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(IC_(50))小于5 mg/L、对松枯梢病菌的IC_(50)为10.0 mg/L左右,都远远低于常用杀菌剂三环唑的IC_(50)值(81.9 mg/L和225.5 mg/L)。
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 withα-bromoacetophenone,α-bromo(chloro)ethyl acetate,bromoethanol and chloromethylethyl ether,respectively.The structures of the 10 hydronopyl imidazoles quaternary ammonium salts were characterized by 1 H NMR,13 C 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 ofα-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(IC_(50))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 IC_(50) 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).
作者
罗颖
丁清颖
肖转泉
罗海
王宗德
陈尚钘
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,Nanchang 330045,China;College of Chemistry and Materials,Jiangxi Normal University,Nanchang 330027,China)
出处
《生物质化学工程》
CAS
2024年第6期44-52,共9页
Biomass Chemical Engineering
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)。
关键词
氢化诺卜基
咪唑
季铵盐
合成
抑菌活性
hydronopyl
imidazole
quaternary ammonium salt
synthesis
antifungal activity
作者简介
罗颖(2001-),女,云南楚雄人,硕士生,主要从事森林植物资源开发与利用研究工作;通讯作者:罗海,助理研究员,博士,研究领域:森林植物资源开发利用,E-mail:njfuhailuo@163.com。
