Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

7-aryloxyacetyl coumarin compound and application thereof in pesticides

An aryloxyacetoxy, coumarin technology, applied in the application, biocide, organic chemistry and other directions, to achieve the effect of improving herbicidal activity, high herbicidal activity, and high control effect

Inactive Publication Date: 2017-05-31
JIANGSU UNIV
View PDF6 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the research on the activity of 7-hydroxycoumarin mainly includes anti-tumor, anti-oxidation, etc., and there are few reports on the agricultural herbicidal activity.

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
  • 7-aryloxyacetyl coumarin compound and application thereof in pesticides
  • 7-aryloxyacetyl coumarin compound and application thereof in pesticides
  • 7-aryloxyacetyl coumarin compound and application thereof in pesticides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: Preparation of 7-hydroxyl-4,5-dimethylcoumarin (A1):

[0032] The structural formula is:

[0033] 0.62g (5mmol) of 5-methylresorcinol and 8.0mL of concentrated sulfuric acid were stirred to dissolve, and 0.65mL (5mmol) of ethyl acetoacetate was slowly added dropwise under cooling in an ice-water bath; Reaction at room temperature for 24h. Pour into a large amount of ice water under vigorous stirring, a precipitate is formed, filter with suction, and recrystallize the filter cake with absolute ethanol to obtain 0.74g of 7-hydroxy-4,5-dimethylcoumarin (A1) as a white powder. Rate 78.2%, mp: 251~253℃; 1 H NMR (400MHz, DMSO-d 6 )δ:2.28(s,3H,CH 3 ),2.54(s,3H,CH 3 ),5.93~6.11(m,1H,H-6),6.52~6.69(m,1H,H-8),10.53(s,1H,OH); 13 C NMR (400MHz, DMSO-d 6 )δ: 160.3, 156.9, 155.3, 155.0, 143.2, 112.4, 112.3, 108.2, 101.0, 23.9, 21.6. Anal. Calcd for C 11 h 10 o 3 : C 69.46, H 5.30; found C 69.58, H 5.07.

Embodiment 2

[0034] Embodiment 2: Preparation of 7-hydroxyl-4-chloromethyl-5-methylcoumarin (A2):

[0035] The structural formula is:

[0036] 0.62g (5mmol) of 5-methylresorcinol and 8.0mL of concentrated sulfuric acid were stirred to dissolve, and 0.68mL (5mmol) of ethyl 4-chloromethylacetoacetate was slowly added dropwise under cooling in an ice-water bath. Reaction under cooling for 1h; reaction at room temperature for 24h. Pour into a large amount of ice water under vigorous stirring, a precipitate is formed, filter with suction, and recrystallize the filter cake with absolute ethanol to obtain 0.90 g of 7-hydroxy-4-chloromethyl-5-methylcoumarin (A2), white Powder, yield 80.3%, mp: 275~277℃; 1 H NMR (400MHz, DMSO-d 6 )δ:2.29(s,3H,CH 3 ),5.08(s,2H,CH 2 ),6.41(s,1H,H-3),6.55~6.62(m,1H,H-6),6.64~6.70(m,1H,H-8),10.92(s,1H,OH); 13 C NMR (400MHz, DMSO-d 6 )δ: 160.2, 156.1, 155.3, 152.2, 143.9, 112.6, 112.5, 108.4, 104.8, 45.5, 21.6. Anal. Calcd for C 11 h 9 ClO 3 : C58.81, H 4.04...

Embodiment 3

[0037] Embodiment 3: Preparation of 7-hydroxyl-4-trifluoromethyl-5-methylcoumarin (A3):

[0038] The structural formula is:

[0039] 0.62g (5mmol) of 5-methylresorcinol and 8.0mL of concentrated sulfuric acid were stirred to dissolve, and 0.73mL (5mmol) of ethyl 4,4,4-trifluoroacetoacetate was slowly added dropwise under cooling in an ice-water bath. , Reacted for 1h under cooling in an ice-water bath; reacted for 24h at room temperature. Poured into a large amount of ice water under vigorous stirring, a precipitate formed, suction filtered, and the filter cake was recrystallized with absolute ethanol to obtain 0.95 g of 7-hydroxy-4-trifluoromethyl-5-methylcoumarin (A3). White powder, yield 77.9%, mp: 255~256℃; 1 H NMR (400MHz, DMSO-d 6 )δ:2.51(s,3H,CH 3), 4.16(s, 1H, OH), 6.64~6.71(m, 1H, H-3), 6.73~6.81(m, 2H, H-6, H-8); 13 C NMR (400MHz, DMSO-d 6 )δ: 161.3, 158.9, 158.0, 145.1, 137.3, 118.6, 113.0, 105.8, 102.4, 22.3, 21.6. Anal. Calcd for C 11 h 7 f 3 o 3 : C 5...

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

No PUM Login to View More

Abstract

The invention provides a 7-aryloxyacetyl coumarin compound and application thereof in pesticides. The preparation method comprises the following steps: 1, adding resorcinol containing different substituent groups into a reaction bottle filled with concentrated sulfuric acid, stirring and dissolving, slowly dripping an acetylacetate compound under ice-water bath cooling, and reacting under the ice-water bath cooling for an hour after dripping is completed; reacting at room temperature for 24 hours; pouring into an ice-water mixture while agitating intensely, producing a yellow precipitate, performing suction filtration, and recrystallizing the filter cake by using absolute ethyl alcohol so as to obtain a 7-hydroxycoumarin compound; dissolving 2,2,4-dichlorphenoxyacetic acid and oxalyl chloride in a CH2Cl2 solvent, dripping N,N-dimethylformamide, reacting at room temperature for 2 hours so as to obtain acyl chloride; and 3, adding a catalyst into an organic solvent containing the 7-hydroxycoumarin compound and acyl chloride at a certain temperature, and recrystallizing after reacting for a period of time, thereby obtaining the 7-aryloxyacetyl coumarin compound. The compound disclosed by the invention has extremely high herbicidal activity.

Description

technical field [0001] The invention relates to 7-aryloxyacetoxy coumarin compounds and their application in pesticides, belonging to the technical field of herbicides. Background technique [0002] With the enhancement of people's awareness of environmental protection, the research and development of new varieties of pesticides with high efficiency, low toxicity, low residue and environmental friendliness is not only the key to ensuring the healthy and sustainable development of modern agricultural production, but also the key to ensuring the safety of the ecological environment, the quality and safety of agricultural products and agricultural An important aspect of trade security. Taking natural products as lead compounds, modifying and optimizing their structures, designing, synthesizing and screening highly active compounds are effective means to discover new, safe and highly effective pesticides. [0003] Coumarin was first extracted from the leguminous plant Coumadin,...

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 Applications(China)
IPC IPC(8): C07D311/18A01N43/16A01P13/00
CPCA01N43/16C07D311/18
Inventor 刘莉张敏杨乐夏梅钱敏仰榴青
Owner JIANGSU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com