1-(2-羟基-4,5-亚甲二氧基)苯基-2-甲基丙烯酮类化合物的合成及抑菌活性

Synthesis and antifungal activity of compounds of 1-(2-hydroxy-4,5-methylenedioxy) phenyl-2-methyl propylene ketone

【目的】研究卡枯醇衍生物的抑菌活性,旨在探索其抑菌活性与构效关系。【方法】首先以芝麻酚、α-甲基丙烯酰氯为原料,通过傅克酰基化合成具有较高抑菌活性的卡枯醇衍生物,即化合物1(1-(2-羟基-4,5-亚甲二氧基)苯基-2-甲基丙烯酮),然后经醚化反应合成了8个目标化合物2a～2h,采用核磁共振仪(1 H-NMR、13 C-NMR)和质谱仪(ESI-MS)对化合物的结构进行了表征;最后采用生长速率法测定了化合物2a～2h对小麦赤霉病菌、番茄灰霉病菌、黄瓜炭疽病菌、马铃薯干腐病菌、水稻稻瘟病菌的抑菌活性。【结果】合成了8个1-(2-羟基-4,5-亚甲二氧基)苯基-2-甲基丙烯酮类化合物,其结构经1 H-NMR、13 C-NMR和ESI-MS予以了确认。抑菌活性测定结果表明,在质量浓度为100mg/L时,8种化合物对5种供试病原菌均有较高的抑菌活性,化合物2a、2b、2c和2f对供试菌种的菌丝生长抑制率均较高,其中对供试菌小麦赤霉病菌、番茄灰霉病菌的菌丝生长抑制率均基本达到了100.0%。此外,2a、2b、2c和2f对黄瓜炭疽病菌的菌丝生长抑制率均高于噻菌灵。【结论】合成的8个化合物对5种供试病原菌均有较高的抑菌活性,对部分菌种的菌丝生长抑制率高于噻菌灵原药。

【Objective】The study was about antifungal activities kakuol analogues.【Method】We took kakuol analogue：1-（2-hydroxy-4,5-methylenedioxy）phenyl-2-methyl propylene ketone from sesamol and α-methacryloylchloride by Friedel-Crafts,which showed a higher antifungal activity against some important plant pathogens,then synthesized 8 compounds from etherification,and their structures were characterized by 1H-NMR,13C-NMRand ESI-MS.Antifungal activity was tested by growth rate method.【Result】8 compounds of 1-（2-hydroxy-4,5-methylenedioxy） phenyl-2-methyl propylene ketone analogues were synthesized,and the structures were confirmed by 1H-NMR,13C-NMR,ESI-MS.When the mass concentration was 100 mg/L,all the compounds exhibited strong inhibiting effect against all the tested strains.In particular,compound 2a,2b,2c and 2f showed a higher bioactivity,the inhibition ratio to the Fusarium graminearum and Botrytis cirerea almost attained 100.0%.In addition,compound 2a,2b,2c and 2f showed a higher inhibition ratio to Gloeosporium orbiculare Ars than the positive control Triabendazole.【Conclusion】The compounds of 2a-2h exhibited good antifungal activities,some compounds had a higher rate of inhibition and better control effect than the positive control Triabendazole.