The biological activities of prothioconazole enantiomers and their toxicity assessment on aquatic organisms

• Published in: Chirality (New York, N.Y.) Vol. 31; no. 6; pp. 468 - 475
• Main Authors: Zhai, Wangjing, Zhang, Linlin, Cui, Jingna, Wei, Yimu, Wang, Peng, Liu, Donghui, Zhou, Zhiqiang
• Format: Journal Article
• Language: English
• Published: United States Wiley Subscription Services, Inc 01.06.2019
• Subjects: Acute toxicity; Alternaria - drug effects; Animals; Antifungal activity; Aquatic ecosystems; Aquatic organisms; Ascomycota - drug effects; Biocompatibility; Biological activity; Chlorella - drug effects; Chlorella pyrenoidosa; Daphnia - drug effects; Drug Evaluation, Preclinical - methods; Duckweed; Enantiomers; enantioselective; Fungi; Fungicides; Fungicides, Industrial - chemistry; Fungicides, Industrial - pharmacology; Fungicides, Industrial - toxicity; Fusarium - drug effects; Magnaporthe - drug effects; Organisms; Plant Diseases - microbiology; prothioconazole; Rice blast; Stereoisomerism; Toxicity; Toxicity Tests, Acute; Triazoles - chemistry; Triazoles - pharmacology; Triazoles - toxicity; Water Pollutants, Chemical - chemistry; Water Pollutants, Chemical - toxicity; Wheat; toxicity; biological activity; prothioconazole; enantioselective
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.23075

Chiral fungicide prothioconazole has a wide range of antifungal spectrum; however, little research has been conducted to evaluate prothioconazole on an enantiomeric level. Five target pathogens and three common aquatic organisms were tested for the enantioselective bioactivity and toxicity of prothioconazole in this work. The antifungal activity of the enantiomers against wheat phytoalexin, rice blast fungus, exserohilum turcicum, Alternaria triticina, and Fusarium avenaceum was determined, and it was found that (−)‐prothioconazole were 85 to 2768 times more active than (+)‐prothioconazole toward these target organisms. In order to reflect the risk to aquatic ecosystem, the acute toxicity of the enantiomers to Daphnia magna, Chlorella pyrenoidosa, and Lemna minor L. was assessed. It was observed that the toxicity of (−)‐prothioconazole to D. magna was 2.2 times higher than (+)‐prothioconazole, but it was lower to C. pyrenoidosa and L. minor L. The toxicities of (+)‐enantiomer and (−)‐enantiomer to D. magna and C. pyrenoidosa were synergy, indicating that the racemate had higher threat to the organisms. It could be concluded that the effects of prothioconazole on target organisms and the acute toxicity to nontarget species were enantioselective with (−)‐enantiomer possessing higher efficiency and lower toxicity. Such enantiomeric differences should be taken into consideration when assessing the performance of prothioconazole.