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Crystal forms of L-glufosinate-ammonium, and preparation method and application thereof

A technology of glufosinate-ammonium and glufosinate-ammonium hydrochloride is applied to the crystal form of L-glufosinate-ammonium and the fields of preparation and application thereof, which can solve the problems of less research on crystal form, insufficient stability, insufficient hygroscopicity, ionization difference and the like , to achieve the effects of good solubility, good pharmacokinetics, and improved levels

Pending Publication Date: 2021-10-08
SHANGHAI QIZHOU ZIYUE BIOTECHNOLOGY CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are relatively few studies on crystal forms. CN111065270 describes the separation from the glutamic acid composition and the crystalline forms A to E of L-glufosinate-ammonium obtained through screening, wherein the crystalline form A is metastable and tends to be converted into other forms , Ion chromatography shows that the ammonium ion content is 6.4%, indicating that the crystalline form is a mixed crystal of ammonium salt structure and zwitterionic structure, crystalline form B is the crystalline form of L-glufosinate zwitterion, and crystalline form C is metastable , readily converts to Form A and Form B; crystalline Form D is prepared from several room temperature or elevated temperature slurries in polymorph screens, typically in admixture with Form A, and both Form B and Form D Anhydrous crystalline form that is the free form of L-glufosinate-ammonium; 1H NMR spectrum of Form E is consistent with L-glufosinate-ammonium, but with peak shifts suggesting potential ionization differences, IC analysis shows only a small amount of ammonium and stoichiometry amount of chloride, the results suggest that Form E is not the form of L-glufosinate-ammonium, but the form of L-glufosinate hydrochloride
[0004] However, the crystalline form of the above-mentioned L-glufosinate-ammonium still shows one or more deficiencies in stability, hygroscopicity, etc., so it is very important to study the polymorphism of herbicides and find a crystal form with good properties. significance

Method used

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  • Crystal forms of L-glufosinate-ammonium, and preparation method and application thereof
  • Crystal forms of L-glufosinate-ammonium, and preparation method and application thereof
  • Crystal forms of L-glufosinate-ammonium, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1: Preparation of the crystal form A of L-glufosinate-ammonium

[0063] Method 1: L-glufosinate-ammonium hydrochloride (100g, 0.46mol) is added in water (200g), feeds ammonia gas and adjusts pH=7, underpressure distillation concentrates to 75%, adds methanol ( 600g), was cooled to 5°C at a cooling rate of Tj-Tr=2K, kept at a temperature of 24 hours, solids were precipitated, filtered, dried, then added to methanol (300g) and refluxed for 24 hours, and cooled at a cooling rate of Tj-Tr=2K The temperature was lowered to 5° C., and the temperature was kept for 24 hours. Solids were precipitated, filtered, and dried to obtain the crystal form A of L-glufosinate-ammonium with an HPLC purity of 99%.

[0064] Method 2: Add L-glufosinate-ammonium hydrochloride (100g, 0.46mol) into water (200g), feed ammonia gas to adjust pH=7, concentrate to 50% by distillation under reduced pressure, cool to 30°C, and Add methanol (600g) at a rate of 2g / min under high temperature, ...

Embodiment 2

[0070] Embodiment 2: Preparation of the crystal form B of L-glufosinate-ammonium

[0071] Add L-glufosinate-ammonium hydrochloride (100g, 0.46mol) into water (200g), feed ammonia gas to adjust pH=7, concentrate to 50% by distillation under reduced pressure, add methanol (600g) at 60°C, The temperature was lowered to 5° C. at a cooling rate of Tj-Tr=2K, and the temperature was kept for 5 days. Solids were precipitated, filtered, and dried to obtain the crystal form B of L-glufosinate-ammonium.

[0072] Carry out XRPD test to the solid of above-mentioned gain, spectrogram is as image 3 As shown, there are characteristic peaks at diffraction angles 2θ=9.484°, 12.163°, 17.098°, 22.540°, and 34.899°, and the 2θ error range is ±0.2 degrees. Its x-ray powder diffraction data are shown in Table 2.

[0073] Table 2: XRPD pattern details of Form B of L-glufosinate-ammonium

[0074]

[0075]

[0076] DSC results ( Figure 4 ) shows that there is an absorption peak at 134.07° C. ...

Embodiment 3

[0077] Embodiment 3: Preparation of the crystal form C of L-glufosinate-ammonium

[0078] Add L-glufosinate-ammonium hydrochloride (100 g, 0.46 mol) into water (200 g), pass through ammonia gas to adjust pH=2.5, concentrate to 50% by distillation under reduced pressure, add methanol (300 g) at 60 ° C, The temperature was lowered to 5° C. at a cooling rate of Tj-Tr=1K, and the temperature was kept for 24 hours. Solids were precipitated, filtered, and dried to obtain the crystal form C of L-glufosinate-ammonium.

[0079] Carry out XRPD test to the solid of above-mentioned gain, spectrogram is as Figure 5 As shown, there are characteristic peaks at diffraction angles 2θ=16.018°, 19.067°, 19.338°, and 21.581°, and the 2θ error range is ±0.2 degrees. Its x-ray powder diffraction data are shown in Table 3.

[0080] Table 3: XRPD pattern details of Form C of L-glufosinate-ammonium

[0081]

[0082]

[0083] DSC results ( Figure 6 ) shows that there is an absorption peak a...

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Abstract

The invention discloses crystal forms of L-glufosinate-ammonium, and a preparation method and application thereof. The crystal forms of the L-glufosinate-ammonium comprise ammonium salt forms A and B and zwitterionic forms C. The crystal forms show excellent effects in the aspects of stability, hygroscopicity, storability and the like, are beneficial to preparation, separation and storage of herbicides, and are good in solubility and pharmacokinetics, and the weed control level and speed of the weeding medicine are favorably improved.

Description

technical field [0001] The present invention specifically relates to the crystal form of L-glufosinate-ammonium and its preparation method and application. Background technique [0002] Glufosinate-ammonium, a contact-killing herbicide, has the characteristics of broad herbicidal spectrum, low toxicity, high activity and good environmental compatibility. Its activity speed is slower than that of paraquat, but better than that of glyphosate ; become a non-selective herbicide coexisting with glyphosate and paraquat, with broad application prospects; many weeds are sensitive to glufosinate-ammonium, and can be used as a substitute for glyphosate in glyphosate-resistant areas; among them , L-glufosinate-ammonium is the active ingredient in racemic glufosinate-ammonium, and its herbicidal activity is twice that of the racemate. In addition, the crystal structure of the active ingredient of the herbicide often causes differences in various physical and chemical properties of the ...

Claims

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Application Information

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IPC IPC(8): C07F9/30A01N57/20A01P13/00
CPCC07F9/301A01N57/20C07B2200/13Y02P20/55
Inventor 姜宇华
Owner SHANGHAI QIZHOU ZIYUE BIOTECHNOLOGY CO LTD
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