COMPARATIVE CHEMOMETRIC ANALYSIS, RANKING AND SELECTION OF LIPOPHILICITY PARAMETERS OF 6-CHLORO-1,3,5-TRIAZINE DERIVATIVES WITH ACYCLIC AND CYCLIC SUBSTITUENTS

In the present paper, the chemometric analysis, ranking and selection of the most suitable in silico lipophilicity parameters of eight alkyl and cycloalkyl s-triazine derivatives were carried out. The lipophilicity parameters were calculated using various computational approaches and computer programs. The conducted analysis is the basis for further studies aimed to define, compare and examine the influence of alkyl and cycloalkyl substituents, introduced in 6-chloro-1,3,5-triazine-2,4-diamine structure, on molecular lipophilicity and bioactivity. The chemometric methods used in the study are pattern recognition methods, such as hierarchical cluster analysis (HCA) and sum of ranking differences (SRD). The obtained ranking results indicate that the following in silico lipophilicity descriptors can be chosen as the most suitable for interpretation of lipophilicity of the studied series of s-triazine derivatives: AlogP, MlogP, WLOGP, logPKLOP and logPPHYS. The lipophilicity descriptor iLOGP was marked as the least suitable lipophilicity descriptor of the studied series of compounds. The ranking results were validated by 7-fold cross-validation approach and by comparison of ranks by random numbers (CRRN)

New Perspective on Comparative Chemometric and Molecular Modeling of Antifungal Activity and Herbicidal Potential of Alkyl and Cycloalkyl <i>s</i>-Triazine Derivatives

The contamination of the environment by pesticides is becoming a burning issue in many countries in the World. Development, design, and synthesis of new eco-friendly pesticides and modification of existing ones in order to improve their efficacy with the lowest impact on the environment are two main future possibilities in crop protection and the provision of sufficient food for the growing world population. The present study is focused on the comparative analysis of a series of eight symmetrical triazine derivatives, as potential herbicide candidates with acyclic (alkyl) and cyclic (cycloalkyl) substituents, in terms of their antifungal activity towards Aspergillus flavus as an opportunistic fungal pathogenic microorganism responsible for frequent contaminations of crops with aflatoxin, and in terms of their potential application as herbicides in maize, common wheat, barley, and rice crops. The applied methods include the chemometric pattern recognition method (hierarchical cluster analysis), experimental microbiological analysis of antifungal activity (agar well-diffusion method), and molecular docking of the triazines in the corresponding enzymes. The main findings of the conducted study indicate the significant antifungal activity of the studied triazine derivatives towards A. flavus, particularly the compounds with acyclic substituents; five out of eight studied triazines could be applied as systematic herbicides, while the other three triazines could be used as contact herbicides; the compounds with acyclic substituents could be more suitable for application for various crops protection than triazines with cyclic substituents