Abstract
The effect of β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) upon the photochemically-induced fluorescence (PIF) properties of four phenylurea herbicides, including linuron, diuron, isoproturon and neburon has been studied. Photochemical conversion of these nonfluorescent herbicides into strongly fluorescent photoproducts was shown to occur in β-CD and HP-β-CD aqueous media. The influence of pH, UV irradiation time and photoproduct stability on the fluorescence intensity was also investigated. In addition, the stoichiometry and formation constants of the complexes formed between herbicides and β-cyclodextrin (β-CD) or 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) were determined. The formation constant values, ranging from 184 ± 40 to 1498 ± 245 M-1, were calculated by applying the iterative nonlinear regression (NLR) approach to the PIF data. Linear calibrations graphs were established in the interval 1–12 μg/mL, for diuron, linuron and neburon. The IUPAC limits of detection ranged between 580 and 700 ng/mL, according to the compound. Application to the analysis of phenylurea herbicides in spiked river water was also described.
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References
J. Szejtli: Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest (1982).
I. Duran-Meras, A. Muñoz de la Peña, F. Salinas and I. Rodriguez-Caceres: Analyst 119, 1215 (1994).
Y.-B. Jiang: Spectrochim. Acta 51, 275 (1995).
S. Spcypinski and L. Cline-Love: Anal. Chem. 56, 72 (1994).
A. Muñoz de la Peña, M.C. Mahedero and A. Bautista-Sanchez: Analusis 28, 670 (2000).
L. Flamigni: J. Chem. Soc. Faraday Trans. 90, 2331 (1994).
T. Tsuki, F. Hirayama and K. Vekama: J. Chem. Soc. Perkin Trans. 2, 109 (1993).
P. Bortolus and S. Monti: J. Phys. Chem. 91, 5046 (1987).
M. Maafi, B. Laassis, J.J. Aaron, M.C. Mahedero, A. Muñoz de la Peña and F. Salinas: J. Incl. Phenom. Mol. Recogn. Chem. 22, 235 (1995).
M. Maafi, J.J. Aaron and C. Lion: J. Incl. Phenom. Mol. Recogn. Chem. 30, 227 (1998).
J.C. Marquez, M. Hernandez and F. Garcia-Sanchez: Analyst 115, 1003 (1990).
S. Panadero, A. Gomez-Hens and D. Perez-Bendijo: Talanta 40, 225 (1993).
F. Garcia-Sanchez, M. Cedazo, J. Louillo and A. Navas-Dias: Talanta 43, 1327 (1996).
A. Coly and J.J. Aaron: Anal. Chim. Acta 360, 129 (1998).
D. Splenger and B. Hamroll: J. Chromatogr. 49, 205 (1970).
F.S. Tanaka and R.G. Wien: J. Chromatogr. 87, 85 (1973).
D.G. Sounders and L.E. Vanatta: Anal. Chem. 46, 1319 (1974).
D.G. Glad, Th. Popoff and O. Theander: J. Chromatogr. 16, 118 (1978).
D.Z. Bradway and T. Shafik: J. Chromatogr. 15, 322 (1977).
C. Miles: J. Chromatogr. 592, 283 (1992).
B.M. Patel, M.A. Moye and R. Weinberger: Talanta 38, 913 (1991).
D. Barcelo: J. Chromatogr. 643, 117 (1973).
A. Coly and J.J. Aaron: Talanta 46, 815 (1998).
A. Coly and J.J. Aaron: Analyst 119, 1205 (1994).
S. Eremin, B. Laassis and J.J. Aaron: Talanta 43, 295 (1996).
J.L. Vilchez, R. El-Khattabi, R. Blanc and A. Navalon: Anal. Chim. Acta 371, 247 (1998).
A. Coly and J.J. Aaron: Analusis 24, 107 (1996).
C.J. Miles and M.A. Moye: Anal. Chem. 60, 220 (1988).
