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.

Antimicrobial dihydrobenzofurans and xanthenes from a foliar endophyte of Pinus strobus

“…( the first time as natural products, as they have previously only been generated as synthetic intermediates of antiinsectan and analgesic benzofuran compounds respectively (Huang et al, 2011;Occelli, 1979).…”

Alkylating Reagents Employed in Catellani‐Type Reactions

“…Remarkably,t he synthetic utility of this method is demonstrated in the elegant four-step synthesis of the insecticide fufenozide (107). [59] Direct annulation of commercially available Scheme25. Aziridines as the alkylating reagents for the Catellani-typereaction.…”

Direct Annulation between Aryl Iodides and Epoxides through Palladium/Norbornene Cooperative Catalysis

“…Finally,t he synthetic utility of this method is demonstrated in ac oncise synthesis of fufenozide (Scheme 2), [18] which is an effective insect growth regulator that shows high insecticidal activity towards plutella, xylostella,a nd mythimna. [19] Starting from the commercially available aryl iodide 1q and propyl oxide 2c,d irect annulation provided the key DHBF intermediate (3qc)in85% yield. Subsequent hydrolysis and peptide coupling with hydrazine 5 provided fufenozide in an excellent yield.…”