esfenvalerate
fenvalerate A
Identification
| Name | esfenvalerate |
| IUPAC | [(R)-cyano-(3-phenoxyphenyl)methyl] (2R)-2-(4-chlorophenyl)-3-methylbutanoate |
| CAS Number | 66230-04-4 |
| FDA UNII | 7F07OXM0PP |
| Molecular Formula | C25 H22 Cl N O3 |
| Molecular Weight | 419.90694000 |
| MDL Number | MFCD00203302 |
| Beilstein | 4275674 |
| XlogP3 | 6.20 (est) |
Regulatory
Physical Properties
| Appearance | white crystalline solid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 59.50 °C. @ 760.00 mm Hg |
| Boiling Point | 538.90 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 1.500000 mmHg @ 25.00 °C. (est) |
| Flash Point | 535.00 °F. TCC ( 279.70 °C. ) (est) |
| logP (o/w) | 6.220 |
| Soluble in | water, 0.002 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-rat LD50 325 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 2000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | herbicides / pesticides |
| Recommendation for esfenvalerate usage levels up to | not for fragrance use. |
| Recommendation for esfenvalerate flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
asana XL
benzeneacetic acid, 4-chloro-a-(1-methylethyl)-, (R)-cyano(3-phenoxyphenyl)methyl ester, (aR)-
benzeneacetic acid, 4-chloro-a-(1-methylethyl)-, cyano (3-phenoxyphenyl)methyl ester, (S-(R*,R*))-
benzeneacetic acid, 4-chloro-a-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester, (S-(R*,R*))-
[(R)-
cyano-(3-phenoxyphenyl)methyl] (2R)-2-(4-chlorophenyl)-3-methylbutanoate
(R)-
cyano(3-phenoxyphenyl)methyl (2R)-2-(4-chlorophenyl)-3-methylbutanoate
fenvalerate (R,R)-isomer
fenvalerate A
sumiciclin A alpha
sumicidin A a
PubMed:
An enantioselective amidase from Burkholderia multivorans for the stereoselective synthesis of Esfenvalerate.
PubMed:
Environmentally relevant mixing ratios in cumulative assessments: A study of the kinetics of pyrethroids and their ester cleavage metabolites in blood and brain; and the effect of a pyrethroid mixture on the motor activity of rats.
PubMed:
Determination of five pyrethroids in tea drinks by dispersive solid phase extraction with polyaniline-coated magnetic particles.
PubMed:
Synergistic sub-lethal effects of a biocide mixture on the springtail Folsomia fimetaria.
PubMed:
Pyrethroids in house dust from the homes of farm worker families in the MICASA study.
PubMed:
Dietary intakes of pesticides based on community duplicate diet samples.
PubMed:
Crop pollination exposes honey bees to pesticides which alters their susceptibility to the gut pathogen Nosema ceranae.
PubMed:
Economic feasibility of methoprene applied as a surface treatment and as an aerosol alone and in combination with two other insecticides.
PubMed:
No proof of synergy at environmentally realistic concentrations of prochloraz and esfenvalerate--a reaction on "synergy in microcosms with environmentally realistic concentrations of prochloraz and esfenvalerate" by Bjergager et al. (Aquat. Toxicol. 101 (2011), 412-422).
PubMed:
Laboratory degradation rates of 11 pyrethroids under aerobic and anaerobic conditions.
PubMed:
Elevated temperature prolongs long-term effects of a pesticide on Daphnia spp. due to altered competition in zooplankton communities.
PubMed:
Susceptibility of stored-product psocids to aerosol insecticides.
PubMed:
Total effects of contact and residual exposure of bifenthrin and λ-cyhalothrin on the predatory mite Galendromus occidentalis (Acari: Phytoseiidae).
PubMed:
The toxicity of a ternary biocide mixture to two consecutive earthworm (Eisenia fetida) Generations.
PubMed:
The response of natural enemies to selective insecticides applied to soybean.
PubMed:
Impact of insecticide and fungicide residue contact on plum curculio, Conotrachelus nenuphar (Herbst), mobility and mortality: implications for pest management.
