Potential for abiotic reduction of pesticides in prairie pothole porewaters

Environmental Science and Technology

Volumn 46, Issue 6, 2012, Pages 3177-3187

  Zeng, Teng ^a   Chin, Yu Ping ^b   Arnold, William A ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

^b OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABIOTIC REDUCTION; DISSOLVED ORGANIC MATTERS; EXPERIMENTAL EVIDENCE; INLAND WETLANDS; MINERAL PHASIS; NATURAL ATTENUATION; NONPOINT SOURCES; PESTICIDE POLLUTION; PORE WATERS; RAPID DEGRADATION; REDUCED SULFUR SPECIES; REDUCTIVE TRANSFORMATIONS; SEDIMENTARY ENVIRONMENT; WATER CHEMISTRY;

ANOXIC SEDIMENTS; LAKES; POLYSULFIDES; REACTION RATES; SEDIMENTATION; SULFUR;

PESTICIDES;

AMINE; ANILINE DERIVATIVE; BISULFIDE; DINITROANILINE; DISSOLVED ORGANIC MATTER; MINERAL; NATURAL PRODUCT; PESTICIDE; POLYSULFIDE; SULFUR; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

AGRICULTURAL LAND; LAKE POLLUTION; LAKE WATER; NONPOINT SOURCE POLLUTION; PESTICIDE RESIDUE; POREWATER; PRAIRIE; WATER CHEMISTRY; WETLAND;

ABIOTIC STRESS; ARTICLE; BIOREMEDIATION; BIOTRANSFORMATION; CHEMICAL COMPOSITION; CHEMICAL REACTION; CONTROLLED STUDY; FRACTIONATION; LAKE; LAKE SEDIMENT; PRAIRIE; PRAIRIE POTHOLE LAKE; REDUCTION; SYNTHESIS;

ANILINE COMPOUNDS; KINETICS; LAKES; NORTH DAKOTA; OXIDATION-REDUCTION; PESTICIDES; SULFIDES; WATER POLLUTANTS, CHEMICAL;

NORTH AMERICA;

EID: 84858633512     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es203584d     Document Type: Article

References (116)

1. Ju, K.-S.; Parales, R. E. Nitroaromatic compounds, from synthesis to biodegradation Microbiol. Mol. Biol. Rev. 2010, 74, 250-272
2. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry; John Wiley & Sons, Inc.: Hoboken, NJ, 2003.
3. Wahid, P. A.; Ramakrishna, C.; Sethunathan, N. Instantaneous degradation of parathion in anaerobic soils J. Environ. Qual. 1980, 9, 127-130 (Pubitemid 10149703)
4. Wolfe, N. L.; Kitchens, B. E.; Macalady, D. L.; Grundl, T. J. Physical and chemical factors that influence the anaerobic degradation of methyl parathion in sediment systems Environ. Toxicol. Chem. 1986, 5, 1019-1026
5. Heijman, C. G.; Holliger, C.; Glaus, M. A.; Schwarzenbach, R. P.; Zeyer, J. Abiotic reduction of 4-chloronitrobenzene to 4-chloroaniline in a dissimilatory iron-reducing enrichment culture Appl. Environ. Microbiol. 1993, 59, 4350-4353 (Pubitemid 23361431)
6. Heijman, C. G.; Grieder, E.; Holliger, C.; Schwarzenbach, R. P. Reduction of nitroaromatic compounds coupled to microbial iron reduction in laboratory aquifer columns Environ. Sci. Technol. 1995, 29, 775-783
7. Rügge, K.; Hofstetter, T. B.; Haderlein, S. B.; Bjerg, P. L.; Knudsen, S.; Zraunig, C.; Mosbæk, H.; Christensen, T. H. Characterization of predominant reductants in an anaerobic leachate-contaminated aquifer by nitroaromatic probe compounds Environ. Sci. Technol. 1998, 32, 23-31 (Pubitemid 28035897)
8. Hofstetter, T. B.; Heijman, C. G.; Haderlein, S. B.; Holliger, C.; Schwarzenbach, R. P. Complete reduction of TNT and other (poly)nitroaromatic compounds under iron-reducing subsurface conditions Environ. Sci. Technol. 1999, 33, 1479-1487 (Pubitemid 29217836)
