Flupyrsulfuron-methyl-sodium

Flupyrsulfuron-methyl-sodium	Last updated: 19/12/2024
(Also known as: flupyrsulfuron-methyl-sodium)

SUMMARY

Flupyrsulfuron-methyl-sodium is a selective sulfonylurea herbicide for post-emergence control of broad-leaved weeds in cereals. It is highly soluble in water but less so in organic solvents. Its volatility is low and it tends not to persistent in soil or water-sediment systems. No significant risks to human health have been identified. Toxicity to biodiversity tends to be low to moderate with the exception of algae and aquatic plants where flupyrsulfuron-methyl-sodium is highly toxic.

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 High alert: Earthworms chronic ecotoxicity: High	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A selective sulfonylurea herbicide for post-emergence control of broad-leaved weeds in cereals

Example pests controlled

Broad-leaved weeds including blackgrass

Example applications

Cereals including wheat, barley

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1998, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₁₃F₃N₅NaO₇S

Canonical SMILES

COC1=CC(=NC(=N1)[N-]C(=O)NS(=O)(=O)C2=C(C=CC(=N2)C(F)(F)F)C(=O)OC)OC.[Na+]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

DTVOKYWXACGVGO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H14F3N5O7S.Na/c1-28-9-6-10(29-2)21-13(20-9)22-14(25)23-31(26,27)11-7(12(24)30-3)4-5-8(19-11)15(16,17)18;/h4-6H,1-3H3,(H2,20,21,22,23,25);/q;+1/p-1

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Pyrimidinylsulfonylurea herbicide; Sulfonylurea herbicide

Minimum active substance purity

933 g kg⁻¹

Known relevant impurities

EU dossier - methanol 52g kg⁻¹

Substance origin

Synthetic

Mode of action

Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS)

CAS RN

144740-54-5

EC number

604-441-5

CIPAC number

577.501

US EPA chemical code

PubChem CID

15764724

CLP index number

613-165-00-4

Molecular mass

487.3

PIN (Preferred Identification Name)

IUPAC name

sodium (4,6-dimethoxypyrimidin-2-yl)[({[3-(methoxycarbonyl)-6-(trifluoromethyl)pyridin-2-yl]sulfonyl}amino)carbonyl]azanide

CAS name

sodium salt of methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-6-(trifluoromethyl)-3-pyridinecarboxylate

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

Alopecurus myosuroides

Physical state

White powder with dry odour

Related substances & organisms

flupyrsulfuron

Formulations

Property

Value

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

DuPont
Headland

Example products using this active

Absolute
Bullion
Excalibur
Lancer
Pennant
Lexus
Oklar
Ductis

Formulation and application details

Often supplied as wettable granules that are mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

603

at pH5

High

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

3100

Acetone

Benzene

490

Ethyl acetate

5000

Methanol

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

165

Flashpoint (°C)

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

1.45 X 10⁰¹

Calculated

Log P

1.16

at pH6

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.55

Dissociation constant pKa) at 25 °C

4.94

Weak acid

Vapour pressure at 20 °C (mPa)

1.00 X 10^-06

Low volatility

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

1.00 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

0.1

Volatilisation is not considered critical for air pollution

From soil surface

2.8

Volatilisation is not considered critical for air pollution

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

Surface tension (mN m⁻¹)

56.7

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

18.2

Non-persistent

DT₅₀ (lab at 20 °C)

18.2

Non-persistent

DT₅₀ (field)

7.5

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

60.3

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 10.8-30.4 days, DT₉₀ range 39.4-199.2 days, field studies DT₅₀ range 6.6-19.2 days (UK, France), DT₉₀ range 44.7-72.6 days

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

8.7

Moderately fast

Note

pH sensitive: DT₅₀ 40 days at pH 5, 0.39 days at pH 9, all at 20 °C

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ 44 days at pH 5, 0.4 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

8.0

Fast

Water phase only DT₅₀ (days)

5.0

Moderately fast

Sediment phase only DT₅₀ (days)

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)

0.39

Mobile

K_oc (mL g⁻¹)

22.5

Notes and range

EU dossier (2014) K_d range 0.13-0.71 mL g⁻¹, K_oc range 15-55 mL g⁻¹

Freundlich

K_f (mL g⁻¹)

0.29

Mobile

K_foc (mL g⁻¹)

22.0

¹/_n

0.88

Notes and range

EU dossier (2014) kf range 0.13-0.50 mL g⁻¹, K_foc range 15-23 mL g⁻¹, ¹/_n range 0.85-0.91, soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.33

