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

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION
for fenamiphos

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

Introduction: 1967, first reported; 1968, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Netherlands
Date inclusion expires 31/07/2017

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

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also registered in: Australia, USA

General status:
Pesticide type Nematicide
Substance group Organophosphate
Substance origin Synthetic
Mode of action Systemic, conatct action, absorbed through roots
CAS RN 22224-92-6
EC number 244-848-1
CIPAC number 692
US EPA chemical code 100601
Chiral molecule Chiral, a specific isomer or a derivative of a chiral molecule
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
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
  • Bayer CropScience
  • King Tech Corp
  • AgroCare
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) 0.12 A5 Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1) 9.90 X 10-05 A5 Non-volatile
Henry's law constant at 20oC (dimensionless) 3.00 X 10-08 K3 Non-volatile
GUS leaching potential index -0.11 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Value 2.82 X 10-04 Calculated -
Note -
Potential for particle bound transport index - Calculated Low
Maximum UV-vis absorption L mol-1 cm-1 201nm = 24300, 251nm = 11400, 287nm = 1400 A5 -
Surface tension (mN m-1) 47.2 A5 at 20oC -

Degradation:
Property Value Source/Quality Score/Other Information Interpretation
Soil degradation (days) (aerobic) DT50 (typical) 0.85 A5 Non-persistent
DT50 (lab at 20oC) 0.85 A5 Non-persistent
DT50 (field) 1.8 A5 Non-persistent
DT90 (lab at 20oC) 2.95 A5 -
DT90 (field) - - -
Note EU dossier lab studies DT50 range 0.4-1.4 days, DT90 range 1.3-4.6 days; field studies DT50 range 1.5-2.2 days; Other sources: 50 days (DW3)
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 - DW3 Moderately mobile
Koc 100
Notes and range -
Freundlich Kf 1.03 A5 Moderately mobile
Kfoc 266
1/n 0.935
Notes and range EU dossier Kf range 0.70-1.37 mL/g, Kfoc range 148-469 mL/g, 1/n range 0.90-0.95, Soils=4
pH sensitivity -

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 91/414 relevancy
fenamiphos sulfoxide Soil   0.791   Major fraction, Relevant
fenamiphos sulfone Soil   0.228   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
3-methyl-4-[methylsulfonyl]phenol
Note: Rat LD50 1250 mg kg-1 bw
fenamiphos sulfone phenol; fenamiphos metabolite M13 Soil (Aerobic) - -
- 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 - -
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 - -
3-methyl-4-[methylsulfinyl]phenol
Note: DT50 soil = 30 days
fenamiphos sulfoxide phenol; fenamiphos metabolite M12 Soil (Aerobic); Water; Rat 0.25 -


ECOTOXICOLOGY

for fenamiphos

Property Value Source/Quality Score/Other Information Interpretation
Bio-concentration factor BCF 110 A5 Threshold for concern
CT50 (days) 0.22 -
Bioaccumulation potential - Calculated Moderate
Mammals - Acute oral LD50 (mg kg-1) > 6 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 -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.0019 L3 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.01 A4 Daphnia magna -
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) - - -
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 High
Oral acute 48 hour LD50 (μg bee-1) - - -
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
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Harmful at 0.01 kg ha-1
% Effect - - -
Other arthropod (2) LR50 g ha-1 1.7 7 day
A5 Typhlodromus pyri, protonymph
Harmful at 1 kg ha-1
Harmful at 0.1 kg ha-1
Moderately harmful at 0.01 kg ha-1
% 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
Mammals - Acute oral LD50 (mg kg-1) > 6 A5 Rat High
Mammals - Dermal LD50 (mg kg-1 body weight) 82 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 0.072 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.0008 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 dependant -
Dangerous Substances Directive 76/464 List I; List II - -
Exposure Limits - - -
Exposure Routes Public Negligible risk to bystanders
Occupational Negligible risk to operators
Examples of European MRLs (mg kg-1) Value Sweet peppers: 0.1; Brussel sprouts, cabbages, cucumbers, melons (not watermelons), summer squash, eggplants, tomatoes and carrots: 0.05; Other vegetables, fruit and cereal grains: 0.02
Note Current May 2007.
For the EU pesticides database click here
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant Respiratory tract irritant Skin irritant Eye irritant

-

-

-

General human health issues Toxic by inhalation and skin contact
Exposure may be fatal due to respiratory failure

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

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 -
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

Record last updated: Saturday 02 August 2014
Contact: aeru@herts.ac.uk