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 analog...

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Bibliographic Details
Published in:Pest management science 2003, Vol.59 (1), p.49-57
Main Authors: Sawada, Yoshihiro, Yanai, Toshiaki, Nakagawa, Harumi, Tsukamoto, Yoshihisa, Tamagawa, Yasushi, 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
Benzopyrans - chemistry
Benzopyrans - pharmacology
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
Hydrazines - pharmacology
insect growth regulator
insecticidal activity
insecticidal properties
Insecticides - chemical synthesis
Insecticides - chemistry
Insecticides - toxicity
Larva - drug effects
Lethal Dose 50
Molecular Structure
pest management
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrates
Spodoptera - drug effects
Spodoptera litura
Structure-Activity Relationship
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Summary: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.
ISSN:1526-498X
1526-4998
DOI:10.1002/ps.606