Multidimensional characterization of a new antifouling xanthone: Structure-activity relationship, environmental compatibility, and immobilization in marine coatings

Abstract

The accumulation of marine biofouling on ship hulls causes material damage, the spread of invasive species, and, indirectly, an increase in full consumption and subsequent pollutant gas emissions. Most efficient antifouling (AF) strategies rely on the conventional release of persistent, bioaccumulative, and toxic biocides incorporated in marine coatings. A simple oxygenated xanthone, 3,4-dihydroxyxanthone (1), was previously reported as a promising AF agent toward the settlement of Mytilus galloprovincialis larvae, with a therapeutic ratio higher than the commercial biocide Econea®. In this work, a structure-AF activity relationship study, an evaluation of environmental fate, and an AF efficiency in marine coatings were performed with compound 1. Hydroxy or methoxy groups at 3 and 4 positions in compound 1 favored AF activity, and groups with higher steric hindrances were detrimental. Compound 1 demonstrated low water-solubility and a short half-life in natural seawater, contrary to Econea®. In silico environmental fate predictions showed that compound 1 does not bioaccumulate in organism tissues, in contrast to other current emerging biocides, has a moderate affinity for sediments and slow migrates to ground water. No toxicity was observed against Vibrio fischeri and Phaeodactylum tricornutum. Polyurethane-based marine coatings containing compound 1 prepared through an innovative non-release-strategy were as efficient as those containing Econea® with low releases to water after 45 days. This proof-of-concept helped to establish compound 1 as a promising eco-friendly AF agent.