Aromatic sulfur acetyl pyridine derivative and preparation method and application thereof

A technology for pyridylthioacetylaminoaromatics and derivatives, which is applied in the field of pesticide bactericidal preparations, pyridylthioacetylaminoaromatic derivatives and their preparations, and can solve the problems that the application of pyridylthioacetylaminoaromatic derivatives has not been reported, and achieve good results. Protective and therapeutic effects, easy control of reaction conditions, and simple preparation methods

Inactive Publication Date: 2010-05-12
武汉华美华科技(集团)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Pyridylthioacetylaminoaromatic derivatives of the present invention and their preparation methods and applications in pesticide fungicides have not yet been reported

Method used

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  • Aromatic sulfur acetyl pyridine derivative and preparation method and application thereof
  • Aromatic sulfur acetyl pyridine derivative and preparation method and application thereof
  • Aromatic sulfur acetyl pyridine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: 2-(pyridine-2-sulfur)-N-o-methylphenylacetamide (abbreviated as L 1 )Synthesis

[0020]

[0021] Add 0.26g (2mmol) of 2-mercaptopyridine and 5mL of ethanol (or a mixture of methanol or methanol and ethanol, the amount of which can completely dissolve 2-mercaptopyridine) into a 25mL single-necked round bottom flask, Dissolve at 30-60°C for half an hour until completely dissolved (as long as the 2-mercaptopyridine is completely dissolved, KOH or NaOH can be added for activation, not limited to half an hour or more), when the temperature is maintained at 30-50 At ℃, add 0.13g (2.4mmol) of KOH (or add 2.4mmol NaOH) to fully activate the 2-mercaptopyridine, then add 0.56g (3.2mmol) o-methyl chloride acetanilide, thin layer chromatography (TLC) follow the reaction Process, react for 36 hours, after the reaction is finished, slowly pour the reaction solution into 20mL of water (the amount of water is usually too much), let it stand for half an hour, filter it wi...

Embodiment 2

[0024] Example 2: 2-(pyridine-2-sulfur)-N-phenylacetamide (abbreviated as L 2 )Synthesis

[0025]

[0026] The synthesis method and characterization method are the same as in Example 1, except that 2-mercaptopyridine is dissolved at 40°C, the ratio of KOH to 2-mercaptopyridine is 1.2, and the activation is carried out at 30°C. The reaction between chloroacetanilide and 2-mercaptopyridine is adopted, and the ratio of the substance amount of chloroacetanilide to 2-mercaptopyridine is 1.8. The reaction finally yielded a white solid with a yield of 67.4% and a melting point of 56-57°C.

[0027] IR (KBr) v: 3324, 1674, 1578, 1438, 1116, 744cm -1 ;

[0028] 1 H NMR (CDCl 3 ): δ10.126 (b, 1H, NHCO), 7.581-8.537 (m, 1H, 2-thiopyridine ring C 6 -H), 7.587-7.554 (3H, 2-thiopyridine ring C 4 -H, benzene ring C 2 -H,C 6 -H), 7.256-7.304 (3H, 2-thiopyridine ring C 3 -H, benzene ring C 3 -H,C 5 -H), 7.039-7.138 (2H, 2-thiopyridine ring C 5 -H, benzene ring C 4 -H), 3.859-4....

Embodiment 3

[0029] Example 3: 2-(pyridine-2-sulfur)-N-p-methylphenylacetamide (abbreviated as L 3 )Synthesis

[0030]

[0031] The synthesis method and characterization method are the same as in Example 1, except that 2-mercaptopyridine is dissolved at 60°C, the ratio of KOH to 2-mercaptopyridine is 1.5, and the activation is carried out at 50°C. The reaction between p-methylchloroacetanilide and 2-mercaptopyridine is adopted, and the ratio of the substance amount of p-methylchloroacetanilide to 2-mercaptopyridine is 2.0. The reaction finally yielded a white solid with a yield of 82.7% and a melting point of 130-131°C.

[0032] IR(KBr)υ: 3296, 1654, 1446, 1148, 816cm -1 ;

[0033] 1 H NMR (CDCl 3 ): δ9.55(1H, NHCO), 8.55(1H, 2thiopyridine ring C 6 -H), 7.61 (1H, pyridine ring C 4 -H), 7.38 (2H, benzene ring C 2 -H,C 6 -H), 7.34 (1H, pyridine ring C 3 -H), 7.28 (1H, pyridine ring C 5 -H), 7.15 (2H, benzene ring C 3 -H, C5-H), 3.95 (2H, CH 2 S), 2.30 (3H, CH 3 ).

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Abstract

The invention discloses an aromatic sulfur acetyl pyridine derivative and a preparation method and application thereof. The preparation method comprises the following steps of: completely dissolving 2-mercaptopyridine with a polar protic solvent; and then adding alkali metal hydroxide for activating; and then reacting with an aromatic acetyl chloride compound; pouring products into over-dose water, allowing to stand still, and filtering, recrystallizing, and drying to obtain the aromatic sulfur acetyl pyridine derivative used as pesticide bactericide. The invention has the advantages of simple preparation method and easily controlled conditions, and obtained aromatic sulfur acetyl pyridine derivative has good effects on the prevention and the control of Bacillus anthracis of cucumber and sclerotinia sclerotiorum of rape and wild cabbage.

Description

technical field [0001] The invention relates to a pyridylthioacetylaminoaromatic derivative and its preparation method and use, in particular to the pyridylthioacetylaminoaromatic derivative and its preparation method and use as a pesticide fungicide, which belongs to the agricultural fungicide and antibacterial agent field. 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. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/70C07D213/75A01N43/40A01P3/00
Inventor 王文瀚徐薇
Owner 武汉华美华科技(集团)有限公司
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