Perspectives of bioelimination of polynitroaromatic compounds

Biodegradation of Nitroaromatic Compounds and Explosives

Volumn , Issue , 2000, Pages 91-126

  Lenke, Hiltrud ^a   Achtnich, Christof ^a   Knackmuss, Hans Joachim ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

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EID: 12444281969     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (106)

1. Achtnich, C., E. Fernandes, J.-M. Bollag, H.-J. Knackmuss, and H. Lenke. 1999. Covalent bindings of reduced metabolites of [15N3]TNT to soil organic matter during a bioremediation process analyzed by 15N NMR spectroscopy. Environ. Sci. Technol. 33:4448-4456.
2. Achtnich, C., H. Lenke, U. Klaus, M. Spiteller, and H.-J. Knackmuss. 2000. Immobilization of TNT in soil as a function of nitro group reduction. Environ. Sci. Technol. submitted.
3. Achtnich, C., P. Pfortner, M. G. Weller, R. Niessner, H. Lenke, and H.-J. Knackmuss. 1999. Immunological detection and reductive transformation of bound trinitrophenyl residues during a biological treatment process. Environ. Sci. Technol. 33:3421-3426
4. Achtnich, C., U. Sieglen, H.-J. Knackmuss, and H. Lenke. 1999. Irreversible binding of biologically reduced metabolites of TNT to soil. Environ. Toxicol. Chem. 18:2416-2423.
5. Alvarez, M. A., L. K. Christopher, J. L. Botsford, and P. J. Unkefer. 1995. Pseudomonas aeruginosa strain MAO1 aerobically metabolizes the aminodinitrotoluene produced by 2,4,6-trinitrotoluene nitro group reduction. Can. J. Microbiol. 41:984-991
6. Behrend, C. and K. Heesche-Wagner. 1999. Formation of hydride-Meisenheimer complexes of picric acid (2,4,6-trinitrophenol) and 2,4-dinitrophenol during mineralization of picric acid by Nocardioides sp. strain CB 22-2. Appl. Environ. Microbiol. 65:1372-1377.
7. Beunik, J. and H.-J. Rehm. 1990. Coupled reductive and oxidative degradation of 4-chloro-2-nitrophenol by a co-immobilized culture system. Appl. Microbiol. Biotechnol. 34:108-115.
8. Blasco, R., E. Moore, V. Wray, D. Pieper, K. Timmis, and F. Castillo. 1999. 3-Nitroadipate, a metabolic intermediate for mineralization of 2,4-dinitrophenol by a new strain of a Rhodococcus species. J. Bacteriol. 181:149-152
9. Bollag, J.-M., R. D. Minard, and S. Y. Liu. 1983. Cross-linkage between anilines and phenolic humus constituents. Environ. Sci. Technol. 17:72-80.
10. de Bont, J. A. M. and W. Harder. 1978. Metabolism of ethylene by Mycobacterium E20. FEMS Microbiol. Lett. 3:89-93.
11. Boopathy, R. and C. F. Kupla. 1993. Nitroaromatic compounds serve as nitrogen source for Desulfovibrio sp. (B. strain). Can. J. Microbiol. 34:430-433.
12. Boopathy, R., J. Manning, and C. F. Kulpa. 1998. A laboratory study of the bioremediation of 2,4,6-trinitrotoluene-contaminated soil using aerobic/anoxic soil slurry reactor. Water Environ. Res. 70:80-86.
13. Boopathy, R., J. Manning, C. Montemagno, and C. F. Kulpa. 1994. Metabolism of 2,4,6-trinitrotoluene by a Pseudomonas consortium under aerobic conditions. Curr. Microbiol. 28:131-137.
14. Brannon, J. M., C. B. Price, and C. Hayes. 1998. Abiotic transformation of TNT in montmorillonite and soil suspensions under reducing conditions. Chemosphere. 36:1453-1462.
