Tritosulfuron

Tritosulfuron	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A herbicide used to control a wide range of broad-leaved weeds in cereals and other crops

Example pests controlled

Wild bishop; Milk thistle; Cocklebur; Nightshade; Annual dicots

Example applications

Cereals including wheat, barley, oat; Maize

Efficacy & activity

Efficacy deminstrated via field trials and extensive use

Availability status

Current

Introduction & key dates

2002

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Slovenia/Austria

Date EC 1107/2009 inclusion expires

30/11/2021

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

Chemical structure

Isomerism

Chemical formula

C₁₃H₉F₆N₅O₄S

Canonical SMILES

COC1=NC(=NC(=N1)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(F)(F)F)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

KVEQCVKVIFQSGC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H9F6N5O4S/c1-28-11-21-8(13(17,18)19)20-9(23-11)22-10(25)24-29(26,27)7-5-3-2-4-6(7)12(14,15)16/h2-5H,1H3,(H2,20,21,22,23,24,25)/f/h22,24H

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

960 g/Kg

Known relevant impurities

EU dossier: AMTT <0.2 g/Kg

Substance origin

Synthetic

Mode of action

Inhibits amino acid sysnthesis. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

142469-14-5

EC number

Not assigned

CIPAC number

735

US EPA chemical code

PubChem CID

11657899

Molecular mass

445.30

Chemical name

N-((4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl)carbamoyl)-2-(trifluoromethyl)benzene-1-sulfonamide

PIN (Preferred Identification Name)

N-((4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl)carbamoyl)-2-(trifluoromethyl)benzene-1-sulfonamide

IUPAC name

1-(4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl)-3-[2-(trifluoromethyl)benzenesulfonyl]urea

CAS name

N-(((4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl)amino)carbonyl)-2-(trifluoromethyl)benzenesulfonamide

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

Physical state

White crystalline solid

Formulations

Property

Value

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

Arrat

Example products using this active

BASF

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

78.3

at pH 10.2

Moderate

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

10000

Toluene

25000

Dichloromethane

23000

Methanol

85000

Ethyl acetate

Melting point (°C)

166.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

4.17 X 10⁰⁰

Calculated

Log P

0.62

Low

Bulk density (g ml⁻¹)

1.678

Dissociation constant pKa) at 25 °C

4.69

Vapour pressure at 20 °C (mPa)

9.3 X 10^-05

Low volatility

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

7.8 X 10^-10

Non-volatile

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

pH 0.5: 202nm = 24440; 212nm = 21412; 226nm = 25172nm; 254nm = 7037; 303nm = 212
pH 6.7: 202nm = 18331; 215nm = 18515; 237nm = 21494; 260nm = 13021; 300nm = 144
pH 13.3: 219nm = 18151; 235nm = 15825; 260nm = 11908; 300nm = 1890

Surface tension (mN m⁻¹)

64.6

20 °C 1% aqueous solution

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

25.1

Non-persistent

DT₅₀ (lab at 20 °C)

25.1

Non-persistent

DT₅₀ (field)

8.2

Non-persistent

DT₉₀ (lab at 20 °C)

153

Persistent

DT₉₀ (field)

47.5

DT₅₀ modelling endpoint

Note

EU 2018 dossier Lab studies DT₅₀ (normalised) range 10.3-199.4 days, DT₉₀ (actual) range 48.4-584.4 days, Soils=7, Field studies DT₅₀ (normalised) range 3.1-36.5 days, DT₉₀ (actual) range 6.2-174.2 days, Soils=15

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

Stable at all environmentally relevant pHs

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

Value

Moderately persistent

Note

pH sensitive: pH4: DT₅₀ 56 days, pH9: DT₅₀ 20 days

Water-sediment DT₅₀ (days)

56.5

Moderately fast

Water phase only DT₅₀ (days)

49.5

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

0.1

Very mobile

K_foc

8.9

¹/_n

0.94

Notes and range

EU 2018 dossier K_f range 0.05-0.204 mL g⁻¹, K_foc range 3.94-15.4 mL g⁻¹, ¹/_n range 0.86-0.99, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.79

Calculated

Transition state

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

Value

3.89 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Very mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

1-(carbamoylamidino)-3-(2-trifluoromethyl-benzenesulfonyl) urea (Ref: BH 635-4)

Soil

0.564

Major fraction; Relevant

2-trifluoromethyl-benzenesulfonamide (Ref: BH 635-2)

Soil

0.231

Major fraction; Relevant

1-amidino-3-(2-trifluoromethyl-benzenesulfonyl) urea (Ref: BH 635-3)

