Molecular Diversity

, Volume 15, Issue 4, pp 901–909

QSAR model toward the rational design of new agrochemical fungicides with a defined resistance risk using substructural descriptors

  • Alejandro Speck-Planche
  • Valeria V. Kleandrova
  • Julio A. Rojas-Vargas
Full-Length Paper

DOI: 10.1007/s11030-011-9320-7

Cite this article as:
Speck-Planche, A., Kleandrova, V.V. & Rojas-Vargas, J.A. Mol Divers (2011) 15: 901. doi:10.1007/s11030-011-9320-7

Abstract

The increasing resistance of several phytopathogenic fungal species to the existing agrochemical fungicides has alarmed to the worldwide scientific community. There is no available methodology to predict in an efficient way if a new fungicide will have resistance risk due to fungal species which cause considerable crop losses. In an attempt to overcome this problem, a multi-resistance risk QSAR model, based on substructural descriptors was developed from a heterogeneous database of compounds. The purpose of this model is the classification, design, and prediction of agrochemical fungicides according to resistance risk categories. The QSAR model classified correctly 85.11% of the fungicides and the 85.07% of the inactive compounds in the training series, for an accuracy of 85.08%. In the prediction series, the percentages of correct classification were 85.71 and 86.55% for fungicides and inactive compounds, respectively, with an accuracy of 86.39%. Some fragments were extracted and their quantitative contributions to the fungicidal activity were calculated taking into consideration the different resistance risk categories for agrochemical fungicides. In the same way, some fragments present in molecules with fungicidal activity and with negative contributions were analyzed like structural alerts responsible of resistance risk.

Keywords

Agrochemical fungicidesResistance riskMolecular descriptorsFragmentsLinear discriminant analysis

Supplementary material

11030_2011_9320_MOESM1_ESM.doc (570 kb)
ESM 1 (DOC 570 kb)
11030_2011_9320_MOESM2_ESM.doc (872 kb)
ESM 2 (DOC 872 kb)

Copyright information

© Springer Science+Business Media B.V. 2011

Authors and Affiliations

  • Alejandro Speck-Planche
    • 1
  • Valeria V. Kleandrova
    • 2
  • Julio A. Rojas-Vargas
    • 1
  1. 1.Faculty of Natural Sciences, Department of ChemistryUniversity of OrienteSantiago de CubaCuba
  2. 2.Faculty of Technology and Production ManagementMoscow State University of Food ProductionMoscowRussia