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Soil Sorption and Degradation Studies of Pharmaceutical Compounds Present in Recycled Wastewaters Based on Enantiomeric Fractionation

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Interaction and Fate of Pharmaceuticals in Soil-Crop Systems

Part of the book series: The Handbook of Environmental Chemistry ((HEC,volume 103))

Abstract

Wastewater (WW) reuse and biosolid application for vegetable crop culture is a practice applied worldwide. This strategy helps mitigate the pressure on water resources and improve the fertility of soil. Wastewater reuse is currently not included in chemical risk assessment, but its application has risk of potential accumulation of contaminants of emerging concern such as pharmaceutical active compounds (PhACs). In fact, this practice has caused the uptake of PhACs by plant and their subsequent entrance on the food chain. Residual quantities of contaminants may enter in soil, and they can be accumulated or percolated, consequently leading to contamination of groundwater. Herein, we report the main factors that play an important role on the accumulation of PhACs in soil after irrigation with treated wastewater. Limited data is actually available on the fate of PhACs in field studies because several processes are in competition for their dissipation including sorption and formation of non-extractable residues, leaching, as well as biotransformation. Consequently, an approach based on enantiomeric fractionation of chiral PhACs has been suggested to discriminate between biotic and abiotic dissipation processes.

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References

  1. Israel Ministry of Finance (2018) The Water Sector

    Google Scholar 

  2. Lees K, Fitzsimons M, Snape J, Tappin A, Comber S (2016) Pharmaceuticals in soils of lower countries: physico-chemical fate and risks from wastewater irrigation. Environ Int 94:712–723

    CAS  Google Scholar 

  3. Bixio D, Thoeye C, De Koning J, Joksimovic D, Savic D, Wintgens T, Melin T (2006) Wastewater reuse in Europe. Desalination 187:89–101

    CAS  Google Scholar 

  4. Iglesias R, Ortega E, Batanero G, Quintas L (2010) Water reuse in Spain: data overview and costs estimation of suitable treatment trains. Desalination 263:1–10

    CAS  Google Scholar 

  5. Yi L, Jiao W, Chen X, Chen W (2011) An overview of reclaimed water reuse in China. J Environ Sci 23:1585–1593

    Google Scholar 

  6. Latare AM, Kumar O, Singh SK, Gupta A (2014) Direct and residual effect of sewage sludge on yield, heavy metals content and soil fertility under rice–wheat system. Ecol Eng 69:17–24

    Google Scholar 

  7. Vaish B, Sarkar A, Singh P, Singh PK, Sengupta C, Singh RP (2016) Prospects of biomethanation in Indian urban solid waste: stepping towards a sustainable future. In: Karthikeyan OP, Heimann K, Muthu SS (eds) Recycling of solid waste for biofuels and bio-chemicals. Springer, Singapore, pp 1–29

    Google Scholar 

  8. Carden DE, Walker DJ, Flowers TJ, Miller AJ (2003) Single-cell measurements of the contributions of cytosolic Na+ and K+ to salt tolerance. Plant Physiol 131:676–683

    CAS  Google Scholar 

  9. Aucejo A, Burguet MC, Munoz R, Marques JL (1995) Densities viscosities, and refractive indices of some n-alkane binary liquid systems at 298.15K. J Chem Eng Data 40:141–147

    CAS  Google Scholar 

  10. Noshadi I, Salahi A, Hemmati M, Rekabdar F, Mohammadi T (2013a) Experimental and ANFIS modelling for fouling analysis of oily wastewater treatment using ultrafiltration. Asia Pac J Chem Eng 8:527–538

    CAS  Google Scholar 

  11. Assouline S, Narkis K (2013) Effect of long-term irrigation with treated wastewater on the root zone environment. Vadose Zone J 12(2):vzj2012.0216

    Google Scholar 

  12. Assouline S, Russo D, Silber A, Or D (2015) Balancing water scarcity and quality for sustainable irrigated agriculture. Water Resour Res 51:3419–3436

