| esfenvalerate (Ref: OMS 3023) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for esfenvalerate
Description: A pyrethroid insecticide especially effective against Coleoptera, Diptera and Hemiptera
Example pests controlled: Aphids; BYDV vectors; Ticks; Fleas; Cucumber beetles; Carpenter ants; Cockroaches; Crickets; Earwigs; Millipedes; Silverfish; Sowbugs; Scorpions
Example applications: Potatoes; Peas & beans; Curcubits; Grassland; Cereals including wheat, barley; Ornamentals; Non-agricultural situations such as schools, industrial sites, public buildings
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 1979 & 1985, first reported; 1987, first marketed
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | United Kingdom/Portugal |
| Date inclusion expires | 31/12/2022 |
| EU Candidate for substitution (CfS) | Yes - two 'Persistent-Bioaccumulative-Toxic' criteria |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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Also used in: Australia, USA
Chemical structure:
| Isomerism | A mixture of four stereoisomers (S,S-; R,S-; S,R-; R,R-) |
| Chemical formula | C25H22ClNO3 |
| Canonical SMILES | CC(C)C(C1=CC=C(C=C1)Cl)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3 |
| Isomeric SMILES | CC(C)[C@@H](C1=CC=C(C=C1)Cl)C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3 |
| International Chemical Identifier key (InChIKey) | NYPJDWWKZLNGGM-RPWUZVMVSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m0/s1 |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |
| Substance group | Pyrethroid | |
| Minimum active substance purity | 830 g/kg | |
| Known relevant impurities | - | |
| Substance origin | Synthetic | |
| Mode of action | Contact and stomach action. Sodium channel modulator. | |
| CAS RN | 66230-04-4 | |
| EC number | - | |
| CIPAC number | 481 | |
| US EPA chemical code | 109303 | |
| PubChem CID | 10342051 | |
| Molecular mass (g mol-1) | 419.91 | |
| PIN (Preferred Identification Name) | (S)-cyano(3-phenoxyphenyl)methyl (2S)-2-(4-chlorophenyl)-3-methylbutanoate | |
| IUPAC name | (S)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate | |
| CAS name | (S)-cyano(3-phenoxyphenyl)methyl (αS)-4-chloro-α-(1-methylethyl)benzeneacetate | |
| Other status information | Severe Marine Pollutant | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | Not applicable | |
| Herbicide Resistance Classification (WSSA) | Not applicable | |
| Insecticide Resistance Classification (IRAC) | 3 | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Aphis gossypii Earias vittella Heliothis virescens Plutella xylostella Scirtothrips citri Blattella germanica many others |
|
| Physical state | Amber solid | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as an emulsifiable concentrate that is mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for esfenvalerate
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 0.001 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 26000 | A5 - n-Hexane | - | |
| 82000 | A5 - Methanol | - | ||
| 500000 | A5 - Acetone | - | ||
| Melting point (oC) | 59.1 | A5 | - | |
| Boiling point (oC) | 356 | A5 | - | |
| Degradation point (oC) | 356 | A5 - Decomposes on boiling | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 1.74 X 1006 | Calculated | - |
| Log P | 6.24 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.23 | A5 | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.17 X 10-09 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 4.92 X 10-04 | A5 | Non-volatile | |
GUS leaching potential index  |
-2.55 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 5.35 X 10-03 | Calculated | - |
| Note | Estimated concentrations of chemicals with Koc values greater than 9995 ml g-1 are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | Acid: 277nm=2242.6 Neutral: 277.1nm=2237 Basic: 223,6nm=31353, 305.3nm=1247.7 |
A5 | - | |
| Surface tension (mN m-1) | - | - | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 66.6 | A5 | Moderately persistent |
| DT50 (lab at 20oC) | 66.6 | A5 | Moderately persistent | |
| DT50 (field) | 19.2 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 249 | A5 | - | |
| DT90 (field) | 125.2 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier Lab studies DT50 range 36.5 - 198.7 days, DT90 range 90 - 439 days, Field studies DT50 range 0.3 - 38.8 days, DT90 range 31.3 - 259 days | |||
| Dissipation rate RL50 on plant matrix | Value | 2.0 | R4 | - |
| Note | Published literature RL50 range 1.0-3.5 days, 2 field crops, various matrices, n=3 | |||
| Dissipation rate RL50 on and in plant matrix | Value | - | - | - |
| Note | - | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 2 | A5 | Moderately fast |
| Note | DT50 10 days in natural sunlight and pure water, 6 days in artifical sunlight and sterilised water | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 428 | A5 | Very persistent |
| Note | pH4 stable, pH9 5.3 days | |||
| Water-sediment DT50 (days) | 56 | A5 | Moderately fast | |
