Structure and fertilizer properties of byproducts formed in the synthesis of EDDHA

J Agric Food Chem. 2006 Jun 14;54(12):4355-63. doi: 10.1021/jf0605749.

Abstract

The synthesis of commercial EDDHA produces o,o-EDDHA as the main reaction product, together with a mixture of regioisomers (o,p-EDDHA and p,p-EDDHA) and other unknown byproducts also able to complex Fe3+. These compounds have been obtained by direct synthesis, and their structures have been determined by ESI-MS analysis as oligomeric EDDHA-like products, formed by polysubstitution in the phenolic rings. Short-term experiments show that the iron complexes of samples enriched in these oligomeric byproducts have adequate stability in solution, but a significant amount of them is lost after interaction with soils and soil materials. Mildly chlorotic cucumber plants are able to reduce iron better from o,p-EDDHA/Fe3+ than from the iron complexes of the oligomeric byproducts. In hydroponics, the chlorotic soybean susceptible plants have a lower potential for Fe absorption from these byproducts than from o,o-EDDHA/Fe3+ and from o,p-EDDHA/Fe3+. In the studied conditions, the iron chelates of EDDHA byproducts do not have the long-lasting effect shown by o,o-EDDHA/Fe3+ and present a less efficient fast-action effect than the o,p-EDDHA/Fe3+.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agrochemicals
  • Cucumis sativus / metabolism
  • Drug Stability
  • Ethylenediamines / chemical synthesis*
  • Ethylenediamines / chemistry*
  • Fertilizers*
  • Glycine max / metabolism
  • Iron / chemistry
  • Iron / metabolism
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants / metabolism
  • Soil / analysis
  • Solutions
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Agrochemicals
  • Ethylenediamines
  • Fertilizers
  • Soil
  • Solutions
  • ethylenediamine-N,N'-bis(2-hydroxyphenylacetic acid)
  • Iron