    Google Scholar 

  13. Bardhan G, Russo D, Goldstein D, Levy GJ (2016) Changes in the hydraulic properties of a clay soil under long-term irrigation with treated wastewater. Geoderma 264:1–9

    CAS  Google Scholar 

  14. Levy GJ, Assouline S (2010) Physical aspects. In: Levy GJP, Fine P, Bar-Tal A (eds) Treated wastewater in agriculture: use and impacts on the soil environment and crops. Wiley-Blackwell, Oxford, pp 306–327

    Google Scholar 

  15. Noshadi M, Fahandej S, Sepaskhah AR (2013b) Effects of salinity and irrigation water management in soil and tomato in drip irrigation. Int J Plant Prod 7:1735–6814

    Google Scholar 

  16. Schacht K, Marschner B (2015) Treated wastewater irrigation effects on soil hydraulic conductivity and aggregate stability of loamy soils in Israel. J Hydrol Hydromech 63:47–54

    Google Scholar 

  17. Benotti MJ, Snyder SA (2009) Pharmaceuticals and endocrine disrupting compounds: implications for ground water replenishment with recycled water. Ground Water 47:499–502

    CAS  Google Scholar 

  18. Boxall AB, Johnson P, Smith EJ, Sinclair CJ, Stutt E, Levy LS (2006) Uptake of veterinary medicines from soils into plants. J Agric Food Chem 54:2288–2297

    CAS  Google Scholar 

  19. Kinney CA, Furlong ET, Werner SL, Cahill D (2006) Presence and distribution of wastewater-derived pharmaceuticals in soil irrigated with reclaimed water. Environ Toxicol Chem 25:317–326

    CAS  Google Scholar 

  20. Wu X, Dodgen LK, Conkle JL, Gan J (2015) Plant uptake of pharmaceutical and personal care products from recycled water and biosolids: a review. Sci Total Environ 536:655–666

    CAS  Google Scholar 

  21. Kasprzyk-Hordern B, Dinsdale RM, Guwy AJ (2009) The removal of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs during wastewater treatment and its impact on the quality of receiving waters. Water Res 43:363–380

    CAS  Google Scholar 

  22. Ayers RS, Westcot DW (eds) (1985) Water quality for irrigation. FAO, Rome

    Google Scholar 

  23. Chefetz B, Mualem T, Ben-Ari J (2008) Sorption and mobility of pharmaceutical compounds in soil irrigated with reclaimed wastewater. Chemosphere 73:1335–1343

    CAS  Google Scholar 

  24. Siemens J, Huschek G, Siebe C, Kaupenjohann M (2008) Concentrations and mobility of human pharmaceuticals in the world’s largest wastewater irrigation system, Mexico City-Mezquital Valley. Water Res 42:2124–2134

    CAS  Google Scholar 

  25. Biel-Maeso M, Corada-Fernández C, Lara-Martín PA (2018) Monitoring the occurrence of pharmaceuticals in soils irrigated with reclaimed wastewater. Environ Pollut 235:312–321

    CAS  Google Scholar 

  26. Li J, Dodgen L, Ye Q, Gan J (2014) Degradation and transformation products of acetaminophen in soil. Water Res 49:44–52

    CAS  Google Scholar 

  27. Corada-Fernández C, Jiménez-Martínez J, Candela L, González-Mazo E, Lara-Martín PA (2015) Occurrence and spatial distribution of emerging contaminants in the unsaturated zone. Case study: Guadalete River basin (Cadiz, Spain). Chemosphere 119:s131–s137

    Google Scholar 

  28. Dalkmann P, Broszat M, Siebe C, Willaschek E, Sakinc T, Huebner J, Amelung W, Grohmann E, Siemens J (2012) Accumulation of pharmaceuticals, enterococcus, and resistance genes in soils irrigated with wastewater for zero to 100 years in Central Mexico. PLoS One 7(9):e45397

    CAS  Google Scholar 

  29. Christou A, Karaolia P, Hapeshi E, Michael C, Fatta-Kassinos D (2017) Long-term wastewater irrigation of vegetables in real agricultural systems: concentration of pharmaceuticals in soil, uptake and bioaccumulation in tomato fruits and human health risk assessment. Water Res 109:24–34

