Fludioxonil (Ref: CGA 173506)

Fludioxonil (Ref: CGA 173506)	Last updated: 27/01/2021
(Also known as: fludioxonyl)

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/10/2024

UK LERAP status

None

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

31/10/2021

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
✓	✓	✓	✓	✓	✓	✓	✓	✓

Also used in

Australia, USA

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

Substance group

Phenylpyrrole

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

CIPAC number

522

US EPA chemical code

071503

PubChem CID

86398

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

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

Yellow crystals

Related substances & organisms

cymoxanil

metalaxyl-M

cyprodinil

flutriafol

tefluthrin

Formulations

Property

Value

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

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

Example products using this active

Syngenta

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)

Not expected to self ignite; Not highly flammable

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

1.32 X 10⁰⁴

Calculated

Log P

4.12

High

Bulk 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

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 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 on and in plant matrix

Value

4.2

Note

Published literature RL₅₀ range 2.1-9.3 days, 3 field & undercover grown crops, various matrices, n=4; Lettuce/peppers in cold storage RL₅₀ range 7.7-9.3 days

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

145600

Notes and range

Industry data

Freundlich

K_f

3312

Non-mobile

K_foc

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

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.188

Major fraction, Not relevant

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

Soil

0.197

Major fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

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

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)

4-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (Ref: CGA 265378)
Note: Highly mobile

Soil (Photolysis)

0.123

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

366

Whole fish

Threshold for concern

CT₅₀ (days)

0.6

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.23

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.04

Oncorhynchus mykiss

Moderate

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

0.4

Daphnia magna

Moderate

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

0.005

Daphnia magna

High

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

Non-target plants

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

0.024

Scenedesmus subspicatus

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)

> 100

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)

>= 1000

Eisenia foetida

Moderate

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

>= 20

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

14.4

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 0.112 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 1 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 0.333 mg kg⁻¹ soil

Mesocosm study data

NOEAEC mg l⁻¹

0.0164

Aquatic invertebrates based on product with cyprodinil

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)

> 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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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 Code is usually 9

CLP classification 2013

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

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

S60, S61

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

fludioxonil

French

fludioxonyl

German

Fludioxonil

Danish

fludioxonil

Italian

fludioxonil

Spanish

fludioxonil

Greek

Polish

fludioksonil

Swedish

fludioxonil

Hungarian

fludioxonil

Dutch

Record last updated:	27/01/2021
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