Carbetamide (Ref: RP 11561)

Carbetamide (Ref: RP 11561)	Last updated: 31/10/2024
(Also known as: carbetamid)

SUMMARY

Carbetamide is pre-and post-emergence carbanilate herbicide. It is highly soluble in water and is relatively volatile. It is moderately toxic to mammals and has a high potential for bioaccumulation. It is a potential carcinogen. Carbetamide has a moderate toxicity to birds, fish, aquatic invertebrates and earthworms. It shows a low toxicity to honeybees, aquatic plants and algae.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A pre- and post-emergence herbicide to control annual grasses and some broad-leaved weeds

Example pests controlled

Blackgrass; Ryegrass; Common chickweed; Speedwell; Meadowgrass; Forget-me-not; Red deadnettle; Mayweed

Example applications

Oilseed rape; Vegetables including beans, brassicas, root crops; Lucerne; Grapes

Efficacy & activity

Availability status

Current

Introduction & key dates

2000, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Australia

Chemical structure

Isomerism

A chiral molecule

Chemical formula

C₁₂H₁₆N₂O₃

Canonical SMILES

CCNC(=O)C(C)OC(=O)NC1=CC=CC=C1

Isomeric SMILES

CCNC(=O)[C@@H](C)OC(=O)NC1=CC=CC=C1

International Chemical Identifier key (InChIKey)

AMRQXHFXNZFDCH-SECBINFHSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H16N2O3/c1-3-13-11(15)9(2)17-12(16)14-10-7-5-4-6-8-10/h4-9H,3H2,1-2H3,(H,13,15)(H,14,16)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Carbanilate herbicide

Minimum active substance purity

930 g kg⁻¹

Known relevant impurities

EU dossier - water, volatiles and acetone insolubles

Substance origin

Synthetic

Mode of action

Selective absorbed by roots with some residual activity. Mitosis inhibitor.

CAS RN

16118-49-3

EC number

240-286-6

CIPAC number

US EPA chemical code

259200

PubChem CID

27689

CLP index number

616-223-00-7

Molecular mass

236.27

PIN (Preferred Identification Name)

(2R)-1-(ethylamino)-1-oxopropan-2-yl phenylcarbamate

IUPAC name

(R)-1-(ethylcarbamoyl)ethyl carbanilate

CAS name

(2R)-N-ethyl-2-[[(phenylamino)carbonyl]oxy]propanamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Colourless crystalline powder

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Makhteshim-Agan
Fenchemie
Rhone-Poulenc
May & Baker

Example products using this active

Carbetamex
Crawler
Riot
Scrum
Legurame

Formulation and application details

Usually supplied as a wettable granules or powders that are mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3270

High

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

250000

Acetone

250000

Dichloroethane

250000

Ethyl acetate

10000

n-Heptane

Melting point (°C)

109

Boiling point (°C)

235

Degradation point (°C)

400

Flashpoint (°C)

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

6.03 X 10⁰¹

Calculated

Log P

1.78

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

11.3

Very weak acid

Vapour pressure at 20 °C (mPa)

3.0 X 10^-04

Low volatility

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

1.93 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

205.8nm = 104.5, 234.8nm = 104.30, 295nm < 10

Surface tension (mN m⁻¹)

68.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

12.4

Non-persistent

DT₅₀ (lab at 20 °C)

10.9

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

49.3

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4.02-28.9 days, DT₉₀ range 11.2-133.5 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

Stable pH 3 to pH 6, DT₅₀ 21 days at pH 9, 25 °C and 7 days at pH 9, 35 °C

Water-sediment DT₅₀ (days)

55.5

Moderately fast

Water phase only DT₅₀ (days)

9.1

Moderately fast

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

1.38

Moderately mobile

K_foc (mL g⁻¹)

88.6

¹/_n

0.93

Notes and range

EU dossier K_f range 0.67-1.86, K_foc range 59.5-118.2 mL g⁻¹, ¹/_n range 0.88-1.00, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.85

Calculated

Transition state

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

Value

1.99 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

2.15

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

2-hydroxy-N-phenylpropanamide (Ref: RP 39791)

3-(4-hydroxyphenyl)-5-methyl-1,13-oxazolidine-2,4-dione (Ref: RP 29992)

(RS)2-phenylcarbamoyl-propionic acid

Major fraction

0.165

3-(4-hydroxyphenyl)-5-methyl-oxazolidine-2,4-dione (Ref: RP 12913)

2-(phenylcarbamoyloxy)propanoylcarbamic acid (Ref: RP 10810)

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

(RS)2-phenylcarbamoyl-propionic acid

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

3-(4-hydroxyphenyl)-5-methyl-oxazolidine-2,4-dione (Ref: RP 12913)

Plant; Surface water

2-(phenylcarbamoyloxy)propanoylcarbamic acid (Ref: RP 10810)

Water

N-(4-hydroxyphenyl)-(ethylcarbamoyl-1)ethylcarbamate (Ref: RP 29835)

Rat (Urine); Plant

3-(4-hydroxyphenyl)-5-methyl-1,13-oxazolidine-2,4-dione (Ref: RP 29992)

Rat (Urine)

(RS)2-phenylcarbamoyl-propionic acid

carbetamide-COOH

Surface water; Sediment

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1718

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 203

Rat

Moderate

(ppm diet)

> 2000

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

208

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1044 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

169

Coturnix japonica

Moderate

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

660

Eisenia foetida

Moderate

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

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

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)

> 63.22

Apis mellifera

Moderate

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

Chronic

Notes

Bumblebees (Bombus 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)

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 bee species (1)

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

Mode of exposure

Other bee species (2)

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

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 3015

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 3015

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

Daphnia magna

Moderate

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

1.0

Daphnia magna

Moderate

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

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)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

301

Lemna minor

Low

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

158

Scenedesmus subspicatus

Low

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

0.14

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

1718

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.13

Rat

Other Mammal toxicity endpoints

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

0.06

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

0.3

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

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

0.12

Dermal penetration studies (%)

0.2-9.4

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risk to bystanders for propsed uses

Occupational

Potential risk to operators - PPE/PPC necessary
Low risk for other farm workers

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=64.0 µg l⁻¹

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and thyroid toxicant
CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H351, H360D
Environment: H411

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

carbetamide

French

carbetamide

German

Carbetamid

Danish

carbetamid

Italian

carbetamide

Spanish

carbetamida

Greek

Polish

karbetamid

Swedish

Hungarian

carbamid

Dutch

carbetamide

Norwegian

Record last updated:	31/10/2024
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