Mesosulfuron-methyl (Ref: AE F130060)

Mesosulfuron-methyl (Ref: AE F130060)	Last updated: 08/11/2019
(Also known as: mesosulfuron)

GENERAL INFORMATION

Description

A systemic herbicide used for post-emergence control of grasses and other weeds in cereals

Example pests controlled

Grasses including blackgrass; Broad-leaved weeds

Example applications

Cereals including spring wheat, winter wheat, durum wheat, winter rye

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 2001

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/06/2032

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Poland

Date EC 1107/2009 inclusion expires

30/06/2032

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

Chemical structure

Isomerism

Chemical formula

C₁₇H₂₁N₅O₉S₂

Canonical SMILES

COC1=CC(=NC(=N1)NC(=O)NS(=O)(=O)C2=C(C=CC(=C2)CNS(=O)(=O)C)C(=O)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NIFKBBMCXCMCAO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H21N5O9S2/c1-29-13-8-14(30-2)20-16(19-13)21-17(24)22-33(27,28)12-7-10(9-18-32(4,25)26)5-6-11(12)15(23)31-3/h5-8,18H,9H2,1-4H3,(H2,19,20,21,22,24)/f/h21-22H

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

>955 g kg⁻¹

Known relevant impurities

EU dossier: None disclosed

Substance origin

Synthetic

Mode of action

Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

208465-21-8

EC number

CIPAC number

663.201

US EPA chemical code

122009

PubChem CID

11409499

Molecular mass

503.51

PIN (Preferred Identification Name)

methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-a-(methanesulfonamido)-p-toluate

IUPAC name

methyl 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-a-(methanesulfonamido)-p-toluate

CAS name

methyl 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-4-[[(methylsulfonyl)amino]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

Alopecurus myosuroides

Physical state

Pale yellow crystalline solid

Related substances & organisms

iodosulfuron-methyl-sodium

mefenpyr

mesosulfuron

Formulations

Property

Value

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

Atlantis WG
Othello
Pacifica
Atlantis

Example products using this active

Bayer CropScience
Teliton

Formulation and application details

Often supplied as an oil suspension

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

483

Moderate

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

200

Hexane

13660

Acetone

2000

Ethyl acetate

130

Toluene

Melting point (°C)

195.4

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

190

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.31 X 10^-01

Calculated

Log P

-0.48

Low

Bulk density (g ml⁻¹)

1.48

Dissociation constant pKa) at 25 °C

4.35

Vapour pressure at 20 °C (mPa)

1.10 X 10^-05

Low volatility

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

3.65 X 10^-12

Non-volatile

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

203nm = 53566, 237nm = 22220, 291nm = 904

Surface tension (mN m⁻¹)

61.9

at 20 °C 19.27 mg l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

43.5

Moderately persistent

DT₅₀ (lab at 20 °C)

43.5

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

345.5

Persistent

DT₉₀ (field)

257

DT₅₀ modelling endpoint

Note

EU 2016 dossier Lab studies DT₅₀ range 7.6-140.1 days, DT₉₀ range 25.3- >1000 days, Soils=9

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

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

253

Persistent

Note

pH and temperature sensitive: DT₅₀ 7.2 days at pH 5 and 20 °C, 3.5 days at pH 5 and 25 °C, 253 days at pH 7 and 25 °C, 23 days at pH 7 and 40 °C, 318 days at pH 9 and 25 °C, 27 dats at pH 9 and 40 °C

Water-sediment DT₅₀ (days)

48.9

Moderately fast

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

1.27

Moderately mobile

K_foc

¹/_n

0.91

Notes and range

EU dossier K_f 0.24-3.71 ml/g; K_foc range 26-345 mL g⁻¹; ¹/_n range 0.85-0.93; Soils=9

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.85

Calculated

High leachability

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

Value

9.95 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-amino-4,6-dimethoxypyrimidine (Ref: AE-F092944)

Soil

0.101

Major fraction, Relevant

4,6-dimethoxypyrimidine-2-yl-urea (Ref: AE-F099095)

Soil

0.292

Major fraction, Relevant

mesosulfuron (Ref: AE F154851)

Soil

0.162

Major fraction, RelevancT

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

O-desmethyl mesosulfuron (Ref: AE F160459)

a = Soil (Anaerobic); b = Water/sediment

a=0.259

benzisothiazole (Ref: AE F147447)

Water (Hydrolysis); Water/sediment

0.374

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)

> 840

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Colinus virginianus

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

Colinius virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 100

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

32.0

Oncorhynchus mykiss

Low

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

> 100

Daphnia magna

Low

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

1.8

Daphnia magna

Moderate

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)

0.00062

Lemna gibba

High

Non-target plants

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

0.2

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

Apis mellifera

Low

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

> 105.6

Apis mellifera

Low

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)

> 100

Bombus terrestris

Low

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)

125

Eisenia foetida 56 days

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

>= 1000

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

17.5

Mortality [Dose: 15 g ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

8.3

Mortality [Dose: 15 g ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 0.075 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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.33

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

1.0

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)

0.2

Dog SF=100

Dermal penetration studies (%)

9.3-13.9

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

mesosulfuron-methyl

French

mesosulfuron-methyle

German

Mesosulfuron

Danish

mesosulfuron

Italian

mesosulfuron-metile

Spanish

mesosulfuron-metil

Greek

Polish

mezosulfuron metylowy

Swedish

mesosulfuronmetyl

Hungarian

Dutch

Record last updated:	08/11/2019
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