摘要
以天然产物α-蒎烯为原料,经多步反应合成了9个新型的α-蒎烯基苯磺酰胺类化合物(7a^7i),其结构经1H NMR、13C NMR、 FT-IR和MS(ESI)表征。采用离体法测试了化合物的抗真菌活性。结果表明:在50μg·mL-1浓度下,目标化合物对黄瓜枯萎病菌、花生褐斑病菌、苹果轮纹病菌、小麦赤霉病菌以及番茄早疫病菌等5种植物病原菌有一定的抑制活性,其中化合物α-蒎烯基p-氯苯基磺酰胺(7d, R=p-Cl)和α-蒎烯基o-硝基苯基磺酰胺(7h, R=o-NO2)对苹果轮纹病菌的抑制率分别为83.9%和79.6%(B级活性水平),优于阳性对照百菌清(75.0%);化合物α-蒎烯基m-甲基苯基磺酰胺(7b, R=m-Me)对番茄早疫病菌的抑制率为82.2%(B级活性水平),优于阳性对照百菌清(73.9%)。
Nine novel α-pinene-based benzene sulfonamide compounds(7 a^7 i) were synthesized via a multiple-step process using α-pinene as starting material. The structures of target compounds were characterized by 1H NMR, 13C NMR, FT-IR and MS(ESI). The antifungal acivities of 7 a^7 i were investigated by in vitro method. The results showed that, at the concentration of 50 μg·mL-1, the target compounds exhibited a certain inhibition activities against the five tested plant pathogens, including Fusarium oxysporum f. sp. cucumerinum, Cercospora arachidicola, Physalospora piricola, Gibberella zeae, and Alternaria solani, in which compounds α-pinene-based p-chlorophenyl sulfonamide(7 d, R=p-Cl) and α-pinene-based o-nitrophenyl sulfonamide(7 h, R=o-NO2) had inhibition rate of 83.9% and 79.6%(B-class activity level), respectively, against Physalospora piricola, showing better antifungal activities than that of the positive control chlorothanil with inhibition rate of 75.0%, and compound α-pinene-based m-methylphenyl sulfonamide(7 b, R=m-Me) had inhibition rate of 82.2%(B-class activity level) against Alternaria solani, showing better antifungal activity than that of the positive control chlorothanil with inhibition rate of 73.9%.
作者
岑波
李龙生
段文贵
林桂汕
陈铭
陆顺忠
CEN Bo;LI Long-sheng;DUAN Wen-gui;LIN Gui-shan;CHEN Ming;LU Shun-zhong(College of Chemistry and Chemical Engineering,Guangxi University,Nanning 530004,China;Guangxi Academy of Forestry,Nanning 530002,China)
出处
《合成化学》
CAS
北大核心
2020年第3期174-180,共7页
Chinese Journal of Synthetic Chemistry
基金
国家重点研发计划项目(2018YFD0600401)
国家自然科学基金资助项目(31870556)。
关键词
Α-蒎烯
苯磺酰胺
合成
百菌清
病原菌
抗真菌活性
α-pinene
benzene sulfonamide
synthesis
chlorothanil
plant pathogen
antifungal activity
