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Synthetic method of diamondback moth sex pheromone compound

A synthetic method and pheromone technology, applied in the field of diamondback moth sex pheromone compound-11-hexadecenyl acetate, can solve the problem of polluting farmland, the surrounding environment of fruits and vegetables, affecting the health of consumers, and exceeding the standard of pesticide residues and other issues to achieve low prices, shorten the production cycle, and reduce production costs

Inactive Publication Date: 2012-11-28
昆明博鸿科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Farmers abuse highly toxic chemical pesticides, seriously polluting farmland, fruits and vegetables, and the surrounding environment, causing pesticide residues in fruit and vegetable products to seriously exceed the standard, seriously affecting the health of consumers
According to statistics, the diamondback moth has developed varying degrees of resistance to more than 50 insecticides such as organophosphates, pyrethroids, and Bacillus thuringiensis, and it is difficult to control its harm by relying solely on chemical control.

Method used

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  • Synthetic method of diamondback moth sex pheromone compound
  • Synthetic method of diamondback moth sex pheromone compound
  • Synthetic method of diamondback moth sex pheromone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Embodiment 1 11-hydroxyl undecyl alcohol acetate ( 5 ) preparation: 1,11-undecanediol ( 4 ) (18.8 g, 0.1 mol) was dissolved in 450ml of toluene, a catalytic amount of 98% concentrated sulfuric acid was added, and 50ml of toluene solution of glacial acetic acid (6 g, 0.1 mol) was slowly added dropwise, and continued to reflux at 120-125°C Stop the reaction after reacting for 18 hours, add saturated sodium carbonate to neutralize to pH=7-8, separate the toluene layer, extract the water layer with toluene three times, combine the organic layers, dry over anhydrous sodium sulfate and evaporate the solvent under reduced pressure Obtain crude product, through column chromatography (eluent is sherwood oil and ethyl acetate) purification obtains 11-hydroxy undecyl alcohol acetate ( 5 ) 19.3 g, yield 84%.

Embodiment 2

[0027] Embodiment 2 11-oxo undecyl alcohol acetate ( 6 ) preparation: 11-hydroxyl undecyl alcohol acetate ( 5 ) (18.4 g, 80 mmol) was dissolved in 400 ml of dry dichloromethane, cooling in an ice bath and adding pyridinium chlorochromate (25.86 g, 120 mmol) in batches under stirring, stirring at room temperature for 3 hours, adding an appropriate amount of water, separated dichloromethane, and extracted 2 times with dichloromethane, combined the organic layers, dried over anhydrous sodium sulfate and evaporated the solvent to obtain a crude product, which was purified by column chromatography (eluent was petroleum ether and ethyl acetate ) was purified to obtain 11-oxoundecyl acetate ( 6 ) 14.2 g, yield 78%, the crude product can also be directly used in the next reaction.

Embodiment 3

[0028] Embodiment 3 n-pentyltriphenylphosphine bromide ( 8 ) preparation: bromo-n-pentane ( 7 ) (0.1 mol, 15.1 g) and triphenylphosphine (0.1 mol, 26.2 g) were heated to 90°C for 30 hours and washed twice with ether to obtain n-pentyltriphenylphosphine bromide ( 8)38.4 g, yield 93%.

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Abstract

The invention discloses two synthetic methods of a diamondback moth sex pheromone compound. The first method adopts 1,11-undecadiol and n-amyl bromide as initial raw materials, and comprises four-step reactions including a critical Wittig reaction to synthesize (Z)-11-hexadecen-1-yl acetate, a hydrolytic reaction to obtain (Z)-11-hexadecen-1-ol, and a pyridinium chlorochromate oxidation reaction to obtain (Z)-11-hexadecenal. The second method adopts 1,11-undecadiol and valeraldehyde as initial raw materials, and comprises three-step reactions including a critical Wittig reaction to synthesize (Z)-11-hexadecen-1-ol, a pyridinium chlorochromate oxidation reaction to obtain (Z)-11-hexadecenal, and an esterification reaction to obtain (Z)-11-hexadecen-1-yl acetate. The invention has the advantages of cheap and easily available raw materials, simple synthetic route, mild reaction condition, convenient and safe operation, high yield, and low cost.

Description

technical field [0001] The present invention relates to two chemical compounds of diamondback moth sex pheromone compounds (Z)-11-hexadecenyl acetate, (Z)-11-hexadecenol and (Z)-11-hexadecenal resolve resolution. Background technique [0002] The diamondback moth (Plutella xylostella L.) belongs to the family Lepidoptera and is an important vegetable pest worldwide, seriously damaging cruciferous vegetables such as cabbage, cauliflower, and Chinese cabbage. The global annual cost of prevention and treatment is about 1 billion US dollars. Farmers abuse highly toxic chemical pesticides, seriously polluting farmland, fruits and vegetables and the surrounding environment, causing pesticide residues in fruit and vegetable products to seriously exceed the standard, seriously affecting the health of consumers. According to statistics, the diamondback moth has developed varying degrees of resistance to more than 50 insecticides such as organophosphates, pyrethroids, and Bacillus t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/145C07C67/293C07C67/08C07C47/21C07C45/29C07C33/025C07C29/34C07C27/02
Inventor 陶云海黄飞杨晓梅
Owner 昆明博鸿科技有限公司
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