PubMed:
Two stressors and a community: effects of hydrological disturbance and a toxicant on freshwater zooplankton.
PubMed:
Esfenvalerate toxicity to the cladoceran Ceriodaphnia dubia in the presence of green algae, Pseudokirchneriella subcapitata.
PubMed:
Magnetic solid-phase extraction of five pyrethroids from environmental water samples followed by ultrafast liquid chromatography analysis.
PubMed:
Toxicity of thiamethoxam and mixtures of chlorantraniliprole plus acetamiprid, esfenvalerate, or thiamethoxam to neonates of oriental fruit moth (Lepidoptera: Tortricidae).
PubMed:
[Chemical toxicological identification of esfenvalerate].
PubMed:
Environmentally relevant mixtures in cumulative assessments: an acute study of toxicokinetics and effects on motor activity in rats exposed to a mixture of pyrethroids.
PubMed:
Identifying the cause of sediment toxicity in agricultural sediments: the role of pyrethroids and nine seldom-measured hydrophobic pesticides.
PubMed:
Pyrethroids in human breast milk: occurrence and nursing daily intake estimation.
PubMed:
Intraspecific competition increases toxicant effects in outdoor pond microcosms.
PubMed:
Baseline toxicity and field efficacy of metaflumizone on Colorado potato beetle (Coleoptera: Chrysomelidae).
PubMed:
Interspecific competition delays recovery of Daphnia spp. populations from pesticide stress.
PubMed:
Synergy between prochloraz and esfenvalerate in Daphnia magna from acute and subchronic exposures in the laboratory and microcosms.
PubMed:
Activation of a tunicate (Ciona intestinalis) xenobiotic receptor orthologue by both natural toxins and synthetic toxicants.
PubMed:
Photo-Fenton degradation of the insecticide esfenvalerate in aqueous medium using a recirculation flow-through UV photoreactor.
PubMed:
Insecticide resistance in bedbugs in Thailand and laboratory evaluation of insecticides for the control of Cimex hemipterus and Cimex lectularius (Hemiptera: Cimicidae).
PubMed:
An aphid-dip bioassay to evaluate susceptibility of soybean aphid (Hemiptera: Aphididae) to pyrethroid, organophosphate, and neonicotinoid insecticides.
PubMed:
Microencapsulated pear ester enhances insecticide efficacy in walnuts for codling moth (Lepidoptera: Tortricidae) and navel orangeworm (Lepidoptera: Pyralidae).
PubMed:
Susceptibility of oriental fruit moth (Lepidoptera: Tortricidae) to two pyrethroids and a proposed diagnostic dose of esfenvalerate for field detection of resistance.
PubMed:
Additivity of pyrethroid actions on sodium influx in cerebrocortical neurons in primary culture.
PubMed:
Environmental context determines community sensitivity of freshwater zooplankton to a pesticide.
PubMed:
Pesticides in house dust from urban and farmworker households in California: an observational measurement study.
PubMed:
The presence of flour affects the efficacy of aerosolized insecticides used to treat the red flour beetle, Tribolium castaneum.
PubMed:
Synergy in microcosms with environmentally realistic concentrations of prochloraz and esfenvalerate.
PubMed:
Activity of broad-spectrum and reduced-risk insecticides on various life stages of cranberry fruitworm (Lepidoptera: Pyralidae) in highbush blueberry.
PubMed:
Mechanisms of pyrethroid insecticide-induced stimulation of calcium influx in neocortical neurons.
PubMed:
Harvestman (Opiliones) fauna associated with Maine lowbush blueberry fields in the major production areas of Washington and Hancock counties.
PubMed:
Reducing tuber damage by potato tuberworm (Lepidoptera: Gelechiidae) with cultural practices and insecticides.
PubMed:
Pyrethroid insecticide concentrations and toxicity in streambed sediments and loads in surface waters of the San Joaquin Valley, California, USA.
PubMed:
Cross-resistance between azinphos-methyl and acetamiprid in populations of codling moth, Cydia pomonella (L.) (Lepidoptera: Tortricidae), from Washington State.
