Preemergent herbicides are commonly applied to control many annual weed species in turfgrass systems. Oxadiazon and prodiamine are pre-emergent herbicides that effectively inhibit the growth of emerging annual grasses and broadleaf weeds without harming certain turfgrass species. However, in recent years, a decline in the efficacy of oxadiazon and prodiamine has been observed by golf course managers, leading to an increase in application rates in an attempt to mitigate the issue. Therefore, the objective of this study was to characterize degradation processes that affect oxadiazon and prodiamine persistence and efficacy in order to identify solutions or mitigation strategies. Soil samples were collected from unique sites throughout North Carolina. Field studies were organized as a randomized complete block design containing 3 replications and 2 experimental runs. Treatments were arranged in a split-split plot design, where the whole plots consisted of 4 sites with histories of continuous oxadiazon or prodiamine use (never applied, applied 1-2 years, ~7 years, > 15 years), the sub-plots were 2 treatments (non-sterilized and sterilized), and the sub-sub-plots were 6 collection timings (14, 28, 42, 56, 112, and 168 days after treatment). Herbicide residue quantifications were determined using high-performance liquid chromatography. Data were recorded and converted into a percentage of the applied rate. A higher percent of oxadiazon was observed for sterilized soil (79.2%) compared to non-sterilized soil (73.7%). In the non-sterilized soil, at 14 DAT there were no differences between periods of use. However, at 28 DAT, the soil with no use history presented a higher percentage of oxadiazon (83.0%) compared to 1 and 15 years (75.5%, and 77.1% respectively). Furthermore, at 42 and 56 DAT, the soil with no history of application exhibited the highest percentage of oxadiazon among all periods of use. Findings of this study suggest that there is higher concentration of oxadiazon, meaning less degradation, in the soils with no history of application.