Ethametsulfuron-methyl (Ref: DPX-A7881)

Ethametsulfuron-methyl (Ref: DPX-A7881)	Last updated: 29/08/2024
(Not known by any other names)

SUMMARY

Ethametsulfuron-methyl is a selective herbicide. It is moderately soluble in water, volatile and, based on its chemical properties, presents a high risk of leaching to groundwater. It is relatively persistent in both soil and aqueous systems. It has a low mammalian toxicity but may bio-accumulate. It has a low toxicity to birds and most aquatic species, the exception being aquatic plants including algae. It is moderately toxic to honeybees.

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 Moderate alert: GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Fish chronic ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

An effective herbicide for the control of wild mustard, stinkweed and other broad-leaved weeds especially in OSR

Example pests controlled

Charlock mustard (Sinapis arvensis); Pennycress (Thlaspi arvense); Other broad-leaved weeds

Example applications

Oilseed rape

Efficacy & activity

Availability status

Current

Introduction & key dates

1989, introduced

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

United Kingdom

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

No data

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

C₁₅H₁₈N₆O₆S

Canonical SMILES

CCOC1=NC(=NC(=N1)NC)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

ZINJLDJMHCUBIP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H18N6O6S/c1-4-27-15-19-12(16-2)17-13(20-15)18-14(23)21-28(24,25)10-8-6-5-7-9(10)11(22)26-3/h5-8H,4H2,1-3H3,(H3,16,17,18,19,20,21,23)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Triazinylsulfonylurea herbicide

Minimum active substance purity

>971g kg⁻¹

Known relevant impurities

EU dossier: IN-D7556 <3g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

97780-06-8

EC number

619-290-0

CIPAC number

834.201

US EPA chemical code

129091

PubChem CID

91756

CLP index number

No data found

Molecular mass

410.41

PIN (Preferred Identification Name)

methyl 2-({[4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)benzoate

IUPAC name

methyl 2-[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate

CAS name

methyl 2-(((((4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoate

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

Sinapis arvensis, Thlaspi arvense

Physical state

White crystalline solid

Formulations

Property

Value

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

Example products using this active

Salsa WG

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

223

Moderate

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

764

Acetone

2066

Dichloromethane

3.0

n-Hexane

173

Ethyl acetate

Melting point (°C)

197

Boiling point (°C)

317

Degradation point (°C)

Does not degrade below boiling point.

Flashpoint (°C)

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

5.25 X 10^-01

Calculated

Log P

-0.28

Low

Fat solubility of residues

Solubility

Not applicable

Data type

Regulatory data - residue concentrations negligible

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

4.2

Weak acid

Vapour pressure at 20 °C (mPa)

6.41 X 10^-04

at 25 °C

Low volatility

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

1.22 X 10^-06

at 25 °C

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acid soln: 220nm=41432, no significant absorption>290nm
Neutral soln: 225nm=41432, no significant absorption>290nm
Basic soln: 225nm: 41187, no significant absorption>290nm

Surface tension (mN m⁻¹)

68.8

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

41.0

Moderately persistent

DT₅₀ (lab at 20 °C)

36.5

Moderately persistent

DT₅₀ (field)

22.6

Non-persistent

DT₉₀ (lab at 20 °C)

153.0

Persistent

DT₉₀ (field)

472

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 24.2-70.9 days, DT₉₀ range 91-320 days; Field studies DT₅₀ range 9.4-71.9 days, DT₉₀ range 162-795 days; Manufacturers published data gives field DT₅₀ 16-100 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

9.0

Note

Published literature RL₅₀ range 4.9-14.4 days, various matrices from swede, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Not a major degradation route

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

Value

Stable

Note

Stable pH 7 and pH 9, DT₅₀ 41 days at pH 5

Water-sediment DT₅₀ (days)

35.6

Moderately fast

Water phase only DT₅₀ (days)

26.6

Slow

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)

4.93

Moderately mobile

K_oc (mL g⁻¹)

220.7

Notes and range

EU dossier K_d range 0.22-19.4 mL g⁻¹, K_oc range 39.7-667.9 mL g⁻¹, soils=5

Freundlich

K_f (mL g⁻¹)

2.69

Moderately mobile

K_foc (mL g⁻¹)

119.4

¹/_n

0.899

Notes and range

EU dossier K_f range 0.20-1.47 mL g⁻¹, K_foc range 25.7-367.9 mL g⁻¹, ¹/_n range 0.783-975, Soils=5

pH sensitivity

Yes

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.60

Calculated

Transition state

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

Value

1.44 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

14,05

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Substance 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 data

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

ethametsulfuron (Ref: IN A8768)

Major fraction

0.315

N-(4-ethoxy-6-(methylamino)-1,3,5-triazin-2-yl)urea (Ref: IN B9161)

Major fraction

0.590

6-ethoxy-N-methyl-1,3,5-triazine-2,4-diamine (Ref: IN D7556)