15. Bruns-Nagel, D., O. Drzyzga, K. Steinbach, T. C. Schmidt, E. v. Löw, T. Gorontzy, K.-H. Blotevogel, and D. Gemsa. 1998. Anaerobic/aerobic composting of 2,4,6-trinitrotoluene-contaminated soil in a reactor system. Environ. Sci. Technol. 32:1676-1679.
16. Bruns-Nagel, D., T. C. Schmidt, O. Drzyzga, E. v. Löw, and K. Steinbach. 1999. Identification of oxidized TNT metabolites in soil samples of a former ammunition plant. Environ. Sci. Pollut. Res. 6:7-10.
17. Carpenter, D. F., N. G. McCormick, J. H. Cornell, and A. M. Kaplan. 1978. Microbial transformation of 14C-labeled 2,4,6-trinitrotoluene in an activated-sludge system. Appl. Environ. Microbiol. 35:949-954.
18. Caton, J. E., C. Ho, R. T. Williams, and W. H. Griest. 1994. Characterization of insoluble fractions of TNT transformed by composting. J. Environ. Sci. Health A. 29:659-670.
19. Channon, H. J., G. T. Mills, and R. T. Williams. 1944. The metabolism of 2,4,6-trinitrotoluene (α-TNT). Biochem. J. 38:70-85.
20. Daun, G., H. Lenke, F. Desiere, H. Stolpmann, J. Warrelmann, M. Reuss, and H.-J. Knackmuss. 1995. Biological treatment of TNT-contaminated soil by a two-stage anaerobic/aerobic process, p. 337-346. In W. J. van den Brink, R. Bosman, and F. Arendt (eds.), Contaminated Soil ′95, Kluwer Academic Publishers, The Netherlands.
21. Daun, G., H. Lenke, M. Reuss, and H.-J. Knackmuss. 1998. Biological treatment of TNT-contaminated soil I: Anaerobic cometabolic reduction and interaction of TNT and metabolites with soil components. Environ. Sci. Technol. 32:1956-1963.
22. Dawel, G., M. Kästner, J. Michels, W. Poppitz, W. Günther, and W. Fritsche. 1997. Structure of a laccase-mediated product of coupling of 2,4-diamino-6-nitrotoluene to guaiacol, a model for coupling of 2,4,6-trinitrotoluene metabolites to a humic organic matrix. Appl. Environ. Microbiol. 63:2560-2665.
23. Dec, J., K. Haider, A. Schaffer, E. Fernandes, and J.-M. Bollag. 1997. Use of silylation procedure and 13C-NMR spectroscopy to characterize bound and sequestered residues of cyprodinil in soil. Environ. Sci. Technol. 31:2991-2997.
24. DECHEMA. 1995. Bioassays for Soils/Ad-Hoc-Committee “Methods for Toxicological/Ecotoxicological Assessment of Soils.” DECHEMA, Deutsche Gesellschaft für Chemisches Apparatewesen, Chemische Technik und Biotechnologie e.V.
25. Dickel, O., W. Haug, and H.-J. Knackmuss. 1993. Biodegradation of nitrobenzene by a sequential anaerobic-aerobic process. Biodegradation. 4:187-194.
26. Drzyzga, O., D. Bruns-Nagel, T. Gorontzy, K.-H. Blotevogel, and E. v. Löw. 1999. Anaerobic incorporation of the radiolabeled explosive TNT and metabolites into the organic soil matrix of contaminated soil after different treatment procedures. Chemosphere. 38:2081-2095.
27. Drzyzga, O., D. Bruns-Nagel, T. Gorontzy, K.-H. Blotevogel, D. Gemsa, and E. V. Löw. 1998. Mass balance studies with 14C-labeled 2,4,6-trinitrotoluene (TNT) mediated by an anaerobic Desulfovibrio species and an aerobic Serratia species. Curr. Microb. 37:380-386.
