Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D3]-MBOA in soil.
To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as a powerful tool. MBOA is formed in soil when the cereal allelochemical 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) is exuded from plant material to soil. Degradation experiments were performed in concentrations of 400 microg of benzoxazolinone/g of soil for MBOA and its isotopomer 6-trideuteriomethoxybenzoxazolin-2-one ([D3]-MBOA). Previously identified metabolites 2-amino-7-methoxyphenoxazin-3-one (AMPO) and 2-acetylamino-7-methoxyphenoxazin-3-one (AAMPO) were detected. Furthermore, several novel compounds were detected and provisionally characterized. The environmental impact of these compounds and their long-range effects are yet to be discovered. This is imperative due to the enhanced interest in exploiting the allelopathic properties of cereals as a means of reducing the use of synthetic pesticides.
Chemical Institute, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.
Thomas
T
Etzerodt
Susan T
ST
Nielsen
Anne G
AG
Mortensen
Carsten
C
Christophersen
Inge S
IS
Fomsgaard
D001583:Benzoxazoles / Q000032:analysis / Q000378:metabolism*; D003903:Deuterium; D002523:Edible Grain / Q000737:chemistry*; D010575:Pesticides; D010675:Pheromones / Q000378:metabolism*; D012987:Soil / Q000032:analysis*
D001583:Benzoxazoles; D010575:Pesticides; D010675:Pheromones; D012987:Soil; C031896:6-methoxybenzoxazolinone; D003903:Deuterium