Degradation routes of RDX in various redox systems

ACS Symposium Series

Volumn 1071, Issue , 2011, Pages 441-462

  Halasz, Annamaria ^a   Hawari, Jalal ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC STRUCTURE; NITROGEN OXIDES; NITROGEN REMOVAL; REDOX REACTIONS;

AQUATIC SYSTEM; HEXAHYDRO-1 ,3 ,5-TRINITRO-1 ,3 ,5-TRIAZINE; KNOWLEDGE GAPS; MULTIFUNCTIONAL GROUP; REDOX CHEMISTRY; REDOX SYSTEMS; RESEARCH NEEDS; TRANSFORMATION PATHWAYS;

DEGRADATION;

EID: 84863503387     PISSN: 00976156     EISSN: 19475918     Source Type: Book Series    
DOI: 10.1021/bk-2011-1071.ch020     Document Type: Conference Paper

References (95)

1. Jenkins, T. F.; Hewitt, A. D.; Grant, C. L.; Thiboutot, S.; Ampleman, G.; Walsh, M. E.; Ranney, T. A.; Ramsey, C. A.; Palazzo, A. J.; Pennington, J. P. Identity and distribution of residues of energetic compounds at army live-fire training ranges. Chemosphere 2006, 63, 1280-90.
2. Xu, W.; Dana, K. E.; Mitch, W. A. Black carbon-mediated destruction of nitroglycerin and RDX by hydrogen sulfide. Environ. Sci. Technol. 2010, 44, 6409-15.
3. Hawari, J.; Beaudet, S.; Halasz, A.; Thiboutot, S.; Ampleman, G. Microbial degradation of explosives: Biotransformation versus mineralization. Appl. Microbiol. Biotechnol. 2000, 54, 605-618.
4. Thorn, K. A.; Pennington, J. C.; Kennedy, K. R.; Cox, L. G.; Hayes, C. A.; Porter, B. E. N-15 NMR study of the immobilization of 2,4-and 2,6-dinitrotoluene in aerobic compost. Environ. Sci. Technol. 2008, 42, 2542-50.
5. Stenuit, B. A.; Agathos, S. N. Microbial 2,4,6-trinitrotoluene degradation: Could we learn from (bio)chemistry for bioremediation and vice versa? Appl. Microbiol. Biotechnol. 2010, 88, 1043-64.
6. Wittich, R.-M.; Ramos, J. L.; van Dillewijn, P. Microorganisms and explosives: Mechanisms of nitrogen release from TNT for use as an N-source for growth. Environ. Sci. Technol. 2009, 43, 2773-76.
7. van Dillewijn, P.; Wittich, R.-M.; Caballero, A.; Ramos, J.-L. Type II hydride transferases from different microorganisms yield nitrite and diarylamines from polynitroaromatic compounds. Appl. Environ. Microbiol. 2008, 74, 6820-23.
8. Stenuit, B.; Eyers, L.; El Fantroussi, S.; Agathos, N. Promising strategies for the mineralization of 2,4,6-trinitrotoluene. Rev. Environ. Sci. Bio/Technol. 2005, 4, 39-60.
9. Sheremata, T.; Halasz, A.; Paquet, L.; Thiboutot, S.; Ampleman, G.; Hawari, J. The fate of cyclic nitramine explosive RDX in natural soil. Environ. Sci. Technol. 2001, 35, 1037-40.
10. Gong, P.; Hawari, J.; Thiboutot, S.; Ampleman, G.; Sunahara, G. I. Ecotoxicological effects of hexahydro-1,3,5-trinitro-1,3,5-triazine on soil microbial activities. Environ. Toxicol. Chem. 2001, 20, 947-51.
11. Lachance, B.; Robidoux, P. Y.; Hawari, J.; Ampleman, G.; Thiboutot, S.; Sunahara, G. I. Cytotoxic and genotoxic effects of energetic compounds on bacterial and mammalian cells in vitro. Mutat. Res. 1999, 444, 25-39.
12. Monteil-Rivera, F.; Halasz, A.; Groom, C.; Zhao, J.-S.; Thiboutot, S.; Ampleman, G.; Hawari J. Fate and transport of explosives in the environment A Chemist's view. In Ecotoxicology of Explosives and Unexploded Ordnance; Sunahara, G. I., Lutofo, G., Kuperman, R. G., Hawari, J., Eds.; CRC Press: Boca Raton, FL, 2009; pp 5-33.
