含5,5-偕二甲基的丁烯内酯肟醚类化合物的合成及抑菌活性  

Synthesis and antifungal activity of butenolide oxime ether derivatives containing 5,5-gem dimethyl moiety

作　　者：安鑫鲲 赵斌[1] 张倩[1] 张婷婷[1] 崔国恩 马好运 王明安[1] AN Xinkun;ZHAO Bin;ZHANG Qian;ZHANG Tingting;CUI Guoen;MA Haoyun;WANG Mingan(Innovation Center of Pesticide Research,Department of Applied Chemistry,China Agricultural University,Beijing 100193,China)

机构地区：[1]中国农业大学应用化学系农药创新研究中心,北京100193

出　　处：《农药学学报》2023年第6期1270-1278,共9页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(21772229)。

摘　　要：为了发现更高杀抑菌活性的化合物并探讨其构效关系,以5,5-二甲基丁烯内酯为导向结构,设计并合成了一系列未见文献报道的5,5-二甲基丁烯内酯肟醚类化合物,其结构通过核磁共振氢谱(^(1)H NMR)、碳谱(^(13)C NMR)及高分辨质谱(HRMS)确证。离体抑菌活性测试结果表明,在50 mg/L质量浓度下,化合物D13对棉花立枯丝核菌的抑制率为71.2%,D8对油菜菌核病菌的抑制率为69.0%,D11和D24对番茄灰霉病菌的抑制率为71.7%和72.3%。对番茄灰霉病菌而言,含有4-吡啶杂环的化合物D5~D30的抑制活性高于其他4-取代苯环的化合物,说明吡啶环的存在可以提高该类化合物的抑菌活性,这对进一步发现高活性候选化合物具有指导意义。In order to discover compounds with higher antifungal activity and elucidate structureactivity relationship of this class of compounds,a series of butenolide oxime ether derivatives containing 5,5-gem dimethyl moiety were designed and synthesized using 5,5-dimethyl butenolide as the lead structure.Their structures were characterized by ^(1)H NMR,^(13)C NMR and HRMS.The in vitro antifungal activity evaluation revealed that the inhibition rates of compound D13 against Rhizoctonia solani,D8 against Sclerotinia sclerotiorum,D11 and D24 against Botrytis cinerea were 71.2%,69.0%,71.7%and 72.3%at the concentration of 50 mg/L,respectively.As for B.cinerea,the inhibition rates of compounds D5-D30 with 4-pyridine moiety were much higher than those of compounds with substituted benzene at 4-position of butenolide,indicating the pyridine group can improve antifungal activities.These results provide insights into the structure-activity relationship and identify candidates with potent antifungal activity.

关 键 词：多样性导向合成 5 5-二甲基丁烯内酯 肟醚 合成 抑菌活性 

分 类 号：TQ450.1[化学工程—农药化工]