title: Quantitative structure-activity studies of insect growth regulators: XVIII. Effects of substituents on the aromatic moiety of dibenzoylhydrazines on larvicidal activity against the Colorado potato beetle Leptinotarsa decemlineata.
abstract: Larvicidal activity against the Colorado potato beetle Leptinotarsa decemlineata (Say) was measured for a series of N-tert-butyl-dibenzoylhydrazines having various substituents on the benzoyl (A-ring) moiety nearer to the tert-butyl group, with the other benzoyl (B-ring) moiety being unsubstituted. The effects of these substituent on the larvicidal activity were analyzed using classical quantitative structure-activity relationship (QSAR) procedures. The effects of substituents on the A-ring moiety on larvicidal activity were entirely different from those against the lepidopteran rice stem borer Chilo suppressalis (Walker) previously reported. Position-specific steric and hydrophobic effects, as well as certain substitution patterns, were likely to participate in modifying the larvicidal activity. The activity of para-substituted compounds was generally lower than that of un-, ortho- and meta-substituted compounds. Most multi-substituted compounds showed an activity equivalent to or lower than that of the unsubstituted compound. Among 46 compounds tested, the 2-sec-butoxy analogue was most potent against L decemlineata, although this compound had previously been shown to be only weakly active against C suppressalis.
authors.affiliation: Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. naka@kais.kyoto-u.ac.jp
authors.forename: Y
authors.initials: Y
authors.lastname: Nakagawa
authors.forename: G
authors.initials: G
authors.lastname: Smagghe
authors.forename: M
authors.initials: M
authors.lastname: Van Paemel
authors.forename: L
authors.initials: L
authors.lastname: Tirry
authors.forename: T
authors.initials: T
authors.lastname: Fujita
mesh_terms: D000818:Animals; D001517:Coleoptera / Q000187:drug effects*; D006834:Hydrazines / Q000737:chemistry* / Q000633:toxicity; D007306:Insecticides / Q000737:chemistry* / Q000633:toxicity; D007814:Larva / Q000187:drug effects*; D007928:Lethal Dose 50; D008954:Models, Biological; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship
chemical_list: D006834:Hydrazines; D007306:Insecticides; C082026:tebufenozide