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Benzimidazolyl containing amide derivative, preparation method therefor and application of benzimidazolyl containing amide derivative

A technology based on benzimidazole and benzimidazole, which is applied in the field of prevention and treatment of plant fungal diseases, can solve the problems of limiting the use and development of fungicides, single targets, and long-term damage, and achieves the goal of inhibiting and preventing agricultural fungal diseases and responding Conditions are easy to control and raw materials are easy to obtain

Inactive Publication Date: 2020-02-04
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Crop diseases, especially fungal diseases, are of various types, widely distributed, spread rapidly, and difficult to control. Some types of fungal diseases also have the characteristics of wide host range, long damage period, and toxin production, which seriously affect the growth of crops and the quality of agricultural products. and safety
At present, chemical control still plays a major role in the comprehensive control of crop diseases, but the target of some existing fungicides is relatively single, coupled with long-term single use or large-scale use, the problem of fungal drug resistance has become increasingly prominent, limiting the use of fungicides And development

Method used

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  • Benzimidazolyl containing amide derivative, preparation method therefor and application of benzimidazolyl containing amide derivative
  • Benzimidazolyl containing amide derivative, preparation method therefor and application of benzimidazolyl containing amide derivative
  • Benzimidazolyl containing amide derivative, preparation method therefor and application of benzimidazolyl containing amide derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Example 1: N-(2-(1H-benzimidazol-2-yl)phenyl)-5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxamide Preparation of (I1)

[0039] 5-Chloro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid (0.52g, 3mmol) was slowly added into 10mL of thionyl chloride, refluxed for 6h, evaporated under reduced pressure to remove thionyl chloride, added 20mL of di Chloromethane, cooled to -5°C, slowly added 2-(1H-benzimidazol-2-yl)aniline (0.63g, 3mmol) in batches, added triethylamine (0.60g, 6mmol), stirred for 1h, naturally Warm up to room temperature and continue stirring for 4h. The reaction solution was washed with water, washed with saturated brine, washed with water, dried, evaporated to remove the solvent under pressure, and purified by column chromatography to obtain N-(2-(1H-benzimidazol-2-yl)phenyl)-5-chloro -1,3-Dimethyl-1H-pyrazole-4-carboxamide (I1).

Embodiment 2

[0040] Example 2: N-(2-(6-chloro-1H-benzimidazol-2-yl)phenyl)-5-chloro-1-methyl-3-trifluoromethyl-1H- Preparation of pyrazole-4-carboxamide (I8)

[0041] 5-Chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid (0.68g, 3mmol) was slowly added to 10mL of thionyl chloride, refluxed for 6h, and the thionyl chloride was distilled off under reduced pressure , add 20mL of dichloromethane, cool to -5°C, slowly add 2-(6-chloro-1H-benzimidazol-2-yl)aniline (0.73g, 3mmol) in batches, add triethylamine (0.60g, 6mmol), stirred for 1h, naturally warmed to room temperature, and continued to stir for 6h. The reaction solution was washed with water, washed with saturated brine, washed with water, dried, evaporated to remove the solvent under pressure, and purified by column chromatography to obtain N-(2-(5-chloro-1H-benzimidazol-2-yl)phenyl) -5-Chloro-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide (I8).

Embodiment 3

[0042] Example 3: Preparation of N-(2-(6-chloro-1H-benzimidazol-2-yl)phenylnicotinic acid amide (I11)

[0043] Nicotinic acid (0.37g, 3mmol) and TBTU (1.15g, 3.6mmol) were dissolved in dichloromethane, triethylamine (0.60g, 6mmol) was added, stirred for 30min, and 2-(6-chloro-1H-benzo Imidazol-2-yl)aniline (0.63g, 3mmol), continue to stir for 10h, a large amount of solids are produced in the reaction mixture, filter with suction, wash with water, and dry to obtain N-(2-(6-chloro-1H-benzimidazole- 2-yl)phenylnicotinic acid amide (I11).

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Abstract

The invention belongs to the field of pesticides and discloses a benzimidazolyl containing amide derivative, a preparation method therefor and an application of the benzimidazolyl containing amide derivative. The derivative has a structure represented by a formula (I) shown in the description. The compound disclosed by the invention is simple and convenient in preparation method, has a relativelygood inhibiting action on Gibberella zeae, Botrytis cinerea, Rhizoctonia solani and Alternaria solani and can be applied to control on fungal diseases of plants.

Description

technical field [0001] The present invention relates to the field of pesticides, in particular to an amide derivative containing a benzimidazole group, a preparation method of the derivative, and an application of the derivative in preventing and treating fungal diseases of plants. Background technique [0002] Crop diseases, especially fungal diseases, are of various types, widely distributed, spread rapidly, and difficult to control. Some types of fungal diseases also have the characteristics of wide host range, long damage period, and toxin production, which seriously affect the growth of crops and the quality of agricultural products. and safe. At present, chemical control still plays a major role in the comprehensive control of crop diseases, but the target of some existing fungicides is relatively single, coupled with long-term single use or large-scale use, the problem of fungal drug resistance has become increasingly prominent, limiting the use of fungicides And dev...

Claims

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Application Information

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IPC IPC(8): C07D403/12C07D401/12A01N43/56A01N43/52A01P3/00
CPCC07D403/12C07D401/12A01N43/56A01N43/52
Inventor 杨春龙司伟杰王濛琪
Owner NANJING AGRICULTURAL UNIVERSITY
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