Fludioxonil (Ref: CGA 173506)

Fludioxonil (Ref: CGA 173506)	Last updated: 24/10/2024
(Also known as: fludioxonyl)

SUMMARY

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 Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Daphnia chronic ecotoxicity: High	Human health Moderate alert: Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A broad-spectrum fungicide for control of a range of diseases on fruit and vegetables

Example pests controlled

Seedling blight, Stem-Base Browning, Snow Mould, Common Bunt, Black spot, Grey mould, Storage rot

Example applications

Fruit including apples, soft fruit, cranberries, pear, quince, strawberry and currants; Vegetables including peas, beans; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1990, first reported; 1993, first sales France

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/10/2028

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

France/Spain

Date EC 1107/2009 inclusion expires

15/06/2025

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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, USA, Iran, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₆F₂N₂O₂

Canonical SMILES

C1=CC(=C2C(=C1)OC(O2)(F)F)C3=CNC=C3C#N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

MUJOIMFVNIBMKC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H6F2N2O2/c13-12(14)17-10-3-1-2-8(11(10)18-12)9-6-16-5-7(9)4-15/h1-3,5-6,16H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fludioxonil	-

General status

Pesticide type

Fungicide, Other substance

Other bioactivity & uses

Biocide, Preservative

Substance groups

Phenylpyrrole fungicide; Pyrrole fungicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Non-systemic with long residual activity. Inhibits transport-associated phosphorylation of glucose, reducing mycelial growth. Osmotic signal transduction.

CAS RN

131341-86-1

EC number

603-476-3

CIPAC number

522

US EPA chemical code

071503

PubChem CID

86398

CLP index number

608-069-00-4

Molecular mass

248.19

PIN (Preferred Identification Name)

4-(2,2-difluoro-2H-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile

IUPAC name

4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile

CAS name

4-(2,2-difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile

Other status information

Some applications may be approved under the GB Biocide Products Regulation

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

Yellow crystals

Formulations

Property

Value

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

Syngenta

Example products using this active

Austral Plus
Beret Gold
Beret Multi
Switch
Wakil XL
Celest 025FS

Formulation and application details

Often supplied as a flowable concentrate that is mixed with water and used as a seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1.8

Low

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

20000

Octanol

190000

Acetone

2700

Toluene

42000

Methanol

Melting point (°C)

199.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

306

Flashpoint (°C)

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

1.32 X 10⁰⁴

Calculated

Log P

4.12

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.54

Dissociation constant pKa) at 25 °C

pKa(1) base; pKa(2) 14.1 acid

Vapour pressure at 20 °C (mPa)

3.90 X 10^-04

Low volatility

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

5.40 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 266nm = 12384
ACidic solution: 265nm = 12327
Basic solution: 271nm = 11790

Surface tension (mN m⁻¹)

47.7-48.5

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

164

Persistent

DT₅₀ (lab at 20 °C)

218.6

Persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range: 119-365 days, field study DT₅₀ range 8-43 days; General literature lab studies DT₅₀ range 100-350 days; field studies DT₅₀ range 10-25 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

9.7

Note

Published literature RL₅₀ range 1.8-15.4 days, 4 field & undercover grown crops, various matrices, n=8; Grapes in cold storage RL₅₀=24 days

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

12.1

Note

Published literature RL₅₀ range 2.1-50.2 days, 4 field & undercover grown crops, various matrices, n=7

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

575

Stable

Water phase only DT₅₀ (days)

Moderately fast

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

[Lettuce: 5.8 days @ 4 DegC, dark; Field study], [Lettuce: ~8 days @ 4 degC], [Peppers: ~8 days @ 4 DegC], [Table grapes: 18.1 days @ 4 DegC, dark; Field study], [White grape juice: 33 days @ 40 DegC; Lab study], [Waxed apples: No observed residue decay after 40 days @ 18-25 DegC, shady conditions; Field study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

145600

Notes and range

Industry data

Freundlich

K_f (mL g⁻¹)

3312

Non-mobile

K_foc (mL g⁻¹)

132100

¹/_n

1.00

Notes and range

EU dossier K_f range 290-7300, K_foc range 7500-210000 mL g⁻¹, ¹/_n range 0.81-1.19, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.35

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

3.6

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

366

Whole fish

Threshold for concern

CT₅₀ (days)

0.6

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

Ref: SYN545245

Major fraction

0.294

Syngenta verified

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-carbamoyl-2-cyano-3-(2,2-difluoro-benzo(1,3)dioxol-4-yl)-oxirane-2-carbocyclic acid (Ref: CGA 339833)

Not relevant

0.37

2220

(2,2-difluoro-benzo(1,3)dioxol-4-carbocyclic acid (Ref: CGA 192155)

Not relevant

0.29

1740

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-hydroxy-acetamide (Ref: CGA 308103)

Rat

2-cyano-3-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)propanoic acid or 3-cyano-2-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)propanoic acid

fludioxonil metabolite A5

Water (Photolysis)

2-cyano-3-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-succinamic acid (Ref: CGA 344623)

Water (Photolysis)

4-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-5-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (Ref: CGA 308565)

Rat

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

58.5

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

212

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 833 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

11.1

Unknown species NOEC

Moderate

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

>= 1000

Eisenia foetida

Moderate

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

>= 20

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 0.333 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

14.4

Folsomia candida

Non-target plants

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)

> 100

Apis mellifera

Low

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 at dose 0.112 kg ha⁻¹

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as % Mortality at dose 2 kg ha⁻¹

2.0

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)

0.23

Oncorhynchus mykiss

Moderate

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

0.04

Oncorhynchus mykiss

Moderate

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

0.46

Danio rerio EC₅₀ Embryo

Moderate

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

0.4

Daphnia magna

Moderate

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

0.005

Daphnia magna

High

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

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

0.27

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)

0.2

Chironomus riparius Emergence

Moderate

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

40.0

Chironomus riparius Emergence

Moderate

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

0.92

Lemna gibba

Moderate

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

0.024

Scenedesmus subspicatus

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

0.0164

Aquatic invertebrates based on product with cyprodinil

NOEAEC mg l⁻¹

Marine bivalves

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.6

Rat (nose only)

Other Mammal toxicity endpoints

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

0.37

Rat SF=100

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

None allocated

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

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

0.59

Dog SF=100

Dermal penetration studies (%)

0.3-1.7

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Negligible risk to bystanders

Occupational

No unacceptable risk to operators and other workers identified

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL modified for various commodities Julty 2023 - see UK HSE website

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

; ; ; ;

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

Liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H311, H319
Environment: H400, H410, H412

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Stable and non-reactive under normal conditions of use, storage and transport.

TRANSLATIONS

Language

Name

English

fludioxonil

French

fludioxonyl

German

Fludioxonil

Danish

fludioxonil

Italian

fludioxonil

Spanish

fludioxonil

Greek

Polish

fludioksonil

Swedish

fludioxonil

Hungarian

fludioxonil

Dutch

Norwegian

fludioksonil

Record last updated:	24/10/2024
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