info:eu-repo/semantics/article
Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives
Fecha
2005-09Registro en:
Fernandez, Luciana Andrea; Santo, Marisa Rosana; Reta, Mario Roberto; Giacomelli, Liliana; Cattana, Rosa Irene; et al.; Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives; Molecular Diversity Preservation International; Molecules; 10; 9; 9-2005; 1197-1208
1420-3049
CONICET Digital
CONICET
Autor
Fernandez, Luciana Andrea
Santo, Marisa Rosana
Reta, Mario Roberto
Giacomelli, Liliana
Cattana, Rosa Irene
Silber, Juana
Risso, Mariela
Cerecetto, Hugo
Gonzalez, Mercedes
Olea-Azar, Claudio
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 N-oxide 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.