Enantioselective bioaccumulation and toxicity of the novel chiral antifungal agrochemical penthiopyrad in zebrafish (Danio rerio)

Ren, Bo; Zhao, Tingting; Li, Yanhong; Liang, Hanlin; Zhao, Yuexing; Chen, Haiyue; Li, Li; Liang, Hongwu

doi:10.1016/j.ecoenv.2021.113010

Cited by 27 publications

(8 citation statements)

References 51 publications

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“…In chiral amide fungicides, the enantioseparation mechanism of penflufen was explained by computational chemistry, and S -penflufen was 54 times more toxic to Danio rerio and 148 times more toxic to R. solani. , S -(+)-Penthiopyrad was preferentially accumulated in zebrafish and caused oxidative stress in zebrafish liver …”

Section: Introductionmentioning

confidence: 99%

Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems

Tong

Meng

et al. 2023

J. Agric. Food Chem.

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Fluindapyr is a novel chiral succinate dehydrogenase inhibitor used to control fungal diseases. The enantioselective effects of fluindapyr in paddy ecosystems are unknown. We developed a new chiral determination method of fluindapyr using ultrahigh performance liquid chromatography tandem mass spectrometry. The absolute configuration of the fluindapyr enantiomers was identified by an electron circular dichroism model. A new husk-based biochar material was used to optimize and establish a QuEchERs method for paddy soil determination. Under anaerobic conditions, the half-lives of R-fluindapyr and S-fluindapyr in paddy soil were 69.6 and 101.8 days, respectively. R-fluindapyr degraded more rapidly than S-fluindapyr. S-fluindapyr was 87.8 times more active against Rhizoctonia solani than R-fluindapyr. The enantioselective bioactivity mechanism was illustrated by molecular docking between the fluindapyr enantiomers and SDH of R. solani. The binding powers of R-fluindapyr and S-fluindapyr to proteins were −32.12 and − 42.91 kcal/mol, respectively. This study reports the stereoselectivity of fluindapyr about determination, degradation, bioactivity, and its mechanism. It provides a foundation for an in-depth study of fluindapyr at the enantiomer level.

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Section: Introductionmentioning

confidence: 99%

Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems

Tong

Meng

et al. 2023

J. Agric. Food Chem.

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“…Furthermore, PEN has toxic effects on zebrafish in the early stage and induces malformation during development 14 . Compared with R ‐(−)‐PEN and racemate, S ‐(+)‐PEN causes severe oxidative stress in the zebrafish liver, thereby showing higher toxic effects 15 . Since PEN can be used as a suspending agent or soil drench to control plant diseases, that may increase the residue of PEN in the soil as well as the risk of entering the aquatic environment.…”

Section: Introductionmentioning

confidence: 99%

Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Deng

et al. 2023

Pest Management Science

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BACKGROUND: In order to promote the green development of agriculture, it is important to study the enantioselective effect of chiral pesticides. The bioactivity of the chiral fungicide penthiopyrad (PEN) racemate and enantiomers against phytopathogens, toxicity to non-target organisms, effect on tomato fruit growth and maturation, and environmental fate in tomato cultivation were evaluated at an enantioselective level in this study. RESULTS:The results indicated that at the same efficacy, the optically pure S-(+)-PEN could lower the dosage of racemate by 20-96%. The S-enantiomer had low toxicity to earthworms. Besides, the S-(+)-PEN did not cause significant abiotic stress to the tomato and increased fruit fresh weight and size via modulating the contents of plant hormones. However, the content of hydrogen peroxide (H 2 O 2 ), superoxide (O 2 − ) and malondialdehyde in the R-enantiomer treatment group was significantly higher than the control group. The effect of the racemate on tomato fruit was between the enantiomers. Furthermore, compared to R-(−)-PEN and racemate, the S-enantiomer degraded more quickly in tomato fruit, leaves, and soil, reducing the danger of human exposure. CONCLUSION:The S-enantiomer is highly effective and less toxic. The development of enantiomer pure S-(+)-PEN products might be an efficient and low-risk strategy. The results lay the foundation for comprehensive evaluation and proper application of PEN.

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“…S-(+)-PEN accumulated preferentially in zebrafish and caused oxidative stress in the liver. 8 Liu et al reported that the S-(+)-enantiomer in the racemate was preferentially degraded in four Chinese soils. 9 In addition, the S-enantiomer degraded faster in tomato and cucumber than R-(−)-PEN and the racemate, thereby reducing the risk of human exposure.…”

Section: Introductionmentioning

confidence: 99%

“…Currently, several studies regarding the enantioselectivity of PEN have been published. S-(+)-PEN accumulated preferentially in zebrafish and caused oxidative stress in the liver . Liu et al.…”

Section: Introductionmentioning

confidence: 99%

Combined Analysis of Transcriptome and Metabolome Reveals the Potential Mechanism of the Enantioselective Effect of Chiral Penthiopyrad on Tomato Fruit Flavor Quality

Deng

Liu

et al. 2022

J. Agric. Food Chem.

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This study investigated the enantioselective effects of S-, R-, and rac-penthiopyrad (PEN) on the flavor quality of tomato fruit through the levels of sugars, acids, volatiles, and nutrients and explored the potential mechanism by combined analysis of the transcriptome and metabolome. The results revealed that the S-enantiomer increased the content of soluble sugars while decreasing the content of organic acids, thereby increasing the taste of tomato fruit. Furthermore, S-(+)-PEN promoted the accumulation of volatile compounds and nutrients (total phenols, flavonoids, and vitamin C). Transcriptome and metabolome data showed that the S-enantiomer improved fruit flavor and quality by influencing metabolites and genes in glycolysis, starch and sucrose metabolism, the citrate cycle, and amino acid biosynthesis pathways. However, R-(−)-PEN had a negative effect on tomato flavor. The effect of the racemate on fruit flavor quality was between a pair of enantiomers. The comprehensive data of PEN enantiomers will provide theoretical support for the application of PEN in tomatoes. Thus, developing enantiopure S-(+)-PEN products might be more conducive to the flavor and quality of the tomato fruit.

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Enantioselective bioaccumulation and toxicity of the novel chiral antifungal agrochemical penthiopyrad in zebrafish (Danio rerio)

Cited by 27 publications

References 51 publications

Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems

Enantioselective Degradation and Bioactivity Mechanism of a New Chiral Fungicide Fluindapyr in Paddy Ecosystems

Systemic enantioselectivity study of penthiopyrad: enantioselective bioactivity, acute toxicity, degradation and influence on tomato

Combined Analysis of Transcriptome and Metabolome Reveals the Potential Mechanism of the Enantioselective Effect of Chiral Penthiopyrad on Tomato Fruit Flavor Quality

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