PubMed:
Dexamethasone transcriptionally increases the expression of the pregnane X receptor and synergistically enhances pyrethroid esfenvalerate in the induction of cytochrome P450 3A23.
PubMed:
Pesticide concentrations in water and sediment and associated invertebrate toxicity in Del Puerto and Orestimba Creeks, California, 2007-2008.
PubMed:
Targeting Cydia pomonella (L.) (Lepidoptera: Tortricidae) adults with low-volume applications of insecticides alone and in combination with sex pheromone.
PubMed:
A rapid and sensitive analytical method for the determination of 14 pyrethroids in water samples.
PubMed:
Linking mechanistic and behavioral responses to sublethal esfenvalerate exposure in the endangered delta smelt; Hypomesus transpacificus (Fam. Osmeridae).
PubMed:
Curative activity of insecticides on Rhagoletis pomonella (Diptera: Tephritidae) in apples.
PubMed:
Curative activity of insecticides against plum curculio (Coleoptera: Curculionidae) in tart cherries.
PubMed:
Evidence for a separate mechanism of toxicity for the Type I and the Type II pyrethroid insecticides.
PubMed:
Differential efficacy of three commonly used pyrethroids against laboratory and field-collected larvae and adults of Helicoverpa zea (Lepidoptera: Noctuidae) and significance for pyrethroid resistance management.
PubMed:
Comparative functional observational battery study of twelve commercial pyrethroid insecticides in male rats following acute oral exposure.
PubMed:
Flight activity of Sitophilus oryzae (L) and Sitophilus zeamais Motsch (Coleoptera: Curculionidae) and its relationship with susceptibility to insecticides.
PubMed:
Feeding cessation effects of chlorantraniliprole, a new anthranilic diamide insecticide, in comparison with several insecticides in distinct chemical classes and mode-of-action groups.
PubMed:
Development of an enzyme-linked immunosorbent assay for the alpha-cyano pyrethroids multiresidue in Tai lake water.
PubMed:
Method development for the analysis of organophosphate and pyrethroid insecticides at low parts per trillion levels in water.
PubMed:
Design of a compressed air modulator to be used in comprehensive multidimensional gas chromatography and its application in the determination of pesticide residues in grapes.
PubMed:
Resistance of Pakistani field populations of spotted bollworm Earias vittella (Lepidoptera: Noctuidae) to pyrethroid, organophosphorus and new chemical insecticides.
PubMed:
Survey for resistance to four insecticides in Myzus persicae clones from peach trees and weeds in south-central Washington.
PubMed:
Insecticide toxicity to Trichogramma pretiosum (Hymenoptera: Trichogrammatidae) females and effect on descendant generation.
PubMed:
The pyrethroid pesticide esfenvalerate suppresses the afternoon rise of luteinizing hormone and delays puberty in female rats.
PubMed:
The influence of predation on the chronic response of Artemia sp. populations to a toxicant.
PubMed:
Evaluation of management strategies for bean leaf beetles (Coleoptera: Chrysomelidae) and Bean pod mottle virus (Comoviridae) in soybean.
PubMed:
Measuring pyrethroids in sediment pore water using matrix-solid phase microextraction.
PubMed:
Expression of immune-regulatory genes in juvenile Chinook salmon following exposure to pesticides and infectious hematopoietic necrosis virus (IHNV).
PubMed:
Effects of dietary esfenvalerate exposures on three aquatic insect species representing different functional feeding groups.
PubMed:
Impact of aquatic insect life stage and emergence strategy on sensitivity to esfenvalerate exposure.
PubMed:
Clutch morphology and the timing of exposure impact the susceptibility of aquatic insect eggs to esfenvalerate.
PubMed:
Effects of neurotoxic insecticides on heat-shock proteins and cytokine transcription in Chinook salmon (Oncorhynchus tshawytscha).
PubMed:
Developmentally-regulated sodium channel subunits are differentially sensitive to alpha-cyano containing pyrethroids.
