Oxime Ethers: New Potent Insect Growth Regulators

Development of (phenoxyphenoxy)- and (benzylphenoxy)propyl ethers as potent insect juvenile hormone mimetics

“…The structure-activity profile of the new class of compounds is in accord with that of the previous terpenoid oximes. Moreover, the position of the oxime O-ether function in a molecule has been found important for high activity, 3-(4-phenoxyphenoxy)or 3-(4-benzylphenoxy)propionaldoxime O-ethers being dozens of times more potent than the corresponding acetaldoxime O-ethers. Recently, propionaldoxime O-2-(4-phenoxyphenoxy)ethyl ethers has been reported, where the oxime function is built in the structure in the reverse of our oxime ethers (Ohsumi et al, 1985). In the same run of assays with our compounds, they were highly active, pIm (M) against C. pipiens being 9.50 (Niwa et al, 1987).…”

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

“…As in previous results (Niwa et al, 1988), the activity of the propionaldoximes was dozens of times higher than that of the corresponding acetaldoximes, suggesting that there was a position-specific interaction site on the surface of the JH receptor. These length and positional effects are thought to be at operate in a variety of JH-active derivatives (Henrick, 1982) as well as in the phenoxyphenoxy types of compounds (Karrer and Farooq, 1981; Ohsumi et al, 1985).…”

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

“…More important is the extension of the results of other classes of compounds. We have estimated the structural parameters of highly active propionaldoxime 0-2-(4-phenoxyphenoxy)ethyl ether (Ohsumi et al, 1985) in which the oxime moiety is built in the structure in the reverse of the present series of compounds, and we predicated the p/50 value by eq 4 to be 9.00. The activity tested in our laboratory of the compound provided by the Sumitomo Chemical Co., Ltd., was 9.50, which agreed with the prediction.…”