28. Drzyzga, O., D. Bruns-Nagel, T. Gorontzy, K.-H. Blotevogel, D. Gemsa, and E. v. Löw. 1998. Incorporation of 14C-labeled 2,4,6-trinitrotoluene metabolites into different soil fractions after anaerobic and anaerobic-aerobic treatment of soil/molasses mixtures. Environ. Sci. Technol. 32:3529-3535.
29. Dunnivant, F. M., R. P. Schwarzenbach, and D. L. Macalady. 1992. Reduction of substituted nitrobenzenes in aqueous solutions containing natural organic matter. Environ. Sci. Technol. 26:2133-2141.
30. Duque, E., A. Haidour, F. Godoy, and J. L. Ramos. 1993. Construction of a Pseudomonas hybrid strain that mineralizes 2,4,6-trinitrotoluene. J. Bacteriol. 175:2278-2283.
31. Ebert, S., P.-G. Rieger, and H.-J. Knackmuss. 1999. Function of coenzyme F420 in aerobic catabolism of 2,4,6-trinitrophenol and 2,4-dinitrophenol by Nocardioides simplex FJ2-1A. J. Bacteriol. 181:2669-2674.
32. Esteve-Núnez, A. and J. L. Ramos. 1998. Metabolism of 2,4,6-trinitrotoluene by Pseudomonas sp. JLR11. Environ. Sci. Technol. 32:3802-3808.
33. Fiorella, P. D. and J. C. Spain. 1997. Transformation of 2,4,6-trinitrotoluene by Pseudomonas pseudoalcaligenes JS52. Appl. Environ. Microbiol. 63:2007-2015.
34. French, C. E., S. Nicklin, and N. C. Bruce. 1998. Aerobic degradation of 2,4,6-trinitrotoluene by Enterobacter cloacae PB2 and by pentaerythritol tetranitrate reductase. Appl. Environ. Microbiol. 64:2864-2868.
35. Funk, S. B., D. J. Roberts, D. L. Crawford, and R. L. Crawford. 1993. Initial-phase optimization for bioremediation of munition compound-contaminated soils. Appl. Environ. Microbiol. 59:2171-2177.
36. Funk, S. B., D. L. Crawford, R. L. Crawford, G. Mead, and W. Davis-Hoover. 1995. Full-scale anaerobic bioremediation of trinitrotoluene contaminated soil. Appl. Biochem. Biotech. 51/52:625-633.
37. Gilcrease, P. C. and V. G. Murphy. 1995. Bioconversion of 2,4-diamino-6-nitrotoluene to a novel metabolite under anoxic and aerobic conditions. Appl. Environ. Microbiol. 61:4209-4214.
38. Haderlein, S. B. and R. P. Schwarzenbach. 1995. Environmental processes influencing the rate of abiotic reduction of nitroaromatic compounds in the subsurface, p. 199-226. In J. C. Spain (ed.), Biodegradation of Nitroaromatic Compounds. Plenum Publishing Co., New York.
39. Haderlein, S. B., K. W. Weissmahr, and R. P. Schwarzenbach. 1993. Adsorption of substituted nitrobenzenes and nitrophenols to mineral surfaces. Environ. Sci. Technol. 27:316-326.
40. Haderlein, S. B., K. W. Weissmahr, and R. P. Schwarzenbach. 1996. Specific adsorption of nitroaromatic explosives and pesticides to clay minerals. Environ. Sci. Technol. 30:612-622.
41. Haider, K., M. Spiteller, A. Wais, and M. Fild. 1993. Evaluation of the binding mechanism of anilazine and its metabolites in soil organic matter. Int. J. Environ. Anal. Chem. 51:125-137.
42. Haider, K., M. Spiteller, K. Reichert, and M. Fild. 1992. Derivatization of humic compounds: an analytical approach for bound organic residues. Int. J. Environ. Anal. Chem. 46:201-212.