PubMed:
Neurotoxic implications of the agonistic action of CS-syndrome pyrethroids on the N-type Ca(v)2.2 calcium channel.
PubMed:
Acute, sublethal exposure to a pyrethroid insecticide alters behavior, growth, and predation risk in larvae of the fathead minnow (Pimephales promelas).
PubMed:
Extraction and analysis methods for the determination of pyrethroid insecticides in surface water, sediments and biological tissues at environmentally relevant concentrations.
PubMed:
Esfenvalerate-induced case-abandonment in the larvae of the caddisfly (Brachycentrus americanus).
PubMed:
Determination of 23 pesticide residues in leafy vegetables using gas chromatography-ion trap mass spectrometry and analyte protectants.
PubMed:
Identifying the cause and source of sediment toxicity in an agriculture-influenced creek.
PubMed:
Lethal and sublethal activities of imidacloprid contribute to control of adult Japanese beetle in blueberries.
PubMed:
Comparisons of tissue-specific transcription of stress response genes with whole animal endpoints of adverse effect in striped bass (Morone saxatilis) following treatment with copper and esfenvalerate.
PubMed:
Selection of a field population of diamondback moth (Lepidoptera: Plutellidae) with acetamiprid maintains, but does not increase, cross-resistance to pyrethroids.
PubMed:
Identification of rat and human cytochrome p450 isoforms and a rat serum esterase that metabolize the pyrethroid insecticides deltamethrin and esfenvalerate.
PubMed:
Pesticide and pathogen: heat shock protein expression and acetylcholinesterase inhibition in juvenile Chinook salmon in response to multiple stressors.
PubMed:
Toxicity of insecticides to the sweetpotato whitefly (Hemiptera: Aleyrodidae) and its natural enemies.
PubMed:
Hydrolysis of pyrethroids by human and rat tissues: examination of intestinal, liver and serum carboxylesterases.
PubMed:
Influence of emulsifiable concentrate formulation on the physical properties of the fluid, spray characteristics, and insecticide deposits on stored grains.
PubMed:
Toxicity of six pesticides to common frog (Rana temporaria) tadpoles.
PubMed:
Susceptibility of immature stages of Homalodisca coagulata (Hemiptera: Cicadellidae) to selected insecticides.
PubMed:
Species differences in the in vitro metabolism of deltamethrin and esfenvalerate: differential oxidative and hydrolytic metabolism by humans and rats.
PubMed:
Solid-phase sediment toxicity identification evaluation in an agricultural stream.
PubMed:
Is prochloraz a potent synergist across aquatic species? A study on bacteria, daphnia, algae and higher plants.
PubMed:
Establishment of baseline susceptibility data to various insecticides for Homalodisca coagulata (Homoptera: Cicadellidae) by comparative bioassay techniques.
PubMed:
Effects of hydrophilic and hydrophobic kaolin-based particle films on pea aphid (Homoptera: Aphididae) and its entomopathogen Pandora neoaphidis (Entomophthorales: Entomophthoraceae).
PubMed:
Development, oviposition, and mortality of Neoseiulus fallacis (Acari: Phytoseiidae) in response to reduced-risk insecticides.
PubMed:
Joint toxicity of chlorpyrifos and esfenvalerate to fathead minnows and midge larvae.
PubMed:
Metabolic effects of dinoseb, diazinon and esfenvalerate in eyed eggs and alevins of Chinook salmon (Oncorhynchus tshawytscha) determined by 1H NMR metabolomics.
PubMed:
Comparison of different mass spectrometric detection techniques in the gas chromatographic analysis of pyrethroid insecticide residues in soil after microwave-assisted extraction.
PubMed:
Relative potencies for acute effects of pyrethroids on motor function in rats.
PubMed:
Acute contamination with esfenvalerate and food limitation: chronic effects on the mayfly, Cloeon dipterum.
PubMed:
Residues and toxicity of esfenvalerate and permethrin in water and sediment, in tributaries of the Sacramento and San Joaquin rivers, California, USA.
PubMed:
Synergistic effects of esfenvalerate and infectious hematopoietic necrosis virus on juvenile chinook salmon mortality.
