4-Hydroxybenzoic Acid-Based Hydrazide–Hydrazones as Potent Growth Inhibition Agents of Laccase-Producing Phytopathogenic Fungi That Are Useful in the Protection of Oilseed Crops
Halina Maniak,
Konrad Matyja,
Elżbieta Pląskowska,
Joanna Jarosz,
Paulina Majewska,
Joanna Wietrzyk,
Hanna Gołębiowska,
Anna Trusek,
Mirosław Giurg
Affiliations
Halina Maniak
Department of Micro, Nano, and Bioprocess Engineering, Faculty of Chemistry, Wroclaw University of Science and Technology, 4/6 Norwida Street, 50-373 Wroclaw, Poland
Konrad Matyja
Department of Micro, Nano, and Bioprocess Engineering, Faculty of Chemistry, Wroclaw University of Science and Technology, 4/6 Norwida Street, 50-373 Wroclaw, Poland
Elżbieta Pląskowska
Division of Plant Pathology and Mycology, Department of Plant Protection, Wroclaw University of Environmental and Life Sciences, 24A Grunwald Square, 50-363 Wroclaw, Poland
Joanna Jarosz
Laboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigla Street, 53-114 Wroclaw, Poland
Paulina Majewska
Institute of Technology and Life Sciences-National Research Institute, 3 Hrabska Avenue, 05-090 Raszyn, Poland
Joanna Wietrzyk
Laboratory of Experimental Anticancer Therapy, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigla Street, 53-114 Wroclaw, Poland
Hanna Gołębiowska
Department of Weed Science and Tillage Systems, Institute of Soil Science and Plant Cultivation State Research Institute, 61 Orzechowa Street, 50-540 Wroclaw, Poland
Anna Trusek
Department of Micro, Nano, and Bioprocess Engineering, Faculty of Chemistry, Wroclaw University of Science and Technology, 4/6 Norwida Street, 50-373 Wroclaw, Poland
Mirosław Giurg
Department of Organic and Medicinal Chemistry, Faculty of Chemistry, Wroclaw University of Science and Technology, 27 Wybrzeże Wyspiańskiego, 50-370 Wroclaw, Poland
The research on new compounds against plant pathogens is still socially and economically important. It results from the increasing resistance of pests to plant protection products and the need to maintain high yields of crops, particularly oilseed crops used to manufacture edible and industrial oils and biofuels. We tested thirty-five semi-synthetic hydrazide–hydrazones with aromatic fragments of natural origin against phytopathogenic laccase-producing fungi such as Botrytis cinerea, Sclerotinia sclerotiorum, and Cerrena unicolor. Among the investigated molecules previously identified as potent laccase inhibitors were also strong antifungal agents against the fungal species tested. The highest antifungal activity showed derivatives of 4-hydroxybenzoic acid and salicylic aldehydes with 3-tert-butyl, phenyl, or isopropyl substituents. S. sclerotiorum appeared to be the most susceptible to the tested compounds, with the lowest IC50 values between 0.5 and 1.8 µg/mL. We applied two variants of phytotoxicity tests for representative crop seeds and selected hydrazide–hydrazones. Most tested molecules show no or low phytotoxic effect for flax and sunflower seeds. Moreover, a positive impact on seed germination infected with fungi was observed. With the potential for application, the cytotoxicity of the hydrazide–hydrazones of choice toward MCF-10A and BALB/3T3 cell lines was lower than that of the azoxystrobin fungicide tested.
