Structure-Activity Relationship (SAR) Studies of Benzoxazinones, Their Degradation Products, and Analogues. Phytotoxicity on Problematic Weeds Avena fatua L. and Lolium rigidum Gaud.
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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：2006
- 出版时间：February 22, 2006
- 年：2006
- 卷：54
- 期：4
- 页码：1040 - 1048
- 全文大小：354K
- 年卷期：v.54,no.4(February 22, 2006)
- ISSN：1520-5118
文摘
Avena fatua L. (wild oat) and Lolium rigidum Gaud. (rigid ryegrass) are highly problematic weedsaffecting a wide variety of cereal crops worldwide. The fact that both of these weeds have developedresistance to several herbicide groups made them optimal candidates as target organisms for ongoingresearch about the potential application of allelochemicals and analogue compounds as naturalherbicide models. Benzoxazinones, a family of natural allelochemicals present in corn, wheat, andrye, including 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one and 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one, together with some degradation products, found in crop soils as well as inother systems, and some synthetic analogues of them were tested on wild oat and rigid ryegrassseeds; the results were statistically treated, and some structure-activity relationships, useful in furtherdevelopment of natural herbicide models, were elucidated. The most active compounds were thesynthetic benzoxazinone 2-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one and the degradation product2-aminophenoxazin-3-one, with highly significant inhibition on the development of both weeds. Theecological role of these compounds is discussed by considering both degradability and phytotoxicity.The bioactivity of aminophenoxazines has been correlated by their aqueous solubility-lipophilicitypredicted by means of computational methods.Keywords: Allelopathy; SAR; benzoxazinones; aminophenoxazines; DIBOA; DIMBOA; wild oat; rigidryegrass; bioassay; phytotoxicity