title: Synthesis, crystal structures, insecticidal activities, and structure--activity relationships of novel N'-tert-Butyl-N'-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives.
abstract: Several series of novel N'-tert-butyl-N'-substituted-benzoyl-N-[di(octa)hydro]benzofuran{(2,3-dihydro)benzo[1,3]([1,4])dioxine}carbohydrazide derivatives Ia, Ib, IIa-IIg, IIIa, IIIb, and Va-Vc were designed and synthesized. Their structures were confirmed by (1)H NMR spectra, HRMS, and X-ray single-crystal structures. The larvicidal activities against oriental armyworm, beet armyworm, diamond-back moth, and corn borer of these compounds were evaluated and contrasted with those of RH-2485, JS-118, and ANS-118. The larvicidal activities against oriental armyworm indicate that monosubstituent or multisubstituents and the substituting group position cannot promote increasing activities and that the cycle region in the general structure of IIa-IIg is much more sensitive to activity than that in the general structure of Ia and Ib. The space volume of the A ring in the structure of Va cannot be too large; if it is, the activity will be decreased significantly. Stomach toxicities against beet armyworm, diamond-back moth, and corn borer of compounds Ia, Ib and IIg indicate that benzoheterocyclic analogues of N-tert-butyl-N,N'-diacylhydrazines show significant selectivities to different lepidopterous pests.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Huang
authors.forename: Yuxiu
authors.initials: Y
authors.lastname: Liu
authors.forename: Yongqiang
authors.initials: Y
authors.lastname: Li
authors.forename: Lixia
authors.initials: L
authors.lastname: Xiong
authors.forename: Zhipeng
authors.initials: Z
authors.lastname: Cui
authors.forename: Hongjian
authors.initials: H
authors.lastname: Song
authors.forename: Hongli
authors.initials: H
authors.lastname: Liu
authors.forename: Qiqi
authors.initials: Q
authors.lastname: Zhao
authors.forename: Qingmin
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000818:Animals; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D006834:Hydrazines; D007306:Insecticides; C019289:carbohydrazide