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Preparation method of fine glufosinate

An essence glufosinate-ammonium and reaction technology, applied in the field of organic compound synthesis, can solve the problems of high cost, complicated operation, low yield and the like, and achieve the effects of reducing production cost, simple process and improving total yield

Inactive Publication Date: 2018-09-11
SHANDONG ACADEMY OF PESTICIDE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] For this reason, the technical problem to be solved by the present invention is to provide a kind of preparation method of refined glufosinate-ammonium, to solve the problems of complex operation, high cost and low yield in the synthesis process of refined glufosinate-ammonium in the prior art

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  • Preparation method of fine glufosinate

Examples

Experimental program
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Effect test

Embodiment 1

[0063] The synthetic method of essence glufosinate-ammonium described in the present embodiment comprises the steps:

[0064] (1) Synthesis of Compound III: Add 110g (0.92mol) of L-homoserine, 300ml toluene, and 2g (0.012mol) of p-toluenesulfonic acid to a 2L three-necked flask, connect the azeotropic dehydration device, stir evenly, and slowly heat to 108°C, carry out azeotropic dehydration reaction for 12h, then cool to 80°C, slowly add 142.8g (1.2mol) of thionyl chloride dropwise, stir and react for 4h, cool to room temperature after the reaction, filter, and take the filter cake with toluene (50mL ×3 times), water (50mL×5 times), and dried to obtain 98.5g of white solid powder, which is the desired compound of formula (Ⅲ), that is, L-3,6-bis(2-chloroethyl) -2,5-diketopiperazine, the calculated yield is 88.7%;

[0065] (2) Synthesis of Compound IV: Under nitrogen protection, add 98.5 g (0.408 mol) of the obtained L-3,6-bis(2-chloroethyl)-2,5-diketopiperazine into a 2L thre...

Embodiment 2

[0070] The synthetic method of essence glufosinate-ammonium described in the present embodiment comprises the steps:

[0071] (1) Synthesis of compound III: Add 59.5g (0.5mol) of L-homoserine, 200ml of benzene, and 1.58g (0.01mol) of benzenesulfonic acid into a 1000mL three-neck flask, connect the azeotropic dehydration device, stir evenly, and heat slowly To 80°C, azeotropic dehydration reaction for 30h; then cool to 60°C, add 1.6g (0.02mol) of pyridine, slowly drop in 98.9g (0.5mol) of diphosgene, stir for 10h, cool to room temperature, filter, filter cake Wash with benzene (30mL×3 times), water (30mL×5 times), and dry the filter cake to obtain 52.7g of white solid powder compound III, namely L-3,6-bis(2-chloroethyl)-2, 5-diketopiperazine, calculate its productive rate 86.5%;

[0072] (2) Synthesis of compound IV: with step (2) in Example 1;

[0073] (3) Synthesis of essence glufosinate-ammonium: same as step (3) in Example 1.

Embodiment 3

[0075] The synthetic method of essence glufosinate-ammonium described in the present embodiment comprises the steps:

[0076] (1) Synthesis of Compound III: Add 71.4g (0.6mol) of L-homoserine, 200ml of xylene, and 1.6g (0.01mol) of p-benzenesulfonic acid into a 1000mL three-neck flask, connect the azeotropic dehydration device, and stir evenly. Slowly heat to 140°C, azeotropic dehydration reaction for 8h; then cool to 80°C, slowly drop in 107g (0.9mol) of thionyl chloride, stir for 4h, cool to room temperature; filter, filter cake with toluene (30mL×3 times ), water (30mL×5 times), and the filter cake was dried to obtain 64.1g of white solid powder compound III, namely L-3,6-bis(2-chloroethyl)-2,5-diketopiperazine, Calculate the yield of 87.4%;

[0077] (2) Synthesis of compound IV: with step (2) in Example 1;

[0078] (3) Synthesis of essence glufosinate-ammonium: same as step (3) in Example 1.

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Abstract

The invention belongs to the technical field of organic compound synthesis and relates to a preparation method of fine glufosinate, in particular to a preparation method of fine glufosinate with L-homoserine as a raw material. According to the preparation method of fine glufosinate, L-homoserine prepared through a biological fermentation method serves as an initial raw material, L-3,6-di(2-halogenethyl)-2,5-diketopiperazine is prepared through the steps such as azeotropic dehydration and halogenation, a Serhiy Arbuzov reaction is conducted between L-3,6-di(2-halogen ethyl)-2,5-diketopiperazine and methyl phosphonic acid dibutyl, and fine glufosinate is prepared through a hydrolysis reaction. Compared with an existing preparation technology, the preparation method of fine glufosinate has the advantages that the total yield of fine glufosinate is greatly increased, the technological process is simple, and fine glufosinate is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a method for preparing refined glufosinate-ammonium, in particular to a method for preparing refined glufosinate-ammonium by using L-homoserine as a raw material. Background technique [0002] Glufosinate-ammonium is a broad-spectrum organophosphate contact herbicide successfully developed by Hearst in the 1980s. Glufosinate-ammonium is a glutamine synthesis inhibitor, and its systemic effect is not strong. Glyphosate kills roots differently. Glufosinate-ammonium kills leaves first, and then conducts transpiration in plant xylem through plant transpiration. Its quick-acting performance is between paraquat and glyphosate, and it is a non-selective contact herbicide. Glufosinate-ammonium includes L-glufosinate-ammonium and racemic DL-type glufosinate-ammonium, wherein the herbicidal activity of L-glufosinate-ammonium is twice that of racemic DL-type g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
CPCC07F9/301
Inventor 董文凯柴洪伟解银萍韩金涛丛云波王秀丽张作山李旭坤
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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