Structure and Fertilizer Properties of Byproducts Formed in the Synthesis of EDDHA

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 determin...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2006-06, Vol.54 (12), p.4355-4363
Main Authors: Hernández-Apaolaza, Lourdes, García-Marco, Sonia, Nadal, Paloma, Lucena, Juan J, Sierra, Miguel A, Gómez-Gallego, Mar, Ramírez-López, Pedro, Escudero, Rosa
Format: Article
Language:English
Subjects:
Agrochemicals
Biological and medical sciences
byproducts
chelating agents
chelation
cucumbers
Cucumis sativus
Cucumis sativus - metabolism
Drug Stability
Ethylenediamines - chemical synthesis
Ethylenediamines - chemistry
Fertilizers
Food industries
Fundamental and applied biological sciences. Psychology
Glycine max
Glycine max - metabolism
iron
Iron - chemistry
Iron - metabolism
Isomerism
isomers
Magnetic Resonance Spectroscopy
Molecular Structure
nutrient availability
nutrient uptake
o,p-EDDHA
p,p-EDDHA
Plants - metabolism
Soil - analysis
Solutions
soybeans
Spectrometry, Mass, Electrospray Ionization
synthesis
waste utilization
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Summary: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+. Keywords: Iron chelates; fertilizers; o,o-EDDHA; o,p-EDDHA
ISSN:0021-8561
1520-5118
DOI:10.1021/jf0605749