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A kind of preparation method of indoxacarb insecticide

A technology of indoxacarb and insecticides, which is applied in the field of preparation of indoxacarb insecticides, can solve the problems of affecting the content of indoxacarb products, difficult recovery of mixed solvents, and easy generation of impurities, so as to avoid decomposition and impurities The production and operation are simple and feasible, and the production cost is reduced

Active Publication Date: 2019-07-12
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction solvents used in the existing process, such as dimethyl carbonate and diethoxymethane, have a low boiling point, and toluene will be by-produced in the reaction process, and the final mixed solvent is difficult to recover
At the same time, the existing production process uses a water-containing catalyst, and the intermediate raw material N-chloroformyl-N-[4-(trifluoromethoxy) phenyl] methyl carbamate used in the reaction process is unstable and decomposes when encountering water. Impurities are easily produced during the process, thus affecting the product content of indoxacarb

Method used

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  • A kind of preparation method of indoxacarb insecticide
  • A kind of preparation method of indoxacarb insecticide

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Experimental program
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Embodiment 1

[0025] (1) 81.6g (0.2mol) 7-chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3H,5H)- Dicarboxylic acid-4a-methyl-2-benzyl ester, 400g toluene, heat up to 25°C, then put 0.4g of Pd-C catalyst and 0.2g of tetrabutylammonium bromide into the reaction flask, start to pass hydrogen to control the hydrogen flow rate 500mL / min;

[0026] (2) Sampling and testing after hydrogenation for 4 hours, after the reaction is qualified (reaction is complete if the remaining amount of raw material is less than 1%), suction filtration; hydrogenation catalyst and phase transfer catalyst are suction filtered out (catalyst is a solid suspension, requiring suction) The filtrate is clear and transparent, and leakage cannot occur), so as to obtain the reaction solution a, the product contained in the reaction solution is the hydrogenated product of intermediate I, that is, the hydrogenation reduction product of the raw material;

[0027] (3) 74.25g N-chloroformyl-N-[4-(trifluoromethoxy)phenyl]methyl carbamat...

Embodiment 2

[0031] (1) 81.6g (0.2mol) 7-chloroindeno[1,2-e][1,3,4]oxadiazine-2,4a(3H,5H)- Dicarboxylic acid-4a-methyl-2-benzyl ester, 400g toluene, heat up to 25°C, then put 0.4g of Pt-C catalyst and 0.2g of tetrabutylammonium chloride into the reaction bottle, start to pass hydrogen to control the hydrogen flow rate 300mL / min.

[0032] (2) Sampling and testing after hydrogenation for 4 hours, after the reaction is qualified (reaction is complete if the remaining amount of raw material is less than 1%), suction filtration; hydrogenation catalyst and phase transfer catalyst are suction filtered out (catalyst is a solid suspension, requiring suction) The filtrate is clear and transparent, and there can be no leakage), to obtain the reaction solution a, and the product contained in the reaction solution is intermediate I hydrogenolyzate, that is, the hydrogenation reduction product of the raw material.

[0033] (3) 59.4g N-chloroformyl-N-[4-(trifluoromethoxy)phenyl]methyl carbamate (0.2mol)...

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Abstract

The invention relates to a preparation method of an indoxacarb insecticide and provides a synthesis method capable of avoiding use of a mixed solvent and heterogeneous reaction. The solvents, such as methyl acetate, dimethyl carbonate and diethoxymethane are replaced with methylbenzene, so that use of the mixed solvent is avoided, the problem of reuse of a reaction solvent is solved, the solvent recovery rate is improved and the production cost is reduced. The mode of a water dispersion catalyst in the literature is replaced with a hydrogenation catalyst with high dispersity; use of water is concealed, hydrolysis of a raw material N-chloroformyl-N-[4-(trifluoromethoxy) phenyl] methyl carbamate is avoided, the raw material is saved, impurity is avoided, the production cost is reduced and the quality of a product is improved. A nonpolar alkane solvent is adopted in the post-treatment crystallization process of the product, so that the yield of the product is further improved and is superior to that of an existing production technology and a good foundation is laid for production of high-quality indoxacarb.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and relates to a preparation method of indoxacarb insecticide. Background technique [0002] Indoxacarb is an oxadiazine insecticide developed by DuPont of the United States in 1992 and registered in 2001. Its active ingredient is indoxacarb, and its chemical name is 7-chloro-2,3,4a,5-tetrahydro-2- Methyl [methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl]indeno[1,2-e][1,3,4-]oxadiazine-4a-carboxylate. Its insecticidal mechanism is mainly as a sodium channel inhibitor, mainly blocking the sodium channel in the nerve cells of pests, leading to coordinated paralysis and eventual death of target pests. The pesticide enters the insect body through contact killing and ingestion, and the behavior of the pest changes rapidly, causing the pest to stop feeding quickly, thus excellently protecting the target crop. Tests showed that indoxacarb had no cross-resistance with other insecticides. This ins...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/12A01N47/38
CPCA01N47/38C07D271/12
Inventor 薄蕾芳刘花敏李响刘建成王建刚李洪侠韦能春
Owner JINGBO AGROCHEM TECH CO LTD
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