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Synthesis method for sex pheromone of ostriniafurnacalis

A synthetic method and a technology of corn borer sex, which is applied in the field of sex pheromones of the Asian corn borer, can solve the problems of high product impurities, many side reactions, and low solubility, and achieve the effects of high product purity, few side reactions, and economical process schemes

Inactive Publication Date: 2018-07-20
SHANDONG ACADEMY OF PESTICIDE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, the quaternary phosphonium salt of hydroxy reacts with a strong base to generate a sodium salt, which has low solubility in an organic solvent, and the reaction is a heterogeneous reaction; and it is not suitable for low-temperature reactions, and there are many side reactions, resulting in many impurities in the product and difficult post-treatment. Not conducive to large-scale production

Method used

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  • Synthesis method for sex pheromone of ostriniafurnacalis
  • Synthesis method for sex pheromone of ostriniafurnacalis
  • Synthesis method for sex pheromone of ostriniafurnacalis

Examples

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Effect test

Embodiment 1

[0081] A method for synthesizing the sex pheromone (Z, E)-12-tetradecen-1-ol acetate compound of Ostrinia officinalis, comprising the steps of:

[0082] (1) Synthesis of ω-bromododecyltriphenylphosphonium bromide salt

[0083] Put 16.40g (50mmol) of 1,12-dibromododecane and 13.10g (50mmol) of triphenylphosphine into 50ml of benzene, heat and reflux for 20h, after the reaction is over, pour out the benzene layer, and remove the residual benzene to obtain ω-bromododecyltriphenylphosphonium bromide salt 25.52g, yield 86.5%.

[0084] (2) Synthesis of ω-tetradecene bromide

[0085]Under the protection of nitrogen, 23.60g (40mmol) ω-bromoquaternary phosphine salt obtained in step (1) was added to the mixed solvent (5ml tetrahydrofuran and 5ml diglyme), stirred and dissolved and maintained at 20°C , slowly add 19.2ml 2.5mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stir the reaction for 1h, then cool down to -15°C, add 1.76g (40mmol) acetaldehyde in 2mL tetrahyd...

Embodiment 2

[0093] A method for synthesizing the sex pheromone (Z, E)-12-tetradecen-1-ol acetate compound of Ostrinia officinalis, comprising the steps of:

[0094] (1) Synthesis of ω-bromododecyltriphenylphosphonium bromide salt

[0095] Put 16.40g (50mmol) of 1,12-dibromododecane and 14.41g (55mmol) of triphenylphosphine into 50ml of benzene, heat and reflux for 18h, after the reaction is complete, pour out the benzene layer, and remove the residual benzene to obtain ω-bromododecyltriphenylphosphonium bromide salt 25.87g, yield 87.7%.

[0096] (2) Synthesis of ω-tetradecene bromide

[0097] Under the protection of nitrogen, add 29.50g (50mmol) ω-bromoquaternary phosphonium salt into the mixture of 25ml tetrahydrofuran and 5ml diethylene glycol dimethyl ether, stir to dissolve and maintain the temperature at 20°C-30°C, slowly add 40ml 2.5mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stirred for 1h, then cooled to -20°C, added 2.42g (55mmol) acetaldehyde in 2mL tetra...

Embodiment 3

[0105] A method for synthesizing the sex pheromone (Z, E)-12-tetradecen-1-ol acetate compound of Ostrinia officinalis, comprising the steps of:

[0106] (1) Synthesis of ω-bromododecyltriphenylphosphonium bromide salt

[0107] Put 32.80g (100mmol) of 1,12-dibromododecane and 39.27g (150mmol) of triphenylphosphine into 100ml of benzene, heat and reflux for 24 hours, and when the reaction is complete, pour out the benzene layer and remove the remaining benzene to obtain 53.57 g of ω-bromododecyltriphenylphosphonium bromide salt, yield 90.8%.

[0108] (2) Synthesis of ω-tetradecene bromide

[0109] Under the protection of nitrogen, add 35.40g (60mmol) ω-bromoquaternary phosphonium salt into the mixture of 60ml tetrahydrofuran and 6ml diethylene glycol dimethyl ether, stir to dissolve and maintain the temperature at 20°C-30°C, slowly add 50ml 3.0mol / L tetrahydrofuran solution of dimethyl sulfoxide sodium salt, stirred and reacted for 1.5h, then cooled to -5°C, added dropwise a m...

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Abstract

The invention discloses a synthesis method for a sex pheromone of ostriniafurnacalis, namely a (Z, E)-12-tetradecen-1-ol acetate compound. The synthesis method comprises the following steps: firstly,performing a reaction on 1, 12-dibromododecane and triphenylphosphine to produce omega-bromododecyltriphenylphosphonium bromide, then performing a reaction on the omega-bromododecyltriphenylphosphonium bromide and aldehyde under the action of organic alkali sodium dimethyl sulfoxide to produce Z-main type omega-bromotetradecene, then hydrolyzing by alkali metal hydroxide to obtain Z-main type (Z,E)-12-tetradecen-1-ol, performing an acetylation reaction on the (Z, E)-12-tetradecen-1-ol and acetic anhydride to obtain Z-main type(Z, E)-12-tetradecen-1-ol acetate, and performing an isomer conversion reaction on the Z-main type(Z, E)-12-tetradecen-1-ol acetate and a sodium nitrite and nitric acid solution to obtain E-main type(Z, E)-12-tetradecen-1-ol acetate. With the synthesis method, few side reactions occur in the synthesis process and the product purity is high.

Description

technical field [0001] The invention relates to a sex pheromone of the Asian corn borer, specifically a chemical synthesis method of (Z, E)-12-tetradecen-1-ol acetate compound, belonging to the technical field of biological pesticides. Background technique [0002] The Asian corn borer (Ostrinia furnacalis) belongs to the genus Ostrinia furnacalis of Lepidoptera and is the largest pest of corn. It is mainly distributed in Asia. Except for the Qinghai-Tibet Plateau corn area, it is distributed in other corn planting areas in my country. . Corn is an important field food crop. In 2016, the national corn planting area reached 36.76 million hectares, of which Jilin, Heilongjiang, Henan and Sichuan are more prone to hazards. In addition to harming corn, it can also harm more than 20 kinds of plants such as sorghum, millet, cotton, hemp, wheat, barley, potato, beans, sunflower, sugar cane, sugar beet, eggplant, and tomato. The damage characteristics of the Asian corn borer are as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/293C07C69/145C07C17/263C07C21/14
CPCC07B2200/09C07C17/2635C07C29/124C07C67/08C07C67/293C07F9/5442C07C69/145C07C33/025C07C21/14
Inventor 江忠萍李旭坤李金涛张作山刘钦胜王滢秀
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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