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Synthetic method of hyphantria cunea sex pheromone components

The invention relates to a technology of American white moth and a synthetic method, which is applied in the directions of organic chemical methods, chemicals for biological control, and pest control, etc., and can solve the problems of inability to obtain sulfonic acid esterification products, difficult reaction control, and high reactivity. Achieve the effect of low cost, prevention of excessive hydrogenation, and simple reaction conditions

Active Publication Date: 2020-02-28
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through synthesis research, we found that trifluoromethanesulfonic acid anhydride has high reactivity and oxidative properties, and the reactivity of the trifluoromethanesulfonate ester generated by the reaction is also very high, and side reactions such as elimination and substitution are prone to occur; therefore, even The sulfonate is carried out at about -80°C, the reaction is still difficult to control, the yield is only 20%, and even the sulfonate product cannot be obtained

Method used

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  • Synthetic method of hyphantria cunea sex pheromone components
  • Synthetic method of hyphantria cunea sex pheromone components
  • Synthetic method of hyphantria cunea sex pheromone components

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Sex pheromone components of American white moth (3Z, 6Z, 9S, 10R)-9, 10-epoxy-3, 6-unicosadiene (I) and (3Z, 6Z, 9S, 10R)-9 , 10-epoxy-1,3, the route of the synthetic method of 6-undecatriene (II) is as follows:

[0042]

[0043] Specific steps include:

[0044] Step 1 Synthesis of compound 2

[0045] Dissolve 2.3 g of compound 1 in 100 ml of dichloromethane, stir to dissolve, add 3.2 g of triphenylphosphine, stir to dissolve, cool to -5°C with ice salt, add 4 g of tetraphenylphosphine in batches within 1 hour Carbon bromide; rise naturally to room temperature for reaction, TLC detects that the reaction is over, add 400 milliliters of sherwood oil and stir for 30 minutes, filter with suction, concentrate the filtrate film, and purify the residue by column chromatography (V (ethyl acetate): (petroleum ether) = 1:30) to obtain 2.7 g of compound 2 (93% yield).

[0046] Step 2 synthesis of compound 5

[0047]Dissolve 1.4 g of 1,4-heptadiyne (compound 3) in 100 ml of ...

Embodiment 2

[0055] The American white moth sex pheromone component (3Z, 6Z, 9S, 10R)-9,10-epoxy-3,6-eicosadiene, (3Z, 6Z, 9S, 10R)-9,10-epoxy-1,3,6-eicosatriene, (9Z,12Z,15Z)-octadecatrienal (refer to Jiefeng Hu, Xiaowei Han, Yu Yuan, ZhuangzhiShi.Angew.Chem.Int.Ed.2017, 56:13342-13346.) The three components were dissolved in 100μL redistilled distilled In methyl chloride, a certain concentration of white moth sex pheromone solution was prepared, placed in the refrigerator, and stored at -20°C for later use.

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Abstract

The invention discloses a synthetic method of hyphantria cunea sex pheromone components, and belongs to the technical field of chemical production. (2S, 3R)-2, 3-epoxy-1-tetradecanol is used as a rawmaterial, and the hyphantria cunea sex pheromone components (3Z, 6Z, 9S, 10R)-9, 10-epoxy-3, 6-heneicosadiene and (3Z, 6Z, 9S, 10R)-9, 10-epoxy-1, 3, 6-heneicosatriene are obtained through bromination, coupling and hydrogenation. The process is mild and controllable in reaction, good in yield, simple and convenient to operate, few in reaction steps, low in production cost and suitable for large-scale production. The lure prepared from the sex pheromone components synthesized by the synthesis method can effectively trap and kill a large number of hyphantria cunea male moths in combination witha trap, is applied to hyphantria cunea pest situation forecasting and green prevention and control, and can reduce chemical pesticide application, thereby reducing pollution, protecting the environment and remarkably improving economic, social and ecological comprehensive benefits.

Description

technical field [0001] The invention belongs to the technical field of chemical production, and more specifically relates to a method for synthesizing sex pheromone components of the white moth. Background technique [0002] The American white moth Hyphantria cunea (Drury) belongs to the order Lepidoptera and the family Arctiidae, and is an important international quarantine pest. Because it has the characteristics of miscellaneous feeding habits, large food intake, strong reproductive ability, wide adaptability, fast transmission speed, and serious harm, it has become a major invasive alien pest in my country and the most dangerous invasive species at home and abroad. [0003] The American white moth is native to North America, distributed between 19° and 55° north latitude, and then spread to Europe and Asia. Since the first discovery of the American white moth in Dandong City, Liaoning Province in 1979 in China, its epidemic area has spread to 586 county-level administra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/02C07D303/08A01P19/00
CPCC07D303/04C07D301/02C07D303/08C07B2200/09C07B2200/13
Inventor 郝德君赵旭东朱晗
Owner NANJING FORESTRY UNIV
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