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tribenuron-methyl (Ref: DPX L5300)
** tribenuron ** metometuron ** tribenuron ME ** Translations

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GENERAL INFORMATION Click here for an explantaion of the general chemical status 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: Click to access a note on the approvals information on this site

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: Click here for further information on the general chemical status information used on this site
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: Click here for further information on the general chemical status information used on this site
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 Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • AgriGuard
  • DuPont
  • Teliton
Example products using this active
  • Ally Max
  • Calibre SX
  • Excalibur
  • Gex 353
  • Ratio SX
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 Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
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 Click here for a note on the limitations of the GUS 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 Click here for a note on the limitations of the SCI-GROW index Value 4.17 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the 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 Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
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 Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
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 Click here for further information on 1107/2009 relevancy
N-methyl triazine amine (Ref: IN-L5296) This metabolite may cause environmental pollution, click here for further information Soil   0.857   Major fraction, Relevant
2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: IN-A4098) This metabolite may cause environmental pollution, click here for further information Soil   0.126   Major fraction, Relevant
1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN-00581) This metabolite may cause environmental pollution, click here for further information 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: ) This metabolite may cause environmental pollution, click here for further information 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 Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
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 Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the 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

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

General human health issues USEPA - possible human carcinogen
Possible liver & spleen toxicant
Endocrine issues - Weak estrogenic effect

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H317, H373
Human: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R43
EC Safety Classification Click here to view information omn the EU safety phrases 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 Click here for a description of UN packaging marks 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
© University of Hertfordshire