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A clean and efficient synthesis process of metaflumizone

A technology of metaflumizone and its synthesis method, which is applied in the field of synthesis technology of metaflumizone, can solve the problems of high toxicity and long synthesis route, and achieve the effect of simple and easy steps and high reaction yield

Active Publication Date: 2020-03-24
YANGZHOU POLYTECHNIC INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

N-(4-trifluoromethoxyphenyl)carbamohydrazide is an important intermediate for the synthesis of metaflumizone, and the following route is often used to synthesize it at present: There is a long synthetic route, and many defects such as highly toxic methyl chloroformate or ethyl chloroformate are used in the reaction. Therefore, in order to overcome the defects of the prior art, the present invention discloses a method for preparing N-(4 - the method of trifluoromethoxyphenyl) carbamohydrazide, and further synthesize metaflumizone by this method

Method used

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  • A clean and efficient synthesis process of metaflumizone
  • A clean and efficient synthesis process of metaflumizone
  • A clean and efficient synthesis process of metaflumizone

Examples

Experimental program
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Effect test

Embodiment 1

[0015]

[0016] Weigh 1g of urea, add 5% available chlorine into sodium hypochlorite solution (15mL), 20% sodium hydroxide solution (5mL), stir at room temperature for 0.5h, then add 1.0mol / L 1-chloro-4-(tri Fluoromethoxy)benzene ethanol solution (1mL), heated to reflux temperature, after 24h of reaction, the reaction solution was poured into ice water (about 150mL) to produce a white solid, filtered, washed with water, and dried to obtain 220mg of white solid, collected The yield is about 93.6%, and the HPLC purity is 93.5%, which is consistent with the data of N-(4-trifluoromethoxyphenyl) carbamohydrazide detected by MS and NMR.

Embodiment 2

[0018]

[0019] Weigh 1g of urea, add 10% available chlorine to sodium hypochlorite solution (8mL), 30% sodium hydroxide solution (2mL), stir at room temperature for 1.0h, then add 0.6mol / L 1-bromo-4-(tri Fluoromethoxy)benzene ethanol solution (2mL), heated to reflux temperature, after 20h of reaction, the reaction solution was poured into ice water (about 150mL) to produce a white solid, which was filtered, washed with water, and dried to obtain 261mg of a white solid. The yield is about 92.5%, and the HPLC purity is 94.8%, which is consistent with the data of N-(4-trifluoromethoxyphenyl) carbamohydrazide detected by MS and NMR.

Embodiment 3

[0021] Replacing 1-chloro-4-(trifluoromethoxy)benzene in Example 1 with 1-iodo-4-(trifluoromethoxy)benzene can also obtain N-(4-trifluoromethoxy)benzene in a yield of 86%. Fluoromethoxyphenyl) carbamohydrazide.

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Abstract

The invention relates to a clean and efficient metaflumizone synthesizing process. The clean and efficient metaflumizone synthesizing process comprises the step of reacting a compound which is as shown in formula I and a compound which is as shown in formula II to generate metaflumizone in an organic solvent under the effect of a catalyst.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a clean and efficient synthesis process of metaflumizone. Background technique [0002] Metaflumizone is a semicarbazone insecticide jointly developed by German BASF and Japanese pesticide company. It is an insecticide with a new mechanism of action. Ion pass through, no cross-resistance with pyrethroids or other kinds of compounds. The drug mainly enters into the body of the pest to kill the pest through gastric poisoning, and the contact effect is small and has no systemic effect. Metaflumizone can be rapidly hydrolyzed and photolyzed in water, so it has no actual harm to aquatic organisms. Metaflumizone is a new type of high-efficiency, low-toxicity, environment-friendly pesticide that is safe for humans, crops and non-target pests. N-(4-trifluoromethoxyphenyl)carbamohydrazide is an important intermediate for the synthesis of metaflumizone, and the following rout...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C281/14C07C281/06
CPCC07C281/06C07C281/14
Inventor 王卫霞陈仕灵
Owner YANGZHOU POLYTECHNIC INST