Characterization of non-extractable ¹⁴C- and ¹³C-sulfadiazine residues in soil including simultaneous amendment of pig manure

References

• Gustafson , R. H. and Bowen , R. E. 1997 . Antibiotic use in animal agriculture . J. Appl. Microbiol. , 83 : 531 – 541 .
   PubMed Web of Science ®Google Scholar
• Boxall , A.B. A. , Fogg , L. A. , Blackwell , P. A. , Kay , P. , Pemberton , E. J. and Croxford , A. 2004 . Veterinary medicines in the environment . Rev. Environ. Contam. Toxicol. , 180 : 1 – 91 .
   PubMed Web of Science ®Google Scholar
• Boxall , A.B. A. 2004 . The environmental side effects of medication . EMBO Reports , 5 : 1110 – 1116 .
   PubMed Web of Science ®Google Scholar
• Sarmah , A. K. , Meyer , M. T. and Boxall , A.B. A. 2006 . A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment . Chemosphere , 65 : 725 – 759 .
   PubMed Web of Science ®Google Scholar
• Schauss , K. , Focks , A. , Heuer , H. , Kotzerke , A. , Schmitt , H. , Thiele-Bruhn , S. , Smalla , K. , Wilke , B.-M. , Matthies , M. , Amelung , W. , Klasmeier , J. and Schloter , M. 2009 . Analysis, fate and effects of antibiotic sulfadiazine in soil ecosystems . Trends Anal. Chem. , 28 : 612 – 618 .
   Web of Science ®Google Scholar
• Yang , J.-F. , Ying , G.-G. , Yang , L.-H. , Zhao , J.-L. , Liu , F. , Tao , R. , Yu , Z.-Q. and Peng , P. A. 2009 . Degradation behavior of sulfadiazine in soils under different conditions . J. Environ. Sci. Health Part B , 44 : 241 – 248 .
   PubMed Web of Science ®Google Scholar
• Thiele-Bruhn , S. 2003 . Pharmaceutical antibiotic compounds in soils—a review . J. Plant Nutr. Soil Sci. , 166 ( 2 ) : 145 – 167 .
   Web of Science ®Google Scholar
• Lamshöft , M. , Sukul , P. , Zühlke , S. and Spiteller , M. 2007 . Metabolism of 14C-labelled and non-labelled sulfadiazine after administration to pigs . Anal. Bioanal. Chem. , 388 : 733 – 1745 .
   PubMed Web of Science ®Google Scholar
• Christian , T. , Schneider , R. J. , Farber , H. A. , Skutlarek , D. , Meyer , M. T. and Goldbach , H. E. 2003 . Determination of antibiotic residues in manure, soil, and surface waters . Acta Hydrochim. Hydrobiol. , 31 : 36 – 44 .
   Google Scholar
• Schmidt , B. , Ebert , J. , Lamshöft , M. , Thiede , B. , Schumacher-Buffel , R. , Ji , R. , Corvini , P.F.-X. and Schäffer , A. 2008 . Fate in soil of 14C-sulfadiazine residues contained in manure of young pigs which were treated with the veterinary antibiotic . J. Environ, Sci. Health Part B , 43 : 8 – 20 .
   PubMed Web of Science ®Google Scholar
• Förster , M. , Laabs , V. , Lamshöft , M. , Groeneweg , J. , Zühlke , S. , Spiteller , M. , Krauss , M. , Kaupenjohann , M. and Amelung , W. 2009 . Sequestration of manure-applied sulfadiazine residues in soils . Environ. Sci. Technol. , 43 : 1824 – 1830 .
   PubMed Web of Science ®Google Scholar
• Kreuzig , R. and Höltge , S. 2005 . Investigation on the fate of sulfadiazine in manured soil: laboratory experiments and test-plot studies . Environ. Toxicol. Chem. , 24 ( 4 ) : 771 – 776 .
   PubMed Web of Science ®Google Scholar
• Heise , J. , Höltge , S. , Schrader , S. and Kreuzig , R. 2006 . Chemical and biological characterization of non-extractable sulphonamide residues in soil . Chemosphere , 65 ( 11 ) : 2352 – 2357 .
   PubMed Web of Science ®Google Scholar
• Heuer , H. , Focks , A. , Lamshöft , M. , Smalla , K. , Matthies , M. and Spiteller , M. 2008 . Fate of sulfadiazine administered to pigs and its quantitative effect on the dynamics of bacterial resistance genes in manure and manured soil . Soil Biol. Biochem. , 40 : 1892 – 1900 .
