Fluometuron

Fluometuron	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A soil applied selective herbicide used to control annual grasses and broad-leaved weeds

Example pests controlled

Annual grasses, Broad-leaved weeds

Example applications

Cotton; Sugarcane

Efficacy & activity

Availability status

Current

Introduction & key dates

1964, first reported; 1970s, first marketed

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

Approved

Dossier rapporteur/co-rapporteur

Spain/Belgium

Date EC 1107/2009 inclusion expires

31/05/2021

EU Candidate for substitution (CfS)

Yes - low ADI / ARfD / AOEL

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

C₁₀H₁₁F₃N₂O

Canonical SMILES

CN(C)C(=O)NC1=CC=CC(=C1)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RZILCCPWPBTYDO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H11F3N2O/c1-15(2)9(16)14-8-5-3-4-7(6-8)10(11,12)13/h3-6H,1-2H3,(H,14,16)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fluometuron	-

General status

Pesticide type

Herbicide

Substance group

Phenylurea

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Photosynthetic electron transport inhibitor at the photosystem II. Bleaching: 4-HPPD.

CAS RN

2164-17-2

EC number

218-500-4

CIPAC number

159

US EPA chemical code

035503

PubChem CID

16562

Molecular mass

232.20

PIN (Preferred Identification Name)

IUPAC name

1,1-dimethyl-3-(α,α,α-trifluoro-m-tolyl)urea

CAS name

N,N-dimethyl-N'-(3-(trifluoromethyl)phenyl)urea

Other status information

Potential groundwater contaminant

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

Physical state

White crystalline powder

Formulations

Property

Value

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

Fluometron 50 SC
Cottonex 50 SC
Cotoran 50 SC

Example products using this active

BASF
Makhteshim
Nufarm

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)

111

Moderate

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

109000

Methanol

144000

Acetone

1980

Xylene

20600

n-Octanol

Melting point (°C)

152.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.91 X 10⁰²

Calculated

Log P

2.28

at 23.5 °C

Low

Bulk density (g ml⁻¹)

1.39

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.125

Low volatility

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

2.63 X 10^-04

Non-volatile

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

Neutral solution: 243nm = 17300, 279nm = 1230
Acidic solution: 243nm = 17700, 279nm = 1390
Basic solution: 243nm = 17400, 279nm = 1360

Surface tension (mN m⁻¹)

61.5

at 25°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

63.6

Moderately persistent

DT₅₀ (lab at 20 °C)

63.6

Moderately persistent

DT₅₀ (field)

89.8

Moderately persistent

DT₉₀ (lab at 20 °C)

202.0

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 22.5-235.1 days, DT₉₀ range 74.8-384.1 days, field studies DT₅₀ range 62.5-117 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

6.0

Note

Ryegrass leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Stable pH 5 and pH 7 at 25 °C

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

524

Stable

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

0.87

Mobile

K_foc

67.4

¹/_n

0.963

Notes and range

EU dossier K_f range 0.079-2.809, kfoc range 30.8-117 mL g⁻¹, ¹/_n range 0.886-1.129, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

4.24

Calculated

High leachability

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

Value

1.69 X 10⁰⁰

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

desmethyl fluometuron (Ref: CGA 41686)

Soil

0.547

Major fraction, Relevant

m-trifluoromethylaniline (Ref: CGA 72903)

Soil

0.159

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: CGA 41690

Plant

trifluroactetic acid
Note: Toxicologically relevant; Oral LD50 200 mg/kg

TFAA

Plant (cotton)

hydroxylated di-desmethyl fluometuron (Ref: CGA 236431)

Rat; Plant (cotton)

hydroxylated desmethyl fluometuron (Ref: CGA 236432)

Rat; Plant (cotton)

hydroxylated n-acetyl

Rat

hydroxylated fluometuron (Ref: CGA 13211)

Rat; Plant (cotton)

di-desmethyl fluometuron (Ref: CGA 41698)

Rat; Plant

trifluromethylanaline

TFMA

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

40.4

Whole fish

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

2974

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1597 mg kg bw⁻¹ day⁻¹

Colinus virginianus chicks

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.3

Oncorhynchus mykiss

Moderate

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

Daphnia magna

Moderate

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

Daphnia magna

Low

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

6.8

Americamysis bahia

Moderate

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)

0.2

Lemna gibba

Moderate

Non-target plants

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

0.32

Pseudokirchneriella subcapitata

Moderate

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

0.0661

Pseudokirchneriella subcapitata

Moderate

Honeybees (Apis spp.)

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

> 100

Low

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

> 34.0

Moderate

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)

> 500

Eisenia foetida corr

Moderate

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

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

57.5

Folsomia candida 28d corr

Chronic NOEC (mg kg⁻¹)

6.7

Folsomia candida 28d corr

Other arthropod (1)

LR₅₀ g ha⁻¹

28.9

Reproductive effect
Typhlodromus pyri

% Effect

12.9

Mortality [Dose: 2.0 kg ha⁻¹]

Other arthropod (2)

LR₅₀ g ha⁻¹

398

Fecundity
Aphidius rhopalosiphi

% Effect

5.0

Mortality [Dose: 2.0 kg ha⁻¹]

Soil micro-organisms

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

Dose: 5x 2 kg ha⁻¹ 28days

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)

> 4.62

Rat

Other Mammal toxicity endpoints

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

0.0005

Rat SF=1000

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

0.008

Rat SF=100

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

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

0.008

Rat SF=100

Dermal penetration studies (%)

0.6-6.0

concentration dependent

Dangerous Substances Directive 76/464

List II

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)

0.1

EU Dir 89/778/EC limit; Calc MAC=6.6 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

Eye irritant

Phototoxicant

No data found

General human health issues

Exposure may lead to convulsions or coma
May cause reduced blood pressure
May cause haemolytic anaemia
IARC Group 3 carcinogen; USEPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
Reproduction risk category 3: R63
Xn - Harmful: R64
N - Dangerous for the environment: R51, R53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

fluometuron

French

fluometuron

German

Fluometuron

Danish

fluometuron

Italian

fluometuron

Spanish

fluometuron

Greek

Polish

fluometuron

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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