43. Haug, W., A. Schmidt, B. Nörtemann, D. C. Hempel, A. Stolz, and H.-J. Knackmuss. 1991. Mineralization of the sulfonated azo dye Mordant Yellow 3 by a 6-aminonaphthalene-2-sulfonate-degrading bacterial consortium. Appl. Environ. Microbiol. 57:3144-3149.
44. Hawari, J., A. Halasz, L. Paquet, E. Zhou, B. Spencer, G. Ampleman, and S. Thiboutot. 1998. Characterization of metabolites in the biotransformation of 2,4,6-trinitrotoluene with anaerobic sludge: role of triaminotoluene. Appl. Environ. Microbiol. 64:2200-2206.
45. Hawari, J., A. Halasz, S. Beaudet, L. Paquet, G. Ampleman, and S. Thiboutot. 1999. Biotransformation of 2,4,6-trinitrotoluene with Phanerochaete chrysosporium in agitated cultures at pH 4.5. Appl. Environ. Microbiol. 65:2977-2986.
46. Hofstetter, T. B., C. G. Heijman, S. B. Haderlein, C. Holliger, and R. P. Schwarzenbach. 1999. Complete reduction of TNT and other (poly)nitroaromatic compounds under iron-reducing subsurface conditions. Environ. Sci. Technol. 33:1479-1487.
47. Isbister, J. D., G. L. Anspach, J. F. Kitchens, and R. C. Doyle. 1984. Composting for decontamination of soils containing explosives. Microbiologica. 7:47-73.
48. Kaplan, D. L. and A. M. Kaplan. 1982. Thermophilic biotransformation of 2,4,6-trinitrotoluene under stimulated composting conditions. Appl. Environ. Microbiol. 44:757-760.
49. Kitts, C. L., D. P. Cunningham, and P. J. Unkefer. 1994. 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. 60:4608-4711.
50. Klaus, U., S. Mohamed, M. Volk, and M. Spiteller. 1998. Interactions of aquatic humic substances with anilazine and its derivatives: the nature of the bound residues. Chemosphere. 37:341-361.
51. Klaus, U., T. Oesterreich, M. Volk, and M. Spiteller. 1998. Interactions of aquatic dissolved organic matter with amitrole and its derivatives: the nature of the bound residues. Acta Hydrochim. Hydrobiol. 26:311-317.
52. Knicker, H. and H.-D. Lüdemann. 1995. N-15 and C-13 CPMAS and solution NMR studies of N-15 enriched plant material during 600 days of microbial degradation. Org. Geochem. 23:329-341.
53. Knicker, H. and I. Kögel-Knabner. 1998. Soil organic nitrogen formation examined by means of NMR spectroscopy. p. 339-357 In B.A. Stankiewicz and P.F. van Bergen (eds.), Fate of Nitrogen Containing Macromolecules in the Biosphere and Geosphere. ACS Symposium Series. American Chemical Society, Washington, D.C.
54. Knicker, H., C. Achtnich, and H. Lenke. 1999. Solid-state 15N NMR spectroscopic investigations on chemical alteration of TNT in soil induced by an anaerobic/aerobic bioremediation process. J. Environ. Qual., submitted.
55. Knicker, H., D. Bruns-Nagel, O. Drzyga, E. v. Löw, and K. Steinbach. 1999. Characterization of 15N-TNT residues after an anaerobic/aerobic treatment of soil/molasses mixtures by solid-state 15N NMR spectroscopy. I. Determination and optimization of relevant NMR spectroscopic parameters. Environ. Sci. Technol. 33:343-349.
56. Koziollek, P., D. Bryniok, and H.-J. Knackmuss. 1999. Ethene as an auxiliary substrate for the cooxidation of cis-1,2-dichloroethene and vinyl chloride. Arch. Microbiol. L172:240-246.
57. Krumholz, L. R., J. Li, W. W. Clarkson, G. G. Wilson, and J. M. Suflita. 1997. Transformations of TNT and related aminotoluenes in groundwater aquifer slurries under different electron-accepting conditions. J. Ind. Microbiol. Biotechnol. 18:161-169.
