Synthesis and insecticidal activity of benzoheterocyclic analogues of N'-benzoyl-N-(tert-butyl)benzohydrazide: Part 3. Modification of N-tert-butylhydrazine moiety.
Nineteen analogues were synthesized by modifying the tert-butylhydrazine moieties of N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-5-methyl-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide and N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-5-methylchromane-6-carbohydrazide (chromafenozide), and the synthesized analogues were evaluated for their insecticidal activity against Spodoptera litura F. While all of the synthesized analogues had insecticidal activity inferior to those of the lead compounds, several of the analogues nonetheless showed high insecticidal activity. Chromafenozide has shown very high selectivity toward lepidopteran species.
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
Tamagawa
Yasushi
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; D001578:Benzopyrans / Q000737:chemistry / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D006834:Hydrazines / Q000737:chemistry* / Q000494:pharmacology; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D007814:Larva / Q000187:drug effects; D007928:Lethal Dose 50; D015394:Molecular Structure; D018411:Spodoptera / Q000187:drug effects; D013329:Structure-Activity Relationship
D001578:Benzopyrans; D006571:Heterocyclic Compounds; D006834:Hydrazines; D007306:Insecticides; C056565:1,2-dibenzoyl-tert-butylhydrazine; C454111:chromafenozide