bensulfuron-methyl (Ref: DPX F5384) ** methyl bensulfuron ** DPX 84 ** F 5384 ** Translations

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SUMMARY

Bensulfuron-methyl is a herbicide approved for use in the EU. It is moderately soluble in water, non-volatile and moderately mobile. It would not be expected to persistent in soil but could be persistent in water systems under certain conditions. It is not highly toxic to mammals. It also shows a low toxicity to birds and earthworms but is more of a concern to aquatic plants, algae and honeybees

GENERAL INFORMATION
for bensulfuron-methyl

Description: A pyrimidinylsulfonylurea herbicide used to control annual and perennial weeds and sedges

Example pests controlled: Pigweed; Chickweed; Wild mustard; Stinkgrass; Barnyardgrass; Rice flatsedge; Dwarf umbrella grass; Nut-grass; Creeping water primrose

Example applications: Cereals especially wheat; Rice

Availability status: Current

Introduction & key dates: 1985

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

Status	Approved
Dossier rapporteur/co-rapporteur	Italy
Date inclusion expires	31/10/2019

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, USA

General status:

Pesticide type	Herbicide
Substance group	Sulfonylurea
Minimum active substance purity	-
Known relevant impurities	EU dossier - None declared
Substance origin	Synthetic
Mode of action	Selective, systemic action being absorbed through foliage and roots. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
CAS RN	83055-99-6
EC number	401-340-6
CIPAC number	502
US EPA chemical code	128820
Chiral molecule	No
Chemical formula	C16H18N4O7S
SMILES	O=C(Nc1nc(OC)cc(OC)n1)NS(=O)(=O)Cc2ccccc2C(=O)OC
International Chemical Identifier key (InChIKey)	XMQFTWRPUQYINF-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C16H18N4O7S/c1-25-12-8-13(26-2)18-15(17-12)19-16(22)20-28(23,24)9-10-6-4-5-7-11(10)14(21)27-3/h4-8H,9H2,1-3H3,(H2,17,18,19,20,22)
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	410.4
PIN (Preferred Identification Name)	methyl 2-({[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}methyl)benzoate
IUPAC name	methyl α-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-o-toluate
CAS name	methyl 2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoate
Other status information	-
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	Alisma plantago-aquatica Bacopa rotundifolia
Physical state	White to straw coloured solid
Related substances & organisms	bensulfuron

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	United Phosphorus DuPont
Example products using this active	Londax Sectar Testar
UK LERAP status	No UK approval for use or outside scope
Formulation and application details	Usually supplied as water dispersible granules that are mixed with water and used as a spray.

ENVIRONMENTAL FATE
for bensulfuron-methyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		67	A5	Moderate
Solubility - In organic solvents at 20oC (mg l-1)		5100	A5 - Acetone	-
		18400	A5 - Dichloromethane	-
		1750	A5 - Ethyl acetate	-
		229	A5 - o-Xylene	-
Melting point (oC)		179.4	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		245	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	6.17 X 1000	Calculated	-
	Log P	0.79	A5	Low
Bulk density (g ml-1)/Specific gravity		1.41	L3	-
Dissociation constant (pKa) at 25oC		5.2	A5	-
		Note: Weak acid
Vapour pressure at 25oC (mPa)		2.80 X 10-09	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		2.00 X 10-11	A5	Non-volatile
Henry's law constant at 20oC (dimensionless)		7.04 X 10-15	Calculated	Non-volatile
GUS leaching potential index		2.62	Calculated	Transition state
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	1.89 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)		74.9	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	24	H4	Non-persistent
	DT50 (lab at 20oC)	77	A5	Moderately persistent
	DT50 (field)	8.2	A5	Non-persistent
	DT90 (lab at 20oC)	287.6	A5	-
	DT90 (field)	16.7	A5	-
	Note	EU dossier range lab studies DT50 25-102 days, DT90 range 214-339 days; field studies DT50 range 6-14 days, DT90 range 6.2-48 days
Plant matrix DT50 (days)	Value	-	-	-
	Note	-
Aqueous photolysis DT50 (days) at pH 7	Value	43	A3	Stable
	Note	DT50: 10 days irradiated pond water, 90 days irradiated creek water, 29 days irradiated pure water and stable in pure dark water
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Sensitive to pH: DT50 6.1 days at pH 4, 141 days at pH 9
Water-sediment DT50 (days)		48	A5	Moderately fast
Water phase only DT50 (days)		18.5	A5	Slow

