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Cis-permethrin (Ref: FMC 35171)
Last updated: 08/02/2024
(Also known as: NRDC 148; NRDC 167; cis-permethrin)
SUMMARY
Cis-permethrin is an obsolete insecticide. It has not been extensively studied and so very little data for environmental fate, ecotoxiocity of adverse human health concerns are available.
GENERAL INFORMATION
Description
A single stero-isomer pyrethroid insecticide usually used as the isomer mix
Availability status
Considered obsolete but may be available in some countries
Introduction & key dates
circa 1973, introduced
Examples of veterinary uses
Cis-permethrin has been used for the control of sweet itch on horses. As the stereo-isomer mix (permethrin) is was also used in livestock housing for insect pest control and for flea and tick control domestic pet
Examples of species treated
Dogs; Cats
Approval status
VMR 2013/2033 approval status (GB/UK)
Approved (as permethrin)
EU Regulatory approval status
Approved (as permethrin)
Chemical structure
Isomerism
Isomeric
Chemical formula
C₂₁H₂₀Cl₂O₃
Canonical SMILES
CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
Isomeric SMILES
CC1([C@@H]([C@@H]1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
International Chemical Identifier key (InChIKey)
RLLPVAHGXHCWKJ-IEBWSBKVSA-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
cis-permethrin -
General status
Veterinary substance type
Insecticide
Substance groups
Pyrethroid 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, Inhibitor], [Estrogen receptor alpha], [Nuclear receptor subfamily 1 group I member 2]
CAS RN
54774-46-8
Alternative/old CAS RN
52341-33-0; 54774-45-7; 54774-46-8
EC number
263-364-3
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
40463
CLP index number
No data found
Therapeutic Class
Antiparasitic products, insecticides & repellents: Pyrethrins & pyrethoids
ATCvet Code
QP53AC04
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
391.31
PIN (Preferred Identification Name)
3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
IUPAC name
3-phenoxybenzyl (1RS)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
CAS name
rel-(1R,3R)-(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Colourless crustalline solid
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Advantix Spot-on Solution (permethrin) Elanco Europe Ltd GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Armitage Pet Care Felt Flea Collar (permethrin) Sinclair Animal and Household Care Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM-GSL)
Ataxxa Spot-On Solution (permethrin) Krda d.d. Novo Mesto GB National authorisation Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details
Supplied in a range of formulations including flea collars, spot-on and pour-on products
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
- - -
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
- - -
Boiling point (°C)
465.9
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
159.4
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
- - -
Log P
- - -
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.293
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
- - -
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
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)
- - -
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
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)
- - -
-
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)
- - -
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.001
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Danio rerio 7 day		 High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
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)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
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)
- - -
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
- - -
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
-
Mammalian dose elimination route and rate
Permethrin and its metabolites are excreted primarily in the urine with some in the faeces
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
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
;
E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results
✓Yes, known to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
 No data found
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
✓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
A poison by intravenous & intraperitoneal routes
Inhalation may produce nausea, vomiting, sneezing & serious nasal problems
High dose may cause hyperexcitability, incoordination, tremors, muscular paralysis & lead to death
US EPA - substance is a weak carcinogen
Handling issues
Property
Value and interpretation
General
IMDG Transport Hazard Class 9
CLP classification 2013
-
WHO Classification
II (Moderately hazardous)
UN Number
UN3077
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
cis-permethrin
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 08/02/2024
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