(Trans) beta-farnesene analogue containing jasmonic acid base group, as well as preparation and application of (trans)-beta-farnesene analogue

A technology of jasmonic acid and farnesene, which is applied in the fields of application, pest control, and pest repellent, can solve the problems of limited application, poor stability, and easy volatility, and achieve easy product purification, improved stability, and low cost Effect

Active Publication Date: 2016-11-16
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the existence of multiple double bonds in the EBF structure, it is volatile, easy to oxidize, and has poor stability, which limits its application in the field. Therefore, it is necessary to modify the EBF structure

Method used

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  • (Trans) beta-farnesene analogue containing jasmonic acid base group, as well as preparation and application of (trans)-beta-farnesene analogue
  • (Trans) beta-farnesene analogue containing jasmonic acid base group, as well as preparation and application of (trans)-beta-farnesene analogue
  • (Trans) beta-farnesene analogue containing jasmonic acid base group, as well as preparation and application of (trans)-beta-farnesene analogue

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of (trans)-β-farnesene analogs containing jasmonic acid groups

[0031] Add 448mg (2mmol) methyl jasmonate (compound shown in formula III) in the mixed solution of 5mL water and 5mL THF, the mixture obtained is added to 168mg (4mmol) LiOH.H 2 O, stirred at room temperature for 1 h, then diluted with 30 mL of water; the aqueous layer was washed successively with 30 mL of hexane, acidified with 1 mol / L hydrochloric acid, and extracted with ethyl acetate; 4 After drying, the solvent was evaporated to give a yellow oily liquid.

[0032] Dissolve the yellow oily liquid into 10mL THF, then add 585mg (3.8mmol) geraniol, DMAP (23mg, 0.2mmol) and DCC (582mg, 2.8mmol) in 5mL THF successively, stir at room temperature for 1.5h, then Diluted with chloroform, filtered off the white solid; the organic phase was washed with 1mol / L hydrochloric acid and acetic acid solution, and then washed with MgSO 4 Drying, evaporation of solvent; Finally, the product obtain...

Embodiment 2

[0055] Example 2: Repellent activity of (trans)-β-farnesene analogues containing jasmonic acid groups against aphids

[0056] More than 20 wingless adult green peach aphids were released from the release port, and humid air passed through activated carbon and distilled water was introduced into each arm through an air pump at 0.2 L / min. The humid air introduced into the test arm passed through 5 μg of the flavor source of (trans)-β-farnesene analogue containing jasmonic acid groups, and the other arm was used as a control arm, and the humid air introduced passed through the solvent. Record the number of aphids in each arm when the sample was introduced for 15 minutes. For each repetition, the olfactometer and leather tube were cleaned with absolute ethanol, the filter paper was replaced, and the two arms were used interchangeably. Each sample experiment was repeated three times. The aphids that crossed the center of the olfactometer by 2cm were included in the treatment group...

Embodiment 3

[0064] Example 3: Aphidicidal activity of (trans)-β-farnesene analogues containing jasmonic acid groups against aphids

[0065] Weigh 50mg of (trans)-beta-farnesene analogs containing jasmonic acid groups in a 20ml weighing bottle with a ten-thousandth balance, and import it into a 10mL volumetric flask to form a 5000mg / L mother liquor; Take 1mL of the mother liquor in a weighing bottle, add 9ml of an aqueous solution containing 0.1% Triton X-100, and mix well to obtain a 500mg / L assay solution. Soybean leaves cultivated indoors that have not been exposed to any pesticides and insects are used to punch out leaves of suitable size with a 15mm diameter puncher, immersed in the diluted measurement solution for 15 seconds, taken out to dry, and placed in the bioassay plate. With the back facing up, 1% agar was added to the bottom to keep it moist, and 20 soybean aphids were inserted into each well, and each was repeated 3 times. Check the results after 48 hours. The criteria for...

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Abstract

The invention discloses a (trans)-beta-farnesene analogue containing a jasmonic acid base group, as well as preparation and application of the (trans)-beta-farnesene analogue belonging to the field of organic chemistry synthesis. The preparation of the (trans)-beta-farnesene analogue comprises the following steps of adding alkali and a condensing agent to an organic solvent, and in the organic solvent, enabling compounds as shown in a formula III or a formula V to be subjected to a condensation reaction so as to obtain the (trans)-beta-farnesene analogue containing the jasmonic acid base group, as shown in a formula I or a formula II. A synthetic method is simple to operate, raw materials are easy to obtain, harmful by-products are not produced, and the obtained products are stabler than trans-beta-farnesene. The (trans)-beta-farnesene analogue containing the jasmonic acid base group shows multiple bioactivity; the (trans)-beta-farnesene analogue with high dosage has good killing activity on budworms, and the (trans)-beta-farnesene analogue with low dosage has expelling activity on the budworms, so that the (trans)-beta-farnesene analogue has a high application development value.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to a (trans)-beta-farnesene analogue containing a jasmonic acid group and its preparation and application. Background technique [0002] Jasmonic acid compounds are an important class of plant hormones that play an important role in the initiation and activation of plants' own chemical defense systems. Among them, jasmonic acid and methyl jasmonate are very important in the process of plant growth and development, and are signal substances for plants to resist biotic and abiotic stress (Liptáková, L.; Huttová, J.; Mistrík, I.; Tamás, L.J. Plant Phys. 2013, 170, 646.). When plants are stimulated by the outside world (such as pests, weeds, drought and other unfavorable factors), the content of jasmonic acid and methyl jasmonate in the body will increase rapidly, thereby activating the activity of some special enzymes in the plant to produce certain Secondary subs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/738C07C69/716A01N37/42A01P7/04A01P17/00
CPCA01N37/42C07C69/716C07C69/738
Inventor 段红霞杜少卿张景朋秦耀果杨新玲宋敦伦
Owner CHINA AGRI UNIV
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