Chlorfenvinphos (Ref: OMS 166)	Last updated: 23/08/2024
(Also known as: clofenvinfos; CVP; OMS 1328; ENT 24969; CGA 26351)

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SUMMARY

Chlorfenvinphos is a soil-applied insecticide. It has a moderate aqueous solubility and is miscible with many organic solvents. It is relatively volatile and there is some risk that it may leach to groundwater. It is moderately persistent in soil systems. It is highly toxic to mammals, an endocrine disrupter, a neurotoxin and an inhibitor of cholinesterase. In addition, there is some concern that it may bio-concentrate. Chlorfenvinphos is highly toxic to birds, honeybees and aquatic invertebrates. It is moderately toxic to fish and earthworms.

GENERAL INFORMATION

Description	An organophosphate antiparasitic used in veterinary medicine for external parasites
Availability status	Current
Introduction & key dates	circa 1962, introduced
Examples of veterinary uses	Substance used as a dip or spray to treat ectoparasitic insects, ticks and mites
Examples of species treated	Sheep; Goats; Cattle

Approval status

VMR 2013/2033 approval status (GB/UK)	Not approved
EU Regulatory approval status	Not approved

Chemical structure

Isomerism	Exists in two geometric isomeric forms: alpha (cis) isomer and beta (trans) isomer.
Chemical formula	C₁₂H₁₄Cl₃O₄P
Canonical SMILES	CCOP(=O)(OCC)OC(=CCl)C1=C(C=C(C=C1)Cl)Cl
Isomeric SMILES	CCOP(=O)(OCC)O/C(=C\Cl)/C1=C(C=C(C=C1)Cl)Cl
International Chemical Identifier key (InChIKey)	FSAVDKDHPDSCTO-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C12H14Cl3O4P/c1-3-17-20(16,18-4-2)19-12(8-13)10-6-5-9(14)7-11(10)15/h5-8H,3-4H2,1-2H3/b12-8-
2D structure diagram/image available?	Yes

General status

Veterinary substance type	Sheep dip, Insecticide
Substance groups	Organophosphate insecticide; Organophosphate acaricide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Contact and stomach action. Acetylcholinesterase (AChE) inhibitor.
Molecular targets	[Cholinesterase, Inhibitor]
CAS RN	470-90-6
EC number	207-432-0
CIPAC number	88
US EPA chemical code	084101
PubChem CID	5377784
CLP index number	015-071-00-3
Therapeutic Class	Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
ATCvet Code	QP53
Controlled Drug?	No
Regulation 37/2010 MRL Classification	-
Molecular mass	359.6
PIN (Preferred Identification Name)	(1E)-2-chloro-1-(2,4-dichlorophenyl)ethenyl diethyl phosphate
IUPAC name	(EZ)-2-chloro-1-(2,4-dichlorophenyl)vinyl diethyl phosphate
CAS name	2-chloro-1-(2,4-dichlorophenyl)ethenyl diethyl phosphate
Other status information	WFD priority substance; Marine, Surface and Groundwater Pollutant; Chemical subject to PIC regulations; PAN Bad Actor Chemical; Subject to the provisions of the UK Poisons Act 1972
Relevant Environmental Water Quality Standards	EU Directive 2008/105/EC EQS surface waters: annual average 0.1 µg l⁻¹; max measured 0.3 µg l⁻¹
Physical state	Colourless to amber liquid

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)		145	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	Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)		Miscible	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 Acetone	-
		Miscible	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 Ethanol	-
		Miscible	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 Xylene	-
		Miscible	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 Dichloromethane	-
Melting point (°C)		-20	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	-
Boiling point (°C)		167	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	6.31 X 1003	Calculated	-
	Log P	3.8	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	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)		1.36	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	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.0014	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	Low volatility
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)	40	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	Moderately persistent
	DT₅₀ (lab at 20 °C)	37	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data	Moderately persistent
	DT₅₀ (field)	30	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data	Moderately persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	Note	Lab studies DT₅₀ range 6-98 days, field study range 12-45 days; FAO state DT₅₀ 10-45 days
Manure DT₅₀ (days)		-	-	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	125	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data	Persistent
	Note	pH and temperature sensitive: DT₅₀ 29 days at pH 1 and 38 °C, 17 days at pH 9 and 38 °C, 1.3 hours at pH 13 and 20 °C, (L3)
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		7	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately fast
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)	-	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	Slightly mobile
	Koc (mL g⁻¹)	680
	Notes and range	Other literature data Koc 295 mL g⁻¹ (R4)
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		1.72	Calculated	Low leachability
Bio-concentration factor	BCF (l kg⁻¹)	250	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	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)		12	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 Rat	High
Mammals - Short term dietary NOEL	(mg kg⁻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 Rat	-
	(ppm diet)	3		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		80	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 Colinus virginianus	High
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		130	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source	Moderate
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)	4.1	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	Moderate
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	0.55	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 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)	-	-	-
		-
	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)		Harmless	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Chrysoperla carnea	-
Beneficial insects (Parasitic wasps)		-	-	-
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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		1.1	B3 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 3 = Unverified data of known source Oncorhynchus mykiss	Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		0.03	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Unknown species	Moderate
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.00025	B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 4 = Verified data Daphnia magna	High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		0.0001	P3 P = Other non-EU, UK or US Governments and Regulators 3 = Unverified data of known source Daphnia magna	High
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		> 0.0003	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 Ceriodaphnia dubia LC₅₀	High
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)		1.36	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 Scenedesmus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		1	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Unknown species	Moderate
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)		12	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 Rat	High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		31	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		0.05	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		Intraperitoneal LD₅₀ = 87.0 mg kg⁻¹	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source Mouse	-
		Intravenous LD₅₀ = 87.0 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		List I; List II	-	-
Exposure Routes	Public	-
	Occupational	Dermal and inhalation during pesticide handling Source: US EPA
Mammalian dose elimination route and rate		Majority excreted in the urine, much less in the faeces. Some also lost from the lungs.	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	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor No data found 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 ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data ✓Yes, known to cause a problem 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 No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		May cause bradycardia or tachycardia May cause Loss of muscle coordination, slurring of speech May cause mental confusion, disorientation and drowsiness Endocrine issues - Weak estrogen effect

Handling issues

Property	Value and interpretation
General	Prevent generation of mists Not expected to auto-ignite; Not highly flammable IMDG Transport Hazard Class 6.1
CLP classification 2013	Health: H300, H311 Environment: H400, H410
WHO Classification	Ib (Highly hazardous)
UN Number	UN3018
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	chlorfenvinphos
French	chlorfenviphos
German	Chlorfenvinphos
Danish	chlorfenvinphos
Italian	clorfenvinfos
Spanish	clorfenvinfos
Greek	chlorfenvinphos
Polish	chlorfenwinfos
Swedish	klorfenvinfos
Hungarian	-
Dutch	chloorfenvinfos
Norwegian	-

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Record last updated:	23/08/2024
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