9. Simon, R.; Colón, D.; Tebes-Stevens, C. L.; Weber, E. J. Effect of redox zonation on the reductive transformation of p -cyanonitrobenzene in a laboratory sediment column Environ. Sci. Technol. 2000, 34, 3617-3622
10. Hoferkamp, L. A.; Weber, E. J. Nitroaromatic reduction kinetics as a function of dominant terminal electron acceptor processes in natural sediments Environ. Sci. Technol. 2006, 40, 2206-2212
11. Tobler, N. B.; Hofstetter, T. B.; Schwarzenbach, R. P. Assessing iron-mediated oxidation of toluene and reduction of nitroaromatic contaminants in anoxic environments using compound-specific isotope analysis Environ. Sci. Technol. 2007, 41, 7773-7780 (Pubitemid 350133317)
12. Tratnyek, P. G.; Weber, E. J.; Schwarzenbach, R. P. Quantitative structure-activity relationships for chemical reductions of organic contaminants Environ. Toxicol. Chem. 2003, 22, 1733-1742 (Pubitemid 37337302)
13. Hakala, J. A.; Fimmen, R. L.; Chin, Y.-P.; Agrawal, S. G.; Ward, C. P. Assessment of the geochemical reactivity of Fe-DOM complexes in wetland sediment pore waters using a nitroaromatic probe compound Geochim. Cosmochim. Acta 2009, 73, 1382-1393
14. Yan, L.; Bailey, G. W. Sorption and abiotic redox transformation of nitrobenzene at the smectite-water interface J. Colloid Interface Sci. 2001, 241, 142-153 (Pubitemid 32786672)
15. Hofstetter, T. B.; Schwarzenbach, R. P.; Haderlein, S. B. Reactivity of Fe(II) species associated with clay minerals Environ. Sci. Technol. 2003, 37, 519-528 (Pubitemid 36159641)
16. Hofstetter, T. B.; Neumann, A.; Schwarzenbach, R. P. Reduction of nitroaromatic compounds by Fe(II) species associated with iron-rich smectites Environ. Sci. Technol. 2005, 40, 235-242 (Pubitemid 43069909)
17. Neumann, A.; Hofstetter, T. B.; Lüssi, M.; Cirpka, O. A.; Petit, S.; Schwarzenbach, R. P. Assessing the redox reactivity of structural iron in smectites using nitroaromatic compounds as kinetic probes Environ. Sci. Technol. 2008, 42, 8381-8387
18. Hofstetter, T. B.; Neumann, A.; Arnold, W. A.; Hartenbach, A. E.; Bolotin, J.; Cramer, C. J.; Schwarzenbach, R. P. Substituent effects on nitrogen isotope fractionation during abiotic reduction of nitroaromatic compounds Environ. Sci. Technol. 2008, 42, 1997-2003 (Pubitemid 351497693)
19. II uptake and nitrobenzene reduction Environ. Sci. Technol. 2009, 43, 3675-3680
20. Gorski, C. A.; Nurmi, J. T.; Tratnyek, P. G.; Hofstetter, T. B.; Scherer, M. M. Redox behavior of magnetite: Implications for contaminant reduction Environ. Sci. Technol. 2010, 44, 55-60
21. Klausen, J.; Troeber, S. P.; Haderlein, S. B.; Schwarzenbach, R. P. Reduction of substituted nitrobenzenes by Fe(II) in aqueous mineral suspensions Environ. Sci. Technol. 1995, 29, 2396-2404
22. Schultz, C. A.; Grundl, T. J. pH dependence on reduction rate of 4-Cl-nitrobenzene by Fe(II)/montmorillonite systems Environ. Sci. Technol. 2000, 34, 3641-3648
23. Elsner, M.; Schwarzenbach, R. P.; Haderlein, S. B. Reactivity of Fe(II)-bearing minerals toward reductive transformation of organic contaminants Environ. Sci. Technol. 2004, 38, 799-807 (Pubitemid 38168748)
