Tribenuron-methyl (Ref: DPX L5300)

Tribenuron-methyl (Ref: DPX L5300)	Last updated: 21/08/2024
(Also known as: tribenuron; metometuron; tribenuron ME)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Drainflow: Mobile	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

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

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/01/2034

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Sweden/Latvia

Date EC 1107/2009 inclusion expires

30/01/2034

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway
✓	✓

Additional information

Also used in

Australia, Morocco

Chemical structure

Isomerism

None

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

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 groups

Sulfonylurea herbicide; Triazinylsulfonylurea herbicide

Minimum active substance purity

950 g kg⁻¹

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

CLP index number

607-177-00-9

Molecular mass

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 Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

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

tribenuron

Formulations

Property

Value

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

AgriGuard
DuPont
Teliton
Nufarm

Example products using this active

Ally Max
Calibre SX
Excalibur
Gex 353
Ratio SX
CDQ SX

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

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

2483

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

20800

n-Heptane

250000

Dichloromethane

39100

Acetone

16300

Ethyl acetate

Melting point (°C)

142

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

175

Flashpoint (°C)

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

2.63 X 10⁰⁰

Calculated

Log P

0.42

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.46

Dissociation constant pKa) at 25 °C

4.65

Weak acid

Vapour pressure at 20 °C (mPa)

5.99 X 10^-06

Low volatility

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

1.00 X 10^-10

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Surface tension (mN m⁻¹)

73.0

at 20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

9.1

Non-persistent

DT₅₀ (lab at 20 °C)

9.1

Non-persistent

DT₅₀ (field)

3.6

Non-persistent

DT₉₀ (lab at 20 °C)

46.0

Moderately persistent

DT₉₀ (field)

26.1

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 (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) 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

31.0

Moderately persistent

Note

pH sensitive: DT₅₀ 0.1 days at pH 4at 20 °C, stable at pH 9 at 25 °C

Water-sediment DT₅₀ (days)

139

Slow

Water phase only DT₅₀ (days)

86.2

Stable

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

1.1

Mobile

K_oc (mL g⁻¹)

Notes and range

EU 2004 dossier K_d range 0.1-2.1 mL g⁻¹, K_oc range 8.3-91.0 mL g⁻¹, Soils=5

Freundlich

K_f (mL g⁻¹)

0.59

Mobile

K_foc (mL g⁻¹)

31.6

¹/_n

0.98

Notes and range

EU 2018 dossier kf range 0.05-1.7, K_foc range 4.55-74.0 mL g⁻¹, ¹/_n range 0.90-1.11, Soils=10

pH sensitivity

Lower sorption at high pH

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.39

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

3.15 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

43.4

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

0.08

Estimated

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

tribenuron (Ref: IN R9803)

Minor fraction

0.076

1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-methylurea

Major fraction

0.162

N-methyl triazine amine (Ref: IN L5296)

Major fraction

0.857

2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: CGA 150829)

Major fraction

0.126

1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN 00581)

Major fraction

0.339

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: CGA 150829)

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

methyl 2-(((((4-methoxy-6-methyl-1,2,5-triazin-2-yl)methylamino)carbonyl)amino)sulfonyl)benzoate (Ref: IN-GN815)

Plant; 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)

Plant

methyl 2-(((((4-methoxy-6-methyl-1,2,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)4-hydroxybenzoate (Ref: IN-G7460)

Plant; Livestock

methyl-2-(amonosulfonyl)benzoate (Ref: IN-D5803)

Plant; Livestock; Poultry

2-(aminosulfonyl)benzoic acid (Ref: IN-D5119)

Plant; Livestock; Poultry

(((aminocarbonyl)amino)sulfonyl)benzoate (Ref: IN-B5685)

sulfonamide urea

Plant; Livestock; Poultry

metsulfuron-methyl (Ref: DPX T6376)

Plant; Livestock; Poultry

methyl-2(((((4-hydroxy-6-methyl-1,3,5-triazin-2-yl)methylamino)carbonyl)amino)solfonyl)benzoate (Ref: IN-GK521)

Plant; Livestock; Poultry

methyl 2-(((((4-(hyroxymethyl)-6-methoxy-13,5-triazin-2-yl)methylamino)carbonyl)amino)sulfonyl)benzoate (Ref: IN-QKK48)

Plant; Livestock; Poultry

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 12

Rat

High

(ppm diet)

> 100

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

> 75

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 974 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Anas platyrhynchos NOEL

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

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

3.2

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: Not stated

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

30.8

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 98.4

Apis mellifera

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 9.1

Apis mellifera

Moderate

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

74.3

Apis mellifera

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as Mortality 12-day LR₅₀ g ha⁻¹

> 30

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 30

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 30

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ g ha⁻¹

> 30

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

738

Oncorhynchus mykiss

Low

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

560

Oncorhynchus mykiss

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

894

Daphnia magna

Low

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

120

Daphnia magna

Low

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

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

Lemna minor

High

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

0.11

Raphidocelis subcapitata 120 hr

Moderate

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

0.25

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

> 5000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 6.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.01

Rat as tribenuron

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

0.2

Rat as tribenuron

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

0.13

Rat SF=167

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.05

Rat as tribenuron

Dermal penetration studies (%)

25-75

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

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

US EPA - possible human carcinogen
Possible liver & spleen toxicant
Endocrine issues - Weak estrogenic effect

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317, H373
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

tribenuron-methyl

French

tribenuron-methyle

German

Tribenuron

Danish

tribenuron-methyl

Italian

tribenuron-metile

Spanish

tribenuron-metil

Greek

Polish

tribenuron metylu

Swedish

tribenuronmetyl

Hungarian

tribenuron-metil

Dutch

Norwegian

tribenuron-metyl

Record last updated:	21/08/2024
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