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Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof

A technology for oxadiazole compounds, which is applied in the field of synthesis of oxadiazole compounds, can solve problems such as undetected and unretrieved, and achieve the effects of high reaction yield, high purity, and high application prospects

Inactive Publication Date: 2014-12-03
天津普茂企业孵化器有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, 1-(4-((5-((4-(1H-1,2,4-triazol-1-yl)phenoxy)methyl)-1,3,4- Oxadiazol-2-yl) methoxy) phenyl) -1H-1,2,4-triazole compound, not to mention 1-(4-((5-((4-(1H -1,2,4-Triazol-1-yl)phenoxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)-1H-1,2 , 4-triazole compounds reported in the literature

Method used

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  • Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof
  • Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof
  • Bitriazole phenyl-substituted oxadiazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of 2,5-bis((4-bromophenoxy)methyl)-1,3,4-oxadiazole:

[0031] In a 50 mL three-neck flask equipped with a magneton and a reflux condenser, add 4-bromophenoxyacetic acid (4.62 g, 20 mmol), 4-bromophenoxyacetylhydrazide (4.90 g, 20 mmol), 20 mL POCl 3, refluxed for 24 hours under the protection of nitrogen, after the reaction was completed, the reaction was lowered to room temperature, poured into ice water, a large amount of precipitate was precipitated, filtered with suction, the filter cake was collected, and recrystallized with water to obtain 2,5-bis((4-bromo Phenoxy)methyl)-1,3,4-oxadiazole, the yield was 89%.

Embodiment 2

[0033] The molar ratio of 2,5-bis((4-bromophenoxy)methyl)-1,3,4-oxadiazole: 1,2,4-triazole: potassium carbonate: cuprous oxide is 2: 10:30:1

[0034] In a 50 mL three-necked round-bottomed flask equipped with a magnet, reflux condenser and thermometer, Cu 2 O (0.0715 mg, 0.5 mmol), potassium carbonate (2.0731 g, 15 mmol), 1,2,4-triazole (0.345 g, 5 mmol), 2,5-bis((4-bromophenoxy) Methyl)-1,3,4-oxadiazole (0.4401 g, 1 mmol), 20 mL DMF. Start stirring at 100°C and react for 24 hours. After the reaction, the reaction solution was lowered to room temperature, filtered, and 100 mL of water was added to the filtrate, a large amount of precipitate was precipitated, filtered with suction, and the filter cake was collected, with a yield of 63%.

[0035] Preparation:

[0036] The molar ratio of 2,5-bis((4-bromophenoxy)methyl)-1,3,4-oxadiazole: 1,2,4-triazole: potassium carbonate: cuprous oxide is 2: 10:30:1

[0037] In a 50 mL three-necked round-bottomed flask equipped with a mag...

Embodiment 3

[0039] The method used as a fungicide is as follows:

[0040] There are two main methods for determining the inhibitory activity of fungicides against fungi: the growth rate method and the spore germination method. The present invention has selected the growth rate method (Sun Jialong, Mu Wei, 2009) i.e. the culture medium dosing method, by mixing the test agent with the unsolidified medium and then connecting the strains, cultivating the pathogenic bacteria with the drug-containing medium, The bactericidal activity of the test agent was judged by the growth rate of the pathogenic bacteria (diameter of the colony). In this paper, the fungicidal activity of target compounds against Botrytis cinerea and Sclerotinia wheat was determined, and carbendazim was used as control.

[0041] compound Virulence regression equation correlation coefficient EC 50 (95% confidence limit) (μg / mL) Compound III Y=3.9747+1.2671X 0.9479 6.44(5.00–8.30) Carbendazim Y...

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Abstract

The invention discloses a bitriazole phenyl-substituted oxadiazole compound and a preparation method and an application thereof. The organic compound is prepared by adopting a one-pot process which comprises the following step of heating 2, 4-di((4-bromophenoxy) methyl)-1, 3, 4-oxadiazole, 1, 2, 4-triazole, potassium carbonate and cuprous oxide. The preparation method disclosed by the invention has the characteristics of simple process operation, low production cost and small environmental pollution and is suitable for large-scale industrial production. The compound prepared by the preparation method disclosed by the invention can be applied to the technical fields of medicines, pesticides, corrosion inhibitors and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis of bistriazole-substituted oxadiazole compounds. More specifically 1-(4-((5-((4-(1H-1,2,4-triazol-1-yl)phenoxy)methyl)-1,3,4-oxa Oxadiazol-2-yl)methoxy)phenyl)-1H-1,2,4-triazole compound and its preparation method and application. Background technique [0002] 1,3,4Oxadiazoles and their derivatives are a class of important physiologically active substances. They are widely used in medicine and agriculture for anti-inflammatory, antibacterial, anesthesia, pain relief, insecticide and regulation of plant growth. Moreover, some substituted oxadiazoles are good fluorescent and scintillating agents. The complexes and polymers formed by oxadiazole compounds have special stability properties, some are also fluorescent, have good film-forming properties, and have good electron transport properties, which can be made into organic electroluminescent materials with g...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/824A01P3/00A01P7/00A01P21/00A61P29/00A61P31/00A61P23/00C23F11/14
CPCC07D413/14A01N43/82C23F11/149
Inventor 刘巨艳赵聪颖杨莉
Owner 天津普茂企业孵化器有限公司
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