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3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus

A technology of hydroxycoumarin and compounds, which is applied in the field of 3--4-hydroxycoumarin compounds, can solve the problems of toxicity and pathogenic fungus drug resistance, and achieve short synthesis routes, good plant protection effects, and low production costs low effect

Inactive Publication Date: 2019-01-04
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the abuse or long-term use of some pesticides, many pathogenic fungi are resistant to them, and even some pesticides themselves have certain toxicity to the human body, so there is an urgent need for new, safer and more efficient fungicides to replace

Method used

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  • 3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus
  • 3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus
  • 3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of Compounds 3a-3p

[0024] Add 0.1040g (0.5mmol) ethyl 3-(2-hydroxyphenyl)-3-oxopropionate to the reaction kettle, add 0.1040g K10 montmorillonite under stirring, heat to 80°C, then add 0.0976g ( 0.75mmol) 2,5-dimethoxy-2,5-dihydrofuran, stirred at constant temperature for 1h; then added 0.04g (1mmol) sodium hydroxide, and added 1mL ethanol, refluxed for 0.5h; vacuum K10 montmorillonite was recovered by filtration, and the filtrate was distilled under reduced pressure and purified by column chromatography (eluent: CH 2 Cl 2 ), to obtain the pure product of compound 3a.

[0025] In this example, equimolar 3-(2-hydroxyl-4-methoxyphenyl)-3-oxopropionic acid ethyl ester, 3-(2-hydroxyl-6-methoxyphenyl)-3 -Ethyl oxopropionate, ethyl 3-(2-hydroxy-3-methylphenyl)-3-oxopropionate, ethyl 3-(2-hydroxy-5-methylphenyl)-3-oxopropionate Esters, ethyl 3-(2-hydroxy-4,5-dimethoxyphenyl)-3-oxopropionate, 3-(2-hydroxy-4,6-dimethoxyphenyl)-3 -Ethyl oxopropionate, ethyl 3-(...

Embodiment 2

[0046] In this example, the mass ratio of the amount of K10 montmorillonite to 3-(2-hydroxyphenyl)-3-oxopropionic acid ethyl ester compound is 0.5:1, and other steps and reaction conditions are the same as in Example 1 , Compounds 3a-3p were sequentially obtained, and the product yields are shown in Table 2.

[0047] The productive rate of table 2 compound 3a~3s

[0048] Compound 3a

Embodiment 3

[0050] In this example, the mass ratio of the amount of K10 montmorillonite to 3-(2-hydroxyphenyl)-3-oxopropionic acid ethyl ester compound is 2:1, and other steps and reaction conditions are the same as in Example 1 , Compounds 3a-3p were sequentially obtained, and the product yields are shown in Table 3.

[0051] The productive rate of table 3 compound 3a~3s

[0052] Compound 3a

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Abstract

The invention discloses a 3-(2-furan)-4-hydroxycoumarin compound, preparation method thereof and application of anti-plant fungus. The formula is shown in description, wherein R1, R2, R3 and R4 independently represent any of H, methyl, methoxy, ethoxy, fluorine, chlorine and bromine, 3-(2- Hydroxyphenyl)-3-Oxopropanoate ester compounds, K10 montmorillonite and 2.5-Dimethoxy-2.5-dihydrofuran is heated and subjected to coupling reaction, sodium hydroxide is added, and refluxed in ethanol solution, followed by separation and purification, the pure product of the compound is obtained. The synthesis method has the advantages of no solvent, cheap raw materials and K10 montmorillonite catalysis, simple and convenient process, simple operation, high product yield, low production cost and the like,and the obtained compound has good anti-plant fungal effect and can be developed into a novel pesticide with anti-plant fungi.

Description

technical field [0001] The invention belongs to the technical field of heterocyclic compounds, and specifically relates to a class of 3-(2-furan)-4-hydroxycoumarin compounds, a preparation method of the compound and an application in anti-plant fungus. Background technique [0002] Coumarin and its derivatives are an extremely important class of heterocyclic compounds, which widely exist in plants, animals and microorganisms or in secondary metabolites in nature. Coumarin and its derivatives have large Stokes shift and high fluorescence quantum yield, so they are often used as fluorescent whitening agents and fluorescent probes. What is more remarkable is that these compounds can play a π -π interaction, hydrogen bond, metal chelation, hydrophobicity, electrostatic interaction and van der Waals force and other non-covalent interactions, in antibacterial, antifungal, anti-inflammatory, anticancer, antihypertensive, anti-HIV, It has broad application prospects in anti-oxidati...

Claims

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Application Information

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IPC IPC(8): C07D407/04A01N43/16A01P3/00
CPCA01N43/16C07D407/04
Inventor 彭菊芳张尊听张瑾
Owner SHAANXI NORMAL UNIV
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