24. Klupinski, T. P.; Chin, Y.-P.; Traina, S. J. Abiotic degradation of pentachloronitrobenzene by Fe(II): Reactions on goethite and iron oxide nanoparticles Environ. Sci. Technol. 2004, 38, 4353-4360 (Pubitemid 39095231)
25. Colón, D.; Weber, E. J.; Anderson, J. L. QSAR study of the reduction of nitroaromatics by Fe(II) species Environ. Sci. Technol. 2006, 40, 4976-4982 (Pubitemid 44257462)
26. Larese-Casanova, P.; Cwiertny, D. M.; Scherer, M. M. Nanogoethite formation from oxidation of Fe(II) sorbed on aluminum oxide: Implications for contaminant reduction Environ. Sci. Technol. 2010, 44, 3765-3771
27. Naka, D.; Kim, D.; Strathmann, T. J. Abiotic reduction of nitroaromatic compounds by aqueous iron(II)-catechol complexes Environ. Sci. Technol. 2006, 40, 3006-3012 (Pubitemid 43673305)
28. Hakala, J. A.; Chin, Y.-P.; Weber, E. J. Influence of dissolved organic matter and Fe(II) on the abiotic reduction of pentachloronitrobenzene Environ. Sci. Technol. 2007, 41, 7337-7342 (Pubitemid 350071643)
29. Naka, D.; Kim, D.; Carbonaro, R. F.; Strathmann, T. J. Abiotic reduction of nitroaromatic contaminants by iron(II) complexes with organothiol ligands Environ. Toxicol. Chem. 2008, 27, 1257-1266 (Pubitemid 351839401)
30. Hartenbach, A. E.; Hofstetter, T. B.; Aeschbacher, M.; Sander, M.; Kim, D.; Strathmann, T. J.; Arnold, W. A.; Cramer, C. J.; Schwarzenbach, R. P. Variability of nitrogen isotope fractionation during the reduction of nitroaromatic compounds with dissolved reductants Environ. Sci. Technol. 2008, 42, 8352-8359
31. Colón, D.; Weber, E. J.; Anderson, J. L. Effect of natural organic matter on the reduction of nitroaromatics by Fe(II) species Environ. Sci. Technol. 2008, 42, 6538-6543
32. Schwarzenbach, R. P.; Stierli, R.; Lanz, K.; Zeyer, J. Quinone and iron porphyrin mediated reduction of nitroaromatic compounds in homogeneous aqueous solution Environ. Sci. Technol. 1990, 24, 1566-1574 (Pubitemid 20342980)
33. Dunnivant, F. M.; Schwarzenbach, R. P.; Macalady, D. L. Reduction of substituted nitrobenzenes in aqueous solutions containing natural organic matter Environ. Sci. Technol. 1992, 26, 2133-2141
34. Barrows, S. E.; Cramer, C. J.; Truhlar, D. G.; Elovitz, M. S.; Weber, E. J. Factors controlling regioselectivity in the reduction of polynitroaromatics in aqueous solution Environ. Sci. Technol. 1996, 30, 3028-3038 (Pubitemid 26332660)
35. Guo, X.; Jans, U. Kinetics and mechanism of the degradation of methyl parathion in aqueous hydrogen sulfide solution: Investigation of natural organic matter effects Environ. Sci. Technol. 2006, 40, 900-906 (Pubitemid 43222178)
36. Hartenbach, A.; Hofstetter, T. B.; Berg, M.; Bolotin, J.; Schwarzenbach, R. P. Using nitrogen isotope fractionation to assess abiotic reduction of nitroaromatic compounds Environ. Sci. Technol. 2006, 40, 7710-7716 (Pubitemid 46012566)
37. Sposito, G. Electron shuttling by natural organic matter: Twenty years after. In Aquatic Redox Chemistry; Tratnyek, P. G.; Grundl, T. J.; Haderlein, S. B., Eds.; American Chemical Society: Washington, DC, 2011; Vol. 1071, pp 113-127.