13. Monteil-Rivera, F.; Paquet, L.; Giroux, R.; Hawari, J. Contribution of hydrolysis in the abiotic attenuation of RDX and HMX in coastal waters. J. Environ. Qual. 2008, 37, 858-64.
14. Hawari, J.; Halasz, A. Microbial degradation of explosives. In The Encyclopedia of Environmental Microbiology; Bitton, G., Ed.; John Wiley & Sons: Amsterdam, The Netherlands, 2002; pp 1979-93.
15. Borch, T.; Kretzschmar, R.; Kappler, A.; van Cappellen, P.; Ginder-Vogel, M.; Voegelin, A.; Campbell, K. Biogeochemical redox processes and their impact on contaminant dynamics. Environ. Sci. Technol. 2010, 44, 15-23.
16. Heimann, A.; Jakobsen, R.; Blodau, C. Energetic constraints on H2-dependent terminal electron accepting processes in anoxic environments: A review of observations and model approaches. Environ. Sci. Technol. 2010, 44, 24-33.
17. Zhang, H.; Weber, E. J. Elucidating the role of electron shuttles in reductive transformations in anaerobic sediments. Environ. Sci. Technol. 2009, 43, 1042-48.
18. Hau, H. H.; Gralnick, J. A. Ecology and biotechnology of the genus Shewanella. Annu. Rev. Microbiol. 2007, 61, 237-58.
19. Balakrishnan, V.K.; Halasz, A.; Hawari, J. Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: New insights into degradation pathways obtained by the observation of novel intermediates. Environ. Sci. Technol. 2003, 37, 1838-43.
20. Bose, P.; Glaze, W. H.; Maddox, D. S. Degradation of RDX by various advanced oxidation processes: II. Organic by-products. Water Res. 1998, 32, 1005-18.
21. Hawari, J.; Halasz, A.; Groom, C.; Deschamps, S.; Paquet, L.; Beaulieu, C.; Corriveau, A. Photodegradation of RDX in aqueous solution: A mechanistic probe for biodegradation with Rhodococcus sp. Environ. Sci. Technol. 2002, 36, 5117-23.
22. Oh, S.-Y.; Chiu, P. C.; Kim, B. J.; Cha, D. K. Enhancing Fenton oxidation of TNT and RDX through pretreatment with zero-valent iron. Water Res. 2003, 37, 4275-83.
23. Adam, M. L.; Comfort, S. D.; Morley, M. C.; Snow, D. D. Remediating RDX-contaminated ground water with permanganate: Laboratory investigations for the Pantex perched aquifer. J. Environ. Qual. 2004, 33, 2165-73.
24. Wanaratna, P.; Christodoulatos, C.; Sidhoum, M. Kinetics of RDX degradation by zero-valent iron (ZVI). J. Hazard. Mater. 2006, 136, 68-74.
25. Shrout, J. D.; Larese-Casanova, P.; Scherer, M. M.; Alvarez, P. J. Sustained and complete hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) degradation in zero-valent iron simulated barriers under different microbial conditions. Environ. Technol. 2005, 26 (10), 1115-26.
26. Comfort, S. D.; Shea, P. J.; Machacek, T. A.; Satapanajaru, T. Pilot-scale treatment of RDX-contaminated soil with zerovalent iron. J. Environ. Qual. 2003, 32, 1717-25.
27. Wildman, M. J; Alvarez, P. J. J. RDX degradation using an integrated Fe(0)-microbial treatment approach. Water Sci. Technol. 2001, 43 (2), 25-33.
28. Oh, B.-T.; Just, C. L.; Alvarez, P. J. J. Hexahydro-1,3,5-trinitro-1,3,5- triazine mineralization by zerovalent iron and mixed anaerobic cultures. Environ. Sci. Technol. 2001, 35, 4341-46.
29. Naja, G.; Halasz, A.; Thiboutot, S.; Ampleman, G.; Hawari, J. Degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) using zerovalent iron nanoparticles. Environ. Sci. Technol. 2008, 42, 4364-70.
30. Fuller, M. E.; Schaefer, C. E.; Lowey, J. M. Degradation of explosivesrelated compounds using nickel catalysts. Chemosphere 2007, 67, 419-27.
