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Application of compound containing 1-(3-chloro-2-pyridyl)-1H-parazole active fragment in producing fungicide

An active fragment, pyridyl-based technology, applied in the field of pesticides, to achieve the effect of unique structure, broad-spectrum and high-efficiency bactericidal activity

Inactive Publication Date: 2019-08-16
马毅辉
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, in the prior art, there is no report that the compound containing the above-mentioned 1-(3-chloro-2-pyridyl)-1 hydrogen-pyrazole active fragment is used as an antifungal drug in the field of pesticides

Method used

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  • Application of compound containing 1-(3-chloro-2-pyridyl)-1H-parazole active fragment in producing fungicide
  • Application of compound containing 1-(3-chloro-2-pyridyl)-1H-parazole active fragment in producing fungicide
  • Application of compound containing 1-(3-chloro-2-pyridyl)-1H-parazole active fragment in producing fungicide

Examples

Experimental program
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Effect test

Embodiment 1

[0028] The preparation of embodiment 1 compound (1)

[0029] a. Add metal sodium 4.5g (200mmol) to 70ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add p-methoxyacetophenone 15g (100mmol) and diethyl oxalate 17.5g (120mmol), After the dropwise addition, stir at room temperature for 4 hours, add 2mol / L hydrochloric acid to adjust the pH value to 2-3, filter the resulting solid substance 21g of methyl p-methoxyphenyl 2,4-dicarbonylbutyrate, and the yield is 90 %;

[0030] b. Add 20g (100mmol) p-methoxyphenyl 2,4-dicarbonylbutanoic acid methyl ester and 18g (100mmol) 3-chloropyridine-2-hydrazine hydrochloride in the round-bottomed flask filled with methanol, stir After refluxing for 24 hours, solids were precipitated, filtered, and recrystallized from ethanol to obtain 28 g of the target compound, with a yield of 80%.

Embodiment 2

[0031] The preparation of embodiment 2 compound (2)

[0032] a. Add 4.5g (200mmol) of sodium metal to 70ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add 14g (100mmol) of p-fluoroacetophenone and 17.5g (120mmol) of diethyl oxalate, dropwise After completion, stir at room temperature for 4 hours, add 2 mol / L hydrochloric acid to adjust the pH value to 2-3, filter the resulting solid substance 20 g of methyl p-fluorophenyl 2,4-dicarbonyl butyrate, and the yield is 87%;

[0033] b. Add 19.6g (100mmol) methyl p-fluorophenyl 2,4-dicarbonyl butyrate and 18g (100mmol) 3-chloropyridine-2-hydrazine hydrochloride to a round-bottomed flask filled with methanol, and stir to reflux After 24 hours, solids were precipitated, filtered, and recrystallized from ethanol to obtain 25.9 g of the target compound, with a yield of 75%.

Embodiment 3

[0034] The preparation of embodiment 3 compound (3)

[0035] a. Add 4.5g (200mmol) of sodium metal to 70ml of anhydrous methanol, cool to room temperature after the reaction is complete, slowly add 13.5g (100mmol) of p-methylacetophenone and 17.5g (120mmol) of diethyl oxalate, After the dropwise addition, stir at room temperature for 4 hours, add 2 mol / L hydrochloric acid to adjust the pH value to 2-3, filter the resulting solid substance p-methylphenyl 2,4-dicarbonylbutanoic acid methyl ester 22.6g, yield 92 %;

[0036] b. Add 19.2g (100mmol) p-methylphenyl 2,4-dicarbonylbutanoic acid methyl ester and 18g (100mmol) of 3-chloropyridine-2-hydrazine hydrochloride to the round bottom flask filled with methanol and stir After reflux for 24 hours, a solid precipitated, filtered, and recrystallized from ethanol to obtain 31.4 g of the target compound, with a yield of 87%

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Abstract

The invention belongs to the technical field of pesticide, and particularly relates to application of a compound containing a 1-(3-chloro-2-pyridyl)-1H-parazole active fragment in producing agricultural fungicide. The compound is a 5-aryl-1-(3-chloro-2-pyridyl)-1H-parazole-3-formate compound, and a structure of the 5-aryl-1-(3-chloro-2-pyridyl)-1H-parazole-3-formate compound is as shown in a general formula (I), wherein R1 is selected from methyl, ethyl, propyl and isopropyl, and R2 is selected from 4-fluorophenyl, p-methoxyphenyl and p-methylphenyl. Compared with traditional agricultural fungicide, the provided compound is unique in structure, and an action mechanism is different from those of the exiting fungicide, so that the risk of cross resistance of plants with resistance to the exiting fungicide does not exist.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to the application of compounds containing 1-(3-chloro-2-pyridyl)-1 hydrogen-pyrazole active fragments in the preparation of fungicides. Background technique [0002] 1-(3-chloro-2-pyridyl)-1hydro-pyrazole (formula (4)) is an important active building block in the field of pesticide development, and is widely used in the design and development of pesticides, especially Development of insecticides. The ryanodine receptor insecticide chlorantraniliprole (formula (5)) contains this active fragment. [0003] [0004] However, in the prior art, there is no report that the compound containing the above-mentioned 1-(3-chloro-2-pyridyl)-1 hydrogen-pyrazole active fragment is used as an antifungal drug in the field of pesticides. Contents of the invention [0005] The object of the present invention is to provide the application of the compound containing 1-(3-chloro-2-...

Claims

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Application Information

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IPC IPC(8): A01N43/56A01P3/00
CPCA01N43/56
Inventor 马毅辉尹清铭郑晔
Owner 马毅辉
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