Transformation products of 2-benzoxazolinone (BOA) in soil

Chemosphere

Volumn 61, Issue 1, 2005, Pages 74-84

  Gents, Mia B ^a   Nielsen, Susan T ^a   Mortensen, Anne G ^a   Christophersen, Carsten ^b   Fomsgaard, Inge S ^a  

^a DANISH INSTITUTE OF AGRICULTURAL SCIENCES   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

2 Aminophenyl acetate; 6 hydroxy benzoxazolin (3H) one; Allelochemicals; Degradation; Identification; LC MS; N (2 hydroxyphenyl)malonamic acid

Indexed keywords

CARBOXYLIC ACIDS; CONCENTRATION (PROCESS); DEGRADATION; DISEASES; METABOLISM; SOILS; SYNTHESIS (CHEMICAL);

2-AMINOPHENYL ACETATE; 6-HYDROXY-BENZOXAZOLINONE-(3H)-ONE; ALLELOCHEMICALS; IDENTIFICATION; LC-MS;

NITROGEN COMPOUNDS;

2 ACETYLAMINO 3H PHENOXAZIN ONE; 2 AMINO 3H PHENOXAZIN 3 ONE; 2 BENZOXAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ALLELOCHEMICAL; SOIL TYPE;

ARTICLE; CONCENTRATION (PARAMETERS); DEGRADATION; SOIL;

EID: 21044446456     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2005.03.068     Document Type: Article

References (40)

