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Method of preparing cydia molesta sex pheromone

A technology of sex pheromone and alcohol acetate of pear borer moth, which is applied in the field of preparation of sex pheromone of pear borer moth, and can solve problems such as difficulty in obtaining terminal alkyne, long route, harsh reaction conditions, etc.

Inactive Publication Date: 2008-09-24
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The above-mentioned synthetic route has the disadvantages that longer-chain terminal alkynes are not easy to obtain, and the route is longer, the total yield is lower, and the reaction conditions are harsh.
[0014] There are still many reports on the synthesis method of the sex pheromone of the pear borer, but the synthesis techniques are similar, only the choice of raw materials is different.

Method used

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  • Method of preparing cydia molesta sex pheromone
  • Method of preparing cydia molesta sex pheromone
  • Method of preparing cydia molesta sex pheromone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The synthesis of a, 8-bromo-1-octanol (III)

[0035] Add 14.6g (0.1mol) of 1,8-octanediol and 250mL of toluene into a 500mL round-bottomed flask, add 12.6mL of hydrobromic acid with a concentration of 40% dropwise for 10 minutes, and then reflux the system at 115°C for 10 minutes hour, then the system was lowered to room temperature, and 10 mL of hydrobromic acid with a concentration of 40% was added. After the addition was completed in 8 minutes, the system was divided into water and refluxed for 8 hours. TLC monitored the reaction process, and there was no raw material diol, only a small amount of dibromo , terminate the reaction, distill off the toluene, dissolve the residue with ether, and then use saturated NaHCO 3 The solution was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and silica gel column chromatography was used to obtain 18.03 g of 8-bromo-1-octanol (III) compound, a colorless liquid, wit...

Embodiment 2

[0043]The synthesis of a, 8-bromo-1-octanol (III)

[0044] Add 7.3g (0.05mol) of 1,8-octanediol and 150mL of toluene into a 250mL round-bottomed flask, add 13mL of hydrobromic acid with a concentration of 40% dropwise for 10 minutes, and then reflux the system at 115°C for 15 hours , then the system was lowered to room temperature, and TLC monitored the reaction process. There was no raw material diol, only a small amount of dibromo, the reaction was terminated, the toluene was evaporated, and the residue was dissolved in ether, followed by saturated NaHCO 3 The solution was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, solvent removed, and separated by silica gel column chromatography to obtain 8.66 g of 8-bromo-1-octanol (III) compound, a colorless liquid, with a yield of 83.2%;

[0045] B, the synthesis of 1-acetoxy-8-bromooctane (IV)

[0046] Weigh 4.16g (20mmol) of 8-bromo-1-octanol (III) in a 250mL round bottom bottle, add solve...

Embodiment 3

[0052] The synthesis of a, 8-bromo-1-octanol (III)

[0053] Add 11.68g (0.08mol) of 1,8-octanediol and 150mL of toluene into a 250mL round-bottomed flask, add 11mL of hydrobromic acid with a concentration of 40% dropwise for 10 minutes, and then reflux the system at 115°C for 10 hours , then the system was lowered to room temperature, and 8 mL of 40% hydrobromic acid was added. After the addition of 8 minutes, the system was divided into water and refluxed for 8 hours. TLC monitored the reaction process. There was no raw material diol, only a small amount of dibromo, The reaction was terminated, the toluene was evaporated, and the residue was dissolved in ether, followed by saturated NaHCO 3 The solution was washed with saturated brine, the organic layer was dried over anhydrous sodium sulfate, solvent removed, and separated by silica gel column chromatography to obtain 14.00 g of 8-bromo-1-octanol (III) compound, a colorless liquid, with a yield of 86.1%;

[0054] B, the syn...

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Abstract

The present invention relates to a preparation method of 8 (Z / E)-dodecylene-1-yl acetate of pheromone of oriental fruit moth of pests of fruit trees of the lep-idoptera tortricidae. In the method, 1, 8-octandiol is used as raw material, treated through unilateral bromination with hydrobromic acid, acetylated and transformed into aldehyde with N-oxidated pyridyl; finally the 1, 8-octandiol and bromide butyl triphenyl have the Scholer-Wittig reaction to synthesize the target compound. The method has the advantages of raw materials that can be easily prepared, simple process, mild conditions, high yield, low cost, suitability for large-scale production, and so on. The method provides necessary conditions for the wide application of the pheromone of oriental fruit moth to replace chemical pesticides so as to prevent and treat the pests of fruits, and has higher theoretical significance and excellent application value.

Description

technical field [0001] The invention relates to a preparation method of the sex pheromone 8(Z / E)-dodecen-1-ol acetate of the Lepidoptera Lepidopteran leaf tortriaceae fruit tree pest-the pear borer. Background technique [0002] Grapholitha molesta, also known as Grapholitha molesta for short, has another name called Oriental fruit borer moth, which belongs to Lepidoptera Lepidopteridae. It is distributed in the north and south fruit producing areas of my country, mainly harming pears and peaches, and also harming fruit trees such as apples, hawthorns, apricots, and jujubes. In recent years, the harm situation in Xinjiang has gradually intensified, which is the main factor posing a threat to the pollution-free production of fragrant pears and other fruits. The sex lure trapping method has no pollution, no pollution, and does not harm natural enemies and beneficial insects. It is a preferred biological control method. As early as 1969, Roelofs et al. identified the structur...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293A01P19/00
Inventor 李久明阿吉艾克拜尔·艾萨张生崔元玗
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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