| Water phase only DT50 (days) | 30 | A3 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 4075 | L3 | Non-mobile |
| Koc | 251717 | |||
| Notes and range | EU dossier Kd range 600-15500 mL/g, Koc range 85700 - 596200 mL/g | |||
| Freundlich | Kf | - | - | - |
| Kfoc | - | |||
| 1/n | - | |||
| Notes and range | - | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| (1RS)-2-amino-2-oxo-1-(3-phenoxyphenyl)ethyl (Ref: SD-47117) |
Soil | 0.320 | Major fraction, Relevant | |
| 3-phenoxybenzoic acid |
Soil | 0.271 | Major fraction; Relevant | |
| (2RS)-2-(4-chlorophenyl)-3-methylbutanoic acid |
Soil | 0.444 | Major fraction; Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| (2RS,3RS)-3-(4-chlorophenyl)-4-methyl-2-(3-phenoxyphenyl)pentanenitrile | Dec-Fen | Plant; Soil (photolysis); Surface water; Groundwater; Sediment-water systems | - | - |
| N-[(1RS)-1-(4-chlorophenyl)-2-methylpropyl]-2-(3-phenoxyphenyl)acetamid | PA-fen | Sediment-water systems | - | - |
| 3-phenoxybenzaldehyde | PBald | Water (hydrolysis) | - | - |
| 2-(4-chlorophenyl)-3-methylbutanamide | CPIA-carboxamide | Water (hydrolysis) | - | - |
ECOTOXICOLOGY
for esfenvalerate
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 3250 | A5 | Threshold for concern |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 88.5 | A5 Rat | High | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 5.0 | A5 Rat | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | 1312 | A5 Colinus virginianus | Moderate | |
| Birds - Short term dietary (LC50/LD50) | > 5000 ppm | A4 Colinus virginianus, as fenvalerate | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 0.0001 | A4 Unknown species | High | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.00025 | A5 Oncorhynchus mykiss | High | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 0.00027 | A5 Daphnia magna | High | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.000052 | A5 Daphnia magna | High | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | 0.00013 | F4 Chironomus riparius | High | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.16 | A5 Chironomus riparius | Moderate | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.0065 | A5 Pseudokirchneriella subcapitata | High | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | 0.06 | A5 | High |
| Oral acute 48 hour LD50 (μg bee-1) | 0.21 | A4 | High | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 10.6 | A5 | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 10 | Mortality Dose: 0.0125 kg ha-1 A5 Chrysoperla carnea, larvae |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 90.7 | Mortality and Reproduction Dose: 0.15 g ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Dehydrogenase activity: Acceptable risk |
A5 Dose: 1.28 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | 0.00008 | A5 Fish and aquatic invertebrates | - |
| NOEAEC mg l-1 | 0.00025 | A3 Fish (NOEC) | - | |
HUMAN HEALTH AND PROTECTION
for esfenvalerate
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | 88.5 | A5 Rat | High | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 0.48 | A5 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.0175 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.0175 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.011 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 3-13% | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Minimal risk from dietary exposure Risk assessment indicates ARfD would not normally be execeeded |
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| Occupational | PPE/PPC required | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Highly toxic Some studies point to endocrine effects May cause nausea, vomiting and abdominal pain if ingested |
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: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
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| General |
IMDG Transport Code is usually 9 Not explosive or oxidising Flammable |
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| CLP classification 2013 | Health: H301, H317, H331, Environment: H400, H410 | |||
| EC Risk Classification |
T - Toxic: R23/25 Xn - Harmful: R43 H - handling risks: R10 N - Dangerous for the environment: R50, R53 |
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| EC Safety Classification |
S1/2, S24, S36/37/39, S45, S60, S61 | |||
| WHO Classification | II | - | Moderately hazardous | |
| US EPA Classification (formulation) | II | - | Warning - Moderately toxic | |
| UN Number | 3349 for active, variable with product, usually 1993 or 3351 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for esfenvalerate
| Language | Name |
| English | esfenvalerate |
| French | esfenvalerate |
| German | Esfenvalerat |
| Danish | esfenvalerat |
| Italian | esfenvalerate |
| Spanish | esfenvalerato |
| Greek | esfenvalerate |
| Slovenian | esfenvalerat |
| Polish | esfenwalerat |
| Swedish | esfenvalerat |
| Hungarian | eszfenualerat |
| Dutch | esfenvaleraat |
Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk
© University of Hertfordshire