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Pyrazole compound containing chrysanthemic acid structure and preparation method and purpose of pyrazole compound

A compound, technology of pyrazoles

Active Publication Date: 2015-08-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, there is no report of pyrazole compounds containing chrysanthemic acid structure as shown in the general formula I of the present invention

Method used

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  • Pyrazole compound containing chrysanthemic acid structure and preparation method and purpose of pyrazole compound
  • Pyrazole compound containing chrysanthemic acid structure and preparation method and purpose of pyrazole compound
  • Pyrazole compound containing chrysanthemic acid structure and preparation method and purpose of pyrazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This example illustrates the preparation of 5-amino-1-(2-fluorophenyl)-3-cyano-1H-pyrazole

[0032] Add 0.01 mol of 2-fluoroaniline aniline, 5 ml of ethanol and 3.0 ml (0.035 mol) of concentrated hydrochloric acid into a four-necked flask under ice-salt bath conditions. Slowly drop 0.018mol sodium nitrite and 10ml aqueous solution into the reaction flask, and react for 0.5h after the addition to obtain a yellow diazonium salt solution.

[0033] Add 0.01mol ethyl 2,3-dicyanopropionate into the three-necked flask, slowly drop the above diazonium salt solution into the flask, and react for 2 hours. Add ammonia water to adjust the pH to 9-10, and react at room temperature for 2 hours. After the reaction was completed, it was extracted with 40ml of ethyl acetate, the organic phase was washed with water (2×30mL), washed with saturated sodium chloride solution (1×40mL), dried over anhydrous sodium sulfate, and part of the solvent was removed by rotary evaporation, and 2.13g o...

Embodiment 2

[0035] This example illustrates that N-(5-(3-cyano-1-(2-fluorophenyl)-1-H-pyrazole)carbamoyl)-3-(2-chloro-3,3,3-tri Preparation of fluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxamide

[0036] Add 0.01mol 5-amino-1-(2-fluorophenyl)-3-cyano-1H-pyrazole and 40ml toluene into a four-neck flask, heat to 90°C, add 3-(2-chloro-3 dropwise, 3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropaneformyl isocyanate 0.01mol and 5ml toluene solution, reflux reaction for 5h. After the reaction, cooling and crystallization, filtration, and recrystallization of the filter cake with ethanol to obtain 3.77 g of the product. Yield 80.2%. Product melting point: 155-156°C; 1 H NMR (DMSO-d 6 , δ): 1.12 (s, 3H, -CH 3 ), 1.25(s, 3H, -CH 3 ), 2.28 (s, 2H, cyclopropane-CH), 6.87 (s, 1H, pyrazole-CH), 7.10 (m, 1H, C=CH), 7.48-7.51 (d, J=6.3Hz, 2H, Ph- H), 7.67-7.69 (d, J=6Hz, 2H, Ph-H), 10.81 (s, 1H, CO-NH), 11.36 (s, 1H, CO-NH-CO).

Embodiment 3

[0038] This example illustrates the preparation of 5-amino-1-phenyl-3-cyano-1H-pyrazole

[0039] Add 0.01 mol of aniline, 5 ml of ethanol and 3.0 ml (0.035 mol) of concentrated hydrochloric acid into a four-necked flask under ice-salt bath conditions. Slowly drop 0.018mol sodium nitrite and 10ml aqueous solution into the reaction flask, and react for 0.5h after the addition to obtain a yellow diazonium salt solution. .

[0040] Add 0.01mol ethyl 2,3-dicyanopropionate into the three-necked flask, slowly drop the above diazonium salt solution into the flask, and react for 2 hours. Add ammonia water to adjust the pH to 9-10, and react at room temperature for 2 hours. After the reaction was completed, it was extracted with 40ml of ethyl acetate, the organic phase was washed with water (2×30mL), washed with saturated sodium chloride solution (1×40mL), dried over anhydrous sodium sulfate, and part of the solvent was removed by rotary evaporation, and 2.89g of the product was obtai...

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Abstract

The invention discloses a pyrazole compound containing chrysanthemic acid structure and a preparation method and purpose of the pyrazole compound with the general structural formula (I). The definition of each substituent group in the general structural formula (I) is showed in the description and claims. The pyrazole compound is good in insect killing effect, simple in production process and high in yield.

Description

technical field [0001] The invention belongs to the field of pesticides and insecticides. Specifically, it relates to a pyrazole compound containing a chrysanthemic acid structure, a preparation method and an application. Background technique [0002] In the application of pesticides, pyrazole compounds have insecticidal, bactericidal and herbicidal activities, and exhibit high efficiency, low toxicity and structural diversity. Such as the insecticide Kung Fu Chin, cypermethrin and so on. [0003] The latest research on the mechanism of action of pyrethroids shows that although they are different from DDT in chemical structure, they both have a similar mechanism of action in the nervous system. After further analysis, people found that the mechanism of action of pyrethroid compounds is mainly to make the sodium ion channel open for a long time, which leads to the death of excessive excitement of pests. Studies have also shown that one of the main reasons why pyrethroid pe...

Claims

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Application Information

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IPC IPC(8): C07D231/40A01N53/12A01P7/04
CPCA01N53/00C07D231/40
Inventor 万嵘秦小飞沈陈郭春伟吴少华韩振禹陈福立
Owner NANJING UNIV OF TECH
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