Synthesis and fungicidal activity of 2-methylalkyl isonicotinates and nicotinates

• Published in: Medicinal chemistry research Vol. 26; no. 3; pp. 509 - 517
• Main Authors: Huras, Bogumiła, Zakrzewski, Jerzy, Krawczyk, Maria, Bombińska, Danuta, Cieniecka-Rosłonkiewicz, Anna, Michalczyk, Alicja
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.03.2017; Springer Nature B.V
• Subjects: Antibiotics; Biochemistry; Biomedical and Life Sciences; Biomedicine; Cell Biology; Chalkbrood disease; Enrichment; Fungi; Fungicidal activity; Fungicides; Fusarium; Homology; Isomers; Original Research; Oxalates; Oxalic acid; Pharmacology/Toxicology; Phytopathogenic fungi; Isonicotinates; Fungicidal activity; Nicotinates
• ISSN: 1054-2523; 1554-8120
• DOI: 10.1007/s00044-016-1768-7

Homologs and analogs of 2-methylheptyl isonicotinate (new, natural antifungal and antibacterial antibiotic isolated from Streptomyces sp . 201): racemic 2-methylalkyl isonicotinates 4 and nicotinates 5 and enantiomerically enriched in the R and S isomers, 2-methylpentyl isonicotinate and nicotinate were obtained. Fungistatic activity of the compounds was evaluated. Nicotinates 5a – c show significant activity against phytopathogenic fungi: Fusarium culmorum , Phytophthora cactorum , Rhizoctonia solani . The activity of the enantiomerically enriched compounds was comparable to the activity of racemic ones. There was no significant difference in fungistatic activity between the enantiomerically enriched R and S isomers. Investigated compounds and their oxalates have proven to be active against chalkbrood disease caused by fungal species Ascosphaera apis . The activity of the nicotinates 5a and 5b and oxalates 5a – c against Ascosphaera apis was higher than the activity of oxalic acid itself. Especially high activity was shown for 2-methylbutyl nicotinate 5a and oxalate of 2-methylpentyl nicotinate 5b . Graphical abstract