Esfenvalerate
(Synonyms: S-氰戊菊酯) 目录号 : GC63637
Esfenvalerate 是拟除虫菊酯杀虫剂 fenvalerate 的四个异构体之一。
Cas No.:66230-04-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Esfenvalerate is one of the four isomers of the pyrethroid insecticide fenvalerate[1].
Esfenvalerate (0.1, 1, 7.5 or 15 mg/kg/day; gavage; from gestation day (GD) 13 to 19) shows clinical signs of neurotoxicity with 15 mg/kg/day[1].
[1]. Anne-Marie Saillenfait, et al. The Pyrethroid Insecticides Permethrin and Esfenvalerate Do Not Disrupt Testicular Steroidogenesis in the Rat Fetus. Toxicology. 2018 Dec 1;410:116-124.
| Cas No. | 66230-04-4 | SDF | |
| 别名 | S-氰戊菊酯 | ||
| 分子式 | C25H22ClNO3 | 分子量 | 419.9 |
| 溶解度 | DMSO : 100 mg/mL (238.15 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.3815 mL | 11.9076 mL | 23.8152 mL |
| 5 mM | 0.4763 mL | 2.3815 mL | 4.763 mL |
| 10 mM | 0.2382 mL | 1.1908 mL | 2.3815 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Chemistry and fate of fenvalerate and Esfenvalerate
Rev Environ Contam Toxicol 2003;176:137-54.PMID:12442505DOI:10.1007/978-1-4899-7283-5_3.
Fenvalerate is listed under Class IV of the U.S. Food and Drug Administration (USFDA) Surveillance Index Classification, indicating a low hazard potential to humans from both exposure and toxicological standpoints; thus, minimal monitoring is required (Reed 1981; Eisler 1992). To date, monitoring efforts have been of limited value in evaluating concentrations of fenvalerate and its subsequent risk to the environment. Few regulations currently exist for protection of sensitive natural resources against fenvalerate or Esfenvalerate, although current application rates may be lethal to many nontarget species, including bees, fish, and aquatic invertebrates. Additional monitoring is recommended to measure residues in the environment and evaluate risks associated with use. It is clear that both fenvalerate and Esfenvalerate are considerably less harmful to the environment and most nontarget organisms than most other insecticides. They are considerably less persistent and more selective in their toxicity, except for their high degree of toxicity to fish and aquatic invertebrates. However, they are moderately persistent in soils and, because of low water solubilities, high octanol-water partition coefficients (Kow), and moderate persistence, both fenvalerate and Esfenvalerate have been identified as having the potential to accumulate in aquatic sediments and biota (Nowell et al. 1999). Numerous studies of fenvalerate dynamics in soils indicate that it is relatively immobile and readily degraded. In almost all cases, the degradation products formed are less toxic than the parent insecticide. However, some degradation products from fenvalerate may demonstrate elevated toxicity, and more research into and increased monitoring of abiotic degradation may be warranted. Results from environmental monitoring are minimal at best and do not adequately support research done in the laboratory. These results are critical for accurately determining the risk these insecticides pose to the environment. The pyrethroids are poised to fill the gap left in the insecticide market with the impending suspension of many of the organophosphates and possibly at least some carbamates. One agent, chlorpyrifos, has already been heavily restricted by the U.S. Environmental Protection Agency (USEPA), and one manufacturer has ceased production. The environmental risk posed by both fenvalerate and Esfenvalerate can change significantly with increased application, and current information is not sufficient to adequately assess the risk that a dramatic rise in use would pose. Future efforts should focus on increased environmental monitoring and research on Esfenvalerate fate with increased and repeated application. Pyrethroids, including fenvalerate and Esfenvalerate, have also recently been linked to endocrine disruption (Garey and Wolff 1998; Go et al. 1999). Endocrine disruption is an emerging field, and more research is essential in documenting and managing these types of effects. Research into the bioavailability and dynamics of Esfenvalerate at the sediment-water interface is also of key importance. Current information indicates that resuspension or desorption from soils should be minimal, but this is not equivalent to the fraction of sediment-sorbed Esfenvalerate that may be bioavailable to sensitive aquatic species. In terms of risk, fenvalerate and Esfenvalerate are significant improvements over many of their predecessors, but it is clear that more information is needed to fully support this conclusion.
The pyrethroid Esfenvalerate induces hypoactivity and decreases dopamine transporter expression in embryonic/larval zebrafish (Danio rerio)
Chemosphere 2020 Mar;243:125416.PMID:31995874DOI:10.1016/j.chemosphere.2019.125416.
