Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues.
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).
Sawada
Yoshihiro
Y
Agroscience Research Laboratories, Sankyo Co Ltd, 1041, Yasu, Yasu-cho, Yasu-gun, Shiga-ken 520-2342, Japan. sawada@br.sankyo.co.jp
Yanai
Toshiaki
T
Nakagawa
Harumi
H
Tsukamoto
Yoshihisa
Y
Yokoi
Shinji
S
Yanagi
Mikio
M
Toya
Tetsuya
T
Sugizaki
Hiroyasu
H
Kato
Yasuhito
Y
Shirakura
Hidetoshi
H
Watanabe
Tetsuo
T
Yajima
Yoshimi
Y
Kodama
Seiichirou
S
Masui
Akio
A
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
D006571:Heterocyclic Compounds; D006834:Hydrazines; D007306:Insecticides; C056565:1,2-dibenzoyl-tert-butylhydrazine; C082026:tebufenozide