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3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone, its preparation method and its application

A technology of pyridyl and pyridone, applied in the field of 3-cyano-5--N-n-propyl-pyridone and its preparation, achieving the effect of great development potential

Inactive Publication Date: 2012-05-09
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] As a new compound, the preparation method and bactericidal activity of 3-cyano-5-(4-pyridyl)-N-n-propyl-pyridone have not been reported in the literature

Method used

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  • 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone, its preparation method and its application
  • 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone, its preparation method and its application
  • 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone, its preparation method and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0022] (1) Synthesis of intermediate 3-cyano-5-(4-pyridyl)-N(1H)pyridone

[0023] Add 31.4g (0.43mol) of DMF to a 100mL three-necked flask, and slowly add 24.76g (0.16mol) of phosphorus oxychloride dropwise while stirring in an ice bath. During the process of dropping phosphorus oxychloride, the reaction is violent and the temperature rises significantly , drop POCl 3 While the temperature was kept at 10°C, POCl 3 After the dropwise addition, keep the temperature at 0-10°C, then slowly drop 5g (0.054mol) 4-methylpyridine into the three-necked flask with a constant pressure titration funnel, and keep reacting for 2 hours, the color will become darker during the reaction process, After the reaction, pour the mixture into ice water, then use 30% NaOH to neutralize the solution to neutrality, filter to remove inorganic salts, and add 9.33g (0.098mol) crushed cyanide to the filtrate at 10-15°C Acetamide, then add 13.3mL of 30% NaOH solution dropwise into the reaction tank and sti...

Embodiment 2

[0027] Dissolve 2 g (0.01 mol) of the intermediate 3-cyano-5-(4-pyridyl)-N(1H) pyridone obtained in Example 1 with 30 mL of DMF and add it to a 100 mL three-necked flask for stirring, then Add 1.34g (0.012mol) of t-BuOK to the reaction tank step by step, stir evenly, then dissolve 1.45g (0.012mol) of n-bromopropane with 20mL of DMF and drop into the reaction three-necked flask, stir at 25°C React for 6 hours. The reaction process is monitored by TCL thin-layer chromatography. After the reaction is completed, the target product is purified by silica gel column chromatography to finally obtain 3-cyano-5-(4-pyridyl)-N-n-propyl-pyridone Obtained 1 g, 45% yield.

Embodiment 3

[0029] Use 10mL of DMF to dissolve 2g (0.01mol) of 3-cyano-5-(4-pyridyl)-N(1H)pyridone in a 100mL three-necked flask and stir, then add 1.34g (0.012mol) of t -BuOK was added to the reaction tank step by step, and after stirring evenly, 1.45g (0.012mol) of n-bromopropane was dissolved in 10mL of DMF and added dropwise to the reaction three-necked flask, and stirred at 20°C for 7 hours. The reaction process is monitored by TCL thin-layer chromatography. After the reaction is completed, the target product is purified by silica gel column chromatography to finally obtain 3-cyano-5-(4-pyridyl)-N-n-propyl-pyridone Obtained 0.9 g, yield 44.0%.

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Abstract

The invention relates to 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone, its preparation method and its application. The 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone has a structural formula shown in the following formula I: I. The invention has the beneficial effect that the compound 3-cyan-5-(4-pyridyl)-N-n-propyl-pyridone possessing bactericidal activity can be used as a green chemical pesticide, and has large development potential.

Description

technical field [0001] The present invention relates to 3-cyano-5-(4-pyridyl)-N-n-propyl-pyridone and its preparation method and application. Background technique [0002] In recent years, various pathogens have caused more and more serious damage to plants. The pathogen of lawn brown spot disease is Rhizoctonia solani ( Rhizoctonia solani Kuhn ), belonging to the genus Rhizoctonia of the subphylum Hyphomycetes and the order Asporoides. The fungus infects a wide range, including forest tree seedlings, vegetables, flowers and crops, and infects almost all turfgrass varieties. Lawn brown spot is an important disease of turfgrass, which occurs in cold and warm season turfgrass worldwide, especially in the United States, Canada, Europe and Japan. According to investigations, the disease incidence rate is generally about 30%, and severe cases can reach more than 50%, which seriously affects the greening of lawns. The State Forestry Administration listed it as a domestic forest...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/85A01N43/40A01P3/00
Inventor 巨修练马静黄龙葛燕丽韩新才
Owner WUHAN INSTITUTE OF TECHNOLOGY