Synthesis and study of the fungicidal activity of substituted 1-[(2-benzyl-1,3-dioxolan-4-yl)methyl]-1H-imidazoles, 1-[(2-benzyl-1,3-dioxolan-4-yl)methyl]-1H-1,2,4-triazoles and 4-[(2-benzyl-1,3-dioxolan-4-yl)methyl]-4H-1,2,4-triazoles

• Published in: Journal of pharmaceutical sciences and research 2018-07, Vol.10 (7), p.1780-1783
• Main Authors: Talismanov, V S, Popkov, S V, Zykova, S S, Karmanova, O G
• Format: Article
• Language: English
• Subjects: Chromatography; Cytochrome; Pesticides; Pharmaceutical sciences; Sodium
• ISSN: 0975-1459

Sclerotinia sclerotiorum (S.s.) - causative agent of white rot, Fusarium oxysporum (F.o.), Fusarium moniliforme (F.m.) - causative agent of Fusarium wilt, Bipolaris sorokiniana (B.s.) - causative agent of helminthosporium root rot, Rhizoctonia solani (R.s.) - causative agent of brown rot - Rhizoctonia rot and Venturia inaequalis (V.i.) - causative agent of apple scab. Procedure for purification and separation of 1,2,4triazole alkylation products by gradient flash chromatography. 4.0 g of the technical product of alkylation of the sodium salt of 1,2,4-triazole with substituted 4-chloromethyl-1,3dioxolane 4a, consisting of products 4c and 4d, as well as the products of asphaltization and polyalkylation, were dissolved in 15 ml of 7:3 hexane-acetone mixture and applied to the chromatographic column. A filter with silica gel containing the other isomer was dried from the previous eluent and eluted with 200 ml of a chloroform-methanol (10:1) system, collecting fractions with Rf = 0.15 (in a chloroform-methanol (10:1) system), fractions were combined and the solvent was evaporated in vacuum; 1.15 g (26%) of the 4-({2-(4-chlorophenyl)-2-[(4chlorophenyl)methyl]-1,3-dioxolan-4-yl}methyl)-4H-1,2,4triazole (4d) were derived, m.p. 150-151 °C. NMR/H (CDCl3, 5, ppm, J/Hz): 3.05 (s, 2Н, и-ClPhCHA 3.55-3.79 (m, 2Н, СН2О); 3.84-4.04 (m, 2Н, CH2N); 4.29 (q, 1Н, СНО, 3J=5.4); 6.97, 6.99 (both d, по 1Н, С2,6Н, С6Н4С1СН2, 3J=8.1); 7.13-7.33 (m, 6Н, С2,6Н, С6Н4С1, С3,5Н, С6Н4С1СН2, С3,5Н, С6Н4С1 ); 8.06 (s, 0.5H; CH triaz.); 8.55 (s, 1.5H; CH triaz.). Conclusions In general, substituted 1-[(2-benzyl-1,3-dioxolan-4yl)methyl]-1H-imidazoles, 1-[(2-benzyl-1,3-dioxolan-4yl)methyl]-1H-1,2,4-triazoles showed fungicidal activity exceeding the activity of the reference substances (triadimefon and spiroxamine). [...]the search for new fungitoxic compounds of this series is promising.