Chiral Insecticide α-Cypermethrin and Its Metabolites: Stereoselective Degradation Behavior in Soils and the Toxicity to Earthworm <i>Eisenia fetida</i>

Yao, Guojun; Jing, Xu; Wang, Peng; Liu, Xueke; Zhou, Zhiqiang; Liu, Donghui

doi:10.1021/acs.jafc.5b03148

Cited by 32 publications

(12 citation statements)

References 30 publications

(50 reference statements)

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“…This point should not be ignored, since the degradation products are more persistent in the environment compared with the parent pyrethroids [123].…”

Section: Discussionmentioning

confidence: 99%

Global occurrence of pyrethroid insecticides in sediment and the associated toxicological effects on benthic invertebrates: An overview

Cheng

Wei

et al. 2017

Journal of Hazardous Materials

251

108

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Pyrethroids are the third most applied group of insecticides worldwide and are extensively used in agricultural and non-agricultural applications. Pyrethroids exhibit low toxicity to mammals, but have extremely high toxicity to fish and non-target invertebrates. Their high hydrophobicity, along with pseudo-persistence due to continuous input, indicates that pyrethroids will accumulate in sediment, pose long-term exposure concerns to benthic invertebrates and ultimately cause significant risk to benthic communities and aquatic ecosystems. The current review synthesizes the reported sediment concentrations of pyrethroids and associated toxicity to benthic invertebrates on a global scale. Geographically, the most studied area was North America, followed by Asia, Europe, Australia and Africa. Pyrethroids were frequently detected in both agricultural and urban sediments, and bifenthrin and cypermethrin were identified as the main contributors to toxicity in benthic invertebrates. Simulated hazard quotients (HQ) for sediment-associated pyrethroids to benthic organisms ranged from 10.5±31.1 (bifenthrin) to 41.7±204 (cypermethrin), suggesting significant risk. The current study has provided evidence that pyrethroids are not only commonly detected in the aquatic environment, but also can cause toxic effects to benthic invertebrates, and calls for better development of accurate sediment quality criteria and effective ecological risk assessment methods for this emerging class of insecticides.

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“…This point should not be ignored, since the degradation products are more persistent in the environment compared with the parent pyrethroids [123].…”

Section: Discussionmentioning

confidence: 99%

Global occurrence of pyrethroid insecticides in sediment and the associated toxicological effects on benthic invertebrates: An overview

Cheng

Wei

et al. 2017

Journal of Hazardous Materials

251

108

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“…The first-order polynomial regression model can intuitively showed the degradation process (Yao et al, 2015). The range of coefficient of determination (R 2 ) by using the first-order polynomial regression model is within 0.97-0.98, indicating the well-fitting with this modelling.…”

Section: Statistical Analysesmentioning

confidence: 79%

Selective influence of cyflumetofen in degradation and ecological risk assessment

et al. 2021

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Pesticide pollution has gradually caused land degradation. In order to avoid this problem, it is recommended to use enantiomeric pesticides that have less impact on the soil. Cyflumetofen's (CYF) microecological environmental assessment at the enantiomer level is unclear. In our study, the degradation of CYF enantiomers and the effect on soil functions are closely related to microorganisms. (+)-CYF enantiomer is degradable preferred and further discovered that related microorganism that degrades enantiomers. CYF enantiomers alter the bacteria structure and decreased the bacteria abundance. The combination of high-throughput and quantitative PCR results showed that the diversity of the (+)-CYF treatment was significantly lower than that of the (À)-CYF (À30.41 to 44.60) treatment, and the (+)-CYF treatment (À27.80% to 56.70%) was more capable of causing the decrease in the number of soil microorganisms. In addition, (+)-CYF severely interferes with nitrogen cyclingrelated functions. Furthermore, the soil microbial structure was changed to its original level by enantiomers posed. In the study of nitrogen cycle functions, we found that both enantiomers can restrain the abundance of nitrogen cycle-related genes, especially the (+)-CYF treatment decreased more. Canonical correspondence analysis (CCA) showed that g-Massilia and g-Arthrobacter are closely related to nitrogen fixation genes and nitrification genes, and degradation of the two enantiomers of CYF by g-Arthrobacter is closely related. The biological effects of CYF enantiomers remain unclear. Bioassay results show that enantiomers have similar virulence to Tetranychus cinnabarinus. Therefore, while achieving the prevention and control effect, the use of a single isomer (+)-CYF has a higher potential risk to the soil ecosystem.

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“…1 Considering their outstanding insecticidal potency and relatively low toxicity, pyrethroids have been widely used in agriculture and households over the past several decades. 2 The worldwide usage of pyrethroids has been anticipated to be further increased with the ban or restriction on organophosphorus and organochlorine pesticide in many countries. 3,4 Based on chemical structures, pyrethroids are classified into type I and type II categories.…”

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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Chiral Insecticide α-Cypermethrin and Its Metabolites: Stereoselective Degradation Behavior in Soils and the Toxicity to Earthworm Eisenia fetida

Cited by 32 publications

References 30 publications

Global occurrence of pyrethroid insecticides in sediment and the associated toxicological effects on benthic invertebrates: An overview

Global occurrence of pyrethroid insecticides in sediment and the associated toxicological effects on benthic invertebrates: An overview

Selective influence of cyflumetofen in degradation and ecological risk assessment

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

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