1. O.A. Andersen, T. Flatmark, and E. Hough Crystal structure of the ternary complex of the catalytic domain of human phenylalanine hydroxylase with tetrahydrobiopterin and 3-(2-thienyl)-l-alanine and its implications for the mechanism of catalysis and substrate activation J. Mol. Biol. 320 2002 1095 1108
2. J.P. Barnes, and A.R. Putnam Role of benzoxazinones in allelopathy by rye (Secale cereale L.) J. Chem. Ecol. 13 1987 889 906
3. J.P. Barnes, A.R. Putnam, and B.A. Burke Allelopathic activity of rye (Secale cereale L.) A.R. Putnam C.S. Tang The Science of Allelopathy 1986 John Wiley & Sons New York 271 286
4. A. Chang, and T. Hartmann Solubilization and characterization of a senecionine N-oxygenase from Crotalaria scassellatii seedlings Phytochemistry 49 1998 1859 1866
5. Coja, T., 2004. Effects of wheat allelochemicals on carabid beetle larvae as non target soil organisms. Proceedings, Second European Allelopathy Symposium. Allelopathy - from understanding to application. FATEALLCHEM Workshop ("Fate and Toxicity of Allelochemicals (Natural Plant Toxins) in Relation to Environment and Consumer), Pulawy, Poland, June 3-5, 2004. Institute of Soil Science and Plant Cultivation, Pulawy, Poland, p. 69.
6. N.G. Creamer, M.A. Bennett, B.R. Stinner, J. Cardina, and E.E. Regnier Mechanisms of weed suppression in cover crop-based production systems Hort. Sci. 31 1996 410 413
7. J.E. Foglesong, and I.L. Newell The reduction of mononitropyrocatechols J. Am. Chem. Soc. 52 1930 834 837
8. I.S. Fomsgaard, A.G. Mortensen, and S.C.K. Carlsen Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals - A review Chemosphere 54 2004 1025 1038
9. A. Friebe, I. Wieland, and M. Schultz Tolerance of Avena sativa to the allelochemical benzoxazolinone. Degradation of BOA by root-colonizing bacteria J. Appl. Bot. 70 1996 150 154
10. A. Friebe, V. Vilich, L. Hennig, M. Kluge, and D. Sicker Detoxification of benzoxazolinone allelochemicals from wheat by Gaeumannomyces graminis var. tritici, G. graminis var. graminis, G. graminis var. avenae, and Fusarium culmorum Appl. Environ. Microbiol. 64 1998 2386 2391
11. Fritz, J., Bauer, M., Pruckner, M., Braun, R., 2004. Ecotoxic effects of hydroxamic acid allelochemicals and selected degradation products on aquatic organisms. Proceedings, Second European Allelopathy Symposium. Allelopathy - from understanding to application. FATEALLCHEM Workshop ("Fate and Toxicity of Allelochemicals (Natural Plant Toxins) in Relation to Environment and Consumer), Pulawy, Poland, June 3-5, 2004. Institute of Soil Science and Plant Cultivation, Pulawy, Poland, pp. 72-74.
12. B.S. Furniss, A.J. Hannaford, P.W.G. Smith, and A.R. Tatchell Vogel's Textbook of Practical Organic Chemistry 1996 Addison-Wesley Pub. Co. p. 1398
13. R.W. Gagliardo, and W.S. Chilton Soil transformation of 2-(3H)-Benzoxazolone of rye into phytotoxic 2-amino-(3H)-phenoxazin-3-one J. Chem. Ecol. 18 1992 1683 1691
14. A.E. Glenn, S.E. Gold, and C.W. Bacon Fdb1 and Fdb2, Fusarium verticillioides loci necessary for detoxification of preformed antimicrobials from corn Mol. Plant Microbe Interactions 15 2002 91 101
15. Idinger, J., 2004. Effects of wheat allelochemicals as standard non target soil test organism. Proceedings, Second European Allelopathy Symposium. Allelopathy - from understanding to application. FATEALLCHEM Workshop ("Fate and Toxicity of Allelochemicals (Natural Plant Toxins) in Relation to Environment and Consumer), Pulawy, Poland, June 3-5, 2004. Institute of Soil Science and Plant Cultivation, Pulawy, Poland, p. 70.
16. S.D. Kinzie, N. Thevis, K. Ngo, J. Whitelegge, J.A. Loo, and M.M. Abu-Omar Posttranslational hydroxylation of human phenylalanine hydroxylase is a novel example of enzyme self-repair within the second coordination sphere of catalytic iron J. Am. Chem. Soc. 125 2003 4710 4711
17. B.M. Koch, O. Sibbesen, B.A. Halkier, I. Svendsen, and B.L. Møller The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of l-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench Arch. Biochem. Biophys. 323 1995 177 186
18. Kudsk, P., Chunhong, J., Mathiassen, S.K., 2004. Joint action of wheat allelochemicals. Proceedings, Second European Allelopathy Symposium. Allelopathy - from understanding to application. FATEALLCHEM Workshop ("Fate and Toxicity of Allelochemicals (Natural Plant Toxins) in Relation to Environment and Consumer), Pulawy, Poland, June 3-5, 2004. Institute of Soil Science and Plant Cultivation, Pulawy, Poland, pp. 83-84.
19. 2BOA into aminophenoxazinones J. Chem. Ecol. 19 1993 2453 2461
20. V. Leighton, H.M. Niemeyer, and L.M.V. Jonsson Substrate specificity of a glucosyltransferase and an N-hydroxylase involved in the biosynthesis of cyclic hydroxamic acids in gramineae Phytochemistry 36 1994 887 892
