姜黄素异噁唑和吡唑衍生物的合成及杀螨活性

为了寻求和开发新的基于天然产物的杀螨剂,在明确姜黄素具有杀螨活性,且其结构中的双羰基并非杀螨活性关键基团的基础上,设计并合成了15个姜黄素异噁唑和吡唑衍生物,其结构均经红外光谱、核磁共振氢谱和质谱分析确认。生物活性测定结果表明:几乎所有的目标化合物对朱砂叶螨Tetranychus cinnabarinus和柑橘全爪螨Panonychus citri均表现出了比先导化合物姜黄素更优异的触杀活性,其中化合物 4和11 的活性最为突出。处理48 h后,化合物 4 对朱砂叶螨和柑橘全爪螨的LC50值分别为333.0和156.0 mg/L,其毒力是姜黄素的6.35和4.56倍, 11 的LC50值分别为478.4和144.7 mg/L,毒力是姜黄素的4.42和4.92倍;相应地处理72 h后, 4 的LC50值分别为115.0和84.9 mg/L,其毒力是姜黄素的5.02和1.43倍, 11 的LC50值分别为91.0和68.7 mg/L,毒力是姜黄素的6.35和1.77倍。化合物 4和11 可作为进一步开发研究的具有杀螨活性的候选化合物。

Synthesis and acaricidal activity of curcumin isoxazole and pyrazole derivatives

In order to discover and develop the new natural products-based acaricidal agents,fifteen curcumin isoxazole and pyrazole derivatives were designed and synthesized,which based on the results of previous study.All structures of the title compounds were confirmed by IR,¹H NMR and MS.The acaricidal assay results showed that curcumin isoxazole and pyrazole derivatives exhibited higher contact activity than the lead compound curcumin.Both of compounds 4 and 11 showed higher contact activity to Tetranychus cinnabarinus and Panonychus citri than the other derivatives.The 48 h LC₅₀ values of 4 were 333.0 and 156.0 mg/L to T.cinnabarinus and P.citri,which exhibited about 6.35 and 4.56 fold higher acaricidal potency than curcumin,respectively.The 48 h LC₅₀ values of 11 were 478.4 and 144.7 mg/L to T.cinnabarinus and P.citri,which exhibited about 4.42 and 4.92 fold higher acaricidal potency than curcumin,respectively.The 72 h LC₅₀ values of 4 were 115.0 and 84.9 mg/L to T. cinnabarinus and P.citri,which exhibited about 5.02 and 1.43 fold higher acaricidal potency than curcumin,respectively.The 72 h LC₅₀ values of 11 were 91.0 mg/L and 68.7 mg/L to T.cinnabarinus and P.citri,which exhibited about 6.35 and 1.77 fold higher acaricidal potency than curcumin,respectively.These two compounds are promising candidates as novel acaricidal agents.