Currently, agricultural production is impossible without the use of chemical plant protection products, so the search for new effective fungicides is an important and urgent task. A significant part of the systemic fungicides and antimycotics used today are azole derivatives. Research conducted at the Department of Chemistry is devoted to the analysis of the fungicidal and biological activity of substances of various classes of organic compounds, including derivatives of azoles. Previously published data on the fungicidal activity of 2-methyl-5-nitrobenzoxazole and its derivatives showed that 2-methyl-5-nitrobenzoxazole shows the highest fungicidal activity for all types of fungal cultures used in the study. The second nitro group introduced into the 2-methyl-5-nitrobenzoxazole molecule reduces fungitoxicity by 1.5-2 times. Replacing the methyl group with phenyl significantly reduces the fungicidal activity. In continuation of these studies, tests of 5-(4'-chlorophenylazo)-7-nitro-8-hydroxyquinoline, 5-(3',5'-dimethoxyphenylazo)-7-nitro-8-hydroxyquinoline and 5-(3'-methyl-4'-nitrophenylazo)-7-nitro-8-hydroxyqui-noline with respect to V. inaequalis, the causative agent of apple scab, R. solani, the causative agent of rhi-zoctonia, F. oxysporum, F. moniliforme, causative agents of cereal crops, B. sorokiniana – causative agent of root rot and S. sclerotiorum – causative agent of white rot. The radial growth of mycelium was determined according to the method developed by NIITEKHIM, according to which the fungal cultures were sown in nutrient media with the addition of the studied substan-ces. In parallel, a control experiment was conducted in the aquatic environment. The growth of mycelia was controlled by measurements on days 3, 6 and 9. The percentage of inhibition of fungal growth was calculated using the Abbott formula. Analysis of the experimental data demonstrates a higher fungicidal activity of 5-(3',5'-dimethoxy-phenylazo)-7-nitro-8-hydroxyquinoline compared with other azoquinolines for all types of fungal cultures used in the study.

The synthesis of new derivatives of 3-azabicyclononan is one of the urgent tasks of modern synthetic organic chemistry. 3-Azabicyclononan is a structural analogue of the cytisine alkaloid, which is a strong agonist of acetylcholine receptors. Among synthetic heterocycles containing a 3-azabicyclo[3.3.1]nonane fragment, compounds with different types of biological activity have been discovered at present: analgesic, anti-inflammatory, antimicrobial, antioxidant, and others. The introduction of a fragment of azabicyclononan into the amino acid structure can lead to a limitation of the conformational mobility of a new molecule, as a result of which the activity and selectivity of its interaction with the receptor will increase. We synthesized 2-(1,9-dinitro-8-oxo-6,11-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-yl)acetic acid and 2-(1,9-dinitro-8-oxo-13-(2-oxopropyl)-6,11-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-11-yl)acetic acid by the interaction of annionic σ-complexes 5,7-dinitro-8-hydroxyquinoline with glycine under Mannich condensation in high yield. At the beginning, when 5,7-dinitro-8-hydroxyquinoline NaBH4 was applied in DMF or acetone carbanion in DMSO, the corresponding anionic complexes were synthesized. The resulting adducts were isolated from the reaction mixture, dissolved in cold water, and an aminomethylating mixture consisting of formaldehyde and an amino acid was added. As a result, 3-azabicyclo[3.3.1]nonane derivatives are formed, annelated with a pyridine ring and containing an amino acid residue. By the methods of NMR and IR spectroscopy, as well as high-resolution mass spectrometry, the structure of the obtained compounds was proved. Thus, in the 1H NMR spectra of the synthesized compounds, a signal of the proton of the carboxyl group in the form of a broadened singlet is detected in a weak spectral region. Equatorial and axial protons of an alicyclic fragment form a characteristic system of signals in the range δ 3.20-3.60 ppm. In the IR spectra of these molecules, the vibrational bands of carbonyl groups at ν 1720 cm–1, as well as the vibrational bands of the C–O bond of the carboxyl group at ν 1198 cm–1, are fixed. The m/z values in the high resolution mass spectra correspond to the molecular weights of the synthesized diazatricycclotridecans.

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