title: Design, synthesis, and biological evaluation of various α-substituted benzylpyrroles based on the structures of insecticidal chlorfenapyr and natural pyrrolomycins.
abstract: 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.
authors.affiliation: 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.
authors.forename: Qiaoqiao
authors.initials: Q
authors.lastname: Ma
authors.forename: Yuxiu
authors.initials: Y
authors.lastname: Liu
authors.forename: Pengxiang
authors.initials: P
authors.lastname: Zhang
authors.forename: Yongqiang
authors.initials: Y
authors.lastname: Li
authors.forename: Lixia
authors.initials: L
authors.lastname: Xiong
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000478:Alkylation; D000818:Animals; D009033:Culicidae / Q000187:drug effects / Q000254:growth & development; D005658:Fungi / Q000187:drug effects / Q000254:growth & development; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects / Q000254:growth & development; D007915:Lepidoptera / Q000187:drug effects / Q000254:growth & development; D008958:Models, Molecular; D015394:Molecular Structure; D025282:Mycelium / Q000187:drug effects / Q000254:growth & development; D010063:Ovum / Q000187:drug effects / Q000254:growth & development; D011722:Pyrethrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D040102:Tetranychidae / Q000187:drug effects / Q000254:growth & development
chemical_list: D005659:Fungicides, Industrial; D007306:Insecticides; D011722:Pyrethrins; D011758:Pyrroles; C053531:pyrroxamycin; C436643:chlorfenapyr
keywords: 2-benzylpyrrole; acaricidal activity; chlorfenapyr; dioxapyrrolomycin; fungicidal activity; insecticidal activity