Major fraction

0.259

methyl-2-(((4-amino-6-ethoxy-1,3,5,-triazin-2-yl)aminocarbonyl)aminosulfonyl)-benzoate (Ref: IN N7468)

Major fractiont

0.240

2(((((4-amino-6-ethoxy-1,3-5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoic acid (Ref: IN-RYM15)

1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN 00581)

Minor fraction

0.045

4-amino-(methylamino_-1,3-5-triazin-2(1H)-one (Ref: IN-A9795)

Major fraction

0.121

2-(aminosulfonyl)benzoic acid (Ref: IN-D5119)

Major fraction

0.124

methyl-2-(((4-hydroxy-6-(methylamino)-1,3,5-triazin-2-yl)-aminocarbonyl)aminosulfonyl)-benzoate (Ref: IN-N7469)

Major fraction

0.201

6-ethyoxy-1,3,5-triazine-2,4-diamine (Ref: IN-R7558)

Minor fraction

0.058

methyl-2-(((((6-amino-3,4-dihydro-4-oxo-1,3,5-triazin-2-yl)amino)carbonyl)sulfonyl)benzoate (Ref: IN-RXR81)

Minor fraction

0.092

methyl-2-(aminosulfonyl)benzoate (Ref: IN-D5803)

Minor fraction

0.080

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

ethametsulfuron (Ref: IN A8768)

Relevant

methyl-2-(((4-hydroxy-6-(methylamino)-1,3,5-triazin-2-yl)-aminocarbonyl)aminosulfonyl)-benzoate (Ref: IN-N7469)

Not relevant

methyl-2-(((((6-amino-3,4-dihydro-4-oxo-1,3,5-triazin-2-yl)amino)carbonyl)sulfonyl)benzoate (Ref: IN-RXR81)

Not relevant

2(((((4-amino-6-ethoxy-1,3-5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoic acid (Ref: IN-RYM15)

Not relevant

1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN-00581)

Not relevant

2-(aminosulfonyl)benzoic acid (Ref: IN-D5119)

Not relevant

methyl-2-(((4-amino-6-ethoxy-1,3,5,-triazin-2-yl)aminocarbonyl)aminosulfonyl)-benzoate (Ref: IN N7468)

Not relevant

6-ethyoxy-1,3,5-triazine-2,4-diamine (Ref: IN-R7558)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1,2-benzisothiazol-3(2H)-one,1,1-dioxide (Ref: IN 00581)
Note: CAS no. 81-07-2; C8H7NO

1,1-dioxide-1,2-benzisothiazol-3(2H)-one

Plant; Rat; Water

4-amino-(methylamino_-1,3-5-triazin-2(1H)-one (Ref: IN-A9795)
Note: CAS no. 850879-26-4; C4H7N5O

O-deethyl triazine amine

Plant

2-(aminosulfonyl)benzoic acid (Ref: IN-D5119)
Note: CAS no. 632-24-6; C7H7NO4S

Water

methyl-2-(((4-hydroxy-6-(methylamino)-1,3,5-triazin-2-yl)-aminocarbonyl)aminosulfonyl)-benzoate (Ref: IN-N7469)
Note: C13H14N6O6S

O-deethyl ethametsulfuron methyl

Plant; Rat; Water

6-ethyoxy-1,3,5-triazine-2,4-diamine (Ref: IN-R7558)
Note: CAS no. 2827-44-3: C5H9N5O

N-demethyl triazine amine

Plant

methyl-2-(((((6-amino-3,4-dihydro-4-oxo-1,3,5-triazin-2-yl)amino)carbonyl)sulfonyl)benzoate (Ref: IN-RXR81)
Note: CAS no. 164524-91-8; C12H12N6O6S

O-deethyl-N-demethylethametsulfuron methyl)

Plant

methyl-2-(aminosulfonyl)benzoate (Ref: IN-D5803)
Note: CAS no. 57683-71-3; C8H9NO4S

ester sulphonamide

Plant; Water

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)

(ppm diet)

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

> 1582

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

229.4

Coturnix japonica

Low

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

153.72

Eisenia foetida as product

Moderate

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

36.0

Eisenia foetida as product

Moderate

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

>= 250

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

4.62

Apis mellifera

Moderate

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

40.83

Apis mellifera

Moderate

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

Chronic

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)

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

> 18.75

Aphidius rhopalosiphi

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

11.37

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ 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)

> 126

Oncorhynchus mykiss

Low

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

5.4

Oncorhynchus mykiss 87 day

Moderate

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

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

> 108

Daphnia magna

Low

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

4.7

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)

0.0004

Lemna gibba

High

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

0.421

Pseudokirchneriella subcapitata

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.7

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

None allocated

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)

None allocated

Dermal penetration studies (%)

25-75

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

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

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not explected to auto-ignite, Not highly flammable

CLP classification 2013

Health: H319
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

ethametsulfuron-methyl

French

German

Danish

Italian

Spanish

etamatsulfuron metil

Greek

Polish

etametsulfuron metylowy

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	29/08/2024
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