Synthesis and fouling resistance of capsaicin derivatives containing amide groups

Capsaicin, which inhibits the attachment and growth of fouling organisms, is a bioactive substance that is generally recognized as a highly active environmental algaecide agent. Its derivatives are simple in structure and have been proven to have low toxicity and be environmentally friendly. Six capsaicin derivatives were synthesized via Friedel-Crafts alkylation and characterized using melting point (MP) analysis, infrared (IR) spectroscopy, nuclear magnetic resonance (¹H NMR) spectroscopy and high-resolution mass spectrometry (HRMS). The inhibition effect and toxicity of these compounds towards Phaeodactylum tricornutum (P. tricornutum), Skeletonema costatum (S. costatum) and Chaetoceros curvisetus (C. curvisetus) were tested. The capsaicin derivatives all showed inhibitory effects. In particular, compound E with over 95% (3 mg·L^-1) inhibition and intermediate toxicity was superior to the other compounds, reflecting an environmentally friendly effect. This finding indicates that capsaicin derivatives possess the potential to become environmentally friendly algaecide agents. The fouling resistance of capsaicin derivatives incorporated into the coatings as antifouling agents was measured in the marine environment. The results showed that capsaicin derivatives possess excellent fouling resistance, with only a small amount of algae and muck attached to the tested panel at 90 days. The above results provide a scientific basis for the application of capsaicin derivatives as environmentally friendly antifouling agents.