去氢枞酸与SOCl2反应制得去氢枞酸酰氯(2);芳磺酰氯与乙二胺经N-酰化反应制得N-芳磺酰基乙二胺(4a~4k);在DMAP催化下,2分别与4a ~4k经N-酰化反应合成了11个新型的去氢枞酸基磺酰胺类化合物(5a~5k),其结构经1H NMR,13C NMR,IR和ESI-MS表征.生物活性测试结果表明,在用药量为50μg·mL-1时,5a ~5k对黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、花生褐斑病菌和小麦赤霉病菌有一定的抑菌活性,其中去氢枞酸基间甲基苯磺酰胺(5c)对番茄早疫病菌的杀菌活性最佳,抑制率为73.6%;在用药量为100 μg· mL-1时,大部分化合物对油菜的胚根生长有一定抑制作用,其中去氢枞酸基对甲氧基苯磺酰胺(5d)的抑菌活性最佳,抑菌率为57.1%.
Dehydroabietic acid acyl chloride (2) was prepared by the reaction of dehydroabietic acid with thionyl chloride.N-aryl sulfonyl ethylenediamines(4a ~ 4k) was prepared by the N-acylation of aryl sulfonyl chloride with ethylenediamine.Eleven novel dehydroabietic acid-based sulfonamide compounds(5a ~ 5k) were synthesized by N-acylation reaction of 2 with 4a ~ 4k,respectively,using DMAP as the catalyst.The structures were characterized by 1H NMR,13C NMR,IR and ESIMS.The preliminary bioassay showed that 5a ~ 5k exhibited certain fungicidal activities against Fusarium oxysporum f.sp.cucumerinum,Physalospora piricola,Alternaria solani,Cercospora Rachidicola and Fusarium graminearum.Inhibition rate against Alternaria solani of dehydroabietic acid-based mmethyl-benzenesulfonamide(5c) was 73.6% at 50μg · mL-1.Most of 5a ~ 5k exhibited certain growth inhibition activities against rape root (Brassica campestris),inhibition rate of dehydroabietic acid-based p-methoxyl-benzenesulfonamide(5d) was 57.1% at 100μg · mL-1.