Furylchalcones as new potential marine antifoulants

Abstract

The control of marine biofouling by copper-based antifouling paints has a negative impact on the environment. Accordingly, these paints are becoming less friendly in several countries and are being subjected to greater ecological control. Therefore, the efforts are focused on the search for new-environmentally compounds to replace the utilization of copper biocides. Six furylchalcones obtained by biomass building block (furfural) were synthesized in this work, e.g., 3-(furan-2-yl)-1-phenylprop-2-en-1-one (3b); 3-(5-methylfuran-2-yl)-1-phenylprop-2-en-1-one (3c); 3-(furan-2-yl)-1-p-tolylprop-2-en-1-one (3d); 3-(5-methylfuran-2-yl)-1-p-tolylprop-2-en-1-one (3e); 3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (3f); 1-(2-hydroxyphenyl)-3-(5-methylfuran-2-yl)prop-2-en-1-one (3g). Antifouling paints containing these compounds were prepared at laboratory scale. In order to study antifouling paint performance, field trials were accomplished in Mar del Plata harbour (Argentina) during the summer. Furylchalcones were synthesized with high yields (˃ 87%) and the reaction was very selective (no competitive side reactions such as product decomposition, acetophenone condensation Cannizzaro's reaction, etc., were observed). Field trials revealed that paints containing furylchalcones showed strong antifouling effect on the fouling community, being 3d and 3g the most active against algae and calcareous tubeworms. The present work studies for the first time the significance of synthesizing furylchalcones from biomass building-blocks to generate new antifoulants to marine biofouling control.