caa a22 4500 606220321 CHVBK 20210128101123.0 cr unu---uuuuu 210128e20150801xx s 000 0 eng 10.1007/s11104-015-2485-6 doi (NATIONALLICENCE)springer-10.1007/s11104-015-2485-6 Soil biodegradation of a benzoxazinone analog proposed as a natural products-based herbicide [Elektronische Daten] [Nuria Chinchilla, David Marín, Alberto Oliveros-Bastidas, José Molinillo, Francisco Macías] Aims: Benzoxazinones with the 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one skeleton have been proposed as potentially successful models for the development of novel design leads. D-DIBOA has proven to be the most promising base structure in the search for novel herbicide models based on the benzoxazinone skeleton. The biodegradation dynamics of D-DIBOA in soil are therefore relevant and are the subject of this study. Methods: A previously optimized methodology for the assessment of biodegradation has been applied for the first time to a synthetic benzoxazinone. Results: Biodegradability is a characteristic of natural benzoxazinones and a safety requirement for the development of herbicidal chemicals. The biodegradation phenomenon and its consequences for the development of new herbicide models are discussed. The half-life determined for D-DIBOA was much higher than those previously reported for the natural products DIBOA, DIMBOA and their benzoxazolinone derivatives. Conclusions: This finding, together with its previously described potent phytotoxicity, suggests that D-DIBOA is a useful candidate for novel herbicide model development. The lactam D-HBOA, which is slightly less phytotoxic than its precursor, was discovered to be the first and principal metabolite resulting from D-DIBOA degradation. Springer International Publishing Switzerland, 2015 D-DIBOA nationallicence Benzoxazinones nationallicence Degradation study nationallicence Soil nationallicence Herbicide models nationallicence Chinchilla Nuria Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut Marín David Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut Oliveros-Bastidas Alberto Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut Molinillo José Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut Macías Francisco Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut Plant and Soil Springer International Publishing 393/1-2(2015-08-01), 207-214 0032-079X 393:1-2<207 2015 393 11104 https://doi.org/10.1007/s11104-015-2485-6 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s11104-015-2485-6 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Chinchilla Nuria Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut NATIONALLICENCE 700 1- Marín David Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut NATIONALLICENCE 700 1- Oliveros-Bastidas Alberto Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut NATIONALLICENCE 700 1- Molinillo José Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut NATIONALLICENCE 700 1- Macías Francisco Allelopathy Group, Department of Organic Chemistry, School of Sciences, Institute of Biomolecules (INBIO), University of Cadiz, C/ República Saharaui, n 7, Puerto Real, 11510, Cádiz, Spain aut NATIONALLICENCE 773 0- Plant and Soil Springer International Publishing 393/1-2(2015-08-01), 207-214 0032-079X 393:1-2<207 2015 393 11104