Fluopicolide (Ref: AE C638206)

Fluopicolide (Ref: AE C638206)	Last updated: 19/12/2024
(Not known by any other names)

SUMMARY

Fluopicolide is a fungicide used for the control of a range of Oomycete diseases including downy mildew and blight. It has a low aqueous solubility and is not highly volatile. It tends to be fairly persistent in most soil systems and stable in water-sediment systems. There is also a risk of it leaching to groundwater. No significant risks to human health have been identified. It is moderately toxic to most biodiversity but there is less of a risk to bees.

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 High alert: Persistent; GUS: High leachability	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Genotoxic

GENERAL INFORMATION

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, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2026

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Austria/Spain

Date EC 1107/2009 inclusion expires

31/08/2026

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

Morocco

Chemical structure

Isomerism

None

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

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fluopicolide	-

General status

Pesticide type

Fungicide

Substance groups

Benzamide fungicide; Pyridine fungicide

Minimum active substance purity

970 g kg⁻¹

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

607-285-6

CIPAC number

787

US EPA chemical code

027412

PubChem CID

11159021

CLP index number

No data found

Molecular mass

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 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

Beige coloured solid

Formulations

Property

Value

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

Bayer CropScience

Example products using this active

Infinito

Formulation and application details

Available as dispersible granules that are mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2.8

Low

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

200

n-Hexane

19200

Ethanol

20500

Toluene

74700

Acetone

Melting point (°C)

150

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

320

Flashpoint (°C)

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

7.94 X 10⁰²

Calculated

Log P

2.9

Moderate

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.65

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.03 X 10^-04

Low volatility

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

4.15 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 203nm = 44519, 271nm = 3601

Surface tension (mN m⁻¹)

71.3

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

271

Persistent

DT₅₀ (lab at 20 °C)

270.8

Persistent

DT₅₀ (field)

138.8

Persistent

DT₉₀ (lab at 20 °C)

899.5

Very persistent

DT₉₀ (field)

941.8

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 194-333 days (normalised), DT₉₀ range 644-1106 days (normalised); Field studies DT₅₀ range 77-224 days (normalised), DT₉₀ range 619-1184 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.3

Note

Cabbage leaves, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

7.4

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

Stable

Note

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

Value

Stable

Note

Not pH sensitive

Water-sediment DT₅₀ (days)

1117

Stable

Water phase only DT₅₀ (days)

91.4

Stable

Sediment phase only DT₅₀ (days)

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

4.20

Moderately mobile

K_foc (mL g⁻¹)

321.1

¹/_n

0.90

Notes and range

EU dossier K_f range 1.42-9.27, K_foc range 172-580 mL g⁻¹, ¹/_n range 0.86-0.93, Soils=8

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.20

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

4.34 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

80.95

Calculated using the Atkinson method. Assumed 0.5E+06 OH/cm³, 24 hr

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

121

Threshold for concern

CT₅₀ (days)

0.51

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-sulfo-5-trifluoromethylpyridine-2-carboxylic acid (Ref: AE 1344123; M10)

3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid (Ref: AE-C657188)

Minor fraction

0.073

3-methylsulfinyl-5-trifluoro-methylpyridine-2-carboxylic acid (Ref: AE 1344122; M05)

3-mesyl-5-(trifluoromethyl)pyridin-2-ol (Ref: AE 1388273; M14)

3,5-dichloro-4-[3-chloro-5-trifluoromethylpyridine-2-yl-methyl) carbamoyl] benzenesulfonic acid (Ref: AE 1413903; M15)

4-N-[3-chloro-5-trifluoromethyl-pyridin-2-yl-(hydroxyl)methyl]-2,6-dichlorobenzamide (Ref: AE-0608000)

Major fraction

0.106

2,6-dichlorobenzamide (Ref: AE C653711)

Major fraction

0.250

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)

3,5-dichloro-4-[3-chloro-5-trifluoromethylpyridine-2-yl-methyl) carbamoyl] benzenesulfonic acid (Ref: AE 1413903; M15)

Not relevant

3-sulfo-5-trifluoromethylpyridine-2-carboxylic acid (Ref: AE 1344123; M10)

Not relevant

2,6-dichlorobenzamide (Ref: AE C653711)

Not relevant

4-N-[3-chloro-5-trifluoromethyl-pyridin-2-yl-(hydroxyl)methyl]-2,6-dichlorobenzamide (Ref: AE-0608000)

Not relevant

3-methylsulfinyl-5-trifluoro-methylpyridine-2-carboxylic acid (Ref: AE 1344122; M05)

Not relevant

4-hydroxy-3-sulfo-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: M12)

Not relevant

3-chloro-4-hydroxy-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: M13)

Relevancy unknown

3-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid (Ref: AE-C657188)

Not relevant

Ref: M11

Not relevant

3-mesyl-5-(trifluoromethyl)pyridin-2-ol (Ref: AE 1388273; M14)

Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2,6-dichloro-3-hydroxybenzamide (Ref: AE C657378; M04)

Plant; Rat

3-methylsulfinyl-5-trifluoro-methylpyridine-2-carboxylic acid (Ref: AE 1344122; M05)

Plant

2,6-dichloro-N-((3-chloro-5-trifluoromethylpyridine-2-yl)methyl)-3-hydroxybenzamide (Ref: AE C643890; M06)

Plant; Animal

2,6-dichloro-N-[(3-chloro-5-trifluoromethylpyridin-2-yl)methyl]-4-hydroxy benzamide (Ref: AE 0712556; M07)

Animal

3-chloro-2-hydroxy-5-trifluoromethylpyridine (Ref: AE B102859; M09)

Plant

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)

Rabbit

High

(ppm diet)

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

> 103.4

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1744 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

88.9

Colinus virginianus NOEC

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

62.5

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 1.84 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

31.25

Folsomia candida

Non-target plants

> 3000

Lettuce Cucumber
Seedling emergence, ER₅₀
as g ha⁻¹

> 3000

OSR
Vegetative vigour, ER₅₀
as g ha⁻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)

> 241

Apis mellifera

Low

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

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 LR₅₀ g ha⁻¹ 48 hr

8230

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

7130

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)

0.36

Oncorhynchus mykiss

Moderate

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

0.155

Pimephales promelas 35 day

Moderate

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

1.7

Danio rerio

Moderate

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

> 1.8

Daphnia magna

Moderate

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

0.37

Daphnia magna

Moderate

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

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)

Chironomus riparius

Moderate

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

> 3.2

Lemna gibba

Moderate

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

0.029

Navicula pelliculosa Biomass

Moderate

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

Mesocosm study data

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.16

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.08

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

0.18

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

Dermal penetration studies (%)

0.24-2.75

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks for bystanders identified

Occupational

Potential risk to operators if PPE/PPC not utilised

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=0.24 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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, kidney and spleen toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Environment: H400, H410

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

TRANSLATIONS

Language

Name

English

fluopicolide

French

fluopicolide

German

Fluopicolid

Danish

fluopicolid

Italian

fluopicolide

Spanish

fluopicolida

Greek

Polish

fluopikolid

Swedish

fluopikolid

Hungarian

Dutch

fluopicolide

Norwegian

Record last updated:	19/12/2024
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