| tribenuron-methyl (Ref: DPX L5300) |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for tribenuron-methyl
Description: A foliar acting, post-emergence herbicide used to control broad-leaved weeds in cereals and other crops
Example pests controlled: Charlock; Chickweed; Red deadnettle; Fat hen; Forget-me-not; Hemp nettle; Mayweed; Common poppy; Redshank; Shepherd's purse
Example applications: Cereals including wheat, barley, triticale, oats; Olives; Sunflower; Grass seed crops; Cotton; Pre-harvest burndown
Efficacy & activity: Efficacy established via field trials and long-term use in the EU.
Availability status: Current
Introduction & key dates: 1987, first approvals
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Sweden/Latvia |
| Date inclusion expires | 31/10/2019 |
| 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 | - |
| Chemical formula | C15H17N5O6S |
| Canonical SMILES | CC1=NC(=NC(=N1)OC)N(C)C(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | VLCQZHSMCYCDJL-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C15H17N5O6S/c1-9-16-13(18-14(17-9)26-4)20(2)15(22)19-27(23,24)11-8-6-5-7-10(11)12(21)25-3/h5-8H,1-4H3,(H,19,22) |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Herbicide | |
| Substance group | Sulfonylurea | |
| Minimum active substance purity | 950 g/kg | |
| Known relevant impurities | EU dossier - None declared | |
| Substance origin | Synthetic | |
| Mode of action | Selective, absorbed through foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS | |
| CAS RN | 101200-48-0 | |
| EC number | 401-190-1 | |
| CIPAC number | 546 | |
| US EPA chemical code | 128887 | |
| PubChem CID | 153909 | |
| Molecular mass (g mol-1) | 395.4 | |
| PIN (Preferred Identification Name) | 2-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylcarbamoyl]sulfamoyl}benzoic acid | |
| IUPAC name | methyl 2-[4-methoxy-6-methyl-1,3,5-triazin-2-yl(methyl)carbamoylsulfamoyl]benzoate | |
| CAS name | methyl 2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl]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 | Many recorded cases Capsella bursa-pastoris Chrysanthemum coronarium Descurainia sophia Galium spurium |
|
| Physical state | White to off-white solid | |
| 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 (may vary with mixtures) | |||
| Formulation and application details | Often supplied as water dispersible or water soluble granules that are mixed with water and used as a spray. | |||
ENVIRONMENTAL FATE
for tribenuron-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 2483 | A5 | High | |
| Solubility - In organic solvents at 20oC (mg l-1) | 20800 | A5 - n-Heptane | - | |
| 250000 | A5 - Dichloromethane | - | ||
| 39100 | L3 - Acetone | - | ||
| 16300 | L3 - Ethyl acetate | - | ||
| Melting point (oC) | 142 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 175 | A4 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.40 X 1000 | Calculated | - |
| Log P | 0.38 | A5 | Low | |
| Bulk density (g ml-1)/Specific gravity | 1.46 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 4.65 | A5 | - | |
| Note: Weak acid | ||||
| Vapour pressure at 20oC (mPa) | 5.99 X 10-06 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.00 X 10-08 | A5 | Non-volatile | |
GUS leaching potential index  |
2.40 | Calculated | Transition state | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.17 X 10-02 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Low | |
| Maximum UV-vis absorption L mol-1 cm-1 | pH 1.66: 200nm=41720, 231nm=20730, 290nm=396.2 pH 7.0: 201nm=37320, 256nm=18040, 290nm=342.4 pH 11.72: 208nm=23760, 256nm=17200, 290nm=334.4 |
A5 | - | |
| Surface tension (mN m-1) | 73.0 | A5 at 20 degC | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | Not readily biodegradable |
| Soil degradation (days) (aerobic) | DT50 (typical) | 9.1 | A5 | Non-persistent |
| DT50 (lab at 20oC) | 9.1 | A5 | Non-persistent | |
| DT50 (field) | 3.6 | A5 | Non-persistent | |
| DT90 (lab at 20oC) | 46.0 | A5 | - | |
| DT90 (field) | 26.1 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU 2018 dossier lab studies DT50 range 2.9-23.1 days, DT90 range 9.7-158 days, Soils=16; field studies DT50 range 1.7-10.4 days, DT90 range 5.8-115 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 | Stable | A5 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | 31.0 | A5 | Moderately persistent |
| Note | pH sensitive: DT50 0.1 days at pH 4@ 20 degC, stable at pH 9 @ 25 degC | |||
| Water-sediment DT50 (days) | 139 | A5 | Slow | |
| Water phase only DT50 (days) | 86.2 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | 1.1 | A5 | Mobile |
| Koc | 35 | |||
| Notes and range | EU 2004 dossier Kd range 0.1-2.1 mL/g, Koc range 8.3-91.0 mL/g, Soils=5 | |||
| Freundlich | Kf | 0.59 | A5 | Mobile |
| Kfoc | 31.6 | |||
| 1/n | 0.98 | |||
| Notes and range | EU 2018 dossier kf range 0.05-1.7, Kfoc range 4.55-74.0 mL/g, 1/n range 0.90-1.11, Soils=10 | |||
| pH sensitivity | Lower sorption at high pH | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| N-methyl triazine amine (Ref: IN-L5296) |
