新型桃金娘烯醛基双酰胺-噻二唑化合物的合成及其抗真菌活性  

Synthesis and Antifungal Activities of Novel Myrtenal-based Bisamide-thiadiazole Compounds

作　　者：白雪[1] 段文贵[1] 林桂汕[1] 黄铎云 刘陆智[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]广西林产化学与工程重点实验室,广西南宁530008

出　　处：《合成化学》2015年第11期1000-1004,1012,共6页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(31460173);广西林产化学与工程重点实验室开放基金资助项目(GXFC13-02);广西研究生教育创新计划资助项目(YCSZ2014043)

摘　　要：以α-蒎烯为起始原料,经氧化制得桃金娘烯酸(3);脂肪族二酸在POCl3作用下与氨基硫脲经脱水环合制得脂肪族双噻二唑(4a^4h);4a^4h分别与3经脱水反应合成了8个新型的桃金娘烯醛基双酰胺噻二唑化合物(5a^5h),其结构经1H NMR,13C NMR,IR和ESI-MS表征。抗真菌活性测试结果表明,在用药量为50μg·m L-1时,5a^5h对黄瓜枯萎病菌、花生褐斑病菌、苹果轮纹病菌、番茄早疫病菌和小麦赤霉病菌均有一定的抑制作用,其中桃金娘烯醛-辛二酸基双酰胺-噻二唑(5f)对苹果轮纹病菌的抑制率为60.3%,桃金娘烯醛-丁二酸基双酰胺-噻二唑(5b)和桃金娘烯醛-癸二酸基双酰胺-噻二唑(5h)对小麦赤霉病菌的抑制率分别为52.8%和54.4%。Myrtenic acid（ 3） was prepared by oxidation of α-pinene. Aliphatic bis-thiadiazoles（ 4a ~4h） were prepared by reaction of aliphatic dicarboxylic acids with thiosemicarbazide in the presence of POCl3. Eight novel myrtenal-based bisamide-thiadiazole compounds（ 5a ~ 5h） were synthesized by condensation of 4a ~ 4h with 3,respectively. The structures were characterized by1 H NMR,13 C NMR,IR and ESI-MS. Antifungal activities test showed that 5a ~ 5h exhibited certain antifungal activities against Fusarium oxysporum f. cucumerinum,Cercospora arachidicola,Physalospora piricola,Alternaria solani and Fusarium graminearum at 50 μg · m L-1. Myrtenal-suberic acid-based bisamide-thiadiazole（ 5f） had inhibition rate of 60. 3% against Physalospora piricola,myrtenal-amber acid-based bisamide-thiadiazole（ 5b） and myrtenal-sebacic acid-based bisamide-thiadiazole（ 5h） had inhibition rates of 52. 8% and 54. 4% against Fusarium graminearum,respectively.

关 键 词：Α-蒎烯 桃金娘烯醛 双酰胺-噻二唑 合成 抗真菌活性 

分 类 号：O621.3[理学—有机化学]