Abstract

Butenolide derivatives have the potential to be effective and environmentally friendly antifouling agents. In the present study, a butenolide derivative was structurally modified into Boc-butenolide to increase its melting point and remove its foul smell. The structurally modified Boc-butenolide demonstrated similar antifouling capabilities to butenolide in larval settlement bioassays but with significantly lower toxicity at high concentrations. Release-rate measurements demonstrated that the antifouling compound Boc-butenolide could be released from polycaprolactone-polyurethane (PCL-PU)-based coatings to inhibit the attachment of foulers. The coating matrix was easily degraded in the marine environment. The performance of the Boc-butenolide antifouling coatings was further examined through a marine field test. The coverage of biofouler on the Boc-butenolide coatings was low after 2 months, indicating the antifouling potential of Boc-butenolide.

Highlights

  • Since the prohibition of tributyltin in 2008, many studies have attempted to discover novel antifouling compounds from marine natural products [1]

  • The concentration of Boc-butenolide measured at day 0 is around 64 ppm and dropped to approximately 50 ppm after 3 months in Artificial seawater (ASW)

  • The structure of butenolide was modified to Boc-butenolide to solve the problems of low melting point and smelliness of butenolide

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Summary

Introduction

Since the prohibition of tributyltin in 2008, many studies have attempted to discover novel antifouling compounds from marine natural products [1]. The first solution is to explore marine natural products from microorganisms, as microorganisms can produce a wide range of bioactive secondary metabolites [8,9,10]. The second solution involves structural optimisation using organic synthesis [6,11]. Secondary metabolites extracted from organisms are often complex in structure; they can be difficult to synthesise effectively in large quantities for commercial-scale usage [6,11]. By studying the structure– activity relationship of bioactive compounds isolated from organisms, pharmacophores that are responsible for antifouling abilities can be identified [11]. Optimisation of the compound’s structure is performed with the goal of increasing its potency, decreasing the toxicity of the original compound [12], improving other physical or chemical properties of the compound and simplifying the chemical structure for chemical synthesis

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