Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides.
Dibenzoylhydrazines are the nonsteroidal ecdysone agonists. Using comparative molecular field analysis, we previously found that the alkyl side chain of 20-hydroxyecdysone (20E) is three-dimensionally superposable with one of their two aryl moieties. To identify the aryl moiety that is better superposable on the alkyl chain, we synthesized compounds in which one of the two aryl groups of tebufenozide (N-t-butyl-N-3,5-dimethylbenzoyl-N'-4-ethylbenzoylhydrazine) is replaced by alkyl groups such as C4H9, C5H11, and C6H13. The molting hormonal activity of these compounds was measured using cultured integuments prepared from rice stem borers, Chilo suppressalis Walker, in terms of stimulation of incorporation of N-acetyl-[14C]glucosamine. N-t-Butyl-N-3,5-dimethylbenzoyl-N'-acylhydrazines with a hexanoyl or heptanoyl group were about 20-fold higher than that of 20E, whereas N-acyl-N-t-butyl-N'-4-ethylbenzoylhydrazines with a hexanoyl or heptanoyl group were much weaker than 20E. Their larvicidal activity was also measured against rice stem borers. The former series of compounds were much more active than the other series as well as 20E. Thus, the benzoyl moiety of dibenzoylhydrazines, which is bound to the secondary nitrogen atom (-NH-), is replaceable by aliphatic acyl groups without greatly affecting the biological activities.
Shimizu
B
B
Department of Agricultural Chemistry, Kyoto University, Japan.
Nakagawa
Y
Y
Hattori
K
K
Nishimura
K
K
Kurihara
N
N
Ueno
T
T
D000215:Acylation; D000818:Animals; D004305:Dose-Response Relationship, Drug; D004440:Ecdysone / Q000494:pharmacology*; D006834:Hydrazines / Q000737:chemistry* / Q000494:pharmacology*; D007306:Insecticides / Q000737:chemistry* / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects*; D008958:Models, Molecular; D013329:Structure-Activity Relationship
D006834:Hydrazines; D007306:Insecticides; D004440:Ecdysone; C082026:tebufenozide