Flutianil (Ref: OK-5303)

Flutianil (Ref: OK-5303)	Last updated: 12/01/2021
(Not known by any other names)

SUMMARY

Flutianil is a horticultural fungicide that has EU approval for use. It has a very low solubility and is volatile. It is persistent in soils. It has a low mammalian toxicity but there are some concerns regarding effects on reproduction and carginogenicity. It exhibits moderate to low toxicity to most aquatic and terrestrial organisms.

GENERAL INFORMATION

Description

A fungicide with contact action used for a range of horticultural crops

Example pests controlled

Uncinula necator, Golovinomyces spp.

Example applications

Grapevines; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

2008

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

United Kingdom

Date EC 1107/2009 inclusion expires

14/04/2029

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

Isomeric

Chemical formula

C₁₉H₁₄F₄N₂OS₂

Canonical SMILES

COC1=CC=CC=C1N2CCSC2=C(C#N)SC3=C(C=CC(=C3)C(F)(F)F)F

Isomeric SMILES

COC1=CC=CC=C1N\2CCS/C2=C(/C#N)\SC3=C(C=CC(=C3)C(F)(F)F)F

International Chemical Identifier key (InChIKey)

KGXUEPOHGFWQKF-ZCXUNETKSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H14F4N2OS2/c1-26-15-5-3-2-4-14(15)25-8-9-27-18(25)17(11-24)28-16-10-12(19(21,22)23)6-7-13(16)20/h2-7,10H,8-9H2,1H3/b18-17-

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Thiazolidine

Minimum active substance purity

985 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Mode of action

Contact action - both fungitoxic and fungistatic

CAS RN

958647-10-4

EC number

CIPAC number

835

US EPA chemical code

PubChem CID

44151818

Molecular mass

426.45

PIN (Preferred Identification Name)

(2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]sulfanyl}[3-(2-methoxyphenyl)-1,3-thiazolidin-2-ylidene]acetonitrile

IUPAC name

(Z)-(3-(2-methoxyphenyl)-1,3-thiazolidin-2-ylidene)(a,a,a,4-tetrafluoro-m-tolylthio)acetonitrile

CAS name

(2Z)-2-((2-fluoro-5-(trifluoromethyl)phenyl)thio)-2-(3-(2-methoxyphenyl)-2-thiazolidinylidene)acetonitrile

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)

U13

Examples of recorded resistance

Physical state

White crystalline powder

Formulations

Property

Value

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

Pinpoint
Gatten
Flutianil 5% EC

Example products using this active

Otsuka Chemical Co

Formulation and application details

Usually supplied as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.1

Low

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

11200

Toluene

169000

Dichloromethane

66400

Acetone

56200

Methanol

Melting point (°C)

178

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

242

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.26 X 10⁰³

Calculated

Log P

3.1

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.53 X 10^-04

Low volatility

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

8.26 X 10^-03

Non-volatile

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

Neutral: 282nm=17500, 244.5nm=16900
Acidic: 283nm=17100, 245nm=16300
Basic: 282nm=17600, 245nm=16700

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

286

Persistent

DT₅₀ (lab at 20 °C)

297.3

Persistent

DT₅₀ (field)

14.4

Non-persistent

DT₉₀ (lab at 20 °C)

1162

Very persistent

DT₉₀ (field)

48.0

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 262.6-338.4 days, DT₉₀ range 1031-1256 days, Field studies DT₅₀ range 1.2-159 days, DT₉₀ range 4.1-529 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

1.1

Moderately fast

Note

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

Value

Stable

Note

Stable at all environmentally relevant pHs

Water-sediment DT₅₀ (days)

607

Stable

Water phase only DT₅₀ (days)

1.0

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

794

Non-mobile

K_foc

35492

¹/_n

0.99

Notes and range

EU dossier K_f range 533-1093 mL g⁻¹, K_foc range 20631-79448 mL g⁻¹, ¹/_n range 0.96-1.10, soils=5

