Ecotoxicological effects of benzoxazinone allelochemicals and their metabolites on aquatic nontarget organisms

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 4, 2006, Pages 1105-1110

  Fritz, Jona Ines ^a   Braun, Rudolf ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

Author keywords

Aquatic ecotoxicity; Benzoxazinones; Daphnia; Freshwater algae; Luminescent bacteria; Secondary metabolites

Indexed keywords

2,4 DIHYDROXY 7 METHOXY 1,4 BENZOXAZIN 3 ONE; 2,4-DIHYDROXY-7-METHOXY-1,4-BENZOXAZIN-3-ONE; 6 METHOXY 2 BENZOXAZOLINONE; 6-METHOXYBENZOXAZOLINONE; BENZOXAZOLE DERIVATIVE; BENZOXAZOLONE; OXAZINE DERIVATIVE; PHEROMONE;

ANIMAL; ARTICLE; CHEMISTRY; DAPHNIA; DRUG EFFECT; GREEN ALGA; METABOLISM; VIBRIO FISCHERI; WHEAT;

ALGAE, GREEN; ANIMALS; BENZOXAZOLES; DAPHNIA; OXAZINES; PHEROMONES; TRITICUM; VIBRIO FISCHERI;

ALGAE; BACTERIA (MICROORGANISMS); CLADOCERA; DAPHNIA; SIPHONAPTERA (FLEAS); TRITICUM AESTIVUM;

EID: 33644871229     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050917n     Document Type: Article

References (24)

1. Korte, F. Lehrbuch der Ökologischen Chemie (Ecological Chemistry); Thieme: Stuttgart, Germany, 1992.
2. Macías, F.; Galindo, J. C. G.; Molinillo, J. M. G.; Cutler, H. C. Allelopathy: Chemistry and Mode of Action of Allelochemicals; CRC Press: Boca Raton, FL, 2004.
3. Fomsgaard, I. S.; Mortensen, A. G.; Carlsen, S. C. K. Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals - a review. Chemosphere 2004, 54, 1025-1038.
4. Zikmundová, M.; Drandarov, K.; Bigler, L.; Hesse, M.; Werner, C. Biotransformation of 2-benzoxazolinone and 2-hydroxy-1,4-benzoxazin-3-one by endophytic fungi isolated from Aphelandra tetragona. Appl. Environ. Microbiol. 2002, 68, 4863-4870.
5. Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Chinchilla, D.; Simonet, A. M.; Molinillo, J. M. G. Isolation and synthesis of allelochemicals from Gramineae: benzoxazinones and related compounds. J. Agric. Food Chem. 2006, 54, 991-1000.
6. Bellinger, E. G. A Key to Common Algae-Freshwater, Estuarine and Some Coastal Species, 4th ed.; Institution of Water and Environmental Management: London, U.K., 1992.
7. Fritz, J. Ecotoxicity of biodegradable materials during and after the degradation process. Ph.D. Thesis, University of Applied Sciences, Vienna, Austria, 1999.
8. Fendt, K. Ökotoxikologie (Ecotoxicology); Thieme: Stuttgart, Germany, 1998.
9. Rippen, G. Handbook of Environmental Chemicals, loose-leaf book, ecomed; Landsberg/Lech: 1984-2001.
10. Cronin, M. T. D.; Bower, G. S.; Sinks, G. D.; Schultz, T. W. Structure-relationships for aliphatic compounds encompassing a variety of mechanisms of toxic action to Vibrio fischeri. SAR QSAR Environ Res. 2000, 11, 301-312.
11. Blaise, C. Micromethod for acute aquatic toxicity assessment using the green alga Selenastrum capricornutum. Toxicity Assess. 1986, 1, 377-385.
12. OECD. Draft Guidance Document on the Statistical Analysis of Ecotoxicity Data; Paris, France, 2003.
13. Guillamón, M.; Villagrasa, M.; Eljarrat, E.; Barceló, D. Development of a liquid chromatography electrospray-mass spectrometric method for the simultaneous analysis of benzoxazolinones and their degradation products. J. Chromatogr. A 2004, 1052, 53-59.
14. Zikmundova, M.; Drandarov, K.; Bigler, L.; Hesse, M.; Werner, C. Biotransformation of 2-benzoxazolinone (BOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) by endophytic fungi isolated from Aphelandra tetragona. Appl. Environ. Microbiol. 2002, 68, 4863-4870.
15. Friebe, A.; Wieland, I.; Schulz, M. Tolerance of Avena sativa to the allelochemical benzoxazolinone. Degradation of BOA by root-colonizing bacteria. J. Appl. Bot. 1996, 70, 150-154.
16. 3]-MBOA in soil. J. Agric. Food Chem. 2006, 54, 1075-1085.
17. Fomsgaard, I. S.; Mortensen, A. G.; Coja, T.; Idinger, J.; Blümel, S. Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida. J. Agric. Food Chem. 2006, 54, 1086-1092.
18. Gents, M. B.; Nielsen, S. T.; Mortensen, A. G.; Christophersen, C.; Fomsgaard, I. S. Transformation products of 2-benzoxazolinone (BOA) in soil. Chemosphere 2005, 61, 74-84.
19. Understrup, A. G.; Ravnskov, S.; Hansen, H. C. B.; Fomsgaard, I. S. Biotransformation of 2-benzoxazolinone to 2-aminophenoxazin-3-one and 2-acetylamino-phenoxazin-3-one in soil. J. Chem. Ecol. 2005, 31, 1205-1222.
20. Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Structure-activity relationships (SAR) studies of benzoxazinones, their degradation products and analogues. Phytotoxicity on standard target species (STS). J. Agric. Food Chem. 2005, 53, 538-548.
21. Macías, F. A.; Marín, D.; Oliveros-Bastidas, A.; Castellano, D.; Simonet, A. M.; Molinillo, J. M. G. Structure-activity relationships (SAR) studies of benzoxazinones, their degradation products and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud. J. Agric. Food Chem. 2006, 54, 1040-1048.
22. DIN-DEV. German Standardized Methods for Water, Wastewater and Sludge Analysis; Deutsches Institut für Normung: Berlin, Germany, 2002.
23. OECD. Guidelines for the Testing of Chemicals, Vol. 1, Sect. 2, Effects on Biotic Systems; Paris, France, 1992.
24. Steinberg, C.; Klein, J.; Brüggemann, R. Ökotoxikologische Testverfahren (test methods in ecotoxicology), ecomed; Landsberg/Lech: 1995.