containing 1,2-oxadiazole, in particular to [1,2,3]thiadiazole derivatives. Background technique [0002] Thiadiazole derivatives are important pharmaceutical and pesticide intermediates, thiadiazoles include [1,2,3]thiadiazole, [1,2,4]thiadiazole, [1,2,5]thiadiazole , [1,3,4] thiadiazole 4 isomers, each isomer has a commercial variety in pesticides, the most widely used is the derivative of [1,3,4] thiadiazole , [1, 2, 3] thiadiazole derivatives reported relatively few biological activities, but [1, 2, 3] thiadiazole derivatives have been used in agriculture, industry and medicine, because [1 , 2,3] The thiadiazole ring is the only one among several isomers that can easily generate N through pyrolysis and photolysis 2 The isomers of [1, 2, 3] thiadiazoles are therefore becoming research hotspots in the era of increasing environmental protection concerns. [1,2,3]-Thiadia...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D285/06A01N43/828A01P21/00A01P3/00
Inventor 范志金石祖贵刘秀峰范志银艾应伟
Owner LIER CHEM CO LTD
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