Triflusulfuron-methyl (Ref: DPX 66037)

Triflusulfuron-methyl (Ref: DPX 66037)	Last updated: 22/08/2024
(Also known as: triflusulfuron; IN 66037; T 478)

SUMMARY

Triflusulfuron-methyl is a s ulfonylurea herbicide. It is moderately soluble in water and has a low volatility. It is not expected to be persistent in soil systems but may be persistent in water depending on local conditions. It is not expected to leach to groundwater. Whilst its toxicity to aquatic plants is high, toxicity to most other species is moderate to low. Triflusulfuron-methyl has a low oral mammalian toxicity and is thought to be a respiratory tract irritant. It is possible that this substance is carcinogenic.

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; Fish chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Possible Carcinogen; Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A post-emergence herbicide for the control many annual and perennial broad-leaved weeds

Example pests controlled

Black bindweed; Charlock; Chickweed; Cleavers; Fathen; Field pansy; Fools parsley, Knotgrass; Redshank; Volunteer rape

Example applications

Sugarbeet; Fodder beet; Red beet; Mangolds; Chicory

Efficacy & activity

Triflusulfuron based products have been registered in many EU countries based on detailed national assessments of the efficacy package.

Availability status

Current

Introduction & key dates

1992, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2028

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France/Denmark

Date EC 1107/2009 inclusion expires

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

Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₇H₁₉F₃N₆O₆S

Canonical SMILES

CC1=CC=CC(=C1S(=O)(=O)NC(=O)NC2=NC(=NC(=N2)OCC(F)(F)F)N(C)C)C(=O)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IMEVJVISCHQJRM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H19F3N6O6S/c1-9-6-5-7-10(12(27)31-4)11(9)33(29,30)25-15(28)22-13-21-14(26(2)3)24-16(23-13)32-8-17(18,19)20/h5-7H,8H2,1-4H3,(H2,21,22,23,24,25,28)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
triflusulfuron-methyl	-

General status

Pesticide type

Herbicide

Substance groups

Sulfonylurea herbicide; Triazinylsulfonylurea herbicide

Minimum active substance purity

96%

Known relevant impurities

EU dossier - N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine <10/g kg⁻¹; Dimethylcarbomoyl chloride may also be present ~1.7 ppm.

Substance origin

Synthetic

Mode of action

CAS RN

126535-15-7

EC number

603-146-9

CIPAC number

731.201

US EPA chemical code

129002

PubChem CID

92434

CLP index number

607-714-00-7

Molecular mass

492.43

PIN (Preferred Identification Name)

methyl 2-({[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)-3-methylbenzoate

IUPAC name

methyl 2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoylsulfamoyl]-m-toluate

CAS name

methyl 2-[[[[[4-(dimethylamino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]amino]carbonyl]amino]sulfonyl]-3-methylbenzoate

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

Physical state

White crystalline solid

Related substances & organisms

triflusulfuron

Formulations

Property

Value

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

DuPont

Example products using this active

Debut
Upbeet
Safari

Formulation and application details

Often supplied as water dispersible 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)

260

at 25 °C

Moderate

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

27000

Ethyl acetate

120000

Acetone

1.6

Hexane

17000

Methanol

Melting point (°C)

159

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

159

Flashpoint (°C)

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

8.71 X 10⁰⁰

Calculated

Log P

0.94

at 25 °C

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.46

Dissociation constant pKa) at 25 °C

4.4

Weak acid, 25 DegC

Vapour pressure at 20 °C (mPa)

1.01 X 10^-02

Low volatility

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

1.91 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Acidic soln: 228nm=40300, 291nm=981
Neutral soln: 235nm=51700, 291nm=474
Basic soln: 235nm=51700, 291nm=481

Surface tension (mN m⁻¹)

67.92

at 20°C 98.9%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

14.6

Non-persistent

DT₅₀ (lab at 20 °C)

14.6

Non-persistent

DT₅₀ (field)

4.5

Non-persistent

DT₉₀ (lab at 20 °C)

48.4

Moderately persistent

DT₉₀ (field)

16.9

DT₅₀ modelling endpoint

6.1

normalised geometric mean

Note

EU 2019 RAR dossier lab studies (measured) DT₅₀ range 4-20.9 days, DT₉₀ (measured) range 19.5-69.3 days, Soils=11; Field studies DT₅₀ (normalised) range 3.7-6.2 days, DT₉₀ (measured) range 12.3-20.6 days, Soils =4; Other studies: DT₅₀ 2-4 days (F3)

