Structure-Activity Relationship Studies of Benzoxazinones and Related Compounds. Phytotoxicity on Echinochloa crus-galli (L.) P. Beauv.
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- 作者：Francisco A. Mací ; as ; Nuria Chinchilla ; Rosa M. Varela ; Alberto Oliveros-Bastidas ; David Marí ; n ; and José ; M. G. Molinillo
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2005
- 出版时间：June 1, 2005
- 年：2005
- 卷：53
- 期：11
- 页码：4373 - 4380
- 全文大小：284K
- 年卷期：v.53,no.11(June 1, 2005)
- ISSN：1520-5118
文摘
Echinochloa crus-galli (E. crus-galli; barnyardgrass) is a weed widely distributed. It constitutes a seriousweed problem in 42 countries and has been found in at least 27 more. It is the world's main weed ofrice affecting up to 36 crops worldwide. Several biotypes of this plant, with resistance to herbicideswith different modes of action have evolved. In our ongoing studies regarding the potential applicationof benzoxazinones and their soil degradation products for weed control, a complete structure-activityrelationships (SARs) study was made by using barnyardgrass as the target plant. Compounds usedin this study were previously tested on a wide variety of standard target species (STS), and theyinclude natural allelochemicals 2-O-
-D-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one(DIBOA-Glc), 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), together with some degradation derivatives found in wheatcrop soil and some synthetic analogues. Their phytotoxicity on E. crus-galli is discussed and comparedwith the results obtained from previous screening. This work constitutes the next step in the searchfor natural herbicide models based on benzoxazinones and their degradation products. The mostactive compounds were the degradation product 2-aminophenol (APH) and the synthetic analogue4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA). Their activities confirm the direction proposedin our previous SAR study, which establishes D-DIBOA to be the best lead for natural herbicidemodel development with benzoxazinone structure.Keywords: Rice; Echinochloa crus-galli; barnyardgrass; benzoxazinones; DIMBOA; DIBOA; 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one; bioassay; phytotoxicity
-D-glucopyranosyl-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one(DIBOA-Glc), 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), together with some degradation derivatives found in wheatcrop soil and some synthetic analogues. Their phytotoxicity on E. crus-galli is discussed and comparedwith the results obtained from previous screening. This work constitutes the next step in the searchfor natural herbicide models based on benzoxazinones and their degradation products. The mostactive compounds were the degradation product 2-aminophenol (APH) and the synthetic analogue4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one (D-DIBOA). Their activities confirm the direction proposedin our previous SAR study, which establishes D-DIBOA to be the best lead for natural herbicidemodel development with benzoxazinone structure.Keywords: Rice; Echinochloa crus-galli; barnyardgrass; benzoxazinones; DIMBOA; DIBOA; 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one; bioassay; phytotoxicity