Fluopicolide (Ref: AE C638206)

Fluopicolide (Ref: AE C638206)	Last updated: 28/01/2021
(Not known by any other names)

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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2026

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/Spain

Date EC 1107/2009 inclusion expires

31/05/2023

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

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⁻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

CIPAC number

787

US EPA chemical code

027412

PubChem CID

11159021

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 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

Beige coloured solid

Related substances & organisms

propamocarb hydrochloride

Formulations

Property

Value

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

Infinito

Example products using this active

Bayer CropScience

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)

Not expected to self ignite; Not highly flammable

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

7.94 X 10⁰²

Calculated

Log P

2.9

Moderate

Bulk 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

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 on plant matrix

Value

4.3

Note

Cabbage leaves, n=1

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

4.20

Moderately mobile

K_foc

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

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

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

Soil; Groundwater

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

Soil; Groundwater

3-chloro-5-trifluoromethylpyridine-2-carboxamide (Ref: AE C653598; M08)

Plant; Groundwater

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

Plant

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

Groundwater; Soil

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

Plant; Rat

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

Plant; Soil; Groundwater

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

121

Threshold for concern

CT₅₀ (days)

0.51

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

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.36

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.155

Pimephales promelas 35 day

Moderate

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

> 1.8

Daphnia magna

Moderate

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

0.37

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

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

Lemna gibba

Moderate

Non-target plants

> 3000

Lettuce Cucumber
Seedling emergence, ER₅₀
as g ha⁻¹

> 3000

OSR
Vegetative vigour, ER₅₀
as G/ha

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

0.029

Navicula pelliculosa Biomass

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

Low

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

> 241

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)

> 500

Eisenia foetida corr

Moderate

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

62.5

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

31.25

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

8230

48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

7130

7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 1.84 mg kg⁻¹ soil 28 days

Mesocosm study data

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)

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

proposed Mouse SF=100

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

0.18

proposed Rat SF=100

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

proposed Rat 90 day SF=100

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

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

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 flammable, explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, 53

EC Safety Classification

S35, S57

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

fluopicolide

French

fluopicolide

German

Fluopicolid

Danish

fluopicolid

Italian

fluopicolide

Spanish

fluopicolida

Greek

Polish

fluopikolid

Swedish

fluopikolid

Hungarian

Dutch

fluopicolide

Record last updated:	28/01/2021
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