1614231-76-3Relevant academic research and scientific papers
Design, synthesis, and biological evaluation of various α-substituted benzylpyrroles based on the structures of insecticidal chlorfenapyr and natural pyrrolomycins
Ma, Qiaoqiao,Liu, Yuxiu,Zhang, Pengxiang,Li, Yongqiang,Xiong, Lixia,Wang, Qingmin
, p. 6072 - 6081 (2014/07/21)
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, -1, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.
Design, synthesis, and biological evaluation of various β-substituted benzylpyrroles based on the structures of insecticidal chlorfenapyr and natural pyrrolomycins
Ma, Qiaoqiao,Liu, Yuxiu,Zhang, Pengxiang,Li, Yongqiang,Xiong, Lixia,Wang, Qingmin
, p. 6072 - 6081 (2015/04/22)
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 β-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 β-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-(β-(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, -1, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.
