Ethoxysulfuron (Ref: AE F095404)

Ethoxysulfuron (Ref: AE F095404)	Last updated: 23/05/2018
(Also known as: HOE 095404)

GENERAL INFORMATION

Description

A herbicide used for broad-leaved weed and sedge control in a range of crops including cereals and rice

Example pests controlled

Broad-leaved weeds, Sedge

Example applications

Cereals; Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1995

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Italy

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

Also used in

Australia

Chemical structure

Isomerism

Chemical formula

C₁₅H₁₈N₄O₇S

Canonical SMILES

CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UWVKRNOCDUPIDM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H18N4O7S/c1-4-25-10-7-5-6-8-11(10)26-27(21,22)19-15(20)18-14-16-12(23-2)9-13(17-14)24-3/h5-9H,4H2,1-3H3,(H2,16,17,18,19,20)/f/h18-19H

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, inhibits plant cell growth. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

126801-58-9

EC number

CIPAC number

591

US EPA chemical code

PubChem CID

3623881

Molecular mass

398.39

PIN (Preferred Identification Name)

2-ethoxyphenyl [(4,6-dimethoxypyrimidin-2-yl)carbamoyl]sulfamate

IUPAC name

1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethoxyphenoxysulfonyl)urea

CAS name

2-ethoxyphenyl [[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]sulfamate

Other status information

Chemical subject to PIC regulations

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

Cyperus difformis, Lindernia dubia, Scirpus mucronatus

Physical state

White-beige powder

Formulations

Property

Value

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

Example products using this active

Bayer CropScience

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

5000

High

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

n-Hexane

2500

Toluene

36000

Acetone

7700

Methanol

Melting point (°C)

150

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.02 X 10⁰¹

Calculated

Log P

1.01

Low

Bulk density (g ml⁻¹)

1.44

Dissociation constant pKa) at 25 °C

5.28

Weak acid

Vapour pressure at 20 °C (mPa)

0.066

Low volatility

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

1.94 X 10^-03

Non-volatile

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

194nm = 74000

Surface tension (mN m⁻¹)

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)

Non-persistent

DT₅₀ (field)

17.5

Non-persistent

DT₉₀ (lab at 20 °C)

114

Persistent

DT₉₀ (field)

57.5

DT₅₀ modelling endpoint

Note

EU dossier DT₅₀ range 6-18 days (soil), 51 days (flooded paddy fields), DT₉₀ range 59 - 169 days, Field data DT₅₀ range 14 – 21 days, DT₉₀ range 46 – 69 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

Stable in distilled, sterile water but photodegradation rapid in natural waters

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

Value

259

Persistent

Note

Stable in neutral and slightly alkaline conditions but hydrolyses in slightly acidic conditions

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

134

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.33

Calculated

Transition state

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

Value

8.95 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

1-(2-ethoxyphenoxysulfonyl)-3-(6-hydroxy-4-methoxypyrimidin-2-yl)-urea (Ref: AE-F126663)

Soil

0.428

Major fraction, Relevancy unknown

1-(2-ethoxyphenoxysulfonyl)-3-guanylurea or 3-amidino-1(2-ethoxyphenoxysulfonyl)-urea) (Ref: AE-F136086)

Soil

0.190

Major fraction, Relevancy unknown

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

Soil

0.180

Major fraction, Relevancy unknown

1-(N-hydroxymethylcarbonyl-N-methoxycarbonylguanyl)-3-(2-ethoxyphenyl-sulfonyl)urea

Soil

0.312

Major fraction, Relevancy unknown

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)

3270

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

5.6

Dog

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 80

Cyprinus carpio

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 22.8

Oncorhynchus mykiss

Low

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

307

Daphnia magna

Low

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

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)

3.2

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.00024

Lemna minor

High

Non-target plants

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

0.19

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)

> 200

Low

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

> 1000

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)

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

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

% Effect

-79.8

Beneficial capacity [Dose: 0.06 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-54.3

Beneficial capacity [Dose: 0.06 kg as/ha]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: Tolerable effects
Carbon mineralisation: Tolerable effects

Dose: Not stated

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)

3270

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

4000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

3.55

Rat

Other Mammal toxicity endpoints

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

0.04

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)

0.06

Rat

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

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

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

ethoxysulfuron

French

ethoxysulfuron

German

Ethoxysulfuron

Danish

ethoxysulfuron

Italian

etoxisulfuron

Spanish

etoxisulfuron

Greek

Polish

etoksysulfuron

Swedish

Hungarian

Dutch

ethoxysulfuron

Record last updated:	23/05/2018
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