Tetrachlorvinphos (Ref: SD 8447)

Tetrachlorvinphos (Ref: SD 8447)	Last updated: 22/08/2024
(Also known as: stirofos; CVMP)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Drainflow: Slightly mobile Warning: Significant data are missing	Ecotoxicity High alert: Daphnia acute ecotoxicity: High	Human health High alert: Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide and acaricide for use against various pests of fruits, vegetables, ornamental plants, forest trees and livestock on agricultural and recreational areas

Example pests controlled

Aphids; Mites; Fleas; Ticks; Thrips; leafhoppers; Spider mites

Example applications

Potatoes; Beets; Cereals; Vegetables including brassicas; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

1967, registered USA

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

USA, Evidence of use in third world countries

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

Pesticide type

Insecticide, Acaricide, Veterinary substance

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.

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

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

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Amblyseius fallacis, Bucculatrix thurberiella, Leptinotarsa decemlineata, Myzus persicae, many others

Physical state

Off-white crsytalline solid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

ISK Biosciences
DuPont
BASF
Shell

Example products using this active

Appex
Rabon
Gardona
Ravap
Gardcide

Formulation and application details

Available in a wide variety of different formulations including concentrates, granules, powders and inpregnated collars

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

11.6

Moderate

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

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

3.39 X 10⁰³

Calculated

Log P

3.53

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.52

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.0056

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.86 X 10^-04

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)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.0

Note

Published literature RL₅₀ range 2.0-6.0 days, leaves of 2 field crops, n=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

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

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

900

Notes and range

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

0.31

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

7.06 X 10^-04

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

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

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

125

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

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

Apis mellifera

Moderate

Chronic

Notes

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

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

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 (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

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

Rat

Low

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

1500

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.85

Rat

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ > 5000 mg kg⁻¹

Guinea pig

Subcutaneous LD₅₀ > 5000 mg kg⁻¹

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

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Metabolised and mainly excreted in the urine

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

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