Synthetic method of hyphantria cunea sex pheromone components
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF5 Cites 5 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
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.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more