Within the context of environmentally friendly methods for the elimination of surface-water pollutants, the photodegradation of the phenolic pesticides bromoxynil (BXN) and dichlorophen (DCP) under simulated natural conditions has been studied. The work was done in the presence of the visible-light absorber photosensitizer riboflavin (Rf), usually present in trace quantities in natural waters. Under aerobic conditions, an efficient photooxidation of both pesticides was observed. The relatively intricate photochemical mechanism involves pesticide and oxygen consumption and, to a lesser extent, Rf degradation. The kinetic and mechanistic study supports that both H2O2 and singlet molecular oxygen, O-2((1)Delta(g)), are involved in the process. Kinetic data for the O-2((1)Delta(g))-mediated oxidation indicate that BXN and DCP are photodegraded with this species faster than the parent compound phenol, very frequently employed as a model for aquatic contaminants, likely due to their lower pK(a) values. This observation allows the design of phenolic pesticides with different photodegradation rates under environmental conditions. (c) 2010 Elsevier B.V. All rights reserved.