樟脑酸基苯磺酰胺类化合物的合成及抑菌活性研究  

Synthesis and Fungicidal Activity of Camphoric Acid-based Benzenesulfonamide Compounds

作　　者：马献力[1,2] 闵方倩 段文贵[1] 李芳耀[1,2] 刘陆智[1] 岑波[1] 雷福厚 

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 [3]广西林产化学与工程重点实验室,广西南宁530008

出　　处：《林产化学与工业》2015年第1期30-38,共9页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(31260164);广西高校科学技术研究重点项目(ZD2014098);广西林产化学与工程重点实验室开放基金项目(GXFC12-01)

摘　　要：以樟脑酸为原料,经过脱水反应制备樟脑酸酐。将取代苯磺酰氯与乙二胺反应得到N-芳磺酰基乙二胺,再与樟脑酸酐反应,合成得到11个新型樟脑酸基苯磺酰胺类化合物,分别为:樟脑酸基苯磺酰胺(4a)、樟脑酸基对甲基苯磺酰胺(4b)、樟脑酸基间甲基苯磺酰胺(4c)、樟脑酸基对甲氧基苯磺酰胺(4d)、樟脑酸基间甲氧基苯磺酰胺(4e)、樟脑酸基对氟苯磺酰胺(4f)、樟脑酸基邻氟苯磺酰胺(4g)、樟脑酸基对氯苯磺酰胺(4h)、樟脑酸基间氯苯磺酰胺(4i)、樟脑酸基对溴苯磺酰胺(4j)和樟脑酸基间溴苯磺酰胺(4k)。目标产物的适宜合成条件为:以无水乙醇作溶剂,反应温度80℃,n(樟脑酸酐)∶n(N-芳磺酰基乙二胺)为1∶1.2。利用FT-IR、1H NMR、13C NMR和ESI-MS等多种手段对目标化合物进行结构表征。初步的生物活性测试表明,在50 mg/L质量浓度下,大部分化合物具有一定的抑菌活性,其中化合物4a和4e对苹果轮纹病菌的抑制率达94.8%,化合物4h对番茄早疫病菌的抑制率达86.9%。Camphoric anhydride was prepared via dehydration reaction using camphoric acid as starting material. Then,N-aryl sulfonyl ethyenediamines were synthesized by the reaction of ethylenediamine with substituted benzenesulfonyl chlorides,followed by the reaction of camphoric anhydride with N-aryl sulfonyl ethyenediamines to obtain eleven novel camphoric acid-based benzenesulfonamide compounds： camphoric acid-based benzenesulfonamide（ 4a）, camphoric acid-based p-methylbenzenesulfonamide（ 4b）, camphoric acid-based m-methyl-benzenesulfonamide（ 4c）, camphoric acid-based p-methoxybenzenesulfonamide（ 4d）, camphoric acid-based m-methoxy-benzenesulfonamide（ 4e）, camphoric acid-based p-fluorobenzenesulfonamide（ 4f）, camphoric acid-based o-fluoro-benzenesulfonamide（ 4g）, camphoric acid-based p-chlorobenzenesulfonamide（ 4h）, camphoric acid-based m-chloro-benzenesulfonamide（ 4i）, camphoric acid-based p-bromo-benzenesulfonamide（ 4j）, and camphoric acid-based m-bromo-benzenesulfonamide（ 4k）. The synthetic conditions were investigated preliminarily. The suitable synthetic conditions for the target compounds were as follows： anhydrous ethanol as solvent,reaction temperature 80 ℃,n（ camphoric anhydride） ∶ n（ N-aryl sulfonyl ethyenediamine） 1 ∶ 1. 2. The target compounds were characterized by FT-IR,^1H NMR,^13 C NMR and ESI-MS,respectively. The preliminary bioassay showed that most of the title compounds exhibited certain fungicidal activity at the concentration of 50 mg / L,in which compounds 4a and 4e had inhibition rate of 94. 8 % against Physalospora piricola,and compound 4h had inhibition rate of 86. 9 % against Alternaria solani.

关 键 词：樟脑酸 磺酰胺 合成 抑菌活性 

分 类 号：TQ351[化学工程]