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含氢化诺卜基的咪唑型季铵盐的合成及抗菌活性

Synthesis and Antifungal Activity of Imidazole Quaternary Ammonium Salts Containing Hydronopyl

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【作者】 罗颖丁清颖肖转泉罗海王宗德陈尚钘

【Author】 LUO Ying;DING Qingying;XIAO Zhuanquan;LUO Hai;WANG Zongde;CHEN Shangxing;College of Forestry, Jiangxi Agricultural University;East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration;Jiangxi Provincial Key Laboratory of Improved Variety Breeding and Efficient Utilization of Native Tree Species;College of Chemistry and Materials, Jiangxi Normal University;

【通讯作者】 罗海;

【机构】 江西农业大学林学院国家林业草原木本香料(华东)工程技术研究中心江西乡土树种良种选育与高效利用江西省重点实验室江西师范大学化学与材料学院

【摘要】 先将咪唑与氢化诺卜基溴(1)反应合成N-氢化诺卜基咪唑(2),再分别和α-溴代苯乙酮类化合物、α-溴(氯)乙酸乙酯、溴乙醇、氯甲基乙基醚等反应合成了10个含氧基团的氢化诺卜基咪唑季铵盐。分别通过核磁共振(1H NMR和13C NMR)、红外(IR)和质谱(HRMS)分析方法表征了这10个氢化诺卜基咪唑季铵盐的结构,并用菌丝生长速率法测定了其对西瓜枯萎病菌、水稻纹枯病菌、松枯梢病菌和枇杷炭疽病菌等4种植物病原真菌生长的抑制活性。测试结果表明:这些季铵盐对前3种病菌有较好的抑制作用,苯环对位有溴、氯、氟原子的α-溴代苯乙酮和氢化诺卜基咪唑反应合成得到的季铵盐,其抑制活性比没有这几种取代基的季铵盐更好。其中,苯环对位有溴或氯的季铵盐化合物(5b、5d)对西瓜枯萎病菌的半数抑制浓度(IC50)小于5 mg/L、对松枯梢病菌的IC50为10.0 mg/L左右,都远远低于常用杀菌剂三环唑的IC50值(81.9 mg/L和225.5 mg/L)。

【Abstract】 N-hydronopyl imidazole(2) was synthesized by the reaction of imidazole with hydronobylbromide(1), and then 10 hydronopyl imidazoles quaternary ammonium salts containing oxygen groups were synthesized by reacting with α-bromoacetophenone, α-bromo(chloro) ethyl acetate, bromoethanol and chloromethylethyl ether, respectively. The structures of the 10 hydronopyl imidazoles quaternary ammonium salts were characterized by 1H NMR, 13C NMR, IR and HRMS analysis methods. The mycelial growth rate method was utilized to measure the inhibitory activities of these compounds against four kinds of plant pathogens, named Fusarium oxyporum f. sp. niveum, Rhizoctonia solani, Sphaeropsis sapinea, and Colletotrichum acutatum. The results showed that these quaternary ammonium salts had better inhibitory effect on the first three species of bacteria, and the quaternary ammonium salts synthesized by the reaction of α-bromoacetophenone with bromine, chlorine and fluorine atoms on para-position of benzene ring and hydronopyl imidazoles had better inhibitory activity than those without these substitutions. Among them, the half inhibitory concentration(IC50) of the quaternary ammonium compounds(5b, 5d) with benzene ring para-bromine or para-chlorine was less than 5 mg/L against F. oxyporum f. sp. niveum, and the IC50 of S. sapinea was about 10.0 mg/L, which was much lower than that of the commonly used fungicide tricyclazole(81.9 mg/L and 225.5 mg/L).

【基金】 国家自然科学基金资助项目(32360365);西南林业大学西南地区林业生物质资源高效利用国家林业和草原局重点实验室开放课题研究基金(2022-KF12);江西省林业局林业科技创新项目(创新专项(2023)16号)
  • 【文献出处】 生物质化学工程 ,Biomass Chemical Engineering , 编辑部邮箱 ,2024年06期
  • 【分类号】TQ455
  • 【下载频次】18
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