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Synthetic method of triolefin insect sex attractant

A synthetic method and insect-based technology, which are applied in the field of synthesis of triene-based insect sex attractants, can solve the problems of few literature reports on the chemical synthesis of triene-based sex pheromones, the difficulty of synthesizing the second type of sex pheromone, and the intermediate The product needs to be separated and other problems to achieve the effect of high yield, low cost and easy separation

Inactive Publication Date: 2013-08-28
SHANXI AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, a variety of sex attractants have been synthesized by artificial synthesis and have been commercialized, but the second type of sex pheromones is more difficult to synthesize. There have been many reports on the chemical synthesis of epoxy olefin sex pheromones, but three There are very few literature reports on the chemical synthesis of olefinic sex pheromones
At present, the synthesis method of triene sex pheromone compounds is difficult to obtain products, and at the same time, there are different shortcomings such as expensive raw materials, low yield, toxic solvents, cumbersome operations, and the need to separate intermediate products.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis method of cis,cis,cis-3,6,9-nonadecatriene

[0023] (1) Add 4.5g LiAlH 4 With 80mL of anhydrous ether, under the protection of nitrogen, slowly drop 25g of α-linolenic acid ethyl ester and 80mL of anhydrous ether into the flask in the constant pressure dropping funnel for 60min, and keep stirring. After the dropwise addition, Heat to reflux for 1h, then cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 5% dilute sulfuric acid until clarified, the mixture was transferred to a separatory funnel, extracted three times with ether and the organic phases were combined, washed with saturated sodium chloride until neutral, dried over anhydrous sodium sulfate for 12 hours, evaporated and distilled under reduced pressure to obtain α-linalenol 25g, the productive rate is 80%.

[0024] (2) In a 250mL standard ground three-neck flask equipped with a constant pressure droppi...

Embodiment 2

[0028] Synthetic method of cis, cis, cis-3,6,9-eicosatriene

[0029] (1) Add 8.5g LiAlH 4 With 160mL of anhydrous ether. Under the protection of nitrogen, slowly drop 65g of ethyl α-linolenic acid and 160mL of anhydrous ether into the flask in the constant pressure dropping funnel for 1-2 h, and keep stirring. After the dropwise addition, heat to reflux for 1- 3h, after the reaction is over, cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 15% dilute sulfuric acid until clear, the mixture was transferred to a separatory funnel, extracted three times with ether and combined organic phases, washed with saturated sodium chloride until neutral, and dried over anhydrous sodium sulfate for 48h. Evaporate the solvent and distill under reduced pressure to obtain 65 g of α-linolenic alcohol with a yield of 80%.

[0030] (2) In a 250mL standard ground three-neck flask equipped with a c...

Embodiment 3

[0034] Synthetic method of cis, cis, cis-3,6,9-undecatriene

[0035] (1) Add 6.5g LiAlH 4 With 100mL of anhydrous ether. Under the protection of nitrogen, slowly drop 40g of ethyl α-linolenic acid and 90mL of anhydrous ether into the flask in the constant pressure dropping funnel for 1-2h, and keep stirring. After the dropping is completed, heat and reflux for 2-3h , after the reaction is over, cool to room temperature, add a small amount of distilled water to hydrolyze the excess LiAlH in an ice-water bath 4 , and then acidified with 10% dilute sulfuric acid until clarified, the mixture was transferred to a separatory funnel, extracted three times with ether and the combined organic phase was washed with saturated sodium chloride until neutral, and dried over anhydrous sodium sulfate for 30 h. Evaporate the solvent and distill under reduced pressure to obtain 52 g of α-linolenic alcohol with a yield of 78%.

[0036] (2) In a 250mL standard ground three-neck flask equ...

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PUM

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Abstract

The invention discloses a synthetic method of a triolefin insect sex attractant. The synthetic method comprises the steps of (1) enabling alpha-ethyl linolenate to react with absolute ether to generate alpha-linoleny alcohol under catalytic action of LiAlH4; (2) enabling the alpha-linoleny alcohol to react with phosphorus tribromide to generate cis, cis, cis-1-bromine-9,12,15-gadusene in the presence of an organic solvent with weak polarity; and (3) enabling the cis, cis, cis-1-bromine-9,12,15-gadusene to react with a grignard reagent to generate cis, cis, cis-3,6,9-Cn triene under the effects of tetrahydrofuran, lithium tetrachlorocuprate and N-methyl pyrrolidone. By adopting the synthetic method of the triolefin insect sex attractant disclosed by the invention, an insect in-vivo biosynthetic pathway is simulated; polyene hydrocarbon information sex pheromone components of C19, C20 and C21 are synthesized by taking cheap and available alpha-ethyl linolenate as the material; and the synthetic method is short in technologic process, mild in synthetic reaction condition, short in reaction time, high in yield, simple and convenient to operate, wide in application range, low in cost, fewer in three wastes, little in environmental pollution, and easy to industrialize, and the product can be easily separated.

Description

technical field [0001] The invention relates to a synthesis method of an insect sex attractant, in particular to a synthesis method of a triene insect sex attractant. Background technique [0002] Insect pests are one of the important problems restricting agricultural production, often causing large-scale crop production reduction or even failure, resulting in serious economic losses. With the progress of society and the widespread concern of humans on healthy food safety, pest control strategies are increasingly developing in the direction of pest management (SPM), ecological management (EPM), and sustainable management (SPM). In the process of agricultural production, new and pollution-free pest control technologies are gradually replacing traditional chemical control, and are playing an increasingly important role in integrated pest control. [0003] The use of artificially synthesized attractants to trap and kill insects is an efficient, non-toxic and non-polluting new ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N27/00A01P19/00C07C11/21C07C2/86
Inventor 张金桐郑海霞赵志国荣二花宗世祥骆有庆阎义冯帅
Owner SHANXI AGRI UNIV
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