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(6S)-(-)-6-bromoisolongifolenone and synthetic method and application thereof

A technology of isolongifolenone and its synthesis method, which is applied in the fields of application, chemical instruments and methods, botany equipment and methods, etc., can solve the problems of low control efficiency, complex synthesis route, difficult promotion, etc., and achieve good selective toxicity Killing effect, simple synthesis route, and convenient use

Inactive Publication Date: 2016-05-25
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] There are many methods for the prevention and control of Lagerstroemia aphid, such as horticultural control: combining pruning in winter, removing diseased and insect branches, thin branches and over-dense branches to reduce overwintering aphid eggs. This method is economical and environmentally friendly, but the control efficiency is low; chemical control : Spray 25% thiamethoxam 5000-10000 times, 10% imidacloprid WP 2000 times, or 50% fenitrothion EC 100 times, 40% omethoate EC 1000 times and 80% dichlorvos EC 100 times liquid, etc., this method can effectively kill pests, but dichlorvos will cause phytotoxicity, and it is easy to "burn leaves". Although thiamethoxam is efficient and harmless, its synthesis route is complicated and the cost is high; biological control: protection Using natural enemies such as ladybugs and lacewings, this method is green and environmentally friendly, but it will cause disorder in the biological chain and it is difficult to promote

Method used

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  • (6S)-(-)-6-bromoisolongifolenone and synthetic method and application thereof
  • (6S)-(-)-6-bromoisolongifolenone and synthetic method and application thereof
  • (6S)-(-)-6-bromoisolongifolenone and synthetic method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0020] In a 100mL three-necked flask equipped with a thermometer, a stirrer and a reflux condenser, add 6.54g (0.03mol) of isolongifolenone, 60mL of ethanol and 13.44g (0.06mol) of copper bromide, and heat to reflux temperature for 3 hours From about to iso-longifolenone, the conversion rate reaches over 95% (GC tracking test). After the reaction liquid is cooled to room temperature, add 100mL of ethyl acetate to dilute, use 3×200mL of water to remove the by-product cuprous bromide, wash the organic phase with saturated brine until neutral, wash over anhydrous Na 2 SO 4 After drying, filtering and concentrating, the crude product was obtained as a yellow liquid, which was then recrystallized with 10 mL of methanol to obtain 7.75 g of colorless and transparent crystal (6S)-(-)-6-bromoisolongifolenone with a yield of 87.0%.

[0021] Product characterization: melting point 91.7~92.6℃; (c=1 mg / mL, CHCl 3 ); GC-MS (70eV) m / z (%): 296 (M + ,60),281(7),255(56),240(10),217(48),20...

Embodiment 2

[0024] Take (6S)-(-)-6-bromoisolongifolenone, prepare a high-concentration mother liquor with acetone, and dilute it with 0.1% TritonX-100 aqueous solution to 200mg / L during the preliminary screening test, and use it when measuring the toxicity line Dilute the 0.1% TritonX-100 aqueous solution into the required series of concentration gradients, soak the cabbage leaf discs with a diameter of 5 cm in the above-mentioned medicinal solution for 10 seconds, take them out, and dry them naturally until there is no clear water. Use 0.1% TritonX-100 aqueous solution as the control. Put the dried leaf butterfly into a plastic petri dish with a diameter of 6.5 cm, and insert 10 mid-3rd instar diamondback moth larvae of the same size. Experimental treatments were repeated 3 times. The treated Plutella xylostella were cultured in a constant temperature incubator with a temperature of 25±1°C and a photoperiod of 16h:8h (L:D), and the results were checked 48 hours after inoculation. Durin...

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Abstract

The invention discloses (6S)-(-)-6-bromoisolongifolenone and a synthetic method and an application thereof. The synthetic method comprises the steps: taking isolongifolenone and copper bromide, and carrying out a bromination reaction in a solvent system, to obtain (6S)-(-)-6-bromoisolongifolenone. A natural renewable resource longifolene derivative-isolongifolenone is used as the raw material, and (6S)-(-)-6-bromoisolongifolenone is prepared through the stereoselectivity reaction; the compound has good selective toxic killing effect on tinocallis kahawaluokalani kirkaldy, and when the concentration of the compound is 50 mg / L, the fatality rate of the tinocallis kahawaluokalani kirkaldy is as high as 82.2%. Therefore, the compound as an insecticide has the characteristics of high efficiency, environmental protection, convenient use, simple synthetic route and low cost, is expected to be used as a novel insecticide for use, and has wide application in eliminating the tinocallis kahawaluokalani kirkaldy especially when used as a specific insecticide.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to (6S)-(-)-6-bromoisolongifolenone and its synthesis method and application. Background technique [0002] The crape myrtle aphid, also known as the crape myrtle acanthus, belongs to the order Homoptera, Aphidoidea, and Aphididae. Distributed in Beijing, Shanghai, Jiangsu, Zhejiang, Taiwan and other places in China. Except for crape myrtle, the host has not been reported yet. The damage to crape myrtle occurs every year, often covering the reverse side of young leaves, twisting new shoots, shrinking young leaves, unevenness, affecting the formation of flower buds, shortening inflorescences, or even having no flowers. virus disease. [0003] There are many methods for the prevention and control of Lagerstroemia aphid, such as horticultural control: combining pruning in winter, removing diseased and insect branches, thin branches and over-dense branches to reduce overwinte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/63C07C49/643A01N35/06A01P7/04
CPCA01N35/06C07C45/63C07C49/643
Inventor 杨益琴丁志斌王石发徐徐徐海军杨金来芮坚曹晓琴王芸芸王忠龙杨丽娟张齐孙楠谷文
Owner NANJING FORESTRY UNIV
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