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Method for synthesizing Micromelalopha troglodyta sex pheromone active ingredient

A synthesis method and technology of active ingredients are applied in the field of synthesis of active ingredients of Yang Xiaozhou moth sex pheromone, can solve problems such as ecological risks, resistance problems, can not meet application requirements, etc., achieve low cost, reduce synthesis steps, and yield. high rate effect

Inactive Publication Date: 2020-01-24
INST OF FOREST ECOLOGY ENVIRONMENT & PROTECTION CHINESE ACAD OF FORESTRY +2
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

After the insect-resistant transgenic poplar is used for control, there are mainly the following problems: 1. Pests are easy to produce resistance to the transgenic (such as Bt) poplar; 2. The ecological risk caused by the release of the transgenic poplar to the environment
However, this component belongs to a new structural compound, and there is no commercial product at present, which cannot meet the actual application requirements

Method used

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  • Method for synthesizing Micromelalopha troglodyta sex pheromone active ingredient

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preparation example Construction

[0023] The invention provides a method for synthesizing the active ingredient of the sex pheromone of Yang Xiaozhou moth, comprising the following steps:

[0024] (1) 1,13-tridecanediol and aqueous hydrobromic acid are mixed for bromination reaction to obtain 13-bromo-1-tridecaneol;

[0025] (2) performing a phosphine salt synthesis reaction on the 13-bromo-1-tridecyl alcohol and triphenylphosphine to obtain tridecyltriphenylphosphine bromide;

[0026] (3) Under the action of a basic compound, the tridecyltriphenylphosphine bromide and trans-2-pentenal are subjected to a Wittig reaction to generate (Z,E)-13,15-octadecanedi Enol;

[0027] (4) Under the action of an oxidizing agent, the (Z,E)-13,15-octadecadienol is oxidized to obtain (Z,E)-13,15-octadecadienal, namely It is the active ingredient of the sex pheromone of Yang Xiaozhou Moth.

[0028] In the present invention, the active ingredient of the sex pheromone of Yang Xiaozhou moth is (Z,E)-13,15-octadecadienal, and its...

Embodiment 1

[0051] (1) Synthesis of 13-bromo-1-tridecanol

[0052] 1,13-Tridecanol (21.6g, 100mmol), toluene (analytical grade, 250mL) and 48wt% aqueous hydrobromic acid (13.5mL, 120mmol) were placed in a 500mL round bottom flask, and the reaction mixture was stirred and refluxed for 48h. TLC detection, until the disappearance of raw materials. After the reaction solution was cooled to room temperature, it was diluted with n-hexane. The obtained organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 13-bromo-1-tridecyl alcohol (27.5 g, 99%). The obtained product 13-bromo-1-tridecanol has high purity and can be directly used in the next reaction.

[0053] (2) Synthesis of Tridecyltriphenylphosphine bromide

[0054] 13-bromo-1-tridecanol (13.9g, 50mmol), triphenylphosphine (13.1g, 55mmol) and anhydrous acetonitrile (60mL) were placed in a 250mL three-neck round botto...

Embodiment 2

[0060] (1) Synthesis of 13-bromo-1-tridecanol

[0061] 1,13-Tridecanol (21.6g, 100mmol), toluene (analytical grade, 250mL) and 30% aqueous hydrobromic acid (13.5mL, 75mmol) were placed in a 500mL round bottom flask, and the reaction mixture was stirred and refluxed for 48h. TLC detection, until the disappearance of raw materials. After the reaction solution was cooled to room temperature, it was diluted with n-hexane. The obtained organic phase was washed with saturated aqueous sodium bicarbonate solution and saturated brine, respectively, and dried over anhydrous sodium sulfate. After distilling off the solvent, 13-bromo-1-tridecanol (27.5 g, 99%) was obtained. The obtained product 13-bromo-1-tridecanol has high purity and can be directly used in the next reaction.

[0062] (2) Synthesis of Tridecyltriphenylphosphine bromide

[0063]Place 13-bromo-1-tridecyl alcohol (13.9g, 50mmol), triphenylphosphine (13.1g, 55mmol) and anhydrous tetrahydrofuran (60mL) in a 250mL three-n...

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Abstract

The invention relates to the technical field of insect sex pheromone component synthesis, and provides a novel method for synthesizing Micromelalopha troglodyta sex pheromone active ingredient. According to the novel method, 1, 13-tridecanol is used as an initial raw material, cheap and easily available trans-2-pentenal is used as an intermediate, and (Z, E)-13, 15-octadecadienal can be synthesized through four steps of reaction. The preparation method provided by the invention has the advantages of accessible raw materials, lower cost and fewer synthesis steps; furthermore, the synthesis method provided by the invention is mild in condition, reagents with very harsh reaction conditions such as Grignard reagents and lithium reagents do not need to be used in the whole synthesis process, and the synthesis method is suitable for large-scale production; the synthesis method provided by the invention is simple and convenient in purification and relatively high in yield, in the whole synthesis route, only (Z, E)-13, 15-octadecadienol and (Z, E)-13, 15-octadecadienal need to be subjected to column chromatography purification, and the next step of reaction can be carried out through simple treatment in other steps.

Description

technical field [0001] The invention relates to the technical field of pest control, in particular to a method for synthesizing the active ingredient of the sex pheromone of the poplar moth. Background technique [0002] Micromelalophasieversi (Staudinger) belongs to Lepidoptera (Lepidoptera) and is one of the most serious leaf-eating pests in poplar plantations in my country in recent years. It is rampant in the Northeast, Northwest, Central Plains and Central South of my country. When it breaks out, it often eats up all the leaves, seriously affects the growth of trees, causes huge economic losses and environmental damage, and seriously restricts the development of forestry. [0003] Since the 1960s in our country, some scholars have conducted research on Yang Xiaozhou moth. Domestic scholars have made in-depth research on the biological behavior of Yang Xiaozhou moth, and achieved excellent results. At present, the main control measures adopted include the following fou...

Claims

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Application Information

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IPC IPC(8): C07C45/29C07C47/21
CPCC07C45/292C07C29/62C07F9/5407C07C29/34C07B2200/09
Inventor 刘福张真孔祥波张苏芳崔晓琦朱洪陈元兵李海涛
Owner INST OF FOREST ECOLOGY ENVIRONMENT & PROTECTION CHINESE ACAD OF FORESTRY
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