Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Li, Lianshan; Gao, Beibei; Wen, Yong; Zhang, Zhaoxian; Chen, Rou; He, Zongzhe; Kaziem, Amir E.; Shi, Haiyan; Wang, Minghua

doi:10.1002/ps.5520

Cited by 41 publications

(28 citation statements)

References 29 publications

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“…For example, (R)‐flufiprole is better able to block the passage of chloride ions in the γ‐aminobutyric acid receptor, which resulted in a higher bioactivity of (R)‐flufiprole than (S)‐flufiprole toward agricultural pests . The stereoselective bioactivity of bitertanol stereoisomers correlated with the binding distance and calculated energy difference between the stereoisomers and the target protein . In this study, bromothalonil enantiomers exhibited distinct inhibitory activities against different fungal species.…”

Section: Resultsmentioning

confidence: 69%

“…22 The stereoselective bioactivity of bitertanol stereoisomers correlated with the binding distance and calculated energy difference between the stereoisomers and the target protein. 23 In this study, bromothalonil enantiomers exhibited distinct inhibitory activities against different fungal species. Especially, bromothalonil enantiomers showed the opposite inhibitory effects against C. cliviicola and C. musae, both of which belong to the Colletotrichum spp.…”

Section: Stereoselective Fungicidal Activity Of Bromothalonilmentioning

confidence: 71%

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Systemic stereoselectivity study of bromothalonil: stereoselective bioactivity, toxicity, and degradation in vegetables and soil

Liang

Huang

et al. 2020

Pest Management Science

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BACKGROUND The chiral pesticide bromothalonil is widely used to control anthracnose disease on fruits and vegetables in China. The pesticidal activity, ecotoxicological effects and environmental behavior of bromothalonil and its enantiomers are still unclear. RESULTS Bromothalonil presented effective biocidal activities against the tested fungi, its enantiomers showed distinct inhibitory activities against different fungal species. The bioactivities of (+)‐bromothalonil was 1.29–10.77 times higher than (−)‐bromothalonil toward Rhizoctonia solani, Botrytis cinerea, Curvularia lunata, Corynespora cassiicola, Colletotrichum siamense, and Colletotrichum musae, while the effect pattern was opposite for Colletotrichum cliviicola. Based on the acute toxicity test, bromothalonil was very toxic to Eisenia foetida (E. foetida). Bromothalonil also damaged the lysosomal membrane and exhibited potential genotoxicity toward E. foetida. Moreover, (+)‐bromothalonil presented lower toxicity than (−)‐bromothalonil. Stereoselective degradation was investigated in tomato, cucumber, chieh‐qua, and soil. The half‐life values of bromothalonil degradation ranged from 7.14 to 24.75 days, indicating that bromothalonil was easily degraded. Additionally, (+)‐bromothalonil degraded 1.2–1.75 times faster than (−)‐bromothalonil in the four matrices. CONCLUSION This is the first systemic assessment of the stereoselectivity of bromothalonil. Based on the obtained half‐life, EC50 and LC50 values, bromothalonil is an easily degraded, broad‐spectrum biocidal but very toxic pesticide. (+)‐Bromothalonil was more degradable in vegetables and soil and showed clearly higher bioactivity toward target organisms and lower toxicity to E. foetida than (−)‐bromothalonil. Therefore, the stereoselectivity of bromothalonil enantiomers should be fully considered in comprehensive environmental and ecological risk assessments in future work. © 2020 Society of Chemical Industry

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Section: Resultsmentioning

confidence: 69%

Section: Stereoselective Fungicidal Activity Of Bromothalonilmentioning

confidence: 71%

Systemic stereoselectivity study of bromothalonil: stereoselective bioactivity, toxicity, and degradation in vegetables and soil

Liang

Huang

et al. 2020

Pest Management Science

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“…Therefore, the antifungal activity of pydiflumetofen may be derived mainly from the R enantiomer. Li et al 31 reported that (1R,2R)-bitertanol and (1S,2R)bitertanol exhibited higher activity than (1S,2S)-bitertanol and (1R,2S)-bitertanol on all pathogens by a factor of 4.3-314.7 times. Dong et al 32 reported that a 24.2-fold difference in bioactivity was found between difenoconazole enantiomers.…”

Section: Resultsmentioning

confidence: 99%

Evaluation of exploitive potential for higher bioactivity and lower residue risk enantiomer of chiral fungicide pydiflumetofen

