IP Library › Patent Application 19324859
Patent Application
App. No. 19/324,859

METHODS FOR MAKING L-GLUFOSINATE

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Patent No.
US None
App. No.
19/324,859
Abstract

Methods for the production of L-glufosinate (also known as phosphinothricin or (S)-2-amino-4-(hydroxy(methyl)phosphonoyl)butanoic acid) are provided. The methods comprise a two-step process. The first step involves the oxidative deamination of D-glufosinate to PPO (2-oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid). The second step involves the specific amination of PPO to L-glufosinate, using an amine group from one or more amine donors. By combining these two reactions, the proportion of L-glufosinate in a mixture of L-glufosinate and D-glufosinate can be substantially increased.

Claims (72)

1 . A formulation comprising:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate ammonium, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation; and

one or more additional components selected from the group consisting of:

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and water.

2 . A formulation comprising:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation; and

one or more additional components selected from the group consisting of:

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and a diluent.

3 . The formulation of claim 2 , wherein the formulation has greater than about 95% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation.

4 . A formulation comprising:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation; and

one or more additional components selected from the group consisting of:

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 3-20% by weight of the formulation; and water.

5 . A formulation comprising:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate, wherein the formulation has greater than about 95% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation; and

one or more additional components selected from the group consisting of:

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and water.

6 . The formulation of claim 1 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 36.75% by weight of the formulation.

7 . The formulation of claim 1 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 24.5% by weight of the formulation.

8 . The formulation of claim 1 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 15.8% by weight of the formulation; 1-methoxy-2-propanol in an amount of 0.5% by weight of the formulation; dipropylene glycol in an amount of 4.3% by weight of the formulation; alkyl polysaccharide in an amount of 4.9% by weight of the formulation; and water in an amount of 62.25% by weight of the formulation.

9 . The formulation of claim 1 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 58.45% by weight of the formulation.

10 . The formulation of claim 1 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 46.2% by weight of the formulation.

11 . The formulation of claim 1 , wherein the formulation comprises:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate ammonium, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation;

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and

water.

12 . The formulation of claim 2 , wherein the formulation comprises:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate ammonium, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation;

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and

a diluent.

13 . The formulation of claim 4 , wherein the formulation comprises:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate ammonium, wherein the formulation has greater than about 90% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation;

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 3-20% by weight of the formulation; and

water.

14 . The formulation of claim 5 , wherein the formulation comprises:

L-glufosinate ammonium in an amount from 10-30% by weight of the formulation and D-glufosinate ammonium, wherein the formulation has greater than about 95% L-glufosinate compared to the sum of the D-glufosinate and the L-glufosinate present in the formulation;

sodium alkyl ether sulfate in an amount from 10-40% by weight of the formulation;

1-methoxy-2-propanol in an amount from 0.5-2% by weight of the formulation;

dipropylene glycol in an amount from 4-18% by weight of the formulation;

alkyl polysaccharide in an amount from 4-20% by weight of the formulation; and

water.

15 . The formulation of claim 4 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 36.75% by weight of the formulation.

16 . The formulation of claim 4 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 24.5% by weight of the formulation.

17 . The formulation of claim 4 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 15.8% by weight of the formulation; 1-methoxy-2-propanol in an amount of 0.5% by weight of the formulation; dipropylene glycol in an amount of 4.3% by weight of the formulation; alkyl polysaccharide in an amount of 4.9% by weight of the formulation; and water in an amount of 62.25% by weight of the formulation.

18 . The formulation of claim 4 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 58.45% by weight of the formulation.

19 . The formulation of claim 4 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 46.2% by weight of the formulation.

20 . The formulation of claim 5 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 36.75% by weight of the formulation.

21 . The formulation of claim 5 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 31.6% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; dipropylene glycol in an amount of 8.6% by weight of the formulation; alkyl polysaccharide in an amount of 9.8% by weight of the formulation; and water in an amount of 24.5% by weight of the formulation.

22 . The formulation of claim 5 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 15.8% by weight of the formulation; 1-methoxy-2-propanol in an amount of 0.5% by weight of the formulation; dipropylene glycol in an amount of 4.3% by weight of the formulation; alkyl polysaccharide in an amount of 4.9% by weight of the formulation; and water in an amount of 62.25% by weight of the formulation.

23 . The formulation of claim 5 , wherein the L-glufosinate ammonium is present in an amount of 12.25% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 58.45% by weight of the formulation.

24 . The formulation of claim 5 , wherein the L-glufosinate ammonium is present in an amount of 24.5% by weight of the formulation; and wherein the one or more additional components comprise sodium alkyl ether sulfate in an amount of 22.1% by weight of the formulation; 1-methoxy-2-propanol in an amount of 1% by weight of the formulation; alkyl polysaccharide in an amount of 6.2% by weight of the formulation; and water in an amount of 46.2% by weight of the formulation.