Unlock instant, AI-driven research and patent intelligence for your innovation.

3-(2-furan)-4-hydroxycoumarin compound and its preparation method and application against plant fungus

A technology of hydroxycoumarin and plant fungi, which is applied in the direction of botany equipment and methods, applications, plant growth regulators, etc., can solve the problems of toxicity, pathogenic fungus drug resistance, etc., and achieve short synthesis routes and good plant protection effects , the effect of low production cost

Inactive Publication Date: 2021-07-23
SHAANXI NORMAL UNIV
View PDF0 Cites 0 Cited by
  • 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

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
  • 3-(2-furan)-4-hydroxycoumarin compound and its preparation method and application against plant fungus
  • 3-(2-furan)-4-hydroxycoumarin compound and its preparation method and application against plant fungus
  • 3-(2-furan)-4-hydroxycoumarin compound and its preparation method and application against plant fungus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of compounds 3A ~ 3P

[0024] 0.1040 g (0.5 mmol) of 3- (2-hydroxyphenyl) -3-oxproppropropate was added to the reaction kettle, and 0.1040 g k10 montmorillonite was added, and then 0.0976 g was added. 0.75 mmol) 2,5-dimethoxy-2,5-dihydrofuran, constant temperature stirring reaction 1 h; then 0.04 g (1 mmol) sodium hydroxide, and 1 ml of ethanol, reflux reaction 0.5 h; after the reaction is completed, vacuum Filter recovery K10 montmorillonite, the filtrate is separated from the column chromatography (eluent: CH) 2 CL 2 ), The pure product of Compound 3a is obtained.

[0025] In the present embodiment, an equimolar 3- (2-hydroxy-4-methoxyphenyl) -3-oxypropropate, 3- (2-hydroxy-6-methoxyphenyl) -3 Ethyl proppropionate, 3- (2-hydroxy-3-toluene) -3-oxypropionate, 3- (2-hydroxy-5-toluene) -3-oxpropropate Ester, 3- (2-hydroxy-4,5-dimethoxyphenyl) -3-oxypropropate, 3- (2-hydroxy-4,6-dimethoxy) -3 Ethyl proppropionate, 3- (4-ethoxy-2-hydroxy-3-toluene) -3-oxypropionate,...

Embodiment 2

[0046] In the present embodiment, the amount of K10 montmorillonite and the mass ratio of 3- (2-hydroxyphenyl) -3-oxpropionate compound is 0.5: 1, and other steps and reaction conditions are the same as in Example 1. The compounds 3a to 3p were obtained sequentially, and the product yield was shown in Table 2.

[0047] Form 2 yield of Compound 3A to 3S

[0048] Compound 3A Compound 3B Compound 3C Compound 3D Compound 3E Compound 3F Compound 3g Compound 3h 62％ 58％ 81％ 76％ 80％ 64％ 67％ 75％ Compound 3i Compound 3J Compound 3K Compound 3L Compound 3M Compound 3N Compound 3o Compound 3P 71％ 66％ 54％ 62％ 49％ 60％ 55％ 72％

Embodiment 3

[0050] In this embodiment, the amount of K10 montmorillonite and 3- (2-hydroxyphenyl) -3-oxpropropate compound is 2: 1, and other steps and reaction conditions are the same as in Example 1. The compounds 3a to 3p were obtained in times, and the product yield was shown in Table 3.

[0051] Table 3 yield of compounds 3A to 3S

[0052] Compound 3A Compound 3B Compound 3C Compound 3D Compound 3E Compound 3F Compound 3g Compound 3h 87％ 89％ 93％ 85％ 94％ 90％ 95％ 86％ Compound 3i Compound 3J Compound 3K Compound 3L Compound 3M Compound 3N Compound 3o Compound 3P 68％ 71％ 82％ 78％ 73％ 81％ 81％ 89％

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a class of 3-(2-furan)-4-hydroxycoumarin compounds, a preparation method thereof and an application against plant fungi. The structural formula of the compound is R in the formula 1 , R 2 , R 3 , R 4 Each independently represents any one of H, methyl, methoxy, ethoxy, fluorine, chlorine, bromine, and hydroxyl. After heating 3-(2-hydroxyphenyl)-3-oxopropionate ethyl ester compound, K10 montmorillonite and 2,5-dimethoxy-2,5-dihydrofuran for coupling reaction, Then add sodium hydroxide, reflux in ethanol solution, and then separate and purify to obtain the pure product of the compound of the present invention. The synthetic method of the present invention has no solvent, uses cheap raw materials and K10 montmorillonite catalysis, has the advantages of simple process, simple operation, high product yield and low production cost, and the obtained compound has good anti-plant fungus effect, and can be developed as an anti-fungal Novel pesticides for plant fungi.

Description

Technical field [0001] The present invention belongs to the field of heterocyclic compounds, and more particularly to a class of 3- (2-furan) -4-hydroxyrapanolaen compounds, and the preparation method of the compound and the application in the anti-plant fungi. Background technique [0002] Cathoxin and its derivatives are an extremely important heterocyclic compound, existing in natural plants, animals and microbes or subsequent metabolites. The coumarin and its derivatives have a largest Stokes displacement, and the fluorescence quantum yield is high, and therefore often used as fluorescent whitening agents and fluorescent probes, which is more eye-catching that such compounds can play π -π interaction, hydrogen bond, metal chelation, hydrophobic, electrostatic interaction, and Van Dew Huawhuo interactions, anti-bacterial, antifungal, anti-inflammatory, anti-cancer, antihypertensive, anti-HIV, Antioxidant, anti-tuberculosis, hepatitis, anti-malaria, anti-coagulation, etc. have ...

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
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04A01N43/16A01P3/00
CPCA01N43/16C07D407/04
Inventor 彭菊芳张尊听张瑾
Owner SHAANXI NORMAL UNIV