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2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives, method for preparing same and use of same

A technology of thiadiazole thioacetamidoaromatics and thiadiazoles, which is applied in the field of 2-amino-1,3,4-thiadiazole thioacetamidoaromatics derivatives and their preparation and application, and can solve the high price of fungicides , high toxicity of fungicides, no reports and other issues, to achieve the effect of good dispersion and suspension, fast disintegration speed and accurate measurement

Inactive Publication Date: 2010-04-28
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

First, some fungicides have the characteristics of high toxicity and high residue
Second, the price of fungicides is high, and long-term use will lead to drug resistance
[0004] At present, there are no reports on 2-amino-1,3,4-thiadiazolethioacetylaminoaromatic derivatives and 2-amino-1,3,4-thiadiazolethioacetylaminoaromatic fungicides
And the application of 2-amino-1,3,4-thiadiazole thioacetamidoaromatic compounds in water-dispersible tablets on agricultural fungicides has not been reported

Method used

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  • 2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives, method for preparing same and use of same
  • 2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives, method for preparing same and use of same
  • 2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives, method for preparing same and use of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 2-(2-Amino-1,3,4-thiadiazole-2-thio)-N-o-methylphenylacetamide (L 1 )Synthesis

[0051]

[0052]Add 0.26g (2mmol) of 2-amino-5-mercapto-1,3,4-thiadiazole and 0.11g (2mmol) of KOH and 5mL of ethanol into a 25mL single-necked round-bottomed flask, heat slightly until completely dissolved, Add 0.40g (2.2mmol) of o-methyl chloride acetanilide, TLC tracking, react for 46h, slowly pour the reaction solution into 20mL of water, let stand for half an hour, filter with suction, recrystallize with 50% ethanol, and dry in vacuo to obtain White solid with a yield of 78.6% and a melting point of 178-179°C.

[0053] Characterization of product parameters:

[0054] IR(KBr) v: 3272, 1654, 1510, 1410, 1186, 738cm -1 ; 1H NMR (DMF): δ8.95 (1H, NHCO), 8.12 (1H, benzene ring C 6 -H), 7.28 (2H, benzene ring C 3 -H,C 5 -H,), 7.12 (1H, benzene ring C 4 -H), 6.70 (2H, NH 2 ), 4.12 (2H, CH 2 S), 2.41 (3H, CH 3 ); MS m / z 281.1 (M+H)+(calcd 280.1);.

Embodiment 2

[0056] 2-(2-Amino-1,3,4-thiadiazole-2-thio)-N-phenylacetamide (L 2 )Synthesis

[0057]

[0058] The synthesis method is the same as in Example 1, using 5-methyl-2-mercapto-1,3,4-thiadiazole to react with chloroacetanilide to obtain a white solid with a yield of 61.6%. Melting point: 174-175°C.

[0059] Characterization of product parameters:

[0060] IR(KBr) v: 3300, 1664, 1518, 1232, 674cm -1 ; 1H NMR (DMF): δ9.18 (1H, NHCO), 8.55 (1H, benzene ring C 6 -H), 7.99 (1H, benzene ring-H), 7.65 (1H,), 7.40 (1H, benzene ring-H), 7.15 (3H, NH 2 ), 4.12 (2H, CH 2 S), 2.41 (3H, CH 3 ).

Embodiment 3

[0062] 2-(2-Amino-1,3,4-thiadiazole-2-sulfur)-N-(4-methylpyridin-2-yl)acetamide (L 4 )Synthesis

[0063]

[0064] The synthesis method is the same as in Example 1, using 5-methyl-2-mercapto-1,3,4-thiadiazole and 4-methyl-2-chloroacetylaminopyridine to react to obtain a white solid with a yield of 64.3%, melting point : 248-249°C.

[0065] Characterization of product parameters:

[0066] IR(KBr)υ: 3372, 1666, 1570, 1188, 812cm -1 ; 1H NMR (DMF): δ9.95 (1H, s, NHCO), 8.65 (s, 1H, pyridine ring-H), 8.03-8.04 (m, 2H, pyridine ring-H), 7.24-7.28 (b, 2H, NH 2 ), 4.07 (s, 2H, CH 2 S), 2.68(s, 3H, CH 3 ); MSm / z 282.1(M+H)+(calcd 281.1)

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Abstract

The invention relates 2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives of a general formula (I) and a method for preparing the same, pesticide composition using the same as active ingredient and use of the same in the prevention, control and treatment of Cladosporium cucumerinum Ellis & Arthur, Cladosporium fulvum and the like. The derivatives are synthesized by the reaction of 2-amino-5-mercapto-1,3,4-thiadiazole activated by an alkali and acetyl chloride-substituted aromatic hydrocarbon in a polar aprotic solvent. The compounds have high bacteriostatic activity against common plant pathogenic fungi and can be used as compound preparations in antiseptic effective dosage or added into an acceptable assistant to make the pesticide composition. Particularly, the 2-amino-1,3,4-thiadiazolethioacetamido aromatic hydrocarbon derivatives can be used to make water dispersible tablets that have remarkable protective and treatment effects on the common plant pathogenic fungi such as Cladosporium cucumerinum Ellis and Arthur and Cladosporium fulvum and are high-effective, low-residue, poisonous residue-free and widely-applicable novel green nuisanceless bactericides.

Description

technical field [0001] The invention relates to a 2-amino-1,3,4-thiadiazole thioacetamido arene derivative and its preparation method and application. Background technique [0002] About 90% of the world's pesticide patents are heterocyclic compounds. In my country, the proportion of fungicides in the three major pesticides is far lower than the world level (the average ratio of the world's three major pesticides is herbicide: insecticide: fungicide is 46.7: 28.9: 19.3, while my country's is 13.4: 72.6:10.1), which is the reason why my country's pesticides are backward. Therefore, at present, we should develop fungicides as soon as possible, increase the varieties of fungicides, and increase the output of fungicides to meet the needs of sustainable development of modern agriculture in our country. [0003] In addition, there are several aspects to the common problems of most fungicides. First, some fungicides are highly toxic and highly residual. Second, the price of fung...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/135C07D417/12A01N43/824A01N25/34A01P3/00
Inventor 王伟梁东王勇赵冰高妍
Owner SHANGHAI INST OF TECH
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