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Characterization of Aqueous and Solid Inclusion Complexes of Diuron and Isoproturon with -Cyclodextrin

Volume 58, Number 6 (June 2004) Page 711-718

Dupuy, N.; Marquis, S.; Vanhove, G.; Bria, M.; Kister, J.; Vrielynck, L.

The interaction of diuron and isoproturon herbicides with β-cyclodextrin is conducive to the formation of inclusion compounds in aqueous solution as well as in the solid state. The physico-chemical study of these complexes was carried out by various analytical techniques such as ultraviolet (UV), Fourier transform infrared (FT-IR), Raman, X-ray diffraction, and 1H-NMR (nuclear magnetic resonance) spectroscopies. The existence of inclusion complexes in water solution between the β-cyclodextrin and each of the herbicides was revealed by electronic absorption and 1H-NMR spectroscopies. A 1:1 stoichiometry was determined for both complexes in aqueous medium from UV absorption spectra by using the Benesi-Hildebrand method; the relative stability constants at room temperature were calculated at 2700 ± 300 L mol-1 and 750 ± 50 L mol-1 for isoproturon and diuron, respectively. In the solid state, inclusion processes with β-cyclodextrin were characterized by means of infrared and Raman techniques and confirmed by X-ray diffraction spectra.