| carbetamide (Ref: RP 11561) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
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 
for carbetamide
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
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | France |
| Date inclusion expires | 31/05/2021 |
| 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 |
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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) |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |||
| Substance group | Carbamate | |||
| Minimum active substance purity | 930 g/kg | |||
| 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 | 95 | |||
| US EPA chemical code | 259200 | |||
| PubChem CID | 27689 | |||
| Molecular mass (g mol-1) | 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) | K2 | |||
| Herbicide Resistance Classification (WSSA) | 23 | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | - | |||
| Physical state | Colourless crystalline powder | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | None | |||
| Formulation and application details | Usually supplied as a wettable granules or powders that are mixed with water and applied as a spray. | |||
ENVIRONMENTAL FATE
for carbetamide
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 3270 | A4 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 250000 | A5 - Acetone | - | |
| 250000 | A5 - Dichloroethane | - | ||
| 250000 | A5 - Ethyl acetate | - | ||
| 10000 | A5 - n-Heptane | - | ||
| Melting point (oC) | 109 | A5 | - | |
| Boiling point (oC) | 235 | A5 | - | |
| Degradation point (oC) | 400 | A4 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 6.03 X 1001 | Calculated | - |
| Log P | 1.78 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.18 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 11.3 | A5 | - | |
| Note: Very weak acid | ||||
| Vapour pressure at 20oC (mPa) | 0.0003 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.93 X 10-08 | A5 | Non-volatile | |
GUS leaching potential index  |
2.13 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.61 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | 205.8nm = 104.5, 234.8nm = 104.30, 295nm < 10 | A5 | - | |
| Surface tension (mN m-1) | 68.6 | A5 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 12.4 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 10.9 | A5 | Non-persistent | |
| DT50 (field) | 8 | Y4 | Non-persistent | |
| DT90 (lab at 20oC) | 49.3 | A5 | - | |
| 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 | A5 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 19 | A5 | Non-persistent |
| Note | Stable pH 3 to pH 6, DT50 21 days at pH 9, 25 degC and 7 days at pH 9, 35 degC | |||
| Water-sediment DT50 (days) | 55.5 | A5 | Moderately fast | |
| Water phase only DT50 (days) | 9.1 | A5 | Moderately fast | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 1.38 | A5 | Moderately mobile |
| Kfoc | 88.6 | |||
| 1/n | 0.93 | |||
| Notes and range | EU dossier Kf range 0.67-1.86, Kfoc range 59.5-118.2 mL/g, 1/n range 0.88-1.00, Soils=4 | |||
| pH sensitivity | No | |||
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 |
| (Ref: RP 10810) | - | Soil; Water | - | - |
| 3-(4-hydroxyphenyl)-5-methyl-oxazolidine-2,4-dione (Ref: RP 12913) |
- | Plant; Soil; Water | - | - |
| N-(4-hydroxyphenyl)-(ethylcarbamoyl-1)ethylcarbamate (Ref: RP 29835) |
- | Rat (Urinary); Plant | - | - |
| 3-(4-hydroxyphenyl)-5-methyl-1,13-oxazolidine-2,4-dione (Ref: RP 29992) |
- | Rat (Urinary); Soil | - | - |
| (Ref: RP 39791) | - | Soil | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | Q3 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | 1718 | A5 Rat | Moderate | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 203 | B5 Rat | Moderate |
| (ppm diet) | > 2000 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 1044 mg kg bw-1 day-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 100 | A5 Oncorhynchus mykiss | Low | |
| Fish - Chronic 21 day NOEC (mg l-1) | > 100 | A5 Oncorhynchus mykiss | Low | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 81 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 1.0 | 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) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 301 | A5 Lemna minor | Low | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 158 | A5 Scenedemus subspicatus | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.14 | Q2 Unknown species | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 63.22 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 660 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | -5.3 | Mortality Dose: 3.0 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | -3.2 | Mortality Dose: 3.0 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | - | - | - | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for carbetamide
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) | 1718 | A5 Rat | Moderate | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | 0.13 | L3 Rat | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.06 | A5 2yr Rat, SF=1000 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.3 | A5 Dog, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.12 | A4 90d Dog, SF=100 | - | |
| Dermal penetration studies (%) | 0.2-9.4 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Acceptable risk to bystanders for propsed uses | ||
| Occupational | Potential risk to operators - PPE/PPC necessary Low risk for other farm workers |
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| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | 0.1 | EU Dir 89/778/EC limit; A5 Calc MAC=64.0 μg l-1 | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Possible liver and thyroid toxicant | |||||||
: 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 |
Prevent generation of dust Not explosive |
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| CLP classification 2013 | Health: H319, H351, H360d Environment: H411 |
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| EC Risk Classification |
Carcinogen category 3: R40 Reproduction risk category 3: R63 N - Dangerous for the environment: R52, R53 |
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| EC Safety Classification |
S22, S26, S36, S45 | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | IV | - | Caution - Not acutely toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | carbetamide |
| French | carbetamide |
| German | Carbetamid |
| Danish | carbetamid |
| Italian | carbetamide |
| Spanish | carbetamida |
| Greek | - |
| Slovenian | karbetamid |
| Polish | karbetamid |
| Swedish | - |
| Hungarian | carbamid |
| Dutch | carbetamide |
Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk