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Pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as preparation method and application of derivatives

A technology of thiadiazole sulfide and pyrazole amide is applied in the field of pyrazole amide and pyrazole imine derivatives and their preparation, which can solve the problems of indistinct bactericidal activity in vitro and achieve a reasonable synthesis route , the effect of simple operation and low cost of synthetic raw materials

Active Publication Date: 2014-07-30
菏泽市金沃泰化工有限公司
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Problems solved by technology

[0011] In 2007, Shao Ling et al [Shao Ling, Zhang Qing, Zhou Xin, Jin Zhong, Liu Jianbing, Fang Jianxin. Chinese Journal of Advanced Chemistry. 2007, 28(2): 270-273.] synthesized compound g, and the biological activity test results showed that , the in vitro bactericidal activity of the compound was not obvious at the concentration of 50 mg / L, and some compounds had certain antibacterial activity against R. apple, but the highest antibacterial activity was only 55%.
[0017] In summary, pyrazole amides and pyrazole imines have good antibacterial activities, and 1,3,4-thiadiazole sulfide compounds also have good bactericidal activities. Introduce substituted 1,3,4-thiadiazole sulfide bonds on pyrazole imines, further explore its biological activity, and compare the structures and activities of the two types of compounds; Preparation of Pyrazole Amides and Pyrazole Imine Derivatives Substituting 1,3,4-Thiadiazole Thioethers and Their Anti-Tobacco Mosaic Virus Activity Test and Report as Anti-Tobacco Mosaic Virus Drugs

Method used

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  • Pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as preparation method and application of derivatives
  • Pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as preparation method and application of derivatives
  • Pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as preparation method and application of derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Example 1: 5-chloro-N-(5-((3-fluorobenzyl)thio)-1,3,4-thiadiazol-2-yl)-1-methyl-3-(trifluoro methyl)-1 H -pyrazole-4-carboxamide (I 1 ) preparation;

[0092] (1) Preparation of 1-methyl-3-trifluoromethyl-5-pyrazolone intermediate:

[0093] Throw 0.1 mol of methylhydrazine into a 250 mL three-necked flask, add 10 mL of absolute ethanol, stir and heat to 50 0 At about C, add 0.1 mol ethyl trifluoroacetoacetate drop by drop, heat to reflux for 5 h, cool to crystallize, filter under reduced pressure, and dry to obtain a yellow solid; yield: 85.8%.

[0094] (2) Preparation of 1-methyl-3-trifluoromethyl-5-chloro-4-pyrazole aldehyde intermediate:

[0095] Add 0.35 mol DMF to a 250 mL three-neck flask, and slowly add 0.83 mol POCl dropwise at 0 °C 3 , after dropping, stirred for 20 min, slowly added 0.10 mol 1-methyl-3-trifluoromethyl-5-pyrazolone, raised the temperature to 80-90 °C for 5 h, cooled and slowly poured into 200 mL of ice water, Stand for 2 h, filter with suc...

Embodiment 2

[0104] Example 2: 5-chloro-N-(5-((3-fluorobenzyl)thio)-1,3,4-thiadiazol-2-yl)-1-phenyl-3-(trifluoro methyl)-1 H -pyrazole-4-carboxamide (I 2 ) preparation;

[0105] (1) Preparation of 1-phenyl-3-trifluoromethyl-5-pyrazolone intermediate:

[0106] Throw 0.1 mol of phenylhydrazine into a 250 mL three-neck flask, add 10 mL of absolute ethanol, stir and heat to 50 0 At around C, add 0.1 mol ethyl trifluoroacetoacetate dropwise, heat to reflux for 5 h, cool to crystallize, filter under reduced pressure, and dry to obtain a yellow solid; yield: 83.8%.

[0107] (2) Preparation of 1-phenyl-3-trifluoromethyl-5-chloro-4-pyrazole aldehyde intermediate:

[0108] Add 0.35 mol DMF to a 250 mL three-neck flask, and slowly add 0.83 mol POCl dropwise at 0 °C 3 After dropping, stir for 20 min, slowly add 0.10 mol 1-phenyl-3-trifluoromethyl-5-pyrazolone, heat up to 80-90 °C for 5 h, cool down and slowly pour into 200 mL of ice water, Stand for 2 h, filter with suction, wash with water, an...