    CAS  Google Scholar 

  30. Facey SJ, Nebel BA, Kontny L, Allgaier M, Hauer B (2018) Rapid and complete degradation of diclofenac by native soil microorganisms. Environ Technol Innov 10:55–61. https://doi.org/10.1016/j.eti.2017.12.009

    Article  Google Scholar 

  31. Durán-Alvarez JC, Becerril-Bravo E, Silva Castro V, Jiménez B, Gibson R (2009) The analysis of a group of acidic pharmaceuticals, carbamazepine, and potential endocrine disrupting compounds in wastewater irrigated soils by gas chromatography–mass spectrometry. Talanta 78:1159–1166

    Google Scholar 

  32. Vulava VM, Cory WC, Murphey VL, Ulmer CZ (2016) Sorption, photodegradation, and chemical transformation of naproxen and ibuprofen in soils and water. Sci Total Environ 565:1063–1070

    CAS  Google Scholar 

  33. Gibson R, Durán-Alvarez JC, Estrada KL, Chávez A, Cisneros BJ (2010) Accumulation and leaching potential of some pharmaceuticals and potential endocrine disruptors in soils irrigated with wastewater in the Tula Valley, Mexico. Chemosphere 81:1437–1445

    CAS  Google Scholar 

  34. Grossberger A, Hadar Y, Borch T, Chefetz B (2014) Biodegradability of pharmaceutical compounds in agricultural soils irrigated with treated wastewater. Environ Pollut 185:168–177

    CAS  Google Scholar 

  35. Koda O, Golovko O, Kodešová R, Klement A, Grabic R (2016) Transformation of atenolol, metoprolol, and carbamazepine in soils: the identification, quantification, and stability of the transformation products and further implications for the environment. Environ Pollut 218:574–585

    Google Scholar 

  36. Li J, Dodgen L, Ye Q, Gan J (2013) Degradation kinetics and metabolites of carbamazepine in soil. Environ Sci Technol 47:3678–3684

    CAS  Google Scholar 

  37. Martínez-Hernández V, Meffe R, López SH, de Bustamante I (2016) The role of sorption and biodegradation in the removal of acetaminophen, carbamazepine, caffeine, naproxen and sulfamethoxazole during soil contact: a kinetic study. Sci Total Environ 559:232–241

    Google Scholar 

  38. Koba O, Golovko O, Kodešová R, Fér M, Grabic R (2017) Antibiotics degradation in soil: a case of clindamycin, trimethoprim, sulfamethoxazole and their transformation products. Environ Pollut 220:1251–1263. https://doi.org/10.1016/j.envpol.2016.11.007

    Article  CAS  Google Scholar 

  39. Girardi C, Greve J, Lamshöft M, Fetzer I, Miltner A, Schäffer A, Kästner M (2011) Biodegradation of ciprofloxacin in water and soil and its effects on the microbial communities. J Hazard Mater 198:22–30

    CAS  Google Scholar 

  40. Butler E, Whelan MJ, Sakrabani R, van Egmond R (2012) Fate of triclosan in field soils receiving sewage sludge. Environ Pollut 167:101–109

    CAS  Google Scholar 

  41. Biel-Maeso M, González-González C, Lara-Martín PA, Corada-Fernández C (2019) Sorption and degradation of contaminants of emerging concern in soils under aerobic and anaerobic conditions. Sci Total Environ 666:662–671

    CAS  Google Scholar 

  42. Gielen GC, van den Heuvel MR, Clinton PW, Greenfield LG (2009) Factors impacting on pharmaceutical leaching following sewage application to land. Chemosphere 74:537–542

    CAS  Google Scholar 

  43. Paz A, Tadmor G, Malchi T, Blotevogel J, Borch T, Polubesova T, Chefetz B (2016) Fate of carbamazepine, its metabolites, and lamotrigine in soils irrigated with reclaimed wastewater: sorption, leaching and plant uptake. Chemosphere 160:22–29

