fludioxonil (Ref: CGA 173506) ** fludioxonyl ** Translations

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GENERAL INFORMATION
for fludioxonil

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, Blacl 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

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	France/Spain
Date inclusion expires	31/10/2019
EU Candidate for substitution (CfS)	Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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
Structure diagram/image available?	Yes

General status:

Pesticide type	Fungicide
Substance group	Phenylpyrrole
Minimum active substance purity	950 g/kg
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 (g mol-1)	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)	12
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	Syngenta
Example products using this active	Austral Plus Beret Gold Beret Multi Switch Wakil XL Celest 025FS
UK LERAP status	None
Formulation and application details	Often supplied as a flowable concentrate that is mixed with water and used as a seed treatment.

ENVIRONMENTAL FATE
for fludioxonil

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		1.8	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		20000	A5 - Octanol	-
		190000	A5 - Acetone	-
		2700	A5 - Toluene	-
		42000	A5 - Methanol	-
Melting point (oC)		199.8	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		306	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	1.32 X 1004	Calculated	-
	Log P	4.12	A5	High
Bulk density (g ml-1)/Specific gravity		1.54	B5	-
Dissociation constant (pKa) at 25oC		0	A5 -	-
		Note: pKa(1) base; pKa(2) 14.1 acid
Vapour pressure at 20oC (mPa)		3.90 X 10-04	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		5.40 X 10-05	L3	Non-volatile
GUS leaching potential index		-2.67	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		-	Calculated	High
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution: 266nm = 12384; [ACidic solution: 265nm = 12327; [Basic solution: 271nm = 11790	A5	-
Surface tension (mN m-1)		47.7-48.5	A5	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	164	E4	Persistent
	DT50 (lab at 20oC)	239	A5	Persistent
	DT50 (field)	20.5	A5	Non-persistent
	DT90 (lab at 20oC)	-	-	-
	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	R4	-
	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	R4	-
	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	10	A5	Moderately fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 9
Water-sediment DT50 (days)		575	A5	Stable
Water phase only DT50 (days)		2	A5	Moderately fast

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	E4	Non-mobile
	Koc	145600
	Notes and range	Industry data
Freundlich	Kf	3312	A5	Non-mobile
	Kfoc	132100
	1/n	1.00
	Notes and range	EU dossier Kf range 290-7300, Kfoc range 7500-210000 mL/g, 1/n range 0.81-1.19, Soils=5
pH sensitivity		No

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-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	-
2-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-2-hydroxy-acetamide (Ref: CGA 308103)	-	Rat	-	-
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-cyano-3-(2,2-difluoro-benzo[1,3]dioxol-4-yl)-succinamic acid (Ref: CGA 344623)	-	Water (Photolysis)	-	-

ECOTOXICOLOGY
for fludioxonil

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	366	A5 Whole fish	Threshold for concern
	CT50 (days)	0.6		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	10	E4 Rat	High
	(ppm diet)	58.5		-
Birds - Acute LD50 (mg kg-1)		> 2000	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 833 mg kg bw-1 day-1	A4 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.23	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.04	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		0.4	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.005	A5 Daphnia magna	High
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.27	A5 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	A5 Chironomus riparius, emergence	Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		40.0	A5 Chironomus riparius, emergence	Moderate
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		0.92	A5 Lemna gibba	Moderate
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.024	A5 Scenedesmus subspicatus	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		-	-	-
Honeybees	Contact acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Oral acute 48 hour LD50 (μg bee-1)	> 100	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		>= 1000	A5 Eisenia foetida	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		20	A5 Eisenia foetida	Moderate
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	14	Mortality Dose: 0.112 kg ha-1 A5 Aphidius rhopalosiphi	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	2	Mortality Dose: 1 kg ha-1 A5 Typhlodromus pyri	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 0.333 mg kg-1 soil	-
Mesocosm study data	NOEAEC mg l-1	0.0164	A3 Aquatic invertebrates, based on product with cyprodinil	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for fludioxonil

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Dermal LD50 (mg kg-1 body weight)		> 2000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 2.6	A5 Rat (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.37	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		None allocated	A5	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.59	A5 Dog, SF=100	-
Dermal penetration studies (%)		0.3-1.7	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	Negligible risk to bystanders
	Occupational	No unacceptable risk to operators and other workers identified
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	-	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		Liver and kidney toxicant

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		Not explosive or oxidising IMDG Transport Code is usually 9
CLP classification 2013		Environment: H400, H410
EC Risk Classification		N - Dangerous for the environment: R50/53
EC Safety Classification		S60, S61
WHO Classification		U	-	Unlikely to present an acute hazard
US EPA Classification (formulation)		III	-	Caution - Slightly toxic
UN Number		Usually 3082
Waste disposal & packaging		Packaging Group III (minor danger)

TRANSLATIONS
for fludioxonil

Language	Name
English	fludioxonil
French	fludioxonyl
German	Fludioxonil
Danish	fludioxonil
Italian	fludioxonil
Spanish	fludioxonil
Greek	-
Slovenian	fludioksonil
Polish	fludioksonil
Swedish	fludioxonil
Hungarian	fludioxonil
Dutch	-

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Record last updated: Monday 05 November 2018
Contact: aeru@herts.ac.uk