38. Tratnyek, P. G.; Macalady, D. L. Abiotic reduction of nitro aromatic pesticides in anaerobic laboratory systems J. Agric. Food. Chem. 1989, 37, 248-254 (Pubitemid 19046407)
39. Perlinger, J. A.; Kalluri, V. M.; Venkatapathy, R.; Angst, W. Addition of hydrogen sulfide to juglone Environ. Sci. Technol. 2002, 36, 2663-2669 (Pubitemid 34633487)
40. Nurmi, J. T.; Tratnyek, P. G. Electrochemical properties of natural organic matter (NOM), fractions of NOM, and model biogeochemical electron shuttles Environ. Sci. Technol. 2002, 36, 617-624 (Pubitemid 34157501)
41. Cory, R. M.; McKnight, D. M. Fluorescence spectroscopy reveals ubiquitous presence of oxidized and reduced quinones in dissolved organic matter Environ. Sci. Technol. 2005, 39, 8142-8149 (Pubitemid 41572395)
42. Heitmann, T.; Blodau, C. Oxidation and incorporation of hydrogen sulfide by dissolved organic matter Chem. Geol. 2006, 235, 12-20 (Pubitemid 44597162)
43. Ratasuk, N.; Nanny, M. A. Characterization and quantification of reversible redox sites in humic substances Environ. Sci. Technol. 2007, 41, 7844-7850 (Pubitemid 350133327)
44. Macalady, D. L.; Walton-Day, K. New light on a dark subject: On the use of fluorescence data to deduce redox states of natural organic matter (NOM) Aquat. Sci. 2009, 71, 135-143
45. Aeschbacher, M.; Sander, M.; Schwarzenbach, R. P. Novel electrochemical approach to assess the redox properties of humic substances Environ. Sci. Technol. 2010, 44, 87-93
46. Aeschbacher, M.; Vergari, D.; Schwarzenbach, R. P.; Sander, M. Electrochemical analysis of proton and electron transfer equilibria of the reducible moieties in humic acids Environ. Sci. Technol. 2011, 45, 8385-8394
47. Hojo, M.; Takagi, Y.; Ogata, Y. Kinetics of the reduction of nitrobenzenes by sodium disulfide J. Am. Chem. Soc. 1960, 82, 2459-2462
48. Cope, O. J.; Brown, R. K. The reduction of nitrobenzene by sodium sulphide in aqueous ethanol Can. J. Chem. 1961, 39, 1695-1710
49. Cope, O. J.; Brown, R. K. The reduction of nitrobenzene by hydrosulphide ion in aqueous media Can. J. Chem. 1962, 40, 2317-2328
50. van der Valk, A. G. The prairie potholes of North America. In The World's Largest Wetlands; Fraser, L. H.; Keddy, P. A., Eds.; Cambridge University Press: Cambridge, U.K., 2005; pp 393-423.
51. Gleason, R. A.; Euliss, N. H.; Tangen, B. A.; Laubhan, M. K.; Browne, B. A. USDA conservation program and practice effects on wetland ecosystem services in the Prairie Pothole Region Ecol. Appl. 2011, 21, S65-S81
52. Dahl, T. E. Wetlands Losses in the United States 1780s to 1980s; U.S. Department of the Interior, Fish and Wildlife Service: Washington, DC, 1990.