    CAS  Google Scholar 

  44. Borgman O, Chefetz B (2013) Combined effects of biosolids application and irrigation whit reclaimed wastewater on transport of pharmaceuticals compounds in arable soils. Water Res 47:3431–3443

    CAS  Google Scholar 

  45. Lau CH-F, Tien YC, Stedtfeld RD, Topp E (2020) Impacts of multi-year field exposure of agricultural soil to macrolide resistance genes and selected mobile genetic elements. Sci Total Environ 559:232–241

    Google Scholar 

  46. Coogan MA, Edziyie RE, La Point TW, Venables BJ (2007) Algal bioaccumulation of triclocarban, triclosan and methyl-triclosan in a North Texas wastewater treatment plant receiving stream. Chemosphere 67:1911–1918

    CAS  Google Scholar 

  47. Tolls J (2001) Sorption of veterinary pharmaceuticals in soils: a review. Environ Sci Technol 35:3397–3406

    CAS  Google Scholar 

  48. Xu J, Wu L, Chang AC (2009) Degradation and adsorption of selected pharmaceuticals and personal care products (PPCPs) in agricultural soils. Chemosphere 77:1299–1305

    CAS  Google Scholar 

  49. Thelusmond JR, Kawka E, Strathmann TJ, Cupples AM (2018) Diclofenac, carbamazepine and triclocarban biodegradation in agricultural soils and the microorganisms and metabolic pathways affected. Sci. Total Environ 640–640:1393–1410

    Google Scholar 

  50. Pan M, Chu LM (2016) Adsorption and degradation of five selected antibiotics in agricultural soil. Sci Total Environ 545-546:48–56

    CAS  Google Scholar 

  51. Doretto KM, Peruchi LM, Rath S (2014) Sorption and desorption of sulfadimethoxine, sulfaquinoxaline and sulfamethazine antimicrobials in Brazilian soils. Sci Total Environ (476–477):406–414

    Google Scholar 

  52. Loffler D, Rombke J, Meller M, Ternes TA (2005) Environmental fate of pharmaceuticals in water/sediment systems. Environ Sci Technol 39:5209–5218

    Google Scholar 

  53. Roberts TR (1984) Non-extractable pesticide residues in soils and plants. Pure Appl Chem 56(7):945–956

    Google Scholar 

  54. Loffler D, Hatz A, Albrecht D, Fligg M, Hogeback J, Ternes TA (2020) Determination of non-extractable residues in soils: towards a standardised approach. Environ Pollut 259:113826

    Google Scholar 

  55. Schäffer A, Kästner M, Trapp S (2018) A unified approach for including non-extractable residues (NER) of chemicals and pesticides in the assessment of persistence. Environ Sci Eur 30:51

    Google Scholar 

  56. Kästner M, Trapp S, Schaeffer A (2018) Consultancy service to support ECHA in improving the interpretation of non-extractable residues (NER) in degradation assessment. Discussion paper-final report

    Google Scholar 

  57. Barriuso E, Benoit P, Dubus IG (2008) Formation of pesticides nonextractable (bound) residues in soil: magnitude, controlling factors and reversibility. Environ Sci Technol 42(6):1845–1854

    CAS  Google Scholar 

  58. Li Y, Sallach J-B, Zhang W, Boyd S, Li H (2019) Insight into the distribution of pharmaceuticals in soil-water-plant systems. Water Res 152:38–46

    CAS  Google Scholar 

  59. Li H, Lee LS, Fabrega JR, Jafvert CT (2001) Role of pH in partitioning and cation exchange of aromatic amines on water-saturated soils. Chemosphere 44:627–635

    CAS  Google Scholar 

  60. Bi E, Schmidt TC, Haderlein SB (2006) Sorption of heterocyclic organic compounds to reference soils: column studies for process identification. Environ Sci Technol 40:5962–5970

    CAS  Google Scholar 

  61. Guangyao S, Yaning Y, Minsheng H, Kai Y (2005) Influence of pH on pesticide sorption by soil containing wheat residue-derived char. Environ Pollut 134:457–463

