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Synthetic method of herbicide safener isoxadifen-ethyl

A technology of bisoxazole acid and synthesis method, which is applied in directions such as organic chemistry and achieves the effects of mild conditions, easy handling and little pollution

Inactive Publication Date: 2014-04-09
JIANGSU FLAG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to improve the existing isoxadifen preparation process, solve the generation of about 20% by-products in the cycloaddition reaction, greatly improve the yield of the product, and be beneficial to large-scale industrial production

Method used

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  • Synthetic method of herbicide safener isoxadifen-ethyl

Examples

Experimental program
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Effect test

Embodiment 1

[0018] When the temperature is 20-25°C, add 30 grams (0.166 moles) of 1,1-diphenylethylene, 43.5 grams (0.287 moles) of ethyl chlorooximinoacetate, and 120 grams of isopropanol into a 250-ml reaction flask. gram, 58 grams (0.69 moles) of sodium bicarbonate, stirred for about 1-4 hours, slowly heated the material to 60-70°C, stirred for 3-6 hours, cooled to below 10°C, acidified with dilute hydrochloric acid, precipitated the product, filtered , washed the filter cake with water, and dried to obtain 46.7g of the product, with a content of 97.3% and a yield of 95% (based on 1,1-diphenylethylene).

Embodiment 2

[0020] When the temperature is 20-25°C, add 30 grams (0.166 moles) of 1,1-diphenylethylene, 43.5 grams (0.287 moles) of ethyl chlorooximinoacetate, and 120 grams of isopropanol into a 250-ml reaction flask. grams, 69 grams (0.69 moles) of potassium bicarbonate, stirred for about 1-4 hours, slowly heated the material to 60-70°C, stirred for 3-6 hours, cooled to below 10°C, acidified with dilute hydrochloric acid, precipitated product, filtered , washed the filter cake with water, and dried to obtain 41.8g of the product, with a content of 95.5% and a yield of 85% (based on 1,1-diphenylethylene).

Embodiment 3

[0022] When the temperature is 20-25°C, add 30 grams (0.166 moles) of 1,1-diphenylethylene, 43.5 grams (0.287 moles) of ethyl chlorooximinoacetate, and 120 grams of isopropanol into a 2000-milliliter reaction flask gram, 95.3 grams (0.69 moles) of potassium carbonate, stirred for about 1-4 hours, the material was slowly heated to 60-70 ° C, stirred for 3-6 hours, cooled to below 10 ° C, acidified with dilute hydrochloric acid, precipitated product, filtered, The filter cake was washed with water and dried to obtain 44g of the product with a content of 93.8% and a yield of 89.6% (based on 1,1-diphenylethylene).

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Abstract

The invention discloses a synthetic method of herbicide safener isoxadifen-ethyl, the isoxadifen-ethyl is prepared by reaction of 1, 1-diphenyl ethylene and ethyl 2-chloro-2-(hydroxyimino)acetate under the effects of an alkali metal compound. The synthetic method is mild in reaction, simple in operation, high in yield, low in pollution, and easy to industrial production.

Description

technical field [0001] The invention belongs to the field of synthesis, and in particular relates to a method for synthesizing an effective herbicide safener isoxadifen. Background technique [0002] Isoxadifen, alias isoxadifen-ethyl, chemical name 4,5-dihydro-5,5-diphenyl-1,2-azole-3-carboxylic acid ethyl ester, English name Isoxadifen- Ethyl, English alias Ethyl4,5-dihydro-5,5-diphenylisoxazol-3-carboxylate, CAS NO.163520-33-0, molecular formula C18H17NO3, molecular weight 295.33. [0003] The mechanism of action of herbicide safener: herbicide safener (Safener), also known as antidote and protectant, is used to protect crops from herbicide damage, thereby increasing crop safety and improving weed control effect compound of. Herbicide safener has the ability to enhance the selectivity of herbicides between crops and weeds. It can not only improve the resistance of crops, protect crops from pesticide residues, but also be used to solve difficult weeds. The problem of we...

Claims

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Application Information

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IPC IPC(8): C07D261/04
CPCC07D261/04
Inventor 王豪张胜王凤云吴耀军
Owner JIANGSU FLAG CHEM IND
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