PubMed:
Individual variability in esterase activity and CYP1A levels in Chinook salmon (Oncorhynchus tshawytscha) exposed to esfenvalerate and chlorpyrifos.
PubMed:
Development of a stir-bar-sorptive extraction-liquid desorption-large-volume injection capillary gas chromatographic-mass spectrometric method for pyrethroid pesticides in water samples.
PubMed:
IPM-compatibility of foliar insecticides for citrus: indices derived from toxicity to beneficial insects from four orders.
PubMed:
Use and toxicity of pyrethroid pesticides in the Central Valley, California, USA.
PubMed:
Effects of the pyrethroid esfenvalerate on life-cycle traits and population dynamics of Chironomus riparius--importance of exposure scenario.
PubMed:
Effect of temperature on efficacy of insecticides to differential grasshopper (Orthoptera: Acrididae).
PubMed:
Toxicity of storm-water runoff after dormant spray application in a french prune orchard, Glenn County, California, USA: temporal patterns and the effect of ground covers.
PubMed:
Sublethal toxicity of orchard stormwater runoff in Sacramento splittail (Pogonichthys macrolepidotus) larvae.
PubMed:
Evaluating toxicity of Asana XL (esfenvalerate) amendments in agricultural ditch mesocosms.
PubMed:
Distribution and toxicity of sediment-associated pesticides in agriculture-dominated water bodies of California's Central Valley.
PubMed:
Molecular and cellular biomarker responses to pesticide exposure in juvenile chinook salmon (Oncorhynchus tshawytscha).
PubMed:
Contact and leaf residue activity of insecticides against the sweet Corn pest Euxesta stigmatias (Diptera: Otitidae).
PubMed:
Soil photolysis in a moisture- and temperature-controlled environment. 2. Insecticides.
PubMed:
Consequences of a short pulse of pesticide exposure for survival and reproduction of Gammarus pulex.
PubMed:
Innovative uses of vegetated drainage ditches for reducing agricultural runoff.
PubMed:
Structure-activity and interaction effects of 14 different pyrethroids on voltage-gated chloride ion channels.
PubMed:
Integrated management tactics for Frankliniella thrips (Thysanoptera: Thripidae) in field-grown pepper.
PubMed:
Economic injury levels and sequential sampling plans for Mexican bean beetle (Coleoptera: Coccinellidae) on dry beans.
PubMed:
Quantitative trait locus mapping of pyrethroid resistance in Colorado potato beetle, Leptinotarsa decemlineata (Say) (Coleoptera: Chrysomelidae).
PubMed:
Insecticide-resistant pollen beetles (Meligethes aeneus F) found in Danish oilseed rape (Brassica napus L) fields.
PubMed:
Fluorescence quenching competitive immunoassay in micro droplets.
PubMed:
Joint acute toxicity of esfenvalerate and diazinon to larval fathead minnows (Pimephales promelas).
PubMed:
Reverse quantitative structure-activity relationship for modelling the sorption of esfenvalerate to dissolved organic matter. A multivariate approach.
PubMed:
Chemistry and fate of fenvalerate and esfenvalerate.
PubMed:
Effects of dietary exposure to the pyrethroid pesticide esfenvalerate on medaka (Oryzias latipes).
PubMed:
Field-based evaluation of biopesticide impacts on native biodiversity: malagasy coleoptera and anti-locust entomopathogenic fungi.
PubMed:
Broad-spectrum insecticide resistance in obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae) from Michigan.
PubMed:
Physical and chemical properties of pyrethroids.
PubMed:
Lack of (anti-) androgenic or estrogenic effects of three pyrethroids (esfenvalerate, fenvalerate, and permethrin) in the Hershberger and uterotrophic assays.
PubMed:
Persistence and performance of esfenvalerate residues on broccoli.
PubMed:
Toxicity of stormwater runoff after dormant spray application of diazinon and esfenvalerate (Asana) in a French prune orchard, Glenn county, California, USA.
PubMed:
Sublethal effects of esfenvalerate residues on pyrethroid resistant Typhlodromus pyri (Acari: Phytoseiidae) and its prey Panonychus ulmi and Tetranychus urticae (Acari: Tetranychidae).
PubMed:
Fate and effects of esfenvalerate in agricultural ponds.
PubMed:
Probabilistic risk assessment of cotton pyrethroids: II. Aquatic mesocosm and field studies.
PubMed:
Spider fauna in apple ecosystem of western Oregon and its field susceptibility to chemical and microbial insecticides.
PubMed:
Reduction of azinphos-methyl, chlorpyrifos, esfenvalerate, and methomyl residues in processed apples.
PubMed:
Enzyme-linked immunosorbent assay for the pyrethroid permethrin.
PubMed:
Correlated insecticide cross-resistance in azinphosmethyl resistant codling moth (Lepidoptera: Tortricidae).
PubMed:
Potential for integrating eleven agricultural insecticides with the predatory bug Pristhesancus plagipennis (Hemiptera: Reduviidae).
PubMed:
Baseline susceptibility to imidacloprid and cross resistance patterns in Colorado potato beetle (Coleoptera: Chrysomelidae) populations.
PubMed:
Development of an immunoassay for the pyrethroid insecticide esfenvalerate.
PubMed:
An enzyme-linked immunosorbent assay for the detection of esfenvalerate metabolites in human urine.
PubMed:
Determination of pyrethroid pesticide residues in fatty materials by solid-matrix dispersion partition, followed by mini-column size-exclusion chromatography.
PubMed:
Pest status of American plum borer (Lepidoptera: Pyralidae) and fruit tree borer control with synthetic insecticides and entomopathogenic nematodes in New York State.
PubMed:
Indirect effects of esfenvalerate (insecticide) on the density of periphytic algae in artificial ponds.
PubMed:
Analytical method for the determination of urinary 3-phenoxybenzoic acid in subjects occupationally exposed to pyrethroid insecticides.
PubMed:
New method for analysis of pyrethroid insecticides: esfenvalerate, cis-permethrin, and trans-permethrin, in surface waters using solid-phase extraction and gas chromatography.
PubMed:
Selective extraction of pyrethroid pesticide residues from milk by solid-matrix dispersion.
PubMed:
Clean-up of aqueous acetone vegetable extracts by solid-matrix partition for pyrethroid residue determination by gas chromatography-electron-capture detection.
PubMed:
Virulence of the entomopathogenic fungus Metarhizium flavoviride Gams and Rozsypal and toxicity of diflubenzuron, fenitrothion-esfenvalerate and profenofos-cypermethrin to nontarget arthropods in Mauritania.
PubMed:
Effects of esfenvalerate on the reproductive success of the bluegill sunfish, Lepomis macrochirus in littoral enclosures.
PubMed:
Effect of algal food concentration on toxicity of two agricultural pesticides to Daphnia carinata.
PubMed:
Use of microcosm and fish toxicity data to select mesocosm treatment concentrations.
PubMed:
Effects of three synergists on pyrethroid resistance in the German cockroach (Dictyoptera: Blattellidae).
PubMed:
Acaricide susceptibility of immature Ixodes scapularis (Acari: Ixodidae) as determined by the disposable pipet method.
PubMed:
Effects of pyrethroid insecticides on gap junctional intercellular communications in Balb/c3T3 cells by dye-transfer assay.
PubMed:
Effects of fenvalerate and esfenvalerate on hepatic gap junctional intercellular communication in rats.
PubMed:
Effect of temperature on the toxicities of ten pyrethroids to German cockroach (Dictyoptera: Blattellidae).
PubMed:
Pyrethroid resistance and synergism in a field strain of the German cockroach (Dictyoptera: Blattellidae).
PubMed:
Deposition of esfenvalerate on Brassica vegetables.
PubMed:
Lack of enhancing effects of fenvalerate and esfenvalerate on induction of preneoplastic glutathione S-transferase placental form positive liver cell foci in rats.
PubMed:
[Evaluation of the sensitivity of adult Culex quinquefasciatus Say to chemical insecticides].