L-香芹酮基吡唑-脲化合物的合成及其植物病原菌抑制活性研究  

Synthesis of L-Carvone-derived Pyrazole-urea Compounds and Their Antifungal Activity Against Plant Pathogens

作　　者：张兆雷 段文贵 马献力 林桂汕 温蓉竹 刘欣岩 ZHANG Zhaolei;DUAN Wengui;MA Xianli;LIN Guishan;WEN Rongzhu;LIU Xinyan(School of Chemistry and Chemical Engineering,Guangxi University,Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development,Nanning 530004,China)

机构地区：[1]广西大学化学化工学院,广西高校应用化学技术与资源开发重点实验室,广西南宁530004

出　　处：《林产化学与工业》2025年第1期89-98,共10页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(32260366)。

摘　　要：为实现香芹酮的高值化利用,以L-香芹酮(1)为原料,先通过酰化反应制备L-甲酰化香芹酮(2),再经过缩合以及亲核加成反应,合成得到22个未见文献报道的L-香芹酮基吡唑-脲化合物4a~4v。通过FT-IR、1H NMR、13C NMR、HRMS和单晶X射线衍射对化合物结构进行了分析和表征,并测试了目标化合物对8种植物病原菌的抑制活性。抑菌活性测试表明:在质量浓度为50 mg/L时,目标化合物对8种供试植物病菌均有一定的抑制活性,其中化合物4b(R=p-CH3Ph)对苹果轮纹病菌的抑制率为79.2%(为B级活性水平),优于阳性对照百菌清(抑制率为75.0%)。化合物4u(R=异丙基)对黄瓜枯萎病菌、苹果轮纹病菌和水稻纹枯病菌的抑制率分别为78.2%、 76.7%和79.6%(均为B级活性水平),具有一定的广谱抑菌活性。For high value-added utilization of carvone,L-Formylated carvone was prepared at first by acylation reaction of L-carvone.Then,twenty-two L-carvone-derived pyrazole-urea compounds 4a-4v which had not been reported before were synthesized through condensation and nucleophilic addition reactions.The target compounds were characterized by FT-IR,1 H NMR,13 C NMR,HRMS,and single crystal X-ray diffraction,and their antifungal activity against eight tested plant pathogens was also evaluated.The antifungal activity test of the target compounds showed certain antifungal activity against eight tested plant pathogens at the mass concentration of 50 mg/L.Among them,compound 4b(R=p-CH 3 Ph)had inhibition rate of 79.2%,against Physalospora piricola(in B-class activity level),better than that of the positive control chlorothalonil(inhibition rate of 75.0%).Besides,compound 4u(R=isopropyl)displayed certain broad-spectrum antifungal activity owing to its good inhibition rates of 78.2%,76.7%,and 79.6%,against Fusarium oxysporum f.sp.cucumerinum,Physalospora piricola,and Rhizoctonian solani,respectively(all in B-class activity level).

关 键 词：L-香芹酮 吡唑-脲 合成 抑菌活性 

分 类 号：TQ35[化学工程]