58. Kudlich, M., P. L. Bishop, H.-J. Knackmuss, and A. Stolz. 1996. Simultaneous anaerobic and aerobic degradation of the sulfonated azo dye Mordant Yellow 3 by immobilized cells from a naphthalenesulfonate-degrading mixed culture. Appl. Microbiol. Biotechnol. 46:597-603.
59. Lendenmann, U., J. C. Spain, and B. F. Smets. 1998. Simultaneous biodegradation of 2,4-dinitrotoluene and 2,6-dinitrotoluene in an aerobic fluidized-bed biofilm reactor. Environ. Sci. Technol. 32:82-87.
60. Lenke, H. and H.-J. Knackmuss. 1992. Initial hydrogenation during catabolism of picric acid by Rhodococcus erythropolis HL 24-2. Appl. Environ. Microbiol. 58:2933-2937.
61. Lenke, H. and H.-J. Knackmuss. 1996. Initial hydrogenation and extensive reduction of substituted 2,4-dinitrophenols. Appl. Environ. Microbiol. 62:748-790.
62. Lenke, H., D. H. Pieper, C. Bruhn, and H.-J. Knackmuss. 1992. Degradation of 2,4-dinitrophenol by two Rhodococcus erythropolis strains, HL 24-1 and HL 24-2. Appl. Environ. Microbiol. 58:2928-2932.
63. Lenke, H., J. Warrelmann, G. Daun, K. Hund, U. Sieglen, U. Walter, and H.-J. Knackmuss. 1998. Biological treatment of TNT-contaminated soil. II. Biological induced immobilization of the contaminants and full-scale application. Environ. Sci. Technol. 32:1964-1971.
64. Leung, K. H., M. Yao, R. Stearns, and S.-H. Lee Chiu. 1995. Mechanism of bioactivation and covalent binding of 2,4,6-trinitroluene. Chem. Biol. Interact. 97:37-51.
65. Lewis, T. A., M. M. Ederer, R. L. Crawford, and D. L. Crawford. 1997. Microbial transformation of 2,4,6-trinitrotoluene. J. Ind. Microbiol. Biotechnol. 18:89-96.
66. Li, A. Z., K. A. Marx, J. Walker, and D. L. Kaplan. 1997. Trinitrotoluene and metabolites binding to humic acid. Environ. Sci. Technol. 31:584-589.
67. Liu, S. Y., R. D. Minard, and J.-M. Bollag. 1987. Soil-catalyzed complexation of the pollutant 2,6-diethylaniline with syringic acid. J. Environ. Qual. 16:48-53.
68. Liu, Y.-Y., A. Y. H. Lu, R. A. Staerns, and S.-H. Lee Chiu. 1992. In vivo covalent binding of [14C]trinitrotoluene to proteins in the rat. Chem. Biol. Interact. 82:1-19.
69. Lotrario, J. B. and S. L. Woods. 1997. Comparison of the correlation of MEP and the free energies of reaction with nitro group reduction of nitrotoluene congeners. Bioremediation J. 1:115-122.
70. McCormick, N. G., F. E. Feeherry, and H. S. Levinson. 1976. Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. Appl. Environ. Microbiol. 31:949-958.
71. McCormick, N. G., J. H. Cornell, and A. M. Kaplan. 1978. Identification of biotrans-formation products from 2,4-dinitrotoluene. Appl. Environ. Microbiol. 35:945-948.
72. McCormick, N. G., J. H. Cornell, and A. M. Kaplan. 1981. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine. Appl. Environ. Microbiol. 42:817-823.
73. Michels, J. and G. Gottschalk. 1994. Inhibition of the lignin peroxidase of Phanerochaete chrysosporium by hydroxylamino-dinitrotoluene, an early intermediate in the degradation of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 60:187-194.
