Synthesis and Antifungal Activity of Novel Tetrahydrogeranyl Quaternary Ammonium Salts

Abstract

Due to the excessive use of antifungal agents, drug resistance and ecological problems are increasing. Some antifungal agents are difficult to degrade and have high toxicity and several side effects. In this study, 15 novel tetrahydrogeranyl quaternary ammonium salts (8a–8o) were synthesized from the natural compound citral. The structures of the quaternary ammonium salts were characterized by Fourier transform infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance spectroscopy, and mass spectrometry, and the antifungal activities of these compounds at a concentration of 0.25 mg/mL against 10 plant pathogenic fungi were tested. The results showed that compound 8i had the best antifungal activity, and its inhibition rates against Rhizoctonia solani, Phytophthora parasitica var. nicotianae, Sphaeropsis sapinea, Fusarium oxysporum f. sp. niveum, and Poria vaporaria reached 100%. For Fusarium verticillioides, the inhibition rate of compound 8i was 93.28%, which was higher than that of chlorothalonil. In addition, it was found that the inhibition rates of compounds with N,N-di- n-propyl group (8l, 8m) against R solani, F oxysporum f. sp. niveum, S sapinea, P parasitica var. nicotianae, F verticillioides, Colletotrichum acutatum, and Coriolus versicolor were higher than compounds with N,N-diethyl and N,N-dimethyl groups (8a, 8b, 8j, 8k). The inhibition rates of compounds with morpholine groups (8n, 8o) were generally low.