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

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.