74. Nishino, S. F., J. C. Spain, H. Lenke, and H.-J. Knackmuss. 1999. Mineralization of 2,4and 2,6-dinitrotoluene in soil slurries. Environ. Sci. Technol. 33:1060-1064.
75. Noguera, D. R. and D. L. Freedman. 1996. Reduction and acetylation of 2,4-dinitrotoluene by a Pseudomonas aeruginosa strain. Appl. Environ. Microbiol. 62:2257-2263.
76. Parris, G. E. 1980. Covalent binding of aromatic amines to humates. I. Reaction with carbonyl and quinones. Environ. Sci. Technol. 14:1099-1106.
77. Pennington, J. C., C. A. Hayes, K. F. Myers, M. Ochman, D. Gunnison, D. R. Felt, and E. F. McCormick. 1994. Fate of 2,4,6-trinitrotoluene in a simulated compost system. Chemosphere. 30:429-438.
78. Peres, C. M., H. Naveau, and S. N. Agathos. 1998. Biodegradation of nitrobenzene by its simultaneous reduction into aniline and mineralization of the aniline formed. Appl. Microbiol. Biotechnol. 49:343-349.
79. Perkins, R. E., J. Rajan, and F. S. Sariaslani. 1995. Microbially mediated degradation of nitrogen-containing phenol compounds by single bacterial isolates. U.S. Patent 5,478,743.
80. Perkins, R. E., J. Rajan, and F. S. Sariaslani. 1995. Single bacterial isolates for the degradation of nitrogen-containing phenol compounds. Patent WO 95/24465.
81. Pfortner, P., M. G. Weller, and R. Niessner. 1998. Detection of bound nitroaromatic residues in soil by immunoassay. Fresenius Z. Anal. Chem. 360:781-783.
82. Pfortner, P., M. G. Weller, and R. Niessner. 1998. Immunological method for detection of nitroaromatic residues bound to humic acids. Fresenius J. Anal. Chem. 360:192-198.
83. Preuss, A., J. Fimpel, and G. Diekert. 1993. Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch. Microbiol. 159:345-353.
84. Price, C. B., J. M. Brannon, and C. A. Hayes. 1997. Effect of redox potential and pH on TNT transformation in soil-water slurries. J. Environ. Eng. 123:988-992.
85. Rajan, J., K. Valli, R. E. Perkins, F. S. Sariaslani, S. M. Barns, A.-L. Reysenbach, S. Rehm, M. Ehringer, and N. R. Pace. 1996. Mineralization of 2,4,6-trinitrophenol (picric acid): characterization and phylogenetic identification of microbial strains. J. Ind. Microbiol. 16:319-324.
86. Rieger, P.-G. and H.-J. Knackmuss. 1995. Basic knowledge and perspectives on biodegradation of 2,4,6-trinitrotoluene and related nitroaromatic compounds in contaminated soil, p. 1-18. In J. C. Spain (ed.), Biodegradation of Nitroaromatic Compounds. Plenum Publishing Co., New York.
87. Rieger, P.-G., V. Sinnwell, A. Preuß, W. Francke, and H.-J. Knackmuss. 1999. Hydride-Meisenheimer complex formation and protonation as key reactions of 2,4,6trinitrophenol biodegradation by Rhodococcus erythropolis. J. Bacteriol. 181:1189-1195.
88. Roberts, D. J., F. Ahmad, and S. Pendharkar. 1996. Optimization of an aerobic polishing stage to complete the anaerobic treatment of munitions-contaminated soil. Environ. Sci. Technol. 30:2021-2026.
89. Russ, R., S. Ebert, and H.-J. Knackmuss. 1998. Transformation of picrate and 2,4-dinitrophenol by microorganisms. Abstr. Q-85, p. 435. Abstract 98th Annu. Meet. Am. Soc. Microbiol., Atlanta, GA.
90. Schmidt, T. C., K. Steinbach, E. v. Löw, and G. Stork. 1998. Highly polar metabolites of nitroaromatic compounds in ammunition wastewater. Chemosphere. 37:1079-1091.
