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Hydrogenated nopyl gemini quaternary ammonium salt containing rigid hydrocarbon chain linking group, synthesis method and application thereof, and antibacterial agent

A technology of gemini quaternary ammonium salt and hydrogenated nop base is applied in the field of hydrogenated nop base gemini quaternary ammonium salt and antibacterial agent to achieve the effects of high product yield and purity, easy operation and good inhibitory effect

Inactive Publication Date: 2020-07-10
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Yet there is no such compound and its synthesis method and the report of antibacterial application at present, therefore, urgently need to explore a kind of hydrogenated nobyl gemini quaternary ammonium salt containing rigid carbon-hydrogen chain linking group with antibacterial effect

Method used

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  • Hydrogenated nopyl gemini quaternary ammonium salt containing rigid hydrocarbon chain linking group, synthesis method and application thereof, and antibacterial agent
  • Hydrogenated nopyl gemini quaternary ammonium salt containing rigid hydrocarbon chain linking group, synthesis method and application thereof, and antibacterial agent
  • Hydrogenated nopyl gemini quaternary ammonium salt containing rigid hydrocarbon chain linking group, synthesis method and application thereof, and antibacterial agent

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Embodiment 1

[0024] This embodiment provides a kind of hydronobyl gemini quaternary ammonium salt containing a rigid carbon-hydrogen chain linking group, which is named after 1,4-dibenzyl bis(hydrogenated notyl dimethyl ammonium bromide), the hydrogenation The synthetic method of Nob base gemini quaternary ammonium salt comprises the following steps:

[0025] Take 0.06moL N,N-dimethylhydronobylamine, 0.03moL 1,4-dibenzyl bromide, and 38mL ethyl acetate in a 150mL ground-mouth Erlenmeyer flask, stir and heat on a magnetic heating stirrer Reflux, stop the reaction after 24h, then cool, suction filter, and rinse with cold ethyl acetate for 3 times, the eluate and filtrate are combined and vacuum-dried; after the filtrate is combined, most of the solvent is evaporated, cooled Part of the crystalline product can be obtained again, and after drying, it can be combined with the previous part of the product to obtain a white powdery solid, which is a hydronopyl gemini quaternary ammonium salt. The...

Embodiment 2

[0027] This embodiment provides a kind of quaternary ammonium salt of hydrogenated notyl gemini containing a rigid carbon-hydrogen chain linking group, which is named after 1,4-dibenzyl bis(hydrogenated notyl diethylammonium bromide). The synthetic method of Nob base gemini quaternary ammonium salt comprises the following steps:

[0028] Take 0.06moL N,N-diethylhydronobylamine, 0.03moL 1,4-dibenzyl bromide, and 38mL acetone in a 150mL ground-mouth Erlenmeyer flask, stir on a magnetic heating stirrer and heat to reflux , stop the reaction after 24h, then cool, suction filter, and rinse with cold ethyl acetate for 3 times, the eluate and filtrate are combined and vacuum-dried; after the filtrate is combined, most of the solvent is evaporated by rotation, cooling can Part of the crystalline product was obtained, and after drying, it was combined with the previous part of the product to obtain a white powdery solid, which was a hydrogenated nobyl gemini quaternary ammonium salt. T...

Embodiment 3

[0030] This embodiment provides a kind of hydronobyl gemini quaternary ammonium salt containing rigid carbon-hydrogen chain linking group, which is named after 1,4-dibenzyl bis(hydrogenated notyl di-n-propyl ammonium bromide), the The synthetic method of hydrogenated nob base gemini quaternary ammonium salt may further comprise the steps:

[0031] Take 0.06moL N,N-di-n-propylhydronobylamine, 0.03moL 1,4-dibenzyl bromide, and 38mL chloroform in a 150mL ground-mouth Erlenmeyer flask, stir and heat on a magnetic heating stirrer Reflux, stop the reaction after 24h, then cool, suction filter, and rinse with cold ethyl acetate for 3 times, the eluate and the filtrate are combined and vacuum-dried; Part of the crystalline product was obtained again, and after drying, it was combined with the previous part of the product to obtain a white powdery solid, which was a hydrogenated nobyl gemini quaternary ammonium salt. The yield was 78%, and the m.p. was 194.4 to 196.2°C. NMR,δ H (CDCl...

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Abstract

The method is suitable for the technical field of chemical synthesis and antibiosis, and provides a hydrogenated nopyl gemini quaternary ammonium salt containing a rigid hydrocarbon chain linking group, a synthesis method and application thereof, and an antibacterial agent. The synthesis method of the hydrogenated nopyl gemini quaternary ammonium salt comprises the following steps: carrying out reflux reaction on a tertiary amine compound containing hydrogenated nopyl and a halide in a weak polar solvent to obtain a reaction product; wherein the halide is 1, 4-benzyl dibromide or 1, 4-benzyl dichloride; carrying out cooling crystallization on the reaction product, and then carrying out suction filtration, washing and vacuum drying treatment to obtain the hydrogenated nopyl gemini quaternary ammonium salt. The hydrogenated nopyl gemini quaternary ammonium salt has a good inhibition effect on phytopathogens like rhizoctonia solani, camellia oleifera colletotrichum, gloeosporium eriobotryae speg, sphaeropsis sapinea, fusicoccum aesculi, coriolus versicolor, phytophthora parasitica and fusarium oxyspirum F sp niveum.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and antibacterial, and in particular relates to a hydrogenated nobyl gemini quaternary ammonium salt containing a rigid carbon-hydrogen chain linking group, its synthesis method, its application and an antibacterial agent. Background technique [0002] In the research process of exploring the deep processing and utilization of turpentine β-pinene, it was found that quaternary ammonium salts containing hydrogenated notyl groups, hydrogenated notyl dimethyl alkyl ammonium halides, hydrogenated notyl diethyl alkyl ammonium halides and bis The quaternary ammonium salts of hydrogenated nobyl have a good effect on inhibiting plant pathogenic bacteria. In particular, certain compounds in the quaternary ammonium salts containing hydrogenated nobyl group have better inhibitory effect on plant pathogenic bacteria. However, although these gemini quaternary ammonium salts previously synthesized ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/27C07C209/12A01N33/12A01P3/00
CPCA01N33/12C07C211/27C07C2602/42
Inventor 范国荣冯雪贞肖转泉王宗德陈尚钘廖圣良
Owner JIANGXI AGRICULTURAL UNIVERSITY
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