title: Comparative degradation of [14C]-2,4-dichlorophenoxyacetic acid in wheat and potato after Foliar application and in wheat, radish, lettuce, and apple after soil application.
abstract: The fate of 2,4-dichlorophenoxyacetic acid (2,4-D) applied foliarly as the 2-ethylhexyl ester (EHE) to wheat and potatoes, to the soil as the dimethylamine (DMA) salt under apple tree canopies, and preplant as the free acid for wheat, lettuce, and radish was studied to evaluate metabolic pathways. Crop fractions analyzed for (14)C residues included wheat forage, straw, and grain; potato vine and tubers; and apple fruit. The primary metabolic pathway for foliar application in wheat is ester hydrolysis followed by the formation of base-labile 2,4-D conjugates. A less significant pathway for 2,4-D in wheat was ring hydroxylation to give NIH-shift products 2,5-dichloro-4-hydroxyphenoxyacetic acid (4-OH-2,5-D), 4-OH-2,3-D, and 5-OH-2,4-D both free and as acid-labile conjugates. The primary metabolic pathway in potato was again ester hydrolysis. 2,4-D acid was further transformed to 4-chlorophenoxyacetic acid and 4-OH-2,5-D. For the soil applications, (14)C residues in the crops were low, and characterization of the (14)C residues indicated association with or incorporation into the biochemical matrix of the tissue. The degradative pathways observed in wheat are similar to those characterized in other intact plant studies but differ from those in studies in wheat cell suspension culture in that no amino acid conjugates were observed.
authors.affiliation: ABC Laboratories, Inc., 7200 East ABC Lane, Columbia, Missouri 65205, USA. awhamburg@dowagro.com
authors.forename: A
authors.initials: A
authors.lastname: Hamburg
authors.forename: V
authors.initials: V
authors.lastname: Puvanesarajah
authors.forename: T J
authors.initials: TJ
authors.lastname: Burnett
authors.forename: D E
authors.initials: DE
authors.lastname: Barnekow
authors.forename: N D
authors.initials: ND
authors.lastname: Premkumar
authors.forename: G A
authors.initials: GA
authors.lastname: Smith
mesh_terms: D015084:2,4-Dichlorophenoxyacetic Acid / Q000008:administration & dosage* / Q000378:metabolism*; D001673:Biodegradation, Environmental; D002250:Carbon Radioisotopes; D005638:Fruit / Q000378:metabolism*; D006540:Herbicides / Q000378:metabolism*; D018515:Plant Leaves; D012987:Soil; D011198:Solanum tuberosum / Q000378:metabolism; D014908:Triticum / Q000378:metabolism*; D014675:Vegetables / Q000378:metabolism*
chemical_list: D002250:Carbon Radioisotopes; D006540:Herbicides; D012987:Soil; D015084:2,4-Dichlorophenoxyacetic Acid