31. McHugh, C. J.; Smith, W. E.; Graham, D. The first controlled reduction of the high explosive RDX. Chem. Commun. 2002, 21, 2514-15.
32. Fidler, R.; Legron, T.; Carvalho-Knighton, K.; Geiger, C. L.; Sigman, M. E.; Clausen, C. A. Environmental Applications of Nanoscale and Microscale Reactive Metal Particles; ACS Symposium Series; American Chemical Society: Washington, DC, 2009; Vol. 1027, Chapter 7, pp 117-34.
33. Kwon, M. J.; Finneran, K. T. Electron shuttle-stimulated RDX mineralization and biological production of 4-nitro-2,4-diazabutanal (NDAB) in RDX-contaminated aquifer material. Biodegradation 2010, 21, 923-37.
34. Bhushan, B.; Halasz, A.; Hawari, J. Effect of iron(III), humic acids and anthraquinone-2,6-disulfonate on biodegradation of cyclic nitramines by Clostridium sp. EDB2. J. Appl. Microbiol. 2006, 100, 555-63.
35. Kemper, J. M.; Ammar, E.; Mitch, W. A. Abiotic degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine in the presence of hydrogen sulfide and black carbon. Environ. Sci. Technol. 2008, 42, 2118-23.
36. Gregory, K. B.; Larese-Casanova, P.; Parkin, G. F.; Scherer, M. M. Abiotic transformation of hexahydro-1,3,5-trinitro-1,3,5-triazine by FeII bound to magnetite. Environ. Sci. Technol. 2004, 38, 1408-14.
37. An, C.; He, Y.; Huang, G. H; Yang, S. Degradation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) by anaerobic mesophilic granular sludge from a UASB reactor. J. Chem. Technol. Biotechnol. 2010, 85, 831-38.
38. Hawari, J.; Halasz, A.; Sheremata, T.; Beaudet, S.; Groom, C.; Paquet, L.; Rhofir, C.; Ampleman, G.; Thiboutot, S. Characterization of metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) with municipal anaerobic sludge. Appl. Environ. Microbiol. 2000, 66, 2652-57.
39. McCormick, N. G.; Cornell, J. H.; Kaplan, A. M. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine. Appl. Environ. Microbiol. 1981, 42, 817-23.
40. Boopathy, R.; Gurgas, M.; Ullian, J.; Manning, J. F. Metabolism of explosive compounds by sulfate-reducing bacteria. Curr. Microbiol. 1998, 37, 127-31.
41. Freedman, D. L.; Sutherland, K. W. Biodegradation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) under nitrate-reducing conditions. Water Sci. Technol. 1998, 38, 33-40.
42. Bradley, P. M.; Dinicola, R. S. RDX (hexahydro-1,3,5-trinitro-1,3,5- triazine) biodegradation in aquifer sediments under manganese-reducing conditions. Bioremediation J. 2005, 9, 1-8.
43. Adrian, N. R.; Arnett, C. M. Anaerobic biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by Acetobacterium malicum strain HAAP-1 isolated from a methanogenic mixed culture. Curr. Microbiol. 2004, 48, 332-40.
44. Zhao, J.-S.; Manno, D.; Hawari, J. Regulation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) metabolism in Shewanella halifaxensis HAW-EB4 by terminal electron acceptor and involvement of c-type cytochrome. Microbiology (Reading, U. K.) 2008, 154, 1026-37.
45. Kwon, M. J.; Finneran, K. T. Biotransformation products and mineralization potential for hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) in abiotic versus biological degradation pathways with anthraquinone-2,6- disulfonate (AQDS) and Geobacter metallireducens. Biodegradation 2008, 19, 705-15.
46. Kwon, M. J.; Finneran, K. T. Microbially mediated biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine by extracellular electron shuttling compounds. Appl. Environ. Microbiol. 2006, 72, 5933-41.
47. Fournier, D.; Halasz, A.; Spain, J.; Fiurasek, P.; Hawari, J. Determination of key metabolites during biodegradation of hexahydro-1,3,5- trinitro-1,3,5-triazine with Rhodococcus sp. strain DN22. Appl. Environ. Microbiol. 2002, 68, 166-72.
