Quantitative structure-activity studies of insect growth regulators: XIX. Effects of substituents on the aromatic moiety of dibenzoylhydrazines on larvicidal activity against the beet armyworm Spodoptera exigua.
Larvicidal activity against the beet armyworm, Spodoptera exigua (Hübner), was measured after topical treatment for a series of N-tert-butyl-dibenzoylhydrazines having various substituents in the benzoyl (A-ring) moiety closer to the tert-butyl group, the other benzoyl (B-ring) moiety being unsubstituted. The effects of substituents on the larvicidal activity were analyzed using the classical quantitative structure-activity relationship (QSAR) procedure. Introduction of hydrophobic substituents with a small volume into any position was favourable to activity. The existence of electron-withdrawing substituents at ortho positions was also favourable to activity. For multi-substituted compounds, physico-chemically unknown unfavourable factors were suggested to remain after separating common substituent effects derived from QSAR for mono-substituted analogues. With the exception of the unsubstituted compound RH-5849, the effect of substituents in the A-ring moiety on the larvicidal activity was similar to those found with the lepidopteran rice stem borer, Chilo suppressalis (Walker). The larvicidal activity of RH-5849 against S exigua was significantly lower than the value predicted from the correlation between activities against S exigua and C suppressalis. Topical treatment with piperonyl butoxide, a synergist inhibiting oxidative metabolism, slightly enhanced the larvicidal activity of RH-5849 against S exigua.
Nakagawa
Yoshiaki
Y
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Kyoto 606-8502, Japan. naka@kais.kyoto-u.ac.jp
Smagghe
Guy
G
Tirry
Luc
L
Fujita
Toshio
T
D000465:Algorithms; D000818:Animals; D006834:Hydrazines / Q000737:chemistry / Q000633:toxicity; D057927:Hydrophobic and Hydrophilic Interactions; D007605:Juvenile Hormones / Q000737:chemistry / Q000633:toxicity*; D007814:Larva / Q000187:drug effects / Q000254:growth & development; D007915:Lepidoptera / Q000187:drug effects / Q000254:growth & development*; D007928:Lethal Dose 50; D010882:Piperonyl Butoxide / Q000633:toxicity; D021281:Quantitative Structure-Activity Relationship; D018411:Spodoptera / Q000187:drug effects / Q000254:growth & development
D006834:Hydrazines; D007605:Juvenile Hormones; C056565:1,2-dibenzoyl-tert-butylhydrazine; D010882:Piperonyl Butoxide