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Synthesis and application of lactone analogue with flavone framework

A technology of analogs and skeletons, applied in the field of Striga, can solve the problems of complex structure, difficult to synthesize in large quantities, etc.

Active Publication Date: 2019-12-27
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the complex structure of natural strigolactone compounds is difficult to be synthesized in large quantities and applied in agricultural production. Therefore, simplifying its structure and synthesizing a series of analogues with equivalent activity and simple structure has become a research hotspot at present.

Method used

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  • Synthesis and application of lactone analogue with flavone framework
  • Synthesis and application of lactone analogue with flavone framework
  • Synthesis and application of lactone analogue with flavone framework

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthetic route 1:

[0022] 1.36ml of o-hydroxyacetophenone (1.2eq), 0.96ml of benzaldehyde (1eq), 1.29ml of aniline (1.5eq) were dissolved in 15ml of methanol, then 0.72g of iodine was added and the reaction was stirred at 40°C for 20 hours. The reaction process was monitored by TLC. After the substrate was completely consumed, the reaction system was concentrated and directly separated by silica gel column chromatography (petroleum ether: ethyl acetate = 200:1) to obtain 1.3 g of white solid 1 with a yield of 61.5%.

[0023] Take 0.68g of compound 1 (1eq) and dissolve it in 10ml of toluene, then add 1.21ml of N,N-dimethylformamide dimethyl acetal (3eq) to the reaction system, reflux at 150°C for 6-8 hours and TLC monitoring, after the reaction was completed, it was directly separated by silica gel column chromatography (petroleum ether: ethyl acetate = 2:1) to obtain 0.68 g of light yellow solid 2 with a yield of 80.4%.

[0024] Dissolve 0.68g of compound 2 (1eq) in ...

Embodiment 2

[0045] Compounds W-1~W-24 were tested for the germination activity of melon radang and sunflower radang seeds, and the test method was as follows:

[0046] Take a plastic Petri dish with a diameter of 9 cm, lay a piece of filter paper on the bottom layer and moisten it with sterilized distilled water, and then cover it with a filter paper sheet with a diameter of 6 mm. Sprinkle the melon seeds evenly on the wet filter paper, and the number of seeds on the filter paper is about 25-65. Seal the Petri dish with sealant and pre-incubate the seeds for 3-7 days at room temperature in the dark. Take a glass fiber filter paper sheet with a diameter of 6 mm, place it in a plastic petri dish and add 25 μL of the compound solution to be tested (acetone as a solvent), after the acetone is completely volatilized, take a pre-cultured seed piece and place it on top of it, and add 25 μL of sterilized distilled water , and finally place a piece of filter paper moistened with sterilized distil...

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Abstract

The invention relates to synthesis and application of a lactone analogue with a flavone framework. The structural general formula of the compound is (I), wherein R1 or R2 represents a hydrogen atom, C1-C5 alkyl, phenyl, halogen-substituted phenyl, benzodioxole, furan, thiophene and other aromatic heterocycles. According to the method, o-hydroxyacetophenone and aldehyde or ketone are used as raw materials, and a series of lactone analogues with flavone parent nucleus structures are synthesized through multi-step reaction. The broomrape seed germination activity of the compound is tested, wherein the result shows that the compound has good seed germination activity, is a parasitic weed seed germination agent with a wide application prospect, can be practically applied to parasitic weed herbicides, and especially can be applied to prevention and control of parasitic weeds broomrape and striga asiatica in agriculture.

Description

technical field [0001] The present invention relates to the synthesis and application of a lactone analog with a flavone skeleton, in particular to the synthesis and application of a lactone analog with a flavone mother nucleus structure and its application in agriculture to control and eliminate parasitic weeds Lidang and Striga gold applications. Background technique [0002] Strigolactones are a new class of plant hormones discovered after auxin, cytokinin, gibberellin, abscisic acid and ethylene. This type of plant hormone plays an important role in regulating the growth and development of plants. Because of its important physiological role, the research on strigolactone compounds has also received more and more attention. [0003] The first strigolactone compound (+)-strigol ((+)-strigol) was isolated from cotton root exudates in 1966, but due to its complex structure, after two decades It took time for its chemical structure to be fully elucidated. Since then a seri...

Claims

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Application Information

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IPC IPC(8): C07D407/12A01N43/16A01P13/02
CPCC07D407/12A01N43/16
Inventor 徐效华金钟康允尧谢龙观
Owner NANKAI UNIV
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