fluopicolide (Ref: AE C638206) ** Translations

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GENERAL INFORMATION
for fluopicolide

Description: A fungicide used for the control of a range of Oomycete diseases including downy mildew and blight

Example pests controlled: Various Oomycete diseases including downy mildews (Plasmopara, Pseudoperonospara, Peronospora, Bremia), late blight (Phytophthora), and some Pythium species.

Example applications: Grapes; Hops; Potatoes; Various vegetables including onions, roots and tubers

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 2006

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

Status	Approved
Dossier rapporteur/co-rapporteur	UK/Spain
Date inclusion expires	31/05/2023
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

Chemical structure:

Isomerism	-
Chemical formula	C14H8Cl3F3N2O
Canonical SMILES	C1=CC(=C(C(=C1)Cl)C(=O)NCC2=C(C=C(C=N2)C(F)(F)F)Cl)Cl
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	GBOYJIHYACSLGN-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C14H8Cl3F3N2O/c15-8-2-1-3-9(16)12(8)13(23)22-6-11-10(17)4-7(5-21-11)14(18,19)20/h1-5H,6H2,(H,22,23)/f/h22H
2D structure diagram/image available?	Yes

General status:

Pesticide type	Fungicide
Substance group	Benzamide
Minimum active substance purity	970 g/kg
Known relevant impurities	EU dossier - toluene max 0.3%
Substance origin	Synthetic
Mode of action	Protectant, novel mode of action as fluopicolide delocalises spectrin-like proteins
CAS RN	239110-15-7
EC number	-
CIPAC number	787
US EPA chemical code	027412
PubChem CID	11159021
Molecular mass (g mol-1)	383.58
PIN (Preferred Identification Name)	-
IUPAC name	2,6-dichloro-N-[3-chloro-5-(trifluoromethyl)-2-pyridylmethyl]benzamide
CAS name	2,6-dichloro-N-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)methyl)benzamide
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)	43
Examples of recorded resistance	-
Physical state	Beige coloured solid
Related substances & organisms	propamocarb hydrochloride

Formulations:

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Bayer CropScience
Example products using this active	Infinito
UK LERAP status	None
Formulation and application details	Available as dispersible granules that are mixed with water and used as a spray.

ENVIRONMENTAL FATE
for fluopicolide

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		2.8	A5	Low
Solubility - In organic solvents at 20oC (mg l-1)		200	A5 - n-Hexane	-
		19200	A5 - Ethanol	-
		20500	A5 - Toluene	-
		74700	A5 - Acetone	-
Melting point (oC)		150	A5	-
Boiling point (oC)		Decomposes before boiling	A5	-
Degradation point (oC)		320	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	7.94 X 1002	Calculated	-
	Log P	2.9	A5	Moderate
Bulk density (g ml-1)/Specific gravity		1.65	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		3.03 X 10-04	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		4.15 X 10-05	A5	Non-volatile
GUS leaching potential index		3.63	Calculated	High leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate	Value	8.10 X 10-01	Calculated	-
	Note	-
Potential for particle bound transport index		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		Neutral solution 203nm = 44519, 271nm = 3601	A5	-
Surface tension (mN m-1)		71.3	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	271	A5	Persistent
	DT50 (lab at 20oC)	271	A5	Persistent
	DT50 (field)	138.8	A5	Persistent
	DT90 (lab at 20oC)	900	A5	-
	DT90 (field)	720	A5	-
	DT50 modelling endpoint	-	-	-
	Note	EU dossier Lab studies DT50 range 194-333 days, DT90 range 644-2216 days; Field studies DT50 range 50-172 days, DT90 range 863-1184 days
Dissipation rate RL50 on plant matrix	Value	4.3	R3	-
	Note	Cabbage leaves, n=1
Dissipation rate RL50 on and in plant matrix	Value	7.4	R4	-
	Note	Published literature RL50 range 3.6-11.3 days, 2 field crops, various matrices, n=2
Aqueous photolysis DT50 (days) at pH 7	Value	64	A4	Stable
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Not pH sensitive
Water-sediment DT50 (days)		1117	A5	Stable
Water phase only DT50 (days)		91.4	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	4.20	A5	Moderately mobile
	Kfoc	321.1
	1/n	0.90
	Notes and range	EU dossier Kf range 1.42-9.27, Kfoc range 172-580 mL/g, 1/n range 0.86-0.93, Soils=8
pH sensitivity		No

Key metabolites:

Metabolite		Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
4-N-[3-chloro-5-trifluoromethyl-pyridin-2-yl-(hydroxyl)methyl]-2,6-dichlorobenzamide (Ref: AE-0608000)		Soil	0.106	Major fraction, Relevant
2,6-dichlorobenzamide (Ref: AE C653711)		Soil	0.250	Major fraction, Relevant
3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid (Ref: AE-C657188)		Soil	0.073	Major fraction, Relevant

