N-氨乙基萜品烯马来酰亚胺基磺酰胺化合物的合成及抑菌活性

摘要

α-Pinene ( 1 ) was converted into α-terpinene ( 2 ) by Wagner-Meerwein rearrangement, followed by Diels-Alder cycloaddtion reaction of 2 with maleic anhydride to obtain α-terpinene-maleic anhydride adduct ( 3 ) . Then, twelve novel N-aminoethyl-terpinene-maleimide-based sulfamide compounds(5a -5l) were synthesized by the reaction of compound 3 with N-aryl sulfonyl ethylenediamine(4). The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The preliminary bioassay showed that the title compounds exhibited a certain fungicidal activities. Among then, compound 5c(R=3-CH3) had inhibition rates of 68. 8%, 68. 3%, 62. 3% and 53. 8% against Cercospora rachidicola, Alternaria solani, Physalospora piricola and Gibberella zeae at the concentration of 50 mg/L, respectively.%以α-蒎烯(1)为原料,经 Wagner-Meerwein 重排得α-萜品烯(2),2与马来酸酐发生Diels-Alder 环加成反应得到α-萜品烯马来酸酐(3),3再与N-芳磺酰基乙二胺(4)反应,合成得到12个新型 N-氨乙基萜品烯马来酰亚胺基磺酰胺类化合物(5a ~5l)。采用 FT-IR、1H NMR、13C NMR、ESI-MS和元素分析等多种手段对目标产物作了分析表征。初步的生物活性测试表明,目标化合物具有一定的抑菌活性,其中化合物5c(R=3-CH3)在质量浓度为50 mg/L时对花生褐斑病菌、番茄早疫病菌、苹果轮纹病菌和小麦赤霉病菌的抑制率分别达68.8%、68.3%、62.3%和53.8%。