樟脑基喹喔啉类化合物的合成及其生物活性

Synthesis and Biological Activities of Camphor-Based Quinoxaline Cmpounds

将D-(+)-樟脑用二氧化锡氧化制得樟脑醌,再与系列取代邻苯二胺化合物缩合,合成得到19个樟脑基喹喔啉类化合物(3a^3s),并用UV-Vis,1 H NMR,13 C NMR,FT-IR和HR-MS(ESI)进行结构表征。初步的抑菌和除草活性测试表明:在用药量为50μg·mL-1时,目标化合物对花生褐斑病菌、小麦赤霉病菌、黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、玉米小斑病菌、西瓜炭疽病菌以及水稻纹枯病菌等8种植物病原菌具有一定的抑制活性,其中化合物樟脑基5,8-二溴喹喔啉3r对苹果轮纹病菌的抑制率达78.6%,优于阳性对照百菌清。在用药量为100μg·mL-1时,化合物樟脑基6-氟喹喔啉3f和樟脑基7-氟喹喔啉3g对油菜胚根生长的抑制率分别为75.8%和68.5%,均优于阳性对照丙炔氟草胺。

Camphoroquinone was prepared by oxidation of D-(+)-camphor using tin dioxide as oxidant.Then,nineteen camphor-based quinoxaline compounds(3a^3s)were synthesized by condensation of camphoroquinone with a series of substituted o-phenylenediamine compounds.The target products were characterized by UV-Vis,1 H NMR,13 C NMR,FT-IR and HR-MS(ESI).The preliminary test of antifungal activity and herbicidal activity showed that,at 50μg·mL-1,all the target compounds exhibited certain inhibition activity against eight tested plant pathogens,including Cercospora arachidicola,Gibberella zeae,Fusarium oxysporum f.sp.cucumerinum,Physalospora piricola,Alternaria solani,Bipolaris maydis,Colleterichum orbicalare,and Rhzioeotnia solani.The inhibition rate of compound camphor-based 5,8-dibromoquinoxaline 3r against Physalospora piricola was 78.6%,showing better antifungal activity than that of the positive control chlorothalonil.Also,at 100μg·mL-1,compounds camphor-based 6-fluoroquinoxaline 3f and camphor-based 7-fluoroquinoxaline 3g displayed herbicidal activities of 75.8%and 68.5%,respectively,against the root-growth of rape(B.campestris),showing better herbicidal activity than that of the positive control flumioxazin.