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Synthesis and insecticidal activity of benzoheterocyclic analogues of N ′‐benzoyl‐ N ‐( tert ‐butyl)benzohydrazide: Part 1. Design of benzoheterocyclic analogues
Author(s) -
Sawada Yoshihiro,
Yanai Toshiaki,
Nakagawa Harumi,
Tsukamoto Yoshihisa,
Yokoi Shinji,
Yanagi Mikio,
Toya Tetsuya,
Sugizaki Hiroyasu,
Kato Yasuhito,
Shirakura Hidetoshi,
Watanabe Tetsuo,
Yajima Yoshimi,
Kodama Seiichirou,
Masui Akio
Publication year - 2003
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.604
Subject(s) - spodoptera litura , carbohydrazide , cutworm , chemistry , benzothiazole , indole test , benzoxazole , benzoyl chloride , stereochemistry , medicinal chemistry , organic chemistry , pest analysis , biology , larva , botany , noctuidae
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). © 2002 Society of Chemical Industry