Fate of Benzoxazinone Allelochemicals in Soil after Incorporation of Wheat and Rye Sprouts

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• 作者：Stine S. Krogh ; Susanne J. M. Mensz ; Susan T. Nielsen ; Anne G. Mortensen ; Carsten Christophersen ; and Inge S. Fomsgaard
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2006
• 出版时间：February 22, 2006
• 年：2006
• 卷：54
• 期：4
• 页码：1064 - 1074
• 全文大小：405K
• 年卷期：v.54,no.4(February 22, 2006)
• ISSN：1520-5118

文摘

Growing cereals (especially rye), which are incorporated into the soil to increase soil fertility or organicmatter content, is a common practice in crop rotation. The additional sanitizing effect of thisincorporation has often been appreciated and is said to be due to leaching of benzoxazinones andsubsequent formation of benzoxazolinones. In this study wheat (Stakado) and rye (Hacada) sproutswere incorporated into soil in amounts that simulated agricultural practice. By extraction andsubsequent LC-MS analysis the disappearance and appearance of benzoxazinones, benzoxazolinones, and phenoxazinones in soil were followed. In the wheat experiments 6-methoxybenzoxazolin-2-one (MBOA) was detected as the main compound. 2-Hydroxy-7-methoxy-1,4-benzoxazin-3-one(HMBOA) and 2-hydroxy-1,4-benzoxazin-3-one (HBOA) were detected as well. No phenoxazinoneswere detected. For the rye experiment the picture was more complex. In the first 2 days of incubationMBOA and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected as the main allelochemicalsalong with HBOA, HMBOA, and benzoxazolin-2-one (BOA), in decreasing order. Later in the incubationperiod some 2-amino-3H-phenoxazin-3-one (APO) was detected and the amount of HBOA increasedconsiderably and decreased again. The profiling of the benzoxazinone metabolites and their derivatesin soil was dynamic and time-dependent. The highest concentrations of most of the compounds wereseen at day 1 after incorporation. A maximum concentration was reached at day 4 for a few of thecompounds. This study is the first of its kind that shows the dynamic pattern of biologically activebenzoxazinone derivates in soil after incorporation of wheat and rye sprouts. Methods for organicsynthesis of HBOA and HMBOA were developed as part of the study.Keywords: Rye; wheat; allelopathy; allelochemicals; hydroxamic acids; DIBOA; DIMBOA; HBOA;HMBOA