Advertisement

Benzotriazoles in the Aquatic Environment: a Review of Their Occurrence, Toxicity, Degradation and Analysis

  • M. D. Alotaibi
  • A. J. McKinley
  • B. M. Patterson
  • A. Y. Reeder
Article

Abstract

Benzotriazoles (BTs) are an emerging class of environmental pollutants used in a wide range of industrial applications. Benzotriazole (BTri) and 5-methylbenzotriazole (5-MeBT) have recently been detected in water supplies around the world, and are thus attracting the attention of many environmental researchers. The focus of this review is on assessing contemporary methods to detect BTs using high-performance liquid chromatography (HPLC), and providing information regarding their occurrence, degradation and toxicity within the environment.

Keywords

Benzotriazole 5-methylbenzotriazole Occurrence Toxicity Degradation Analysis 

Notes

Acknowledgments

The support of the King Abdullah Scholarship Program (KASP) and King Saud University scholarship program is gratefully appreciated. The constructive comments and suggestions by CSIRO reviewers to improve the quality of this paper are also acknowledged.

References

  1. Alotaibi, M. D., Patterson, B. M., McKinley, A. J., Reeder, A. Y., & Furness, A. J. (2015a). Benzotriazole and 5-methylbenzotriazole in recycled water, surface water and dishwashing detergents from Perth, Western Australia: analytical method development and application. Environmental Science: Processes and Impacts, 17, 448–457.Google Scholar
  2. Alotaibi, M. D., Patterson, B. M., McKinley, A. J., Reeder, A. Y., Furness, A. J., & Donn, M. J. (2015b). Fate of benzotriazole and 5-methylbenzotriazole in recycled water recharged into an anaerobic aquifer: Column studies. Water Research, 70, 184–195.CrossRefGoogle Scholar
  3. Andreozzi, R., Caprio, V., Insola, A., & Longo, G. (1998). Photochemical degradation of benzotriazole in aqueous solution. Journal of Chemical Technology and Biotechnology, 73, 93–98.CrossRefGoogle Scholar
  4. Asimakopoulos, A. G., Bletsou, A. A., Wu, Q., Thomaidis, N. S., & Kannan, K. (2012). Determination of benzotriazoles and benzothiazoles in human urine by liquid chromatography-tandem mass spectrometry. Analytical Chemistry, 85, 441–448.CrossRefGoogle Scholar
  5. Asimakopoulos, A. G., Ajibola, A., Kannan, K., & Thomaidis, N. S. (2013a). Occurrence and removal efficiencies of benzotriazoles and benzothiazoles in a wastewater treatment plant in Greece. Science of the Total Environment, 452, 163–171.CrossRefGoogle Scholar
  6. Asimakopoulos, A. G., Wang, L., Thomaidis, N. S., & Kannan, K. (2013b). Benzotriazoles and benzothiazoles in human urine from several countries: A perspective on occurrence, biotransformation, and human exposure. Environment International, 59, 274–281.CrossRefGoogle Scholar
  7. Barr, D. P., & Aust, S. D. (1994). Mechanisms white-rot fungi use to degrade pollutants. Journal of Environmental Science and Technology, 28, A78–A87.CrossRefGoogle Scholar
  8. Bi, E., Schmidt, T. C., Haderlein, S. B. (2006). Sorption of heterocyclic organic compounds to reference soils: column studies for process identification. Environmental Science and Technology, 40, 5962–5970.Google Scholar
  9. Bi, E., Zhang, L., Schmidt, T. C., Haderlein, S. B. (2009). Simulation of nonlinear sorption of N-heterocyclic organic contaminates in soil columns. Journal of Contaminant Hydrology, 107, 58–65.Google Scholar
  10. Breedveld, G.D., Børresen, M., Roseth, R. (2002). Degradation of airport contaminants in a soil based treatment plant. In Proceedings of the First European Bioremediation Conference. Chania, Crete, Greece, pp. 5–20.Google Scholar
  11. Breedveld, G. D., Roseth, R., Sparrevik, M., Hartnik, T., & Hem, L. J. (2003). Persistence of the de-icing additive benzotriazole at an abandoned airport. Water, Air, & Soil Pollution: Focus, 3, 91–101.CrossRefGoogle Scholar
