Structure-Activity Relationships (SAR) Studies of Benzoxazinones, Their Degradation Products and Analogues. Phytotoxicity on Standard Target Species (STS)
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- 作者：Francisco A. Mací ; as ; David Marí ; n ; Alberto Oliveros-Bastidas ; Diego Castellano ; Ana M. Simonet ; and José ; M. G. Molinillo
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2005
- 出版时间：February 9, 2005
- 年：2005
- 卷：53
- 期：3
- 页码：538 - 548
- 全文大小：583K
- 年卷期：v.53,no.3(February 9, 2005)
- ISSN：1520-5118
文摘
Benzoxazinones 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) and 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) have been considered key compounds for understanding allelopathic phenomena in Gramineae crop plants such as corn (Zea mays L.), wheat (Triticumaestivum L.), and rye (Secale cereale L.). The degradation processes in the environment observedfor these compounds, in which soil microbes are directly involved, could affect potential allelopathicactivity of these plants. We present in this work a complete structure-activity relationships studybased on the phytotoxic effects observed for DIMBOA, DIBOA, and their main degradation products,in addition to several synthetic analogues of them. Their effects were evaluated on standard targetspecies (STS), which include Triticum aestivum L. (wheat) and Allium cepa L. (onion) as monocotsand Lepidium sativum L. (cress), Lactuca sativa L. (lettuce), and Lycopersicon esculentum Will.(tomato) as dicots. This permitted us to elucidate their ecological role and to propose new herbicidemodels based on their structures. The best phytotoxicity results were shown by the degradationchemical 2-aminophenoxazin-3-one (APO) and several 2-deoxy derivatives of natural benzoxazinones,including 4-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one (ABOA), 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA), and 4-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIMBOA). They showedhigh inhibitory activity over almost all species growth. The fact that APO is a degradation productfrom DIBOA with high phytotoxicity and stability makes it possible to assign an important ecologicalrole regarding plant defense mechanisms. 2-Deoxy derivatives of natural benzoxazinones display awide range of activities that allow proposing them as new leads for natural herbicide models with a1,4-benzoxazine skeleton.Keywords: Allelochemicals, DIMBOA, DIBOA, soil degradation products, wheat, phytotoxicity, SAR,STS.