Development of (phenoxyphenoxy)- and (benzylphenoxy)alkanaldoxime o-ethers as potent insect juvenile hormone mimics and their quantitative structure-activity relationship

Quantitative structure‐activity analysis of larvicidal 1‐(substituted benzoyl)‐2‐benzoyl‐1‐tert‐butylhydrazines against Chilo suppressalis

“…The coefficient of the AVw term for para substituents is more negative than for meta substituents in eqns (3) and (4). The steric allowance of the receptor to para substituents would be lower than that to meta substituents.…”

“…Among those tested, compounds 10, 12-14,29,32,33, 35, 49 and 56 showed too low an activity to measure, because of their limited solubility. The low activities of compounds 29, 32, 33, 35, 49 and 56 were predicted by eqn (4). Although the activity of the SCH, compound 14 was measured in the presence of PB, the suppression of the metabolic oxidation may not be complete, giving a less active compound(s) before arriving at the site of action.…”

“…12%6 is another indicator variable that takes the value of unity for compounds having the 2,6-disubstitution pattern and is otherwise zero. Equation 4 shows that the larvicidal activity of the compounds against rice stem borers increases with increase in the molecular hydrophobicity if substitution patterns are appropriate. Electron-withdrawing effects of ortho substituents are favourable to activity.…”

Development of (4-alkoxyphenoxy)- and (4-alkylphenoxy)alkanaldoxime O-ethers as potent insect juvenile hormone mimics and their structure-activity relationships

“…We thus, prepared 3-(4-benzylphenoxy)propyl isobutyl ether (20) (D, Wx, and T2 being 20.8, 6.23, and 5.05 A, respectively) and 3- was replaced by a variety of alkoxy and alkyl groups, with the aim of further exploring the structural conditions for high potency of this part of the molecules and of developing new JH-active compounds. We obtained 3-(4-isobutylphenoxy)-, 3-[4-(2-ethylbutyl)phenoxy]-, and 3-(4neopentylphenoxy)propionaldoxime O-isopropyl ethers (35, 37, 39), the activity of which against Culex pipiens was as high as that of the previously developed 3-[4-(3methylphenoxy)phenoxy]propionaldoxime O-isopropyl ether (Niwa et al, 1988) and 3-[4-(3-methylphenoxy)phenoxy]propyl isobutyl ether (Niwa et al, 1989), which are the most active of the JH mimics known so far against this mosquito. The quantitative structure-activity relationship of the set of the compounds was analyzed to predict the potency from the structural factors.…”

3D-QSAR studies on the biological activity of juvenile hormone mimetic compounds for Culex pipiens Larvae

“…Regulation, transportation, and feedback control of the JH titer were seemed to be altered by the JHAs in many pest insects (Mundall et al, 1979;Ilenchuk and Davey, 1985). The roles of JHA on regulation and inhibition of protein synthesis have also been demonstrated in the hanogenates and the imaginal disk of Drosophila melanogastor (Niwa et al, 1988;Niwa et al, 1989). Ovicidal effects of JH and JHAs have been reported in Rhodnius prolixus (Niwa et al, 1990) and C. pipien.…”