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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
【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).
【Key words】 hydronopyl; imidazole; quaternary ammonium salt; synthesis; antifungal activity;
- 【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