91. Schmidt, T. C., M. Petersmann, L. Kaminski, E. v. Löw, and G. Stork. 1997. Analysis of aminobenzoic acids in waste water from a former ammunition plant with HPLC and combined diode array and fluorescence detection. Fresenius Z. Anal. Chem. 357:121-126.
92. Shen, C. F., S. G. Giot, S. Thiboutot, G. Ampleman, and J. Hawari. 1998. Fate of explosives and their metabolites in bioslurry treatment processes. Biodegradation. 8:339-347.
93. Small, F. J. and S. A. Ensign. 1995. Carbon dioxide fixation in the metabolism of propylene and propylene oxide by Arthrobacter strain Py2. J. Bacteriol. 177:6170-6175.
94. Spiess, T., F. Desiere, P. Fischer, J. C. Spain, H.-J. Knackmuss, and H. Lenke. 1998. A novel degradative pathway of 4-nitrotoluene by a Mycobacterium sp. strain. Appl. Environ. Microbiol. 64:446-452.
95. Spiker, J. K., D. L. Crawford, and R. L. Crawford. 1992. Influence of 2,4,6-trinitrotoluene (TNT) concentration on the degradation of TNT in explosive-contaminated soils by the white-rot fungus Phanerochaete chrysosporium. Appl. Environ. Microbiol. 58:3199-3202.
96. Stevenson, F. J. 1989. Humus Chemistry: Genesis, Composition, Reaction. Wiley-Interscience Publ., John Wiley & Sons, New York.
97. Thorn, K. A. 1997. Covalent binding of the reductive degradation products of TNT to humic substances examined by N-15 NMR, p. 305-306. In Abstracts, The 213th ACS National Meeting. American Chemical Society, San Francisco, CA.
98. Thorn, K. A., P. J. Pettigrew, W. S. Goldenberg, and E. J. Weber. 1996. Covalent binding to humic substances. 2. 15N NMR studies of nucleophilic addition reactions. Environ. Sci. Technol. 30:2764-2775.
99. Vanderberg, L. A., J. J. Perry, and P. J. Unkefer. 1995. Catabolism of 2,4,6-trinitro-toluene by Mycobacterium vaccae. Appl. Microbiol. Biotechnol. 42:937-945.
100. Volkel, W., A. Lienrack, and F. Andreux. 1995. Additions-reactions of herbicides and amino-carrying metabolites on methylcatechol, a precursor of humic substances. C. R. Acad. Sci. 320:103-108.
101. Vorbeck, C., H. Lenke, P. Fischer, and H.-J. Knackmuss. 1994. Identification of a hydride-Meisenheimer complex as a metabolite of 2,4,6-trinitrotoluene by a Mycobacterium strain. J. Bacteriol. 176:932-934.
102. Vorbeck, C., H. Lenke, P. Fischer, J. C. Spain, and H.-J. Knackmuss. 1998. Initial reductive reactions in aerobic microbial metabolism of 2,4,6-trinitrotoluene. Appl. Environ. Microbiol. 64:246-252.
103. Weber, E. J., M. S. Elcovitz, D. G. Truhlar, J. C. Cramer, and S. E. Barrows. 1996. Factors controlling regioselectivity in the reduction of polynitroaromatics in aqueous solution. Environ. Sci. Technol. 30:3028-3038.
104. Weissmahr, K. W., S. B. Haderlein, and R. P. Schwarzenbach. 1998. Complex formation of soil minerals with nitroaromatic explosives and other π-acceptors. Soil Sci. Soc. Am. J. 62:369-378.
105. Widrig, D. L., R. Boopathy, and J. F. Manning. 1997. Bioremediation of TNTcontaminated soil: a laboratory study. Environ. Toxicol. Chem. 16:1141-1148
106. Ziechmann, W. 1994. Huminstoffe. Verlag Chemie, Weinheim.