Synthesis and insecticidal activity of benzoheterocyclic analogues of N′-benzoyl-N-(tert-butyl)benzohydrazide: Part 2. Introduction of substituents on the benzene rings of the benzoheterocycle moiety

• Published in: Pest management science 2003, Vol.59 (1), p.36-48
• Main Authors: 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
• Format: Article
• Language: English
• Subjects: 20-hydroxyecdysone; Animals; benzene; Biological and medical sciences; Chemical control; chromafenozide; common cutworm; Control; ecdysone agonist; Fundamental and applied biological sciences. Psychology; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Heterocyclic Compounds - toxicity; Hydrazines - chemistry; insect growth regulator; insecticidal activity; insecticidal properties; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - toxicity; Larva - drug effects; lethal concentration 50; Lethal Dose 50; Molecular Structure; pest management; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; Spodoptera - drug effects; Spodoptera litura; Structure-Activity Relationship
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.605

A series of N′-benzoheterocyclecarbonyl-N-tert-butyl-3,5-dimethylbenzohydrazide analogues possessing a variety of substituents on the benzene rings of the benzoheterocyle moieties were synthesized and tested for their insecticidal activity. The introduction of a methyl group at the R1 position of the benzoheterocycle moiety strongly increased the insecticidal activity. Among the analogues synthesized, N′-tert-butyl-N′-(3,5-dimethylbenzoyl)-5-methyl-6-chromanecarbohydrazide showed the highest insecticidal activity (LC50 = 0.89 mg litre−1).