Flutriafol (Ref: PP 450)

Flutriafol (Ref: PP 450)	Last updated: 31/10/2024
(Not known by any other names)

SUMMARY

Flutriafol is a commonly used curative and preventative fungicide. It is moderately soluble in water, tends to be persistent in soil systems and is often stable in aquatic systems. It is moderately mobile and so may leach to groundwaters under certain conditions. It is moderately toxic to most biodiversity including honeybees and earthworms. It may be a development and/or reproduction toxin.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Very persistent; GUS: High leachability	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

A curative and preventative conazole fungicide used to control leaf and ear diseases usually in cereals

Example pests controlled

Leaf and ear diseases

Example applications

Cereals including corn; Soybeans; Apples

Efficacy & activity

Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Low; Soybean/Anthracnose=High; Soybean/Brown spot=High; Soybean/Leaf blight=Moderate; Soybean/Rust=High; Soybean/White mould=Moderate

Availability status

Current

Introduction & key dates

1981, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Slovakia/Czech Republic

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Australia, Brazil, South Africa, Russia, Tanzania, Morocco

Chemical structure

Isomerism

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

Chemical formula

C₁₆H₁₃F₂N₃O

Canonical SMILES

C1=CC=C(C(=C1)C(CN2C=NC=N2)(C3=CC=C(C=C3)F)O)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

JWUCHKBSVLQQCO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H13F2N3O/c17-13-7-5-12(6-8-13)16(22,9-21-11-19-10-20-21)14-3-1-2-4-15(14)18/h1-8,10-11,22H,9H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Triazole fungicide; Conazole fungicide

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier - dimethyl sulphate: <0.01%; dimethylformamide:<0.1%; methanol: <0.1%

Substance origin

Synthetic

Mode of action

Broad-spectrum, systemic, contact action with eradicant and protective properties. Sterol biosynthesis inhibitor.

CAS RN

76674-21-0

EC number

616-367-0

CIPAC number

436

US EPA chemical code

128940

PubChem CID

91727

CLP index number

No data found

Molecular mass

301.29

PIN (Preferred Identification Name)

IUPAC name

(RS)-2,4'-difluoro-α-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol

CAS name

α-(2-fluorophenyl)-α-(4-fluorophenyl)-1H-1,2,4-triazole-1-ethanol

Other status information

Marine pollutant

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White to off-white crystalline solid

Related substances & organisms

(R)-flutriafol

(S)-flutriafol

Formulations

Property

Value

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

Headland
Syngenta
BOC Sciences
Axichem Pty Ltd

Example products using this active

Beret Multi
Consul
Impact Excel
Pointer
AC Fearsome 500

Formulation and application details

Often supplied as a soluble concentrate that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

95.0

Moderate

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

116000

Acetone

300

Hexane

115000

Methanol

10000

Xylene

Melting point (°C)

130

Boiling point (°C)

506.5

Degradation point (°C)

270

Flashpoint (°C)

260.1

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

2.00 X 10⁰²

Calculated

Log P

2.3

Low

Fat solubility of residues

Solubility

Likely to be soluble

Data type

Based on chemical group

Density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

2.3

Strong acid

Vapour pressure at 20 °C (mPa)

4.0 X 10^-04

Low volatility

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

1.27 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

No absorption above 290nm

Surface tension (mN m⁻¹)

68.7

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1358

Very persistent

DT₅₀ (lab at 20 °C)

1587

Very persistent

DT₅₀ (field)

1177.3

Very persistent

DT₉₀ (lab at 20 °C)

5272.8

Very persistent

DT₉₀ (field)

3911.1

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 672-3492 days, DT₉₀ range 2231-11599 days; Other Lab studies - degradation very slow, field study DT₅₀ range 316-4089 days, DT₉₀ range 1051-13583 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

11.7

Note

Wheat, whole plant, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Water-sediment DT₅₀ (days)

Stable

Water phase only DT₅₀ (days)

Stable

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

3.96

Moderately mobile

K_foc (mL g⁻¹)

205

¹/_n

0.906

Notes and range

EU dossier K_f range 1.3-9.75 mL g⁻¹, K_foc range 104-395 mL g⁻¹, ¹/_n range 0.88-0.97

pH sensitivity

Slowly decreasing sorption with increasing pH - not significant

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

5.18

Calculated

High leachability

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

Value

7.09 X 10⁰⁰

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

1.1

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Likely to be soluble

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

triazolyl alanine

Plant

1H-1,2,4-triazol-1-ylacetic acid (Ref: CGA 142856)

TAA; triazolyl acetic acid

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 1140

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

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

13.5

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

616

Alectoris rufa

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

435 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

35.8

Colinus virginianus NOEC

Moderate

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

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

6.1

Eisenia foetida 56 day corr

Moderate

Soil micro-organisms

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

Dose: 1.67 kg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 134

Unknown species
Seedling emergence, ER₅₀
as g ha⁻¹

> 134

Unknown species
Vegetative vigour, ER₅₀
as g ha⁻¹

Honeybees (Apis spp.)

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

> 50

Apis mellifera

Moderate

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

> 2.0

Apis mellifera

Moderate

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

Chronic

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 1125

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

204.5

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

33.0

Lepomis macrochirus

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

4.8

Pimephales promelas

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 51.2

Danio rerio Embryo

Moderate

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

Daphnia magna

Moderate

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

0.55

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

1.6

Chironomus riparius 26 day

Moderate

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

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

0.65

Lemna gibba

Moderate

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

Raphidocelis subcapitata

Low

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 1140

Rat

Moderate

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

1000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.2

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.01

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

0.05

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

Dermal penetration studies (%)

0.3-10.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable risk for proposed uses

Occupational

Acceptable risk for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

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 liver toxicant
May cause anaemia
Endocrine issues - Weak estrogen inhibition

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
Not explosive or oxidising
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H302, H312, H332, H361
Environment: H411, H412

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Limited shelf-life. Store at -20 DegC

TRANSLATIONS

Language

Name

English

flutriafol

French

flutriafol

German

Flutriafol

Danish

flutriafol

Italian

flutriafol

Spanish

flutriafol

Greek

Polish

flutriafol

Swedish

Hungarian

flutriafol

Dutch

Norwegian

Record last updated:	31/10/2024
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