    Google Scholar 

  62. Holten Lützhøft HC, Vaes WHJ, Halling-Sørensen B, Hermens JLM (2000) Influence of pH and other modifying factors on the distribution behavior of 4-quinolones to solid phases and humic acids studied by “negligible-depletion” SPME-HPLC. Environ Sci Technol 34:4989–4994

    Google Scholar 

  63. Franco A, Fu W, Trapp S (2009) Influence of soil pH on the sorption of ionizable chemicals: modelling advances. Environ Toxicol Chem 28:458–464

    CAS  Google Scholar 

  64. Vazquez-Roig P, Andreu V, Blasco C, Picó Y (2012) Risk assessment on the presence of pharmaceuticals in sediments, soils and waters of the Pego-Oliva Marshlands (Valencia, eastern Spain). Sci Total Environ 440:24–32

    CAS  Google Scholar 

  65. Vasudevan D, Bruland GL, Torrance BS, Upchurch VG, MacKay AA (2009) pH-dependent ciprofloxacin sorption to soils: interaction mechanisms and soil factors influencing sorption. Geoderma 151:68–76

    CAS  Google Scholar 

  66. Zhang Y-L, Lin S-S, Dai C-M, Shi L, Zhou X-F (2014) Sorption-desorption and transport of trimethoprim and sulfanamide antibiotics in agricultural soil: effect of soil type, dissolved organic matter, and pH. Environ Sci Pollut Res 21:5827–5835

    CAS  Google Scholar 

  67. Bekçi Z, Seki Y, Yurdakoç MK (2006) Equilibrium studies for trimethoprim adsorption on montmorillonite KSF. J Hazard Mat B 133:233–242

    Google Scholar 

  68. Tülp HC, Fenner K, Schwarzenbach RP, Goss KU (2009) pH-dependent sorption of acid organic chemicals to soil organic matter. Environ Sci Technol 43:9189–9195

    Google Scholar 

  69. Hyun S, Lee LS (2004) Factors controlling sorption of prosulfuron by variable charge soils and model sorbents. J Environ Qual 33:1354–1361

    CAS  Google Scholar 

  70. Liu X, Zhang H, Luo Y, Zhu R, Wang H, Huang B (2020) Sorption of oxytetracycline in particulate organic matter in soils and sediments: roles of pH, ionic strength and temperature. Sci Total Environ 714:136628

    CAS  Google Scholar 

  71. Cox L, Velarde P, Cabrera A, Hermosin MC, Cornejo J (2007) Dissolved organic carbon interactions whit sorption and leaching of diuron in organic amended soils. Eur J Soil Sci 58(3):714–721

    CAS  Google Scholar 

  72. Leenheer JA (1981) Comprehensive approach to preparative isolation and fractionation of dissolved organic carbon from natural waters and wastewaters. Environ Sci Technol 15(5):578–587

    CAS  Google Scholar 

  73. Ilani T, Schulz E, Chefetz B (2005) Interactions of organic compounds with wastewater dissolved organic matter: role of hydrophobic fractions. J Environ Qual 34:552–562

    CAS  Google Scholar 

  74. Maoz A, Chefetz B (2010) Sorption of the pharmaceuticals carbamazepine and naproxen to dissolved organic matter: role of structural fractions. Water Res 44:981–989

    CAS  Google Scholar 

  75. Carmosini N, Lee LS (2009) Ciprofloxacin sorption by dissolved organic carbon from reference and bio-waste materials. Chemosphere 77:813–820

    CAS  Google Scholar 

  76. Buerge I, Kasteel R, Bächli A, Poiger T (2019a) Behavior of the chiral herbicide imazamox in soils: enantiomer composition differentiates between biodegradation and photodegradation. Environ Sci Technol 53:5733–5740

    CAS  Google Scholar 

  77. Gulkowska A, Buerge IJ, Poiger T, Kasteel R (2016) Time-dependent sorption of two novel fungicides in soils within a regulatory framework. Pest Manag Sci 72:2218–2230

