Mevinphos (Ref: ENT 22374)	Last updated: 27/11/2019
(Also known as: phosdrin; duraphos; mevinox; phosdrine; menite)

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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.

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	Obsolete
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 Directive 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

Also used in

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 group	Organophosphate
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	45
US EPA chemical code	015801
PubChem CID	5355863
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
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)	1B
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	Phosdrin Mevidrin Apavinphos Menite Duraphos
Example products using this active	AMVAC Chemical Corp Huikwang Corp. Shell Kenogard
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	M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems) (click here ) 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		Miscible	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Acetone	-
Melting point (°C)		21	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.34 X 1000	Calculated	-
	Log P	0.127	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low
Bulk density (g ml⁻¹)		1.24	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		17	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		6.30 X 10-06	H4 H = The US ARS pesticide properties database (click here ) 4 = Verified data	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	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Non-persistent
	DT₅₀ (lab at 20 °C)	3	DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. MS in preparation 4 = Verified data	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	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	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	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	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	27	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	Slow
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	17	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Non-persistent
	Note	-
Water-sediment DT₅₀ (days)		21	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Fast
Water phase only DT₅₀ (days)		5	K4 K = Research datasets, e.g. Pandora, Demetra 4 = Verified data	Moderately fast

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	G3 G = Extension Toxicology network database EXTOXNET (click here ) 3 = Unverified data of known source	Mobile
	Koc	44
	Notes and range	Other studies: 50.5-86.2 mL g⁻¹ (R3)
Freundlich	Kf	-	-	-
	Kfoc	-
	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	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source Based on LogP < 3	Low risk
	CT₅₀ (days)	-		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		3.5	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Rat	High
Mammals - Short term dietary NOEL	(mg kg⁻¹)	4	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 year	High
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 4.63	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Anas platyrhynchos	High
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.012	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.00016	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data 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)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		> 71	W2 W = French database provided by ARVALIS-Institut du Végétal 2 = Unverified data of unknown source Unknown species	Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
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)	0.027	G3 G = Extension Toxicology network database EXTOXNET (click here ) 3 = Unverified data of known source	High
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 pollinators (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	0.146	R4 R = Peer reviewed scientific publications 4 = Verified data Megachile rotundata	High
	Mode of exposure	Contact
Other pollinators (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	0.002	R4 R = Peer reviewed scientific publications 4 = Verified data Nomia melanderi	High
	Mode of exposure	Contact
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Other soil macro-organisms	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Other arthropod (1)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	Harmful	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Typhlodromus pyri	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	Moderately harmful	AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005 2 = Unverified data of unknown source Chrysoperla carnea	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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	G4 G = Extension Toxicology network database EXTOXNET (click here ) 4 = Verified data Rat	High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		4.0	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		7.3	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source Rat	-
Other Mammal toxicity endpoints		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.0008	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data JMPR 1996	-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)		0.003	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data 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
European MRLs		EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor XNo, known not to cause a problem A3 A = Chromosome aberration (EFSA database) 3 = Negative ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data ✓Yes, known to cause a problem Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant No data found ✓Yes, known to cause a problem ✓Yes, known to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem ✓Yes, known to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem 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
EC Risk Classification	T+ - Very toxic: R27/28 N - Dangerous for the environment: R50, R53
EC Safety Classification	S1/2, S23, S28, S36/37, S45, S60, S61
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

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Record last updated:	27/11/2019
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