Mevinphos (Ref: ENT 22374)

Mevinphos (Ref: ENT 22374)	Last updated: 18/01/2023
(Also known as: phosdrin; duraphos; mevinox; phosdrine; menite)

SUMMARY

Mevinphos is a highly toxic organophosphate insecticide. Known to cause significant inhibition of cholinesterase (ChE) activity by all routes of exposure. Readily soluble in water, volatile, slow aquatic hydrolysis, rapidly degrades in soil. Whilst the molecule is potentially mobile, it would not be expected to leach into groundwater due to rapid soil degradation. Extremely toxic to aquatic invertebrates, birds and mammals.

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 High alert: Drainflow: Mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Endocrine distrupter; Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide and acaricide used to control a broad spectrum of sucking and chewing insects

Example pests controlled

Aphids; Grasshoppers; Leafhoppers; Caterpillars; Spider mites; Cutworms

Example applications

Vegetables; Fruit; Field crops

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries

Introduction & key dates

circa 1955

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

Sweden

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

Additional information

Also used in

Australia

Chemical structure

Isomerism

isomeric mixture of E- and Z- isomeric forms

Chemical formula

C₇H₁₃O₆P

Canonical SMILES

CC(=CC(=O)OC)OP(=O)(OC)OC

Isomeric SMILES

C/C(=C\C(=O)OC)/OP(=O)(OC)OC

International Chemical Identifier key (InChIKey)

GEPDYQSQVLXLEU-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C7H13O6P/c1-6(5-7(8)10-2)13-14(9,11-3)12-4/h5H,1-4H3/b6-5+

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Organophosphate insecticide; Organophosphate acaricide

Minimum active substance purity

Known relevant impurities

May contain sulfotep, N-nitrosamines, halogenated dibenzo-pi-dioxins, halogenated dibenzofurans & PCBs

Substance origin

Synthetic

Mode of action

Systemic with contact, stomach and respiratory action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

7786-34-7

Alternative/old CAS RN

26718-65-0(E)/338-45-4(Z)

EC number

232-095-1

CIPAC number

US EPA chemical code

015801

PubChem CID

5355863

CLP index number

015-020-00-5

Molecular mass

224.1

PIN (Preferred Identification Name)

IUPAC name

methyl (EZ)-3-(dimethoxyphosphinoyloxy)but-2-enoate

CAS name

methyl 3-((dimethoxyphosphinyl)oxy)-2-butenoate

Other status information

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

Relevant Environmental Water Quality Standards

UK Statutory standard for the protection of aquatic life in freshwaters: 0.02 µg l⁻¹

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Musca domestica, Myzus persicae, Panonychus ulmi, Plusia gamma, Tetranychus urticae, many others

Physical state

Colourless to pale yellow liquid

Formulations

Property

Value

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

AMVAC Chemical Corp
Huikwang Corp.
Shell
Kenogard

Example products using this active

Phosdrin
Mevidrin
Apavinphos
Menite
Duraphos

Formulation and application details

Usually available as a liquid or emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

600000

High

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

Miscible

Acetone

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.34 X 10⁰⁰

Calculated

Log P

0.127

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.24

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

Highly volatile

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

6.30 X 10^-06

Non-volatile

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)

1.2

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General studies: DT₅₀ 1-4 hrs aerobic conditions, 1-12 days anaerobic conditions (R3)

Dissipation rate RL₅₀ on plant matrix

Value

0.77

Note

Published literature RL₅₀ range 0.38-1.4 days, 6 field & undercover grown crops, various matrices, n=6

Dissipation rate RL₅₀ on and in plant matrix

Value

0.6

Note

Published literature RL₅₀ range 0.5-0.7 days, 2 field crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Non-persistent

Note

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Mobile

K_oc

Notes and range

Other studies: 50.5-86.2 mL g⁻¹ (R3)

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.12

Calculated

Low leachability

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

Value

2.51 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3.5

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 4.63

Anas platyrhynchos

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)

0.094

Apis mellifera

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

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)

0.146

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)

0.002

Nomia melanderi

High

Mode of exposure

Contact

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Moderately harmful

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.012

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.00016

Daphnia pulex

High

Aquatic invertebrates - Chronic 21 day NOEC (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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 71

Unknown species

Low

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

Mesocosm study data

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)

3.5

Rat

High

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

4.0

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

7.3

Rat

Other Mammal toxicity endpoints

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

0.0008

JMPR 1996

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.003

JMPR 1996

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 II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Absorbed by the skin, inhalation and via the gastrointestinal tract - PPE/PPC essential

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

; ; ; ;

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

No information available

CLP classification 2013

Health: H300, H310
Environment: H400, H410

WHO Classification

Ia (Extremely hazardous)

UN Number

3018

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

mevinphos

French

mévinphos

German

Mevinphos

Danish

mevinphos

Italian

mevinfos

Spanish

mevinfos

Greek

mevinphos

Polish

mewinfos

Swedish

mevinfos

Hungarian

Dutch

mevinfos

Record last updated:	18/01/2023
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