48. Seth-Smith, H. M. B.; Rosser, S. J.; Basran, A.; Travis, E. R.; Dabbs, E. R.; Nicklin, S.; Bruce, N. C. Cloning, sequencing, and characterization of the hexahydro1,3,5-trinitro-1,3,5-triazine degradation gene cluster from Rhodococcus rhodochrous. Appl. Environ. Microbiol. 2002, 68, 4764-71.
49. Coleman, N. V.; Nelson, D. R.; Duxbury, T. Aerobic biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) as a nitrogen source by a Rhodococcus sp., strain DN22. Soil Biol. Biochem. 1998, 30, 1159-67.
50. Thompson, K. T.; Crocker, F. H.; Fredrickson, H. L. Mineralization of the cyclic nitramine explosive hexahydro1,3,5-trinitro-1,3,5-triazine by Gordonia and Williamsia spp. Appl. Environ. Microbiol. 2005, 71, 8265-72.
51. Bhushan, B.; Halasz, A.; Spain, J. C.; Hawari, A. Diaphorase catalyzed biotransformation of RDX via N-denitration mechanism. Biochem. Biophys. Res. Commun. 2002, 296, 779-84.
52. Bhushan, B.; Halasz, A.; Spain, J.; Thiboutot, S.; Ampleman, G.; Hawari, J. Biotransformation of hexahydro-1,3,5-trinitro-1,3,5-triazine catalyzed by a NAD(P)H: Nitrate oxidoreductase from Aspergillus niger. Environ. Sci. Technol. 2002, 36, 3104-08.
53. Jackson, R. G.; Rylott, E. L.; Fournier, D.; Hawari, J.; Bruce, N. C. Exploring the biochemical properties and remediation applications of the unusual explosive-degrading P450 system XplA/B. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 16822-27.
54. Bhushan, B.; Trott, S.; Spain, J. C.; Halasz, A.; Paquet, L.; Hawari, J. Biotransformation of hexahydro1,3,5-trinitro-1,3,5-triazine (RDX) by rabbit liver cytochrome P450: Insight into the mechanism of RDX biodegradation by Rhodococcus sp. strain DN22. Appl. Environ. Microbiol. 2003, 69, 1347-51.
55. Weber, K. A.; Urrutia, M. M.; Churchill, P. F.; Kukkadapu, R. K.; Roden, E. E. Anaerobic redox cycling of iron by freshwater sediment microorganisms. Environ. Microbiol. 2006, 8, 100-13.
56. 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.
57. Lovley, D. R. Microbial Fe(III) reduction in subsurface environments. FEMS Microbiol. Rev. 1997, 20, 305-13.
58. Curtis, G.P.; Reinhard, M. Reductive dehalogenation of hexachloroethane, carbon tetrachloride, and bromoform by anthrahydroquinone disulfonate and humic acid. Environ. Sci. Technol. 1994, 28, 2393-401.
59. Lovley, D. R.; Giovannoni, S. J.; White, D. C.; Champine, J. E.; Phillips, E. J. P.; Gorby, Y. A.; Goodwin, S. Geobacter metallireducens gen. nov. sp. nov., a microorganism capable of coupling the complete oxidation of organic compounds to the reduction of iron and other metals. Arch. Microbiol. 1993, 159, 336-44.
60. Schwarzenbach, R. P.; Stierli, R.; Lanz, K.; Zeyer, J. Quinone and iron mediated reduction of nitroaromatic compounds in homogeneous aqueous solution. Environ. Sci. Technol. 1990, 24, 1566-74.
61. Kwon, M. J.; Finneran, K. T. Hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) reduction is concurrently mediated by direct electron transfer from hydroquinones and resulting biogenic Fe(II) formed during electron shuttle-amended biodegradation. Environ. Engineer. Sci. 2009, 26, 961-71.
62. Bhushan, B.; Halasz, A.; Thiboutot, S.; Ampleman, G.; Hawari, J. Chemotaxis-mediated biodegradation of cyclic nitramine explosives RDX, HMX, and CL-20 by Clostridium sp. EDB2. Biochem. Biophys. Res. Commun. 2004, 316, 816-21.
63. Zhao, J.-S.; Deng, Y.; Manno, D.; Hawari, J. Shewanella spp. genomic evolution for a cold marine lifestyle and in-situ explosive biodegradation. PLoS ONE 2010, 5 (2), e9109; doi:10.1371/journal.pone.0009109.