21. A. Maas, J. Scholz, and A. Moser Modeled ligand-protein complexes elucidate the origin of substrate specificity and provide insight into catalytic mechanisms of phenylalanine hydroxylase and tyrosine hydroxylase Eur. J. Biochem. 270 2003 1065 1075
22. Macías, F.A., Oliveros-Bastidas, A., Marín, D., Castellano, D., Simonet, A.M., Molinillo, J.M.G., 2004. Degradation studies on benzoxazinoids. Part 1: evaluation of DIBAO transformations in soil. Submitted.
23. Martyniuk, S., Stochmal, A., Macías, F.A., Marín, D., Molinilllo, J.M.G., Oleszek, W., 2004. Effect of hydroxamic acids on wheat infesting fungi (Gaumannomyces graminins var. tritici, Fusarium culmorum, Cephalosporium gramineum). Proceedings, Second European Allelopathy Symposium. Allelopathy - from understanding to application. FATEALLCHEM Workshop ("Fate and Toxicity of Allelochemicals (Natural Plant Toxins) in Relation to Environment and Consumer), Pulawy, Poland, June 3-5, 2004. Institute of Soil Science and Plant Cultivation, Pulawy, Poland, pp. 85-87.
24. A.W. Munro, D.G. Leys, K.J. McLean, K.R. Marshall, T.W.B. Ost, S. Daff, C.S. Miles, S.K. Chapmann, D.A. Lysek, C.C. Moser, C.C. Page, and P.L. Dutton P450BM3: The very model of a modern flavocytochrome Trends Biochem. Sci. 27 2002 250 257
25. V.N. Mwaja, J.B. Masiunas, and L.A. Weston Effects of fertility on biomass, phytotoxicity, and allelochemical content of cereal rye J. Chem. Ecol. 21 1995 81 96
26. C. Naumann, T. Hartmann, and D. Ober Evolutionary recruitment of a flavin-dependent monooxygenase for the detoxification of host plant-acquired pyrrolizidine alkaloids in the alkaloid-defended arctiid moth Tyria jacobaeae Proc. Natl. Acad. Sci. USA 99 2002 6085 6090
27. H.M. Niemeyer Hydroxamic acids (4-hydroxy-1,4-benzoxazin-3-ones), defence chemicals in the Gramineae Phytochemistry 27 1988 3349 3358
28. H. Takeuchi, and K. Koyama Photolysis and thermolysis of phenyl azide in acetic acid. Trapping of 1-azacyclohepta-1,2,4,6-tetraene and nucleophilic aromatic substitution J. Chem. Soc. Perkin Trans. I 1982 1269 1273
29. Torres, A., Olivia, R.M., Castellano, D., Cross, P.I., 1996. Introduction. In: Proceedings of the First World Congress on Alleopathy - a Science for the Future. September 16-20, 1996, Cadiz, Spain.
30. A.G. Understrup, I.S. Fomsgaard, S. Ravnskov, and H.C.B. Hansen Biotransformation of 2-benzoxazolinone to 2-amino-phenoxazin-3-one and 2-acetylamino-phenoxazin-3-one in soil J. Chem. Ecol. 31 2005 1205 1222
31. V. Vilich, B. Löhndorf, R.A. Sikora, and A. Friebe Metabolism af Benzoxazolinone allelochemicals of Zea mays by Fusarium subglutinans Mycol. Res. 103 1999 1529 1532
32. J. Wang, M. Ortiz-Maldonado, B. Entsch, V. Massey, D. Ballou, and D.L. Gatti Protein and ligand dynamics in 4-hydroxybenzoate hydroxylase Proc. Natl. Acad. Sci. USA 99 2002 608 613
33. Wieland, I., Friebe, A., Kluge, M., Sicker, D., Schulz, M., 1999. Detoxification of benzoxazolin-2(3H)-one in higher plants. In: Macías, F.A., Galindo, J.C.G., Molinillo, J.M.G., Cutler, H.G. (Eds.), Recent Advances in Allelopathy. Vol. I. A Science for the Future, pp. 47-56.
34. U. Wittstock, and B.A. Halkier Cytochrome P450 CYP792A from Arabidopsis thaliana L. Catalyzes the conversion of l-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate J. Biol. Chem. 275 2000 14659 14666
35. D. Xu, C. Enroth, Y. Lindquist, D.P. Ballou, and V. Massey Studies of the mechanism of phenol hydroxylase: Effect of mutation of proline 364 to serine Biochemistry 41 2002 13627 13636
36. J.P. Yenish, A.D. Worsham, and W.S. Chilton Disappearance of DIBOA-glucoside, DIBOA, and BOA from rye (Secale cereale L.) cover crop residue Weed Sci. 43 1995 18 20
37. Q. Yue, C.W. Bacon, and M.D. Richardson Biotransformation of 2-benzoxazolinone and 6-methoxy-benzoxazolinone by Fusarium Monoliforme Phytochemistry 48 1998 451 454
38. Y. Zheng, J. Dong, B.A. Palfey, and P.R. Carey Using Raman spectroscopy to monitor the solvent-exposed and buried forms of flavin in p-hydroxybenzoate hydrolase Biochemistry 38 1999 16727 16732
39. M. Zikmundová, K. Drandarov, M. Hesse, and C. Werner Hydroxylated 2-amino-(3H)-phenoxazin-3-one derivates as products of 2-hydroxy-1,4-benzoxazin- 3-one (HBOA) biotransformation by Chaetophaeria sp., an Endophytic Fungus from Aphelandra tetragona Zeit. Nat. 57c 2002 660 665
40. M. Zikmundová, K. Drandarov, L. Bigler, M. Hesse, and C. Werner Biotransformation of 2-benzoxazolinone and 2-hydroxy-1,4-benzoxazin-3-one by endophytic fungi isolated from Aphelandra tetragona Appl. Environ. Microbiol. 68 2002 4863 4870