53. Johnson, R. R.; Oslund, F. T.; Hertel, D. R. The past, present, and future of prairie potholes in the United States J. Soil Water Conserv. 2008, 63, 84A-87A
54. Oslund, F. T.; Johnson, R. R.; Hertel, D. R. Assessing wetland changes in the Prairie Pothole Region of Minnesota from 1980 to 2007 J. Fish Wildl. Manage. 2010, 1, 131-135
55. Stubbs, M. Land Conversion in the Northern Plains; CRS Report for Congress RL33950; Resources, Science, and Industry Division, The National Council for Science and the Environment: Washington, DC, 2007.
56. Euliss, N. H.; Smith, L. M.; Liu, S.; Feng, M.; Mushet, D. M.; Auch, R. F.; Loveland, T. R. The need for simultaneous evaluation of ecosystem services and land use change Environ. Sci. Technol. 2010, 44, 7761-7763
57. Gascoigne, W. R.; Hoag, D.; Koontz, L.; Tangen, B. A.; Shaffer, T. L.; Gleason, R. A. Valuing ecosystem and economic services across land-use scenarios in the Prairie Pothole Region of the Dakotas, USA Ecol. Econ. 2011, 70, 1715-1725
58. Rashford, B. S.; Walker, J. A.; Bastian, C. T. Economics of grassland conversion to cropland in the Prairie Pothole Region Conserv. Biol. 2011, 25, 276-284
59. Goldsborough, L. G.; Crumpton, W. G. Distribution and environmental fate of pesticides in prairie wetlands Great Plains Res. 1998, 8, 73-95 (Pubitemid 28508113)
60. Donald, D. B.; Narine, P. G.; Lynne, Q.-A.; Kevin, C. Diffuse geographic distribution of herbicides in northern prairie wetlands Environ. Toxicol. Chem. 2001, 20, 273-279 (Pubitemid 32096891)
61. Detenbeck, N. E.; Elonen, C. M.; Taylor, D. L.; Cotter, A. M.; Puglisi, F. A.; Sanville, W. D. Effects of agricultural activities and best management practices on water quality of seasonal prairie pothole wetlands Wetlands Ecol. Manage. 2002, 10, 335-354 (Pubitemid 35211615)
62. Huckins, J. N.; Petty, J. D.; England, D. C. Distribution and impact of trifluralin, atrazine, and fonofos residues in microcosms simulating a northern prairie wetland Chemosphere 1986, 15, 563-588 (Pubitemid 16091178)
63. Grover, R.; Waite, D. T.; Cessna, A. J.; Nicholaichuk, W.; Irvin, D. G.; Kerr, L. A.; Best, K. Magnitude and persistence of herbicide residues in farm dugouts and ponds in the Canadian prairies Environ. Toxicol. Chem. 1997, 16, 638-643 (Pubitemid 27171888)
64. Cessna, A. J.; Donald, D. B.; Bailey, J.; Waiser, M.; Headley, J. V. Persistence of the sulfonylurea herbicides thifensulfuron-methyl, ethametsulfuron-methyl, and metsulfuron-methyl in farm dugouts (ponds) J. Environ. Qual. 2006, 35, 2395-2401 (Pubitemid 44870658)
65. Degenhardt, D.; Cessna, A. J.; Raina, R.; Farenhorst, A.; Pennock, D. J. Dissipation of six acid herbicides in water and sediment of two Canadian prairie wetlands Environ. Toxicol. Chem. 2011, 30, 1982-1989
66. Helling, C. S. Dinitroaniline herbicides in soils J. Environ. Qual. 1976, 5, 1-15
67. U.S. Geological Survey. Pesticide National Synthesis Project.2002 Pesticide Use Maps. http://water.usgs.gov/nawqa/pnsp/usage/maps/compound- listing.php?year=02 (accessed August 2011).
68. Zollinger, R.; McMullen, M.; Knodel, J.; Gray, J.; Jantzi, D.; Kimmet, G.; Hagemeister, K.; Schmitt, C. Pesticide Use and Pest Management Practices in North Dakota, 2008; Publication W-1446; North Dakota State University in cooperation with North Dakota Agricultural Statistics Service Extension: Fargo, ND, 2009.
