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esfenvalerate (Ref: OMS 3023)
** fenvalerate-U ** DPX YB656 ** S-5602-alpha ** Translations

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GENERAL INFORMATION Click here for an explantaion of the general chemical status 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: Click to access a note on the approvals information on this site

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

Also used in: Australia, USA

Chemical structure: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
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 Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • BASF
  • Greencrop
  • Standon
Example products using this active
  • Sumi-Alpha
  • Hounddog
  • Sven
  • Asana
  • Esfenvalerate 5EC
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 Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
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 Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index 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 Click here for a note on the limitations of the 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 Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
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 Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
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 Click here for further information on 1107/2009 relevancy
(1RS)-2-amino-2-oxo-1-(3-phenoxyphenyl)ethyl (Ref: SD-47117) This metabolite may cause environmental pollution, click here for further information Soil   0.320   Major fraction, Relevant
3-phenoxybenzoic acid This metabolite may cause environmental pollution, click here for further information Soil   0.271   Major fraction; Relevant
(2RS)-2-(4-chlorophenyl)-3-methylbutanoic acid This metabolite may cause environmental pollution, click here for further information 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 Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
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 Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the 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
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

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Highly toxic
Some studies point to endocrine effects
May cause nausea, vomiting and abdominal pain if ingested

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes IMDG Transport Code is usually 9
Not explosive or oxidising
Flammable
CLP classification 2013 Health: H301, H317, H331, Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases T - Toxic: R23/25
Xn - Harmful: R43
H - handling risks: R10
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases 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 Click here for a description of UN packaging marks 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
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