新型α-萜品烯马来酰亚胺基双磺酰胺化合物的合成及其除草活性  

Synthesis and Herbicidal Activities of Novel α-Terpinene-Maleimide-Based Disulfamide Compounds

作　　者：马献力[1,2] 黄建新[1] 段文贵[1] 莫启进[1] 林桂汕[1] 岑波[1] 黄翊[1] 

机构地区：[1]广西大学化学化工学院,广西南宁530004 [2]桂林医学院药学院,广西桂林541004

出　　处：《合成化学》2012年第2期180-185,共6页Chinese Journal of Synthetic Chemistry

基　　金：广西自然科学基金资助项目(2010GXNSFB013016);广西大学科研基金资助项目(XJZ100245);广西大学国家大学生创新性实验计划资助项目(200924)

摘　　要：以α-蒎烯为原料,在质子酸催化下发生Wagner-Meerwein重排得α-萜品烯(2);2与马来酸酐发生Diels-Alder环加成反应得α-萜品烯马来酸酐(3);3与水合肼反应制得N-氨基-α-萜品烯马来酰亚胺(4);在DMAP催化下,4与取代苯磺酰氯反应,合成了8个新型的α-萜品烯马来酰亚胺基双磺酰胺化合物(5a～5h),其结构经1H NMR,13C NMR,IR和ESI-MS表征。初步测定了4和5的除草活性,结果表明,在浓度为100μg·mL-1时,大部分化合物对油菜的胚根生长有一定的抑制作用,其中4的抑制率达84.6%。α-Pinene was converted into α-terpinene by Wagner-Meerwein rearrangement under catalysis of protonic acid,followed by Diels-Alder cycloaddtion reaction with maleic anhydride to obtain α-terpinene-maleic anhydride adduct（3）.N-amino-α-terpinene-maleimide（4） was prepared by reaction of 3 with hydrazine hydrate.Eight novel α-terpinene-maleimide-based disulfamides（5a^5h） were synthesized by reaction of substituted benzene sulfonyl chlorides with 4 using DMAP as the catalyst.The structures were characterized by 1H NMR,13C NMR,IR and ESI-MS.The preliminary herbicidal activities of 4 and 5 were investigated.The results showed that most compounds exhibited a certain growth inhibition against rape root（Brassica campestris）,in which 4 had inhibition rate of 84.6% at the concentration of 100 μg·mL-1.

关 键 词：Α-蒎烯 N-氨基-α-萜品烯马来酰亚胺 α-萜品烯马来酰亚胺基双磺酰胺 合成 除草活性 

分 类 号：O621.1[理学—有机化学]