Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives 英文参考文献.docVIP

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Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives 英文参考文献.doc

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Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives 英文参考文献

Molecules 2005, 10, 1197-1208 molecules ISSN 1420-3049 Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives Luciana A. Fernandez 1, Marisa R. Santo 1, Mario Reta 1, Liliana Giacomelli 1, Rosa Cattana 1, Juana J. Silber 1,*, Mariela Risso 2, Hugo Cerecetto 2, Mercedes Gonzalez 2 and Claudio Olea- Azar 3 1 Departamento de Química. Universidad Nacional de Río Cuarto. Agencia Postal Nro 3. 5800. Río Cuarto, Argentina. 2 Departamento de Química Orgánica. Facultad de Química – Facultad de Ciencias. Universidad de la República. CC 1157. 11800. Montevideo, Uruguay. 3 Departamento de Química Inorgánica y Analítica. Facultad de Ciencias Químicas y Farmacéuticas. Universidad de Chile, Chile. * Author to whom correspondence should be addressed; E-mail jsilber@.ar Received: 2 December 2004; in revised form 8 July 2005 / Accepted: 9 July 2005 / Published: 30 September 2005 Abstract: 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 t