    CAS  Google Scholar 

  78. Buerge I, Bächli A, Kasteel R, Portmann R, Lopez-Cabeza R, Schwarb L, Poiger T (2019b) Behavior of the chiral herbicide imazamox in soils: pH-dependent, enantioselective degradation, formation and degradation of several chiral metabolites. Environ Sci Technol 53:5725–5732

    CAS  Google Scholar 

  79. Elsner M, Imfeld G (2016) Compound-specific isotope analysis (CSIA) of micropollutants in the environment – current developments and future challenges. Curr Opin Biotechnol 41:60–72

    CAS  Google Scholar 

  80. Maiers M, Prasse C, Pati S, Nitsche S, Li Z, Radke M, Meyer A, Hofstetter T, Ternes T, Elsner M (2016) Exploring trends of C and N isotope fractionation to trace transformation reactions of diclofenac in natural and engineered systems. Environ Sci Technol 50:10933–10942

    Google Scholar 

  81. Kunkel U, Radke M (2012) Fate of pharmaceuticals in rivers: deriving a benchmark dataset at favorable attenuation conditions. Water Res 46:5551–5565

    CAS  Google Scholar 

  82. Gamiz B, Facenda G, Celis R (2016) Evidence for the effect of sorption enantioselectivity on the availability of chiral pesticide enantiomers in soil. Environ Pollut 213:966–973

    CAS  Google Scholar 

  83. Jammer S, Gelman F, Lev O (2016) Applicability of the Rayleigh equation for enantioselective metabolism of chiral xenobiotics by microsomes, hepatocytes and in-vivo retention in rabbit tissues. Sci Rep 6:23715

    CAS  Google Scholar 

  84. Jammer S, Voloshenko A, Gelman F, Lev O (2014) Chiral and isotope analyses for assessing the degradation of organic contaminants in the environment: Rayleigh dependence. Environ Sci Technol 48:3310–3318

    CAS  Google Scholar 

  85. Jin B, Rolle M (2016) Joint interpretation of enantiomer and stable isotope fractionation for chiral pesticides degradation. Water Res 105:178–186

    CAS  Google Scholar 

  86. Gasser G, Pankratov I, Elhanany S, Werner P, Gun J, Gelman F, Lev O (2012) Field and laboratory studies of the fate and enantiomeric enrichment of venlafaxine and O-desmethylvenlafaxine under aerobic and anaerobic conditions. Chemosphere 88:98–105

    CAS  Google Scholar 

  87. Brienza M, Chiron S (2017) Enantioselective reductive transformation of climbazole: a concept towards quantitative biodegradation assessment in anaerobic biological treatment processes. Water Res 116:203–210

    CAS  Google Scholar 

  88. Souchier M, Benali-Raclot D, Casella C, Ingrand V, Chiron S (2016) Enantiomeric fractionation as a tool for quantitative assessment of biodegradation: the case of metoprolol. Water Res 95:19–26

    CAS  Google Scholar 

  89. Poiger T, Müller M, Buser H-R, Buerge I (2015) Environmental behavior of the chiral herbicide haloxyfop. 1. Rapid and preferential interconversion of the enantiomers in soil. J Agric Food Chem 63:2583–2590

    CAS  Google Scholar 

  90. Arbeli Z, Fuentes CL (2007) Accelerated biodegradation of pesticides: an overview of the phenomenon, its basis and possible solutions; and a discussion on the tropical dimension. Crop Prot 26:1733–1746

    CAS  Google Scholar 

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Brienza, M., Huerta, B., Manasfi, R., Chiron, S. (2020). Soil Sorption and Degradation Studies of Pharmaceutical Compounds Present in Recycled Wastewaters Based on Enantiomeric Fractionation. In: Pérez Solsona, S., Montemurro, N., Chiron, S., Barceló, D. (eds) Interaction and Fate of Pharmaceuticals in Soil-Crop Systems. The Handbook of Environmental Chemistry, vol 103. Springer, Cham. https://doi.org/10.1007/698_2020_638

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