Flurtamone (Ref: RPA 590515)

Flurtamone (Ref: RPA 590515)	Last updated: 01/02/2021
(Also known as: SX 1802; RE 40885)

SUMMARY

Flurtamone is not an approved herbicide under EU regulations but still used in other parts of the world to control broad-leaved weeds and grasses. It has a low aqueous solubility, low volatility and, based on its chemical properties, is not expected to leach to groundwater. It is not normally persistent in soil or water-sediment systems. It has a low mammalian toxicity and no serious health risks have been identified from the literature. It has a low to moderate toxicity to most terrestrial and aquatic species, with the exception of aquatic plants for which toxicity is high.

GENERAL INFORMATION

Description

A pre-emergence or post-emergence herbicide used pre-planting and soil incorporated to control broad-leaved and some grasses

Example pests controlled

Broad-leaved weeds, Grasses

Example applications

Cereals including barley, wheat, oats, rye; Sunflower; Cotton; Peas

Efficacy & activity

Many products using flurtamone have been in use in the EU more many years with efficiacy proven in the field and under test conditions.

Availability status

Current

Introduction & key dates

circa 1990

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

Not applicable

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Czech Republic/Ireland

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

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms

Chemical formula

C₁₈H₁₄F₃NO₂

Canonical SMILES

CNC1=C(C(=O)C(O1)C2=CC=CC=C2)C3=CC(=CC=C3)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NYRMIJKDBAQCHC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H14F3NO2/c1-22-17-14(12-8-5-9-13(10-12)18(19,20)21)15(23)16(24-17)11-6-3-2-4-7-11/h2-10,16,22H,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flurtamone	Unstated isomer

General status

Pesticide type

Herbicide

Substance group

Pyridazinone

Minimum active substance purity

982 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Bleaching: inhibition of carotenoid biosynthesis.

CAS RN

96525-23-4

EC number

None allocated

CIPAC number

569

US EPA chemical code

PubChem CID

91755

Molecular mass

333.30

PIN (Preferred Identification Name)

IUPAC name

(RS)-5-methylamino-2-phenyl-4-(α,α,α-trifluoro-m-tolyl)furan-3(2H)-one

CAS name

5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3(2H)-furanone

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

Physical state

Pale yellow powder

Related substances & organisms

diflufenican

Formulations

Property

Value

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

Bacara
Graduate
Ingot
Chevron
Dolmen

Example products using this active

Bayer CropScience
Aventis
Rhone-Poulenc

Formulation and application details

Usually supplied as a soluble concentrate applied as an aqueous sloution using standard spraying equipment. at 0.5 L product in 200-400 L water / ha

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

10.7

at pH5

Low

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

350000

Acetone

199000

Methanol

Hexane

133000

Ethyl acetate

Melting point (°C)

148.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

190

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.74 X 10⁰³

Calculated

Log P

3.24

High

Bulk density (g ml⁻¹)

1.38

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

7.0 X 10^-07

Low volatility

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

2.03 X 10^-08

Non-volatile

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

Neutral solution: 276.2nm=28128
Acidic solution: 272.6nm=23912
Basic solution: 215.6nm=17530, 272.6nm=18755

Surface tension (mN m⁻¹)

72.1

at 20 °C 99.1%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not considered to be readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

10.7

Non-persistent

DT₅₀ (lab at 20 °C)

10.7

Non-persistent

DT₅₀ (field)

35.8

Moderately persistent

DT₉₀ (lab at 20 °C)

250

Persistent

DT₉₀ (field)

184

DT₅₀ modelling endpoint

Note

EU 2017 dossier lab studies DT₅₀ range 9.1-11.7 days, DT₉₀ range 30.2-39.9 days, Soils=4; field studies DT₅₀ range 46-65 days, DT₉₀ range 152-216 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

1.0

Moderately fast

Note

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)

82.4

Moderately fast

Water phase only DT₅₀ (days)

16.0

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

6.95

Moderately mobile

K_foc

257.3

¹/_n

0.876

Notes and range

EU 2016 dossier K_f range 4.47-10.62 mL g⁻¹, K_foc range 225-288 mL g⁻¹, ¹/_n range 0.87-0.86, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.47

Calculated

Transition state

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

Value

1.40 X 10^-01

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

trifluoroethanoic acid

Soil

0.055

Minor fraction, Relevant

3-trifluoromethylbenzoic acid (Ref: RE-54488)

Soil

0.247

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

benzoic acid

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

27.5

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)

6.3

Rat

High

(ppm diet)

100

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

247

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2530

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 6000 mg kg feed⁻¹

Colinus virginianus

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

7.3

Colinius virginianus NOEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

6.64

Pimephales promelas

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.63

Oncorhynchus mykiss

Moderate

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

Daphnia magna

Moderate

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

0.071

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)

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

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

0.0141

Lemna gibba

Moderate

Non-target plants

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

0.073

Pseudokirchneriella subcapitata

Moderate

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

0.024

Navicula pelliculosa

Moderate

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)

> 105.1

Apis mellifera

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)

> 100

Bombus terrestris

Low

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)

> 1800

Eisenia foetida

Low

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

47.5

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

500

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

33.8

Mortality [Dose: 0.25 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

92.1

Mortality [Dose: 0.25 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: <5% slight stimulation of soil respiration

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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.2

Rat 4hr (whole body)

Other Mammal toxicity endpoints

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

0.03

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

None allocated

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

0.19

Rat SF=300

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

0.02

Dog 1 year SF=100

Dermal penetration studies (%)

0.3-8.0%

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks for bystanders identified

Occupational

No unacceptable risks to operators or workers identified

MRLs

European

EU MRL pesticide database

Notes

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible kidney, liver and spleen toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S61, S60

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

flurtamone

French

flurtamone

German

Flurtamone

Danish

flurtamon

Italian

flurtamone

Spanish

flurtamone

Greek

flurtamone

Polish

flurtamon

Swedish

flurtamon

Hungarian

Dutch

flurtamone

Record last updated:	01/02/2021
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