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Preparation method of glufosinate-ammonium and derivatives thereof

A derivative, glufosinate-ammonium technology, applied in the field of preparation of glufosinate-ammonium and its derivatives, can solve the problems of high environmental protection pressure, short reaction process, high boiling point, etc., to avoid the use of sodium cyanide, mild reaction conditions, The effect of high product yield

Inactive Publication Date: 2013-09-11
SHANDONG ACADEMY OF PESTICIDE SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The reaction process of this route is short and the yield is relatively high, but there are some disadvantages as follows: 1. The highly toxic sodium cyanide is used in the reaction process, which has potential safety hazards in the production process and great environmental protection pressure; 2. During the hydrolysis process with acid, A large amount of ammonium chloride is produced, and the purified product needs to be recrystallized many times, and the process is cumbersome; 3. The key intermediate cyanamide compounds in the reaction process have a high boiling point and no obvious ultraviolet absorption, so it is difficult to track and detect with gas chromatography and liquid chromatography The reaction process is not conducive to the intermediate control of the production process

Method used

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  • Preparation method of glufosinate-ammonium and derivatives thereof
  • Preparation method of glufosinate-ammonium and derivatives thereof
  • Preparation method of glufosinate-ammonium and derivatives thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Example 1: Preparation of 5-(2-(methylethoxyphosphono)ethyl)hydantoin

[0028] Add 12.01g (0.12mol) of hydantoin, 10.2g (0.15mol) of sodium ethoxide, and 90mL of ethanol into a 250mL three-necked flask, and stir at room temperature for 20min. After completely dissolving, add methyl-2-bromoethylphosphonic acid dropwise Ethyl ester 21.4g (0.10mol), after the dropwise addition was completed, the temperature was raised to 80°C to react for 5h, cooled to room temperature, the solid was removed by suction filtration, the solvent was removed by rotary evaporation, 100mL ethanol was added to dissolve and filter, and 5-(2-( Methylethoxyphosphono)ethyl)hydantoin crude product 20.88g, yield: 89.2%, content: 86.4%. 1 H NMR (D 2 O,300MHz)δ:1.212~1.245(m,3H);1.513(d,J=13.6Hz,3H);1.672~1.910(m,4H);3.928~3.976(m,2H);4.182(t,J =5.4Hz, 1H).

Embodiment 2

[0029] Example 2: Preparation of 5-(2-(methylethoxyphosphono)ethyl)hydantoin

[0030] Add 12.01g (0.12mol) of hydantoin, 10.2g (0.15mol) of sodium ethoxide, and 90mL of ethanol into a 250mL three-necked flask, and stir at room temperature for 20min. After completely dissolving, add methyl-2-bromoethylphosphonic acid dropwise 21.4g (0.10mol) of ethyl ester, after the dropwise addition was completed, the temperature was raised to 40°C to react for 5h, cooled to room temperature, the solid was removed by suction filtration, the solvent was removed by rotary evaporation, and 100mL ethanol was added to dissolve and filter, and 5-(2-( Methylethoxyphosphono)ethyl)hydantoin crude product 13.68g, yield: 58.4%, content: 56.6%.

Embodiment 3

[0031] Example 3: Preparation of 5-(2-(methylethoxyphosphono)ethyl)hydantoin

[0032] Add 12.01g (0.12mol) of hydantoin, 10.2g (0.15mol) of sodium ethoxide, and 90mL of ethanol into a 250mL three-necked flask, and stir at room temperature for 20min. After completely dissolving, add methyl-2-bromoethylphosphonic acid dropwise Ethyl ester 21.4g (0.10mol), after the dropwise addition was completed, the temperature was raised to 80°C for 3h, cooled to room temperature, the solid was removed by suction filtration, the solvent was removed by rotary evaporation, and 100mL ethanol was added to dissolve and filter, and 5-(2-( Methylethoxyphosphono)ethyl)hydantoin crude product 18.36g, yield: 78.4%, content: 76.6%.

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Abstract

The invention discloses a preparation method of glufosinate-ammonium and derivatives thereof. The method comprises the following steps: (1) by using a substituted hydantoin and methylphosphonate compounds as a raw material, adding alkali, carrying out nucleophilic substitution reaction at the reaction temperature of 20-100 DEG C in a reaction solvent to obtain a hydantoin derivative, and tracing product generation condition by high performance liquid chromatography in the reaction process to judge the reaction endpoint, wherein the molar ratio of the methylphosphonate compounds, substituted hydantoin and alkali is 1:(1.0-5.0):(1.0-4.0); (2) carrying out reflux reaction for prepared hydantoin derivative prepared and an inorganic acid in water for 30-60 hours; after reaction, adding ammonia water to adjust the pH of the liquor to 12; spirally distilling to remove the solvent; adding absolute methanol for reflux for 30-60 minutes; filtering; spirally drying the mother liquor; adding methanol for recrystallization to obtain pure glufosinate-ammonium shown in formula (I) or derivatives thereof, wherein the molar ratio of the hydantoin derivative and inorganic acid is 1.0:(4.0-9.0).

Description

technical field [0001] The invention relates to a preparation method of glufosinate-ammonium and derivatives thereof. Background technique [0002] Glufosinate is a new type of herbicide developed by Hearst in the 1980s. It can be used in orchards, vineyards, and non-cultivated land to control annual and perennial dicotyledonous and gramineous weeds. With glufosinate-ammonium as the target, Hearst has successfully introduced glufosinate-ammonium resistance genes into more than 20 crops such as rice, wheat, and corn through resistance gene transfer and breeding of resistant crop varieties. These genetically modified crops are not only widely planted in North America, but also began to be promoted in some countries and regions such as Asia, Australia, and Europe in recent years. At present, the amount of glufosinate-ammonium is second only to glyphosate, and it is the second largest genetically modified crop resistant to herbicides in the world. . With the rapid development ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30A01N57/20A01P13/00
Inventor 李旭坤韩金涛柴宏伟张作山左伯军翟春伟刘凤玲唐永军刘伟华
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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