  12. Bronner, G., Goss, K. U. (2010). Sorption of organic chemicals to soil organic matter: influence of soil variability and pH dependence. Environmental Science and Technology, 45, 1307–1312.Google Scholar
  13. Burke, V., Treumann, S., Duennbier, U., Greskowiak, J., Massmann, G. (2013). Sorption behavior of 20 wastewater originated micropollutants in groundwater - Column experiments with pharmaceutical residues and industrial agents. Journal of Contaminant Hydrology, 154, 29–41.Google Scholar
  14. Cancilla, D. A., Holtkamp, A., Matassa, L., & Fang, X. (1997). Isolation and characterization of Microtox®-active components from aircraft de-icing/anti-icing fluids. Environmental Toxicology and Chemistry, 16, 430–434.CrossRefGoogle Scholar
  15. Cancilla, D. A., Martinez, J., & van Aggelen, G. C. (1998). Detection of aircraft de-icing/anti-icing fluid additives in a perched water monitoring well at an international airport. Journal of Environmental Science and Technology, 32, 3834–3835.CrossRefGoogle Scholar
  16. Cancilla, D. A., Baird, J. C., Geis, S. W., & Corsi, S. R. (2003a). Studies of the environmental fate and effect of aircraft deicing fluids: detection of 5-methyl-1H-benzotriazole in the fathead minnow (Pimephales promelas). Environmental Toxicology and Chemistry, 22, 134–140.CrossRefGoogle Scholar
  17. Cancilla, D. A., Baird, J. C., & Rosa, R. (2003b). Detection of aircraft deicing additives in groundwater and soil samples from Fairchild Air Force Base, a small to moderate user of deicing fluids. Bulletin of Environmental Contamination and Toxicology, 70, 0868–0875.CrossRefGoogle Scholar
  18. Capdevila, C., Moukha, S., Ghyczy, M., Theilleux, J., Gelie, B., Delattre, M., Corrieu, G., & Asther, M. (1990). Characterization of peroxidase secretion and subcellular organization of Phanerochaete-Chrysosporium INA-12 in the presence of various soybean phospholipid fractions. Applied and Environmental Microbiology, 56, 3811–3816.Google Scholar
  19. Castro, S., Davis, L. C., & Erickson, L. E. (2001). Plant-enhanced remediation of glycol-based aircraft deicing fluids. Practice Periodical of Hazardous, Toxic, Waste Management, 5, 141.CrossRefGoogle Scholar
  20. Castro, S., Davis, L. C., & Erickson, L. E. (2005). Natural, cost-effective, and sustainable alternatives for treatment of aircraft deicing fluid waste. Environmental Progress, 24, 26–33.CrossRefGoogle Scholar
  21. Chen, W. G., Dai, J. J., Wang, X. F., Fang, S. (2010). The UV Protection of Polyester Fabrics Dyed with Benzotriazole UV-absorbers, Textile Bioengineering and Informatics Society Ltd, Textile Bioengineering and Informatics Symposium Proceedings, Hong Kong Sar. 1-3.Google Scholar
  22. Cheng, C., Phipps, D., Alkhaddar, R. M. (2006). Investigation of Changes in the Microbial Community During the Biodegradation of Benzotriazole.Google Scholar
  23. Cornell, J. (2001). The environmental impact of 4(5)-methylbenzotriazole from aircraft deicing operations. Dissertation, Department of Civil, Environmental and Architectural Engineering, University of Colorado.Google Scholar
  24. Cornell, J. S., Pillard, D. A., & Hernandez, M. T. (2000). Comparative measures of the toxicity of component chemicals in aircraft deicing fluid. Environmental Toxicology and Chemistry, 19, 1465–1472.CrossRefGoogle Scholar
  25. Corsi, S. R., Zitomer, D. H., Field, J. A., & Cancilla, D. A. (2003). Nonylphenol ethoxylates and other additives in aircraft deicers, antiicers, and waters receiving airport runoff. Journal of Environmental Science and Technology, 37, 4031–4037.CrossRefGoogle Scholar
  26. Corsi, S. R., Geis, S. W., Loyo-Rosales, J. E., & Rice, C. P. (2006a). Aquatic toxicity of nine aircraft deicer and anti-icer formulations and relative toxicity of additive package ingredients alkylphenol ethoxylates and 4,5-methyl-1H-benzotriazoles. Journal of Environmental Science and Technology, 40, 7409–7415.CrossRefGoogle Scholar
