Chlorfenvinphos (Ref: OMS 166)	Last updated: 22/12/2020
(Also known as: clofenvinfos; CVP; OMS 1328; ENT 24969; CGA 26351)

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SUMMARY

Chlorfenvinphos is an insecticide that is not approved for use in the EU. 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 distruper, 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	A soil applied insecticide used to control root-flies, rootworms and other soil pests. Also used as a sheep dip.
Example pests controlled	Ticks; Livestock flies; Mites; Root flies; Rootworms; Colorado beetle; Leafhoppers
Example applications	Potatoes; Rice; Vegetables including brassicas, swedes, turnips, carrots, onions; Citrus; Sugarcane; Sweetcorn
Efficacy & activity	-
Availability status	Current
Introduction & key dates	circa 1962

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	Germany
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	-
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

Also used in

Also used in	Australia, S. Africa, South & Central America, kenya

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

Pesticide type	Insecticide, Acaricide, Veterinary substance
Substance group	Organophosphate
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Contact and stomach action. Acetylcholinesterase (AChE) inhibitor.
CAS RN	470-90-6
EC number	207-432-0
CIPAC number	88
US EPA chemical code	084101
PubChem CID	5377784
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
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
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	1B
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Ceutorhynchus assimilis, Culex pipiens pipiens, Meligethes aeneus, Rhizoglyphus robini, Spodoptera litura, plus others
Physical state	Colourless to amber liquid

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Vinylphate Birlane Steladone Supona Apachlor Haptarax
Example products using this active	BASF Agro-Care Zagro Singapore Pte. Ltd. Kenogard
Formulation and application details	Available in a variety of formulations including emulsifiable concentrates, granules, seed treatments and wettable powders.

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 (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 (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 (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 (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 (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 (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)		Not expected to self ignite; Not highly flammable	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
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 (click here ) 5 = Verified data used for regulatory purposes	High
Bulk density (g ml⁻¹)		1.36	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.53	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
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)	40	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (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 (click here ) 4 = Verified data	Moderately persistent
	DT₅₀ (field)	30	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data	Moderately persistent
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Lab studies DT₅₀ range 6-98 days, field study range 12-45 days; FAO state DT₅₀ 10-45 days
Dissipation rate RL₅₀ on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	20.2	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	-
	Note	Lemon fruit, n=1
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 (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 4 = Verified data	Moderately fast

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	Slightly mobile
	Koc	680
	Notes and range	Other literature data Koc 295 mL g⁻¹ (R4)
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		1.72	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	5.04 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		Low	Calculated	-
Potential for loss via drain flow		Slightly mobile	Calculated	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
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		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		12	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (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 (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 (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)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		1.1	B3 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 3 = Unverified data of known source Salmonidae	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.03	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source Unknown species	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.00025	B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 4 = Verified data Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		0.0001	P3 P = Other governments and regulators 3 = Unverified data of known source Daphnia magna	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)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		1.36	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes Scenedemus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		1	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source Unknown species	Moderate
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)	0.55	B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here ) 5 = Verified data used for regulatory purposes	High
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
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 pollinators (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other pollinators (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		130	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Other soil macro-organisms	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Other arthropod (1)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	Harmful	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Typhlodromus pyri	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	Harmless	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Chrysoperla carnea	-
Soil micro-organisms		-	-	-
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 (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 / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Mouse	-
		Intravenous LD₅₀ = 87.0 mg kg⁻¹	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Mouse	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.0005	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data JMPR 1994	-
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
European MRLs		EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

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
CLP classification 2013	Health: H300, H311 Environment: H400, H410
EC Risk Classification	T+ - Very toxic: R28 T - Toxic: R24 N - Dangerous for the environment: R50, R53
EC Safety Classification	S2, S28, S36/37, S45, S60, S61
WHO Classification	Ib (Highly hazardous / Highly hazardous)
UN Number	3018
Waste disposal & packaging	-

TRANSLATIONS

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

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Record last updated:	22/12/2020
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