茴脑基双酰肼类化合物的合成及其植物病原菌抑制活性研究  

Synthesis of Anethole-based Diacylhydrazine Compounds and Their Antifungal Activity Against Plant Pathogens

作　　者：范钟天 段文贵[1] 林桂汕[1] 陈铭 黄媚[1] FAN Zhongtian;DUAN Wengui;LIN Guishan;CHEN Ming;HUANG Mei(School of Chemistry and Chemical Engineering,Guangxi University,Nanning 530004,China)

机构地区：[1]广西大学化学化工学院,广西南宁530004

出　　处：《林产化学与工业》2022年第3期117-125,共9页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(31870556)。

摘　　要：以茴脑氧化得到的茴香醛为原料,经与丙酸酐的Perkin缩合反应,制备保持有茴脑中苯丙素类C6-C3活性结构单元的羧酸,再经酯化、肼解和N-酰化反应,合成得到19个茴脑基双酰肼化合物(6a~6s)。采用FT-IR、^(1)H NMR、^(13)C NMR和ESI-MS对目标化合物结构进行了表征,并测试了目标化合物对8种植物病原菌的抑制活性。研究结果表明:在质量浓度50 mg/L时,目标化合物对8种植物病原菌均显示出一定的抑菌活性,其中,化合物6a(R=H)、6f(R=m-Cl)、6o(R=p-I)、6p(R=p-OH)和6q(R=p-t-Bu)对苹果轮纹病菌的抑制率分别为94.8%、96.1%、91.7%、96.1%和91.7%,均为A级活性水平,远优于阳性对照百菌清。化合物6f(R=m-Cl)和6p(R=p-OH)值得进一步研究。Anethole-based carboxylic acid,which maintained the phenylpropanoid C6-C3 active structural unit in anethole,was prepared by Perkin condensation reaction of propionic anhydride with anisaldehyde obtained by the oxidation of anethole.Then,nineteen anethole-based diacylhydrazine compounds(6a-6s)were synthesized via esterification,hydrazinolysis,and N-acylation reactions.All the target compounds were characterized by FT-IR,^(1)H NMR,^(13)C NMR,and ESI-MS.Their antifungal activity against eight tested plant pathogens was also evaluated.The results showed that,the target compounds showed certain antifungal activity against the eight tested plant pathogens,at the mass concentration of 50 mg/L.Among them,compounds 6a(R=H),6f(R=m-Cl),6o(R=p-I),6p(R=p-OH),and 6q(R=p-t-Bu)had inhibition rates of 94.8%,96.1%,91.7%,96.1%,and 91.7%against Physalospora piricola(all in A-class activity level),which were much better than that of the positive control chlorothalonil.Compounds 6f(R=m-Cl)and 6p(R=p-OH)were worthy of further investigation.

关 键 词：茴脑 茴香醛 双酰肼 抑菌活性 合成 

分 类 号：TQ351[化学工程]