Abstract
A medium-pressure mercury lamp, emitting strongly in the 200–400 nm range was applied for the degradation of 3,5,6-trichloro-2-pyridinol (TCP), a hydrolysis product of chlorpyrifos. Photodegradation of TCP in aqueous solution exhibited pseudo-first order kinetics with a rate constant that was wavelength dependent and increased below 300 nm. The TCP degradation rate and quantum yield increased with solution pH up to a constant maximum value of (6.40 ± 0.046) × 10−3 cm2 mJ− 1 and 0.178 ± 0.002 mol E−1 respectively, at pH 5 and above. Addition of 5 mg L− 1 H2O2 to generate OH radicals led to an increase in removal rates by a factor of 1.5. Addition of phosphate buffer resulted in decreased photolysis at 3 < pH < 6.
Similar content being viewed by others
References
Armbrust, K. L.: 2001, ‘Chlorothalonil and chlorpyrifos degradation products in golf course leachate’, Pest Manage. Sci. 57(9), 797–802.
Bakiamoh, S. B., Maimait, R. and McGowin, A. E.: 1999, ‘Supercritical fluid extraction of chlorpyrifos and 3,5,6-trichloro-2-pyridinol from garden compost’, J. Chromatogr. A. 862, 105–112.
Barcelo, D., Durand, G. and De Bertrand, N.: 1993, ‘Photodegradation of the organophosphorus pesticides chlorpyrifos, fenamiphos and vamidothion in water’, Toxicol. Environ. Chem. 38(3/4), 183–199.
Barron, M. G. and Woodburn, K. B.: 1995, ‘Ecotoxicity of chlorpyrifos’, Rev. Environ. Contam. Toxicol. 144, 1–94.
Baskaran, S., Kookana, R. S. and Naidu, R.: 2003, ‘Contrasting behaviour of Chlorpyrifos and its primary metabolite TCP (3,5,6-trichloro-2-pyridinol), with depth in soil profiles’, J. Agric. Food Chem. 51(7), 749–760.
Bolton, J. R. and Linden, K. G.: 2003, ‘Standardization of methods for fluence (UV dose) determination in bench-scale UV experiments’, ASCE Journal of Env. Eng. 129(3), 209–215.
Cabras, P. and Plumitallo, A.: 1991, ‘High performance liquid-chromatographic separation of fenthion and its metabolites’, J. Chromatogr. 540(1/2), 406–419.
Dilling, W. L., Lickly, L. C., Lickly, T. M., Murphy, P. G. and McKellar, R. L.: 1984, ‘Organic photochemistry. 19. Quantum yields for O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) phosphorothioate (chlorpyrifos) and 3,5,6-trichloro-2-pyridinol in dilute aqueous solutions and their environmental phototransformation rates’, Environ. Sci. Technol. 18(7), 540–543.
Doong, R. A., Chen, C. H., Maithreepala, R. A. and Chang, S. M.: 2001, ‘The influence of pH and cadmium sulfide on the photocatalytic degradation of 2-chlorophenol in titanium dioxide suspensions’, Wat. Res. 35(12), 2873–2880.
Hirahara, Y., Ueno, H. and Nakamuro, K.: 2001, ‘Comparative photodegradation study of fenthion and disulfoton under irradiation of different light sources in liquid- and solid-phases’, J. Health Sci. 47(2), 129–135.
Hong, F., Yin Win, K. and Pehkonen, P. O.: 2001, ‘Hydrolysis of terbufos using simulated Environmental Conditions: Rates, mechanisms, and product analysis’, J. Agric. Food Chem. 49, 5866–5873.
Fasani, E., Mella, M., Monti, S. and Albini, A.: 2001, ‘Unexpected photoreactions of some 7-amino-6-fluoroquinolones in phosphate buffer’, Eur. J. Org. Chem. 2, 391–397.
Jans, U. and Miah, M. H.: 2003, ‘Reaction of chlorpyrifos-methyl in aqueous hydrogen sulfide/bisulfide solutions’, J. Agric. Food Chem. 51, 1956–1960.
Ku, Y., Chang, J. L. and Cheng, S. C.: 1998, ‘Effect of solution pH on the hydrolysis and photolysis of diazinon in aqueous solution’, Water Air Soil Poll. 108(3/4), 445–456.
Magnuson, M. L., Kelty, C. A., Sharpless, C. M., Linden, K. G., Fromme, W., Metz, D. H. and Kashinkunti, R.: 2003, ‘Effect of UV irradiation on organic matter extracted from treated Ohio river water studied through the use of electrospray mass spectrometry’, Environ. Sci. Technol. 36(23), 5252–5260.
Ohashi, N., Tsuchiya, Y., Sasano, T. and Hamada, A.: 1994, ‘Ozonation products of organophosphorus pesticides in water’, Jpn. J. Toxicol. Environ. Health. 40, 185–192.
Petty, D. G., Skogerboe, J. G., Getsinger, K. D., Foster, D. R., Houtman, B. A., Fairchild, J. F. and Anderson, L. W.: 2001, ‘The aquatic fate of triclopyr in whole-pond treatments’, Pest Manage. Sci. 57(9), 764–777.
Racke, K. D.: 1993, ‘Environmental fate of chlorpyrifos’, Rev. Environ. Contam. Toxicol. 131, 1–154.
Sharpless, C. M., Seibold, D. A. and Linden, K. G.: 2003, ‘Nitrate photosensitized degradation of atrazine during UV water treatment’, Aquat. Sci. 65, 359–366.
Sharpless, C. M. and Linden, K. G.: 2003, ‘Experimental and model comparisons of low- and medium-pressure Hg lamps for the direct and H2O2 assisted UV photodegradation of N-Nitrosodimethylamine in simulated drinking water’, Environ. Sci. Technol. 37(9), 1933–1940.
Vasudevan, D., Dorley, P. J. and Zhuang, X.: 2001, ‘Adsorption of hydroxyl pyridines and quinolines at the metal oxide-water interface: Role of tautomeric equilibrium’, Environ. Sci. Technol. 35(10), 2006–2013.
Wan, H. B., Wong, M. K. and Mok, C. Y.: 1994, ‘Comarative study on the quantum yields of direct photolysis of organophosphorus pesticides in aqueous solution’, J. Agric. Food Chem. 42, 2625–2630.
Zhang, Q. and Pehkonen, S. O.: 1999, ‘Oxidation of diazinon by aqueous chlorine: Kinetics, mechanisms, and product studies’, J. Agric. Food Chem. 47, 1760–1766.
Zhang, Z. L., Hong, H. S., Zhou, J. L. and Yu, G.: 2002, ‘Occurrence and behavior of organophosphorus insecticides in the River Wuchuan, southeast China’, J. Environ. Monit. 4(4), 498–504.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Shemer, H., Sharpless, C.M. & Linden, K.G. Photodegradation of 3,5,6-trichloro-2-pyridinol in aqueous solution. Water Air Soil Pollut 168, 145–155 (2005). https://doi.org/10.1007/s11270-005-0960-z
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11270-005-0960-z