This chapter tells the story of a research thread that identified and modified a pharmaceutical that could be a component of environmentally benign fouling management coatings. First, I present the background context of biofouling and how fouling is managed. The major target of the research is disrupting transduction of a complex process in all macrofouling organisms: metamorphosis. Using a bioassay directed approach we first identified a pharmaceutical candidate. Then, based on structure function studies coupled with laboratory and field bioassays, we simplified the molecule, eliminating halogens and aromatic rings to a pharmacophore that could be readily broken down by bacteria. Next, we did further structure function studies coupled to lab and field bioassays of modifications that enabled delivery of the molecule in a variety of coatings. The outcome is a different way of thinking about managing fouling and concepts in which molecules are designed to perform a function and then degrade. This work is discussed in the context of existing fouling management approaches and business models which use long-lived broad-spectrum biocides which have consequences for human, environmental health, and food security.