Select Option
Home
A to Z
Search
Terms & Conditions
Support Information
Purchasing & Other Services
Video User Guides
GET ADDITIONAL DATA HERE!

phenmedipham (Ref: SN 38584)
** fenmedifam ** phenmediphame ** EP-452 ** betanal ** Translations

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

SUMMARY

Phenmedipham is a carbamate herbicide approved for the control of broadleaved weeds at EU level. It has a low aqueous solubility, a low volatility and is not generally expected to leach to groundwaters. It is not normally persistent in soil or water systems. It has a low mammalian toxicity but has been associated with the development of some cancers. Phenmedipham is moderately toxic to most aquatic and terrestrial fauna and flora.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for phenmedipham

Description: A herbicide used to control most broad-leaved weeds in their early growth stages

Example pests controlled: Kochia; Lambsquarters; Mustard; Foxtail; Shepherds purse; Chickweed; Goosefoot; Ragweed

Example applications: Sugar beet; Fodder beet; Red beet; Mangels; Spinach; Swiss chard; Strawberries

Efficacy & activity: Shown to control a wide range of broad-leaved weeds in numerous field trials.

Availability status: Current

Introduction & key dates: 1967, first reported

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Finland/Denmark
Date inclusion expires 31/07/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

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: Click here for further information on the general chemical status information used on this site
Isomerism -
Chemical formula C16H16N2O4
Canonical SMILES CC1=CC(=CC=C1)NC(=O)OC2=CC=CC(=C2)NC(=O)OC
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) IDOWTHOLJBTAFI-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C16H16N2O4/c1-11-5-3-6-12(9-11)18-16(20)22-14-8-4-7-13(10-14)17-15(19)21-2/h3-10H,1-2H3,(H,17,19)(H,18,20)
2D structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Carbamate
Minimum active substance purity 970 g/kg
Known relevant impurities EU dossier - toluene, 3-methylaniline, 3-aminophenol
Substance origin Synthetic
Mode of action Selective, systemic, absorbed through leaves and translocated. Inhibits photosynthesis (photosystem II).
CAS RN 13684-63-4
EC number 237-199-0
CIPAC number 77
US EPA chemical code 098701
PubChem CID 24744
Molecular mass (g mol-1) 300.31
PIN (Preferred Identification Name) -
IUPAC name methyl 3-(3-methylcarbaniloyloxy)carbanilate
CAS name 3-[(methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) C1
Herbicide Resistance Classification (WSSA) 5
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Colourless crystalline powder
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • AgriGuard
  • Bayer CropScience
  • Landgold
  • Makhteshim-Agan
  • Nufarm UK
Example products using this active
  • Betana Carrera
  • Betana Expert
  • Betanal Flow
  • PowerTwin
  • Pump
  • Twin
UK LERAP status None
Formulation and application details Often supplied as a soluble or emulsifiable concentrate or liquid concentrate.


