The small molecules that mediate chemical communication between nematodes-so-called 'nematode-derived-modular-metabolites' (NDMMs)-are of major interest due to their ability to regulate development, behavior, and life-history. nematodes produce an impressive diversity of structurally complex NDMMs, some of which act as primer pheromones capable of triggering irreversible developmental switches. Many of these NDMMs have only ever been found in but no attempts had been made to study their evolution by profiling closely related species. This study was designed to bring a comparative perspective to the biochemical study of NDMMs via the systematic MS/MS and NMR-based analysis of -metabolomes from over 30 species. We identified 36 novel compounds and found evidence for the convergent evolution of complex NDMMs in separate branches of the phylogeny. Our results demonstrate that biochemical innovation is a recurrent process in nematodes, a pattern likely typical across the animal kingdom.