Methods for preparing crystalline L-glufosinate ammonium monohydrate are disclosed. The methods include forming a mixture comprising water, a water-miscible organic solvent, ammonium hydroxide, and a glufosinate starting material containing L-glufosinate ammonium and D-glufosinate ammonium. L-Glufosinate ammonium monohydrate is crystallized and separated from the mixture, providing L-glufosinate ammonium monohydrate Form B. Compositions and methods employing the crystalline L-glufosinate ammonium monohydrate are also described.
Compositions and methods for the production of L-glufosinate are provided. The method involves converting racemic glufosinate to the L-glufosinate enantiomer or converting PPO to L-glufosinate in an efficient manner. In particular, the method involves the specific amination of PPO to L-glufosinate, using L-glutamate, racemic glutamate, or another amine source as an amine donor. PPO can be obtained by the oxidative deamination of D-glufosinate to PRO (2- oxo-4-(hydroxy(methyl)phosphinoyl)butyric acid) or generated via chemical synthesis. PPO is then converted to L-glufosinate using a transaminase in the presence of an amine donor. When the amine donor donates an amine to PPO, L-glufosinate and a reaction by product are formed. Because the PPO remaining represents a yield loss of L-glufosinate, it is desirable to minimize the amount of PPO remaining in the reaction mixture. Degradation, other chemical modification, extraction, sequestration, binding, or other methods to reduce the effective concentration of the by-product, i.e., the corresponding alpha ketoacid or ketone to the chosen amine donor will shift the reaction equilibrium toward L-glufosinate, thereby reducing the amount of PPO and increasing the yield of L-glufosinate. Therefore, the methods described herein involve the conversion or elimination of the alpha ketoacid or ketone by-product to another product to shift the equilibrium towards L-glufosinate.
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Compositions and methods for isolating L-glufosinate from a composition comprising L-glufosinate and glutamate are provided. The method comprises converting the glutamate to pyroglutamate followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The composition comprising L-glufosinate and glutamate is subjected to an elevated temperature for a sufficient time to allow for the conversion of glutamate to pyroglutamate, followed by the isolation of L-glufosinate from the pyroglutamate and other components of the composition to obtain substantially purified L-glufosinate. The glutamate alternatively may be converted to pyroglutamate by enzymatic conversion. The purified L-glufosinate is present in a final composition at a concentration of 90% or greater of the sum of L-glufosinate, glutamate, and pyroglutamate. In some embodiments, a portion of the glutamate in the starting composition may be separated from the L-glufosinate using a crystallization step. Solid forms of L-glufosinate materials, including crystalline L-glufosinate ammonium, are also described.
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
B01D 15/36 - Selective adsorption, e.g. chromatography characterised by the separation mechanism involving ionic interaction, e.g. ion-exchange, ion-pair, ion-suppression or ion-exclusion
G01N 23/207 - Diffractometry, e.g. using a probe in a central position and one or more displaceable detectors in circumferential positions
5.
AZIRIDINE SPINOSYN DERIVATIVES AND METHODS OF MAKING
Compositions including derivatives of spinosyns of the following formulae and methods for the production of derivatives of spinosyns are provided. The spinosyn derivatives described herein include those functionalized on the C-5,6 double bond to provide an aziridine ring system. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and nematodes and are useful in the agricultural and animal health markets.
A01N 43/44 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
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.
C12P 41/00 - Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
A01N 57/20 - Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
C12N 1/21 - BacteriaCulture media therefor modified by introduction of foreign genetic material
Compositions and methods for the production of derivatives of spinosyns are provided. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and/or nematodes and are useful in the agricultural and animal health markets.
C07D 313/00 - Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
C07H 17/08 - Hetero rings containing eight or more ring members, e.g. erythromycins
A01N 43/22 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atom with one hetero atom rings with more than six members
Compositions including derivatives of spinosyns and methods for the production of derivatives of spinosyns are provided. The spinosyn derivatives described herein include spinosyn derivatives functionalized on the C5-C6 double bond of the spinosyn. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and nematodes and are useful in the agricultural and animal health markets.
C07D 313/00 - Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
C07H 17/08 - Hetero rings containing eight or more ring members, e.g. erythromycins
A01N 43/22 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atom with one hetero atom rings with more than six members
Compositions including derivatives of spinosyns and methods for the production of derivatives of spinosyns are provided. The spinosyn derivatives described herein include those functionalized on the C-13,14 double bond to provide an additional ring system. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and/or nematodes and are useful in the agricultural and animal health markets.
C07H 17/08 - Hetero rings containing eight or more ring members, e.g. erythromycins
A01N 43/22 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atom with one hetero atom rings with more than six members
C07D 313/00 - Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
Compositions including derivatives of spinosyns and methods for the production of derivatives of spinosyns are provided. The spinosyn derivatives described herein include spinosyn derivatives functionalized on the C5-C6 double bond of spinosyn A to provide an additional ring system. The method produces spinosyn derivatives that exhibit activity towards insects, arachnids, and/or nematodes and are useful in the agricultural and animal health markets.
C07D 313/00 - Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
C07H 17/08 - Hetero rings containing eight or more ring members, e.g. erythromycins
A01N 43/22 - Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atom with one hetero atom rings with more than six members
