Molecular Diversity from Longipinenes of Lag. through Acid Catalysis: Biocidal Activity.

The search for new compounds with biocidal potential was carried out, focusing on the longipinenes - from the plant species Lag. Compounds , , and showed remarkable molecular diversity when treated in acidic reaction conditions. Protonic, Lewis, and heterogeneous compounds were used in the treatment. Three main models of reaction have been observed: isomerization of the double bond (-); rearrangements to longibornane-based skeleton (-) and ring-opening to himachalane-based skeleton (-). longibornane aldehydes and were obtained after epoxide opening under the same reaction conditions. The elucidation of the structures of the new compounds was carried out using spectroscopic data and was supported by computational theoretical calculations of C NMR spectra. Additionally, high-resolution mass spectrometry and single-crystal X-ray diffraction analysis were employed for certain compounds. Natural longipinenes -, methyl esters - of corresponding natural carboxylic acids and the isomerized and derivatives compounds - exhibit moderate to high insecticidal activity against and insects. Longipinene shows potent inhibition against the root growth of the plants and , as well as compound on the leaves of . Furthermore, significant ixocidal and nematicidal activity was found for this latter compound.