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	6.6	A5	Moderately mobile
	Kfoc	409
	1/n	0.92
	Notes and range	EU dossier kf range 2.5-8.4 mL/g, Kfoc range 205-684 mL/g, 1/n range 0.88-1.08, Soils=7
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	91/414 relevancy
bensulfuron (Ref: IN-R9419)		Soil	0.277	Major fraction, Relevant
2-((aminosulfonyl)methyl)benzoic acid (Ref: IN-D1R84)		Soil	0.182	Major fraction, Relevant
2-amino-4,6-dimethoxypyrimidine (Ref: AE-F092944)		Soil	0.460	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
{[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamoyl}acetic acid (Ref: IN-DAT97)	-	a = Water/sediment; b = Groundwater	a=0.099	-
methyl 2-({[(4-hydroxy-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}methyl)benzoate (Ref: IN-F7880) Note: Med-high mobility	-	a = Water/sediment; b = Rice	a=0.097	-
4,6-dimethoxypyrimidin-2-amine (Ref: IN-J0290) Note: Low mobility	-	a = Soil; b = Rat; c = Water	a=0460	-
methyl 2-(sulfamoylmethyl)benzoate (Ref: IN-N5297)	-	a = Water/sediment; b = Animal (faeces, urine)	a=0.317	-
(4,6-dimethoxypyrimidin-2-yl)urea (Ref: IN-T5831)	-	a = Water (Photolysis); b = Groundwater	a=0.137	-

ECOTOXICOLOGY
for bensulfuron-methyl

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	1.6	A5	Low potential
	CT50 (days)	327		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	21.4	A5 Rat	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2510	A5 Anas platyrhynchos	Low
Birds - Short term dietary (LC50/LD50)		> 1690 mg kg bw-1 day-1	A5 Anas platyrhynchos	-
Fish - Acute 96 hour LC50 (mg l-1)		> 66	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		1.5	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		130	L3 Daphnia magna	Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		12	A5 Daphnia magna	Low
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		130	F3 Americamysis bahia	Low
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		125.0	A4 Chironomus tentans	Low
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)		0.0008	A5 Lemna gibba	High
Non-target plants		> 2.41	A5 Oilseed rape Seedling emergence, ER50 as g/ha	-
		> 2.08	A5 Soybean Vegetative vigour, ER50 as g/ha	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.02	L3 Raphidocelis subcapitata	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 51.4	A5	Moderate
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 1000	A5 Eisenia foetida	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	>600	48 hour A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	>600	7 day A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 5 x field rate	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for bensulfuron-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)		7.5	A5 Rat, 4 hr	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.2	A5 Dog, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.12	A5 Dog, SF=167	-
Dermal penetration studies (%)		5.9-7.2	A5 concentration dependant	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks identified for proposed uses
	Occupational	Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment
European MRLs		Click here for the EU MRL pesticide database
Drinking Water MAC (μg l-1)		0.1	EU Dir 89/778/EC limit; A5 Calc MAC=600 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		None allocated at this time
EC Risk Classification		Xn - Harmful: R43 N - Dangerous for the environment: R50, R53
EC Safety Classification		S2, S24, S37, S61
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		IV	-	Caution - Not acutely toxic
UN Number		Usually 3077
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for bensulfuron-methyl

Language	Name
English	bensulfuron-methyl
French	bensulfuron-methyle
German	Bensulfuron-methyl
Danish	bensulfuron-methyl
Italian	bensulfuron-metile
Spanish	bensulfuron-metil
Greek	-
Slovenian	bensulfuron-metil
Polish	bensulfuron metylowy
Swedish	-
Hungarian	benszulforon-metil
Dutch	-

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Record last updated: Saturday 12 December 2015
Contact: aeru@herts.ac.uk