69. Gilliom, R. J. Pesticides in U.S. streams and groundwater Environ. Sci. Technol. 2007, 41, 3408-3414
70. U.S. Environmental Protection Agency. Incidence and Severity of Sediment Contamination in Surface Waters of the United States, National Sediment Quality Survey, 2 nd ed.; EPA 823-R-04-007; U.S. Environmental Protection Agency: Washington, DC, 2004. http://water.epa.gov/polwaste/sediments/cs/upload/nsqs2ed- complete-2.pdf (accessed August 2011).
71. Persistent Bioaccumulative and Toxic (PBT) Chemical Program, U.S. Environmental Protection Agency. Guidance for Reporting Toxic Chemicals: Pesticides and Other Persistent Bioaccumulative Toxic (PBT) Chemicals; EPA 260-B-01-005; U.S. Environmental Protection Agency: Washington, DC, 2001. http://www.epa.gov/tri/guide-docs/pdf/2001/pest2001.pdf (accessed August 2011).
72. Rickert, D. E. Toxicity of Nitroaromatic Compounds; Hemisphere Publishing Corp.: Washington, DC, 1985.
73. Weber, J. B. Behavior of dinitroaniline herbicides in soils Weed Technol. 1990, 4, 394-406
74. Belden, J. B.; Phillips, T. A.; Henderson, K. L.; Clark, B. W.; Lydy, M. J.; Coats, J. R. Persistence, mobility, and bioavailability of pendimethalin and trifluralin in soil. Environmental Fate and Effects of Pesticides; American Chemical Society: Washington, DC, 2003; Vol. 853, pp 167-177.
75. Ciglenecki, I.; Kodba, Z.; Cosovic, B. Sulfur species in Rogoznica Lake Mar. Chem. 1996, 53, 101-110
76. Overmann, J.; Beatty, J. T.; Krouse, H. R.; Hall, K. J. The sulfur cycle in the chemocline of a meromictic salt lake Limnol. Oceanogr. 1996, 41, 147-156
77. Miller, P. L.; Vasudevan, D.; Gschwend, P. M.; Roberts, A. L. Transformation of hexachloroethane in a sulfidic natural water Environ. Sci. Technol. 1998, 32, 1269-1275 (Pubitemid 28208692)
78. Chin, Y.-P.; Traina, S. J.; Swank, C. R.; Backhus, D. Abundance and properties of dissolved organic matter in pore waters of a freshwater wetland Limnol. Oceanogr. 1998, 43, 1287-1296 (Pubitemid 28514772)
79. O'Loughlin, E. J.; Chin, Y.-P. Quantification and characterization of dissolved organic carbon and iron in sedimentary porewater from Green Bay, WI, USA Biogeochemistry 2004, 71, 371-386
80. Tor, J. M.; Xu, C.; Stucki, J. M.; Wander, M. M.; Sims, G. K. Trifluralin degradation under microbiologically induced nitrate and Fe(III) reducing conditions Environ. Sci. Technol. 2000, 34, 3148-3152 (Pubitemid 30649981)
81. Wang, S.; Arnold, W. A. Abiotic reduction of dinitroaniline herbicides Water Res. 2003, 37, 4191-4201 (Pubitemid 37011274)
82. Klupinski, T. P.; Chin, Y.-P. Abiotic degradation of trifluralin by Fe(II): Kinetics and transformation pathways Environ. Sci. Technol. 2003, 37, 1311-1318 (Pubitemid 36504945)
83. Hakala, J. A.; Chin, Y.-P. Abiotic reduction of pendimethalin and trifluralin in controlled and natural systems containing Fe(II) and dissolved organic matter J. Agric. Food. Chem. 2010, 58, 12840-12846
84. Zeng, T.; Ziegelgruber, K. L.; Chin, Y.-P.; Arnold, W. A. Pesticide processing potential in prairie pothole porewaters Environ. Sci. Technol. 2011, 45, 6814-6822
85. Cline, J. D. Spectrophotometric determination of hydrogen sulfide in natural waters Limnol. Oceanogr. 1969, 14, 454-458
86. Heitz, A.; Kagi, R. I.; Alexander, R. Polysulfide sulfur in pipewall biofilms: Its role in the formation of swampy odour in distribution systems Water Sci. Technol. 2000, 41, 271-278 (Pubitemid 30484653)
87. Kristiana, I.; Heitz, A.; Joll, C.; Sathasivan, A. Analysis of polysulfides in drinking water distribution systems using headspace solid-phase microextraction and gas chromatography-mass spectrometry J. Chromatogr., A 2010, 1217, 5995-6001
88. MacCrehan, W.; Shea, D. Temporal relationship of thiols to inorganic sulfur compounds in anoxic Chesapeake Bay sediment porewater. In Geochemical Transformations of Sedimentary Sulfur; Vairavamurthy, M. A.; Schoonen, M. A. A.; Eglinton, T. I.; Luther, G. W., III; Manowitz, B., Eds.; American Chemical Society: Washington, DC, 1995; Vol. 612, pp 294-310.