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

13.9

Moderately fast

Note

pH sensitive: 3.8 days at pH 5, 24.6 days at pH 9

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Moderately persistent

Note

pH sensitive: 3.7 days at pH 5, 36 days at pH 9

Water-sediment DT₅₀ (days)

26.4

Fast

Water phase only DT₅₀ (days)

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

0.68

Mobile

K_foc (mL g⁻¹)

¹/_n

0.92

Notes and range

EU 2008 dossier K_f range 0.36-1.28 mL g⁻¹, K_foc range 25-132 mL g⁻¹, ¹/_n range 0.90-0.94, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.46

Calculated

Low leachability

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

Value

3.74 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

Bio-concentration factor

BCF (l kg⁻¹)

1.3

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

methyl saccharine (Ref: IN W6725)

Major fraction

0.881

N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN D8526)

Major fraction

0.923

N-desmethyl triazine amine (Ref: IN E7710)

Major fraction

0.547

N,N-bis-desmethyl triazine amine (Ref: IN M7222)

Major fraction

0.317

triflusulfuron

Major fraction

1,1,3-trioxo-1,2-benzothiazole-7-carboxylic acid (Ref: IN-JU127)

Major fraction

0.158

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)

N,N-dimethyl-6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN D8526)

Relevant

N-desmethyl triazine amine (Ref: IN E7710)

Relevant

0.0015

N,N-bis-desmethyl triazine amine (Ref: IN M7222)

Relevant

0.0015

methyl saccharine (Ref: IN W6725)

Relevant

1,1,3-trioxo-1,2-benzothiazole-7-carboxylic acid (Ref: IN-JU127)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

6-(2,2,2-trifluoroethoxy)-1,3,5-triazine-2,4-diamine (Ref: IN-M7222)

N,N-bis-desmethyl triazine amine

Rat; Plant

triflusulfuron

Surface water/sediment

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)

> 6.9

Rat

High

(ppm diet)

> 100

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

> 89.5

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1535 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

27.6

Colinus virginianus NOEL

Moderate

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

> 1000

Eisenia foetida

Low

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

125

Eisenia foetida

Low

Soil micro-organisms

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

Dose: 225 mg kg⁻¹ soil 56 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

23.8

Folsomia candida

Non-target plants

17.8

Grain sorghum
Vegetative vigour, ER₅₀
as g ha⁻¹

23.5

OSR
Seedling emergence, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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

Chronic as 10-day LC₅₀ µg bee⁻¹ day⁻¹

> 96.6

Apis mellifera

Bumblebees (Bombus spp.)

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

> 100

Bombus terrestris

Low

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

> 100

Bombus terrestris

Low

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 LR₅₀ g ha⁻¹

> 60

Chrysoperla carnea

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

> 60.0

Aphidius rhopalosiphi

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

> 6.0

Typhlodromus pyri

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

> 120

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

730

Oncorhynchus mykiss

Low

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

10.0

Pimephales promelas

Moderate

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

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

> 960

Daphnia magna

Low

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

11.0

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)

0.0029

Lemna gibba

High

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

2.02

Anabaena flos-aquae

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.1

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

Rat as triflusulfuron

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

1.2

Rat as triflusulfuron

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

0.09

Rabbit SF=100

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

0.04

Rat as triflusulfuron

Dermal penetration studies (%)

25-75

concentration dependent

Dangerous Substances Directive 76/464

List II

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

Excreted rapidly, within 72hrs, >=80% urinary and bile excretion

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

May affect body weight and food intake
Possible liver, blood and testes toxicant
US EPA - possible human carcinogen; CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Treat fires with water spray, foam, dry chemical or CO2
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

triflusulfuron-methyl

French

triflusulfuron-methyle

German

Triflusulfuron

Danish

triflusulfuron-methyl

Italian

triflusulfuron-metile

Spanish

triflusulfuron-metil

Greek

Polish

triflusulfuron metylu

Swedish

triflusulfuronmetyl

Hungarian

triszulfuron-metil

Dutch

Norwegian

Record last updated:	22/08/2024
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