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New [1,2,3]-thiobiazole derivative and its synthesis 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.

Active Publication Date: 2006-08-02
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 further search for more For novel TDL derivatives with high inducing activity, we fit different types of novel [1, 2, 3] thiadiazole derivatives that have not been reported in literature and patents, and screen for inducing disease resistance and other biological activities

Method used

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  • New [1,2,3]-thiobiazole derivative and its synthesis and use
  • New [1,2,3]-thiobiazole derivative and its synthesis and use
  • New [1,2,3]-thiobiazole derivative and its synthesis and use

Examples

Experimental program
Comparison scheme
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 bottom flask equipped with a condensing reflux tube, reflux at 50°C for 20 minutes, then stir at 25°C for 20 minutes After 1 hour, the methanol, water and a small amount of unreacted dimethyl carbonate were evaporated under reduced pressure with 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] Add 7.28g (0.06mol) of ethyl acetoacetate and 3.7mL of ethanol solution into a 50mL three-neck flask, and slowly add dropwise a solution of 5.02g (0.06mol) of methyl carbazate and 16.7mL of ethanol 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 44mL of thionyl chloride to a 250mL three-necked flask equipped with a drying tube and an exhaust gas absorption device, and slowly add 40.57g (0.20mol) of 3-(methoxycarbonylhydrazone)-butyric acid ethyl Esters and 45ml of dichloromethane solution, control the temperature below 20 ° C. 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, 76-78 ° C, with a yield of 75%.

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Abstract

The present invention provides one kind of 1, 2, 3-thiobiazole-5-formamide compounds and their synthesis process and pesticide bioactivity screening. The screening system includes the determination of tobacco mosaic disease resisting activity, tobacco mosaic disease virus resistance inducing activity, and pesticidal and fungus-inhibiting activity. The related compounds are 1, 2, 3-thiobiazole-5-formamide derivatives with the general expression as shown, and include 7 hetero cycle containing 1, 2, 3-thiobiazole-5-formamide derivatives, 2 benzene ring containing 1, 2, 3-thiobiazole-5-formamide derivatives, and 2 aliphatic radical containing 1, 2, 3-thiobiazole-5-formamide derivatives.

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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Patent Type & Authority Applications(China)
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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