Transformation of the plant growth regulator daminozide (Alar) and structurally related compounds with Cu-II ions: Oxidation versus hydrolysis
Library Number:
WA32269
Part Number:
WA32269
Author(s):
Huang C
Source:
ENVIRONMENTAL SCIENCE & TECHNOLOGY
Content Type:
Journal Citations
Year:
2003
Volume:
37(9)
Page(s):
1829-1837
As part of a study of metal ion effects on chemical
transformations of nitrogen-containing agrochemicals, conversion of
daminozide to succinate via cleavage of the hydrazide C-N bond was
examined in the presence and absence of divalent metal ions. No
conversion was observed in metal ion-free solutions or in the presence
of 1.0 mM Ni-II, Zn-II, and Pb-II. Cu-II, in contrast, markedly
increased rates of daminozide to succinate conversion. Halide ions
(Cl-, Br-) had no effect on daminozide conversion in the absence of
metal ions but markedly increased conversion rates observed in the
presence of Cull, The nitrogen-donor ligands ethylenediamine,
N-(2-hydroxyethyl)ethylenediamine, and 1,4,7,10-tetraazacyclododecane
decreased rates of Cu-II-facilitated conversion, while
1,5,9-triazacyclododecane actually increased rates of conversion. H NMR
and UV spectroscopy provide evidence for the formation of 1:1
Cu-II-daminozide complexes. Halide ion effects and nitrogen-donor
ligand effects point to an oxidative mechanism for Cu-II-facilitated
daminozide breakdown, rather than hydrolysis. The structurally related
compound butyric acid 2,2-dimethylhydrazide (BH) is subject to the same
Cu-II-facilitated breakdown via an oxidative mechanism.
N,N-Dimethylsuccinamic acid (SA), in contrast, breaks down via a
hydrolytic mechanism