Wang

Zhang

et al. 2021

Pest Management Science

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BACKGROUND: Pydiflumetofen, as a new succinate dehydrogenase inhibitor (SDHI) chiral fungicide, has been used in crop production because of its broad-spectrum and high-efficiency antifungal activity. However, little is known about pydiflumetofen at the chiral level. The stereoselective bioactivity and degradation of pydiflumetofen enantiomers were therefore investigated. RESULTS: Pydiflumetofen presented effective bioactivity against the eight tested phytopathogens, and its enantiomers showed significant differences in activity. The bioactivity of R-pydiflumetofen was 9.0-958.8 times higher than that of the S enantiomer. Treatment with R-pydiflumetofen increased the cell membrane permeability of Sclerotinia sclerotiorum and decreased exopolysaccharide and oxalic acid production more than treatment with S-pydiflumetofen. Furthermore, R-pydflumetofen exhibited better inhibitory activity against the succinate dehydrogenase enzyme of S. sclerotiorum than S-pydiflumetofen by 584-fold. According to homology modeling and molecular docking studies, the binding affinities of the R and S enantiomers were −7.0 and −5.3 kcal mol −1 , respectively. Additionally, the degradation half-lives of Sand R-pydiflumetofen in three vegetables (cucumber, eggplant, and cowpea) under field conditions were 2.56-3.12 days and 2.48-2.76 days, respectively, which reveals that R-pydiflumetofen degrades faster than S-pydiflumetofen.CONCLUSION: Based on the results obtained, R-pydiflumetofen not only exhibited a higher bactericidal activity, but also posed fewer residual risks in the environment. The mechanism of the stereoselective bioactivity was correlated with the stereoselective inhibition activity of the target enzyme and affected the cell membrane permeability and the production of exopolysaccharide and oxalic acid. This research could provide a foundation for the systematic evaluation of pydiflumetofen from an enantiomeric view.

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“…In addition to its antibacterial effects, studies have also examined its residues on fruits and vegetables using an achiral analytical method (Farha et al., 2016; JMPR, 2008; H. Zhang et al., 2014). However, some cases have already shown that achiral research results of chiral fungicides cannot accurately describe their biological activity, toxicity, metabolites, and environmental behavior because pure enantiomers tend to display different properties in biological systems due to their stereostructural differences (Dong et al., 2013; Kaziem et al., 2020; Li et al., 2019; Li et al., 2020; Liang et al., 2020; Pan et al., 2018; Zhang et al., 2015). Therefore, research on mandipropamid at the enantiomer level is crucial.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective environmental behavior of the chiral fungicide mandipropamid in four types of Chinese soil

Han

Chen

Liu

et al. 2021

Soil Science Soc of Amer J

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Enantioselective degradation behavior of mandipropamid, and factors affecting its degradation and metabolites in four types of Chinese soil were investigated in this work. The results showed that the enantiomeric selectivity values ranged from 0.025 to 0.170, indicating that enantioselectivity was found in the degradation process of the racemate in all of the soil samples and that the R-(−)-enantiomer was preferentially degraded. The degradation compounds formed faster in native alkaline soils (half-lives = 35.5-39.80 d) than in native acidic soils (half-lives = 51.3-77.90 d). The half-lives of the R-(−)-enantiomer and S-(+)-enantiomer were 35.5-73.7 and 37.5-77.9 d, 66.6-97.6 and 70.0-103.5 d, and 52.5-110.0 and 66.0-144.4 d in the fourtypes of soil under native, sterilized, and organic matter-removed conditions, respectively, which indicated that mandipropamid degradation can be attributed to microbial activity and the organic matter content in the soil. Furthermore, the half-lives of the R-(−)-enantiomer and S-(+)-enantiomer decreased 1.07-1.95 and 1.08-1.79 times with each 10˚C increase in incubation temperature, and the half-lives of the R-(−)-enantiomer and S-(+)-enantiomer decreased 1.09-1.43 and 1.06-1.50 times with increasing moisture content. However, the incubation temperature and soil moisture did not change the enantioselectivity. Mandipropamid enantiomers were observed to be configurationally stable in the selected soil, and no interconversion was found during the incubation of enantiopure R-(−)-mandipropamid or S-(+)-mandipropamid in native or sterilized soil. During the degradation process, four major metabolites were detected. In comprehensive consideration of the environmental behavior, the enantioselective degradation results should be considered to more accurately assess the risk of this chiral pesticide in a real environment.

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Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Cited by 41 publications

References 29 publications

Systemic stereoselectivity study of bromothalonil: stereoselective bioactivity, toxicity, and degradation in vegetables and soil

Systemic stereoselectivity study of bromothalonil: stereoselective bioactivity, toxicity, and degradation in vegetables and soil

Evaluation of exploitive potential for higher bioactivity and lower residue risk enantiomer of chiral fungicide pydiflumetofen

Enantioselective environmental behavior of the chiral fungicide mandipropamid in four types of Chinese soil

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