N-(4-取代氨基磺酰基)苯基-酮基蒎酸酰胺的合成及生物活性  

Synthesis and biological activity of N-(4-substituted amino-sulfonyl)-phenyl-ketopinamides

作　　者：吴光燧[1] 段文贵[1] 林桂汕[1] 岑波[1] 赵莉[1] 雷福厚 

机构地区：[1]广西大学化学化工学院,南宁530004 [2]广西林产化学与工程重点实验室,南宁530008

出　　处：《农药学学报》2014年第1期8-13,共6页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金资助项目(31260164);广西林产化学与工程重点实验室开放基金资助项目(GXFC2012-01;GXFC11-02)

摘　　要：以D-(+)-樟脑磺酸为原料,经酰氯化和氧化反应制备得到酮基蒎酸(3),再经酰氯化得到酮基蒎酸酰氯(4)。4与对氨基苯磺酰胺类化合物发生N-酰化反应,得到8个未见文献报道的N-(4-取代氨基磺酰基)苯基-酮基蒎酸酰胺(5a^5h),其结构均经红外、质谱、核磁共振氢谱和碳谱确证。初步生物活性测试结果表明:目标化合物均有不同程度的杀菌和除草活性,其中5c(R=4-甲基嘧啶-2-基)在50μg/mL下对番茄早疫病菌Alternaria solani的抑制率达90.4%,化合物5e(R=噻唑-2-基)在100μg/mL下对油菜Brassica campestris胚根生长的抑制率达92.1%。Ketopinic acid （3） was prepared by the acyl chlorination and oxidation of D-（ ＋ ）- camphorsulfonic acid, followed by the acyl chlorination to obtain ketopinic acid chloride （4）. Then, eight novel N-（4-substituted amino-sulfonyl）-phenyl- ketopinamides 5a-5h were synthesized by the reaction of 4 with various 4-amino benzenesulfonamides. Their structures were confirmed by FI＇-IR, ESI-MS, 1H NMR and 13C NMR. The preliminary bioassay showed that, all the target compounds exhibited different fungicidal activity and herbicidal activity, in which compound 5c （R = 4-methyl- pyrimidin-2-yl） had the best inhibition rate of 90.4% against Alternaria solani at the concentration of 50μg/mL, and compound 5e （R = thiazol-2-yl） had the best growth inhibition rate of 92. 1% against rape root （Brassica campestris） at the concentration of 100 μg/mL.

关 键 词：樟脑 酮基蒎酸酰胺 合成 生物活性 

分 类 号：O622.6[理学—有机化学]