Method for synthesizing intermediate of agricultural insecticide indoxacarb

A technology for indoxacarb and intermediates, which is applied in the field of new synthetic techniques for intermediates of indoxacarb for agricultural insecticides, can solve problems such as low yields, and achieve the effects of increasing reaction temperature, reducing decomposition and improving overall yields

Active Publication Date: 2015-01-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, when the method for cyclization is carried out according to the literature report, the yield is on the low side. The main reason is that the raw material hydrazone (YCW-4) is easily decomposed into 5-chloro-2,3-dihydro-2-hydroxyl-1-oxygen during cyclization. Generation-1H-indene-2-carboxylate methyl ester (YCW-3), the reaction temperature of this method is 80-85°C

Method used

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  • Method for synthesizing intermediate of agricultural insecticide indoxacarb
  • Method for synthesizing intermediate of agricultural insecticide indoxacarb
  • Method for synthesizing intermediate of agricultural insecticide indoxacarb

Examples

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Embodiment 1

[0040] Embodiment 1, a kind of synthetic method of agricultural insecticide indoxacarb intermediate, carries out following steps successively:

[0041] 1) Add 10g of YCW-4 (0.026mol), 0.45g of p-toluenesulfonic acid (0.0026mol), and 50mL of toluene (with anhydrous treatment) into a 250mL four-neck flask with a fractionation device, and heat to reflux into the thorn-shaped fractionation column Droplets are formed, and the temperature in the four-necked bottle is T l is 108°C, the temperature T at the top of the thorn-shaped column 2 When the temperature is 106°C, start to intermittently add a mixed solution consisting of 10mL diethoxymethane (0.08mol) and 30mL toluene, the reflux temperature of the reaction solution will decrease during the dropwise addition, when the top temperature T 2When it is lower than 92°C, stop the dropwise addition, and start to separate part of the liquid to the temperature T at the top of the thorn-shaped column 2 Return to 92°C, stop the distillat...

Embodiment 2

[0043] Embodiment 2: a kind of synthetic method of agricultural insecticide indoxacarb intermediate, carry out following steps successively:

[0044] 1), add 10g YCW-4 (0.026mol), 0.83g ammonium diphenyltrifluoromethanesulfonate (0.0026mol), 50mL toluene (after anhydrous treatment) to a 250mL four-neck flask with a fractionation device, heat Droplets are generated in the backflow to the thorn-type reflux column, and the temperature T in the four-necked bottle is now l is 108°C, the temperature T at the top of the thorn-shaped column 2 When the temperature is 106°C, intermittently drop the mixed solution consisting of 10mL diethoxymethane and 30mL toluene, the reflux temperature of the reaction solution will decrease during the dropwise addition, when the top temperature T 2 When it is lower than 92°C, stop the dropwise addition, and start to separate part of the liquid to the temperature T at the top of the thorn-shaped column 2 Return to 92°C, stop the distillation operatio...

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Abstract

The invention discloses a method for synthesizing an intermediate of agricultural insecticide indoxacarb. The method comprises the following steps: (1) putting YCW-4, Lewis acid and methylbenzene into a reaction container according to a proportion, stirring, heating to a reacting temperature of 105-110 DEG C, dripping a methylbenzene solution of diethoxymethane, adding benzyl carbazate, and reacting at the reacting temperature until the reaction is carried out completely, wherein azeotrope of ethanol and diethoxymethane serving as a byproduct is constantly vaporized and eliminated in the reacting process; (2) stopping heating after the reaction is finished, cooling to room temperature under a stirring condition, concentrating at reduced pressure to reclaim methylbenzene, cooling and crystallizing the concentrate at low temperature by using a crystallization solvent, suction-filtering, washing, and baking to obtain light yellow crystal which is a target product, namely the intermediate of agricultural insecticide indoxacarb. The synthesizing method has the technical advantage of high yield.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a new synthesis process of an agricultural insecticide indoxacarb intermediate. Background technique [0002] Indoxacarb (see formula 1 for the structural formula), chemical name: 7-chloro-2,3,4a,5-tetrahydro-2(methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl)indene And (1,2-e)oxadiazine-4a-carboxylic acid methyl ester, common name: indoxacarb, trade name: Ammate, Avatar, etc. This product is a new type of oxadiazine chiral insecticide launched by DuPont of the United States in 2001, and it is also the first commercialized sodium channel blocking insecticide. Indoxacarb has a novel structure, a unique mechanism of action, low dosage, and is effective against almost all Lepidoptera pests. It is safe for humans, animals, the environment, crops, non-target organisms, and beneficial organisms. It is an ideal agent for resistant insecticides, and has broad market and application pro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/04
CPCC07D273/04
Inventor 程敬丽赵金浩郑敏姜忠义郑乐贵
Owner ZHEJIANG UNIV
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