title: Role of hydroxylamine intermediates in the phytotransformation of 2,4,6-trinitrotoluene by Myriophyllum aquaticum.
abstract: Phytotransformation studies of 2,4,6-trinitrotoluene (TNT) were conducted using Myriophyllum aquaticum to clarify the role of initial intermediates of TNT transformation in the complex product distributions reported previously. 2-Hydroxylamino-4,6-dinitrotoluene (2HA46DNT) and 4-hydroxylamino-2,6-dinitrotoluene (4HA26DNT) were the initial intermediates of TNT phytotransformation. 2HA46DNT and 4HA26DNT were both abiotically transformed to 4,4',6,6'-tetranitro-2,2'-azoxytoluene (2,2'azoxy) and 2,2',6,6'-tetranitro-4,4'-azoxytoluene (4,4'azoxy) and also phytoreduced to the related amines 2-amino-4,6-dinitrotoluene (2A46DNT) and 4-amino-2,6-dinitrotoluene (4A26DNT). To further elucidate the initial steps of this TNT phytotransformation pathway, the transformations of known intermediates (including 2HA46DNT, 4HA26DNT, 2A46DNT, 4A26DNT, 2,2'azoxy, and 4,4'azoxy) were monitored in plant systems. The transformation rates were measured, and kinetic analysis using pseudo-first-order models was used to evaluate the relative rates of competing reactions. The formation of the azoxy products was determined to be more rapid than the formation of the amine products. Both the azoxy and amine products were subject to uptake and further transformation by the plant.
authors.affiliation: Department of Civil and Environmental Engineering, MS-317, Rice University, Houston, Texas 77005-1892, USA.
authors.forename: Chuanyue
authors.initials: C
authors.lastname: Wang
authors.forename: Delina Y
authors.initials: DY
authors.lastname: Lyon
authors.forename: Joseph B
authors.initials: JB
authors.lastname: Hughes
authors.forename: George N
authors.initials: GN
authors.lastname: Bennett
mesh_terms: D001673:Biodegradation, Environmental; D001711:Biotransformation; D004787:Environmental Pollution / Q000517:prevention & control; D019811:Hydroxylamine / Q000737:chemistry*; D007700:Kinetics; D019684:Magnoliopsida / Q000502:physiology*; D014303:Trinitrotoluene / Q000378:metabolism*; D014874:Water Pollutants, Chemical / Q000378:metabolism*
chemical_list: D014874:Water Pollutants, Chemical; D014303:Trinitrotoluene; D019811:Hydroxylamine