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Aromatic amide compound comprising phosphoryl amino acid structure, preparation method of compound and application of compound taken as weed killer

A phosphoryl amino acid and aromatic amide technology, applied in the field of pesticide chemistry, can solve the problems of poor killing effect on broad-leaved weeds, serious resistance problems, slow drug response, etc., and achieve good herbicidal activity, rapid action, and high activity Effect

Inactive Publication Date: 2014-01-22
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the extensive application of glyphosate around the world, its resistance problem has become more and more serious, the dosage has increased, and the drug effect response has been slow. gramineous weeds

Method used

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  • Aromatic amide compound comprising phosphoryl amino acid structure, preparation method of compound and application of compound taken as weed killer
  • Aromatic amide compound comprising phosphoryl amino acid structure, preparation method of compound and application of compound taken as weed killer
  • Aromatic amide compound comprising phosphoryl amino acid structure, preparation method of compound and application of compound taken as weed killer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1. Preparation of compound C1 (N-(2-chloro-benzoyl)-N-phosphorylmethyl-glycine)

[0036] Add 0.01mol of glyphosate and 50ml of water to a 250ml four-necked bottle equipped with magnetic stirring, cooling, thermometer, and nitrogen protection, drop in 40% aqueous sodium hydroxide solution until the total amount of alkali is 0.04mol, cool and stir until The temperature of the system is 5°C, add 0.012mol of 2-chlorobenzoyl chloride tetrahydrofuran solution dropwise to the four-neck flask, after the dropwise addition, react at room temperature for 5 hours, stop stirring, separate the liquid to take the oil layer, and recrystallize methanol after rotary evaporation and precipitation , to obtain compound C1 with a yield of 65.5% and a purity of 99.6%.

[0037] The carbon spectrum data of N-(2-chloro-benzoyl)-N-phosphorylmethyl-glycine 13 C NMR (CDCl 3 )δ ppm =48.7,55.1,124.4,128.7,131.1,133.9,135.3,136.9,161.4,176.6.

[0038] After characterization, it was the tar...

Embodiment 2

[0039] Example 2, preparation of compound C2 (N-(4-chloro-benzoyl)-N-phosphorylmethyl-glycine)

[0040] Add 0.01 mol of glyphosate and 50 ml of dimethylformamide to a 250 ml four-neck flask equipped with magnetic stirring, cooling, thermometer, and nitrogen protection, drop 30% aqueous solution of sodium carbonate until the total amount of alkali is 0.03 mol, cool Stir until the system temperature is 10°C; add 0.015mol 4-chlorobenzoyl chloride dimethylformamide solution dropwise to the four-neck flask, after the dropwise addition, react at room temperature for 6 hours, distill under reduced pressure to remove the solvent, and dissolve in dichloromethane , washed with water, separated into the oil layer, recrystallized from methanol after rotary evaporation and desolventization, and obtained compound C2 with a yield of 69.4% and a purity of 99.8%.

[0041] The carbon spectrum data of N-(4-chloro-benzoyl)-N-phosphorylmethyl-glycine 13 C NMR (CDCl 3 )δ ppm =47.5,52.4,127.2,128...

Embodiment 3

[0043] Example 3. Preparation of compound C3 (N-(2,6-dichloro-benzoyl)-N-phosphorylmethyl-glycine)

[0044] Add 0.01mol of glyphosate and 50ml of dimethyl sulfoxide to a 250ml four-necked flask equipped with magnetic stirring, cooling, thermometer, and nitrogen protection, drop in 0.05mol of triethylamine, cool and stir until the system temperature is -5°C ; Add 0.011mol dimethyl sulfoxide solution of 2,6-dichlorobenzoyl chloride dropwise to the four-neck flask. After the dropwise addition, react at room temperature for 4 hours, and after desolvation by distillation under reduced pressure, dissolve dichloromethane and wash with water. The oil layer was obtained by liquid separation, methanol was recrystallized after rotary evaporation and desolventization, and compound C3 was obtained with a yield of 66.2% and a purity of 99.3%.

[0045] The carbon spectrum data of N-(2,6-dichloro-benzoyl)-N-phosphorylmethyl-glycine 13 C NMR (CDCl 3 )δ ppm =47.7,55.1,126.4,126.4,132.3,136.5...

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Abstract

The invention discloses an aromatic amide compound comprising a phosphoryl amino acid structure, a preparation method of the compound and an application of the compound taken as a weed killer. The structural formula of the aromatic amide compound comprising the phosphoryl amino acid structure is shown in a formula I, R represents substituted or un-substituted benzoyl, substituted or un-substituted benzene oxygen acetyl or replaced propenoyl. The preparation method of the aromatic amide compound shown as the formula I and comprising the phosphoryl amino acid structure comprises the steps as follows: under the catalytic action of alkali, glyphosate and an electrophilic reagent are subjected to electrophilic substitution reaction, so that the aromatic amide compound shown in the formula I is obtained; and the electrophilic reagent is substituted or un-substituted benzoyl chloride, substituted or un-substituted phenoxyacetyl chloride or replaced acryloyl chloride. The weed killer can be used for preventing and killing weeds, green bristle grass, crab grass, barnyard grass, quinoa, summer cypress, Xanthium sibiricum and piemarker.

Description

technical field [0001] The invention relates to an aromatic amide compound containing a phosphoryl amino acid structure, a preparation method thereof and an application as a herbicide, belonging to the field of pesticide chemistry. Background technique [0002] At present, the research and development of chemical pesticides focuses on the design and screening of compounds containing aromatic rings, heterocyclic rings and fused rings. Groups with different biological activities are combined in the same molecule to achieve superposition or enhancement of biological activity. Glyphosate is a phosphorus-containing amino acid herbicide developed by Monsanto Company of the United States in 1971. It is a high-efficiency, low-toxicity, broad-spectrum, non-selective post-emergence stem and leaf herbicide. The activity of enolpyruvylshikimate phosphate synthase, which disrupts the conversion of shikimelin to amino acids. Due to the invention and promotion of directional spraying equ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/38A01N57/22A01P13/00
Inventor 曹永松丁光龙耿倩倩刘瑶邓宇芳张文兵何顺郭明程段永恒李健强
Owner CHINA AGRI UNIV
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