J Mol Model
Grupo de Química Teórica e Estrutural de Anápolis, Universidade Estadual de Goiás, Anápolis, GO, Brazil.
Published: July 2023
Context: The design and synthesis of safe and highly active sulfonylurea herbicides is still a challenge. Therefore, following some principles of structure-activity relationship (SAR) of sulfonylurea herbicides, this work focuses on evaluating two sulfonylurea derivatives bearing electron-withdrawing substituents, namely, -(CO)OCH and -NO on the aryl group, on herbicidal activity. To understand the effects caused by the substituent groups, the molecular and electronic structures of the sulfonylureas were evaluated by density functional theory. Likewise, the crystalline supramolecular arrangements of both compounds were analyzed by Hirshfeld surface, QTAIM, and NBO, with the aim of verifying changes in intermolecular interactions caused by substituent groups. Finally, through a toxicophoric analysis, we were able to predict the interacting groups in their biological target, acetolactate synthase, and verify the interactions with the binding site.
Methods: All theoretical calculations were conducted using the highly parameterized empirical exchange-correlation functional M06-2X accompanied by the diffuse and polarized basis set 6-311++G(d,p). The atomic coordinates were obtained directly from the crystalline structures, and from the energies of the frontier molecular orbitals (HOMO and LUMO), chemical descriptors were obtained that indicated the influence of the functional groups in the sulfonylureas on the reactivity of the molecules. The intermolecular interactions in the crystals were analyzed using the Hirshfeld, QTAIM, and NBO surfaces. Toxicophoric modeling was performed by the PharmaGist webserver and molecular docking calculations were performed by the GOLD 2022.1.0 software package so that the ligand was fitted to the binding site in a 10 Å sphere. For this, genetic algorithm parameters were used using the ChemPLP scoring function for docking and ASP for redocking.
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http://dx.doi.org/10.1007/s00894-023-05629-x | DOI Listing |
Environ Pollut
January 2025
College of Land Resources and Environment, Jiangxi Agricultural University, Nanchang, 330045, P.R. China.
Propyrisulfuron, a novel sulfonylurea herbicide, effectively suppresses intracellular acetolactate synthase activity for weed control, but its adsorption behavior in the soil environment remains unclear. To assess potential agroecosystem risks, the adsorption-desorption behavior and mechanism of propyrisulfuron in six typical agricultural soils of China were investigated using a batch equilibrium method, Density Functional Theory (DFT), Fourier Transform Infrared Spectroscopy (FTIR), and Scanning Electron Microscopy equipped with Energy Dispersive X-ray (SEM-EDX) techniques. It is indicated that the adsorption-desorption of propyrisulfuron in six soils reached equilibrium at 36 hours under the optimum water-to-soil ratio (WSr) of 5:1.
View Article and Find Full Text PDFPest Manag Sci
January 2025
College of Plant Protection, Hunan Agricultural University, Changsha, China.
Background: Resistance to multiple herbicides is common in Lolium rigidum. Here, resistance to acetolactate synthase (ALS)- and susceptibility to acetyl-CoA carboxylase (ACCase)-inhibiting herbicides was confirmed in a glyphosate-resistant L. rigidum population (NLR70) from Australia and the mechanisms of pyroxsulam resistance were examined.
View Article and Find Full Text PDFPlants (Basel)
December 2024
Department of Agroecology and Crop Production, Faculty of Agrobiology, Food and Natural Resources, Czech University of Life Sciences Prague, Kamýcká 129, 165 00 Prague, Czech Republic.
, a prevalent weed in Czech winter wheat fields, has developed resistance to ALS-inhibiting herbicides due to their frequent use. This study reports a biotype of resistant to pyroxsulam, with cross and multiple resistance to iodosulfuron, propoxycarbazone, pinoxaden, and chlortoluron. Dose-response experiments revealed high resistance of both R1 and R2 biotypes to pyroxsulam, with resistance factors (RF) of 6.
View Article and Find Full Text PDFToxics
December 2024
Ufa Institute of Biology of Ufa Federal Research Centre of the Russian Academy of Sciences, 450054 Ufa, Russia.
The ability of some rhizosphere bacteria to mitigate herbicidal stress in cultivated plants may be useful in agriculture and bioremediation. There is poor understanding of how bacteria directly or through herbicide degradation affect the biochemical processes in plants exposed to sulfonylurea herbicides. In this study, treatment with a combination of herbicide metsulfuron-methyl (MSM) and bacteria ( DA1.
View Article and Find Full Text PDFSci Rep
January 2025
Iranian Research Institute of Plant Protection, Agricultural Research, Education and Extension Organization (AREEO), Tehran, Iran.
Winter wild oat (Avena sterilis subsp. ludoviciana (Durieu) Gillet & Magne) has been considered the most common and troublesome weed in wheat fields of Iran. The widespread and continuous use of herbicides has led to the emergence and development of resistant biotypes in A.
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