title: Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues.
abstract: The N'-benzoyl group of N-tert-butyl-N'-benzoyl-3,5-dimethylbenzohydrazide (1) was converted to a series of benzoheterocyclecarbonyl groups in order to investigate the potential usefulness of superimposing a hydrazine insecticide on 20-hydroxyecdysone. A series of analogues with benzodioxole, benzodioxane, benzodioxapine, indole, benzoxazole, benzoxazine or benzothiazole instead of the phenyl group of (1) were synthesized and tested for their insecticidal activity against the common cutworm (Spodoptera litura F). N-tert-Butyl-N'-(3,5-dimethylbenzoyl)-1,3-benzodioxole-5-carbohydrazide and N-tert-butyl-N'-(3,5-dimethylbenzoyl)-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide showed high insecticidal activities, superior to that of (1) and equal to that of the commercial insecticide tebufenozide (RH-5992).
authors.affiliation: Agroscience Research Laboratories, Sankyo Co Ltd, 1041, Yasu, Yasu-cho, Yasu-gun, Shiga-ken 520-2342, Japan. sawada@br.sankyo.co.jp
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sawada
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Yanai
authors.forename: Harumi
authors.initials: H
authors.lastname: Nakagawa
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Tsukamoto
authors.forename: Shinji
authors.initials: S
authors.lastname: Yokoi
authors.forename: Mikio
authors.initials: M
authors.lastname: Yanagi
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Toya
authors.forename: Hiroyasu
authors.initials: H
authors.lastname: Sugizaki
authors.forename: Yasuhito
authors.initials: Y
authors.lastname: Kato
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Shirakura
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Watanabe
authors.forename: Yoshimi
authors.initials: Y
authors.lastname: Yajima
authors.forename: Seiichirou
authors.initials: S
authors.lastname: Kodama
authors.forename: Akio
authors.initials: A
authors.lastname: Masui
mesh_terms: D000818:Animals; D015195:Drug Design; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D006834:Hydrazines / Q000737:chemistry* / Q000494:pharmacology / Q000633:toxicity; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology* / Q000633:toxicity; D007814:Larva / Q000187:drug effects; D015394:Molecular Structure; D018411:Spodoptera / Q000187:drug effects
chemical_list: D006571:Heterocyclic Compounds; D006834:Hydrazines; D007306:Insecticides; C056565:1,2-dibenzoyl-tert-butylhydrazine; C082026:tebufenozide