Preparation method of indoxacarb technical concentrate

Abstract

The invention discloses a preparation method of an indoxacarb mother drug, comprising the following steps: using 5-chloroindanone as a raw material to synthesize: (S)-5-chloro-2,3-dihydro-2-hydroxyl-1- Methyl oxo-1H-indene-2-carboxylate; from (S)-5-chloro-2,3-dihydro-2-hydroxy-1-oxo-1H-indene-2-methyl carboxylate and Benzyl carbazate is first condensed and then synthesized with diethoxymethane: 2‑benzyloxycarboxy‑7‑chloroindeno[1,2‑P][1,3,4]oxadiazine‑2, 4a-methyl carboxylate; use p-trifluoromethoxyaniline as raw material and methyl chloroformate, 1,2-diphenylethylenediamine as acid-binding agent to generate 4-(trifluoromethoxy)phenyl Methyl carbamate is then photoacylated with sodium methoxide to generate chloroformyl (4-trifluoromethoxyphenyl) methyl carbamate; by 2-benzyloxycarboxy-7-chloroindeno[1,2 ‑P][1,3,4]Oxadiazine‑2,4a‑carboxylate methyl ester is deprotected by hydrogenation, and then synthesized with methyl chloroformyl (4‑trifluoromethoxyphenyl) carbamate prestige. The invention has the advantages of high reaction yield, greatly improved production efficiency, high product purity and no pollution to the environment.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a new process for synthesizing the original drug of pymetrozine. Background technique [0002] Indoxacarb is a new type of oxadiazine insecticide developed by DuPont Company of the United States. It has been registered as a "reduced risk product" in the United States, Australia, China and other countries. Indoxacarb is a broad-spectrum insecticide that inhibits sodium channels. It is based on a new insecticidal mechanism, which is to block the sodium ion channel of nerve cells, thus reducing the possibility of cross-resistance with commonly used insecticides. Indoxacarb itself is a precursor insecticide, which is converted into an active compound by removing the methoxycarbonyl group (-COOCH3) on the amide nitrogen atom through metabolism in the insect body. It has high insecticidal activity over a broad spectrum and combines the advantages of good environmental compatibility, low tox...

AI Technical Summary

Problems solved by technology

Synthesis of indoxacarb Using (S)-5-chloro-2,3-dihydro-2-hydroxy-2-methoxycarbonyl-1-oxo-2H-indene-2-carboxylic acid methyl ester to synthesize indoxacarb It is the key intermediate of Weiwei, and there are disadvantages such as low product yield and low purity in the synthesis of this intermediate by conventional methods