Embodiment 3

[0117] Example three: 5-chloro-N-(5-((4-nitrobenzyl)thio)-1,3,4-thiadiazol-2-yl)-1-methyl-3-(tri Fluoromethyl)-1 H -pyrazole-4-carboxamide (I 3 ) preparation;

[0118] (1) Preparation of 1-methyl-3-trifluoromethyl-5-pyrazolone intermediate:

[0119] It was synthesized according to the method and conditions of Example 1 (1).

[0120] (2) Preparation of 1-methyl-3-trifluoromethyl-5-chloro-4-pyrazole aldehyde intermediate:

[0121] It was synthesized according to the method and conditions of Example 1 (2).

[0122] (3) Preparation of 1-methyl-3-trifluoromethyl-5-chloro-4-pyrazole acid intermediate:

[0123] It was synthesized according to the method and conditions of Example 1 (3).

[0124] (4) Preparation of 1-methyl-3-trifluoromethyl-5-chloro-4-pyrazole chloride intermediate:

[0125]It was synthesized according to the method and conditions of Example 1 (4).

[0126] (5) Preparation of 2-amino-5-(4-nitro)benzyl-1,3,4-thiadiazole sulfide intermediate:

[0127] Add 20mm...

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Abstract

The invention discloses pyrazole amide and pyrazole imine derivatives containing substituted 1, 3, 4-thiadiazole thioether as well as a preparation method and an application of the derivatives. The compounds have the structures as shown in formulae (I) and (II). The preparation method comprises the following steps: by taking substituted hydrazine as an initial raw material, carrying out closed loop, chlorine formylation, oxidation and chloro reaction to obtain pyrazole acyl chloride; carrying out a reaction on 2-amino-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to obtain 2-amino-5-substituted 1, 3, 4-thiadiazole thioether; and then, carrying out a substitution reaction on 2-amino-5-substituted 1, 3, 4-thiadiazole thioether and substituted pyrazole acyl chloride to obtain the pyrazole amide compound (I) containing substituted 1, 3, 4-thiadiazole thioether; by taking substituted hydrazine as an initial raw material, carrying out closed loop and chlorine formylation to obtain pyrazole aldehyde; carrying out an additive elimination reaction on pyrazole aldehyde and 2-amino-5-mercapto-1, 3, 4-thiadiazole under a backflow condition of anhydrous ethanol to obtain 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole; and then carrying out a reaction on 2-substituted pyrazole imidogen-5-mercapto-1, 3, 4-thiadiazole and substituted benzyl chloride to generate the pyrazole imine compound (II) containing substituted 1, 3, 4-thiadiazole thioether. The compounds disclosed by the invention have a good inhibiting effect on tobacco mosaic virus and can be used for preparing anti-plant virus drugs.

Description

technical field [0001] The invention relates to chemical industry and pesticides, and the specific technology is pyrazole amides and pyrazole imine derivatives containing substituted 1,3,4-thiadiazole sulfide derivatives, their preparation method and application. Background technique [0002] Viral diseases are important diseases that occur in many crops. According to statistics, the direct economic losses caused by viral diseases in the world reach more than 15 billion U.S. dollars every year. There is a significant difference between virus damage to plants and other pathogens, that is, after virus particles enter the plant body through other factors, such as insects, plant wounds caused by artificial or natural factors, etc., they use the information, energy and enzyme systems of plant cells to complete the virus itself. This multiplication mechanism of plant viruses has brought great difficulties to the prevention and treatment of viral diseases. [0003] In 1999, Chen e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12A01N43/824A01P1/00
CPCA01N43/82C07D417/12C07D417/14
Inventor 薛伟龚华玉王忠波张贤柳敏朱雪松夏丽娟赵洪菊陈玉
Owner 菏泽市金沃泰化工有限公司
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