Metosulam (Ref: XDE 511)

Metosulam (Ref: XDE 511)	Last updated: 31/10/2024
(Also known as: metosulame; DE 511; XRD 511)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: GUS: High leachability	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A post-emergence, broad-spectrum foliar herbicide used to control broad-leaved weeds in cereals and other crops

Example pests controlled

Broad-leaved weeds

Example applications

Cereals; Grain legumes; Pasture; Alfalfa; Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

1993, first reported; 1994, launched Turkey

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

No data

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Norway

Date EC 1107/2009 inclusion expires

Expired

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Australia

Chemical structure

Isomerism

None

Chemical formula

C₁₄H₁₃Cl₂N₅O₄S

Canonical SMILES

CC1=C(C(=C(C=C1)Cl)NS(=O)(=O)C2=NN3C(=CC(=NC3=N2)OC)OC)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

VGHPMIFEKOFHHQ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H13Cl2N5O4S/c1-7-4-5-8(15)12(11(7)16)20-26(22,23)14-18-13-17-9(24-2)6-10(25-3)21(13)19-14/h4-6,20H,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Triazolopyrimidine herbicide; Sulfonanilide herbicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, absorbed by roots and shoots. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.

CAS RN

139528-85-1

EC number

410-240-1

CIPAC number

707

US EPA chemical code

PubChem CID

86422

CLP index number

616-214-00-8

Molecular mass

418.26

PIN (Preferred Identification Name)

IUPAC name

2',6'-dichloro-5,7-dimethoxy-3'-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonanilide

CAS name

N-(2,6-dichloro-3-methylphenyl)-5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Echium plantagineum, Raphanus raphanistrum

Physical state

Cream powder

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Tacco SC100
Metosulam SC100

Formulation and application details

Usually supplied as a suspension concentrate that is 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)

700

High

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

7800

Acetone

1000

Ethyl acetate

1900

Methanol

200

Toluene

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

190

Flashpoint (°C)

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

2.88 X 10⁰²

Calculated

Log P

2.46

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.49

Dissociation constant pKa) at 25 °C

5.5

Weak acid

Vapour pressure at 20 °C (mPa)

1.0 X 10^-09

25 °C

Low volatility

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

8.00 X 10^-13

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral sol: 212nm = 67000
Acid sol: 206nm = 55000
Basic sol: 212nm = 71000

Surface tension (mN m⁻¹)

69.6

at 20°C 96%

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)

8.1

Non-persistent

DT₅₀ (field)

38.8

Moderately persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

112

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 4.2-33.3 days, DT₉₀ range 16.3-144 days; field studies DT₅₀ range 20-47 days, DT₉₀ range 660-156 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

31.1

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9, 25 °C, 30 days

Water-sediment DT₅₀ (days)

8.2

Fast

Water phase only DT₅₀ (days)

6.7

Moderately fast

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

3.61

Moderately mobile

K_foc (mL g⁻¹)

166

¹/_n

0.921

Notes and range

EU dossier kf range 0.927-8.841, kfoc range 51.5-264.7 mL g⁻¹, ¹/_n range 0.843-1.084, Soils=4

pH sensitivity

Adsorption increase as soils pH decreases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.83

Calculated

High leachability

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

Value

2.28 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

38.4

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

No dat

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

5-amino-N-(2,6-dichloro-3-methylphenyl)-1H-1,2,4-triazole-3-sulfonamide

Major fraction

0.263

N-(2,6-dichloro-3-methylphenyl)-5-methoxy-7-hydroxy-1,2,4-triazolo(1,5-alpha)pyrimidine-2-sulfonamide

Major fraction

0.218

5,7-OH-metosulam

Minor fraction

Mol wt = 390.2; Koc = 0.1 mL/g

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

4-OH-metosulam sulphate; metosulam metabolite M11

Rat

4-OH-metosulam gucoside; metosulam metabolite M08

Rat

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1923 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

Eisenia foetida

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

1000

Eisenia foetida

Non-target plants

4.89

Rape
Seedling emergence, ER₅₀
as g ha⁻¹

1.46

Tomato
Vegetative vigour, ER₅₀
as g ha⁻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)

106

Apis mellifera

Low

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

Chronic

Notes

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as % Mortality at dose 0.04 g ha⁻¹

-16.7

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 40.0

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 40.0

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 0.04 g ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 29.3

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

24.4

Oncorhynchus mykiss

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

> 100

Daphnia magna

Low

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

2.5

Daphnia magna

Moderate

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

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)

0.0023

Lemna gibba

High

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

0.075

Scenedesmus subspicatus

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

1.9

Rat

Other Mammal toxicity endpoints

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

0.05

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.25

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.02

Dermal penetration studies (%)

0.02-4.3

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Protective clothing required to mitigate risks to operators
No foreseen risks to other workers

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible kidney and gall bladder toxicant
CLP data - suspected carcingen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H373, H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

metosulam

French

metosulam

German

Metosulam

Danish

metosulam

Italian

metosulam

Spanish

metosulam

Greek

Polish

metosulam

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	31/10/2024
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