title: Nature of impurities in fertilizers containing EDDHMA/Fe(3+), EDDHSA/Fe(3+), and EDDCHA/Fe(3+) chelates.
abstract: Iron chelates derived from ethylenediaminedi(o-hydroxyphenylacetic) acid (EDDHA), ethylenediaminedi(o-hydroxy-p-methylphenylacetic) acid (EDDHMA), ethylenediaminedi(2-hydroxy-5-sulfophenylacetic) acid (EDDHSA), and ethylenediaminedi(5-carboxy-2-hydroxyphenylacetic) acid (EDDCHA) are remarkably efficient in correcting iron chlorosis in plants growing in alkaline soils. This work reports the determination of impurities in commercial samples of fertilizers containing EDDHMA/Fe(3+), EDDHSA/Fe(3+), and EDDCHA/Fe(3+). The active components (EDDHMA/Fe(3+), EDDHSA/Fe(3+), and EDDCHA/Fe(3+)) were separated easily from other compounds present in the fertilizers by HPLC. Comparison of the retention times and the UV-visible spectra of the peaks obtained from commercial EDDHSA/Fe(3+) and EDDCHA/Fe(3+) samples with those of standard solutions showed that unreacted starting materials (p-hydroxybenzenesulfonic acid and p-hydroxybenzoic acid, respectively) were always present in the commercial products. 1D and 2D NMR experiments showed that commercial fertilizers based on EDDHMA/Fe(3+) contained impurities having structures tentatively assigned to iron chelates of two isomers of EDDHMA. These findings suggest that current production processes of iron chelates used in agriculture need to be improved.
authors.affiliation: Department of Agricultural Chemistry, Faculty of Sciences, Autonoma University of Madrid, 28049 Madrid, Spain.
authors.forename: Ana
authors.initials: A
authors.lastname: Alvarez-Fernández
authors.forename: Mauro A
authors.initials: MA
authors.lastname: Cremonini
authors.forename: Miguel A
authors.initials: MA
authors.lastname: Sierra
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Placucci
authors.forename: Juan J
authors.initials: JJ
authors.lastname: Lucena
mesh_terms: D002851:Chromatography, High Pressure Liquid; D005029:Ethylenediamines; D005308:Fertilizers / Q000032:analysis*; D007502:Iron Chelating Agents / Q000032:analysis*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy
chemical_list: D005029:Ethylenediamines; D005308:Fertilizers; D007502:Iron Chelating Agents; C443343:ethylenediaminedi-(o-hydroxy-p-methylphenylacetic)acid; C011813:ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid)