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Phenothrin (Ref: OMS 1809)
Last updated: 22/08/2024
(Also known as: ENT 27972; phenoxythrin; cyfenothrin; phenothrine; delta-(cis-trans)-phenothrin; R-phenothrin)
GENERAL INFORMATION
Description
A synthetic pyrethroid insecticide for parasite control
Availability status
Current
Introduction & key dates
1976, registered Japan
Examples of veterinary uses
Used to eradicate adult ticks, lice, mites and fleas
Examples of species treated
Dogs; Cats
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
Phenothrin is a molecule with two chiral centres. The technical material is an isomeric mixture of four isomers (1R- cis, 1R- trans, 1S- cis, 1S- trans)
Chemical formula
C₂₃H₂₆O₃
Canonical SMILES
CC(=CC1C(C1(C)C)C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
SBNFWQZLDJGRLK-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C23H26O3/c1-16(2)13-20-21(23(20,3)4)22(24)25-15-17-9-8-12-19(14-17)26-18-10-6-5-7-11-18/h5-14,20-21H,15H2,1-4H3
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Ectoparasiticide
Substance groups
Pyrethroid insecticide; Pyrethroid ester insecticide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic with rapid contact and stomach action. Sodium channel modulator. Blocks nerve impulse transmission.
Molecular targets
[Voltage-dependent sodium channel, Blocker]
CAS RN
26002-80-2
Alternative/old CAS RN
188023-86-1
EC number
247-404-5
CIPAC number
356
US EPA chemical code
069005
PubChem CID
4767
CLP index number
No data found
Therapeutic Class
Antiparasitic products, insecticides & repellents: Pyrethrins & pyrethroids
ATCvet Code
QP53AC03
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
350.46
PIN (Preferred Identification Name)
(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
IUPAC name
(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
CAS name
(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other status information
Marine Pollutant
Relevant Environmental Water Quality Standards
-
Physical state
Yellow to brown coloured liquid with a faint characteristic odour
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.0097
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
at 25 °C		 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
5000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Xylene		 -
5000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Acetone		 -
4960
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Hexane		 -
Melting point (°C)
- - -
Boiling point (°C)
290
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
107
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
(closed cup)		 -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.02 X 1006 Calculated -
Log P
6.01
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 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)
1.06
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)
0.021
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)
6.75 X 10-01
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderately volatile
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
1.548
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
35
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Best available literature data gives soil half life between 14 and 60 days
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)
- - -
Sediment 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.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Non-mobile
Koc (mL g⁻¹)
180000
Notes and range
-
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
-1.94 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
730
J4 J = Pesticide Action Network database (click here )
4 = Verified data
Cyprinidae		 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)
> 5000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Low
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)
> 2500
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Colinus virginianus		 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)
- - -
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)
0.13
K3 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
3 = Unverified data of known source
Apis mellifera		 High
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.16
K3 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
3 = Unverified data of known source
Apis mellifera		 High
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Chronic
- - -
Notes
[The residual time to 25% mortality (RT25) value for honeybees is 3 hrs - USEPA data]
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)
> 0.0027
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss		 High
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)
> 0.0043
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna		 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)
> 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)
- - -
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 (free-floating, growth) - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Aquatic plants (rooted, growth) - Acute 14 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
- - -
Marine bivalves
- - -
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)
> 5000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
2.1
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.07
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
 -
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
Excreted mainly as metabolites in urine but a proportion is excreted unchanged in faeces
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B1 B = DNA damage/repair (EFSA database)
1 = Positive
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E1 E = Unspecified genotoxicity type (miscellaneous data source)
1 = Positive
✓Yes, known to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
✓Yes, known to cause a problem
✓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
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion
May cause dizziness, headaches, fatigue and diarrhoea
Endocrine issues - Increase of estrogen-sensitive cells proliferation
Possible liver toxicant
One reported study suggests links with breast cancer
Handling issues
Property
Value and interpretation
General
Prevent generation of mists
Non-corrosive
Will generate acrid smoke and gases if heated to decomposition
Combustable
IMDG Transport Hazard Class 6.1
CLP classification 2013
Health: H302, H312, H332
Environment: H400, H410
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
UN3352
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
phenothrin
French
phenothrine
German
Phenothrin
Danish
phenothrin
Italian
fenotrin
Spanish
fenotrina
Greek
-
Polish
fenotryna
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 22/08/2024
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