Calculated

Transition state

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

Value

2.15 X 10^-02

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

1.27

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)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4,6-dimethoxypyrimidin-2-amine (Ref: IN-J0290)

Major fraction

2-amino-4,6-dimethoxypyrimidine (Ref: AE-F092944)

Major fraction

0.323

methyl 2-((4-hydroxy-6-methoxypyrimidin-2-yl)amino)-6-(trifluoromethyl)nicotinate (Ref: IN KV996)

Major fraction

0.203

1-(4-hydroxy-6-methoxypyrimidin-2-yl)-7-(trifluoromethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Ref: IN-KC576)

Major fraction

0.109

Aerobic

1-(4,6-dihydroxypyrimidin-2-yl)-7-(trifluoromethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Ref: IN-KF311)

2-sulfamoyl-6-(trifluoromethyl)nicotinic acid (Ref: IN-KY374)

flupyrsulfuron

Major fraction

1-(4,6-dimethoxypyrimidine-2-yl)-2,4-diketo-7-trifluoro-methyl-1,2,3,4-tetrahydropyridol(2,3-d)pyrimidine (Ref: IN JV460)

Major fraction

0.590

N-(4,6-dimethoxypyrimidine-2-yl)-N-(3-methoxycarbonyl-6-trifluoromethylpyridine-2-yl)-amine (Ref: IN KY374)

Major fraction

0.323

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)

1-(4,6-dimethoxypyrimidine-2-yl)-2,4-diketo-7-trifluoro-methyl-1,2,3,4-tetrahydropyridol(2,3-d)pyrimidine (Ref: IN JV460)

Relevant

N-(4,6-dimethoxypyrimidine-2-yl)-N-(3-methoxycarbonyl-6-trifluoromethylpyridine-2-yl)-amine (Ref: IN KY374)

Relevant

1-(4-hydroxy-6-methoxypyrimidin-2-yl)-7-(trifluoromethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Ref: IN-KC576)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

methyl 2-sulfamoyl-6-(trifluoromethyl)nicotinate (Ref: IN-JE127)

Water (Hydrolysis)

0.125

methyl 2-[carbamoyl(4,6-dimethoxypyrimidin-2-yl)amino]-6-(trifluoromethyl)nicotinate (Ref: IN-KT982)

Water (Photolysis)

0.100

potassium {(4,6-dimethoxypyrimidin-2-yl)[3-(methoxycarbonyl)-6-(trifluoromethyl)pyridin-2-(methoxycarbonyl)-6-(trifluoromethyl)pyridin-2- (Ref: IN-KV994)
Note: LC50(fish) > 0.001 mg/l; EC50(daphnids) > 0.001 mg/l

Water (Photolysis)

0.103

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)amino]-6-(trifluoromethyl)nicotinate (Ref: IN-KF526)
Note: LC50(fish) > 10 mg/l; EC50(daphnids) > 0.5 mg/l

Water (Photolysis)

0.210

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)

(ppm diet)

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

> 353

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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)

> 0.065

Eisenia foetida

High

Soil micro-organisms

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

Dose: 0.02 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 25

Apis mellifera

Moderate

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

> 30

Apis mellifera

Moderate

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

Chronic

Notes

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)

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

> 10

Aphidius rhopalosiphi Adult

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

> 10

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

470

Oncorhynchus mykiss

Low

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

130

Oncorhynchus mykiss 28 day

Low

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

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

721

Daphnia magna

Low

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

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)

0.0025

Lemna gibba

High

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

0.0037

Raphidocelis subcapitata

High

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

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.8

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.035

Mouse SF=100

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

None allocated

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

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

0.08

Dog 1 year SF=100

Dermal penetration studies (%)

1.0-60.0%

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Minimal risk of dietary exposure
No unacceptable risk 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

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver toxicant

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

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

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

flupyrsulfuron-methyl-sodium

French

flupyrsulfuron-methyle

German

Flupyrsulfuron

Danish

flupyrsulfuron-methyl

Italian

flupyrsulfuron-methyl

Spanish

flupyrsulfuron-metil

Greek

flupyrsulfuron-methyl

Polish

flupirsulfuron metylowy

Swedish

flupyrsulfuronmetylnatrium

Hungarian

flupyrsulfuron-methyl

Dutch

flupyrsulfuron-methyl

Norwegian

Record last updated:	19/12/2024
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