Method for preparing L-glufosinate-ammonium

A technology for glufosinate-ammonium and methylphosphonous dichloride is applied in the field of preparing L-glufosinate-ammonium, can solve the problems of low yield, difficult separation, poor substrate tolerance and the like, and achieves simple steps and easy-to-obtain raw materials. , cost controllable effect

Active Publication Date: 2020-09-15
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemical synthesis of L-glufosinate-ammonium mainly includes chiral auxiliary agent induction method, racemate resolution method and asymmetric synthesis method, etc., but these methods face complex synthetic routes, low yield or / and chiral resolution reagents Expensive problem, it is difficult to achieve its efficient industrial production, or it is difficult to achieve greater industrial application value
Biological synthesis of L-glufosinate-ammonium mainly includes protease method, amino acid dehydrogenase method and transaminase method, etc. These methods often have defects such as low product optical purity, difficult separation or / and poor substrate tolerance, and their industrial application value relatively low

Method used

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  • Method for preparing L-glufosinate-ammonium
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  • Method for preparing L-glufosinate-ammonium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Preparation of compound 2

[0032]

[0033] Add 140g of L-homoserine (1) (95% ee value) and 250g of ethylene glycol into a three-neck flask, heat up to 150°C and stir for reaction. After 36 hours of reaction, MS detects that the raw materials disappear, cool to 0°C to crystallize and pump Filter to obtain a yellow-brown filter cake, wash with isopropanol three times, and dry to obtain 110 g of brown-yellow solid compound (2), with a yield of 93%.

[0034] The structural identification data of compound 2 are as follows:

[0035] 1 H NMR (400MHz,D 2 O)δ4.26-4.17(m,2H),3.74-3.69(m,4H),2.10-2.02(m,4H); MSCalcd.m / z for C 8 h 14 N 2 o 4 [M+H] + 203.1, found 203.1.

[0036] (2) Preparation of Compound 3

[0037]

[0038] Under nitrogen atmosphere, 110g (0.54mol) of compound (2), 109g (1.08mol) of triethylamine and 200mL of trimethylbenzene were respectively added to the three-necked flask, the temperature was lowered to -20°C, and 28g of methylphosphine dich...

Embodiment 2

[0047] According to the method for Example 1, change the base type in step (2), change the catalyst type and reaction temperature in step (3), the results are shown in Table 1 below.

[0048] Wherein, the molar consumption of different base types in step (2) is 1.08mol, and the catalyst consumption in step (3) is 5g.

[0049] The yield of compound (4) is based on the two-step yield of compound (2), and the yield of L-glufosinate-ammonium is based on the single-step yield of compound (4).

[0050] Table 1

[0051]

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Abstract

The invention relates to a method for preparing L-glufosinate-ammonium. Compared with an existing method, the method of the invention is a new chemical synthesis route, is simple in steps, easily available in raw materials and controllable in cost, can obtain the L-glufosinate-ammonium product with the high ee value without chiral catalysis, and has potential industrial application value.

Description

technical field [0001] The invention relates to a method for preparing L-glufosinate-ammonium. 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 glufosinate-ammonium. Glufosinate-ammonium preparations currently on the market are generally racemic DL-type glufosinate-ammonium. If glufosinate-ammonium products can be used in the form of pure...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30C07F9/6509
CPCC07F9/301C07F9/650952
Inventor 刘永江周磊曾伟刘俊强左翔程柯
Owner LIER CHEM CO LTD
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