fenamiphos (Ref: BAY 68138) ** phenamiphos ** methaphenamiphos ** SRA 3886 ** Translations

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SUMMARY

Fenamiphos is an organophosphorous pesticide that is currently approved for use in the EU. It is moderately soluble in water, has a low volatility and would not normally, based on its chemical properties, be expected to leach to groundwater. It is not normally persistent in soil or water systems. It is highly toxic to mammals, a cholinesterase inhibitor and a neurotoxicant. It shows moderate to high toxicity to most fauna and flora.

GENERAL INFORMATION
for fenamiphos

Description: An insecticide and nematicide used to control ecoparasitic, endoparasitic, free-living and cyst-forming nematodes

Example pests controlled: Nematodes, Thrips

Example applications: Fruit including citrus, grapes and pineapples; Glasshouse crops including tomatoes, peppers;, aubergine, cucumber, zucchini; Vegetables; Peanuts; Tobacco; Turf; Ornamentals including herbaceous plants and nursery stock

Efficacy & activity: Efficacy demonstrated by long term use across the EU and in other countries.

Availability status: Current

Introduction & key dates: 1967, first reported; 1968, first introduced; first registered in the United States in 1972

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

Status	Approved
Dossier rapporteur/co-rapporteur	Greece/Cyprus
Date inclusion expires	31/07/2018
EU Candidate for substitution (CfS)	Yes - low ADI / ARfD / AOEL

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, USA

General status:

Pesticide type	Nematicide
Substance group	Organophosphate
Minimum active substance purity	940 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Systemic, contact action, absorbed through roots
CAS RN	22224-92-6
EC number	244-848-1
CIPAC number	692
US EPA chemical code	100601
Isomerism	Chiral, a specific isomer or a derivative of a chiral molecule. Fenamiphos is a racemic mixture having equal amounts of both enantiomers in a 50 : 50 ratio.
Chemical formula	C13H22NO3PS
SMILES	O=P(OCC)(Oc1ccc(SC)c(c1)C)NC(C)C
International Chemical Identifier key (InChIKey)	ZCJPOPBZHLUFHF-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C13H22NO3PS/c1-6-16-18(15,14-10(2)3)17-12-7-8-13(19-5)11(4)9-12/h7-10H,6H2,1-5H3,(H,14,15)
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	303.36
PIN (Preferred Identification Name)	(E)-[ethyl 3-methyl-4-(methylsulfanyl)phenyl propan-2-ylphosphoramidate]
IUPAC name	(RS)-(ethyl 4-methylthio-m-tolyl isopropylphosphoramidate)
CAS name	ethyl 3-methyl-4-(methylthio)phenyl (1-methylethyl)phosphoramidate
Other status information	Potential groundwater contaminant; Marine Pollutant
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	-
Physical state	Colourless crystals to tan waxy solid depending on purity
Related substances & organisms	-

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Bayer CropScience King Tech Corp AgroCare Mobay
Example products using this active	Nemacur CS 240
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Often supplied as a capsule suspension that is diluted with water and applied by drip irrigation or via a spray followed by incorporation into the soil.

ENVIRONMENTAL FATE
for fenamiphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		345	A5	Moderate
Solubility - In organic solvents at 20oC (mg l-1)		27000	A5 - n-Hexane	-
		250000	A5 - Acetone	-
		250000	A5 - Ethyl acetate	-
		250000	A5 - Dichloromethane	-
Melting point (oC)		46	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		200	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	2.00 X 1003	Calculated	-
	Log P	3.3	A4	High
Bulk density (g ml-1)/Specific gravity		1.19	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 25oC (mPa)		0.067	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.80 X 10-05	A5	Non-volatile
GUS leaching potential index		-0.09	Calculated	Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	4.43 X 10-04	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		In acetoniltrile: 251nm=11738, 290nm=1531	A5	-
Surface tension (mN m-1)		47.2	A5 at 20 oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	0.90	A5	Non-persistent
	DT50 (lab at 20oC)	0.9	A5	Non-persistent
	DT50 (field)	1.8	A5	Non-persistent
	DT90 (lab at 20oC)	3.51	A5	-
	DT90 (field)	-	-	-
	DT50 modelling endpoint	-	-	-
	Note	EU 2017 dossier lab studies DT50 range 0.366-2.01 days, DT90 range 1.28-7.06 days, Soils=4; EU 2006 dossier field studies DT50 range 1.5-2.2 days; Other sources: 50 days (DW3)
Dissipation rate RL50 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL50 on and in plant matrix	Value	6.5	R4	-
	Note	Published literature RL50 range 6.3-6.7 days, 2 field crops, various matrices, n=2
Aqueous photolysis DT50 (days) at pH 7	Value	0.2	A4	Fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	304	A5	Persistent
	Note	pH sensitive: 252 days at pH 5, 236 days at pH 9 all at 20 degC
Water-sediment DT50 (days)		60.2	A4	Moderately fast
Water phase only DT50 (days)		5.8	A4	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	10.1	A5	Moderately mobile
	Koc	446.2
	Notes and range	EU 2017 dossier Kd range 4.2-23.0 mL/g, Koc range 124-878 mL/g, Soils=5
Freundlich	Kf	1.86	A5	Moderately mobile
	Kfoc	125.2
	1/n	0.92
	Notes and range	EU 2017 dossier Kf range 0.79-3.4 mL/g, Kfoc range 43.8-240.9 mL/g, 1/n range 0.85-0.92, Soils=8
pH sensitivity		None

