Artículo de revista
Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
Fecha
2005-09Registro en:
MOLECULES, V.: 10, issue: 9, p. 1197-1208, SEP 2005
1420-3049
Autor
Fernández, Luciana A.
Santo, Marisa R.
Reta, Mario
Giacomelli, Liliana
Cattana, Rosa
Silber, Juana J.
Risso, Mariela
Cerecetto, Hugo
González, Mercedes
Olea Azar, Claudio
Institución
Resumen
The relationship between the herbicidal activity of a number of novel 1,2,5-
oxadiazole N-oxides and some physicochemical properties potentially related with this
bioactivity, such as polarity, molecular volume, proton acceptor ability, lipophilicity, and
reduction potential were studied. The semiempirical molecular orbital method AM1 was
used to calculate theoretical descriptors such as dipolar moment, molecular volume,
Mulliken´s charge and the octanol/water partition coefficients (log Po/w). The values of
the reduction potentials (Er) were obtained by cyclic voltammetry. In addition, the
retention factors (log k’w) on a reversed-phase high-performance liquid chromatography
(RP-HPLC) column in pure aqueous mobile phases were measured for several N-oxide
derivatives. The log k’w values show good correlation with the calculated values of log
Po/w, showing that the chromatographic parameter can be used as lipophilicity descriptor
for these compounds. The multiple regression analysis between the descriptors for the Noxide
derivatives and the herbicide activity indicate that the variance in the biological
activity can be explained by changes in the lipophilicity and in the reduction potential.