title: Degradation of RPA 202248 [U-14C-phenyl]alpha(-(cyclopropylcarbonyl)-2-(methylsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile), the primary degradation product of isoxaflutole, in an outdoor aquatic microcosm system.
abstract: Isoxaflutole, the active ingredient in BALANCE WDG and BALANCE PRO corn herbicides and a co-formulant with the herbicide flufenacet in the product EPIC, is readily degraded in soil and water to RPA 202248 alpha(-(cyclopropylcarbonyl)-2-(methyvlsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile). Because RPA 202248 is responsible at the molecular level for isoxaflutole's herbicidal activity it is important to understand the environmental behavior of the degradation product. Laboratory studies suggest that RPA 202248 is stable to hydrolysis and photolysis in aqueous systems and hence poses a possible environmental concern. As part of a program of work towards understanding the actual field situation, an outdoor microcosm study was carried out. Over the course of the 29-day study, residues remained predominantly in the aqueous phase. A slow but steady degradation of RPA 202248 was observed leading to the formation of RPA 203328 (2-methylsulfonyl-4-trifluoromethylbenzoic acid), which has no herbicidal activity. The half-life of RPA 202248 was calculated to be 103 days. These findings indicate that aqueous degradation should be considered as a potential route of dissipation when assessing the fate of RPA 202248 in large scale impounded water bodies, such as ponds, lakes, or reservoirs in the Mid-West Corn Belt.
authors.affiliation: Bayer CropScience, 17745 South Metcalf, Stilwell, KS 66085, USA. kent.rupprecht@bayercropscience
authors.forename: J Kent
authors.initials: JK
authors.lastname: Rupprecht
authors.forename: Anne
authors.initials: A
authors.lastname: Liu
authors.forename: Iain
authors.initials: I
authors.lastname: Kelly
authors.forename: Richard
authors.initials: R
authors.lastname: Allen
mesh_terms: D002250:Carbon Radioisotopes / Q000032:analysis; D003521:Cyclopropanes / Q000032:analysis*; D004784:Environmental Monitoring; D006207:Half-Life; D006868:Hydrolysis; D007555:Isoxazoles / Q000378:metabolism*; D009570:Nitriles / Q000032:analysis*; D010782:Photolysis; D014874:Water Pollutants, Chemical / Q000032:analysis*
chemical_list: D002250:Carbon Radioisotopes; D003521:Cyclopropanes; D007555:Isoxazoles; D009570:Nitriles; D014874:Water Pollutants, Chemical; C495685:alpha(-(cyclopropylcarbonyl)-2-(methyvlsulfonyl)-beta-oxo-4-(trifluromethyl)benzenepropanenitrile); C415327:isoxaflutole