Ma Qiaoqiao, Liu Yuxiu, Zhang Pengxiang, Li Yongqiang, Xiong Lixia, Wang Qingmin
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.
J Agric Food Chem. 2014 Jul 2;62(26):6072-81. doi: 10.1021/jf501377t. Epub 2014 Jun 19.
On the basis of the structures of chlorfenapyr and dioxapyrrolomycin, a series of 2-benzylpyrroles with a hydroxyl, an alkyloxy, an acyloxy, an alkylsulfanyl, or an oxime moiety at the α-position of benzyl were designed and synthesized. Their insecticidal, acaricidal, and fungicidal activities were extensively investigated. The structure-activity relationship showed that benzylpyrroles bearing shorter α-alkyloxy groups gave better activities against most of the insect species; the alkylation of pyrrole usually gave increased activity. Among all compounds, (4-bromo-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) (5'j) exhibited the most outstanding insecticidal activities against oriental armyworm (IC₅₀=10 mg L⁻¹), diamondback moth (0.07 mg L⁻¹), corn borer (50 mg L⁻¹), and mosquito (0.04 mg L⁻¹), which are very close to those of chlorfenapyr (5, 0.08, <25, and <0.025 mg L⁻¹, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.
基于虫螨腈和二恶吡咯霉素的结构，设计并合成了一系列在苄基α位带有羟基、烷氧基、酰氧基、烷硫基或肟基的2-苄基吡咯。对它们的杀虫、杀螨和杀菌活性进行了广泛研究。构效关系表明，带有较短α-烷氧基的苄基吡咯对大多数昆虫种类具有更好的活性；吡咯的烷基化通常会提高活性。在所有化合物中，（4-溴-2-（α-（2,2,2-三氟乙氧基）-4-氯苄基）-1-（乙氧基甲基）-5-（三氟甲基）-1H-吡咯-3-腈）（5'j）对东方粘虫（IC₅₀ = 10 mg L⁻¹）、小菜蛾（0.07 mg L⁻¹）、玉米螟（50 mg L⁻¹）和蚊子（0.04 mg L⁻¹）表现出最出色的杀虫活性，这些数值与虫螨腈的活性（分别为5、0.08、<25和<0.025 mg L⁻¹）非常接近。此外，一些化合物还表现出广泛或选择性的杀菌谱。
