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1,3,4-oxadiazole (thiadiazole) imidazole compound as well as preparation method and use thereof

A compound, imidazole technology, applied in the field of imidazole compounds and their preparation, can solve the problem of insufficient activity and efficiency

Active Publication Date: 2019-03-29
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the activity of the currently used commercial antibacterial drugs is not efficient enough. Screening and searching for highly effective bactericidal active compounds is an important part of the current development of new pesticides.

Method used

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  • 1,3,4-oxadiazole (thiadiazole) imidazole compound as well as preparation method and use thereof
  • 1,3,4-oxadiazole (thiadiazole) imidazole compound as well as preparation method and use thereof
  • 1,3,4-oxadiazole (thiadiazole) imidazole compound as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082]Example 1: Preparation of intermediate 2-((4-bromobutyl)thio)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole

[0083] Dissolve 1g (4.05mmol) of 5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thiol and 1.4g (10.13mmol) of potassium carbonate in 20mL of DMF, and stir for 20min. Weigh 1.75g ​​(8.1mmol) of 1,4-dibromobutane in the above-mentioned reaction flask, react at room temperature for 2 hours, stop the reaction, extract with ethyl acetate, wash with saturated ammonium chloride, dry, remove the solvent, and perform column chromatography to obtain 1.3 g pale yellow liquid, yield 86.7%.

[0084] With the steps similar to Example 1, intermediates such as halogenated thiadiazole sulfides, halogenated oxadiazole oxyethers, and halogenated oxadiazole sulfides were prepared using corresponding raw materials.

Embodiment 2

[0085] Example 2: Target compound 2-((4-(1H-imidazol-1-yl)butyl)thio)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole preparation of

[0086] Dissolve 29mg (1.21mmol) of sodium hydride and 65mg (0.88mmol) of imidazole in 4mL of anhydrous DMF, stir for 15min, weigh 0.3g (0.79mmol) of 2-((4-bromobutyl)thio)-5- (2,4-dichlorophenyl)-1,3,4-oxadiazole was placed in the above reaction flask, reacted at room temperature for 8 hours, and then stopped the reaction, extracted with ethyl acetate, washed with saturated ammonium chloride, dried, precipitated, and column layer Analysis gave 0.21 g of light yellow solid with a yield of 71.7% and a melting point of 61-63°C.

[0087] The target compounds such as thiadiazole sulfide, oxadiazole oxyether, pyrazole, pyridine, piperidine, morpholine, triazole, diethylamine, etc. were prepared by the similar steps of Example 2 using corresponding raw materials.

Embodiment 3

[0088] Example 3: Target compound 1-(6-((5-(2,4-dichlorophenyl)-1,3,4-oxadiazol-2-yl)thio)hexyl)-3-methyl - Preparation of 1H-imidazole-3-iodide

[0089] 0.17g (0.43mmol) 2-((6-(1H-imidazol-1-yl)hexyl)thio)-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole and 0.18g (1.29mmol) of methyl iodide were dissolved in 4mL of acetonitrile, reacted at 70°C for 12h, then stopped the reaction, precipitation, and column chromatography gave 0.19g of yellow liquid with a yield of 83.7%.

[0090] The other target compounds were prepared by using the corresponding raw materials in the similar steps of Example 3.

[0091] The structure, H NMR spectrum and carbon spectrum data of the 1,3,4-oxa(thia)diazolyl pyridinium salt compound are shown in Table 1, and the physicochemical properties are shown in Table 2.

[0092] Table 1 H NMR spectrum, carbon spectrum and fluorine spectrum data of some compounds

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[0100]

[01...

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Abstract

The invention relates to a 1,3,4-oxadiazole (thiadiazole) imidazole compound as well as a preparation method and use thereof. The compound has a structure shown as a general formula (I) in the description. The compound has good inhibition effects on plant pathogenic bacteria, such as xanthomonas oryzae pv. oryzae and xanthomonas citri.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an imidazole compound containing 1,3,4-oxa(thia)diazolyl and its preparation method and application. Background technique [0002] In recent years, plant pathogenic bacteria have seriously threatened the production of food and crops in my country. In order to control bacterial diseases, it is urgent to prepare active small molecules that are highly effective against pathogenic bacteria. However, the activity of the currently used commercial antibacterial drugs is not efficient enough. Screening and searching for highly effective bactericidal active compounds is an important part of the current research and development of new pesticides. Compounds based on imidazoles (salts) have become one of the hotspots of research scholars because of their wide range of biological activities (such as anti-Gram-positive (or negative) bacteria, etc.). At the same time, thioether com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12C07D413/14C07D417/12C07D403/12C07D271/113A01N43/824A01N43/84A01N43/653A01P1/00A01P3/00
CPCA01N43/653A01N43/82A01N43/84C07D271/113C07D403/12C07D413/12C07D413/14C07D417/12
Inventor 杨松王明伟解娇郑秀李列翔唐丁依罗彬王培义
Owner GUIZHOU UNIV
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