Chlorfenvinphos (Ref: OMS 166)

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

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

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?

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

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Miscible

Acetone

Miscible

Ethanol

Miscible

Xylene

Miscible

Dichloromethane

Melting point (°C)

-20

Boiling point (°C)

167

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

6.31 X 10⁰³

Calculated

Log P

3.8

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.36

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.0014

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)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

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

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)

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

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

680

Notes and range

Other literature data K_oc 295 mL g⁻¹ (R4)

Freundlich

K_f (mL g⁻¹)

K_foc (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

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)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

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

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

Apis mellifera

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.55

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

Chrysoperla carnea

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Harmful

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

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.03

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

Daphnia magna

High

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.0001

Daphnia magna

High

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 0.0003

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

Scenedesmus subspicatus

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.05

Rat

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 87.0 mg kg⁻¹

Mouse

Intravenous LD₅₀ = 87.0 mg kg⁻¹

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.

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

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

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