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Synthetic method of diflubenzuron impurities for quantitative and qualitative analysis

A synthesis method and qualitative analysis technology, applied in chemical instruments and methods, preparation of urea derivatives, preparation of organic compounds, etc., can solve problems such as undisclosed synthesis methods, reduce environmental pollution and the impact of human health, improve quality effect

Pending Publication Date: 2021-06-08
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The above two impurities have not been controlled as known impurities of diflubenzuron in the existing reports, and the related synthesis methods have not been disclosed

Method used

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  • Synthetic method of diflubenzuron impurities for quantitative and qualitative analysis
  • Synthetic method of diflubenzuron impurities for quantitative and qualitative analysis
  • Synthetic method of diflubenzuron impurities for quantitative and qualitative analysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of N,N'-bis(4-chlorophenyl)biuret (impurity A)

[0037] (1) Preparation of 4-chlorophenylisocyanate

[0038] Add 4-chloroaniline (12.76g, 100.0mmol, 1.00eq.) and toluene (150mL) into the reaction flask, stir to dissolve 4-chloroaniline, then pass phosgene at 0-10°C, pass into phosgene ( 11.87g, 120.0mmol, 1.20eq.) After heating, the temperature rises to about 105°C, the material becomes transparent, and then reflux for a certain period of time, and N 2 Drive out phosgene, and distill under reduced pressure to obtain 4-chlorophenyl isocyanate. The product is light yellow to colorless oily liquid or solid, m.p.29~31℃, b.p.203~204℃, n 20 D 1.5618, relative density 1.200.

[0039] (2) Preparation of N,N'-bis(4-chlorophenyl)biuret (impurity A)

[0040] Add 4-chlorophenylisocyanate (3.08g, 20.0mmol, 1.00eq.), 4-chlorophenylurea (3.75g, 22.0mmol, 1.10eq.) and toluene (50mL) into the reaction flask, and heat up to 110°C The reaction was refluxed for 2 hours, a...

Embodiment 2

[0044] Preparation of N,N'-bis(4-chlorophenyl)biuret (impurity A)

[0045] Add 4-chlorophenylurea (7.95g, 46.6mmol, 0.93eq.) and toluene (75mL) into the reaction flask, heat up to 110°C, add dropwise 4-chlorophenylisocyanate (7.68g, 50.0mmol , 1.00eq.) of toluene (75mL) solution, after the dropwise addition, continue to reflux for 4h, sample HPLC to monitor the reaction. Cool to room temperature and filter, wash the filter cake with methanol to obtain a white solid, which is separated and purified by preparative liquid phase (mobile phase: methanol: water = 80:20) to obtain N,N'-bis(4-chlorophenyl)biuret.

Embodiment 3

[0047] Preparation of N,N'-bis(4-chlorophenyl)biuret (impurity A)

[0048] Add 4-chlorophenylurea (4.25g, 25.0mmol, 1.25eq.) and dichloroethane (50mL) into the reaction flask, heat up to 84°C, add dropwise 4-chlorophenylisocyanate (3.08g , 20.0mmol, 1.00eq.) in dichloroethane (50mL) solution, continue to reflux for 6h after the dropwise addition, sample HPLC to monitor the reaction. Cool to room temperature, concentrate under reduced pressure to remove the solvent, and obtain N,N'-bis(4-chlorophenyl)biuret through preparative liquid phase separation and purification.

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Abstract

The invention relates to a synthetic method of diflubenzuron impurities for quantitative and qualitative analysis, and belongs to the technical field of pesticide synthesis. The diflubenzuron impurities are synthesized in the following way, wherein R is the same or different and is independently selected from halogens; A is a chemical bond or carbonyl; m is 1 or 2; and n is 1 or 2. The two diflubenzuron bulk drug impurities are synthesized through experiments and can be used for qualitative and quantitative analysis of the diflubenzuron impurities, finally, the quality of the diflubenzuron bulk drug is further improved, and the influence of potential impurities brought by use of pesticide diflubenzuron on environment pollution and human body health is reduced.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, in particular to a method for synthesizing diflubenzuron impurities for quantitative and qualitative analysis. Background technique [0002] Diflubenzuron, chemical name: 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea, CAS accession number: 35367-38-5, common name: Diflubenzuron. It is an insect hormone-type insecticide. The main mode of action is stomach killing and contact killing. It prevents insect development and kills insects by interfering with the synthesis of insect chitin. It is highly toxic to crustaceans and silkworms. Biological safety, is a low-toxic and pollution-free pesticide. [0003] Although diflubenzuron itself is a low-toxic and pollution-free pesticide, in the production process, such as 4-Cl-Ph-NH 2 , COCl 2 , (COCl) 2 , SOCl 2 , HCl, NaOCN, H 2 SO 4 , PhCH 3 , KF, dichloroethane, sulfolane, N-methylpyrrolidone, γ-butyrolactone, dimethyl sulfoxide, N,N-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C273/18C07C275/62C07C263/10C07C265/12
CPCC07C263/10C07C273/1881C07C265/12C07C275/62
Inventor 孙传厚于连友王祥传李珂成道泉李洪侠李金鸿崔敏成晓彤张淑艳
Owner JINGBO AGROCHEM TECH CO LTD
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