Zhao Yu, Li Yongqiang, Ou Xiaoming, Zhang Pengxiang, Huang Zhiqiang, Bi Fuchun, Huang Runqiu, Wang Qingmin
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
J Agric Food Chem. 2008 Nov 12;56(21):10176-82. doi: 10.1021/jf802464d. Epub 2008 Oct 21.
A series of novel 2-aryl-pyrrole derivatives containing ester groups were synthesized, and their structures were characterized by (1)H NMR spectroscopy and elemental analysis. The insecticidal activities against oriental armyworm, mosquito, diamondback moth, green rice leafhopper, and bean aphids and acaricidal activities against spider mite of these new compounds were evaluated. The results of bioassays indicated that some of these title compounds exhibited excellent insecticidal and acaricidal activities. The insecticidal activities against oriental armyworm of compounds IVa, IVd, IVe, IVf, IVg, IVi, IVk, and IVp were equal to commercialized Chlorfenapyr, and the insecticidal activities of most of compounds IVb, IVc, IVd, IVf, IVg, IVj, IVk, IVl, IVs, IVt, IVu, IVw, IVx, IVz, and Chlorfenapyr against mosquito at 0.10 mg kg (-1) were 100%, and the acaricidal activities of compounds IVd, IVe, IVf, IVg, IVh, IVi, and IVk were equal or superior to Chlorfenapyr. Especially, the results indicated that the acaricidal activity of [4-bromo-2-(4-chlorophenyl)-3-cyano-5-(trifluoromethyl)pyrrol-1-yl]methyl 3-methylbutanoate ( IVg) against spider mite was 2.65-fold as high as that of Chlorfenapyr from the value of LC 50.
合成了一系列含酯基的新型2-芳基吡咯衍生物,并通过¹H NMR光谱和元素分析对其结构进行了表征。评价了这些新化合物对东方粘虫、蚊子、小菜蛾、稻绿蝽和豆蚜的杀虫活性以及对朱砂叶螨的杀螨活性。生物测定结果表明,其中一些目标化合物表现出优异的杀虫和杀螨活性。化合物IVa、IVd、IVe、IVf、IVg、IVi、IVk和IVp对东方粘虫的杀虫活性与商业化的溴虫腈相当,大多数化合物IVb、IVc、IVd、IVf、IVg、IVj、IVk、IVl、IVs、IVt、IVu、IVw、IVx、IVz和溴虫腈在0.10 mg kg⁻¹浓度下对蚊子的杀虫活性为100%,化合物IVd、IVe、IVf、IVg、IVh、IVi和IVk的杀螨活性与溴虫腈相当或优于溴虫腈。特别是,结果表明,从LC₅₀值来看,[4-溴-2-(4-氯苯基)-3-氰基-5-(三氟甲基)吡咯-1-基]甲基3-甲基丁酸酯(IVg)对朱砂叶螨的杀螨活性比溴虫腈高2.65倍。