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Permethrin (Ref: OMS 1821)
(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
                 
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
                 
Additional information
Also used in
Australia, USA
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
Pesticide type
Insecticide, Veterinary substance
Substance groups
Pyrethroid insecticide; Pyrethroid ester insecticide
Minimum active substance purity
>=90%
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
CLP index number
613-058-00-2
Molecular mass
391.29
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)
3A
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
  • BOC Sciences
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)
0.011
E4 E = Manufacturers safety data sheets
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
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
Boiling point (°C)
465.9
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
Degradation point (°C)
- - -
Flashpoint (°C)
159.4
E4 E = Manufacturers safety data sheets
4 = Verified data
 -
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. Available online but no longer updated. (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
Regulatory data - 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)
1.19
E3 E = Manufacturers safety data sheets
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. Dataset is no longer available.
4 = Verified data
 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)
13
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
13
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Non-persistent
DT₅₀ (field)
42
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
 Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
Dissipation rate RL₅₀ on plant matrix
Value
6.7
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
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
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
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
1
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
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; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Moderately persistent
Note
-
Water-sediment DT₅₀ (days)
40
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Moderately fast
Water phase only DT₅₀ (days)
23
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
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. Available online but no longer updated. (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
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
P4 P = Other non-EU, UK or US 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. Available online but no longer updated. (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. Available online but no longer updated. (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 data from online sources
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 / FAO data, IPCS INCHEM data (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 / FAO data, IPCS INCHEM data (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
Bombus 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 bee species (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 bee species (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 data from online sources
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. Available online but no longer updated. (click here )
4 = Verified data
Oncorhynchus mykiss		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.000093
P3 P = Other non-EU, UK or US 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 / FAO data, IPCS INCHEM data (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 / FAO data, IPCS INCHEM data (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; these datasets no longer available). Norman Ecotoxicology database. (click here )
3 = Unverified data of known source
Unknown species		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
0.0009
Q2 Q = Miscellaneous data from online sources
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. Available online but no longer updated. (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 / FAO data, IPCS INCHEM data (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; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Mouse		 -
Intravenous LD₅₀ = 31.0 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Mouse		 -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
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
B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
5 = Verified data used for regulatory purposes
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
Q3 Q = Miscellaneous data from online sources
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 Hazard Class 6.1
CLP classification 2013
Health: H302, H332, H335
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
UN3077
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
Chemically stable under standard ambient conditions. Shelf-life of 2 yrs. Store -20 DegC in an inert atmosphere
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
Norwegian
-
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