mevinphos (Ref: ENT 22374) ** phosdrin ** duraphos ** mevinox ** phosdrine ** menite ** Translations

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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
for mevinphos

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Availability status: Obsolete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

EC Regulation 1107/2009 (repealing 91/414):

Status	Not approved
Dossier rapporteur/co-rapporteur	Sweden
Date inclusion expires	Expired
EU Candidate for substitution (CfS)	-
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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 (g mol-1)	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 ug/L
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
Related substances & organisms	-

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
UK LERAP status	No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details	Usually available as a liquid or emulsifiable concentrate.

ENVIRONMENTAL FATE
for mevinphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		600000	M4	High
Solubility - In organic solvents at 20oC (mg l-1)		Miscible	L2 - Acetone	-
Melting point (oC)		21	Q3	-
Boiling point (oC)		-	-	-
Degradation point (oC)		-	-	-
Flashpoint (oC)		-	-	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.34 X 1000	Calculated	-
	Log P	0.127	L3	Low
Bulk density (g ml-1)/Specific gravity		1.24	L3	-
Dissociation constant (pKa) at 25oC		-	-	-
		Note:
Vapour pressure at 20oC (mPa)		17	L3	Highly volatile
Henry's law constant at 25oC (Pa m3 mol-1)		6.30 X 10-06	H4	Non-volatile
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		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		-	-	-
Surface tension (mN m-1)		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	1.2	K4	Non-persistent
	DT50 (lab at 20oC)	3	DW4	Non-persistent
	DT50 (field)	-	-	-
	DT90 (lab at 20oC)	-	-	-
	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	-
	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	-
	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	Slow
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	17	K4	Non-persistent
	Note	-
Water-sediment DT50 (days)		21	K4	Fast
Water phase only DT50 (days)		5	K4	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	G3	Mobile
	Koc	44
	Notes and range	Other studies: 50.5-86.2 mL/g (R3)
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

ECOTOXICOLOGY
for mevinphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	Q3 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		3.5	G4 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	4	L2 Rat, 2 year	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 4.63	G4 Anas platyrhynchos	High
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		0.012	G4 Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l-1)		-	-	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.00016	F4 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 Unknown species	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	-	-	-
	Oral acute 48 hour LD50 (μg bee-1)	-	-	-
	Unknown mode acute 48 hour LD50 (μg bee-1)	0.027	G3	High
Earthworms - Acute 14 day LC50 (mg kg-1)		-	-	-
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	Harmful	AA2 Typhlodromus pyri	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	Moderately harmful	AA2 Chrysoperla carnea	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for mevinphos

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		3.5	G4 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		4.0	L3 Rat	-
Mammals - Inhalation LC50 (mg l-1)		7.3	R3 Rat	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.0008	JMPR 1996	-
ARfD - Acute Reference Dose (mg kg-1bw 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-1bw day-1)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
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		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-		-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		No further information available

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
US EPA Classification (formulation)		I	-	Danger - Highly toxic
UN Number		3018
Waste disposal & packaging		-

TRANSLATIONS
for mevinphos

Language	Name
English	mevinphos
French	mévinphos
German	Mevinphos
Danish	mevinphos
Italian	mevinfos
Spanish	mevinfos
Greek	mevinphos
Slovenian	mevinfos
Polish	mewinfos
Swedish	mevinfos
Hungarian	-
Dutch	mevinfos

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Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk