Abstract
Synthetic herbicides are widely used for weed control in crops. Continuous application of chemicals induces the adaptation of weeds, leading to the development of resistance. Therefore, research for novel synthetic herbicides plays an important role in crop protection and food production. Within this context, it is important to understand the relationship between the structures of a set of compounds endowed with herbicide activity and their biological response. In this work, a quantitative structure-activity relationship (QSAR) study of 34 nostoclide analogues was carried out in order to analyze their ability to inhibit the photosystem-II. Compounds were optimized using the DFT/B3LYP/Def2-TZVPP method. 2D and 3D (Lennard-Jones and electrostatic potential energies) molecular descriptors were calculated at the same theory level. QSAR models showed major importance of electrostatic ligand-acceptor interactions and indicated the presence of aromatic interaction in the benzyl group. A photoelectron transfer via hydrogen-bond was proposed to occur between His215 residue and the carbonyl group.
Highlights
Human growing population and prosperity around the world is driving an increased demand for food
Experimental data of the percentage of inhibition of a set of 34 nostoclide analogues, published by Teixeira et al in 2008, was used to build quantitative structure-activity relationship (QSAR) models based on 2D and 3D molecular descriptors
Its chemical interpretation gave some insight regarding the interactions between the analogues and the plastoquinone QB active site from photosystem II
Summary
Human growing population and prosperity around the world is driving an increased demand for food. Agriculture has developed to achieve higher yields and better-quality products. To yield high crop production, it is important to protect the cultures from pests and diseases.[1,2] Weeds produce the highest potential loss overall among the pests, which can be avoided by applying physical, biological and chemical measures.[2] Crop protection by chemical measures spreads worldwide since the commercialization of the two phenoxyacid herbicides: 2,4-dichlorophenoxyacetic acid (usually called 2,4-D) and the 2-methyl-4-chlorophenoxyacetic acid (MCPA).[2,3] The use of chemicals in crops has become the main method of weed control because of its low cost and high efficiency, encouraging reliance on them.[4] frequent use of chemicals with similar biological mechanism creates a selective pressure on weeds, leading to the development of resistance.[1,4,5] Herbicide resistance was firstly reported in 1970 and confirmed in 495 unique cases until 2017.5,6 Usually, the resistance acquired by a weed species is a result of a mutation in the active site. The development of herbicides with a different mechanism of action is
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