64. Zhao, J.-S.; Spain, J.; Thiboutot, S.; Ampleman, G.; Greer, C.; Hawari, J. Phylogeny of cyclic nitramine-degrading psychrophilic bacteria in marine sediment and their potential role in natural attenuation of explosives. FEMS Microbiol. Ecol. 2004, 49, 349-57.
65. Kim, D.; Strathmann, T. J. Role of organically complexed iron(II) species in the reductive transformation of RDX in anoxic environments. Environ. Sci. Technol. 2007, 41, 1257-64.
66. Larese-Casanova, P.; Scherer, M. M. Abiotic transformation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by green rusts. Environ. Sci. Technol. 2008, 42, 3975-81.
67. Gent, D. B.; Wani, A. H.; Davis, J. L.; Alshawabkeh, A. Electrolytic redox and electrochemical generated alkaline hydrolysis of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) in sand column. Environ. Sci. Technol. 2009, 43, 6301-07.
68. Bonin, P. M. L.; Bejan, D.; Schutt, L.; Hawari, J.; Bunce, N. J. Electrochemical reduction of hexahydro-1,3,5-trinitro-1,3,5-triazine in aqueous solutions. Environ. Sci. Technol. 2004, 38, 1595-99.
69. Binks, P. R.; Nicklin, S.; Bruce, N. C. Degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by Stenotrophomonas maltophilia PB1. Appl. Environ. Microbiol. 1995, 61, 1318-22.
70. Halasz, A.; Manno, D.; Strand, S. E.; Bruce, N. C.; Hawari, J. Biodegradation of RDX and MNX with Rhodococcus sp. strain DN22: New insights into the degradation pathway. Environ. Sci. Technol. 2010, 44, 9330-36.
71. Bhatt, M.; Zhao, J.-S.; Halasz, A.; Hawari, J. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine by novel fungi isolated from unexploded ordnance contaminated marine sediment. J. Ind. Microbiol. Biotechnol. 2006, 33, 850-58.
72. Sheremata, T. W.; Hawari, J. Mineralization of RDX by the white rot fungus Phanerochaete chrysosporium to carbon dioxide and nitrous oxide. Environ. Sci. Technol. 2000, 34, 3384-88.
73. Bhatt, M.; Zhao, J.-S.; Monteil-Rivera, F.; Hawari, J. Biodegradation of cyclic nitramines by tropical marine sediment bacteria. J. Ind. Microbiol. Biotechnol. 2005, 32, 261-67.
74. Zhao, J.-S.; Paquet, L.; Halasz, A.; Hawari, J. Metabolism of hexahydro-1,3,5-trinitro-1,3,5-triazine through initial reduction to hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine followed by denitration in Clostridium bifermentants HAW-1. Appl. Microbiol. Biotechnol. 2003, 63, 187-93.
75. Zhao, J.-S.; Halasz, A.; Paquet, L.; Beaulieu, C.; Hawari, J. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine and its mononitroso derivative hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine by Klebsiella pneumoniae strain SCZ-1 isolated from an anaerobic sludge. Appl. Environ. Microbiol. 2002, 68, 5336-41.
76. Beller, H. R. Anaerobic biotransformation of RDX (hexahydro-1,3,5- trinitro-1,3,5-triazine) by aquifer bacteria using hydrogen as the sole electron donor. Water Res. 2002, 36, 2533-40.
77. Kitts, C. L.; Cunningham, D. P.; Unkefer, P. J. Isolation of three hexahydro-1,3,5-trinitro-1,3,5-triazine-degrading species of the family Enterobacteriaceae from nitramine explosive-contaminated soil. Appl. Environ. Microbiol. 1994, 60, 4608-711.
78. Zhang, B.; Kendall, R. J.; Anderson, T. A. Toxicity of the explosive metabolites hexahydro-1,3,5-trinitroso-1,3,5-triazine (TNX) and hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine (MNX) to the earthworm Eisenia fetida. Chemosphere 2006, 64, 86-95.
79. Shen, C. F.; Hawari, J.; Ampleman, G.; Thiboutot, S.; Guiot, S. R. Enhanced biodegradation and fate of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) and octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in anaerobic soil slurry bioprocess. Bioremed. J. 2000, 4, 27-39.
