| mesosulfuron-methyl (Ref: AE F130060) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for mesosulfuron-methyl
Description: A systemic herbicide used for post-emergence control of grasses and other weeds in cereals
Example pests controlled: Grasses including blackgrass; Broad-leaved weeds
Example applications: Cereals including spring wheat, winter wheat, durum wheat, winter rye
Efficacy & activity: -
Availability status: Current
Introduction & key dates: circa 2001
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | France/Poland |
| Date inclusion expires | 30/06/2032 |
| 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 |
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
Also used in: Australia
Chemical structure:
| Isomerism | - |
| Chemical formula | C17H21N5O9S2 |
| Canonical SMILES | COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C2=C(C=CC(=C2)CNS(=O)(=O)C)C(=O)OC)OC |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | NIFKBBMCXCMCAO-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C17H21N5O9S2/c1-29-13-8-14(30-2)20-16(19-13)21-17(24)22-33(27,28)12-7-10(9-18-32(4,25)26)5-6-11(12)15(23)31-3/h5-8,18H,9H2,1-4H3,(H2,19,20,21,22,24)/f/h21-22H |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |
| Substance group | Sulfonylurea | |
| Minimum active substance purity | >955 g/kg | |
| Known relevant impurities | EU dossier: None disclosed | |
| Substance origin | Synthetic | |
| Mode of action | Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS | |
| CAS RN | 208465-21-8 | |
| EC number | - | |
| CIPAC number | 663.201 | |
| US EPA chemical code | 122009 | |
| PubChem CID | 11409499 | |
| Molecular mass (g mol-1) | 503.51 | |
| PIN (Preferred Identification Name) | methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-a-(methanesulfonamido)-p-toluate | |
| IUPAC name | methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-a-(methanesulfonamido)-p-toluate | |
| CAS name | methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]methyl]benzoate | |
| Other status information | - | |
| Relevant Environmental Water Quality Standards | - | |
| Herbicide Resistance Classification (HRAC) | B | |
| Herbicide Resistance Classification (WSSA) | 2 | |
| Insecticide Resistance Classification (IRAC) | Not applicable | |
| Fungicide Resistance Classification (FRAC) | Not applicable | |
| Examples of recorded resistance | Alopecurus myosuroides | |
| Physical state | Pale yellow crystalline solid | |
| Related substances & organisms | ||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
|
|||
| Example products using this active |
|
|||
| UK LERAP status | Buffer probably required in UK - see product label | |||
| Formulation and application details | Often supplied as an oil suspension. | |||
ENVIRONMENTAL FATE
for mesosulfuron-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 483 | A5 | Moderate | |
| Solubility - In organic solvents at 20oC (mg l-1) | 200 | L3 - Hexane | - | |
| 13660 | L3 - Acetone | - | ||
| 2000 | L3 - Ethyl acetate | - | ||
| 130 | L3 - Toluene | - | ||
| Melting point (oC) | 195.4 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 190 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 3.31 X 10-01 | Calculated | - |
| Log P | -0.48 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.48 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 4.35 | A5 | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 1.10 X 10-05 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 3.65 X 10-12 | A5 | Non-volatile | |
GUS leaching potential index  |
3.34 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.53 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | 203nm = 53566, 237nm = 22220, 291nm = 904 | A5 | - | |
| Surface tension (mN m-1) | 61.9 | A5 at 20 degC, 19.27 mg l-1 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 43.5 | A5 | Moderately persistent |
| DT50 (lab at 20oC) | 43.5 | A5 | Moderately persistent | |
| DT50 (field) | 78 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 345.5 | A5 | - | |
| DT90 (field) | 257 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU 2016 dossier Lab studies DT50 range 7.6-140.1 days, DT90 range 25.3- >1000 days, Soils=9 | |||
| 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 | 46 | A5 | Stable |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 253 | A5 | Persistent |
| Note | pH and temperature sensitive: DT50 7.2 days at pH 5 and 20 degC, 3.5 days at pH 5 and 25 degC, 253 days at pH 7 and 25 deg C, 23 days at pH 7 and 40 degC, 318 days at pH 9 and 25 deg C, 27 dats at pH 9 and 40 degC | |||
| Water-sediment DT50 (days) | 48.9 | A5 | Moderately fast | |
| Water phase only DT50 (days) | 44 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 1.27 | A5 | Moderately mobile |
| Kfoc | 92 | |||
| 1/n | 0.91 | |||
| Notes and range | EU dossier Kf 0.24-3.71 ml/g; Kfoc range 26-345 mL/g; 1/n range 0.85-0.93; Soils=9 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| 2-amino-4,6-dimethoxypyrimidine (Ref: AE-F092944) |
Soil | 0.101 | Major fraction, Relevant | |
| 4,6-dimethoxypyrimidine-2-yl-urea (Ref: AE-F099095) |
Soil | 0.292 | Major fraction, Relevant | |
| mesosulfuron (Ref: AE F154851) |
Soil | 0.162 | Major fraction, RelevancT | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| benzisothiazole (Ref: AE F147447) |
- | Water (Hydrolysis); Water/sediment | 0.374 | - |
| O-desmethyl mesosulfuron (Ref: AE F160459) |
- | a = Soil (Anaerobic); b = Water/sediment | a=0.259 | - |
ECOTOXICOLOGY
for mesosulfuron-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | Low risk | A5 Based on LogP < 3 | Low potential |
| CT50 (days) | - | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Anas platyrhynchos | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5000 mg kg feed-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) | 32.0 | A5 Oncorhynchus mykiss | Low | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 100 | A5 Daphnia magna | Low | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 1.8 | 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) | 0.00062 | C4 Lemna gibba | High | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.2 | A5 Raphidocelis subcapitata | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 13 | A5, 72 hr | Moderate |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | 5.6 | A5, 72 hr | 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) | > 100 | R3 Bombus terrestris | 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) | > 1000 | C4 Eisenia foetida | Low | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 150 | A3 Eisenia foetida, 56 days, g ha-1 | Low | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | 17.5 | Mortality Dose: 15 g ha-1 A5 Aphidius rhopalosiphi, adult |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | 8.3 | Mortality Dose: 15 g ha-1 A5 Typhlodromus pyri, protonymph |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 0.075 kg ha-1 |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for mesosulfuron-methyl
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) | > 5000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 1.33 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 1.0 | A5 Mouse, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.2 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 9.3-13.9 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | No unacceptable risks to bystanders identified | ||
| Occupational | No unacceptable risks to operators or other workers identified | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
|
A3; B0; C0; D0; E3 |
|
|
|
|
|||
| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
|
|
|
|
|
|
|||
| General human health issues | No further information available | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : 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 | |||
| EC Risk Classification |
N - Dangerous for the environment: R50/53 | |||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for mesosulfuron-methyl
| Language | Name |
| English | mesosulfuron-methyl |
| French | mesosulfuron-methyle |
| German | Mesosulfuron |
| Danish | mesosulfuron |
| Italian | mesosulfuron-metile |
| Spanish | mesosulfuron-metil |
| Greek | - |
| Slovenian | mesosulfuron metil |
| Polish | mezosulfuron metylowy |
| Swedish | mesosulfuronmetyl |
| Hungarian | - |
| Dutch | - |
Record last updated: Tuesday 04 June 2019
Contact: aeru@herts.ac.uk