Singlet oxygen (O) and triplet chromophoric dissolved organic matter (CDOM*) are photochemically produced reactive intermediates responsible for the photodegradation of several micropollutants in the sunlit surface waters. However, elucidating the mechanism of reactions involving both O and CDOM* can be complicated by the deeply interconnected nature of these two reactive species. In this work, we synthesized a series of model compounds inspired by the chemical structure of fenfuram, a fungicide used in the 1980s, and used them to investigate structure-reactivity relationships in photodegradation reactions involving O and CDOM*. A combination of steady-state and time-resolved approaches was employed to successfully predict the extent of O-induced degradation. Conversely, the prediction of triplet-induced reactivity was complicated by the presence of repair mechanisms whose extent and relative importance were difficult to predict. The results of our work indicate that bimolecular rate constants measured via time-resolved techniques alone are not sufficient to accurately predict environmental half-lives, as intrinsic differences in the reaction mechanism can amplify the importance of secondary degradation pathways.