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Permethrin (Ref: OMS 1821)
Last updated: 19/01/2023
(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
Used to control ectoparasites on domestic pets and other animals
Availability status
Current
Introduction & key dates
circa 1973
Examples of species treated
Cats, Dogs
Chemical structure
Isomerism
Permethrin is a chiral molecule presenting two forms, the cis and the trans isomers.
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
Veterinary substance type
Insecticide, Antiparasitic
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.
Molecular targets
[Sodium channel protein type 1 subunit alpha, blocker]
CAS RN
52645-53-1
EC number
258-067-9
CIPAC number
331
US EPA chemical code
109701
PubChem CID
40326
CLP index number
613-058-00-2
ATCvet Code
QP53AC04
Therapeutic Class
Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: Bovine)
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
Physical state
Colourless crystalline solid to brown viscous liquid depending upon purity
Formulations
Property
Product
Manufacturer
Authorisation Route
UK Legal Class
Example products using this active
Armatage Pet Care Felt Flea Collar Sinclair Animal & Household Care Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Beaphar Soft Cat Flea Collar Sinclair Animal and Household Care Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Defendog Cutaneous Spray Virbac S.A. UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Advantix Spot-on solution for dogs over 10 up to 25kg Bayer Ltd EU Mutually recognised procedure Prescription only medicine to be authorised by a veterinarian (POM-V)
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
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
1000000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane		 -
258000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
1000000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene		 -
Melting point (°C)
34.5
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
 -
Boiling point (°C)
200
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
100
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.26 X 1006 Calculated -
Log P
6.1
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
 High
Fat solubility of residues
Solubility
Soluble
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Data type
Observed in metabolism and farm animal feeding studies
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Density (g ml⁻¹)
1.29
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
0.007
R4 R = Peer reviewed scientific publications
4 = Verified data
at 25°C		 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.89 X 10-01
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
 Moderately volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
13
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
13
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Non-persistent
DT₅₀ (field)
42
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
 Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
1
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Moderately fast
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
31
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Moderately persistent
Note
-
Water-sediment DT₅₀ (days)
40
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Moderately fast
Water phase only DT₅₀ (days)
23
K4 K = Research datasets, e.g. Pandora, Demetra
4 = Verified data
 Slow
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
 Non-mobile
Koc
100000
Notes and range
-
Freundlich
Kf
1.87
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
Kfoc
-
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
Bio-concentration factor
BCF (l kg⁻¹)
300
P4 P = Other governments and regulators
4 = Verified data
(Other literature Log BCF range 1.4-3.3 (R3))		 Threshold for concern
CT₅₀ (days)
Not available -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 430
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 year		 -
(ppm diet)
100 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 9800
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
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
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
 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
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Apis mellifera		 High
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.13
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
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
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
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
R4 R = Peer reviewed scientific publications
4 = Verified data
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
R4 R = Peer reviewed scientific publications
4 = Verified data
Trigona spinipes		 High
Mode of exposure
Contact
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
Harmful
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
Parasitic wasp		 -
Beneficial insects (Predatory mites)
Harmful
AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
2 = Unverified data of unknown source
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
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
Oncorhynchus mykiss		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.000093
P3 P = Other governments and regulators
3 = Unverified data of known source
Anabas testudineus		 High
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.0006
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Daphnia magna		 High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
0.00002
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Americamysis bahia		 High
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
0.0029
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
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
K3 K = Research datasets, e.g. Pandora, Demetra
3 = Unverified data of known source
Unknown species		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
0.0009
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
Unknown species		 High
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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
G4 G = Extension Toxicology network database EXTOXNET (click here )
4 = Verified data
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rabbit		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 0.685
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ = 429 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Mouse		 -
Intravenous LD₅₀ = 31.0 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Mouse		 -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.05
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
JMPR 1999		 -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
1.5
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
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
-
Mammalian dose elimination route and rate
Rapidly metabolised by ester hydrolysis to inactive metabolites which are excreted primarily in the urine
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
✓Yes, known to cause a problem
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
✓Yes, known to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
?Possibly, status not identified
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
✓Yes, known to cause a problem
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 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: 19/01/2023
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