Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives

Molecules

Luciana A. Fernandez²  Marisa R. Santo²  Mario Reta²  Liliana Giacomelli²  Rosa Cattana²  Juana J. Silber²  Mariela Risso¹  Hugo Cerecetto¹  Mercedes Gonzalez¹ 

[1] Departamento de Química Orgánica. Facultad de Química – Facultad de Ciencias. Universidad de la República. CC 1157. 11800. Montevideo, Uruguay.;Departamento de Química. Universidad Nacional de Río Cuarto. Agencia Postal Nro 3. 5800. Río Cuarto, Argentina.

关键词: 1;    2;    5-Oxadiazole N-oxide derivatives;    herbicides;    lipophilicity;   

DOI  :  10.3390/10091197

来源: mdpi

【 摘 要 】

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 P_o/w). The values of the reduction potentials (E_r) 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 P_o/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.

【 授权许可】

Unknown   
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