In the last century, agricultural intensification on the Canadian prairies has resulted in increased pesticide use with the potential to expose non-target organisms to pesticides as a result of non-point source pollution. In order to minimize risk and implement programs and regulations that promote sustainable agricultural practices, information on the types of pesticides being used and their subsequent fate in soils is essential. In this study, pesticide use trends were summarized and Herbicide Risk Indicators (HRIs) were calculated for the 1996-2006 growing seasons; a time period in which genetically modified herbicide-tolerant (GMHT) crops were commercially adopted. This study also quantified the influence of soil moisture, temperature, slope position, and soil depth within the plough layer on 2,4-D [2,4-(dichlorophenoxy) acetic acid] fate in soil obtained from a cultivated undulating field in Southern Manitoba. Annual pesticide use varied slightly over the 11-year period, but overall, there were no significant increasing or decreasing temporal trends for herbicides, fungicides, or insecticides. Although the total mass of herbicides remained relatively consistent, there was a significant change in the types of herbicides applied associated with the increased adoption of GMHT-canola; the most significant trend being the increase of GLY, from 16% to 45% of the total herbicides used in 1996 to 2006, respectively. HRIs demonstrated that herbicides used in 2006, are on average, more soluble, but less persistent, less volatile, and less acutely toxic to mammals (inhalation and acceptable daily intake), aquatic invertebrates, fish and algae, than those applied in 1996. Although 2,4-D remains one of the top 10 herbicides applied to agricultural crops in Manitoba, there were no significant increasing or decreasing trends in 2,4-D use between 1996 and 2006. Results from the experimental studies revealed that 2,4-D mineralization half-lives (DT50) in soil varied from 3 days to 51 days with the total 2,4-D mineralization (MT) ranging from 5.8 to 50.9%, depending on soil moisture, temperature, slope position, and depth. Both DT50 and MT demonstrated a polynomial relationship with temperature, typical of a biological system with minimum, optimum, and maximum temperatures.