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
fenamiphos sulfoxide		Soil	0.772	Major fraction, Relevant
fenamiphos sulfone		Soil	0.293	Major fraction, Relevant
fenamiphos sulfoxide phenol		Soil	0.065	Minor fraction, Relevant
fenamiphos sulfone phenol		Soil	0.251	Major fraction, Relevant
fenamiphos sulfone anisole (Ref: )		Soil	0.082	Minor fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
ethyl 3-methyl-4-(methylthio)phosphoramidic acid phenyl ester	des-isopropyl fenamiphos; fenamiphos metabolite M06	unknown	-	-
Ethyl 3-methyl-4-(methylsulfinyl)phosphoric acid phenyl ester	des-isopropylamino fenamiphos sulfoxide; fenamiphos metabolite M09	unknown	-	-
-	fenamiphos sulfonic acid	Water (Photolysis)	-	-
4-hydroxy-2-methylbenzenesulfonic acid	fenamiphos phenol sulfonic acid; fenamiphos metabolite M24	Water (Photolysis); Rat	-	-
3-methyl-4-(methylthio)phenol	fenamiphos phenol; fenamiphos metabolite M11	Rat	-	-

ECOTOXICOLOGY
for fenamiphos

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	110	A5	Threshold for concern
	CT50 (days)	0.22		-
Mammals - Acute oral LD50 (mg kg-1)		> 6.0	A5 Rat	High
Mammals - Short term dietary NOEL	(mg kg-1)	> 0.3	A5 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		0.8	A5 Colinus virginianus	High
Birds - Short term dietary (LC50/LD50)		> 43 mg kg feed-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.0093	A5 Oncorhynchus mykiss	High
Fish - Chronic 21 day NOEC (mg l-1)		0.0038	A5 Oncorhynchus mykiss	High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.0011	A5 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.01	A4 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.0057	F3 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)		0.01	A4 Chironomus riparius, emergence	Moderate
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)		3.8	A5 Scenedemus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	0.28	A5 Apis mellifera	High
	Oral acute 48 hour LD50 (μg bee-1)	0.45	A5 Apis mellifera	High
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		888	A5 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		0.49	A3 Eisenia foetida	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	0.175	48 hour A5 Aphidius rhopalosiphi, adult	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	1.7	7 day A5 Typhlodromus pyri, protonymph	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: >25% effect Carbon mineralisation: No significant adverse effect	A5 Dose: 133 mg kg-1 soil, 28 days	-
Mesocosm study data	NOEAEC mg l-1	0.0035	A5 Fish and aquatic invertebrates	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for fenamiphos

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)		> 6.0	A5 Rat	High
Mammals - Dermal LD50 (mg kg-1 body weight)		72.0	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		0.065	A5 Rat, 4 hr (aerosl)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.0006	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.0025	A5 Dog, SF=100	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.0008	A5 Dog, SF=100	-
Dermal penetration studies (%)		1.0-5.0	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List I; List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Negligible risk to bystanders
	Occupational	Negligible risk to operators
European MRLs		Click here for the EU MRL pesticide database
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		Toxic by inhalation and skin contact Exposure may be fatal due to respiratory failure May overstimulate the nervous system causing nausea, dizziness and confusion Inhibition of erythrocyte ChE activity

: 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		Not explosive or oxidising IMDG Transport Code is usually 6.1
CLP classification 2013		Health: H300, H301, H310, H319, H330, H362 Environment: H400, H410
EC Risk Classification		T+ - Very toxic: R28 T - Toxic: R24 N - Dangerous for the environment: R50, R53
EC Safety Classification		S1/2, S23, S28, S36/37, S45, S60, S61
WHO Classification		Ib	-	Highly hazardous
US EPA Classification (formulation)		I	-	Danger - Highly toxic
UN Number		2783
Waste disposal & packaging		Packaging Group I (great danger)

TRANSLATIONS
for fenamiphos

Language	Name
English	fenamiphos
French	phenamiphos
German	Fenamiphos
Danish	fenamiphos
Italian	fenamifos
Spanish	fenamifos
Greek	fenamiphos
Slovenian	fenamifos
Polish	fenamifos
Swedish	-
Hungarian	-
Dutch	fenamifos

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Record last updated: Wednesday 21 March 2018
Contact: aeru@herts.ac.uk