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Regional groundwater vulnerability maps to indicate the impact of leaching of chemicals under different management scenarios were prepared for the Rattaphum Catchment using several leaching models and GIS techniques. The Attenuation Factor (AF) model was used to simulate the leaching potential of several pesticides for selected soils in the catchment under different rates of recharge from irrigation. The LEACHN model was used to simulate the NO3− leaching potential and LEACHP was used to simulate leaching potential of metolachlor under different management scenarios. The results showed that only a small number of pesticides have the potential to contaminate the shallow groundwater. However, the risk of contamination with nutrients is much higher due to the mobility and conservative nature of the NO3−. The LEACHP results indicated that the intensive use of agrochemicals in the vegetable growing area, especially during the rainy season when the groundwater is near the surface, increases the risk of pesticide contamination. The results of upscaling from the farm to the catchment scale using soil maps and GIS techniques under various management scenarios and chemical application rates showed that the most effective strategy to reduce chemical leaching is by reducing pesticide application rates and optimizing the application of irrigation water. The identification of potential high risk farms by ranking soils and agricultural practices could be used to formulate management practices that reduce pesticide contamination of the surface and ground water resources in the area.