Tribenuron-methyl (Ref: DPX L5300)

Tribenuron-methyl (Ref: DPX L5300)	Last updated: 08/11/2019
(Also known as: tribenuron; metometuron; tribenuron ME)

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/01/2034

UK LERAP status

None (may vary with mixtures)

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

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⁻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

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 Classification (HRAC)

Herbicide Resistance Classification (WSSA)

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

flupyrsulfuron-methyl-sodium

fluroxypyr

thifensulfuron-methyl

metsulfuron-methyl

tribenuron

Formulations

Property

Value

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

Ally Max
Calibre SX
Excalibur
Gex 353
Ratio SX

Example products using this active

AgriGuard
DuPont
Teliton

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)

Not expected to self ignite; Not highly flammable

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

2.40 X 10⁰⁰

Calculated

Log P

0.38

Low

Bulk 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^-08

Non-volatile

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

1.1

Mobile

K_oc

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

0.59

Mobile

K_foc

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

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

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)

Crops; Livestock; Poultry

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

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-methoxy-6-methyl-1,2,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)4-(beta-D-glucopyranpsyl)benzoate (Ref: IN-B9700)

Crops

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

Crops; Livestock; Poultry

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

Crops; Livestock; Poultry

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

sulfonamide urea

Crops; Livestock; Poultry

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

0.08

Estimated

Low potential

CT₅₀ (days)

Not available

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)

Colinus virginianus Anas platyrhynchos NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

738

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

560

Oncorhynchus mykiss

Low

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

894

Daphnia magna

Low

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

120

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

Lemna minor

High

Non-target plants

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

0.11

Raphidocelis subcapitata 120 hour

Moderate

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

0.25

Unknown species

Moderate

Honeybees (Apis 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)

> 9.1

Apis mellifera

Moderate

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

> 98.4

Apis mellifera

Moderate

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 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

Eisenia foetida

Low

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

3.2

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

30.8

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

14 / 10

Mortality / Reproduction [Dose: 0.03 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-3.2 / -7

Mortality / Reproduction [Dose: 0.03 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: Not stated

Mesocosm study data

NOEAEC mg l⁻¹

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 2 year SF=100

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

0.2

Rat SF=100

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 SF=167

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

USEPA - 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 Code is usually 9

CLP classification 2013

Health: H317, H373
Human: H400, H410

EC Risk Classification

Xn - Harmful: R43

EC Safety Classification

S2, S22, S24, S37

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

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

Record last updated:	08/11/2019
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