  27. Corsi, S. R., Geis, S. W., Loyo-Rosales, J. E., Rice, C. P., Sheesley, R. J., Failey, G. G., & Cancilla, D. A. (2006b). Characterization of aircraft deicer and anti-icer components and toxicity in airport snowbanks and snowmelt runoff. Journal of Environmental Science and Technology, 40, 3195–3202.CrossRefGoogle Scholar
  28. de Alda, M. J. L., & Barcelo, D. (2001). Review of analytical methods for the determination of estrogens and progestogens in waste waters. Fresenius Journal of Analytical Chemistry, 371, 437–447.CrossRefGoogle Scholar
  29. Dummer, N. M. (2014). 4(5)-Methylbenzotriazole: a review of the life-cycle of an emerging contaminant. Reviews in Environmental Science and Biotechnology, 13, 53–61.CrossRefGoogle Scholar
  30. Eddy, M. (2003). Wastewater engineering: treatment and reuse. New York: McGraw-Hill.Google Scholar
  31. Fawell, J., & Ong, C. N. (2012). Emerging contaminants and the implications for drinking water. International Journal of Water Resources Development, 28, 247–263.CrossRefGoogle Scholar
  32. Ferrer, I., & Thurman, E. M. (2003). Liquid chromatography/time-of-flight/mass spectrometry (LC/TOF/MS) for the analysis of emerging contaminants. TrAC, Trends in Analytical Chemistry, 22, 750–756.CrossRefGoogle Scholar
  33. Focazio, M. J., Kolpin, D. W., Barnes, K. K., Furlong, E. T., Meyer, M. E. T., Zaugg, S. D., Barber, L. B., & Thurman, M. E. (2008). A national reconnaissance for pharmaceuticals and other organic wastewater contaminants in the United States—II. Untreated drinking water sources. Science of the Total Environment, 402, 201–216.CrossRefGoogle Scholar
  34. Giger, W. (2009). Hydrophilic and amphiphilic water pollutants: using advanced analytical methods for classic and emerging contaminants. Analytical and Bioanalytical Chemistry, 393, 37–44.CrossRefGoogle Scholar
  35. Giger, W., Schaffner, C., & Kohler, H.-P. E. (2006). Benzotriazole and tolyltriazole as aquatic contaminants. 1. Input and occurrence in rivers and lakes. Journal of Environmental Science and Technology, 40, 7186–7192.CrossRefGoogle Scholar
  36. Giri, R. R., Ozaki, H., Ota, S., Takanami, R., & Taniguchi, S. (2010). Degradation of common pharmaceuticals and personal care products in mixed solutions by advanced oxidation techniques. International Journal of Environmental Science and Technology, 7, 251–260.CrossRefGoogle Scholar
  37. Gomes, R. L., Lester, J. N. (2003). In Endocrine disrupters in wastewater and sludge treatment processes,219-266, USA.Google Scholar
  38. Gomes, R. L., Scrimshaw, M. D., & Lester, J. N. (2003). Determination of endocrine disrupters in sewage treatment and receiving waters. TrAC, Trends in Analytical Chemistry, 22, 697–707.CrossRefGoogle Scholar
  39. Graham, R. D. (1986). Induction of male sterility in wheat using organic ligands with high specificity for binding copper. Euphytica, 35, 621–629.CrossRefGoogle Scholar
  40. Gruden, C. L., Dow, S. M., & Hernandez, M. T. (2001). Fate and toxicity of aircraft deicing fluid additives through anaerobic digest ion. Water Environment Research, 73, 72–79.CrossRefGoogle Scholar
  41. Hagedorn, B., Larsen, M., Dotson, A. (2013). First Assessment of Triazoles and Other Organic Contaminants in Snow and Snowmelt in Urban Waters, Anchorage, Alaska,97-104.Google Scholar
  42. Halket, J. M., & Zaikin, V. G. (2003). Derivatization in mass spectrometry—1. Silylation. European Journal of Mass Spectrometry, 9, 1–21.CrossRefGoogle Scholar
  43. Harris, C. A., Routledge, E. J., Schaffner, C., Brian, J. V., Giger, W., & Sumpter, J. P. (2007). Benzotriazole is antiestrogenic in vitro but not in vivo. Environmental Toxicology and Chemistry, 26, 2367–2372.CrossRefGoogle Scholar
