flupyrsulfuron-methyl-sodium ** flupyrsulfuron-methyl-sodium ** Translations

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GENERAL INFORMATION
for flupyrsulfuron-methyl-sodium

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

EC Regulation 1107/2009 (repealing 91/414):

Status	Not approved
Dossier rapporteur/co-rapporteur	France
Date inclusion expires	Not applicable
EU Candidate for substitution (CfS)	Not applicable
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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
Known relevant impurities	EU dossier - methanol 52g/kg
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 (g mol-1)	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)	B
Herbicide Resistance Classification (WSSA)	2
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	DuPont Headland
Example products using this active	Absolute Bullion Excalibur Lancer Pennant Lexus Oklar Ductis
UK LERAP status	No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details	Often supplied as wettable granules that are mixed with water and applied as a spray.

ENVIRONMENTAL FATE
for flupyrsulfuron-methyl-sodium

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		603	A4 - @ pH5	High
Solubility - In organic solvents at 20oC (mg l-1)		3100	A5 - Acetone	-
		28	A5 - Benzene	-
		490	A5 - Ethyl acetate	-
		5000	A5 - Methanol	-
Melting point (oC)		Decomposes before melting	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		165	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.45 X 1001	Calculated	-
	Log P	1.16	A5 - @ pH6	Low
Bulk density (g ml-1)/Specific gravity		1.55	A5	-
Dissociation constant (pKa) at 25oC		4.94	A5	-
		Note: Weak acid
Vapour pressure at 20oC (mPa)		1.00 X 10-06	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		1.00 X 10-08	A5	Non-volatile
GUS leaching potential index		3.35	Calculated	High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	2.92 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		-	-	-
Surface tension (mN m-1)		56.7	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	18.2	A5	Non-persistent
	DT50 (lab at 20oC)	18.2	A5	Non-persistent
	DT50 (field)	7.5	A5	Non-persistent
	DT90 (lab at 20oC)	50	A5	-
	DT90 (field)	60.3	A5	-
	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	A5	Moderately fast
	Note	pH sensitive: DT50 40 days at pH 5, 0.39 days at pH 9, all at 20 degC
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	12	A5	Non-persistent
	Note	pH sensitive: DT50 44 days at pH 5, 0.4 days at pH 9, all at 20 degC
Water-sediment DT50 (days)		8.0	A5	Fast
Water phase only DT50 (days)		5.0	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	0.39	A5	Mobile
	Koc	22.5
	Notes and range	EU dossier (2014) Kd range 0.13-0.71 mL/g, Koc range 15-55 mL/g
Freundlich	Kf	0.29	A5	Mobile
	Kfoc	22.0
	1/n	0.88
	Notes and range	EU dossier (2014) kf range 0.13-0.50 mL/g, Kfoc range 15-23 mL/g, 1/n range 0.85-0.91, soils=5
pH sensitivity		No

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
methyl 2-sulfamoyl-6-(trifluoromethyl)nicotinate (Ref: IN-JE127)	-	Water (Hydrolysis)	0.125	-
1-(4-hydroxy-6-methoxypyrimidin-2-yl)-7-(trifluoromethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Ref: IN-KC576)	-	Soil (Aerobic)	-	-
1-(4,6-dihydroxypyrimidin-2-yl)-7-(trifluoromethyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (Ref: IN-KF311)	-	Field; Groundwater	-	-
methyl 2-[(4,6-dimethoxypyrimidin-2-yl)amino]-6-(trifluoromethyl)nicotinate (Ref: IN-KF526) Note: LC50(fish) > 10 mg l-1; EC50(daphnids) > 0.5 mg l-1	-	Water (Photolysis)	0.210	-
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-1; EC50(daphnids) > 0.001 mg l-1	-	Water (Photolysis)	0.103	-
2-sulfamoyl-6-(trifluoromethyl)nicotinic acid (Ref: IN-KY374)	-	Groundwater; Soil	-	-

ECOTOXICOLOGY
for flupyrsulfuron-methyl-sodium

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	Low risk	A5 Based on LogP < 3	Low potential
	CT50 (days)	-		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	-	-	-
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2250	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		470	A5 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l-1)		130	A4 Oncorhynchus mykiss, 28 day	Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		721	A5 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		16	A5 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	A5 Lemna gibba	High
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.0037	A5 Raphidocelis subcapitata	High
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 25	A5	Moderate
	Oral acute 48 hour LD50 (μg bee-1)	> 30	A5	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1000	A5	Low
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	41.1	Beneficial capacity Dose:0.016 kg ha-1 A5 Aphidius rhopalosiphi, adult	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	7.1	Beneficial capacity Dose: 0.016 kg ha-1 A5 Typhlodromus pyri, protonymph	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 0.02 kg ha-1	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for flupyrsulfuron-methyl-sodium

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 5.8	A5 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.035	A5 Mouse, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.08	A4 Dog, 1 year, SF=100	-
Dermal penetration studies (%)		1.0-60.0%	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Minimal risk of dietary exposure No unacceptable risk to bystanders identified
	Occupational	No unacceptable risks to operators or other workers identified
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		Possible liver toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		Usually 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for flupyrsulfuron-methyl-sodium

Language	Name
English	flupyrsulfuron-methyl-sodium
French	flupyrsulfuron-methyle
German	Flupyrsulfuron
Danish	flupyrsulfuron-methyl
Italian	flupyrsulfuron-methyl
Spanish	flupyrsulfuron-metil
Greek	flupyrsulfuron-methyl
Slovenian	flupirsulfuronmetil
Polish	flupirsulfuron metylowy
Swedish	flupyrsulfuronmetylnatrium
Hungarian	flupyrsulfuron-methyl
Dutch	flupyrsulfuron-methyl

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Record last updated: Monday 28 May 2018
Contact: aeru@herts.ac.uk