89. Zopfi, J.; Ferdelman, T. G.; Fossing, H. Distribution and fate of sulfur intermediates-sulfite, tetrathionate, thiosulfate, and elemental sulfur-in marine sediments Geol. Soc. Am. Spec. Pap. 2004, 379, 97-116
90. Marendic, N.; Norris, A. R. The interaction of sulfite ion with 2,4,6-trinitrobenzaldehyde: Kinetic, equilibrium, and proton magnetic resonance studies Can. J. Chem. 1973, 51, 3927-3935
91. Buncel, E.; Norris, A. R.; Russell, K. E.; Sheridan, P. J. Kinetic and thermodynamic studies of the reactions of sulfite ion with picramide, N -methylpicramide, and N,N -dimethylpicramide in aqueous solution Can. J. Chem. 1974, 52, 25-33
92. Annandale, M. T.; vanLoon, G. W.; Buncel, E. Regioselectivity and stereoelectronic effects in the reactions of the dinitroaniline herbicides trifluralin and benefin with nucleophiles Can. J. Chem. 1998, 76, 873-883 (Pubitemid 28527360)
93. H complexes in nucleophilic aromatic substitution reactions: Relative stabilities of electrochemically generated radicals Eur. J. Org. Chem. 2008, 2463-2472
94. Shea, D.; Helz, G. R. The solubility of copper in sulfidic waters-sulfide and polysulfide complexes in equilibrium with covellite Geochim. Cosmochim. Acta 1988, 52, 1815-1825
95. Smith, D. S.; Bell, R. A.; Kramer, J. R. Metal speciation in natural waters with emphasis on reduced sulfur groups as strong metal binding sites Comp. Biochem. Physiol., Part C: Toxicol. Pharmacol. 2002, 133, 65-74 (Pubitemid 35287057)
96. Willis, G. H.; Wander, R. C.; Southwick, L. M. Degradation of trifluralin in soil suspensions as related to redox potential J. Environ. Qual. 1974, 3, 262-265
97. Kearney, P. C.; Plimmer, J. R.; Wheeler, W. B.; Kontson, A. Persistence and metabolism of dinitroaniline herbicides in soils Pestic. Biochem. Physiol. 1976, 6, 229-238
98. Camper, N. D.; Stralka, K.; Skipper, H. D. Aerobic and anaerobic degradation of profluralin and trifluralin J. Environ. Sci. Health, Part B: Pestic. Contam. Agric. Wastes 1980, 15, 457-473
99. Singh, S. B.; Kulshrestha, G. Microbial-degradation of pendimethalin J. Environ. Sci. Health, Part B: Pestic. Contam. Agric. Wastes 1991, 26, 309-321
100. Bellinaso, M. D.; Greer, C. W.; Peralba, M. D.; Henriques, J. A. P.; Gaylarde, C. C. Biodegradation of the herbicide trifluralin by bacteria isolated from soil FEMS Microbiol. Ecol. 2003, 43, 191-194 (Pubitemid 36197880)
101. Okutman Tas, D.; Pavlostathis, S. G. Microbial reductive transformation of pentachloronitrobenzene under methanogenic conditions Environ. Sci. Technol. 2005, 39, 8264-8272 (Pubitemid 41572411)
