Systemic stereoselectivity study of flufiprole: Stereoselective bioactivity, acute toxicity and environmental fate

Tian, Mingming; Zhang, Qing; Hua, Xiude; Tang, Bowen; Gao, Beibei; Wang, Minghua

doi:10.1016/j.jhazmat.2016.08.045

Cited by 44 publications

(36 citation statements)

References 27 publications

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“…Stereoisomers may differ in their ability to bind to the target biological receptor due to their different absolute molecular configurations. 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 .…”

Section: Resultsmentioning

confidence: 99%

“…Tian et al . reported that R‐flufiprole was approximately 3.7–5.7 times more toxic to Scenedesmus obliquus and Trichogramma japonicum Ashmead than the S‐flufiprole . Therefore, individual stereoisomers of the chiral pesticides showed distinct acute toxicities against different non‐target organisms.…”

Section: Resultsmentioning

confidence: 99%

“…For example, (R)-flufiprole is better able to block the passage of chloride ions in the -aminobutyric acid receptor, which resulted in a higher bioactivity of (R)-flufiprole than (S)-flufiprole toward agricultural pests. 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.…”

Section: Stereoselective Fungicidal Activity Of Bromothalonilmentioning

confidence: 99%

“…reported that R-flufiprole was approximately 3.7-5.7 times more toxic to Scenedesmus obliquus and Trichogramma japonicum Ashmead than the S-flufiprole. 22 Therefore, individual stereoisomers of the chiral pesticides showed distinct acute toxicities against different non-target organisms. Although the reason for the different toxicities of the stereoisomers is not clear, it may be related to metabolism differences, including biological enzyme interactions, bioaccumulation, and biotransformation.…”

Section: Stereoselective Acute Toxicity Of Bromothalonil Against Eartmentioning

confidence: 99%

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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: 99%

Section: Resultsmentioning

confidence: 99%

Section: Stereoselective Fungicidal Activity Of Bromothalonilmentioning

confidence: 99%

Section: Stereoselective Acute Toxicity Of Bromothalonil Against Eartmentioning

confidence: 99%

See 2 more Smart Citations

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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“…3,4 Based on chemical structures, pyrethroids are classified into type I and type II categories. [6][7][8] The enantioselective accumulation, degradation, metabolism, and toxicity of pyrethroid enantiomers have been widely studied in recent years. 5 Structurally, pyrethroids contain 1 to 3 asymmetric carbon atoms and result in 1 to 4 pairs of enantiomers, which generally exhibit similar physicochemical and chemical properties in nonchiral environment and different bioactivities in organisms because of different interaction capabilities between enantiomers and naturally chiral biomolecules.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric separation of type I and type II pyrethroid insecticides with different chiral stationary phases by reversed‐phase high‐performance liquid chromatography

Zhang

Qian

et al. 2017

Chirality

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The enantiomeric separation of type I (bifenthrin, BF) and type II (lambda-cyhalothrin, LCT) pyrethroid insecticides on Lux Cellulose-1, Lux Cellulose-3, and Chiralpak IC chiral columns was investigated by reversed-phase high-performance liquid chromatography. Methanol/water or acetonitrile/water was used as mobile phase at a flow rate of 0.8 mL/min. The effects of chiral stationary phase, mobile phase composition, column temperature, and thermodynamic parameters on enantiomer separation were carefully studied. Bifenthrin got a partial separation on Lux Cellulose-1 column and baseline separation on Lux Cellulose-3 column, while LCT enantiomers could be completely separated on both Lux Cellulose-1 and Lux Cellulose-3 columns. Chiralpak IC provided no separation ability for both BF and LCT. Retention factor (k) and selectivity factor (α) decreased with the column temperature increasing from 10°C to 40°C for both BF and LCT enantiomers. Thermodynamic parameters including ∆H and ∆S were also calculated, and the maximum R were not always obtained at lowest temperature. Furthermore, the quantitative analysis methods for BF and LCT enantiomers in soil and water were also established. Such results provide a new approach for pyrethroid separation under reversed-phase condition and contribute to environmental risk assessment of pyrethroids at enantiomer level.

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Simultaneous determination of penthiopyrad enantiomers and its metabolite in vegetables, fruits, and cereals using ultra‐high performance liquid chromatography–tandem mass spectrometry

Zhao

Liu

Liang

et al. 2021

J of Separation Science

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Penthiopyrad is a novel succinate dehydrogenase inhibitor that has one chiral center and exists a metabolite, 1-methyl-3-trifluoromethyl-1H-pyrazole-4carboxamide in its residue definition. An efficient analytical method for the simultaneous determination of penthiopyrad enantiomers and its metabolite in eight matrices were developed using modified quick, easy, cheap, effective, rugged, safe method, coupled with chiral stationary phase and ultra-high performance liquid chromatography-tandem mass spectrometry. The absolute configuration of penthiopyrad enantiomers was confirmed by polarimetry and electronic circular dichroism. Eight polysaccharide-based chiral stationary phases were evaluated in terms of the enantioseparation of penthiopyrad and separation-related factors (the mobile phase, flow rate and the column temperature) were optimized. To obtain an optimal purification, different sorbent combinations were assessed. The linearities of this method were acceptable in the range of 0.005 to 1 mg/L with R 2 > 0.998, while the limits of detection and quantification were 0.0015 mg/kg and 0.01 mg/kg for two enantiomers and its metabolite. The average recoveries of R-(-)-penthiopyrad, S-(+)-penthiopyrad and the metabolite ranged from 75.4 to 109.1, 69.5 to 112.8, and 70.0 to 108.5%, respectively. The intra-day and inter-day relative standard deviations were less than 18.8%. The analytical method was accurate and convenient, which can support their further research on stereoselective degradation, residual monitoring and risk assessment.

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Systemic stereoselectivity study of flufiprole: Stereoselective bioactivity, acute toxicity and environmental fate

Cited by 44 publications

References 27 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

Enantiomeric separation of type I and type II pyrethroid insecticides with different chiral stationary phases by reversed‐phase high‐performance liquid chromatography

Simultaneous determination of penthiopyrad enantiomers and its metabolite in vegetables, fruits, and cereals using ultra‐high performance liquid chromatography–tandem mass spectrometry

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