ENVIRONMENTAL FATE

for phenmedipham

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 1.8 A4 - @ pH 3.4 Low
Solubility - In organic solvents at 20oC (mg l-1) 970 A5 - Toluene -
36800 A5 - Methanol -
193000 A5 - Acetone -
65000 A5 - Ethyl acetate -
Melting point (oC) 148.3 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 240 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 5.01 X 1002 Calculated -
Log P 2.7 A5 Moderate
Bulk density (g ml-1)/Specific gravity 1.36 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 7.00 X 10-07 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 2.7 X 10-08 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.02 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 1.56 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated Medium
Maximum UV-vis absorption L mol-1 cm-1 Neutral soln: 205nm = 59646, 237nm = 37848, 274nm = 2761 A5 -
Surface tension (mN m-1) 70.5 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability Not readily biodegradable
Soil degradation (days) (aerobic) DT50 (typical) 12 A5 Non-persistent
DT50 (lab at 20oC) 12 A5 Non-persistent
DT50 (field) 16.7 A5 Non-persistent
DT90 (lab at 20oC) 118.8 A5 -
DT90 (field) 74.3 A5 -
DT50 modelling endpoint 95.5 A5 -
Note EU 2016 dossier lab studies DT50 range 4.2-139.8 days, DT90 range13.4-317.3 days, Soils=12; Field studies DT50 range 5.8-39.9 days, DT90 range 30-132.6 days, Soils=5
Dissipation rate RL50 on plant matrix Value - - -
Note -
Dissipation rate RL50 on and in plant matrix Value - - -
Note -
Aqueous photolysis DT50 (days) at pH 7 Value Stable A5 -
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 0.5 A5 Non-persistent
Note pH sensitive: DT50 259 days at pH 4, 47 days at pH 5, 12 hours at pH 7, 7 minutes at pH 9, all at 25 degC
Water-sediment DT50 (days) 0.12 A5 Fast
Water phase only DT50 (days) 0.2 A5 Fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 35.2 A5 Slightly mobile
Koc 1775
Notes and range EU 2016 dossier Kd range 11.9-64.3 mL/g, koc range 1631-2015 mL/g, Soils = 3; Other sources: 2400 mL/g (DW3)
Freundlich Kf 20.22 A5 Slightly mobile
Kfoc 1142
1/n 0.81
Notes and range EU 2016 dossier Kf range 4.5-42.1 mL/g, Kfoc range 657-1618 mL.g, 1/n range 0.77-0.87, Soils =10
pH sensitivity Yes, due to the hydrolysis processes which indirectly affects the adsorption.

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
methyl-3-hydroxylphenylcarbamate This metabolite may cause environmental pollution, click here for further information Soil   0.140   Major fraction, Relevant
3-aminophenol Soil   0.04   Minor fraction, Relevant
3-aminotoluene Soil   -   Minor fraction, Relevancy unknown


ECOTOXICOLOGY

for phenmedipham

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 165 A5 Threshold for concern
CT50 (days) 6 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) - L2 Rat, 2 year -
(ppm diet) > 100 -
Birds - Acute LD50 (mg kg-1) > 2500 A5 Anas platyrhynchos Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) 1.71 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.32 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 2.03 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.061 A5 Daphnia magna Moderate
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) 0.37 A5 Chironomus riparius Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.23 A5 Lemna minor Moderate
Non-target plants > 2.0 A5 Onion, Lettuce
Seedling emergence, ER50
as g/ha
-
2.7 A5 Tomato
Vegetative vigour, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.086 A4 Raphidocelis subcapitata, 72 hour Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Apis mellifera Low
Oral acute 48 hour LD50 (μg bee-1) > 104.8 A5 Apis mellifera Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 36 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 3.33 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 - - -
% Effect 63 Mortality
Dose: 0.48 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 - - -
% Effect 0 Mortality
Dose: 0.48 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect [Dose: 13 mg kg-1 soil]
Carbon mineralisation: Slight reversable effects [Dose: 1 kg ha-1]
A5 -
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for phenmedipham

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2500 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 7.0 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.13 A5 Rat, 90 day, SF=100 -
Dermal penetration studies (%) 0.2-1.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks to bystanders or residents identified
Occupational No unacceptable risks to operators or other workers identified but PPE/PPC recommended
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 Moderately toxic
May cause dermatitis
Possible blood, spleen, liver & kidney toxicant

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

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 {Health: H373, H351, H361d
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S60, S61
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) IV - Caution - Not acutely toxic
UN Number Usually 3077 or 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for phenmedipham

Language Name
English phenmedipham
French phenmediphame
German Phenmedipham
Danish phenmedipham
Italian fenmedifam
Spanish fenmedifam
Greek -
Slovenian fenmedifam
Polish fenmedifam
Swedish fenmedifam
Hungarian fenmedifam
Dutch fenmedifam

Record last updated: Monday 29 October 2018
Contact: aeru@herts.ac.uk