  44. Hart, D. S., Davis, L. C., Erickson, L. E., & Callender, T. M. (2004). Sorption and partitioning parameters of benzotriazole compounds. Microchemical Journal, 77, 9–17.CrossRefGoogle Scholar
  45. Hartwell, S. I., Jordahl, D. M., Evans, J. E., & May, E. B. (1995). Toxicity of aircraft de-icer and anti-icer solutions to aquatic organisms. Environmental Toxicology and Chemistry, 14, 1375–1386.CrossRefGoogle Scholar
  46. Hem, L. J., Weideborg, M., & Schram, E. (2000). Degradation and toxicity of additives to aircraft de-icing fluids: the effect of discharge of such fluids to municipal wastewater treatment plants. Proceedings of Water Environment Federal, 2000, 419–433.CrossRefGoogle Scholar
  47. Hem, L. J., Hartnik, T., Roseth, R., & Breedveld, G. D. (2003). Photochemical degradation of benzotriazole. Journal of Environmental Science and Health, Part A Environmental Science, 38, 471–481.CrossRefGoogle Scholar
  48. Hernández, F., Pozo, Ó. J., Sancho, J. V., López, F. J., Marín, J. M., & Ibáñez, M. (2005). Strategies for quantification and confirmation of multi-class polar pesticides and transformation products in water by LC-MS2 using triple quadrupole and hybrid quadrupole time-of-flight analyzers. TrAC, Trends in Analytical Chemistry, 24, 596–612.CrossRefGoogle Scholar
  49. Hollender, J., Singer, H., McArdell, C. S. (2008). Polar Organic Micropollutants In The Water Cycle (103-116) Springer: Netherlands.Google Scholar
  50. Hollingsworth, J., Sierra-Alvarez, R., Zhou, M., Ogden, K. L., Field, J. A. (2005). Anaerobic biodegradability and methanogenic toxicity of key constituents in copper chemical mechanical planarization effluents of the semiconductor industry. Chemosphere, 59, 1219–1228.Google Scholar
  51. Hopfgartner, G., Varesio, E., Tschäppät, V., Grivet, C., Bourgogne, E., & Leuthold, L. A. (2004). Triple quadrupole linear ion trap mass spectrometer for the analysis of small molecules and macromolecules. Journal of Mass Spectrometry, 39, 845–855.CrossRefGoogle Scholar
  52. Jafvert, C. T. (1990). Sorption of organic acid compounds to sediments: initial model development. Environmental Toxicology and Chemistry, 9, 1259–1268.CrossRefGoogle Scholar
  53. Janna, H., Scrimshaw, M. D., Williams, R. J., Churchley, J., & Sumpter, J. P. (2011). From dishwasher to tap? Xenobiotic substances benzotriazole and tolyltriazole in the environment. Journal of Environmental Science and Technology, 45, 3858–3864.CrossRefGoogle Scholar
  54. Jia, Y., Bakken, L. R., Breedveld, G. D., Aagaard, P., & Frostegard, A. (2006). Organic compounds that reach subsoil may threaten groundwater quality: effect of benzotriazole on degradation kinetics and microbial community composition. Soil Biology and Biochemistry, 38, 2543–2556.CrossRefGoogle Scholar
  55. Jia, Y., Breedveld, G. D., & Aagaard, P. (2007a). Column studies on transport of deicing additive benzotriazole in a sandy aquifer and a zerovalent iron barrier. Chemosphere, 69, 1409–1418.CrossRefGoogle Scholar
  56. Jia, Y., Molstad, L., Frostegard, A., Aagaard, P., Breedveld, G. D., & Bakken, L. R. (2007b). Kinetics of microbial growth and degradation of organic substrates in subsoil as affected by an inhibitor, benzotriazole: model based analyses of experimental results. Soil Biology and Biochemistry, 39, 1597–1608.CrossRefGoogle Scholar
  57. Jover, E., Matamoros, V., & Bayona, J. M. (2009). Characterization of benzothiazoles, benzotriazoles and benzosulfonamides in aqueous matrixes by solid-phase extraction followed by comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry. Journal of Chromatography. A, 1216, 4013–4019.CrossRefGoogle Scholar
  58. Kadar, E., Dashfield, S., & Hutchinson, T. (2010). Developmental toxicity of benzotriazole in the protochordate, Ciona intestinalis (Chordata, Ascidiae). Analytical and Bioanalytical Chemistry, 396, 641–647.CrossRefGoogle Scholar
