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N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound and application thereof

A pyrazole carboxamide and disubstituted technology, applied in the field of medicinal chemistry, can solve the problems of yield reduction and human health threat, and achieve the effects of good bacteriostatic activity, excellent bacteriostatic activity, excellent protection and therapeutic activity

Pending Publication Date: 2022-07-15
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Plant fungal diseases have led to a 20% annual reduction in the production of major food and economic crops around the world; in addition, some fungi can also produce mycotoxins, which pose a major threat to human health

Method used

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  • N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound and application thereof
  • N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound and application thereof
  • N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound and application thereof

Examples

Experimental program
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Effect test

Embodiment Construction

[0014] Synthesis of a class of N-heterocycle-1,5-disubstituted-4-pyrazole carboxamides:

[0015]

[0016] Using substituted ethyl acetoacetate (A) as the starting material, the target compound E is synthesized through ring closure, hydrolysis, acyl chloride and substitution reaction.

[0017] Preparation of Intermediate B: Taking 1-(2-Fluoro-phenyl)-5-monochloromethyl-1H-4-pyrazolecarboxylic acid ethyl ester as an example

[0018]

[0019] In a round bottom flask, ethyl monochloroacetoacetate (0.1 mol), triethyl orthoformate (0.2 mol) and acetic anhydride (0.3 mol) were mixed, stirred at 130°C for 4 hours, and then distilled under reduced pressure to obtain an intermediate body. o-Fluorophenylhydrazine (7.9 g, 49.5 mmol) was dissolved in ethanol (100 mL), the intermediate was added, and the reaction was carried out at 100° C. for 2 hours. The solvent was removed by distillation under reduced pressure, the mixture was extracted with ethyl acetate, washed with brine, dri...

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Abstract

The invention discloses an N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound, which is characterized in that the structural formula of the N-heterocycl-1, 5-disubstituted-4-pyrazolecarboxamide compound is shown in the specification, wherein R1 is methyl, monochloromethyl, difluoromethyl, trifluoromethyl or trichloromethyl; r2 is isopropyl, tertiary butyl, cyclohexyl, phenyl or o-substituted phenyl; r < 3 > is 4-pyridyl, 2-substituted-4-pyridyl, 3-thienyl or 2-substituted-3-thienyl. The formula (I) is shown in the description. The compounds not only have excellent activity on fusarium graminearum and rice black fungus which cause fungal diseases of rice, but also have good bacteriostatic activity on various plant pathogens by part of the compounds, and have obvious broad-spectrum activity. In addition, part of the compounds show excellent protection and treatment activity on corn plants infected by fusarium graminearum pathogenic bacteria and rice plants infected by rice black fungus pathogenic bacteria.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of N-heterocycle-1,5-disubstituted-4-pyrazolecarboxamide compounds and their application in anti-phytopathogenic fungi. Background technique [0002] Plant fungal diseases reduce the production of major food and cash crops worldwide by up to 20% annually; in addition, some fungi can also produce mycotoxins, posing a major threat to human health. However, chemical means is still the main method to prevent and control fungal diseases. Among them, fungicides play an important role in protecting agricultural production and promoting stable grain income. In recent years, major pesticide companies have made rapid progress in the research and development of fungicides with new structures, and obtained a variety of fungicides with new mechanisms of action, such as fungicides that interfere with the synthesis of metabolites, affect cell structure, and hinder respiration, etc. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D409/12A01N43/56A01P3/00
CPCC07D401/12C07D409/12A01N43/56
Inventor 吴志兵杨晶欣张承志谢德文杨松薛伟
Owner GUIZHOU UNIV
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