Improved method for synthesizing clethodim

A synthetic method, the technology of clethodim, applied in the field of improved clethodim synthesis, can solve problems such as non-compliance, unfavorable industrial production, and affecting the quality of clethodim, and achieve the effects of good quality, easy industrial production, and simple operation

Active Publication Date: 2017-03-22
HEBEI LANSHENG BIOTECH CO LTD
View PDF3 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Because the above formula compound (II) affects the quality of clethodim, it does not meet the international regulations on pesticide impurity limits, and how to reduce the impurity compound (II) in the product in this synthetic route has not yet been reported.
[0013] Another clethodim synthesis route reported in U.S. Patent Document US 4440566 has fewer impurity compounds (II) in the product, but it is difficult to obtain the product with a high yield. In addition, a large amount of waste water will be produced, which is not conducive to industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Improved method for synthesizing clethodim
  • Improved method for synthesizing clethodim
  • Improved method for synthesizing clethodim

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put 43 grams (0.25mol) of compound (Ⅲ) and 100 grams of toluene into a 500ml three-necked flask, then add 0.43 grams of methyl propionate and 33 grams (0.25mol) of dimethyl malonate, cool to room temperature, drop 65 grams (0.3 mol) of sodium methoxide methanol solution with a content of 25%, and then the mixture was stirred overnight at room temperature. After the completion of the reaction was determined by thin layer chromatography, heating and distillation was added and 100 grams of toluene was added until there was no alcohol to obtain the compound ( IV). After cooling, 23 g (0.25 mol) of propionyl chloride was added dropwise at 60-70° C. After the drop, the temperature was raised to 90° C. and kept for 2 hours to obtain compound (Ⅴ). Adjust the pH to 7 with triethylamine, then add 2 g of 4-dimethylaminopyridine, and react at 90° C. for 4 hours to obtain compound (VI). Then add 100 g of water and 80 g (0.6 mol) of 30% liquid caustic soda, react at 90°C for 4 hours...

Embodiment 2

[0028] Put 43 g (0.25 mol) of compound (Ⅲ), 100 g toluene and 33 g (0.25 mol) of dimethyl malonate into a 500 ml three-necked flask, cool to room temperature, and add dropwise 25% sodium methoxide methanol solution 65 g (0.3 mol), then 1.5 g of methyl propionate was added, and the mixture was stirred overnight at room temperature, and the reaction was complete as determined by thin layer chromatography. Subsequent steps were continued as described in Example 1. 52.7 g of compound (Ⅷ) was obtained in the middle, and by high-performance liquid chromatography analysis, the purity was 91.0%, the yield was 71%, and the ratio of compound (IX) was 0.25% by weight. Finally, 69.4 g of compound (I) was obtained. Through high-performance liquid chromatography analysis, the purity was 92.8%, the total yield was 71.6%, and the proportion of compound (II) was 0.25% by weight.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to an improved method for synthesizing clethodim. The method includes the step that propanoic acid C1-C6 alkyl ester is added into any procedure in the first step of reaction of a synthetic route shown in the formula (1). The formula (1) is defined in the description.

Description

technical field [0001] The present invention relates to an improved synthesis method of clethodim. Background technique [0002] Clethodim, the chemical name is 2-{1-[(3-chloro-2-allyl)oxy]iminopropyl}-5-[2-(ethylthio)propyl]-3-hydroxy -2-cyclohexen-1-one is a broad-spectrum post-emergent herbicide for controlling gramineous weeds in broadleaf crops released by Chevren Chemical Company of the United States. Weeds have a strong killing effect and are safe to dicotyledonous crops. Clethodim is rapidly absorbed by the leaves after stem and leaf treatment, and is transmitted to the meristematic tissue. In sensitive plants, it acts by inhibiting the biosynthesis of branched-chain fatty acids and flavonoids, destroying plant cell division, and inhibiting plant growth. The activity of the living tissue, thereby delaying the growth of the plant. The plants chlorotic and necrotic within 1 to 3 weeks after application, and then the leaves withered and died. Clethodim is mainly sui...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/47C07C319/20
CPCC07C319/20C07C323/47C07C323/22C07C323/55
Inventor 许峰
Owner HEBEI LANSHENG BIOTECH CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products