噻二唑-丙烯酰胺吗啉晶体结构解析及抗烟草花叶病活性研究  

Detection of thiadiazole-acryloyl-morpholine crystal structure and study of its anti-TMV activity

作　　者：李雅泽 付怡宁 杨宇 张金林[1] 陈来 LI Yaze;FU Yining;YANG Yu;ZHANG Jinlin;CHEN Lai(College of Plant Protection,Hebei Agriculture University,Baoding 071000,China;Agriculture and Rural Bureau of Gu’an County of Hebei,Gu’an 065500,China)

机构地区：[1]河北农业大学植物保护学院,河北保定071001 [2]河北省固安县农业农村局,河北固安065500

出　　处：《河北农业大学学报》2025年第1期66-72,共7页Journal of Hebei Agricultural University

基　　金：河北省重点研发计划项目(22326503D).

摘　　要：植物免疫诱导剂作为新型的生态农药,其创制研究一直是杀菌剂开发的热点。为发现新型的杂环类植物免疫诱导剂,本研究以具有杀菌活性的肉桂丙烯酰胺骨架为先导结构,通过生物电子等排替换的分子设计策略,引入具有植物免疫诱导活性杂环噻二唑骨架,设计成目标分子4-[3-(4-甲基-1,2,3-噻二唑-5-基)]-3-(4-叔丁基苯基)-1-吗啉。经4步合成目标产物,通过核磁共振、高分辨质谱和单晶X射线衍射对其结构进行了表征,目标化合物的晶体属于单斜晶系,空间群C2/c,a=6.6643(5),b=12.4451(10),c=12.6992(11)Å,V=1008.84(14)Å^(3),Z=2,Dc=1.223 Mg/m^(3),F(000)=396,μ=0.179 mm^(-1)。经活体盆栽诱导烟草抗TMV活性评价发现,目标化合物5在烟草上对TMV分别表现出65%的钝化活性和69%的诱导活性,表明本研究发现的目标分子可作为植物免疫诱导剂候选化合物,可用于后续应用研究。Plant elicitor is a novel eco-pesticide whose discovery has been becoming a hotspot in fungicide.To discover new heterocyclic plant elicitors,the cinnamon acrylamide skeleton was used as a fungicidal lead in this study.And heterocyclic thiadiazole with induction ability of plant immune activity was introduced through a bioisosteric replacement molecular design strategy,resulting in the target molecule 4-[3-(4-Me-1,2,3-thiadiazol-5-yl)]-3-(4-t-Bu-phenyl)-1-morpholine.Then it was synthesized by four steps,and its structure was also characterized by Nuclear Magnetic Resonance,High-Resolution Mass Spectrometry and single-crystal X-ray diffraction.The crystal of the target compound belongs to monoclinic with space group C2/c with a=6.6643(5),b=12.4451(10),c=12.6992(11)Å,V=1008.84(14)Å^(3),Z=2,Dc=1.223 Mg/m^(3),F(000)=396 and μ=0.179 mm^(-1).In evaluation of the anti-TMV activity,the target compound 5 exhibited 65%inactivation activity and 69%induction activity against tobacco mosaic virus(TMV)on tobacco,respectively.In total,compound 5 would be a promising plant elicitor candidate,and deserve next application study.

关 键 词：合成 丙烯酰胺 噻二唑 晶体结构 抗TMV活性 

分 类 号：S482[农业科学—农药学]