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Herein, we designed two fluorescent Tetrasubstituted Benzene sulfonyl appended Thiacalix[4]arene receptors named PK1–2 which sensitively and selectively detect Sulfosulfuron among other herbicides and pesticides. The detection limit (LOD) was found to be 0.21 ppm and 0.35 ppm, and the Enhancement constant (Ks) was determined 7.07 X 104 M− 1 and 5.55 X 104 M− 1 for PK1 and PK2 respectively. Using the Non-linear regression method, the Association constant was obtained as 2.1 X 104 M− 1 and 2.23 X 104 M− 1 whereas the binding ratio was found to be 1:1 for both PK1–2 respectively. Additionally, the interference studies show the selective nature of receptors for Sulfosulfuron among its sulfonylurea family. To further confirm the binding mechanism computational investigation was carried out, which validates the 1:1 binding ratio. The receptors were found to be recyclable in nature with simple Acid-Base treatment. This new approach of using Supramolecules as fluorescent probes for sensitive and selective detection of herbicides are rare in the literature.