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CN-121974828-A - Method for chiral resolution of clodinafop-propargyl enantiomer

CN121974828ACN 121974828 ACN121974828 ACN 121974828ACN-121974828-A

Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for chiral resolution of clodinafop-propargyl enantiomer. The invention adopts a high performance liquid chromatography-mass spectrometry technology to separate the clodinafop-propargyl enantiomer, the chromatographic column is a polysaccharide derivative chiral chromatographic column, the mobile phase A is an organic solvent, the mobile phase B is pure water, the mobile phase A is 40:60-100:0 according to the volume ratio, the elution is carried out at an isocratic, the column temperature is 30-35 ℃, and the flow rate is 0.5-0.8 mL/min. The invention provides a method for effectively separating chiral clodinafop-propargyl enantiomer, which has the advantages of high sensitivity, simple operation, high separation speed and the like.

Inventors

  • LIANG XIAO
  • DUAN SHUANG
  • FANG LE
  • Ai jiao
  • WANG NAN
  • LIU YUHUI
  • ZHOU XIANGHONG
  • XIE JIAJIAN

Assignees

  • 辽宁大学

Dates

Publication Date
20260505
Application Date
20260310

Claims (8)

  1. 1. A method for chiral resolution of the enantiomer of clodinafop-propargyl, comprising the steps of: 1) Preparing a test solution, namely weighing the clodinafop-propargyl, dissolving the clodinafop-propargyl in an organic solvent, and fixing the volume to prepare the test solution of the clodinafop-propargyl; 2) Separating the enantiomer of the clodinafop-propargyl in the test sample solution by adopting a high performance liquid chromatography-mass spectrometry technology, wherein a stationary phase is a polysaccharide derivative chiral chromatographic column, a mobile phase A is an organic solvent, and a mobile phase B is pure water, and performing isocratic elution; 3) Measured using an ultraviolet detector or a mass spectrum detector.
  2. 2. A process for chiral resolution of the enantiomer of clodinafop-propargyl according to claim 1, wherein in step 1) the organic solvent is one of methanol and acetonitrile.
  3. 3. The method for chiral resolution of an enantiomer of clodinafop-propargyl according to claim 1, wherein in step 1), the concentration of the test solution of clodinafop-propargyl is 10-500 ng/mL.
  4. 4. A method of chiral resolution of the enantiomers of clodinafop-propargyl according to claim 3, characterized in that in step 1) the concentration of the test solution of clodinafop-propargyl is 10 ng/mL.
  5. 5. A method for chiral resolution of clodinafop-propargyl enantiomers as claimed in claim 1, wherein in step 2), said polysaccharide derivative chiral chromatographic column is a polysaccharide derivative chiral chromatographic column with amylose-tris (3-chloro-5-methylphenyl carbamate) covalently bonded to the surface of silica gel.
  6. 6. The method for chiral resolution of clodinafop-propargyl enantiomer according to claim 1, wherein in the step 2), the mobile phase A is acetonitrile or methanol, the mobile phase A is 40:60-100:0 by volume ratio, the isocratic elution is carried out, the column temperature is 30-35 ℃, and the flow rate is 0.5-0.8 mL/min.
  7. 7. The method for chiral resolution of clodinafop-propargyl enantiomer according to claim 6, wherein in the step 2), the mobile phase A is acetonitrile, the mobile phase A is 80:20, the mobile phase B is eluted at an isocratic, the column temperature is 35 ℃, and the flow rate is 0.6 mL/min.
  8. 8. A method for chiral resolution of the enantiomer of clodinafop-propargyl according to claim 1, characterized in that in step 3) a mass spectrometric detector is used.

