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Halobenzene cyanopyrazole compound containing purine structure as well as preparation method and application

A technology of halobenzocyanopyrazoles and compounds, which is applied in the field of halobenzocyanopyrazoles and their preparation, and achieves the effects of simple synthesis process, broad application prospects, and less dosage

Inactive Publication Date: 2016-05-25
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] After literature search, in the prior art, the halobenzocyanopyrazole compound containing the purine structure shown in the general formula (I) of the present invention has no report

Method used

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  • Halobenzene cyanopyrazole compound containing purine structure as well as preparation method and application
  • Halobenzene cyanopyrazole compound containing purine structure as well as preparation method and application
  • Halobenzene cyanopyrazole compound containing purine structure as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This example illustrates the preparation of the sodium salt of 6-mercaptopurine

[0032] Add 0.01mol of 6-mercaptopurine and 20mL of methanol into a 100mL round-bottomed four-neck flask to dissolve it completely, and add methanol solution containing 0.04g (0.01mol) of NaOH into a constant pressure dropping funnel, and slowly add it dropwise. After reacting for 5-6h, the reaction was completed, and a solid was precipitated, filtered, and dried to obtain 1.70 g of a white solid, with a yield of 98%.

Embodiment 2

[0034] This example illustrates the preparation of 5-amino-1-phenyl-3-cyano-1H-pyrazole

[0035] Add 0.01 mol of aniline and a small amount of ethanol to a 250 mL round-bottomed three-necked 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.

[0036] 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 40 mL of dichloromethane, the organic layer was washed with water (2×30 mL), washed with saturated sodium chloride solution (1×40 mL), dried over anhydrous magnesium sulfate, an...

Embodiment 3

[0038] This example illustrates the preparation of 2-chloro-N-(3-cyano-1H-pyrazol-5-yl)acetamide

[0039] In a 100mL four-neck flask, add 0.01mol 5-amino-1-phenyl-3-cyano-1H-pyrazole, 40mL dichloromethane, stir to dissolve, add 0.015 chloroacetyl chloride dropwise under ice bath, and react at room temperature 2h. After the reaction was completed, filter and recrystallize the filter cake with ethanol to obtain 1.54 g of the product. Yield 82.5%. Product melting point: 182-184°C.

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Abstract

The invention discloses a halobenzene cyanopyrazole compound containing a purine structure as well as a preparation method and an application. The halobenzene cyanopyrazole compound is a compound with a general structure (I) as shown in the specification or a pharmaceutically acceptable salt thereof. The compound is low in dosage, good in insecticidal efficacy, simple in technique, low in cost and wide in market prospect.

Description

technical field [0001] The invention belongs to the field of pesticides and insecticides, and in particular relates to halobenzocyanopyrazole compounds containing a purine structure, a preparation method and an application as an insecticide. Background technique [0002] In the field of pesticides, safe, efficient and green pesticides have always been the mainstream of the market, and are also the requirements for the development of new pesticides. The halobenzocyanopyrazoles represented by fipronil have the advantages of high efficiency, low toxicity, good selectivity and less residue, and have attracted widespread attention. Fipronil is a gamma-aminobutyric acid (GABA) receptor insecticide. By binding to the GABA receptor on the membrane of the target biological nerve center, the chloride ion channel is opened, the chloride ion is released rapidly, and an inhibitory post-emphasis potential is generated. (IPSP) thus affects the normal prominent transmission of the central ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/38A01N43/90A01P7/04
CPCA01N43/90C07D473/38
Inventor 万嵘吴少华郭春伟管西琳陈福立韩振禹付小换
Owner NANJING UNIV OF TECH
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