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.64

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(Z)-2-(2-fluoro-5-(trifluoromethyl)phenylsulfinyl)-2-(3,2-methoxyphenyl)thiazolidin-2-ylidene)acetonitrile (Ref: OC 53276)

Soil

0.086

Minor fraction, Relevant

(Z)-2-(2-fluoro-5-(trifluoromethyl)phenylsulfinyl)-2-(3,2-methoxyphenyl) 1-oxo-thiazolidin-2-ylidene)acetonitrile (Ref: OC 56574)

Soil

0.189

Major fraction, Relevant

(Z)-2-(2-fluoro-5-(trifluoromethyl)phenylthio)-2-(4-hydroxy-3-(2-methoxyphenyl)thiazolin-2-ylidene)acetonitrile (Ref: OC 53279)

Soil

0.003

Minor fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(Z)-2-(2-fluoro-5-(methyl)phenylthio)-2-(3-(2-methoxyphenyl) 2-thiazolidinylidene] acetonitrile

OC 53982

Rat

(2-cysteinyl-3-hydroxy-5-trifluoromethyl) S-acetylthiophenol -1,1 dioxide

Rat

2-fluoro-3-cysteinyl-4-hydroxy-5-trifluoromethyl benzene sulponic acid

Rat

2-S-acetylthiophenol -1,1 dioxo-4-trifluoromethyl-6-hydroxy phenylthio(methyl-2-(1,4 piperazine-3,6-dione)

Rat

methyl 2-fluoro-3-cysteinylmethyl benzene sulphonic acid

Rat

2-cysteinylglutamyl-3-fluoro-4-sulphonic acid-6-trifluoromethyl phenyl acetate

Rat

92-S(N-acetyl)cysteinyl-5-trifluoromethyl) S-acetylthiophenol -1,1 dioxide

Rat

2-acetamido-3-(-2-hydroxy-3-(methylsulfinyl)-5-)trifluoromethyl)phenylthio)propanoic acid

Rat

(Z)-2-(2-fluoro-5-(trifluoromethyl)phenylsulfonyl)-2-(3,2-methoxyphenyl)thiazolidin-2-ylidene)acetonitrile

OC 53277

Plant

(Z)-2-(2-fluoro-5-(trifluoromethyl)phenylthio)-2-(3,2-hydroxyphenyl)thiazolidin-2-ylidene)acetonitrile

OC 42121

Plant

2-fluoro-5-(trifluoromethyl)benzenesulfonic acid

OC 56635

Plant; Soil; Water; Rat

1,2-bis(2-fluoro-5-(trifluoromethyl)phenyl)disulfane

OC 56634

Plant

2-methoxybenzenamine

OC 56631

Plant; Rat

(Z)-2-(2-fluoro-5-(methyl)phenylsulfinyl)-2-(3-(2-methoxyphenyl) thiazolidin-2-ylidene] acetonitrile

OC 53429

Rat

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

339

Threshold for concern

CT₅₀ (days)

1.97

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg diet⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.870

Cyprinua carpio

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000781

Pimephales promelas

High

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

> 1.0

Daphnia magna

Moderate

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

0.007

Daphnia magna

High

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)

396

Chironomus riparius

Low

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

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

Non-target plants

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

> 0.085

Pseudokirchneriella 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)

> 100

Apis mellifera

Low

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

> 200

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)

6.25

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

6.0

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

31.7

48hr LR₅₀
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

583.74

7-day LR₅₀
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 0.75 mg kg⁻¹ 28 days

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.17

Rat 4 hr (nose only aerosol)

Other Mammal toxicity endpoints

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

0.82

Rat SF=100

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

1.0

Rabbit 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)

0.05

Rat SF=2000

Dermal penetration studies (%)

Default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk

Occupational

PPE/PPC advised to minimise exposure

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver & kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H410

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R22, R41, R43
Xi - Irritant: R38
N - Dangerous to the environment: R50/53

EC Safety Classification

S26, S36/37, S39, S60, S61

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

flutianil

French

German

Danish

Italian

Spanish

Greek

Polish

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