Halobenzene cyano pyrazol compound with insecticidal action as well as preparation method and application

A compound and a technology for preparing pesticides, applied in the field of pesticides, can solve problems such as low drug resistance

Inactive Publication Date: 2013-06-19
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, foreign drug resistance monitoring has found that field populations of Homoptera insects such as whitefly, diamondback moth, Spodoptera litura, Chiloborer, cotton bollworm, etc. have produced varying degrees of resistance to mainstream insecticides such as fipronil drug resistance
In my country, fipronil was promoted and used in 1996, but in less than 2 years, diamondback moths developed low-level resistance to it

Method used

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  • Halobenzene cyano pyrazol compound with insecticidal action as well as preparation method and application
  • Halobenzene cyano pyrazol compound with insecticidal action as well as preparation method and application
  • Halobenzene cyano pyrazol compound with insecticidal action as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] This example illustrates the preparation of 5-amino-1-(4-fluorophenyl)-3-cyano-1H-pyrazole

[0046] Add 0.01 mol of 4-fluoroaniline and a small amount of ethanol to a 250 ml round-bottomed three-neck flask, and add 3.0 ml (0.035 mol) of concentrated hydrochloric acid dropwise with stirring under ice-bath conditions. Dissolve 0.018mol of sodium nitrite in 10ml of water, slowly drop it into the flask, and react for 0.5h after the dropwise addition to obtain a yellow diazonium salt solution.

[0047] Add 0.01mol ethyl 2,3-dicyanopropionate into the three-necked flask, drop the prepared diazonium salt solution into the flask, and react for 2 hours after the dropwise addition. Add ammonia water, 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 dichloromethane, the organic layer was washed with water (2×30mL), washed with saturated sodium chloride solution (1×40mL), dried over anhydrous magnesiu...

Embodiment 2

[0049] This example illustrates the preparation of 2-chloroN-(3-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)acetamide

[0050] Add 0.01mol 5-amino-1-(4-fluorophenyl)-3-cyano-1H-pyrazole and 40ml dichloromethane into a 100ml four-neck flask, stir to dissolve, add 0.015mol chlorine dropwise under ice bath Acetyl chloride. Reaction at room temperature for 2h. After the reaction, filter and recrystallize the filter cake with ethanol to obtain 2.31 g of the product. Yield 83%. Product melting point: 105-107°C.

Embodiment 3

[0052] This example illustrates the synthesis of N-(3-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)-2-(5-fluorouracil-1-yl)acetamide (Compound 1)

[0053] Add 0.006mol of 5-fluorouracil and 150ml of DMF into a 250ml four-neck flask equipped with mechanical stirring, reflux condenser and thermometer, raise the temperature to 100°C and stir for 1h. 50ml of 0.002mol 2-chloro N-(3-cyano-1-(4-fluorophenyl)-1H-pyrazol-5-yl)acetamide DMF solution was added dropwise, and the reaction was continued for 5h after the dropwise addition. After the reaction, the solvent was concentrated to precipitate a solid, which was filtered and dried to obtain a crude product. Column chromatography using ethyl acetate as the eluent gave 0.41 g of the final product. Yield 55.4%. Melting point: 231-232°C; 1 HNMR (300MHz, DMSO-d 6 ) δ 11.57 (s, 1H, -CO-NH-CO-), 10.23 (s, 1H, -CO-NH), 7.99 (d, J=6.7Hz, 1H, -CF=CH), 7.89 (t , J=3.5Hz, 2H, Ar-H), 7.33(t, J=5.1Hz, 2H, Ar-H), 7.15(s, 1H, =CH), 4.47(s, 2H, CH ...

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Abstract

The invention discloses a halobenzene cyano pyrazol compound with the insecticidal action as well as a preparation method and application. The halobenzene cyano pyrazol compound is a compound shown in a structural general formula (1) or a pharmaceutically acceptable salt thereof. The compound has the advantages of little dosage, good insecticidal effect, simpleness in process method, low cost and wide market prospect.

Description

technical field [0001] The invention belongs to the field of pesticides, and in particular relates to a fluorouracil-containing halobenzocyanopyrazole compound, a preparation method thereof and an application as an insecticide. Background technique [0002] my country is a big agricultural country, and it is also one of the big countries that produce and consume pesticides. Before the 1990s, my country mainly imitated foreign pesticides, and there were few new pesticides developed independently. With my country's accession to intellectual property protection and the World Trade Organization, research and development of new pesticides with independent intellectual property rights has become a priority. It is imperative. [0003] Since pyrazole was first synthesized in 1968, pyrazole and pyrazole-based compounds have been widely used in pesticides, medicine and other fields due to their potential biological activities. Pyrazole pesticides are widely used, including herbicides...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A01N43/56A01P7/04
Inventor 万嵘傅晓东杨阳穆海萍蒋强华陈月秦小飞沈陈
Owner NANJING UNIV OF TECH
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