Flutriafol (Ref: PP 450)

Flutriafol (Ref: PP 450)	Last updated: 01/02/2021
(Not known by any other names)

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Slovakia/UK

Date EC 1107/2009 inclusion expires

31/05/2021

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, Brazil, South Africa, Russia, Tanzania

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 group

Triazole

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

CIPAC number

436

US EPA chemical code

128940

PubChem CID

91727

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

A marine pollutant

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 crystalline solid

Related substances & organisms

chlorothalonil

fludioxonil

1,2,4-triazole

(R)-flutriafol

(S)-flutriafol

Formulations

Property

Value

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

Beret Multi
Consul
Impact Excel
Pointer

Example products using this active

Headland
Syngenta

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)

Degradation point (°C)

270

Flashpoint (°C)

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

2.00 X 10⁰²

Calculated

Log P

2.3

Low

Bulk density (g ml⁻¹)

1.41

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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

3.96

Moderately mobile

K_foc

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

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

triazolyl alanine

Plant

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

TAA; triazolyl acetic acid

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

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

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

33.0

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.8

Pimephales promelas

Moderate

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

Daphnia magna

Moderate

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

0.55

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)

0.65

Lemna gibba

Moderate

Non-target plants

> 134

Unknown species
Seedling emergence, ER₅₀
as g ha⁻¹

> 134

Unknown species
Vegetative vigour, ER₅₀
as g ha⁻¹

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

Raphidocelis subcapitata

Low

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)

> 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)

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)

6.1

Eisenia foetida 56 days corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

204.5

Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

1125

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 1.67 kg kg⁻¹ soil 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)

> 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

UK ACP 1999

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

0.05

Dog 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

Dog SF=100

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

Notes

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

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 Code 9

CLP classification 2013

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

EC Risk Classification

Reproduction risk category 3: R63
Xn - Harmful: R20/21/22
N - Dangerous for the environment: R52, R53

EC Safety Classification

S22, S24, S25

WHO Classification

II (Moderately hazardous)

UN Number

3077

Waste disposal & packaging

Packaging Group III (Minor danger)

TRANSLATIONS

Language

Name

English

flutriafol

French

flutriafol

German

Flutriafol

Danish

flutriafol

Italian

flutriafol

Spanish

flutriafol

Greek

Polish

flutriafol

Swedish

Hungarian

flutriafol

Dutch

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