Preparation method of glufosinate-ammonium

A technology of glufosinate-ammonium and methylphosphonic acid, which is applied in the field of synthesis of glufosinate-ammonium, can solve the problems of cumbersome purification process, high environmental requirements, and difficult monitoring, and achieve the effect of high purity, high yield, and easy monitoring

Inactive Publication Date: 2014-08-06
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The relatively mature technology of chemical synthesis method is the strecker method (US6359162, CN1267305A) at present, and this route uses diethyl methyl phosphite as raw material, and after reacting with acrolein, acetal product is obtained, and then reacted with cyanide, ammonium chloride, etc. Obtain α-amino nitrile compounds, then hydrolyze to obtain glufosinate-ammonium, the yield is stable at about 30% (in terms of diethyl methyl phosphite), and the cond

Method used

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  • Preparation method of glufosinate-ammonium
  • Preparation method of glufosinate-ammonium

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] step 1

[0021]

[0022] In a 250mL three-necked flask, add 10.6g (0.05mol) methyl (2-bromoethyl) ethyl phosphonate, 8.85g (0.05mol) phenylmethylene glycine methyl ester, 8.34g (0.06mol) of potassium carbonate and 100mL tetrahydrofuran, heated to reflux, liquid phase monitoring reaction until the reaction of phenylmethylene glycine methyl ester was completed, cooled, filtered, added 50mL dichloromethane after the filtrate was precipitated, washed with water until neutral, and the organic layer was spin-dried to obtain 2 - 14.3 g of phenylmethyleneamino-4-ethoxy(methyl)phosphonobutanoic acid methyl ester, yield 87.6%.

[0023] 1 H NMR (500MHz, CDCl 3 ):8.31(s,1H,CH),7.42-7.79(m,5H,5×Ar-H),4.36(t,1H,CH),4.22(q,2H,OCH 2 ),3.84(s,3H,OCH 3 ),1.94-2.02(m,2H,CH 2 ),1.54-1.69(m,2H,CH 2 ), 1.38(t,3H,CH 3 ),1.28(d,3H,J=3.8Hz,CH 3 ).

[0024] step 2

[0025]

[0026] Add 20 g (0.0615 mol) of 2-phenylmethyleneamino-4-ethoxy (methyl) phosphonobutanoic acid methyl est...

Embodiment 2

[0032] step 1

[0033]

[0034] In a 250mL three-necked flask, add 10.6g (0.05mol) ethyl methyl (2-bromoethyl) phosphonate, 13.35g (0.05mol) ethyl dibenzylidene glycine, 3.36g (0.06mol) potassium hydroxide ) and 100mL tetrahydrofuran, heat up to reflux, monitor the reaction in the liquid phase until the reaction of dibenzylidene glycine ethyl ester is completed, cool, filter, add 50mL chloroform after the filtrate is precipitated, wash with water until neutral, and spin dry the organic layer 16.7 g of ethyl 2-diphenylmethyleneamino-4-ethoxy(methyl)phosphonobutyrate was obtained, with a yield of 83.7%.

[0035] 1 H NMR (500MHz, CDCl 3 ):7.67(dd,2H,2×Ar-H),7.28-7.49(m,6H,6×Ar-H),7.16-7.20(m,2H,2×Ar-H),4.43(q,2H ,OCH 2 ),4.28(t,1H,CH),4.22(q,2H,OCH 2 ),1.98-2.08(m,2H,CH 2 ),1.59-1.72(m,2H,CH 2 ), 1.44(t,3H,CH 3 ), 1.41(t,3H,CH 3 ),1.30(d,3H,J=4.2Hz,CH 3 ).

[0036] step 2

[0037]

[0038] Add 15g (0.0374mol) ethyl 2-diphenylmethyleneamino-4-ethoxy (methyl) phosph...

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Abstract

The invention discloses a preparation method of glufosinate-ammonium. The method comprises the steps that methylphosphonate compound (II) and benzylidene glycine ester compound (III) are reacted, so as to obtain benzylidene phosphonic butyric ester compound (IV); the benzylidene phosphonic butyric ester compound (IV) is further hydrolyzed, so as to obtain hydrochloride (V); finally, the target product glufosinate-ammonium (I) is obtained. The method has the advantages that the utilization of extremely toxic substance cyanide is avoided, the reaction condition is mild, monitoring is easy, and repeated recrystallization is not required for removing inorganic salt. (img file='DDA0000501075940000011.TIF' wi='1408' he=' 672' /).

Description

technical field [0001] The invention relates to a synthesis technique of herbicide, in particular to a synthesis method of glufosinate-ammonium. Background technique [0002] Glufosinate-ammonium is a high-efficiency, broad-spectrum, low-toxic non-selective herbicide developed by the German Hoechst company. The target enzyme is glutamine synthetase. Glufosinate-ammonium can inhibit all known forms of glutamine synthetase. It leads to the disorder of nitrogen metabolism in plants, the excessive accumulation of ammonia, and the disintegration of chloroplasts, which inhibits photosynthesis and eventually leads to plant death. The commercially available glufosinate-ammonium is a racemic mixture, and only the L- form has herbicidal activity. It is currently an ideal herbicide for transgenic resistant crops and has broad application prospects. Its synthesis methods mainly include chemical synthesis and fermentation. The fermentation method is mainly to produce bialaphos through ...

Claims

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Application Information

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IPC IPC(8): C07F9/30C07F9/32
Inventor 毛明珍何琦文张媛媛苏天铎魏乐王列平林双政宁斌科
Owner XIAN MODERN CHEM RES INST
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