80. Halasz, A.; Spain, J.; Paquet, L.; Beaulieu, C.; Hawari, J. Insights into the formation and degradation mechanisms of methylenedinitramine during the incubation of RDX with anaerobic sludge. Environ. Sci. Technol. 2002, 36, 633-38.
81. Lamberton, A. H. Some aspects of the chemistry of nitramines. Q. Rev. Chem. Soc. 1951, 5, 75-98.
82. Fournier, D.; Trott, S.; Spain, J.; Hawari, J. Metabolism of the aliphatic nitramine 4-nitro-2,4-diazabutanal by Methylobacterium sp. strain JS178. Appl. Environ. Microbiol. 2005, 71, 4199-202.
83. Fournier, D.; Halasz, A.; Spain, J. C.; Spanggord, R. J.; Bottaro, J. C.; Hawari, J. Biodegradation of the hexahydro-1,3,5-trinitro-1,3,5-triazine ring cleavage product 4-nitro-2,4-diazabutanal by Phanerochaete chrysosporium. Appl. Environ. Microbiol. 2004, 70, 1123-28.
84. Fuller, M. E.; Perreault, N.; Hawari, J. Microaerophilic degradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) by three Rhodococcus strains. Lett. Appl. Microbiol. 2010, 51, 313-18.
85. Ignarro, L. J.; Fukuto, J. M.; Griscavage, J. M.; Rogers, N. E.; Byrns, R. E. Oxidation of nitric oxide in aqueous solution to nitrite but not nitrate : Comparison with enzymatically formed nitric oxide from L-arginine. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8103-07.
86. Guengerich, F. P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 2001, 14, 611-50.
87. Sagi-Ben Moshe, S.; Ronen, Z.; Dahan, O.; Bernstein, A.; Weisbrod, N.; Gelman, F.; Adar, E. Isotopic evidence and quantification assessment of in situ RDX biodegradation in the deep unsaturated zone. Soil Biol. Biochem. 2010, 42, 1253-62.
88. Bernstein, A.; Adar, E.; Ronen, Z.; Lowag, H.; Stichler, W.; Meckenstock, R. U. Quantifying RDX biodegradation in groundwater using d15N isotope analysis. J. Contam. Hydrol. 2010, 111, 25-35.
89. Bernstein, A.; Ronen, Z.; Adar, E.; Nativ, R.; Lowag, H.; Stichler, W.; Meckenstock, R. U. Compound-specific isotope analysis of RDX and stable isotope fractionation during aerobic and anaerobic biodegradation. Environ. Sci. Technol. 2008, 42, 7772-77.
90. Radajewski, S.; Ineson, P.; Parekh, N. R.; Murrell, J. C. Stable-isotope probing as a tool in microbial ecology. Nature 2000, 403, 646-49.
91. Roh, H.; Yu, C.-P.; Fuller, M. E.; Chu, K. H. Identification of hexahydro-1,3,5-trinitro-1,3,5-triazine-degrading microorganisms via 15N-stable isotope probing. Environ. Sci. Technol. 2009, 43, 2502-11.
92. Schmidt, T. C.; Zwank, L.; Elsner, M.; Berg, M.; Meckenstock, R. U.; Haderlein, S. B. Compound-specific stable isotope analysis of organic contaminants in natural environments: a critical review of the state of the art, prospects, and future challenges. Anal. Bioanal. Chem. 2004, 378, 283-300.
93. Elsner, M.; Hofstetter, T. B. Current perspectives on the mechanisms of chlorohydrocarbon degradation in subsurface.In Aquatic Redox Chemistry; Tratnyek, P. G., Grundl, T. J., Haderlein, S. B., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC, 2011; Vol. 1071, Chapter 19, pp 407-439.
94. Amaral, H. I. F.; Fernandes, J.; Berg, M.; Schwarzenbach, R. P.; Kipfer, R. Assessing TNT and DNT groundwater contamination by compound-specific isotope analysis and 3H-3He groundwater dating: A case study in Portugal. Chemosphere 2009, 77, 805-12.
95. Gallagher, E. M.; Young, L. Y.; McGuinness, L. M.; Kerkhof, L. J. Detection of 2,4,6-trinitrotoluene-utilizing anaerobic bacteria by 15N and 13C incorporation. Appl. Environ. Microbiol. 2010, 76, 1695-98.