metsulfuron-methyl (Ref: DPX T6376) ** metsulfuron ** IN T6376 ** Translations

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GENERAL INFORMATION
for metsulfuron-methyl

Description: A herbicide used to control weeds mainly in cereals and land temporarily removed from production. It is also be a pesticide transformation product.

Example pests controlled: Broad-leaved weeds; Some annual grasses

Example applications: Spring & winter cereals; Land removed from production

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1983, first reported; 1984, first approvals

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

Status	Approved
Dossier rapporteur/co-rapporteur	Slovenia/Sweden
Date inclusion expires	31/03/2023
EU Candidate for substitution (CfS)	Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
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

Also used in: Australia

Chemical structure:

Isomerism	None
Chemical formula	C14H15N5O6S
Canonical SMILES	CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	RSMUVYRMZCOLBH-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C14H15N5O6S/c1-8-15-12(18-14(16-8)25-3)17-13(21)19-26(22,23)10-7-5-4-6-9(10)11(20)24-2/h4-7H,1-3H3,(H2,15,16,17,18,19,21)
2D structure diagram/image available?	Yes

General status:

Pesticide type	Herbicide, Metabolite
Metabolite Type	Soil
Substance group	Sulfonylurea
Minimum active substance purity	967 g/kg
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Selective, systemic with contact and residual action. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
CAS RN	74223-64-6
EC number	-
CIPAC number	441.201
US EPA chemical code	122010
PubChem CID	52999
Molecular mass (g mol-1)	381.36
PIN (Preferred Identification Name)	-
IUPAC name	methyl 2-(4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)benzoate
CAS name	methyl 2-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoate
Other status information	PAN listed Highly Hazardous Chemical
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	Lolium rigidum Bacopa rotundifolia
Physical state	White to pale yellow solid with charcateristic odour
Related substances & organisms	carfentrazone-ethyl thifensulfuron-methyl tribenuron-methyl metsulfuron

Can be a metabolite of:

Parent		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
iodosulfuron-methyl-sodium		Soil	0.885	Major fraction, Relevany unknown
iodosulfuron		Soil	0.885	Major fraction; Relevany unknown

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	AgriGuard Clayton DuPont Headland Nufarm
Example products using this active	Ally Express Ally Max Ally 20 SG Cimarron Concert Finish Minx PX Pike
UK LERAP status	Buffer probably required in UK - see product label
Formulation and application details	Often supplied as wettable or water soluble granules or as a dry flowable formulation.

ENVIRONMENTAL FATE
for metsulfuron-methyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		2790	A5 - @ 25 DegC	High
Solubility - In organic solvents at 20oC (mg l-1)		0.058	A5 - n-Hexane	-
		37000	A5 - Acetone	-
		763	A5 - Methanol	-
		124	A5 - Toluene	-
Melting point (oC)		162	A5	-
Boiling point (oC)		-	-	-
Degradation point (oC)		164	A3	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.35 X 10-02	Calculated	-
	Log P	-1.87	A5	Low
Bulk density (g ml-1)/Specific gravity		1.45	A5	-
Dissociation constant (pKa) at 25oC		3.75	A5	-
		Note: Weak acid
Vapour pressure at 20oC (mPa)		1.40 X 10-08	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.87 X 10-06	A5	Non-volatile
GUS leaching potential index		3.99	Calculated	High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	6.89 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Low
Maximum UV-vis absorption L mol-1 cm-1		pH 1.8: 235nm=15752 pH 7.0: 235nm=16032 pH 10: 235nm=14658	A4	-
Surface tension (mN m-1)		71.7	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	10	A5	Non-persistent
	DT50 (lab at 20oC)	23.2	A5	Non-persistent
	DT50 (field)	13.3	A5	Non-persistent
	DT90 (lab at 20oC)	102.4	A5	-
	DT90 (field)	54.8	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier (2015) lab studies DT50 range 6.4-48.8 days 8 soils, DT90 range 48-175 days; field studies DT50 range 7.3-37.1 days, DT90 range 24.3-123 days Soils =4
Dissipation rate RL50 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL50 on and in plant matrix	Value	5.2	R4	-
	Note	Published literature RL50 range 4.8-5.6 days, 2 cereal crops, whole plant, n=2
Aqueous photolysis DT50 (days) at pH 7	Value	Stable	A5	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	DT50 22 days at pH 5, stable at pH 7 and pH 9, all at 25 degC
Water-sediment DT50 (days)		224.3	A5	Slow
Water phase only DT50 (days)		115	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	0.77	A5	Very mobile
	Kfoc	12.0
	1/n	0.98
	Notes and range	EU 2015 dossier Kf range 0.1-4.9 mL/g, Kfoc range 4-207 mL/g, Soils=16
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
methyl 2-(aminosulfonyl)benzoate (Ref: IN-D5803)		Soil	0.487	Major fraction, Relevant
2-(aminosulfonyl) benzoic acid (Ref: IN-D5119)		Soil	0.059	Major fraction, Relevant
phenylurea (Ref: IN-B5685)		Soil	0.170	Major fraction, Relevant
1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN-00581)		Soil	0.087	Major fraction, Relevant
2-amino-4-methoxy-6-methyl-1,3,5-triazine (Ref: IN-A4098)		Soil	0.423	Major fraction, Relevant
metsulfuron		Soil	-	-

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
metsulfuron (Ref: ) Note: -	-	-	-	-

ECOTOXICOLOGY
for metsulfuron-methyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1	A5 (Other literature Log BCF range 0.0-1.6 (R3))	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	-	L2 Rat, 2 year	-
	(ppm diet)	> 500		-
Birds - Acute LD50 (mg kg-1)		> 2510	A5 Anas platyrhynchos	Low
Birds - Short term dietary (LC50/LD50)		> 5620 mg kg feed-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		> 113	A5 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l-1)		68.0	A5 Oncorhynchus mykiss	Low
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 120	A5 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		150	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)		0.00036	A5 Lemna gibba	High
Non-target plants		0.054	A5 White mustard Vegetative vigour, ER50 as g/ha	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.875	A4 Raphidocelis subcapitata, 72 hour	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		0.02	Q2 Unknown species	Moderate
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 50	A5	Moderate
	Oral acute 48 hour LD50 (μg bee-1)	> 44.3	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	76.8	> A5 Aphidius rhopalosiphi	-
	% Effect	19.3	Beneficial capacity A4 Aphidius rhopalosiphi	-
Other arthropod (2)	LR50 g ha-1	30.7	A5 Typhlodromus pyri	-
	% Effect	-1.2	Beneficial capacity A4 Typhlodromus pyri	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 0.2 mg kg-1 soil	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for metsulfuron-methyl

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)		6.2	A5 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.22	A5 Rat, 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)		0.7	A5	-
Dermal penetration studies (%)		25-75	A5 concentration dependent	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks 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		No further information available

: 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		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)		III	-	Caution - Slightly toxic
UN Number		Usually 3077
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for metsulfuron-methyl

Language	Name
English	metsulfuron-methyl
French	metsulfuron-methyle
German	Metsulfuron-methyl
Danish	metsulfuron-methyl
Italian	metsulfuron-metile
Spanish	metsulfuron-metil
Greek	metsulfuron-methyl
Slovenian	metsulfuron metil
Polish	metsulfuron metylu
Swedish	metsulfuronmetyl
Hungarian	metsulphuron-methyl
Dutch	metsulfuron methyl

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Record last updated: Wednesday 23 May 2018
Contact: aeru@herts.ac.uk