Carbetamide (Ref: RP 11561)

Carbetamide (Ref: RP 11561)	Last updated: 12/01/2021
(Also known as: carbetamid)

SUMMARY

Carbetamide is pre-and post-emergence carbamate herbicide that is approved for use in the EU. 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.

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

31/05/2021

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

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 group

Carbamate

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

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 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 crystalline powder

Formulations

Property

Value

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

Carbetamex
Crawler
Riot
Scrum
Legurame

Example products using this active

Makhteshim-Agan
Fenchemie
Rhone-Poulenc
May & Baker

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)

Not expected to self ignite; Not highly flammable

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

6.03 X 10⁰¹

Calculated

Log P

1.78

Low

Bulk density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

11.3

Very weak acid

Vapour pressure at 20 °C (mPa)

0.0003

Low volatility

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

1.93 X 10^-08

Non-volatile

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 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

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

1.38

Moderately mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(RS)2-phenylcarbamoyl-propionic acid

Soil

0.165

Relevant, Major fraction

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Rat (Urinary); Soil

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

Plant; Soil; Water

Ref: RP 10810

Soil; Water

Ref: RP 39791

Soil

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

Rat (Urinary); Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

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

Daphnia magna

Moderate

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

1.0

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)

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

Non-target plants

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

158

Scenedemus subspicatus

Low

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

0.14

Unknown species

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)

> 63.22

Apis mellifera

Moderate

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)

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)

660

Eisenia foetida

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

-5.3

Mortality [Dose: 3.0 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-3.2

Mortality [Dose: 3.0 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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)

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

2yr Rat SF=1000

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

0.3

Dog SF=100

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

90d Dog SF=100

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

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

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

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive

CLP classification 2013

Health: H302, H351, H360D
Environment: H411

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R63
N - Dangerous for the environment: R52, R53

EC Safety Classification

S22, S26, S36, S45

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

carbetamide

French

carbetamide

German

Carbetamid

Danish

carbetamid

Italian

carbetamide

Spanish

carbetamida

Greek

Polish

karbetamid

Swedish

Hungarian

carbamid

Dutch

carbetamide

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