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Green Synthesis Process of Tribesulfuron-methyl for Broadleaf Weed Removal in Wheat Fields

A broadleaf agent ether, synthetic process technology, applied in the direction of organic chemistry, etc., can solve problems such as large environmental pressure, poisoning, employee injury, etc., and achieve the effect of low toxicity

Active Publication Date: 2015-09-09
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

prone to poisoning
The highly toxic and highly corrosive by-products of phosgene put phosgene as a production raw material under enormous environmental pressure and can also cause harm to employees

Method used

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  • Green Synthesis Process of Tribesulfuron-methyl for Broadleaf Weed Removal in Wheat Fields
  • Green Synthesis Process of Tribesulfuron-methyl for Broadleaf Weed Removal in Wheat Fields
  • Green Synthesis Process of Tribesulfuron-methyl for Broadleaf Weed Removal in Wheat Fields

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Take a 250mL clean round bottom flask, add 100mL N,N-dimethylformamide, add 9.2g 2-acetoxybenzenesulfonic acid, 4.83g 2-chloroethanol, 5.95g thionyl chloride, 5.05g Triethylamine was stirred and reacted for a period of time. Add 3.65g n-butylamine, 2.05g acetonitrile, 2g sodium hydroxide. After stirring and reacting for a period of time, after concentration, the product was obtained by column chromatography

[0019] (2) Take a 250mL round bottom flask, add 10.23g 2-(1-chloroethoxy)-benzenesulfonic acid, and add 100mL chlorobenzene solution. Add 9.9g of phosgene, and control the temperature of the oil bath at 85-105°C. Add 0.73g of N,N-dimethylformamide, and react for 5 hours and then the temperature drops to 60-70°C. 11.3 g of 30% ammonia solution was added within 1 hour and stirring was continued for 2 h. After cooling, the precipitate was filtered off.

[0020] (3) Take a 250mL round bottom flask, add 14g 2-amine-4-methoxy-6-methyl-1,3,5-triazine, 5.4g sodium...

Embodiment 2

[0021] Example 2 (1) Take a 5000mL clean round bottom flask, add 200mL N,N-dimethylformamide, add 18.4g 2-acetoxybenzenesulfonic acid, 9.66g 2-chloroethanol, 11.9g thionyl chloride , 10.1g triethylamine was stirred and reacted for a period of time. Add 7.3g n-butylamine, 4.1g acetonitrile, 4g sodium hydroxide. After stirring and reacting for a period of time, after concentration, the product was obtained by column chromatography

[0022] (2) Take a 500mL round bottom flask, add 20.46g 2-(1-chloroethoxy)-benzenesulfonic acid, and add 200mL chlorobenzene solution. Add 19.8g of phosgene, and control the temperature of the oil bath at 85-105°C. Add 1.46g of N,N-dimethylformamide, and react for 5 hours and the temperature drops to 60-70°C. 22.6 g of 30% ammonia solution were added within 1 hour and stirring was continued for 2 h. After cooling, the precipitate was filtered off.

[0023] (3) Take a 500mL round bottom flask, add 28g 2-amine-4-methoxy-6-methyl-1,3,5-triazine, 10....

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Abstract

The invention relates to a green synthesis process of a triasulfuron herbicide for removing broadleaf weed in a wheat field. The method comprises the following steps of: synthesizing 2-(1-chloroethoxy)-benzenesulfonic acid from 2-acetoxybenzenesulfonic acid and 2-chloroethanol as raw materials; then reacting the resulting 2-(1-chloroethoxy)-benzenesulfonic acid with phosgene and ammonia gas to generate 2-(1-chloroethoxy)-benzenesulfonamide, and finally reacting the resulting 2-(1-chloroethoxy)-benzenesulfonamide with dimethyl carbonate, 2-amino-4-methoxy-6-methyl-1,3,5-triazine to generate the final product of triasulfuron. The method is a relatively-effective solution to synthesis of triasulfuron. The process has the advantages of relatively-small toxicity and environmental friendliness as dimethyl carbonate as a substitute for phosgene is used in the last procedure.

Description

technical field [0001] The invention relates to a synthesis process of a sulfonylurea herbicide trisulfuron-methyl, which belongs to a synthesis process of an agent for removing broad-leaved weeds in wheat fields. Background technique [0002] Tribesulfuron-methyl is a highly effective sulfonylurea herbicide, which mainly has good control effect on broad-leaved grasses in wheat fields. Tribesulfuron-methyl herbicide is an inhibitor of acetolactate synthase (ALS), which disrupts protein synthesis, interferes with DNA synthesis, and cell division and growth by preventing the biosynthesis of branched-chain amino acids such as leucine and valine , eventually leading to the death of weeds, and has high safety to animals. It has the advantages of less dosage, good herbicidal effect and low cost of use. It has pre-emergence and post-emergence herbicidal activity on broad-leaved grasses, with a concentration of 16-24g a.i. / hm 2 The dose has good control effect on the main weeds of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D251/16
CPCC07D251/16
Inventor 于国权陈宇丁华平袁宇
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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