Esfenvalerate is a pyrethroid insecticide used widely for agricultural and residential applications. This insecticide has been detected in aquatic environments at concentrations that can induce sub-lethal effects in organisms. In this study, zebrafish embryos were used to examine the effects of environmentally-relevant concentrations of Esfenvalerate on development and behavior. It was hypothesized that Esfenvalerate exposure would impair locomotion due to its effects on the central nervous system. We also measured mitochondrial bioenergetics and the expression of genes (dopamine system) as putative mechanisms of locomotor impairment. Concentrations of 0.02, 0.2 and 2 μg/L Esfenvalerate did not induce significant mortality nor deformity in zebrafish, but there was an acceleration in hatching time for zebrafish exposed to 2 μg/L Esfenvalerate. As an indicator of neurotoxicity, the Visual Motor Response (VMR) test was conducted with 5, 6, and 7 dpf zebrafish after continuous exposure, and higher concentrations were used (4 and 8 μg/L Esfenvalerate) to better discern age-and dose dependent responses in behavior. Experiments revealed that, unlike the other stages, 6 dpf larvae showed evidence for hypo-activity with Esfenvalerate, suggesting that different stages of larval development may show increased sensitivity to pyrethroid exposure. This may be related to age-dependent maturation of the central nervous system. We hypothesized that reduced larval activity may be associated with impaired production of ATP and the function of mitochondria at earlier life stages, however dramatic alterations in oxidative phosphorylation were not observed. Based on evidence that dopamine regulates behavior and studies showing that other pyrethroids affect dopamine system, we measured transcripts involved in dopaminergic signaling. We found that dopamine active transporter was down-regulated with 0.2 μg/L Esfenvalerate. Lastly, we comprehensively summarize the current literature (>20 studies) regarding the toxicity of pyrethroids in zebrafish, which is a valuable resource to those studying these pesticides. This study demonstrates that Esfenvalerate at environmentally-relevant levels induces hypoactivity that are dependent upon the age of the zebrafish, and these behavioral changes are hypothesized to be related to impaired dopamine signaling.
Esfenvalerate biodegradation by marine fungi is affected by seawater and emulsifier formulation
Environ Sci Pollut Res Int 2023 Mar;30(13):38394-38408.PMID:36580257DOI:10.1007/s11356-022-24921-6.
Pesticides already were detected in the oceans, and their fates require evaluation in these environmental conditions. Therefore, marine-derived fungi were assessed for Esfenvalerate biodegradation, approaching the effects of seawater and use of commercial emulsifiable formulation. Residual pesticide and four metabolites were quantified. Furthermore, kinetics were determined for the three tested strains (Microsphaeropsis sp. CBMAI 1675, Acremonium sp. CBMAI 1676, and Westerdykella sp. CBMAI 1679). These facultative marine fungi biodegraded up to 87 ± 2% of 100 mg L-1 Esfenvalerate in liquid media. However, Esfenvalerate biodegradation was faster in low salinity conditions than in artificial seawater. Moreover, rates of consumption were higher for Esfenvalerate in the pure form than for the commercial emulsifiable formulation. These results suggest that half-life of Esfenvalerate formulated with inert ingredients in seawater can have a double prolongation effect that can contribute to health and environmental issues.
Effects of the Pyrethroid Esfenvalerate on the Oligochaete, Lumbriculus variegatus
Bull Environ Contam Toxicol 2016 Apr;96(4):438-42.PMID:26693935DOI:10.1007/s00128-015-1718-y.
Esfenvalerate is a neurotoxic pyrethroid insecticide widely used for agricultural and residential purposes and is considered toxic to nontarget organisms such as fish and aquatic invertebrates. In this study, we evaluated the toxicity of Esfenvalerate on the aquatic oligochaete Lumbriculus variegatus. In the acute test, organisms showed visible signs of stress but no LC50 value could be determined. In the 28-day chronic test, a significant decrease in reproduction was observed with a NOEC value of 0.25 µg/kg and a LOEC value of 2.34 µg/kg. As for biomass per worm, a significant decrease was also observed with a NOEC value of 2.34 µg/kg and a LOEC value of 36.36 µg/kg. Reproductive impairment and reductions in biomass of L. variegatus exposed to environmentally realistic concentrations of Esfenvalerate observed in laboratory tests suggests potential deleterious effects of this pyrethroid on oligochaete natural populations.
Effects of dietary Esfenvalerate exposures on three aquatic insect species representing different functional feeding groups
Environ Toxicol Chem 2008 Aug;27(8):1721-7.PMID:18616382DOI:10.1897/07-501.1.
Given the chemical properties of synthetic pyrethroids, it is probable that compounds, including Esfenvalerate, that enter surface waters may become incorporated into aquatic insect food sources. We examined the effect of dietary Esfenvalerate uptake in aquatic insects representing different functional feeding groups. We used three field-collected aquatic insect species: A grazing scraper, Cinygmula reticulata McDunnough (Ephemeroptera: Heptageniidae); an omnivorous filter feeder, Brachycentrus americanus Banks (Trichoptera: Brachycentridae); and a predator, Hesperoperla pacifica Banks (Plecoptera: Perlidae). Laboratory-cultured algae were preexposed for 24 h to Esfenvalerate concentrations of 0, 0.025, 0.05, and 0.1 microg/L and provided to two C. reticulata age classes (small and final-instar nymphs). Reduction in small nymph growth was observed following three weeks of feeding on algae exposed to 0.05 and 0.1 microg/L of Esfenvalerate, and the highest dietary exposure reduced egg production in final-instar nymphs. The diet for B. americanus and H. pacifica consisted of dead third-instar Chironomus tentans larvae preexposed for 24 h to Esfenvalerate concentrations ranging between 0.1 and 1.0 microg/L. Consumption of larvae exposed to 0.5 to 1.0 microg/L of Esfenvalerate caused case abandonment and mortality in B. americanus caddisfly larvae. Although H. pacifica nymphs readily consumed esfenvalerate-exposed larvae, no adverse effects were observed during the present study. Furthermore, no evidence of esfenvalerate-induced feeding deterrence was found in any of the species tested, suggesting that aquatic insects may not be able to distinguish between pyrethroid-contaminated and uncontaminated food sources. These findings indicate that feeding deterrence is not a factor in regulating aquatic insect dietary exposures to synthetic pyrethroids.