  59. Kazanskii, L. P., & Selyaninov, I. A. (2010). XPES of 1,2,3-benzotriazole nanolayers formed on iron surface. Protection of Metals and Physical Chemistry of Surfaces, 46, 797–804.CrossRefGoogle Scholar
  60. Kim, J.-W., Ramaswamy, B. R., Chang, K.-H., Isobe, T., & Tanabe, S. (2011a). Multiresidue analytical method for the determination of antimicrobials, preservatives, benzotriazole UV stabilizers, flame retardants and plasticizers in fish using ultra high performance liquid chromatography coupled with tandem mass spectrometry. Journal of Chromatography. A, 1218, 3511–3520.CrossRefGoogle Scholar
  61. Kim, J. W., Chang, K. H., Isobe, T., & Tanabe, S. (2011b). Acute toxicity of benzotriazole ultraviolet stabilizers on freshwater crustacean (Daphnia pulex). Journal of Toxicological Sciences, 36, 247–251.CrossRefGoogle Scholar
  62. Kiss, A., & Fries, E. (2009). Occurrence of benzotriazoles in the rivers Main, Hengstbach, and Hegbach (Germany). Environmental Science and Pollution Research International, 16, 702–710.CrossRefGoogle Scholar
  63. Kiss, A., & Fries, E. (2012). Seasonal source influence on river mass flows of benzotriazoles. Journal of Environmental Monitoring, 14, 697–703.CrossRefGoogle Scholar
  64. Kolpin, D. W., Furlong, E. T., Meyer, M. E. T., Thuman, M. E., Zaugg, S. D., Barber, L. B., & Buxton, H. T. (2002). Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999–2000: a national reconnaissance. Environmental Science and Technology, 36, 1202–1211.CrossRefGoogle Scholar
  65. Kuznetsov, Y., Agafonkina, M., Andreeva, N., & Solov’eva, A. (2010). Modification of iron surface by dimegin and adsorption of 1,2,3-benzotriazole. Protection of Metals and Physical Chemistry of Surfaces, 46, 743–747.CrossRefGoogle Scholar
  66. Lin, A. Y.-C., & Reinhard, M. (2005). Photodegradation of common environmental pharmaceuticals and estrogens in river water. Environmental Toxicology and Chemistry, 24, 1303–1309.CrossRefGoogle Scholar
  67. Liu, Y.-S., Ying, G.-G., Shareef, A., & Kookana, R. S. (2011a). Biodegradation of three selected benzotriazoles under aerobic and anaerobic conditions. Water Research, 45, 5005–5014.CrossRefGoogle Scholar
  68. Liu, Y. S., Ying, G. G., Shareef, A., & Kookana, R. S. (2011b). Photolysis of benzotriazole and formation of its polymerised photoproducts in aqueous solutions under UV irradiation. Environmental Chemistry, 8, 174–181.CrossRefGoogle Scholar
  69. Liu, Y. S., Ying, G. G., Shareef, A., & Kookana, R. S. (2011c). Simultaneous determination of benzotriazoles and ultraviolet filters in ground water, effluent and biosolid samples using gas chromatography-tandem mass spectrometry. Journal of Chromatography. A, 1218, 5328–5335.CrossRefGoogle Scholar
  70. Liu, Y. S., Ying, G. G., Shareef, A., & Kookana, R. S. (2012). Occurrence and removal of benzotriazoles and ultraviolet filters in a municipal wastewater treatment plant. Environmental Pollution, 165, 225–232.CrossRefGoogle Scholar
  71. Liu, Y.-S., Ying, G.-G., Shareef, A., & Kookana, R. S. (2013). Biodegradation of three selected benzotriazoles in aquifer materials under aerobic and anaerobic conditions. Journal of Contaminant Hydrology, 151, 131–139.CrossRefGoogle Scholar
  72. Loos, R., Locoro, G., Comero, S., Contini, S., Schwesig, D., Werres, F., Balsaa, P., Gans, O., Weiss, S., Blaha, L., Bolchi, M., & Gawlik, B. M. (2010). Pan-European survey on the occurrence of selected polar organic persistent pollutants in ground water. Water Research, 44, 4115–4126.CrossRefGoogle Scholar
  73. Loi, C. H., Busetti, F., Linge, K .L., Joll, C. A. (2013). Development of a solid-phase extraction liquid chromatography tandem mass spectrometry method for benzotriazoles and benzothiazoles in wastewater and recycled water. Journal of Chromatography. A, 1299, 48–57.Google Scholar
