Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts
Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts
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DOI：
10.1021/jf051147i
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发表时间：
2006-02-22
影响因子：
6.1
通讯作者：
Fomsgaard, IS
中科院分区：
文献类型：
--
作者：
Krogh, SS;Mensz, SJM;Fomsgaard, IS
种植谷物（特别是黑麦）是轮作作物的一种常见做法，它们被纳入土壤以增加土壤肥力或有机质含量。这种掺入的额外消毒效果经常得到重视，据说是由于苯并恶唑啉酮的浸出和随后形成的苯并恶唑啉酮。在本研究中，小麦（Stakado）和黑麦（Hacada）芽按模拟农业实践的量掺入土壤。通过提取和LC-MS分析，考察了土壤中苯并恶嗪酮类、苯并恶唑啉酮类和苯并恶唑酮类化合物的消失和出现情况。在小麦试验中检测到6-甲氧基苯并恶唑啉-2- 1 （MBOA）为主要化合物。同时检测到2-羟基-7-甲氧基-1,4-苯并恶嗪-3-one （HMBOA）和2-羟基-1,4-苯并恶嗪-3-one （HBOA）。未检出苯恶嗪类药物。黑麦实验的情况更为复杂。培养前2 d检测到MBOA和2,4-二羟基-1,4-苯并恶唑啉-2- 1 （DIBOA）为主要化感物质，依次为HBOA、HMBOA和苯并恶唑啉-2- 1 （BOA）。孵育后期检测到2-氨基- 3h -苯恶嗪-3- 1 (APO)， HBOA的数量出现了明显的上升，但又出现了下降。土壤中苯并恶嗪酮代谢物及其衍生物的分布具有动态和时间依赖性。大多数化合物的最高浓度出现在掺入后第1天。少数化合物在第4天达到最大浓度。本研究首次揭示了小麦和黑麦芽掺入土壤后生物活性苯并恶嗪酮衍生物的动态变化规律。开发了有机合成HBOA和HMBOA的方法作为研究的一部分。
Growing cereals (especially rye), which are incorporated into the soil to increase soil fertility or organic matter content, is a common practice in crop rotation. The additional sanitizing effect of this incorporation has often been appreciated and is said to be due to leaching of benzoxazinones and subsequent formation of benzoxazolinones. In this study wheat (Stakado) and rye (Hacada) sprouts were incorporated into soil in amounts that simulated agricultural practice. By extraction and subsequent 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 phenoxazinones were detected. For the rye experiment the picture was more complex. In the first 2 days of incubation MBOA and 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA) were detected as the main allelochemicals along with HBOA, HMBOA, and benzoxazolin-2-one (BOA), in decreasing order. Later in the incubation period some 2-amino-3H-phenoxazin-3-one (APO) was detected and the amount of HBOA increased considerably and decreased again. The profiling of the benzoxazinone metabolites and their derivates in soil was dynamic and time-dependent. The highest concentrations of most of the compounds were seen at day 1 after incorporation. A maximum concentration was reached at day 4 for a few of the compounds. This study is the first of its kind that shows the dynamic pattern of biologically active benzoxazinone derivates in soil after incorporation of wheat and rye sprouts. Methods for organic synthesis of HBOA and HMBOA were developed as part of the study.