Synthesis and Evaluation of New Phytotoxic Fluorinated Chalcones as Photosystem II and Seedling Growth Inhibitors.

Autor: de Pádua GMS; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., Pitteri TS; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., Ferreira Basso MA; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., de Vasconcelos LG; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., Ali A; Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan., Dall'Oglio EL; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., Sampaio OM; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil., Curcino Vieira LC; Department of Chemistry, Federal University of Mato Grosso, Cuiabá-MT, 78060-900, Brazil.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Apr; Vol. 21 (4), pp. e202301564. Date of Electronic Publication: 2024 Mar 07.
DOI: 10.1002/cbdv.202301564
Abstrakt: The development of novel phytotoxic compounds has been an important aim of weed control research. In this study, we synthesized fluorinated chalcone derivatives featuring both electron-donating and electron-withdrawing groups. These compounds were evaluated both as inhibitors of the photosystem II (PSII) electron chain as well as inhibitors of the germination and seedling growth of Amaranthus plants. Chlorophyll a (Chl a) fluorescence assay was employed to evaluate their effects on PSII, while germination experiments were conducted to assess their impact on germination and seedling development. The results revealed promising herbicidal activity for (E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (7 a) and (E)-1-(4-fluorophenyl)-3-phenylprop-2-en-1-one (7 e). Compounds 7 a and 7 e exhibited a reduction in Chl a parameters associated with performance indexes and electron transport per reaction center. This reduction suggests a decrease in PSII activity, attributed to the blockage of electron flow at the quinone pool. Molecular docking analyses of chalcone derivatives with the D1 protein of PSII revealed a stable binding conformation, wherein the carbonyl and fluorine groups interacted with Phe265 and His215 residues, respectively. Additionally, at a concentration of 100 μM, compound 7 e demonstrated pre- and post-emergent herbicidal activity, resulting in a reduction of the seed germination index, radicle and hypocotyl lengths of Amaranthus weeds.
(© 2024 Wiley‐VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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