Preparation method of mesosulfuron-methyl

The technology of methyldisulfuron-methyl and methoxycarbonylbenzenesulfonamide is applied in the field of preparation of herbicides, can solve the problems of removing impurities, many impurities and the like, and achieves the effects of high yield and high purity

Pending Publication Date: 2022-05-27
JIANGSU REPONT PESTICIDE FACTORY
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In this method, ethyl ester is used instead of phenyl ester to avoid the defect of by-product phenol, but the highest purity of the obtained product is only 96%, which may be due to long-term heating and reflux, and high temperature leads to more impurities, even if it is purified with isopropyl ether It is also difficult to completely remove impurities

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
  • Preparation method of mesosulfuron-methyl
  • Preparation method of mesosulfuron-methyl
  • Preparation method of mesosulfuron-methyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0028] The preparation method of methyldisulfuron-methyl of the present embodiment comprises the following steps:

[0029] ① Preparation of isocyanate.

[0030] Add 700g of dichloromethane and 35g of bis(trichloromethyl)carbonate to a dry 1000mL reaction flask, stir, and after the bis(trichloromethyl)carbonate is dissolved, cool the solution to 0-5 ℃, and add it to bis(trichloromethyl)carbonate. Trichloromethyl) carbonate solution was added dropwise with pyrimidinamine (compound III, 2-amino-4,6-dimethoxypyrimidine) solution (0.226 mol, 35 g of pyrimidinamine was dissolved in 100 g of dichloromethane), added After stirring for 20-60 min (30 min in this example), 100 g of acid binding agent triethylamine was added dropwise, and after the addition was completed, the mixture was stirred for 0.5-1 h to obtain an isocyanate (compound IV) solution for later use. During the reaction, the temperature was controlled below 50°C.

[0031] In addition to the above-mentioned dichlorometh...

Embodiment 2）

[0039] The rest of the preparation method of the methyldisulfuron-methyl of the present embodiment is the same as in Example 1, and the difference is:

[0040] Step 1 When preparing isocyanate, add 700 g of dichloromethane and 35 g of trichloromethyl chloroformate into a dry 1000 mL reaction flask.

[0041] The above-mentioned diphosgene and triphosgene can also be replaced by phosgene.

[0042] Step 2. After drying, 100 g of milky white powdery solid was obtained, the yield was 92%, and the purity detected by HPLC was 98.6% (see the HPLC detection map). figure 2 ).

Embodiment 3）

[0044] The rest of the preparation method of the methyldisulfuron-methyl of the present embodiment is the same as in Example 1, and the difference is:

[0045] Step 1 When preparing isocyanate, add 700g of toluene and 35g of bis(trichloromethyl)carbonate to a dry 1000mL reaction flask, stir, and cool the solution to 0~5 ℃ after the bis(trichloromethyl)carbonate is dissolved , add dropwise pyrimidineamine solution (0.226 mol, disperse 35g pyrimidineamine in 100g toluene to obtain suspension) to bis(trichloromethyl)carbonate solution, stir for 30min after adding, and then add dropwise 100g acid binding agent three Ethylamine was added and stirred for 1 h to obtain an isocyanate solution for later use.

[0046] The solvent in step ② is toluene.

[0047] Step 2. After drying, 102 g of milky white powdery solid was obtained, the yield was 93%, and the purity detected by HPLC was 98.2% (see the HPLC detection map). image 3 ).

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 discloses a mesosulfuron-methyl preparation method, which comprises the following steps: reacting pyrilamine with a carbonyl chloride compound to obtain isocyanate, and condensing the isocyanate with 5-methylsulfonylaminomethyl-2-methoxycarbonyl benzenesulfonamide to obtain mesosulfuron-methyl. The method disclosed by the invention is high in yield, the prepared product is high in purity, and byproducts generated in the preparation process are few and are easy to recover.

Description

technical field [0001] The invention relates to a preparation method of a herbicide, in particular to a preparation method of a sulfonylurea herbicide methyldisulfuron. Background technique [0002] Methyldisulfuron, also known as Mesosulfuron-methyl, is a new type of sulfonylurea herbicide developed by Aventis (later acquired by Bayer) in 1993. It belongs to the synthesis of sulfonylurea acetolactate. Enzyme (ALS) inhibitor, mainly used for weeding in winter wheat fields, can control annual broad-leaved weeds and some grass weeds, such as sagebrush, wild oat, bat grass, bluegrass, hard grass, lysine , multi-flowered ryegrass, poisonous barley, brome, candle grass, festival wheat, chrysanthemum grass, ice grass, shepherd's purse, sophora japonica, beef chickweed, self-growing rape, etc. [0003] The mechanism of action of methyldisulfuron is an ALS inhibitor, which is mainly absorbed through the stems and leaves of plants, conducted through the phloem and xylem, and inhibit...

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): C07D239/52
CPCC07D239/52
Inventor 杨晓放步康明步成伟顾小雨颜建忠步杰汪兴园
Owner JIANGSU REPONT PESTICIDE FACTORY
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

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap