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Novel method for preparing asiatic corn borer sex pheromone from tridecane compound

A technology of corn borer sex and thirteen carbons, which is applied in the field of preparation of sex pheromones of Asian corn borer, and can solve problems such as increasing the difficulty of use

Active Publication Date: 2014-04-02
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] 2. In some methods, the two components of cis and trans are prepared separately, and they can be used in the field after mixing in the later stage, which increases the difficulty of use

Method used

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  • Novel method for preparing asiatic corn borer sex pheromone from tridecane compound
  • Novel method for preparing asiatic corn borer sex pheromone from tridecane compound
  • Novel method for preparing asiatic corn borer sex pheromone from tridecane compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Take 1.2210g (5mmol) of 1,13-tridecanedioic acid in a dry 150ml round bottom flask, add 50ml of anhydrous THF (tetrahydrofuran) to dissolve, add 0.5690g (15mmol) of lithium aluminum hydride under ice bath and nitrogen protection, React at room temperature for 12 hours. After the reaction is over, add 10% (mass ratio) HCl solution dropwise under ice bath until the gas no longer escapes, filter with suction, wash the filter cake with 20ml of ethyl acetate for 3 times, and wash the filtrate with anhydrous MgSO 4 dry. After rotary evaporation, 1.0824 g of a white solid crude product was obtained, that is, the crude product of 1,13-tridecanediol, and the yield was combined with the next step for calculation.

Embodiment 2

[0048] Take 1.0818g (5mmol) crude product of 1,13-tridecanediol in a 250ml round-bottomed flask, add 40ml of cyclohexane to dissolve, stir to dissolve at 55°C, add dropwise to the reaction bottle within 10 minutes to dissolve in 30ml of water 23ml of glacial acetic acid, 0.08ml of concentrated sulfuric acid in water, react at 55°C for 10 hours, cool to room temperature, separate the liquids, and first use 20ml of saturated NaHCO for the organic phase 3 The solution was washed twice, and then washed twice with 20 ml of saturated brine, and rotary evaporated to obtain a crude product. Purified by column chromatography (petroleum ether:ether=3:1, volume ratio) to obtain 0.8398 g of white solid 13-hydroxytridecan-1-ol acetate, the total yield of 1-2 steps was 65 %.

Embodiment 3

[0050] Take 0.6466g (3mmol) PCC (pyridinium chlorochromate) in a 50ml round bottom flask, add 15ml of dichloromethane at room temperature to dissolve, add 0.5168g (2mmol) 13-hydroxytridecan-1-ol to the reaction flask Acetate, stirred at room temperature, monitored by TLC, the reaction was completed after 3 hours, filtered with suction, the filter cake was washed twice with 10ml of anhydrous ether, the filtrate was rotary evaporated, and the crude product was subjected to column chromatography (eluent was petroleum ether: ether=8 :1, volume ratio) purification to obtain 0.6466 g of the colorless oily liquid product 13-formyl tridecan-1-ol acetate, yield 95%.

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PUM

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Abstract

The invention discloses a novel method for preparing asiatic corn borer sex pheromone from a tridecane compound which is taken as an initial raw material, and belongs to the technical field of agricultural plant protection. The invention provides a novel method for preparing asiatic corn borer sex pheromone from a tridecane compound which is taken as an initial raw material. In particular, the invention first proposes an innovative and unique '13C+1C' synthesis strategy for chemical synthesis of the asiatic corn borer sex pheromone. The method disclosed by the invention has the characteristics of low raw material cost, short synthesis route, simple synthesis condition, high total yield and the like, and is applicable to industrial production.

Description

technical field [0001] The invention belongs to the technical field of agricultural plant protection, and in particular relates to a new method for preparing sex pheromone of corn borer using thirteen carbon compounds as starting materials. Background technique [0002] The Asian corn borer is a major pest in my country's cornfields. Among the various methods of preventing and controlling the Asian corn borer, the insect sex pheromone biological control method is characterized by its high sensitivity, strong selectivity, non-toxicity, no pollution to the environment, no killing of natural enemies, and is not easy to control. It has the advantages of producing pesticide resistance and conforms to the IPM (Integrated Pest Management) strategy. It is an internationally recognized green plant protection technology. It is of great significance to the protection of agricultural production, ecological security and sustainable agricultural development, and has been widely promoted and...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293
CPCC07C29/147C07C67/08C07C67/293C07C69/145C07C69/16C07C31/20
Inventor 刘伟张大伟潘洪玉杨鹏蒋龙杨国庆
Owner JILIN UNIV
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