Carbophenothion (Ref: ENT 23708)

Carbophenothion (Ref: ENT 23708)	Last updated: 28/08/2024
(Also known as: carbofenotion; R-1303; Stauffer R-1,303)

SUMMARY

Carbophenothion is an insecticide used on a broad range of crops. The substance has a low aqueous solubility, low volatility and, based on its chemical properties, would not be expected to leach to groundwater. It may be quite persistent in soil systems. It is highly toxic to mammals and may also be a cholinesterase inhibitor and a neurotoxin. In most instances it shows a moderate to high level of toxicity to aquatic and terrestrial species.

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: Moderately persistent; Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High Warning: Significant data are missing	Human health High alert: Mammals acute toxicity: High; Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An obsolete insecticide and acaricide once used to control pests on fruit and other crops. It is used to control parasites on animals.

Example pests controlled

Aphids; Spider mites; Mealybugs; Weevils; Leaf hoppers; Armyworms

Example applications

Fruit including citrus, pears, apples; Cotton; Nuts; Vegetables; Sorghum; Maize; Sugarbeet

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

1955, 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 plant protection agent

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

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

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₁₆ClO₂PS₃

Canonical SMILES

CCOP(=S)(OCC)SCSC1=CC=C(C=C1)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

VEDTXTNSFWUXGQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H16ClO2PS3/c1-3-13-15(16,14-4-2)18-9-17-11-7-5-10(12)6-8-11/h5-8H,3-4,9H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide; Acaricide

Substance groups

Organophosphate insecticide; Organothiophosphate insecticide; Organophosphate acaricide; Organothiophosphate acaricide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Contact and stomach action with long residual activity. Acetylcholineesterase inhibitor.

CAS RN

786-19-6

EC number

212-324-1

CIPAC number

140

US EPA chemical code

058102

PubChem CID

13081

CLP index number

015-044-00-6

Molecular mass

342.9

PIN (Preferred Identification Name)

S-{[(4-chlorophenyl)sulfanyl]methyl} O,O-diethyl phosphorodithioate

IUPAC name

S-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate

CAS name

S-(((4-chlorophenyl)thio)methyl) O,O-diethyl phosphorodithioate

Other status information

Severe Marine Pollutant; PAN Bad Actor Chemical

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

Panonychus citri, Tetranychus mcdanieli, Tetranychus viennensis, Boophilus microplus, plus others

Physical state

Yellow/brown liquid

Formulations

Property

Value

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

Stauffer

Example products using this active

Oleoakarithion
Garrathion
Acarithion
Danifos
Trithion
Atlas Trithion

Formulation and application details

Available in several formulations including dusts

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.34

Low

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

Miscible

Ethanol

Miscible

Acetone

Miscible

Xylene

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

5.62 X 10⁰⁴

Calculated

Log P

4.75

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.27

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

1.07

Low volatility. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

5.80 X 10^-01

Moderately 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)

100

Persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.5

Note

Published literature RL₅₀ range 4.5-4.6 days, Orange leaves, various matrices, n=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

11.0

Note

Published literature RL₅₀ range 5.1-18.5 days, 2 citrus crops, various matrices, n=3

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)

Non-mobile

K_oc (mL g⁻¹)

50000

Notes and range

Best available data

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

-1.03

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

1000

Estimated

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)

0.5

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

121

Anas platyrhynchos

Moderate

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)

< 1.4

Moderate

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)

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)

0.162

Megachile rotundata

High

Mode of exposure

Contact

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)

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)

0.056

Oncorhynchus mykiss

High

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

0.0063

Pimephales promelas

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

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)

0.025

Americamysis bahia

High

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)

Rat

High

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.0005

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 - PPE/PPC required

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

The majority is excreted in urine and faeces within 72 hours

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Prevent mist formation
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H311
Environment: H400, H410

WHO Classification

Not classified: Obsolete (Not classified: Obsolete)

UN Number

UN3018

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

carbophenothion

French

carbophenothion

German

Carbophenothion

Danish

carbophenothion

Italian

carbofenotion

Spanish

carbofenotion

Greek

carbophenothion

Polish

karbofenotion

Swedish

Hungarian

Dutch

carbofenothion

Norwegian

Record last updated:	28/08/2024
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