Other known metabolites:

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
2,6-dichloro-N-[(3-chloro-5-trifluoromethylpyridin-2-yl)methyl]-4-hydroxy benzamide (Ref: AE 0712556)	-	Animal	-	-
3-methylsulfinyl-5-trifluoro-methylpyridine-2-carboxylic acid (Ref: AE 1344122)	-	Plant; Soil; Groundwater	-	-
3-sulfo-5-trifluoromethylpyridine-2-carboxylic acid (Ref: AE 1344123)	-	Groundwater; Soil	-	-
3-mesyl-5-(trifluoromethyl)pyridin-2-ol (Ref: AE 1388273)	-	Soil; Groundwater	-	-
3,5-dichloro-4-[3-chloro-5-trifluoromethylpyridine-2-yl-methyl) carbamoyl] benzenesulfonic acid (Ref: AE 1413903)	-	Soil; Groundwater	-	-
3-chloro-2-hydroxy-5-trifluoromethylpyridine (Ref: AE B102859)	-	Plant	-	-
2,6-dichloro-N-((3-chloro-5-trifluoromethylpyridine-2-yl)methyl)-3-hydroxybenzamide (Ref: AE C643890)	-	Plant; Animal	-	-
3-chloro-5-trifluoromethylpyridine-2-carboxamide (Ref: AE C653598)	-	Plant; Groundwater	-	-
2,6-dichloro-3-hydroxybenzamide (Ref: AE C657378)	-	Plant; Rat	-	-

ECOTOXICOLOGY
for fluopicolide

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	121	A5	Threshold for concern
	CT50 (days)	0.51		-
Mammals - Acute oral LD50 (mg kg-1)		> 5000	A5 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	10	A3 Rabbit	High
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		> 2250	A5 Colinus virginianus	Low
Birds - Short term dietary (LC50/LD50)		> 1744 mg kg bw-1 day-1	A5 Colinus virginianus	-
Fish - Acute 96 hour LC50 (mg l-1)		0.36	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		0.155	A4 Pimephales promelas, 35 day	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		> 1.8	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		0.37	A5 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)		49.0	A5 Chironomus riparius	Low
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1)		-	-	-
Aquatic plants - Acute 7 day EC50, biomass (mg l-1)		> 3.2	A5 Lemna gibba	Moderate
Non-target plants		> 3000	A5 Lettuce, Cucumber Seedling emergence, ER50 as g/ha	-
		> 3000	A5 OSR Vegetative vigour, ER50 as G/ha	-
Algae - Acute 72 hour EC50, growth (mg l-1)		0.029	A5 Navicula pelliculosa, Biomass	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)	> 241	A5	Low
	Unknown mode acute 48 hour LD50 (μg bee-1)	-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		> 500	A5 Eisenia foetida, corr	Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50 / EC50 / NOEC / % Effect	31.25	A5 Folsomia candida, 28 day NOEC	-
Other arthropod (1)	LR50 g ha-1	8230	48 hour A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	7130	7 day A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 1.84 mg kg-1 soil, 28 days	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for fluopicolide

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)		> 5000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 5.16	A5 Rat, 4 hr (nose only)	-
Other Mammal toxicity endpoints		-		-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.08	A3 proposed, Mouse, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.18	A3 proposed Rat, SF=100	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.05	A3 proposed Rat, 90 day, SF=100	-
Dermal penetration studies (%)		0.24-2.75	A5 concentration dependent	-
Dangerous Substances Directive 76/464		List II	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	No unacceptable risks for bystanders identified
	Occupational	Potential risk to operators if PPE/PPC not utilised
European MRLs		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		0.1	EU Dir 89/778/EC limit; Calc MAC=0.24 μg l-1; A5	-

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		Possible liver, kidney and spleen 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 flammable, explosive or oxidising
CLP classification 2013		Environment: H400
EC Risk Classification		N - Dangerous for the environment: R50, 53
EC Safety Classification		S35, S57
WHO Classification		NL	-	Not listed
US EPA Classification (formulation)		No consensus across products or no products available	-	-
UN Number		Usually 3077
Waste disposal & packaging		-

TRANSLATIONS
for fluopicolide

Language	Name
English	fluopicolide
French	fluopicolide
German	Fluopicolid
Danish	fluopicolid
Italian	fluopicolide
Spanish	fluopicolida
Greek	-
Slovenian	flupokolid
Polish	fluopikolid
Swedish	fluopikolid
Hungarian	-
Dutch	fluopicolide

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Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk