Mephosfolan (Ref: ENT 25991 )

Mephosfolan (Ref: ENT 25991 )	Last updated: 24/07/2024
(Also known as: mephospholan; cytrolane)

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
	Ecotoxicity High alert: Birds acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An obsolete insecticide once used to control of many pests especially in aquatic situations

Example pests controlled

Lepidopterous spp.; Aphids; Bollworms; Mites; Thrips; Whiteflies

Example applications

Cotton; Maize; Rice; Potatoes; Sorghum; Hops

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

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

Chemical structure

Isomerism

A molecular with one chiral centre. Substance is racemic.

Chemical formula

C₈H₁₆NO₃PS₂

Canonical SMILES

CCOP(=O)(N=C1SCC(S1)C)OCC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

LTQSAUHRSCMPLD-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C8H16NO3PS2/c1-4-11-13(10,12-5-2)9-8-14-6-7(3)15-8/h7H,4-6H2,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance groups

Organophosphate insecticide; Phosphoramidate insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic. Acetylcholinesterase (AchE) inhibitor.

CAS RN

950-10-7

EC number

213-447-3

CIPAC number

None allocated

US EPA chemical code

268310

PubChem CID

13707

CLP index number

015-094-00-9

Molecular mass

269.32

PIN (Preferred Identification Name)

rac-diethyl [(2E,4R)-4-methyl-1,3-dithiolan-2-ylidene]phosphoramidate

IUPAC name

diethyl [(EZ)-4-methyl-1,3-dithiolan-2-ylidene]phosphoramidate

CAS name

diethyl (4-methyl-1,3-dithiolan-2-ylidene)phosphoramidate

Other status information

Marine Pollutant; Subject to the provisions of the UK Poisons Act 1972

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

Myzus persicae, Plutella xylostella, Tetranychus urticae

Physical state

Dark yellow liquid

Formulations

Property

Value

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

American Cyanamid Co.

Example products using this active

Cytro-Lane

Formulation and application details

Usually supplied as an emulsifiable concentrate or granular formulations

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

at 25 °C

Moderate

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

Melting point (°C)

Boiling point (°C)

120

Degradation point (°C)

Flashpoint (°C)

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

1.10 X 10⁰¹

Calculated

Log P

1.04

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.539

at 26°C

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

4.24

at 25 °C

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)

1.21 X 10^-05

at 25 °C

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)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

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)

K_oc (mL g⁻¹)

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

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

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

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 8.9

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 12.8

Coturnix japonica

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)

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)

0.0035

High

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)

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)

54.5

Cyprinus carpio

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)

0.0003

Unknown species

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)

> 52.8

Unknown species

Low

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)

> 8.9

Rat

High

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

9.7

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

Exposure Routes

Public

Occupational

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

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

No further information available

Handling issues

Property

Value and interpretation

General

Not compatible with strong acids or alkalis

CLP classification 2013

Health: H300, H310
Environment: H411

WHO Classification

Not classified: Obsolete (Not classified: Obsolete)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

mephosfolan

French

méphospholan

German

Mephosfolan

Danish

mephosfolan

Italian

mefosfolan

Spanish

mefosfolan

Greek

mephosfolan

Polish

mefosfolan

Swedish

Hungarian

Dutch

mefosfolan

Norwegian

Record last updated:	24/07/2024
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