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Preparation and Herbicidal Activity of Halogenated 8-Hydroxyquinoline-2-Carboxanilides
1 , 1 , 2 , 1 , 1 , 3 , 4 , 5 , * 1
1  Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
2  Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
3  Global Change Research Centre AS CR, Belidla 986/4a, 603 00 Brno, Czech Republic
4  Department of NMR Spectroscopy and Mass Spectrometry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinskeho 9, 812 37 Bratislava, Slovakia
5  Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia

Abstract: In this study a series of twelve ring-substituted 8-hydroxyquinoline-2-carboxanilides was prepared and characterized. The discussed compounds were synthesized by using microwave-assisted synthesis. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds were found to inhibit PET in photosystem II. Significant PET-inhibiting activity was observed for meta-substituted compounds showing IC50 values close to that of photosystem II herbicide DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea, IC50 = 1.9 μmol/L). N-(3-Fluorophenyl)-8-hydroxyquinoline-2-carboxamide showed the highest PET inhibition. The activity of meta- and para-substituted compounds decreased with lipophilicity increase and electron-withdrawing effect. No influence of any of these parameters on PET-inhibiting activity of ortho-substituted compounds was observed.
Keywords: Hydroxyquinoline-2-carboxanilides; PET inhibition; Spinach chloroplasts; Structure-activity relationships.
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