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1,3,4-oxadiazole sulfur/oxygen ether compound with amide bonds, preparation method of compound and application

A technology of oxadiazole sulfur compounds, which is applied in the field of 1,3,4-oxadiazole sulfur/oxyether compounds and their preparation, can solve the problems of difficult prevention and control, wide range of damage, and low antiviral efficacy

Active Publication Date: 2017-08-11
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In recent years, with the continuous change of ecological conditions, varieties and farming systems, plant bacterial diseases (such as rice bacterial blight and citrus canker, etc.) and viral diseases (such as tobacco mosaic disease, etc.) It is popular and has a tendency to further spread throughout the country. It has a wide range of damage and is difficult to control. Existing commercialized antibacterial agents (such as eclopyrazole, thibacterium copper, and ketone) and antiviral agents (Ningnanmycin, virus azoles, etc.) have low control effects, and it is urgent to find active compounds that are highly effective against plant disease bacteria or viruses. On this basis, new green pesticides with independent intellectual property rights are created to provide candidate drugs for the prevention and control of bacterial and viral diseases of crops

Method used

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  • 1,3,4-oxadiazole sulfur/oxygen ether compound with amide bonds, preparation method of compound and application
  • 1,3,4-oxadiazole sulfur/oxygen ether compound with amide bonds, preparation method of compound and application
  • 1,3,4-oxadiazole sulfur/oxygen ether compound with amide bonds, preparation method of compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1 of the present invention: Preparation of target compound 2-nitro-N-(2-methyl-5-(mercapto)-1,3,4-oxadiazole)benzamide

[0022] Add N-(2-acetylhydrazino)-2-nitrobenzamide (5.0mmol) into 50mL ethanol solution dissolved in KOH (10mmol), slowly add carbon disulfide (10.0mmol) dropwise, and react at room temperature for 12 hours Change to heating and reflux for 12 hours, stop the reaction, remove the solvent, add 30 mL of water, and adjust the pH to 3-4 with concentrated hydrochloric acid to obtain a yellow solid with a yield of 54.2% and a melting point of >230°C.

Embodiment 2

[0023] Example 2 of the present invention: Preparation of target compound 2-nitro-N-(2-methyl-5-(methylsulfide)-1,3,4-oxadiazole)benzamide

[0024] Add 2-nitro-N-(2-methyl-5-(mercapto)-1,3,4-oxadiazole)benzamide (2.0mmol) into NaOH solution, add dimethyl sulfate dropwise The ester (2.0 mmol) was reacted at room temperature for 12 hours, then the reaction was stopped, and the reaction was suction filtered to obtain a yellow solid with a yield of 31.4% and a melting point of 108-109°C.

[0025] The synthesis of other target compounds refers to Example 1 or 2.

[0026] The structure, H NMR spectrum and carbon spectrum data of the synthesized 1,3,4-oxadiazole sulfur / oxygen ether compounds containing some amide bonds are shown in Table 1, and their physical and chemical properties are shown in Table 2.

[0027] H NMR spectrum and carbon spectrum data of some compounds in Table 1

[0028]

[0029]

[0030] Table 2 Physicochemical properties of some target compounds

[0031] ...

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Abstract

The invention discloses a 1,3,4-oxadiazole sulfur / oxygen ether compound with amide bonds, a preparation method of the compound and an application. The structure of the compound is as shown in a general formula (I). The compound is based on sulfur ether compounds with 1,3,4-oxadiazole groups, the amide bonds possibly improving biological activities of target compounds are introduced into a system to synthesize a series of 1,3,4-oxadiazole sulfur / oxygen ether compounds with the amide bonds, the compound has good inhibiting effects on pathogenic bacteria and plant viruses, the pathogenic bacteria include rice bacterial leaf blight, candidatus liberibacter asiaticus and the like, the plant viruses include tobacco mosaic virus and the like, and the bisamide compound provides important scientific foundations for research, development and creation of novel pesticides.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a 1,3,4-oxadiazole sulfur / oxygen ether compound containing an amide bond, a preparation method and application thereof. Background technique [0002] In recent years, with the continuous change of ecological conditions, varieties and farming systems, plant bacterial diseases (such as rice bacterial blight and citrus canker, etc.) and viral diseases (such as tobacco mosaic disease, etc.) It is popular and has a tendency to further spread throughout the country. It has a wide range of damage and is difficult to control. Existing commercialized antibacterial agents (such as eclopyrazole, thibacterium copper, and ketone) and antiviral agents (Ningnanmycin, virus azoles, etc.) have low control effects, and it is urgent to discover active compounds that are highly effective against plant disease bacteria or viruses. On this basis, new green pesticides with independent intel...

Claims

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Application Information

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IPC IPC(8): C07D271/113A01N43/824A01P1/00
Inventor 王培义杨松邵武斌周健薛海涛薛伟
Owner GUIZHOU UNIV
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