Soil | 0.857 | Major fraction, Relevant | |
| 2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: IN-A4098) |
Soil | 0.126 | Major fraction, Relevant | |
| 1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN-00581) |
Soil | 0.339 | Major fraction, Relevant | |
| tribenuron (Ref: IN-R9803) | Soil | 0.076 | Minor fraction, Relevant | |
| 1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-methylurea (Ref: ) |
Soil | 0.162 | Major fraction, Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| metsulfuron-methyl (Ref: DPX T6376) Note: Major fraction, Relevant |
- | Crops; Livestock; Poultry | - | - |
| (((aminocarbonyl)amino)sulfonyl)benzoate (Ref: IN-B5685) |
sulfonamide urea | Crops; Livestock; Poultry | - | - |
| methyl 2-(((((4-methoxy-6-methyl-1,2,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)4-(beta-D-glucopyranpsyl)benzoate (Ref: IN-B9700) |
- | Crops | - | - |
| 2-(aminosulfonyl)benzoic acid (Ref: IN-D5119) |
- | Crops; Livestock; Poultry | - | - |
| methyl-2-(amonosulfonyl)benzoate (Ref: IN-D5803) |
- | Crops; Livestock; Poultry | - | - |
| methyl 2-(((((4-methoxy-6-methyl-1,2,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)4-hydroxybenzoate (Ref: IN-G7460) |
- | Crops, Livestock | - | - |
| methyl-2(((((4-hydroxy-6-methyl-1,3,5-triazin-2-yl)methylamino)carbonyl)amino)solfonyl)benzoate (Ref: IN-GK521) |
- | Crops; Livestock; Poultry | - | - |
| methyl 2-(((((4-methoxy-6-methyl-1,2,5-triazin-2-yl)methylamino)carbonyl)amino)sulfonyl)benzoate (Ref: IN-GN815) |
- | Crops; Poultry | - | - |
| methyl 2-(((((4-(hyroxymethyl)-6-methoxy-13,5-triazin-2-yl)methylamino)carbonyl)amino)sulfonyl)benzoate (Ref: IN-QKK48) |
- | Crops; Livestock; Poultry | - | - |
ECOTOXICOLOGY
for tribenuron-methyl
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 0.08 | Q2 Estimated | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 12 | B5 Rat | High |
| (ppm diet) | > 100 | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2250 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 974 mg kg bw-1 day-1 | A5 Anas platyrhynchos | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 738 | A5 Oncorhynchus mykiss | Low | |
| Fish - Chronic 21 day NOEC (mg l-1) | 560 | A5 Oncorhynchus mykiss | Low | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 894 | A5 Daphnia magna | Low | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 120 | A5 Daphnia magna | Low | |
| 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) | 0.0099 | B5 Lemna minor | High | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 0.11 | A5 Raphidocelis subcapitata, 120 hour | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | 0.25 | Q2 Unknown species | Moderate | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | - | - | - |
| Oral acute 48 hour LD50 (μg bee-1) | > 9.1 | A5 | Moderate | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | > 98.4 | A5 | Moderate | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| 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 | 14 10 |
Mortality Reproduction Dose: 0.03 kg ha-1 A5 Aphidius rhopalosiphi |
- | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | -3.2 -7 |
Mortality Reproduction Dose: 0.03 kg ha-1 A5 Typhlodromus pyri |
- | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A3 Dose: Not stated |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for tribenuron-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) | > 6.0 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.01 | A5 Rat, 2 year, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.2 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | 0.13 | A5 Rat, SF=167 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.05 | A5 Rat, SF=167 | - | |
| Dermal penetration studies (%) | 25-75 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| 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 | 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 | USEPA - possible human carcinogen Possible liver & spleen toxicant Endocrine issues - Weak estrogenic effect |
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: 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 IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Health: H317, H373 Human: H400, H410 |
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| EC Risk Classification |
Xn - Harmful: R43 | |||
| EC Safety Classification |
S2, S22, S24, S37 | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | III | - | Caution - Slightly toxic | |
| UN Number | Usually 3077 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
TRANSLATIONS
for tribenuron-methyl
| Language | Name |
| English | tribenuron-methyl |
| French | tribenuron-methyle |
| German | Tribenuron |
| Danish | tribenuron-methyl |
| Italian | tribenuron-metile |
| Spanish | tribenuron-metil |
| Greek | - |
| Slovenian | tribenuron-metil |
| Polish | tribenuron metylu |
| Swedish | tribenuronmetyl |
| Hungarian | tribenuron-metil |
| Dutch | - |
Record last updated: Monday 05 November 2018
Contact: aeru@herts.ac.uk