   Web of Science ®Google Scholar
• Stoob , K. , Singer , H. P. , Stettler , S. , Hartmann , N. , Mueller , S. R. and Stamm , C. H. 2006 . Exhaustive extraction of sulfonamide antibiotics from aged agricultural soils using pressurized liquid extraction . J. Chromatogr. A. , 1128 : 1 – 9 .
   PubMed Web of Science ®Google Scholar
• Förster , M. , Laabs , V. , Lamshöft , M. , Pütz , T. and Amelung , W. 2008 . Analysis of aged sulfadiazine residues in soils using microwave extraction and liquid chromatography tandem mass spectrometry . Anal. Bioanal. Chem. , 391 : 1029 – 1038 .
   PubMed Web of Science ®Google Scholar
• Pignatello , J. J. 1990 . Slowly reversible sorption of aliphatic hydrocarbons in soils . I. Formation of residual fractions. Environ. Toxicol. Chem. , 9 : 1107 – 1115 .
   Web of Science ®Google Scholar
• Pignatello , J. J. 1990 . Slowly reversible sorption of aliphatic hydrocarbons in soils . II. Mechanistic aspects. Environ. Toxicol. Chem. , 9 : 1117 – 1126 .
   Web of Science ®Google Scholar
• Roberts , T. R. 1984 . Non-extractable pesticide residues in soils and plants . Pure Appl. Chem. , 56 : 945 – 956 .
   Web of Science ®Google Scholar
• Gevao , B. , Semple , K. T. and Jones , K. C. 2000 . Bound pesticide residues in soils: a review . Environ. Poll. , 108 : 3 – 14 .
   PubMed Web of Science ®Google Scholar
• Barraclough , D. , Kearney , T. and Croxford , A. 2005 . Bound residues: environmental solution or future problem? Environ . Poll. , 133 : 85 – 90 .
   PubMed Web of Science ®Google Scholar
• Dec , J. , Haider , K. , Benesi , A. , Rangaswamy , V. , Schäffer , A. , Plücken , U. and Bollag , J.-M. 1997 . Analysis of soil-bound residues of 13C-labeled fungicide cyprodinil by NMR spectroscopy . Environ. Sci. Technol. , 31 : 1128 – 1135 .
   Web of Science ®Google Scholar
• Dec , J. , Haider , K. , Schäffer , A. , Fernandes , E. and Bollag , J.-M. 1997 . Use of a silylation procedure and 13C-NMR spectroscopy to characterize bound and sequestered residues of cyprodinil in soil . Environ. Sci. Technol. , 31 : 2991 – 2997 .
   Web of Science ®Google Scholar
• Heizmann , P. and Haefelinger , P. 1980 . Dünnschicht-chromatografische Bestimmung von Sulfadiazin und Sulfamethoxazol in Urin und Plasma . Fresenius Z. Anal. Chem. , 302 : 410 – 412 .
   Google Scholar
• Atef , M. and Nielsen , P. 1975 . Metabolism of sulfadiazine in goats . Xenobiotica , 5 : 167 – 172 .
   PubMed Web of Science ®Google Scholar
• Ganapathi , K. , Deliwala , C. V. and Shirsat , M. V. 1942 . Chemotherapy of baceterial infections . Part VII. Synthesis of sulphanilamide derivatives of the pyrimidine group. Proc. Indian Acad. Sci. A , 16 : 115 – 125 .
   Google Scholar
• DeRuiter , J. , Swearingen , B. E. , Wandrekar , V. and Mayfield , C. A. 1989 . Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety . J. Med. Chem. , 32 : 1033 – 1038 .
   PubMed Web of Science ®Google Scholar
• Ramaswami , V. and Tirrell , D. 1989 . Synthesis of a cleavable heterobifunctional photolabeling reagent: ring-labeled 3-[(4-azidophenyl)dithio]propionic acid-14C . J. Label. Compd. Radiopharm. , 27 : 889 – 899 .
   Web of Science ®Google Scholar
• Gannett , P. M. , Johnson , E. M. II , Grimes , M. A. , Myers , A. L. , Deavers , R. E. III and Tracy , T. S. 2003 . Synthesis of deuterated 4,4′-diaminodiphenylsulfone (Dapsone) and related analogs . J. Label. Compd. Radiopharm. , 46 : 107 – 114 .
   Web of Science ®Google Scholar
• Hoellinger , H. , Nguyen-Hoang , N. and Pichat , L. 1973 . Synthese de la sulfadiazine et de ses derives: la (N4-acetylsulfanilamido)-2 pyrimidine, la (benzenesulfonamido)-2 pyrimidine et la (p-toluenesulfonamido)-2 pyrimidine marquees par le 14C dans le noyau pyrimidine . J. Label. Compd. , 9 : 161 – 165 .
   Web of Science ®Google Scholar
• Nguyen-Hoang , N. , Herbert , M. , Nguyen-Dat , X. and Pichat , L. 1971 . Synthèse de l'amino-2 pyrimidine 14C-2; de la N4-di(chloro-2 n-propyl) sulfadiazine (pyrimidine 14C-2) ou CB 1932 14C . J. Label. Compd. , 7 : 299 – 304 .
   Web of Science ®Google Scholar
• Kreuzig , R. 2010 . The reference manure concept for transformation tests of veterinary medicines and biocides in liquid bovine and pig manure . Clean: Soil, Air, Water , 38 ( 8 ) : 697 – 705 .
   Web of Science ®Google Scholar
• Kreuzig , R. , Hartmann , C. , Teigeler , J. , Cvetkoviæ , B. , Schlag , P. and Höltge , S. 2010 . Development of a novel concept for fate monitoring of biocides in manure and manured soil taking 14C-imazalil as an example . Chemosphere , 79 : 1089 – 1094 .
   PubMed Web of Science ®Google Scholar
• Zielezny , Y. , Groeneweg , J. , Vereecken , H. and Tappe , W. 2006 . Impact of sulfadiazine and chlorotetracycline on soil bacterial community structure and respiratory activity . Soil Biol. Biochem. , 38 : 2372 – 2380 .
   Web of Science ®Google Scholar
• Aiken , G.R. , Thurman , E.M. , Malcolm , R. L. and Walton , H. F. 1979 . Comparison of XAD macroporous resins for the concentration of fulvic acid from aqueous solution . Anal. Chem. , 51 : 1799 – 1803 .
   Web of Science ®Google Scholar
• Zwiener , C. , Kumka , M. U. , Abbt-Braun , G. and Frimmel , F. H. 1999 . Adsorbed and bound residues in fulvic acid fractions of a contaminated groundwater—isolation, chromatographic and spectroscopic characterization . Acta Hydrochim. Hydrobiol. , 27 : 208 – 213 .
   Google Scholar
• Hayes , M.H. B. 1970 . Adsorption of triazine herbicides on soil organic matter, including a short review on soil organic matter chemistry . Res. Rev. , 32 : 131 – 174 .
   PubMedGoogle Scholar
• Thurman , E. M. and Malcolm , R. L. 1983 . “ Structural study of humic substances: new approaches and methods ” . In Aquatic and Terrestrial Humic Materials , Edited by: Christman , R. F. and Gjessing , E. T. 1 – 23 . Ann Arbor, MI : Ann Arbor Science Publishers .
   Google Scholar
• Thiele-Bruhn , S. , Seibicke , T. , Schulten , H.-R. and Leinweber , P. 2004 . Sorption of sulfonamide pharmaceutical antibiotics on whole soils and particle-size fractions . J. Environ. Qual. , 33 : 1331 – 1342 .
   PubMed Web of Science ®Google Scholar
• Sukul , P. , Lamshöft , M. , Zühlke , S. and Spiteller , M. 2008 . Sorption and desorption of sulfadiazine in soil and soil-manure systems . Chemosphere , 73 : 1344 – 1350 .
   PubMed Web of Science ®Google Scholar
• Khan , S. U. 1982 . Bound pesticide residues in soil and plants . Res. Rev. , 84 : 1 – 25 .
   PubMedGoogle Scholar
• Bialk , H. M. , Simpson , A. I. and Pedersen , J. A. 2005 . Cross-coupling of sulfonamide antimicrobial agents with model humic constituents . Environ. Sci. Technol. , 39 : 4463 – 4473 .
   PubMed Web of Science ®Google Scholar
• Bialk , H.M. , Simpson , A.I. and Pedersen , J. A. 2007 . Laccase-mediated Michael addition of 15N-sulfapyridine to a model humic constituent . Environ. Sci. Technol. , 41 : 3593 – 3600 .
   PubMed Web of Science ®Google Scholar
• Bialk , H. M. and Pedersen , J. A. 2008 . NMR investigation of enzymatic coupling of sulfonamide antimicrobials with humic substances . Environ. Sci. Technol. , 42 : 106 – 112 .
   PubMed Web of Science ®Google Scholar
• Gulkowska , A. , Hollender , J. and Krauss , M. 2010 . “ Covalent bonding of sulfonamide antimicrobials with organic matter: dominace of nucleophilic addition over radical coupling ” . In Society of Environmental Toxicology and Chemistry (SETAC) Europe—20 ^th Annual Meeting, Sevilla 2010, Abstract Book , Spain : Sevilla . May 23–27, SETAC Europe Office: Brussels, 2010; EC06A-4
   Google Scholar