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desmedipham (Ref: EP 475)
** DMP ** desmediphame ** Translations

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

SUMMARY

Desmedipham is a post-emergence herbicide that is approved for use in the EU. It has a low aqueous solubility and is semi-volatile. It is not usually persistent in soils or in water. Desmedipham is relatively non-toxic to mammals and is also an irritant. It is moderately toxic to birds, most aquatic organisms, honeybees and earthworms.

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

Description: A post-emergence herbicide used to control broad-leaved weeds and grasses

Example pests controlled: Bindweed; Charlock; Chickweed; Cleavers; Fathen; Mayweed; Redshank; Knotgrass; Deadnettle

Example applications: Sugarbeet; Fodder beet; Red beet; Mangels; Strawberry; Spinach; Peas

Efficacy & activity: Efficacy established due to long-term applications in the field and by research trials

Availability status: Current

Introduction & key dates: 1969, 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

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism None
Chemical formula C16H16N2O4
Canonical SMILES CCOC(=O)NC1=CC(=CC=C1)OC(=O)NC2=CC=CC=C2
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) WZJZMXBKUWKXTQ-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C16H16N2O4/c1-2-21-15(19)18-13-9-6-10-14(11-13)22-16(20)17-12-7-4-3-5-8-12/h3-11H,2H2,1H3,(H,17,20)(H,18,19)
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 <2g/kg; 3-aminophenol <1g/kg; Aniline < 0.5 g/kg
Substance origin Synthetic
Mode of action Selective, systemic, absorbed through leaves. Inhibits photosynthesis (photosystem II).
CAS RN 13684-56-5
EC number 237-198-5
CIPAC number 477
US EPA chemical code 104801
PubChem CID 24743
Molecular mass (g mol-1) 300.31
PIN (Preferred Identification Name) ethyl {3-[(phenylcarbamoyl)oxy]phenyl}carbamate
IUPAC name ethyl 3-phenylcarbamoyloxycarbanilate
CAS name ethyl [3-[[(phenylamino)carbonyl]oxy]phenyl]carbamate
Other status information Marine Pollutant
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 crystals
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
  • King Tech
Example products using this active
  • Betana Carrera
  • Betanal Expert
  • Alphanex
  • Venzar Flowable
UK LERAP status None
Formulation and application details Usually supplied as an emulsifiable concentrate.


ENVIRONMENTAL FATE

for desmedipham

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) 5.6 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 20 A5 - Hexane -
1200 A5 - Toluene -
187000 A5 - Methanol -
285000 A5 - Acetone -
Melting point (oC) 118.5 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 295 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 1.32 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 4.0 X 10-05 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 5.40 X 10-07 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 0.66 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 1.26 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 High
Maximum UV-vis absorption L mol-1 cm-1 Neutral solution: 203nm = 55726, 236nm = 43133, 273nm = 3363 - -
Surface tension (mN m-1) 72.39 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) 52.0 A5 Moderately persistent
DT50 (lab at 20oC) 52.0 A5 Moderately persistent
DT50 (field) 8 A5 Non-persistent
DT90 (lab at 20oC) 128.6 A5 -
DT90 (field) 25.8 A5 -
DT50 modelling endpoint 185.0 A5 Worse case -
Note EU 2018 dossier Lab studies DT50 range 9.4-215.2 days, DT90 range 27.8-421 days, Soils=8; Field studies DT50 4.8-9.0 days, DT90 range 18.5-29.8 days; Other sources: DT50 30 days (DW4)
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 1 A5 Non-persistent
Note pH and temperature sensitive: DT50 70 days at pH 5 and 22 degC, 39 days at pH 5 and 25 degC, 0.2 hours at pH 9 and 22 degC, 7 minutes at pH 9 and 25 degC
Water-sediment DT50 (days) 3 A5 Fast
Water phase only DT50 (days) 1.5 A5 Moderately 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 - - -
Koc -
Notes and range -
Freundlich Kf 45.22 A5 Non-mobile
Kfoc 4124
1/n 0.838
Notes and range EU 2018 dossier Kf range 77.39-140.97 mL/g, Kfoc range 1909-5236 mL/g, 1/n range 0.818-0.869, Soils=5
pH sensitivity Yes

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
ethyl 3-hydroxycarbamate This metabolite may cause environmental pollution, click here for further information Soil   0.160   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
phenyl urethane - Soil (anaerobic) - -
aniline
(Ref: )
Note: Major fraction, Relevant
- Soil (anaerobic, photolysis) - -


ECOTOXICOLOGY

for desmedipham

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) 334 A5 Threshold for concern
CT50 (days) 11.2 -
Mammals - Acute oral LD50 (mg kg-1) > 2000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 3 H5 Rat High
(ppm diet) 50 -
Birds - Acute LD50 (mg kg-1) > 2000 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 5000 mg kg feed-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 1.41 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) 0.2 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.35 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.01 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) 1.0 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) > 5.2 A5 Lemna minor, 7 day Moderate
Non-target plants 0.051 A5 Radish
Vegetative vigour
as kg/ha
-
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.01 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.01 A5 Pseudokirchneriella subcapitata Moderate
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Apis mellifera Low
Oral acute 48 hour LD50 (μg bee-1) > 100.6 A5 Apis mellifera Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 79 A5 Eisenia foetida Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 64 A5 Eisenia foetida, 56 days Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 63.8 Mortality LR50
A5 Aphidius rhopalosiphi
-
% Effect 30 Mortality
Fecundity
Dose: 1.17 l ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 194.2 Mortality LR50
A5 Typhlodromus pyri
-
% Effect -28 Reproduction
Dose: 3.0 l ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 1.2 kg ha-1, 100 days
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for desmedipham

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) > 2000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 7.4 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.016 A5 Rat, SF=200 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.05 A5 Dog, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) 0.05 A5 Rat, SF=100 -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.016 A5 Dog, SF=200 -
Dermal penetration studies (%) 1-8 A5 concenteration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded
Occupational 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 May cause dermatitis
Possible thyroid and blood toxicant
EU - Suspected of causing cancer

: 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
CLP classification 2013 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) III - Caution - Slightly toxic
UN Number Usually 307
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for desmedipham

Language Name
English desmedipham
French desmediphame
German Desmedipham
Danish desmedipham
Italian desmedifam
Spanish desmedifam
Greek desmedipham
Slovenian desmedifam
Polish desmedifam
Swedish desmedifam
Hungarian dezmedifam
Dutch desmedifam

Record last updated: Friday 03 May 2019
Contact: aeru@herts.ac.uk