Synthesis of amino alcohols from eugenol and their insecticidal activity against Sf9 cell line

Structural changes of natural biologically active compounds are an important strategy to improve biological activity and at the same time to reduce possible side effects.

Eugenol is a major constituent of clove essential oil with interesting biological activity, namely antimicrobial and antioxidant. Also the ß-amino alcohol moiety represents an important core in pharmaceutical industry; drugs, such as salbutamol and propranolol, are amongst the most important therapeutical agents on the market with this feature.

In the present work, a series of amino alcohols were prepared from eugenol epoxide; the epoxide was prepared from eugenol using m-CPBA, and was reacted with a series of amines affording the corresponding ß-amino alcohols in good yields. The compounds obtained were purified and fully characterised by usual analytical techniques, namely NMR spectroscopy and mass spectrometry.

Previous work carried out in our lab has shown interesting biological activity of some eugenol derivatives. The potential of these new compounds will be evaluated as biopesticides in assays using the Sf9 (Spodoptera frugiperda) insect cell line, and the results will be presented in this communication.