4-(吩嗪-1-酰氧基)肉桂酸酯和N-吩嗪-1-甲酰基-N'-肉桂酰基乙二胺的合成及生物活性  

Synthesis and biological activities of 4-(phenazine-1-carboloxyl)cinnamic acid esters and N-phenazine-1-carboxyl-N′-(substituted)-cinnamyl ethylenediamins

作　　者：高亚强 马俊豪 周蒲 游江 张列雄 徐志红[1,2] GAO Yaqiang;MA Junhao;ZHOU Pu;YOU Jiang;ZHANG Liexiong;XU Zhihong(School of Agriculture,Yangtze University,Jingzhou 434025,Hubei Province,China;Institute of Pesticides,Yangtze University,Jingzhou 434025,Hubei Province,China)

机构地区：[1]长江大学农学院,湖北荆州434025 [2]长江大学农药研究所,湖北荆州434025

出　　处：《农药学学报》2022年第1期49-58,共10页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31772170).

摘　　要：以不同取代的肉桂酸为原料,通过酯化反应和酰基的亲核取代反应对天然产物吩嗪-1-羧酸(申嗪霉素)进行了结构修饰,合成了2个系列含肉桂酸结构片段的吩嗪-1-羧酸酯类衍生物5 a~5 f和吩嗪-1-甲酰胺类衍生物10 a~10 r,所有衍生物的结构均得到核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱确证。分别采用菌丝生长速率法和培养皿法测定了目标化合物的杀菌活性和除草活性。杀菌活性测定结果表明:在浓度为0.20 mmol/L时,大部分吩嗪-1-羧酸酯类衍生物对水稻稻瘟病菌Pyricularia oryzae具有较好的抑制作用,其中化合物5a的抑制率为78.37%,略低于对照药剂吩嗪-1-羧酸(86.91%)。除草活性测定结果表明:在0.50 mmol/L下,化合物10b、10e和10f对油菜根长的抑制率均超过80%,化合物10e对油菜的抑制效果与对照药剂丁草胺相当。本文所合成的目标化合物不仅具有一定的杀菌活性,而且还具有较好的除草活性,部分化合物的除草活性与对照药剂相当,研究结果为吩嗪-1-羧酸的结构改造提供了新思路。The phenazine-1-carboxylic acid was modified by esterification and nucleophilic substitution of acyl from different substituted cinnamic acid,two series of phenazine-1-carboxylate derivatives containing cinnamic acid segments 5a-5f and phenazine-1-formamide derivatives 10a-10r were synthesized.The structures of these derivatives were confirmed by 1H NMR,13C NMR and high resolution mass spectrometry.The fungicidal activity and herbicidal activitiy of the target compounds were determined by mycelium growth rate method and culture dish method.The results of fungicidal activity assay showed that most phenazine-1-carboxylate derivatives had good inhibitory effect on Pyricularia oryzae at the concentration of 0.20 mmol/L,and the inhibitory rate of compound 5a was 78.37%,it was slightly lower than phenazine-1-carboxylic acid(86.91%).The results of herbicidal activity assay showed that the inhibition rates of 10b,10e and 10f on the root length of rape were more than 80%,and the inhibitory effect of 10e on rape was similar to that of butachlor at the concentration of 0.50 mmol/L.The target compound synthesized in this paper not only has certain fungicidal activity,but also has good herbicidal activity,the herbicidal activity of some target compounds is similar to that of control agents,this study provides a new idea for the structural modification of phenazine-1-carboxylic acid.

关 键 词：吩嗪-1-羧酸 申嗪霉素 肉桂酸 天然产物 杀菌活性 除草活性 

分 类 号：O626.4[理学—有机化学] TQ450.11[理学—化学]