Bensulfuron-methyl (Ref: DPX F5384)

Bensulfuron-methyl (Ref: DPX F5384)	Last updated: 12/01/2021
(Also known as: methyl bensulfuron; DPX 84; F 5384)

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

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

Efficacy & activity

Availability status

Current

Introduction & key dates

1985

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Italy/Spain

Date EC 1107/2009 inclusion expires

31/10/2022

EU Candidate for substitution (CfS)

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

Australia, USA

Chemical structure

Isomerism

Chemical formula

C₁₆H₁₈N₄O₇S

Canonical SMILES

COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)CC2=CC=CC=C2C(=O)OC)OC

Isomeric SMILES

No data

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)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
bensulfuron-methyl	-

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

PubChem CID

54960

Molecular mass

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

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

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

Londax
Sectar
Testar

Example products using this active

United Phosphorus
DuPont

Formulation and application details

Usually supplied as water dispersible granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Moderate

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

5100

Acetone

18400

Dichloromethane

1750

Ethyl acetate

229

o-Xylene

Melting point (°C)

179.4

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

245

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.17 X 10⁰⁰

Calculated

Log P

0.79

Low

Bulk density (g ml⁻¹)

1.41

Dissociation constant pKa) at 25 °C

5.2

Weak acid

Vapour pressure at 20 °C (mPa)

2.80 X 10^-09

Low volatility

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

2.00 X 10^-11

Non-volatile

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

Surface tension (mN m⁻¹)

74.9

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

8.2

Non-persistent

DT₉₀ (lab at 20 °C)

287.6

Persistent

DT₉₀ (field)

16.7

DT₅₀ modelling endpoint

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

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

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 20 °C and pH 7

Value

Stable

Note

Sensitive to pH: DT₅₀ 6.1 days at pH 4, 141 days at pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

18.5

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

6.6

Moderately mobile

K_foc

409

¹/_n

0.92

Notes and range

EU dossier kf range 2.5-8.4 mL g⁻¹, K_foc range 205-684 mL g⁻¹, ¹/_n range 0.88-1.08, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.27

Calculated

Low leachability

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

Value

1.37 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 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-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)carbamoyl]sulfamoyl}acetic acid (Ref: IN-DAT97)

a = Water/sediment; b = Groundwater

a=0.099

(4,6-dimethoxypyrimidin-2-yl)urea (Ref: IN-T5831)

a = Water (Photolysis); b = Groundwater

a=0.137

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1.6

Low potential

CT₅₀ (days)

327

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

21.4

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2510

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1690 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 66

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

1.5

Oncorhynchus mykiss

Moderate

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

130

Daphnia magna

Low

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

Daphnia magna

Low

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

130

Americamysis bahia

Low

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

125.0

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

Lemna gibba

High

Non-target plants

> 2.41

Oilseed rape
Seedling emergence, ER₅₀
as g ha⁻¹

> 2.08

Soybean
Vegetative vigour, ER₅₀
as g ha⁻¹

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

0.02

Raphidocelis subcapitata

Moderate

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)

> 100

Low

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

> 51.4

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)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

600

> 48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

600

> 7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 5 x field rate

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)

7.5

Rat 4 hr

Other Mammal toxicity endpoints

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

0.2

Dog 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)

0.12

Dog SF=167

Dermal penetration studies (%)

5.9-7.2

concentration dependent

Dangerous Substances Directive 76/464

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

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=600 µg l⁻¹

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

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

Health: H317
Environment: H411

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)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

bensulfuron-methyl

French

bensulfuron-methyle

German

Bensulfuron-methyl

Danish

bensulfuron-methyl

Italian

bensulfuron-metile

Spanish

bensulfuron-metil

Greek

Polish

bensulfuron metylowy

Swedish

Hungarian

benszulforon-metil

Dutch

Record last updated:	12/01/2021
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