102. Burton, E. D.; Bush, R. T.; Sullivan, L. A.; Hocking, R. K.; Mitchell, D. R. G.; Johnston, S. G.; Fitzpatrick, R. W.; Raven, M.; McClure, S.; Jang, L. Y. Iron-monosulfide oxidation in natural sediments: Resolving microbially mediated S transformations using XANES, electron microscopy, and selective extractions Environ. Sci. Technol. 2009, 43, 3128-3134
103. Giggenbach, W. Equilibriums involving polysulfide ions in aqueous sulfide solutions up to 240° Inorg. Chem. 1974, 13, 1724-1730
104. Glaus, M. A.; Heijman, C. G.; Schwarzenbach, R. P.; Zeyer, J. Reduction of nitroaromatic compounds mediated by Streptomyces sp. exudates Appl. Environ. Microbiol. 1992, 58, 1945-1951
105. Luther, G. W., III; Rickard, D. Metal sulfide cluster complexes and their biogeochemical importance in the environment J. Nanopart. Res. 2005, 7, 389-407
106. Rickard, D.; Luther, G. W., III. Metal sulfide complexes and clusters Rev. Mineral. Geochem. 2006, 61, 421-504 (Pubitemid 44313391)
107. Charriau, A.; Lesven, L.; Gao, Y.; Leermakers, M.; Baeyens, W.; Ouddane, B.; Billon, G. Trace metal behaviour in riverine sediments: Role of organic matter and sulfides Appl. Geochem. 2011, 26, 80-90
108. Yu, Y. S.; Bailey, G. W. Reduction of nitrobenzene by four sulfide minerals: Kinetics, products, and solubility J. Environ. Qual. 1992, 21, 86-94
109. Cheng, J. Y.; Suidan, M. T.; Venosa, A. D. Abiotic reduction of 2,4-dinitrotoluene in the presence of sulfide minerals under anoxic conditions Water Sci. Technol. 1996, 34, 25-33
110. Oh, S.-Y.; Chiu, P. C.; Cha, D. K. Reductive transformation of 2,4,6-trinitrotoluene, hexahydro-1,3,5-trinitro-1,3,5-triazine, and nitroglycerin by pyrite and magnetite J. Hazard. Mater. 2008, 158, 652-655
111. Oh, S.-Y.; Chiu, P. C. Graphite- and soot-mediated reduction of 2,4-dinitrotoluene and hexahydro-1,3,5-trinitro-1,3,5-triazine Environ. Sci. Technol. 2009, 43, 6983-6988
112. Weber, E. J.; Spidle, D. L.; Thorn, K. A. Covalent binding of aniline to humic substances. 1. Kinetic studies Environ. Sci. Technol. 1996, 30, 2755-2763
113. 15N NMR studies of nucleophilic addition reactions Environ. Sci. Technol. 1996, 30, 2764-2775
114. Johnson, W. C.; Millett, B. V.; Gilmanov, T.; Voldseth, R. A.; Guntenspergen, G. R.; Naugle, D. E. Vulnerability of northern prairie wetlands to climate change Bioscience 2005, 55, 863-872 (Pubitemid 41443700)
115. Millett, B. V.; Johnson, W. C.; Guntenspergen, G. R. Climate trends of the North American Prairie Pothole Region 1906-2000 Clim. Change 2009, 93, 243-267
116. Niemuth, N.; Wangler, B.; Reynolds, R. Spatial and temporal variation in wet area of wetlands in the Prairie Pothole Region of North Dakota and South Dakota Wetlands 2010, 30, 1053-1064