Soil

0.148

Major fraction; Relevant

2-amino-4-methoxy-6-(trifluoromethyl)-1,3,5-triazine (Ref: BH 635-5)

Soil

0.063

Minor fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-hydoxy-6- trifluoromethylbenzenesulfonamide

635M06

Plant

5-(hexopyranosyloxy)-2-(trifluoromethyl)benzene-sulfonamide

635M07

Plant

N-(methoxycarbonyl)-2-trifluoromethyl-benzenesulfonamide

635M08

Rat

N-[4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl]urea

635M09

Animal

amino{[amino(imino)methyl]amino}oxomethane

635M010

Plant

2-amino-4-hydroxy-6-trifluoromethyl-

635M11

Rat; Water

3-{[({[[(aminocarbonyl)amino]-(imino)methyl]amino}carbonyl)-amino]sulfonyl}-4-(trifluoromethyl)-phenyl hexopyranoside

635M12

Plant

3-{[({[4-methoxy-6-(trifluoro-methyl)-1,3,5-triazin-2-yl]amino}-carbonyl)amino]sulfonyl}-4-(trifluoromethyl)phenylhexopyranoside

635M13

Plant

3-{[({[4-methoxy-6-(trifluoro-methyl)-1,3,5-triazin-2-yl]amino}-carbonyl)amino]sulfonyl}-4-(trifluoromethyl)phenylhexopyranoside

635M15

Rat

1-{[({[[(aminocarbonyl)amino]-(imino)methyl]amino}carbonyl)-amino]sulfonyl}-4-hydroxy-2-(trifluoromethyl) benzene

635M16

Rat

1-[(4-methoxy-6-trifluoromethyl)-1,3,5-triazin-2-yl]-3-(5-hydroxy-2-trifluoromethyl-benzenesulfonyl) urea

635M17

Rat; Plant; water

1-{[(aminocarbonyl)amino]-sulfonyl}-2-(trifluoromethyl) benzene

635M18

Rat; Plant

2-hydroxy-4-(trifluoromethyl)-6-{[({[2(trifluoromethyl)phenyl]-sulfonyl}amino)carbonyl]amino}-1,3,5-triazine

635M19

Rat; Soil; Water

1-[(4-amino-6-trifluoromethyl)-1,3,5-triazin-2-yl]-3-(2-trifluoro-methylbenzenesulfonyl)

635M21

Rat

2-(trifluoromethyl)benzene sulfonic acid

635M23

Rat; Plant

635M24

Rat

635M25

Rat

[3-{[({[[(aminocarbonyl)amino](imino)methyl]amino}-carbonyl)amino]sulfonyl}-4-(trifluoromethyl)phenyl] cysteine

635M28

Rat

[3-{[({[4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl]amino}carbonyl)amino]sulfonyl}-4-(trifluoromethyl)phenyl] cysteine

635M29

Rat

635M30

Rat

2-methoxy-4-{[({[4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl]amino}carbonyl)amino]sulfonyl}-5-(trifluoromethyl)phenyl hydrogen sulfate

635M31

Rat

4-{[({[4-methoxy-6-(trifluoromethyl)-1,3,5-triazin-2-yl]amino}carbonyl)amino]sulfonyl}-3-(trifluoromethyl)phenyl hydrogen sulfate

635M32

Rat

635M34

Rat

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

3870

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg diet⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

21.5

Oncorhynchus mykiss

Low

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

> 100

Daphnia magna

Low

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

100

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)

0.026

Lemna gibba

Moderate

Non-target plants

5.75

Tomato
Vegetative vigour, ER₅₀
as g ha⁻¹

12.4

Tomato
Seedling emergence, ER₅₀
as g ha⁻¹

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

0.23

Pseudokirchneriella subcapitata

Moderate

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

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

200

Apis mellifera

Low

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

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)

7.5

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

28.6

Mortality
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Mortality
Aphidius rhopalosiphi

Soil micro-organisms

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

Dose up to 0.35 kg BAS 635 00 H + 6.25 L BAS 152 00 S

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)

3870

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.4

Rat 4 hr (dust aerosol)

Other Mammal toxicity endpoints

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

0.06

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

None allocated

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

None allocated

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

0.15

Rat SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Risks acceptable for intended uses

Occupational

Risks acceptable for intended uses

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

Possible liver and kidney toxicant
Skin sensitiser

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R51/53

EC Safety Classification

S36/37, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

tritosulfuron

French

tritosulfuron

German

Tritosulfuron

Danish

tritosulfuron

Italian

tritosulfuron

Spanish

tritosulfuron

Greek

Polish

tritosulfuron

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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