Chloroacetanilide herbicides (e.g. alachlor and metolachlor) and their breakdown products are frequently found in agriculturally impacted and other natural waters. Although these compounds are usually present at low concentrations in aquatic systems, defining their fate and attenuation rate is important because they can be toxic at comparatively low exposure levels. This paper summarizes results from a four-year research program assessing factors that affect herbicide attenuation rates and breakdown product formation patterns in aquatic systems. Over 70 different field microcosms (11.3 m³ cylindrical fiberglass tanks) were selectively manipulated (in replicate) to create nine unique aquatic ecosystems for this study. Alachlor and/or metolachlor were added to these units and transformations were observed over time. Alachlor half-lives ranged from 6.0 days to more than 100 days depending upon the temperature, oxygen conditions, and the nutrient conditions in the microcosm waters. The highest rates of alachlor decay were observed in warm, nutrient-rich, anaerobic water columns, whereas the lowest alachlor decay rates were observed under cooler, aerobic, oligotrophic water conditions. Similar relationships were observed for metolachlor, although metolachlor decay rates were about 40% slower. Our data suggest that herbicides will decay rapidly in waters that are high in nutrients possibly resulting from human activities. Alternately, low nutrient or pristine waters will have the lowest rates of herbicide decay. On a policy level, all efforts should be made to prevent exposure of comparatively pristine waters to herbicide inputs.