  74. Madani, S. M., Ehteshamzadeh, M., & Rafsanjani, H. H. (2010). Investigation of the microstructure and corrosion performance of a nanostructured titania-containing hybrid silicate film on mild steel. Thin Solid Films, 519, 145–150.CrossRefGoogle Scholar
  75. Malhas, R. N., Al-Awadi, N. A., & El-Dusouqui, O. M. E. (2007). Kinetics and mechanism of gas-phase pyrolysis of N-aryl-3-oxobutanamide ketoanilides, their 2-arylhydrazono derivatives, and related compounds. International Journal of Chemical Kinetics, 39, 82–91.CrossRefGoogle Scholar
  76. Matamoros, V., Jover, E., & Bayona, J. M. (2010a). Occurrence and fate of benzothiazoles and benzotriazoles in constructed wetlands. Water Science and Technology, 61, 191–198.CrossRefGoogle Scholar
  77. Matamoros, V., Jover, E., & Bayona, J. M. (2010b). Part-per-trillion determination of pharmaceuticals, pesticides, and related organic contaminants in river water by solid-phase extraction followed by comprehensive two-dimensional gas chromatography time-of-flight mass spectrometry. Analytical Chemistry, 82, 699–706.CrossRefGoogle Scholar
  78. McNeill, K., & Cancilla, D. (2009). Detection of triazole deicing additives in soil samples from airports with low, mid, and large volume aircraft deicing activities. Bulletin of Environmental Contamination and Toxicology, 82, 265–269.CrossRefGoogle Scholar
  79. Molins-Delgado, D., Díaz-Cruz, M., & Barceló, S. D. (2015). Removal of polar UV stabilizers in biological wastewater treatments and ecotoxicological implications. Chemosphere, 119, S51–S57.CrossRefGoogle Scholar
  80. Nakata, H., Murata, S., & Filatreau, J. (2009). Occurrence and concentrations of benzotriazole UV stabilizers in marine organisms and sediments from the Ariake Sea, Japan. Journal of Environmental Science and Technology, 43, 6920–6926.CrossRefGoogle Scholar
  81. Neamţu, M., & Frimmel, F. H. (2006). Photodegradation of endocrine disrupting chemical nonylphenol by simulated solar UV-irradiation. Science of the Total Environment, 369, 295–306.CrossRefGoogle Scholar
  82. NRMMC (2008). Australian Guidelines for Water Recycling Augmentation of Drinking Water Supplies, Natural Resource Management Ministerial Council, Environment Protection and Heritage Council, and National Health and Medical Research Council, Adelaide.Google Scholar
  83. O'Brien, I. Z. (2002). Biotransformation potential and uncoupling behavior of common benzotriazole-based corrosion inhibitors. Dissertation, Department of Civil, Environmental and Architectural Engineering, University of Colorado.Google Scholar
  84. Pervova, M., Kirichenko, V., & Saloutin, V. (2010). Determination of 1,2,3-benzotriazole in aqueous solutions and air by reaction-gas-liquid chromatography. Journal of Analytical Chemistry, 65, 276–279.CrossRefGoogle Scholar
  85. Pillard, D. A., Cornell, J. S., DuFresne, D. L., & Hernandez, M. T. (2001). Toxicity of benzotriazole and benzotriazole derivatives to three aquatic species. Water Research, 35, 557–560.CrossRefGoogle Scholar
  86. Puttanna, K., Gowda, N. M. N., & Rao, E. (1999). Effect of concentration, temperature, moisture, liming and organic matter on the efficacy of the nitrification inhibitors benzotriazole, o-nitrophenol, m-nitroaniline and dicyandiamide. Nutrient Cycling in Agroecosystems, 54, 251–257.CrossRefGoogle Scholar
  87. Rajak, H., Lanjhiyana, S. K., Kumar, P., Thakur, B. S., Gupta, A. K., & Kharya, M. D. (2011). Synthesis and antimicrobial evaluation of some benzotriazole-substituted-1,3,4-thiadiazoles. Indian Journal of Heterocyclic Chemistry, 20, 229–232.Google Scholar
  88. Rao, N. L. (1996). Patent no. 5503775. United States of America.Google Scholar
  89. Reemtsma, T., Weiss, S., Mueller, J., Petrovic, M., González, S., Barcelo, D., Ventura, F., & Knepper, T. P. (2006). Polar pollutants entry into the water cycle by municipal wastewater: a European perspective. Journal of Environmental Science and Technology, 40, 5451–5458.CrossRefGoogle Scholar
