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Preparation method of herbicide triclopyr butoxyethyl ester

A technology of clopyroxyethyl butoxyethyl ester and clopyroxyacetic acid, which is applied in the field of agricultural chemicals, can solve the problems of non-compliance with green pesticide process requirements, non-compliance with green preparation requirements, cumbersome operations, etc., and achieve cost Low, little pollution, and the effect of improving the reaction yield

Inactive Publication Date: 2017-11-07
武汉华邦化学新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] WO2010023679A2 reports the synthesis method of butoxyethyl clopyroxyacetate, specifically using sodium clopyridinate as a raw material, which is etherified with methyl chloroacetate to generate methyl clopyroxyacetate, which is then hydrolyzed to generate triclopyroxy Sodium pyroxyacetic acid is acidified to obtain its acids, and then the herbicide triclopyroxyacetic acid butoxyethyl is prepared under the catalysis of sulfuric acid and ethylene glycol monobutyl ether. The disadvantage of the reaction is that the operation is cumbersome, and more methanol is produced during hydrolysis. The esterification reaction uses toluene as a solvent, which does not meet the requirements of green preparation and is not environmentally friendly
CN102295597A has reported to obtain intermediate butoxyethyl chloroacetate by etherification of 2-butoxyethanol and chlorohydrin, and then condense with sodium clopyridinate to obtain butoxyethyl clopyroxyacetate. Simple and high yield, but the use of toxic solvents such as solid acid and toluene in the reaction, the cost is high, and it does not meet the requirements of green pesticide technology

Method used

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  • Preparation method of herbicide triclopyr butoxyethyl ester
  • Preparation method of herbicide triclopyr butoxyethyl ester
  • Preparation method of herbicide triclopyr butoxyethyl ester

Examples

Experimental program
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Embodiment 1

[0029] Add 22g (0.1mol) sodium triclopyridinate and 100mL of N,N-dimethylformamide into a three-necked reaction flask equipped with a motor, condenser and dropping funnel, and add 0.2g of phase transfer catalyst PEG-400 under stirring , then dropwise add 20mL N,N-dimethylformamide liquid containing 9.4g (0.1mol) chloroacetic acid, after the addition, heat up to 140°C, react for 4.0h, cool, add 400mL ice water, acidify with dilute hydrochloric acid to pH=2 -3, extracted 4 times with 100mL ethyl acetate, combined the organic layers, washed twice with 100mL saturated brine, dried the organic layer, and desolventized to obtain the product. After recrystallization from ethanol, triclopyr was a white powder with a content of 98.2%. The rate is 95.3%.

[0030] Add 25.4g (0.1mol) of clopyroxyacetic acid, 80mL of dichloromethane, 0.3mol of oxalyl chloride into a dry one-necked bottle, and add a catalytic amount of N,N-dimethylformamide dropwise. React overnight at room temperature, re...

Embodiment 2

[0033] Add 22g (0.1mol) sodium triclopyridinate and 100mL of N,N-dimethylacetamide into a three-necked reaction flask equipped with a motor, condenser and dropping funnel, and add 0.2g of phase transfer catalyst PEG-400 under stirring , then add dropwise 20mL of N,N-dimethylacetamide liquid containing 9.4g (0.1mol) of chloroacetic acid, heat up to 140°C after addition, react for 5.0h, cool down, add 400mL of ice water, acidify with dilute hydrochloric acid to pH=2 -3, extracted 4 times with 110mL ethyl acetate, combined the organic layers, washed twice with 100mL saturated brine, dried the organic layer, and desolventized to obtain the product, after ethanol recrystallization, white powder triclopyr, with a content of 96.3%, was obtained. The rate is 92.3%.

[0034] Add 25.4g (0.1mol) of clopyroxyacetic acid, 80mL of dichloromethane, 0.3mol of oxalyl chloride into a dry one-necked bottle, and add a catalytic amount of N,N-dimethylformamide dropwise. React overnight at room te...

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Abstract

The invention discloses a preparation method of an herbicide, namely triclopyr butoxyethyl ester, belonging to the field of pesticide chemistry. The preparation method is implemented by the steps of reacting by virtue of raw materials including sodium trichloropyridinol and chloroacetic acid in the presence of a catalyst 1 and an organic solvent, so as to obtain picolinic acid type triclopyr (triklopir) as a raw material, preparing acyl chloride from triclopyr, carrying out condensation reaction by virtue of acyl chloride and 2-butoxyethanol in the presence of a catalyst 2, an acid-binding agent and an organic solvent, so as to obtain triclopyr butoxyethyl ester. The content of triclopyr butoxyethyl ester is 95.2%, and the yield is 85.6%; the synthesis is easy in operation, the post-treatment is simple and convenient, wastewater is little, and the preparation method is suitable for preparing the herbicide, namely triclopyr butoxyethyl ester.

Description

technical field [0001] The present invention relates to a kind of preparation method of pyridine carboxylic acid herbicide triclopyroxy ethyl ester, in particular to a kind of pyridine carboxylic acid herbicide triclopyr acetic acid and 2-butoxyethanol as the preparation method The raw material is a two-step condensation reaction method for preparing triclopyroxyethyl butoxyethyl ester under a catalyst and a dehydrating agent, which belongs to the field of agricultural chemicals. Background technique [0002] Triclopyr butoxyethyl is a pyridine carboxylic acid systemic herbicide, which can be used to control shrubs and broad-leaved weeds in forest farms, fire breaks in open forest areas, and soybean crops. Preparations are EC. The mechanism of this variety is that it can be absorbed by the leaves and roots of the plant, conduct the whole plant, by acting on nucleic acid metabolism, and make the plant produce excessive nucleic acid, transform some tissues into meristem, and ...

Claims

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Application Information

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IPC IPC(8): C07D213/64
Inventor 杨子辉田昊许丹
Owner 武汉华邦化学新材料有限公司
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