Environmental Significance of the Diclofop-methyl and Cyclodextrin Inclusion Complexes

Cyclodextrins (CDs) possess a hydrophilic external surface and a hydrophobic cavity. They are thus highly soluble and, in the meantime, effectively form inclusion complexes with hydrophobic organic compounds to enhance their solubilities. In this study, the complexation between modified β-CDs and the herbicide diclofop-methyl (DM), (2-(4-(2,4-dichlorophenoxy)-phenoxy) propionate), was investigated. The complexation was confirmed by the shifts in the wavelengths of maximum ultra violet (UV) absorption and fluorescence excitation/emission. The deuterium isotope effects indicate that in the presence of β-CDs the solubility of DM was lower while that of diclofop was higher in D₂O than in H₂O, suggesting the primary role of hydrophobic interactions in complexation. The solubility of DM was enhanced in the presence of β-CDs, the extent of which depended on the modification of β-CDs. The complexation reduced the hydrolysis of DM and hence increased its stability. The small inconsistency in the power of β-CDs between hydrolysis retardation and solubilization suggests that hydrolysis was affected by the properties of β-CDs and the configuration of DM in the complexes. Use of β-CDs may thus result in the mobilization of soil DM. Properly modified β-CDs may be utilized as formulation additives for improved delivery of DM and for enhanced environmental remediation.