Desmedipham (Ref: EP 475)

Desmedipham (Ref: EP 475)	Last updated: 12/01/2021
(Also known as: DMP; desmediphame)

SUMMARY

Desmedipham is a post-emergence herbicide that is no longer 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

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

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Finland/Denmark

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Also used in

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⁻¹

Known relevant impurities

EU dossier - Toluene <2g kg⁻¹; 3-aminophenol <1g kg⁻¹; Aniline < 0.5 g kg⁻¹

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

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; Currently being phased out in the EU.

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

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

Betana Carrera
Betanal Expert
Alphanex
Venzar Flowable

Example products using this active

AgriGuard
Bayer CropScience
Landgold
King Tech

Formulation and application details

Usually supplied as an emulsifiable concentrate.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

5.6

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Hexane

1200

Toluene

187000

Methanol

285000

Acetone

Melting point (°C)

118.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

295

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

Octanol-water partition coefficient at pH 7, 20 °C

5.01 X 10⁰²

Calculated

Log P

2.7

Moderate

Bulk density (g ml⁻¹)

1.32

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.0 X 10^-05

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

5.40 X 10^-07

Non-volatile

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral solution: 203nm = 55726, 236nm = 43133, 273nm = 3363

Surface tension (mN m⁻¹)

72.39

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

52.0

Moderately persistent

DT₅₀ (lab at 20 °C)

52.0

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

128.6

Persistent

DT₉₀ (field)

25.8

DT₅₀ modelling endpoint

185.0

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

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Non-persistent

Note

pH and temperature sensitive: DT₅₀ 70 days at pH 5 and 22 °C, 39 days at pH 5 and 25 °C, 0.2 hours at pH 9 and 22 °C, 7 minutes at pH 9 and 25 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

1.5

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

45.22

Non-mobile

K_foc

4124

¹/_n

0.838

Notes and range

EU 2018 dossier K_f range 77.39-140.97 mL g⁻¹, K_foc range 1909-5236 mL g⁻¹, ¹/_n range 0.818-0.869, Soils=5

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.35

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

6.63 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

aniline

Soil (anaerobic, photolysis)

phenyl urethane

Soil (anaerobic)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

334

Threshold for concern

CT₅₀ (days)

11.2

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Rat Reproductive NOAEL

High

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Anas platyrhynchos NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1.41

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.2

Oncorhynchus mykiss

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.35

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.01

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

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

Lemna minor 7 day

Moderate

Non-target plants

0.051

Radish
Vegetative vigour
as kg ha⁻¹

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.01

Raphidocelis subcapitata

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

0.01

Pseudokirchneriella subcapitata

Moderate

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Apis mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100.6

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 100

Bombus mellifera

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 79

Eisenia foetida

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Eisenia foetida 56 days

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

158

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

63.8

Mortality LR₅₀
Aphidius rhopalosiphi

% Effect

Mortality / Fecundity [Dose: 1.17 l ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

194.2

Mortality LR₅₀
Typhlodromus pyri

% Effect

-28

Reproduction [Dose: 3.0 l ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 1.2 kg ha⁻¹ 100 days

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 7.4

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.016

Rat SF=200

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.05

Dog SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

0.05

Rat SF=100

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.016

Dog SF=200

Dermal penetration studies (%)

1-8

concenteration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

PPE/PPC recommended

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl 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

Handling issues

Property

Value and 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)

UN Number

Usually 307

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

desmedipham

French

desmediphame

German

Desmedipham

Danish

desmedipham

Italian

desmedifam

Spanish

desmedifam

Greek

desmedipham

Polish

desmedifam

Swedish

desmedifam

Hungarian

dezmedifam

Dutch

desmedifam

Record last updated:	12/01/2021
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242