L.F. Garcia, S. Eremin and J.J. Aaron: Anal. Lett. 29, 1447 (1996).
J.W. Birks and R.W. Frei: Trends Anal. Chem. 1, 361 (1982).
J.J. Aaron: in S.G. Schulman (ed.), Molecular Luminescence Spectroscopy: Methods and Applications, Wiley, New York (1993), p. 85.
J. Szejtli: Cyclodextrin Technology, Kluwer Academic Publishers, Boston (1988).
J.J. Aaron, B. Laassis, M.C. Mahedero, A. Muñoz de la Peña and F. Salinas: J. Incl. Phenom. Mol. Recogn. Chem. 18, 69 (1994).
M.C. Mahedero, A. Muñoz de la Peva, A. Bautista-Sanchez and J.J. Aaron: Luminescence 15, 103 (2000).
M. Maafi, K. Taha-Bouamri, A. Bautista-Sanchez, J.J. Aaron, M.C. Mahedero, A. Muñoz de la Peña and F. Salinas: Biomed. Chromatogr. 13, 189 (1999).
A. Bautista, J.J. Aaron, M.C. Mahedero and A. Muñoz de la Peña: Analusis 27, 857 (1999).
T.A. Albanis, D.G. Hela, T.M. Sakellirides and I.K. Konstantinou: J. Chromatogr. A 823, 59 (1998).
I. Ferrer and D. Barcelo: J. Chromatogr. A 737, 93 (1996).
M.C. Gennaro, C. Abrigo, D. Giacosa, L. Rigotti and A. Liberatori: J. Chromatogr. A 718, 81 (1995).
D. Barcelo, G. Duirand, R.J. Vreeken, G.L. de Jong and U.A.Th. Brinkman: Anal. Chem. 62, 1696 (1991).
C. Lacorte, C. Molina and D. Barcelo: Anal. Chim. Acta 81, 71 (1993).
D. Kotzias and F. Korte: Ecotoxicol. Environ. Saf. 5, 503 (1981).
P.H. Mazzocchi and M.P. Rao: J. Agric. Food Chem. 20, 957 (1972).
R.G. Lutchefeld: J. Chromatogr. Sci. 23, 516 (1985).
K.A. Connors: Binding Constants, the Measurement of Molecular Complex Stability, Wiley, New York (1987).
C.R. Worthing: The Pesticide Manual, 8th edn, The British Crop Protection Council (1987).
C. deLiñan Vicente: Farmacologia Vegetal, Ediciones Agrotécnicas, S.L. (1997).
P. Yúferan and C. Domíen: Quimica Agricola 2. Plaguicidas y Fitorreguladores Ed. Alhambra Universidad (1990).
L. Cuadros Rodriguez, A.M. Garcia Campaña, C. Jimenez Linares and M. Roman Ceba: Anal. Lett. 28, 1243 (1993).
C.A. Clayton, J.W. Hines and P.D. Elkins: Anal. Chem. 59, 2506 (1987).
L.A. Currie: Anal. Chim. Acta 391, 105 (1999).
Analytical Methods Commitee: Analyst 113, 469 (1998).
Nomenclature, Symbols, Units and their Usage in Spectrochemical Analysis II: Spectrochim. Acta B 33, 242 (1978).
A.M. Garcia Campaña, L. Cuadros Rodriguez, F. Alex Barrero, M. Roman Ceba and J.L. Sierra Fernandez: Trends Anal. Chem. 16, 381 (1997).
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Mahedero, M.C., Muñoz De La Peña, A., Bautista, A. et al. An Investigation of Inclusion Complexes of Cyclodextrins with Phenylurea Herbicides by Photochemically-Induced Fluorescence. Analytical Applications. Journal of Inclusion Phenomena 42, 61–70 (2002). https://doi.org/10.1023/A:1014523521684
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DOI: https://doi.org/10.1023/A:1014523521684