Degradation studies on benzoxazinoids.: Soil degradation dynamics of 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and its degradation products, phytotoxic allelochemicals from Gramineae

被引:116
作者
Macías, FA
Oliveros-Bastidas, A
Marín, D
Castellano, D
Simonet, AM
Molinillo, JMG
机构
[1] Univ Cadiz, Fac Ciencias, Dept Quim Organ, Grp Alelopatia, E-11510 Puerto Real, Cadiz, Spain
[2] Univ Los Andes, Grp Quim Ecol, Dept Quim, Nucl Univ Pedro Rincon Gutierrez, Merida 5101, Venezuela
关键词
allelopathy; benzoxazinoids; DIMBOA; MBOA; soil degradation; kinetics;
D O I
10.1021/jf0488514
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Benzoxazinoids have been described as important allelochernicals from Gramineae as well as Acanthaceae, Rannunculaceae, and Scrophulariaceae plants. Several bioactivities have been described and evaluated for these compounds, including fungistatic, antifeedant, and phytotoxic. In ongoing studies about allelochernicals as natural herbicide models, the description of soil dynamics in phytotoxic agents has high importance, because the possible biotransformations developed by soil microorganisms could yield compounds with modified biological properties, affecting the overall allelopathic capability of the producer plant in a direct manner. Thus, a complete degradation study has been carried out for 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 6-methoxybenzoxazolin-2(3H)-one (MBOA) in two soils cultivated with Triticum aestivum L. varieties (cv. Astron and cv. Ritmo). The main purpose was to identify degradation products and to elucidate biotransformation dynamics. Results show DIMBOA to degrade rapidly, yielding MBOA in both studied soils at different doses (t(1/2) = 31 +/- 1 h, n = 12) and reaching high conversions (80 +/- 4 h, n = 42). MBOA, an intermediate in the degradation pathway from DIMBOA to 2-amino-7-methoxy-3H-phenoxazin-3-one (AMPO), was more resistant toward biodegradation (t(1/2) = 5 +/- 1 days, n = 6). MBOA showed maximum conversions at a dose of 250 mg/kg of soil (36 +/- 3 days, n = 6). Soil belonging to T aestivum cv. Ritmo crops showed higher degradation capacity than cv. Astron soil. AMPO was the final degradation product observed for DIMBOA in the soils and experimental conditions selected. Consequences for activity and stability of these compounds in relation to allelopathy are discussed.
引用
收藏
页码:6402 / 6413
页数:12
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