Esfenvalerate (Ref: OMS 3023)

Esfenvalerate (Ref: OMS 3023)	Last updated: 04/11/2019
(Also known as: fenvalerate-U; DPX YB656; S-5602-alpha)

GENERAL INFORMATION

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

UK regulatory status

UK approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 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 EU-27 Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece
✓	✓	✓	✓	✓	✓			✓
ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg
✓	✓	✓	✓	✓	✓	✓		✓
LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia
		✓	✓	✓	✓	✓		✓

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⁻¹

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

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)

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

xylene

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Sumi-Alpha
Hounddog
Sven
Asana
Esfenvalerate 5EC

Example products using this active

BASF
Greencrop
Standon

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

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

0.001

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

26000

n-Hexane

82000

Methanol

500000

Acetone

Melting point (°C)

59.1

Boiling point (°C)

356

Degradation point (°C)

356

Decomposes on boiling

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

1.74 X 10⁰⁶

Calculated

Log P

6.24

High

Bulk density (g ml⁻¹)

1.23

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.17 X 10^-09

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

4.92 X 10^-04

Non-volatile

GUS leaching potential index

-1.80

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

High

Calculated

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

66.6

Moderately persistent

DT₅₀ (lab at 20 °C)

66.6

Moderately persistent

DT₅₀ (field)

19.2

Non-persistent

DT₉₀ (lab at 20 °C)

249

Persistent

DT₉₀ (field)

125.2

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

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

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 20 °C and pH 7

Value

428

Very persistent

Note

pH4 stable, pH9 5.3 days

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

4075

Non-mobile

K_oc

251717

Notes and range

EU dossier K_d range 600-15500 mL g⁻¹, K_oc range 85700 - 596200 mL g⁻¹

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

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

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

3250

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

88.5

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

5.0

Rat

High

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

1312

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 ppm

Colinus virginianus as fenvalerate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0001

Unknown species

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00025

Oncorhynchus mykiss

High

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.00027

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.000052

Daphnia magna

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00013

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.16

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

Pseudokirchneriella subcapitata

High

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.06

High

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.21

High

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

10.6

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

0.4

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 0.0125 kg ha⁻¹]
Chrysoperla carnea larvae

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

90.7

Mortality and Reproduction [Dose: 0.15 g ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Dehydrogenase activity: Acceptable risk

Dose: 1.28 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

0.00008

Fish and aquatic invertebrates

NOEAEC mg l⁻¹

0.00025

Fish (NOEC)

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

88.5

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.48

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.0175

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.0175

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.011

Rat SF=100

Dermal penetration studies (%)

3-13%

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

PPE/PPC required

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

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

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9
Not explosive or oxidising
Flammable

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

EC Safety Classification

S1/2, S24, S36/37/39, S45, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

3349 for active, variable with product, usually 1993 or 3351

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

esfenvalerate

French

esfenvalerate

German

Esfenvalerat

Danish

esfenvalerat

Italian

esfenvalerate

Spanish

esfenvalerato

Greek

esfenvalerate

Polish

esfenwalerat

Swedish

esfenvalerat

Hungarian

eszfenualerat

Dutch

esfenvaleraat

Record last updated:	04/11/2019
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242