Chlorimuron-ethyl (Ref: DPX F6025)

Chlorimuron-ethyl (Ref: DPX F6025)	Last updated: 04/01/2021
(Also known as: chlorimuron ethyl ester; HSDB 6850)

SUMMARY

Chlorimuron-ethyl is a post-emergence, foliar applied herbicide without EU regulatory approval for use. It has a high aqueous solubility, is non-volatile and, based on its chemical properties, is mobile and can be expected to leach to groundwater. It can be moderately persistent in soil systems but will not usually persist in aquatic systems. It is generally susceptible to hydrolysis. It has a low mammalian toxicity and has a high potential to bioaccumulate. It is relatively non- toxic to most aquatic species, birds and earthworms but moderately toxic to honey bees.

GENERAL INFORMATION

Description

Post-emergence, foliar applied herbicide used to control broad-leaved weeds in a range of crops including peanuts and soya beans.

Example pests controlled

Ragweed; Pigweed; Velvetleaf; Dandelion; Yellow nutsedge; Bittercress; Deadnettle; Lambsquarters; Thistles; Pennycress

Example applications

Soybeans; Peanuts

Efficacy & activity

Availability status

Unknown

Introduction & key dates

1986

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

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

Chemical structure

Isomerism

Chemical formula

C₁₅H₁₅ClN₄O₆S

Canonical SMILES

CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)Cl)OC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NSWAMPCUPHPTTC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H15ClN4O6S/c1-3-26-13(21)9-6-4-5-7-10(9)27(23,24)20-15(22)19-14-17-11(16)8-12(18-14)25-2/h4-8H,3H2,1-2H3,(H2,17,18,19,20,22)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
chlorimuron-ethyl	-

General status

Pesticide type

Herbicide

Substance group

Sulfonylurea

Minimum active substance purity

95%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS

CAS RN

90982-32-4

EC number

CIPAC number

None allocated

US EPA chemical code

128901

PubChem CID

56160

Molecular mass

414.82

PIN (Preferred Identification Name)

ethyl 2-{[(4-chloro-6-methoxypyrimidin-2-yl)carbamoyl]sulfamoyl}benzoate

IUPAC name

ethyl 2-(4-chloro-6-methoxypyrimidin-2-ylcarbamoylsulfamoyl)benzoate

CAS name

ethyl 2-[[[[(4-chloro-6-methoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]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

Amaranthus hybridus, Amaranthus powellii

Physical state

Colourless to off-white crystals

Related substances & organisms

flumioxazin

metribuzin

thifensulfuron-methyl

tribenuron-methyl

Formulations

Property

Value

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

Darban
Twister
Classic
Pilarclas
Sponsor

Example products using this active

AgroCare
DuPont
Cheminova
FCC
United Phosphorus

Formulation and application details

Usually supplied as a flowable dry powder and used as an aqueous spray post-emergence

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1200

High

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

70500

Acetone

8150

Benzene

n-Hexane

2830

Xylene

Melting point (°C)

181

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.29 X 10⁰⁰

Calculated

Log P

0.11

Low

Bulk density (g ml⁻¹)

1.51

Dissociation constant pKa) at 25 °C

4.2

Weak acid

Vapour pressure at 20 °C (mPa)

4.9 X 10^-07

Low volatility

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

1.7 X 10^-10

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Literature studies give field DT₅₀ 14-42 days; Degradation takes longer at higher pH.

Dissipation rate RL₅₀ on plant matrix

Value

4.7

Note

Wheat straw, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Non-persistent

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

106

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

2.86

Calculated

High leachability

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

Value

2.15 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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)

> 4102

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Dog

(ppm diet)

250

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5620

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 8.4

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 10

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

0.00045

Lemna gibba

High

Non-target plants

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

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)

12.5

Moderate

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

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)

4050

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

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

> 4102

Rat

Low

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr

Other Mammal toxicity endpoints

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

0.02

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Occupational exposure may occur through dermal contact

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

Slightly toxic
Possible liver toxicant

Handling issues

Property

Value and interpretation

General

Highly flammable

CLP classification 2013

Handling: H225
Health: H319, H336

EC Risk Classification

Xi - Irritant: R36
H - Handling risks: R11, R67

EC Safety Classification

S2, S9, S26/59, S46

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

chlorimuron-ethyl

French

German

Danish

Italian

Spanish

clorimuron etil

Greek

Polish

chlorimuron etylowy

Swedish

Hungarian

Dutch

Record last updated:	04/01/2021
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