  90. Reemtsma, T., Miehe, U., Duennbier, U., & Jekel, M. (2010). Polar pollutants in municipal wastewater and the water cycle: occurrence and removal of benzotriazoles. Water Research, 44, 596–604.CrossRefGoogle Scholar
  91. Richardson, S. D., & Ternes, T. A. (2011). Water analysis: emerging contaminants and current issues. Analytical Chemistry, 83, 4614–4648.CrossRefGoogle Scholar
  92. Sahar, E., Ernst, M., Godehardt, M., Hein, A., Herr, J., Kazner, C., Melin, T., Cikurel, H., Aharoni, A., Messalem, R., Brenner, A., & Jekel, M. (2011). Comparison of two treatments for the removal of selected organic micropollutants and bulk organic matter: conventional activated sludge followed by ultrafiltration versus membrane bioreactor. Water Science and Technology, 63, 733–740.CrossRefGoogle Scholar
  93. Scheurer, M., Storck, F. R., Graf, C., Brauch, H. J., Ruck, W., Lev, O., & Lange, F. T. (2011). Correlation of six anthropogenic markers in wastewater, surface water, bank filtrate, and soil aquifer treatment. Journal of Environmental Monitoring, 13, 966–973.CrossRefGoogle Scholar
  94. Seeland, A., Oetken, M., Kiss, A., Fries, E., & Oehlmann, J. (2012). Acute and chronic toxicity of benzotriazoles to aquatic organisms. Environmental Science and Pollution Research, 19, 1781–1790.CrossRefGoogle Scholar
  95. Sills, R. C., Hailey, J. R., Neal, J., Boorman, G. A., Haseman, J. K., & Melnick, R. L. (1999). Examination of low-incidence brain tumor responses in F344 rats following chemical exposures in national toxicology program carcinogenicity studies. Toxicologic Pathology, 27, 589–599.CrossRefGoogle Scholar
  96. Sorahan, T. (2009). Cancer risks in chemical production workers exposed to 2-mercaptobenzothiazole. Occupational and Environmental Medicine, 66, 269–273.CrossRefGoogle Scholar
  97. Stasinakis, A. S., Thomaidis, N. S., Arvaniti, O. S., Asimakopoulos, A. G., Samaras, V. G., Ajibola, A., Mamais, D., & Lekkas, T. D. (2013). Contribution of primary and secondary treatment on the removal of benzothiazoles, benzotriazoles, endocrine disruptors, pharmaceuticals and perfluorinated compounds in a sewage treatment plant. Science of the Total Environment, 463–464, 1067–1075.CrossRefGoogle Scholar
  98. Ternes, T., & von Gunten, U. (2010). Editorial to special issue in water research: emerging contaminants in water. Water Research, 44, 351–351.CrossRefGoogle Scholar
  99. Ternes, T. A., Andersen, H., Gilberg, D., & Bonerz, M. (2002). Determination of estrogens in sludge and sediments by liquid extraction and GC/MS/MS. Analytical Chemistry, 74, 3498–3504.CrossRefGoogle Scholar
  100. Ternes, T. A., Stüber, J., Herrmann, N., McDowell, D., Ried, A., Kampmann, M., & Teiser, B. (2003). Ozonation: a tool for removal of pharmaceuticals, contrast media and musk fragrances from wastewater? Water Research, 37, 1976–1982.CrossRefGoogle Scholar
  101. Tham, P. T., & Kennedy, K. J. (2005). Fate of tolyltriazoles and nonylphenol ethoxylates in upflow anaerobic sludge blanket reactors. Journal of Environmental Engineering ASCE, 131, 892–900.CrossRefGoogle Scholar
  102. USEPA (2011). High Production Volume (HPV) Challenge Program, United State Environmental Protection Agency, Washington. Available: http://www.epa.gov/hpv/.
  103. van Leerdam, J. A., Hogenboom, A. C., van der Kooi, M. M. E., & de Voogt, P. (2009). Determination of polar 1H-benzotriazoles and benzothiazoles in water by solid-phase extraction and liquid chromatography LTQ FT orbitrap mass spectrometry. International Journal of Mass Spectrometry, 282, 99–107.CrossRefGoogle Scholar
  104. Vetter, W., Lorenz, J. (2012). Determination of benzotriazoles in dishwasher tabs from Germany and estimation of the discharge into German waters. Environmental Science and Pollution Research, 1-6.Google Scholar