Description

Method for chiral resolution of clodinafop-propargyl enantiomer Technical Field The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for chiral resolution of clodinafop-propargyl enantiomer. Background A pesticide is defined by the united nations grain and agricultural organization (FAO) as a chemical substance for controlling harmful organisms, including single or mixed preparations of herbicides, insecticides, bactericides, disinfectants, and the like. In recent years, only a small part of pesticides applied in a large quantity to ensure high yield of crops are effective to target organisms, and most of residual pesticides enter the environment to pollute soil and water, so that human beings and other organisms are in a low-dose pesticide exposure environment for a long time. With the enhancement of environmental protection and health awareness, the research on the environmental behavior of pesticides is increasingly paid attention to. Chiral pesticides are of great interest as a class of special pesticides. About 40% of the commercial pesticides currently have chiral structures, but most are still used in racemic form. Due to the significant differences in environmental behavior, bioactivity and toxicity of chiral enantiomers, racemate pesticides are not only low in utilization, but also can increase environmental risks, and pose a potential threat to non-target organisms. Therefore, research on chiral pesticides from enantiomer level is of great importance for developing environmentally friendly, efficient, low-toxicity optically pure monomer pesticides. Clodinafop-propargyl (Buturon) was developed and introduced into the market in 1965 by bayer corporation of germany for pre-emergence weed control in cereal and corn fields. The biological activity, toxicity and environmental risks of the enantiomer of the configuration of the clodinafop-propargyl R, S are not reported in the literature at present, so that the establishment of a chiral resolution method of the clodinafop-propargyl enantiomer is particularly important for further research. Clodinafop-propargyl Disclosure of Invention The invention provides a method for chiral resolution of a clodinafop-propargyl enantiomer, which uses a high performance liquid chromatography-mass spectrometry technology to realize resolution of a clodinafop-propargyl R, S configuration. The technical scheme adopted by the invention is as follows: a method for chiral resolution of the clodinafop-propargyl enantiomer, comprising the steps of: 1) Preparing a test solution, namely weighing the clodinafop-propargyl, dissolving the clodinafop-propargyl in an organic solvent, and fixing the volume to prepare the test solution of the clodinafop-propargyl; 2) Separating the enantiomer of the clodinafop-propargyl in the test sample solution by adopting a high performance liquid chromatography-mass spectrometry technology, wherein a stationary phase is a polysaccharide derivative chiral chromatographic column, a mobile phase A is an organic solvent, and a mobile phase B is pure water, and performing isocratic elution; 3) Measured using an ultraviolet detector or a mass spectrum detector. Further, in the above method for chiral resolution of the enantiomer of clodinafop-propargyl, in step 1), the organic solvent is one of methanol and acetonitrile. Further, in the above method for chiral resolution of the clodinafop-propargyl enantiomer, in the step 1), the concentration of the clodinafop-propargyl sample solution is 10-500 ng/mL. Preferably, the concentration of the clodinafop-propargyl test sample solution is 10 ng/mL. In the above method for chiral resolution of clodinafop-propargyl enantiomer, in step 2), the polysaccharide derivative chiral chromatographic column is a polysaccharide derivative chiral chromatographic column with amylose-tris (3-chloro-5-methylphenyl carbamate) covalently bonded on the surface of silica gel. Further, in the above method for chiral resolution of clodinafop-propargyl enantiomer, in the step 2), the mobile phase A is acetonitrile or methanol, the mobile phase A is 40:60-100:0 by volume ratio, the column temperature is 30-35 ℃, and the flow rate is 0.5-0.8 mL/min. Preferably, the mobile phase A is acetonitrile, the mobile phase A is 80:20 according to the volume ratio, the isocratic elution is carried out, the column temperature is 35 ℃, and the flow rate is 0.6 mL/min. Further, in the above method for chiral resolution of the clodinafop-propargyl enantiomer, in step 3), a mass spectrum detector is used for measurement. The invention has the beneficial effects that the invention adopts the high performance liquid chromatography-mass spectrometry technology to directly and chiral split the clodinafop-propargyl, and the mobile phase of the invention consists of acetonitrile and pure water, and the method has the advantages of simple operation, high sensitivity, mild condition, short splitting time and