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Preparation method for sulfur-containing carbofuran derivative with less than 0.1% of harmful impurity carbofuran

A technology of harmful impurities and derivatives, which is applied in the field of preparation of sulfur-containing carbofuran derivatives, can solve the problems that hinder the popularization and application of carbofuran sulfur-containing derivatives, and achieve the effect of broad application prospects

Active Publication Date: 2012-11-21
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the sulfur-containing derivatives of carbofuran synthesized by the existing technology, such as carbofuran, carbosulfan, etc., have a product quality percentage of less than 92%, and the product contains a high proportion of prohibited original drug carbofuran. About 1%, which seriously hinders the popularization and application of carbofuran sulfur derivatives such as carbosulfan and carbosulfan

Method used

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  • Preparation method for sulfur-containing carbofuran derivative with less than 0.1% of harmful impurity carbofuran
  • Preparation method for sulfur-containing carbofuran derivative with less than 0.1% of harmful impurity carbofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Carbofuran, chemical name N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β - Preparation of ethyl alanine

[0014] Add 1L 1,2-dichloroethane, 159g (1mol, 166mL) N-isopropyl-β-alanine ethyl ester and 101g (1mol) triethylamine into a stirred reactor, cool to 0 ℃. Add 67.5g (0.5mol) of sulfur monochloride dropwise under stirring, and react at 0-10°C for 1 hour after dropping. After the reaction, wash with water, separate the 1,2-dichloroethane layer, and concentrate under reduced pressure until 0.8 L of 1,2-dichloroethane is removed. Then lower the temperature to 5°C again, add 67.5g (0.5mol) sulfuryl chloride dropwise under stirring, react at 0-30°C for 3 hours after the dripping, add 210g (0.95mol) carbofuran, 20g (0.2mol) ) N-methylpyrrolidone and 0.3L 1,2-dichloroethane, cooled to -10°C, and 202g (2mol) triethylamine was added dropwise under stirring, and stirred at -10°C for 5 hours after the dropping, after the reaction was com...

Embodiment 2

[0016] Carbofuran, chemical name N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β - Preparation of ethyl alanine

[0017] Add 1.5L 1,2-dichloroethane, 159g (1mol, 166mL) N-isopropyl-β-alanine ethyl ester and 101g (1mol) triethylamine into a stirred reactor, cool to 0°C. Add 67.5g (0.5mol) of sulfur monochloride dropwise under stirring, and react at 0-10°C for 1 hour after dropping. After the reaction, wash with water, separate the 1,2-dichloroethane layer, and concentrate under reduced pressure until 0.8 L of 1,2-dichloroethane is removed. Then lower the temperature to 5°C again, add 67.5g (0.5mol) of sulfuryl chloride dropwise under stirring, react at 0-30°C for 3 hours after the dropping, add 210g (0.95mol) of carbofuran, 51.6g (0.5mol) mol) N-methylpyrrolidone and 0.3L 1,2-dichloroethane, cool to 0°C, add 202g (2mol) triethylamine dropwise under stirring, and stir at 0~10°C for 3 hours after dropping, the reaction is complete After w...

Embodiment 3

[0019] Carbofuran, chemical name N-[2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-β - Preparation of ethyl alanine

[0020] Add 1.3L 1,2-dichloroethane, 159g (1mol, 166mL) N-isopropyl-β-alanine ethyl ester and 101g (1mol) triethylamine into a stirred reactor, cool to 0°C. Add 67.5g (0.5mol) of sulfur monochloride dropwise under stirring, and react at 0-10°C for 1 hour after dropping. After the reaction, wash with water, separate the 1,2-dichloroethane layer, and concentrate under reduced pressure until 0.8 L of 1,2-dichloroethane is removed. Then lower the temperature to 5°C again, add 67.5g (0.5mol) sulfuryl chloride dropwise under stirring, react at 0-30°C for 3 hours after the dropwise completion, add 210g (0.95mol) carbofuran, 47.4g (0.6 mol) dimethylformamide and 0.3L 1,2-dichloroethane, cooled to 0°C, 202g (2mol) triethylamine was added dropwise under stirring, and stirred at 30°C for 2 hours after the dropping, after the reaction wa...

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Abstract

The invention discloses a preparation method for sulfur-containing carbofuran derivative with less than 0.1% of harmful impurity carbofuran. The preparation method comprises the following steps of: using di-n-butylamine or N-isopropyl-beta-alanine ethyl ester derivative and sulfur monochloride as raw materials to prepare into disulphide in the presence of an acid-binding agent triethylamine and an organic solvent 1, 2-dichloroethane; and then reacting with a chlorinating agent sulfuryl chloride to obtain nitrogen sulfur chlorine; and finally reacting with carbofuran under the effect of a cosolvent N-methyl-2-pyrrolidone or dimethylformamide so as to obtain the sulfur-containing carbofuran derivative with not less than 96% of quality percentage composition and less than 0.1% of main harmful impurity carbofuran. By adopting the preparation method, the problem that the carbofuran cannot be completely reacted during being reacted can be solved, the defects due to low content and low yield of sulfur-containing carbofuran derivatives such as benfuracarb and carbosulfan caused by a solid-liquid two-phase reaction can be avoided, the technical problem due to relatively high content of main harmful impurity carbofuran can be solved, and the content of the sulfur-containing carbofuran derivatives such as benfuracarb and carbosulfan can reach a value not less than 96%, and the yield is 97 to 98%, and the main harmful carbofuran in the product is less than or equal to 0.1%, so that the preparation method has a wide popularization and application prospect.

Description

technical field [0001] The invention relates to a preparation method of a sulfur-containing carbofuran derivative whose main harmful impurity carbofuran is less than 0.1%. Background technique [0002] Carbofuran is a broad-spectrum insecticide and nematicide with contact and stomach toxicity. It binds irreversibly to cholinesterase and is therefore highly toxic. It can be absorbed by the roots of plants and transported to various organs of plants, most of which are leaf margins. The soil application has a long residual effect period, while the paddy water surface application has a short residual effect period. It is suitable for the control of various pests on rice, cotton, tobacco, soybean and other crops, and can also be specially used as a seed treatment agent. Although carbofuran has the advantages of good effect and unique use, due to its high toxicity, five ministries and commissions including the Ministry of Agriculture jointly issued the No. Applications for new...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79
Inventor 杜升华刘卫东兰世林庞怀林王艳丽阳梅刘源黄兰兰
Owner 湖南海利常德农药化工有限公司
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