Flutolanil (Ref: NNF 136)

Flutolanil (Ref: NNF 136)	Last updated: 12/01/2021
(Not known by any other names)

SUMMARY

Flutolanil is a systemic fungicide approved for use in the EU. It has a low aqueous solubility, volatile with a marginal risk of leaching to groundwater. It is persistent in both soils and aquatic systems. Although it has a low mammalian toxicity it does show some potential to bioaccumulate. No serious risks to human health have been identified. It is moderately toxic to birds and most aquatic organisms and earthworms but has a low toxicity to honeybees.

GENERAL INFORMATION

Description

A fungicide used to control a range of pathogens especially Rhizoctonia spp. on rice and other crops.

Example pests controlled

Basidiomycete fungi, Various Rhizoctonia diseases including brown patch, large patch, Blight, Snow Mould

Example applications

Potatoes; Rice; Turf; Cereals; Sugarbeet; Some ornamentals e.g. Tulip, Iris

Efficacy & activity

Efficiacy demonstrated during field trials. May be dependant on planting depth.

Availability status

Current

Introduction & key dates

1981, first reported; 1986, first introduced

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

28/02/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands/UK

Date EC 1107/2009 inclusion expires

28/02/2021

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, USA

Chemical structure

Isomerism

Chemical formula

C₁₇H₁₆F₃NO₂

Canonical SMILES

CC(C)OC1=CC=CC(=C1)NC(=O)C2=CC=CC=C2C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PTCGDEVVHUXTMP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H16F3NO2/c1-11(2)23-13-7-5-6-12(10-13)21-16(22)14-8-3-4-9-15(14)17(18,19)20/h3-11H,1-2H3,(H,21,22)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flutolanil	-

General status

Pesticide type

Fungicide

Substance group

Oxathiin

Minimum active substance purity

975 g/Kg

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with curative and protective action. Respiration inhibitor - Succinate DeHydrogenase Inhibitor.

CAS RN

66332-96-5

EC number

CIPAC number

524

US EPA chemical code

128975

PubChem CID

47898

Molecular mass

323.31

PIN (Preferred Identification Name)

IUPAC name

α,α,α-trifluoro-3'-isopropoxy-o-toluanilide

CAS name

N-(3-(1-methylethoxy)phenyl)-2-(trifluoromethyl)benzamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Rhino
Moncut 40SC
Monarch

Example products using this active

Certis
Nihon Nohyaku

Formulation and application details

Available in a variety of formulations including flowable concentrates that are mixed with water and applied as a spray or used for seed treatments and dry powders for treating potato tubers.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

8.01

Low

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

606000

Acetone

365000

Ethyl acetate

322000

Methanol

35000

Toluene

Melting point (°C)

103.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

300

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.48 X 10⁰³

Calculated

Log P

3.17

High

Bulk density (g ml⁻¹)

1.32

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.10 X 10^-04

Low volatility

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

1.65 X 10^-05

Non-volatile

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

Neutral solution: 208.5nm = 11709, 292nm = 33109
Acidic solution: 248nm=10739, 212.5nm=32126

Surface tension (mN m⁻¹)

71.3

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

400

Very persistent

DT₅₀ (lab at 20 °C)

400

Very persistent

DT₅₀ (field)

105

Persistent

DT₉₀ (lab at 20 °C)

1117

Very persistent

DT₉₀ (field)

718

DT₅₀ modelling endpoint

Note

EU 2018 dossier Lab studies DT₅₀ (normalised) range 115-1000 days, DT₉₀ range 383-1770 days, Soils=8; field studies DT₅₀ range 60.4-171 days, DT₉₀ range 286-1140 days, Soils=8

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

29.3

Note

Cucumber leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

277

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

320

Slow

Water phase only DT₅₀ (days)

90.5

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

11.03

Slightly mobile

K_foc

735

¹/_n

0.93

Notes and range

EU dossier kf range 1.0-35.5 ml/g, K_foc range 457-1340 mL g⁻¹, ¹/_n range 0.71-1.16, Soils=10

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.29

Calculated

Transition state

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

Value

1.23 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

alpha,alpha,alpha-trifluoro-3’-hydroxy-o-toluanilide

flutolanil metabolite M4

Rat (Urinary, Faeces); Plant

alpha,alpha,alpha-trifluoro-4’-hydroxy-3’-isopropoxy-o-toluanilide

flutolanil metabolite M2

Rat (Urinary, Faeces); Plant

alpha,alpha,alpha-trifluoro-4’-hydroxy-3’-methoxy-o-toluanilide

flutolanil metabolite M7

Rat (Urinary)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

100

Whole fish

Threshold for concern

CT₅₀ (days)

0.5

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 10000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

> 1614

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

1249 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

247.8

Colinius virginianus NOEC

Low

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

5.4

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.233

Pimephales promelas

Moderate

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

> 6.8

Daphnia magna

Moderate

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

0.29

Daphnia magna

Moderate

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

0.13

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)

Lemna gibba

Moderate

Non-target plants

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

> 3.2

Pseudokirchneriella subcapitata

Moderate

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

0.18

Selenastrum capricornutum

Moderate

Honeybees (Apis spp.)

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

> 200

Apis mellifera

Low

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

> 208.7

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)

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)

12.9

Eisenia foetida 56 days

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

18.8

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

2.5 / 3

Mortality / Reproduction [Dose: 4.5 kg ha⁻¹]
Aphidius rhopalosiphi adult female

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

1.1 / 5

Mortality / Reproduction [Dose: 4.5 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 1.35 kg ha⁻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)

> 10000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.98

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.09

SF=100

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

0.4

Rabbit SF=100

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

0.28

Rabbit SF=100

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

0.26

Rat 90 day SF=100

Dermal penetration studies (%)

0.5-5.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Negligible risk to bystanders

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

May cause slight erythema in susceptible individuals
Possible thyroid, liver and spleen toxicant

Handling issues

Property

Value and interpretation

General

Prevent generation of mists or dust
Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H400, H410, H411

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

flutolanil

French

flutolanil

German

Flutolanil

Danish

flutolanil

Italian

flutolanil

Spanish

flutolanil

Greek

Polish

flutolanil

Swedish

Hungarian

Dutch

flutolanil

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