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Fluazuron and preparing method thereof

A technology of imidazoturon and synthesis method, which is applied in the fields of pesticides and organic chemistry, and can solve the problems of no reports on the application of ionic liquids, low product yield, low synthesis efficiency, etc., and achieve the reduction of by-product formation and high purity High, easy-to-operate effect

Inactive Publication Date: 2015-09-02
CHANGZHOU JIALING MEDICINE IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yet the synthetic efficiency of above-mentioned preparation method is not high, and product yield is lower
However, there is no report on the application of ionic liquids in the synthesis process of imidacloprone

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] 1) Preparation of 2,6 difluorophenyl isocyanate: put 62.6g (0.4mol) 2,6-difluorobenzamide, 101.5g (0.8mol) oxalyl chloride and 200mL toluene into the reaction flask, stir and reflux for 3 hours, Toluene and excess oxalyl chloride were distilled off under reduced pressure to obtain liquid intermediate I; 2) Preparation of 4-chloro 3-(3-chloro-5 trifluoromethylpyridyloxy)aniline: 87g (0.42mol) 2,3 di Chloro-5-trifluoromethylpyridine, 65.3g (0.45mol) 2-chloro-5-aminophenol, 70g (0.5mol) potassium carbonate, 5mmol1-butyl-3-methylimidazole hexafluorophosphate ionic liquid catalyst Add 250mL of toluene solvent into the reaction flask, heat up to 60°C under stirring, keep the temperature for 1 hour, distill off the solvent, add 250mL of water to precipitate a solid, filter, and wash the filter cake with water to obtain solid intermediate II with a yield of 98.2%; 3) Preparation of Imidazuron: put the above-mentioned liquid intermediate I, solid intermediate II and 300mL toluen...

Embodiment 2

[0019] 1) Preparation of 2,6 difluorophenyl isocyanate: 78.3g (0.5mol) 2,6-difluorobenzamide, 95.2g (0.75mol) oxalyl chloride and 200mL toluene were put into the reaction flask, stirred and refluxed for 8 hours, Toluene and excess oxalyl chloride were evaporated under reduced pressure to obtain liquid intermediate I; 2) Preparation of 4-chloro 3-(3 chloro-5 trifluoromethylpyridyloxy)aniline: 124.2g (0.6mol) 2,3 Dichloro-5-trifluoromethylpyridine, 84.7g (0.6mol) 2-chloro-5-aminophenol, 28g (0.7mol) sodium hydroxide, 6mmol1-butyl-3-methylimidazolium hexafluorophosphate ion Put the liquid and 300mL of toluene solvent into the reaction flask, heat up to 80°C under stirring, keep the temperature for 2 hours, distill off the solvent, add 300mL of water to precipitate the solid, filter, and wash the filter cake with water to obtain solid intermediate II with a yield of 97.9% ; 3) Preparation of imidacloprone: put the above-mentioned liquid intermediate I, solid intermediate II and 35...

Embodiment 3

[0021] 1) Preparation of 2,6-difluorobenzene isocyanate: 78.3g (0.5mol) 2,6-difluorobenzamide, 126.9g (1mol) oxalyl chloride and 200mL toluene were dropped into a reaction flask, stirred and refluxed for 6 hours, reduced Pressure steamed out toluene and excess oxalyl chloride to obtain liquid intermediate I; 2) Preparation of 4-chloro 3-(3 chloro-5 trifluoromethylpyridyloxy)aniline: 155.3g (0.75mol) 2,3 di Chloro-5-trifluoromethylpyridine, 130.6g (0.9mol) 2-chloro-5-aminophenol, 95.4g (0.9mol) sodium carbonate, 10mmol1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid Add 300mL of toluene solvent into the reaction flask, heat up to 70°C under stirring, keep the temperature for 3 hours, distill off the solvent, add 300mL of water to precipitate a solid, filter, and wash the filter cake with water to obtain solid intermediate II with a yield of 97.5%; 3) Preparation of Imidazuron: put the above-mentioned liquid intermediate I, solid intermediate II and 300mL toluene int...

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PUM

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Abstract

The invention relates to a synthesis method of an insecticide of fluazuron. According to the method, ion liquid is used as a catalyst, 2, 3 dichloro-5- (trifluoromethyl) pyridines, 2-chloro-5-aminophenol, 2, 6-difluorobenzamide and oxalyl chloride are used as raw materials, and the fluazuron is synthesized under the mild condition. The method has the advantages that the process is simple, the safety is high, the side reactions are few, the reaction time is short, and the yield is high. The yield of the fluazuron obtained by using the method is greater than 90 percent, and the purity is higher than 99 percent.

Description

technical field [0001] The invention relates to an insecticide-imidacloprid and a synthesis method thereof. Background technique [0002] Imidoxuron, also known as flufenuron, fluzolon, fluridoxuron, chemical name: 1-[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl ]-3-(2,6-difluorobenzoyl)urea belongs to benzoylurea insecticides, which can inhibit the synthesis of chitin in insects. Its insecticidal mechanism is unique, with high efficiency, broad spectrum, low toxicity, It is safe for humans and animals and is an environmentally friendly insecticide. Imidazuron is a parasite growth regulator, which has a good killing effect on ectoparasites of cattle, sheep, rabbits and other animals. [0003] The domestic patent (CN101209992A) reported a kind of 2-chloro-5-aminophenol, 2-chloro-5-aminophenol 2,6 difluorobenzamide and oxalyl chloride as raw materials, and synthesized acetaminophen through three-step pressure reaction The method of Long, there is certain poten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/643A01P7/04
CPCC07D213/643
Inventor 张月亮徐立新
Owner CHANGZHOU JIALING MEDICINE IND