Oxime ethers as potential juvenoids

✍ Scribed by Wimmer, Zdenêk ;Šaman, David ;Smolíková, Jorga ;Romaňuk, Miroslav

• Publisher: John Wiley and Sons
• Year: 1988
• Tongue: English
• Weight: 378 KB
• Volume: 1988
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198819881114

✦ Synopsis

Thc oximc cthcrs 7a-14a and 7b-10b were synthcsizcd in order to study their potential insecticidal properties. The respective syn-(7a-IOa) and anti-isomers (7b-10b) of the oxime ethers werc separatcd. Only syn-isomer formation was observed during the synthesis of 11a-14a. The structurcs of all compounds prcparcd (5.6.7a-14a. and 7b-10b) were determined spectroscopically, and the rcspcctive sq'ii-and unti-isomers of thc oxime ethers were identified. A brief survey of their biological activities shows that some of the compounds prepared possess higher activity against Muscn dontesrica and/or Galleria ntellonolln spccics than does hydropreme. 13a bearing a secondary alcohol group, were obtained by NaBH4 reduction of the respective compounds 7a, 7b, and l l a . The polarity of the cis-(Sa, 8b, and 12a), and trans-isomers (9a, 9b, and 13a) obtained is different, and therefore they can be separated by column chromatography. Difference was found in the IR spectra between the positions of the band corresponding to the 0 -H vibration; this was found at higher wave number for the cis-isomer than for the trans-isomer. The chemical shift values of the 7-H, 5-H, and 5'-H in the 'H NMR spectra were higher for the cis-isomer than for the trans-isomer.

In the search for compounds with the same effect as insect juvenile hormone, a series of oxime ethers of 2-(4-hydroxybenzyl)-Icyclohexanone was prepared. The synthesis of compounds bearing an analogous oxime ether grouping has been described by Japanese authors Several compounds of this series have shown high activity values (compared with those of methoprene) when tested on the last mosquito larval instar of Culex pipiens palens, Aedes aegypti, or Anopheles stephensi, re~pectively~,~).

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