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

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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
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:

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:

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:

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	ethofumesate phenmedipham chloridazon

Formulations:

Property	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		Value	Source/Quality Score/Other Information	Interpretation
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		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	Value	1.26 X 10-02	Calculated	-
	Note	-
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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
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
ethyl 3-hydroxycarbamate		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		Value	Source/Quality Score/Other Information	Interpretation
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		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (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		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising
CLP classification 2013		Environment: H400, H410
EC Risk Classification		N - Dangerous for the environment: R50, R53
EC Safety Classification		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		-

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

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Record last updated: Thursday 23 August 2018
Contact: aeru@herts.ac.uk