Flupyrsulfuron-methyl-sodium

Flupyrsulfuron-methyl-sodium	Last updated: 28/01/2021
(Also known as: flupyrsulfuron-methyl-sodium)

GENERAL INFORMATION

Description

A selective sulfonylurea herbicide for post-emergent 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

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

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
		✓

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 group

Sulfonylurea

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

CIPAC number

577.501

US EPA chemical code

PubChem CID

15764724

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 Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Alopecurus myosuroides

Physical state

White powder with dry odour

Related substances & organisms

carfentrazone-ethyl

thifensulfuron-methyl

tribenuron-methyl

flupyrsulfuron

Formulations

Property

Value

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

Absolute
Bullion
Excalibur
Lancer
Pennant
Lexus
Oklar
Ductis

Example products using this active

DuPont
Headland

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)

Not expected to self ignite; Not highly flammable

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

1.45 X 10⁰¹

Calculated

Log P

1.16

at pH6

Low

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

0.39

Mobile

K_oc

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

0.29

Mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.590

Major fraction, Relevant

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

Soil

0.323

Major fraction, Relevant

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

Soil

0.323

Major fraction, Relevant

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

Soil

0.203

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

Soil (Aerobic)

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

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

Field; Groundwater

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

Groundwater; Soil

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)

> 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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

470

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

130

Oncorhynchus mykiss 28 day

Low

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

721

Daphnia magna

Low

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

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)

0.0025

Lemna gibba

High

Non-target plants

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

0.0037

Raphidocelis subcapitata

High

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)

> 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)

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)

> 0.065

Eisenia foetida

High

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

41.1

Beneficial capacity [Dose:0.016 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

7.1

Beneficial capacity [Dose: 0.016 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 0.02 kg ha⁻¹

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)

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

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 Code is usually 9

CLP classification 2013

Environment: H400, H410

EC Risk Classification

Carcinogen category 2: R45,, Reproduction category 2: R61
N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

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

Record last updated:	28/01/2021
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