Permethrin (Ref: OMS 1821)

Permethrin (Ref: OMS 1821)	Last updated: 14/05/2022
(Also known as: permethrine)

SUMMARY

Permethrin is a contact insecticide. It is not highly soluble in water, has a low volatility and is not normally expected to leach to groundwater. It would also not be expected to persist in soil or water systems. It is moderately toxic to humans, is an irritant and may be a CNS toxicant. It is highly toxic to most aquatic species and honey bees but is not highly toxic to birds or earthworms.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Moderately persistent; Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Carcinogen; Endocrine distrupter; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide active against a wide range of pests including Lepidoptera and Coleoptera in crops and various animal ectoparasites

Example pests controlled

Cockroaches; Termites; Ticks; Mosquitoes; Aphids; Fleas; Ants

Example applications

Fruit; Vegetables; Cotton; Ornamentals; Potatoes; Cereals

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1973

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Ireland

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU 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

Additional information

Also used in

Australia, USA

Chemical structure

Isomerism

A chiral molecule

Chemical formula

C₂₁H₂₀Cl₂O₃

Canonical SMILES

CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

RLLPVAHGXHCWKJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3/t17-,19-/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
cispermethrin	Cis-isomer
transpermethrin	Trans-isomer

General status

Pesticide type

Insecticide, Veterinary substance

Substance groups

Pyrethroid insecticide; Pyrethroid ester insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Broad spectrum with contact and stomach action. Slight repellant effect. Sodium channel modulator.

CAS RN

52645-53-1

EC number

258-067-9

CIPAC number

331

US EPA chemical code

109701

PubChem CID

40326

Molecular mass

391.3

PIN (Preferred Identification Name)

IUPAC name

3-phenoxybenzyl (1RS,3RS;1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

CAS name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

Other status information

Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

UK statutory standard for the protection of aquatic life: freshwater and saltwater: 0.01 µg l⁻¹

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

Aedes aegypti, Bemisia tabaci, Chrysoperla carnea, Culex pipiens pipiens, Diadegma insulare, Helicoverpa zea, many others

Physical state

Colourless crystalline solid to brown viscous liquid depending upon purity

Formulations

Property

Value

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

Agropharm
ICI Plant Protection
Mitchell Cotts
FMC

Example products using this active

Fortefog P Fumer
Ambush
Exmin
Kestril
Ectiban
Pynosect
Corsair
Arctic

Formulation and application details

Available in a variety of formulations including fumigants, shampoos and spot-on treatments

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.2

Low

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

1000000

Hexane

258000

Methanol

1000000

Xylene

Melting point (°C)

34.5

Boiling point (°C)

200

Degradation point (°C)

Flashpoint (°C)

100

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

1.26 X 10⁰⁶

Calculated

Log P

6.1

High

Density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.007

at 25°C

Low volatility

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

1.89 X 10^-01

Moderately volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ on plant matrix

Value

6.7

Note

Published literature RL₅₀ range 2.5-20.0 days, 8 field & undercover grown crops, various matrices, n=9

Dissipation rate RL₅₀ on and in plant matrix

Value

11.1

Note

Published literature RL₅₀ range 9.5-13.9 days, 3 field & undercover grown crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Moderately persistent

Note

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

100000

Notes and range

Freundlich

K_f

1.87

K_foc

¹/_n

0.99

Notes and range

Soil with 68% loam, 24% silt, 8% clay, pH 6.5, OC=2.1%

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.62

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

300

(Other literature Log BCF range 1.4-3.3 (R3))

Threshold for concern

CT₅₀ (days)

Not available

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 430

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

100

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 9800

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

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

1440

Low

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

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

0.024

Apis mellifera

High

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

0.13

Apis mellifera

High

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

Chronic

Bumblebees (Bombus spp.)

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

> 0.22

Bomus terrestris

High

Literature DT₅₀ values range 0.22-0.82 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)

0.0157

Megachile rotundata

High

Mode of exposure

Contact

Other pollinators (2)

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

0.07

Trigona spinipes

High

Mode of exposure

Contact

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Harmful

Parasitic wasp

Beneficial insects (Predatory mites)

Harmful

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0125

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000093

Anabas testudineus

High

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

0.0006

Daphnia magna

High

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

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

0.00002

Americamysis bahia

High

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

0.0029

Chironomus riparius

High

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

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.0125

Unknown species

Moderate

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

0.0009

Unknown species

High

Mesocosm study data

NOEAEC mg l⁻¹

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)

> 430

Rat

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.685

Rat

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 429 mg kg⁻¹

Mouse

Intravenous LD₅₀ = 31.0 mg kg⁻¹

Mouse

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

0.05

JMPR 1999

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

1.5

JMPR 2003

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Non-statutory WHO drinking water guideline 0.3 mg l⁻¹

UK EA QS database 2018

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Rapidly metabolised by ester hydrolysis to inactive metabolites which are excreted primarily in the urine

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

Harmful
Estrogenic
IARC Group 3 carcinogen; USEPA - probable human carcinogen
Endocrine issues - Inhibition of estrogen-sensitive cells proliferation

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H302, H332, H335
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

3352 for active, products usually 1230

Waste disposal & packaging

Packaging Group III (medium danger)

TRANSLATIONS

Language

Name

English

permethrin

French

permethrine

German

Permethrin

Danish

permethrin

Italian

permetrina

Spanish

permetrin

Greek

permethrin

Polish

permetryna

Swedish

permetrin

Hungarian

permetrin

Dutch

permethrin

Record last updated:	14/05/2022
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