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

Oxadiazole-containing thioether and sulfone compound, stereoisomer, salt or solvate thereof, preparation method, composition and application

A technology of oxadiazole sulfide and stereoisomer, which is applied in the field of medicinal chemistry and can solve the problems of poor control effect and increased drug resistance of pathogens

Pending Publication Date: 2022-07-22
GUIZHOU UNIV
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the long-term use of traditional fungicides, such as eclozole and thioxadone, not only has poor control effect, but also increases the resistance of pathogens

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
  • Oxadiazole-containing thioether and sulfone compound, stereoisomer, salt or solvate thereof, preparation method, composition and application
  • Oxadiazole-containing thioether and sulfone compound, stereoisomer, salt or solvate thereof, preparation method, composition and application
  • Oxadiazole-containing thioether and sulfone compound, stereoisomer, salt or solvate thereof, preparation method, composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of intermediate methyl pyran 4-carboxylate

[0048] Pyran-4-carboxylic acid (44.0 mmol) and H 2 SO 4 (2.5mL) and CH 3 OH (50 mL) was added to a 100 mL round-bottomed flask, and heated to reflux for 2.5 h at a temperature of 80 °C. End the reaction, vacuum distillation to remove excess CH 3 OH, extracted with ethyl acetate (100 mL), washed with water (2×50 mL), washed with anhydrous Na 2 SO 4 Drying, desolvation, column chromatography (CH 2 Cl 2 :CH 3 OH=30:1, V / V) to obtain a white oil with a yield of 88.8%.

Embodiment 2

[0049] Example 2: Preparation of intermediate pyran 4-formylhydrazide

[0050] In a 25mL single-neck round bottom flask, add methyl pyran-4-carboxylate (14.0mmol), 3mL hydrazine hydrate and 2mL CH 3 OH, react at room temperature for 20h. Vacuum distillation to remove excess CH 3 OH, extracted with ethyl acetate (50 mL), washed with water (2×20 mL), washed with anhydrous Na 2 SO 4 Drying, desolvation, column chromatography (CH 2 Cl 2 :CH 3 OH=30:1, V / V) to obtain a white oil with a yield of 59.7%.

Embodiment 3

[0051] Example 3: Preparation of intermediate 5-(tetrahydro-2H-pyran-4-yl)-1,3,4-oxadiazole-2-thiol

[0052] In a 50 mL three-necked round bottom flask, the intermediate pyran-4-carboxyhydrazide (3.30 mmol) and KOH (6.6 mmol) were added, and dissolved in 30 mL of ethanol. After stirring for 10 min, 8.2 mmol of CS2 was added, and the reaction was carried out at 85 °C for 1 d, then quenched with water (20 mL), followed by CH 2 Cl 2 (50 mL) V / V to give a white solid in 49.2% yield.

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 discloses a compound containing oxadiazole thioether and sulfone, a stereoisomer thereof, a salt thereof or a solvate thereof, a preparation method, a composition and application, the general formula structure of the compound is as follows: tetrahydropyran-4-formic acid is used as a basis, a heterocyclic compound is introduced into the system, a series of compounds containing oxadiazole thioether and sulfone are synthesized, and the compound containing oxadiazole thioether and sulfone can be used for preparing the compound containing oxadiazole thioether and sulfone. The compound has an excellent inhibition effect on plant pathogenic bacteria such as Xanthomonas oryzae pv. Oryzae and Xanthomonas citri pv. Citri.

Description

technical field [0001] The present invention relates to the technical field of medicinal chemistry, in particular to a compound containing oxadiazole sulfide and sulfone, its stereoisomer, its salt or its solvate, its preparation method, composition and use. Background technique [0002] In recent years, plant fungi and bacteria have seriously affected the yield and quality of crops around the world. Plant fungal diseases directly lead to the decline of crop yield and quality, bringing huge economic losses to farmers. For example, rice is one of the most important crops in our country, providing food for more than half of the population. Bacterial blight is one of the most destructive bacterial diseases on rice, and it has a great negative impact on the yield of commercial crops. Among them, the annual losses to agriculture caused by bacterial diseases such as bacterial blight of rice, citrus canker and kiwifruit canker amount to hundreds of millions of dollars. At present...

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
IPC IPC(8): C07D413/04A01N43/824A01P1/00A01P3/00A01G13/00
CPCC07D413/04A01N43/82A01G13/00
Inventor 杨松王方刘洪武吴志兵柳立伟周翔
Owner GUIZHOU 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