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Tetrachlorvinphos (Ref: SD 8447)
Last updated: 22/08/2024
(Also known as: stirofos; CVMP)
GENERAL INFORMATION
Description
Av organophosphorus insecticide used for the control of ectoparasites
Availability status
Current
Introduction & key dates
1967, registered USA
Examples of veterinary uses
Use to control ticks, flies and mites
Examples of species treated
Cats; Dogs; Cattle; Pigs; Horses
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
Isomeric - exists in both the Z- and E- forms. Technical products are predominately comprised of the Z-stereoisomer.
Chemical formula
C₁₀H₉Cl₄O₄P
Canonical SMILES
COP(=O)(OC)OC(=CCl)C1=CC(=C(C=C1Cl)Cl)Cl
Isomeric SMILES
COP(=O)(OC)O/C(=C\Cl)/C1=CC(=C(C=C1Cl)Cl)Cl
International Chemical Identifier key (InChIKey)
UBCKGWBNUIFUST-YHYXMXQVSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H9Cl4O4P/c1-16-19(15,17-2)18-10(5-11)6-3-8(13)9(14)4-7(6)12/h3-5H,1-2H3/b10-5+
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
tetrachlorvinphos Unstated isomer
General status
Veterinary substance type
Insecticide, Antiparasitic
Substance groups
Organophosphate insecticide; Organophosphate acaricide; Organothiophosphate insecticide; Organothiophosphate acaricide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Acetylcholinesterase (AchE) inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
22248-79-9
EC number
213-506-3
CIPAC number
265
US EPA chemical code
083701 (Z) / 083702 (E)
PubChem CID
5284462
CLP index number
No data found
Therapeutic Class
Antiparasitic products, insecticides & repellents: Ectoparasiticides
ATCvet Code
QP53AF14
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
365.96
PIN (Preferred Identification Name)
(1Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl phosphate
IUPAC name
(Z)-2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate
CAS name
(1Z)-2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl phosphate
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Off-white crsytalline solid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
Available in a wide variety of formulations including pet flea & tick collars, shampoos, dusts, powders and aerosol/pump sprays for direct treatment of pets and pet sleeping areas. Also used for antiparastic cattle eartags.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
11.6
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
94
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
3.39 X 1003 Calculated -
Log P
3.53
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.52
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
0.0056
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.86 X 10-04
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-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
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
2
M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Best available data
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.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
H3 H = The US ARS pesticide properties database. Dataset is no longer available.
3 = Unverified data of known source
 Slightly mobile
Koc (mL g⁻¹)
900
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
0.31 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
desmethyltetrachlorvinphos
- - -
2,4,5-trichloroacetophenone
- - Aerobic
1-(2,4,5-trichloropheynl)ethanol
- - Aerobic
1-(2,4,5-trichlorophenyl)-2-chloroethan-1-ol
- - Aerobic
2-chloro-1-(2,4,5-trichlorophenyl)ethanol
- - Aerobic
1-(2,4,5-trichlorophenyl)ethan-1-ol
- - Aerobic
2,4,5-trichlorobenzoic acid
- - Aerobic
Known groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
desmethyltetrachlorvinphos - Rat (Urine) -
2,4,5-trichloroacetophenone - Plant -
1-(2,4,5-trichlorophenyl)-2-chloroethan-1-ol - Plant -
2-chloro-1-(2,4,5-trichlorophenyl)ethanol - Plant -
dimethyl phosphate - Rats (Urine) -
monomethyl phosphate - Rats (Urine) -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4000
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)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr		 -
(ppm diet)
125 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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)
- - -
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)
> 1.37
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
Apis mellifera		 Moderate
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)
> 0.43
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
Oncorhynchus mykiss		 Moderate
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)
0.002
J4 J = Pesticide Action Network database (click here )
4 = Verified data
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)
- - -
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
- - -
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)
> 4000
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)
1500
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.85
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ > 5000 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Guinea pig		 -
Subcutaneous LD₅₀ > 5000 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rabbit		 -
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
List I; List II - -
Exposure Routes
Public
-
Occupational
May be absorbed through the skin
Mammalian dose elimination route and rate
Metabolised and mainly excreted 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
?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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
✓Yes, known to cause a problem
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
?Possibly, status not identified
 No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
IARC Group 2B carcinogen; US EPA - likely to be human carcinogen
Kidney and liver toxicant
Suspected of causing genetic defects
Repeated or prolonged skin contact may cause allergic reactions with susceptible person
Handling issues
Property
Value and interpretation
General
IMDG Transport Hazard Class 6.1
Highly flammable
CLP classification 2013
Health: H302, H312, H332, H341
Environment: H400, H410
WHO Classification
III (Slightly hazardous)
UN Number
UN3018
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
tetrachlorvinphos
French
tétrachlorvinphos
German
Tetrachlorvinphos
Danish
tetrachlorvinphos
Italian
tetraclorvinfos
Spanish
tetraclorvinfos
Greek
-
Polish
tetrachlorwinfos
Swedish
-
Hungarian
-
Dutch
tetrachloorvinvos
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