  105. Voutsa, D., Hartmann, P., Schaffner, C., & Giger, W. (2006). Benzotriazoles, alkylphenols and bisphenol a in municipal wastewaters and in the Glatt river, Switzerland. Environmental Science and Pollution Research, 13, 333–341.CrossRefGoogle Scholar
  106. Wan, J., Yan, X., Ma, C. P., Bi, S., & Zhu, H. L. (2010). Synthesis, structure characterization, and biological evaluation of some new 1,2,3-benzotriazole derivatives. Medicinal Chemistry Research, 19, 970–983.CrossRefGoogle Scholar
  107. Wang, L., Asimakopoulos, A. G., Moon, H.-B., Nakata, H., & Kannan, K. (2013). Benzotriazole, benzothiazole, and benzophenone compounds in indoor dust from the United States and East Asian Countries. Journal of Environmental Science and Technology, 47, 4752–4759.CrossRefGoogle Scholar
  108. Weiss, S., & Reemtsma, T. (2005). Determination of benzotriazole corrosion inhibitors from aqueous environmental samples by liquid chromatography-electrospray ionization-tandem mass spectrometry. Analytical Chemistry, 77, 7415–7420.CrossRefGoogle Scholar
  109. Weiss, S., Jakobs, J., & Reemtsma, T. (2006). Discharge of three benzotriazole corrosion inhibitors with municipal wastewater and improvements by membrane bioreactor treatment and ozonation. Journal of Environmental Science and Technology, 40, 7193–7199.CrossRefGoogle Scholar
  110. Wu, X., Chou, N., Lupher, D., Davis, L.C. (1998). Benzotriazoles: Toxicity And Degradation. In Proceedings of the 1998 Conference on Hazardous Waste Research. Kansas State University Manhattan: Kansas, USA, pp. 337-384.Google Scholar
  111. Xu, B., Wu, F., Zhao, X., & Liao, H. (2010). Benzotriazole removal from water by Zn-Al-O binary metal oxide adsorbent: behavior, kinetics and mechanism. Journal of Hazardous Materials, 184, 147–155.CrossRefGoogle Scholar
  112. Yamamoto, H., Nakamura, Y., Moriguchi, S., Nakamura, Y., Honda, Y., Tamura, I., Hirata, Y., Hayashi, A., & Sekizawa, J. (2009). Persistence and partitioning of eight selected pharmaceuticals in the aquatic environment: laboratory photolysis, biodegradation, and sorption experiments. Water Research, 43, 351–362.CrossRefGoogle Scholar
  113. Yang, B., Ying, G. G., Zhang, L. J., Zhou, L. J., Liu, S., & Fang, Y. X. (2011). Kinetics modeling and reaction mechanism of ferrate(VI) oxidation of benzotriazoles. Water Research, 45, 2261–2269.CrossRefGoogle Scholar
  114. Yargeau, V., & Leclair, C. (2008). Impact of operating conditions on decomposition of antibiotics during ozonation: a review. Ozone Science and Engineering, 30, 175–188.CrossRefGoogle Scholar
  115. Yu, L., Fink, G., Wintgens, T., Melin, T., Ternes, T. A. (2009). Sorption behavior of potential organic wastewater indicators with soils. Water Research, 43, 951–960.Google Scholar
  116. Zhang, Z., Ren, N., Li, Y.-F., Kunisue, T., Gao, D., & Kannan, K. (2011). Determination of benzotriazole and benzophenone UV filters in sediment and sewage sludge. Journal of Environmental Science and Technology, 45, 3909–3916.CrossRefGoogle Scholar
  117. Zwiener, C., & Frimmel, F. (2004). LC-MS analysis in the aquatic environment and in water treatment technology—a critical review. Analytical and Bioanalytical Chemistry, 378, 862–874.CrossRefGoogle Scholar

Copyright information

© Her Majesty the Queen in Right of Australia as represented by: Bradley Patterson 2015

Authors and Affiliations

  • M. D. Alotaibi
    • 1
    • 2
    • 3
  • A. J. McKinley
    • 1
  • B. M. Patterson
    • 1
    • 2
  • A. Y. Reeder
    • 4
  1. 1.School of Chemistry and BiochemistryUniversity of Western AustraliaCrawleyAustralia
  2. 2.CSIRO Land and waterPerthWestern Australia
  3. 3.Department of Plant Production, College of Food and Agricultural SciencesKing Saud UniversityRiyadhSaudi Arabia
  4. 4.Centre for Microscopy, Characterization and AnalysisUniversity of Western AustraliaCrawleyAustralia

Personalised recommendations