Dichlobenil is an extensively used herbicide worldwide which is transformed to the mobile 2,6-dichlorobenzamide (BAM) in soil. BAM has been found in many European groundwater resources that are exploited for drinking water. Currently, immunoassay based monitoring technique (plate based ELISA) is being employed to quantitatively detect BAM in water samples. In this work, as a starting step of developing immunoassay based on-site monitoring systems for pesticide analysis, the heterogeneous BAM immunoassay is optimised in terms of surface (polymer) regeneration. We have synthesised a small library of BAM haptens which are slightly different in chemical structures, immobilised them on surfaces and compared the affinity constants of the monoclonal antibody HYB 273 towards them. By using ELISA technology, we also have checked the regeneration potentials of the haptens, correlated these results to the affinity constants and found that BAM hapten with an intermediate affinity has better regeneration potential.