Fluopyram

Fluopyram	Last updated: 15/11/2019
(Also known as: AE C656948)

GENERAL INFORMATION

Description

Novel broad spectrum fungicide for use as a foliar application and as a seed treatment to control various diseases. Also has nematicide activity.

Example pests controlled

Botrytis, Powdery mildew, Fusarium virguliforme

Example applications

Potatoes; Sugarbeet; Fruit including apples, grapes and strawberries; Cotton

Efficacy & activity

Availability status

Current

Introduction & key dates

2008

UK regulatory status

UK approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Approved

Dossier rapporteur/co-rapporteur

Denmark

Date inclusion expires

31/01/2024

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

First registrations expected in 2011

Chemical structure

Isomerism

Chemical formula

C₁₆H₁₁ClF₆N₂O

Canonical SMILES

C1=CC=C(C(=C1)C(=O)NCCC2=C(C=C(C=N2)C(F)(F)F)Cl)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

KVDJTXBXMWJJEF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H11ClF6N2O/c17-12-7-9(15(18,19)20)8-25-13(12)5-6-24-14(26)10-3-1-2-4-11(10)16(21,22)23/h1-4,7-8H,5-6H2,(H,24,26)/f/h24H

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Nematicide

Substance group

Benzamide, pyramide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - none declared

Substance origin

Synthetic

Mode of action

Succinate Dehydrogenase Inhibitor.

CAS RN

658066-35-4

EC number

CIPAC number

807

US EPA chemical code

080302

PubChem CID

11158353

Molecular mass

396.76

PIN (Preferred Identification Name)

N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide

IUPAC name

N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-α,α,α-trifluoro-ortho-toluamide

CAS name

N-(2-(3-chloro-5-(trifluoromethyl)-2-pyridinyl)ethyl)-2-(trifluoromethyl)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

Formulations

Property

Value

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

Fluopyram SC 500
Verango
Velum

Example products using this active

Bayer CropScience

UK LERAP status

Buffer probably required in UK - see product label

Formulation and application details

Both seed treatments and suspension concentrate products for foliar application are available

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

16.0

Low

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

250000

Acetone

250000

Dichloromethane

660

n-Heptane

62200

Toluene

Melting point (°C)

117.5

Boiling point (°C)

318

Degradation point (°C)

300

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰³

Calculated

Log P

3.3

High

Bulk density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

1.2 X 10^-03

Low volatility

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

2.98 X 10^-05

Non-volatile

GUS leaching potential index

3.23

Calculated

High leachability

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

Value

4.46 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

216nm=14877, 270nm=4332, 290nm<10

Surface tension (mN m⁻¹)

59.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

309

Persistent

DT₅₀ (lab at 20 °C)

309

Persistent

DT₅₀ (field)

118.8

Persistent

DT₉₀ (lab at 20 °C)

723

Very persistent

DT₉₀ (field)

833

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 117-717 days, DT₉₀ range 538->1000 days, Field studies DT₅₀ range 93.2-144.6 days, DT₉₀ range 487->1000 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

6.5

Note

Published literature RL₅₀ range 4.0-9.0 days, various matrices from 3 crops grown in field & undercover, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

Stable

Note

Stable at pH 5, 7 & 9 at 50 °C

Water-sediment DT₅₀ (days)

1077

Stable

Water phase only DT₅₀ (days)

20.5

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

4.41

Moderately mobile

K_foc

278.9

¹/_n

0.827

Notes and range

EU dossier K_f range 2.94-6.83 mL g⁻¹, K_foc range 233-400 mL g⁻¹, ¹/_n range 0.765-0.948, Soils=6

pH sensitivity

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-hydroxyethyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10065)

Soil

0.042

Minor fraction, Not relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)ethyl))-2-(trifluoromethyl)benzamide
Note: MWt=412.72

AE C656948-N-oxide

Plants

N-((E)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10627)
Note: MWt=394.71

AE C656948-N-olefine

Animals

N-((Z)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10650)
Note: MWt=394.71

AE C656948-Z-olefine

Animals

-
Note: MWt=586.83

AE C656948-enol-GA

Rat

-
Note: MWt=412.72

AE C656948-phenol

Animal

-
Note: MWt=574.87

AE C656948-phenol-glc

Rat

-
Note: MWt=588.85

AE C656948-phenol-GA

Animal; Rat

-
Note: MWt=412.72

AE C656948-benzamide

Animal; Rat; Plants; Soil

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranosiduronic acid
Note: MWt=588.85

AE C656948-7-OH-GA

Animal; Fish; Rat

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)phenyl)carbonyl)amino)ethyl hydrogen sulfate
Note: MWt=492.78

AE C656948-7-OH-SA

Plants

N-(2-(3-chloro-5-(trifluoromethyl)pyridine-2-yl)-2-(beta-D-glucopyranosyloxyethyl)-2-(trifluoromethyl) benzamide
Note: MWt=574.87

AE C656948-7-hydroxy-glc

Plants

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranoside
Note: MWt=660.91

AE C656948-7-hydroxy-glc-MA

Plants

-
Note: MWt=428.72

AE C656948-7-OH-phenol

Rat

-
Note: MWt=604.85

AE C656948-7-OH-phenol-GA

Rat

-
Note: MWt=508.78

AE C656948-7-OH-phenol-SA

Rat

-
Note: MWt=490.81

AE C656948-7-OH-methyl-sulfone

Rat

-
Note: MWt=524.78

AE C656948-7-OH-hydroxyphenol-SA

Rat

N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)-1-hydroxyethyl)-2-(trifluoromethyl)benzamide
Note: MWt=412.72

AE C656948-8-hydroxy

Animal; Fish; Rat; Plants

-
Note: MWt=604.85

AE C656948-di-8-OH-GA

Animal; Rat

-
Note: MWt=766.99

AE C656948-hydroxy-glyc-gluc

Plant

-
Note: MWt=634.87

AE C656948-methoxy-di-OH-GA

Rat

N-acetyl-O-(2-(trifluoromethyl)benzoyl)serine
Note: MWt=319.24

AE C656948-benzoyl-serine

Rat

-
Note: MWt=205.14

AE C656948-hydroxy-benzamide

Rat

-
Note: MWt=381.2

AE C656948-benzamide-OH-GA

Rat

-
Note: MWt=350.32

AE C656948-benzamide-cysteine

Rat

-
Note: MWt=251.23

AE C656948-BA-methyl-sulfoxide

Rat

-
Note: MWt=267.23

AE C656948-BA-methyl-sulfone

Rat

-
Note: MWt=285.2

AE C656948-benzamide-SA

Rat

1-O-((2-trifluoromethyl)benzoyl)amine)-beta-D-glucopyranuronic acid
Note: MWt=365.3

AE C656948-benzamide-N,O-GA

Rat

2-(trifluoromethyl)benzoic acid
Note: MWt=190.12

AE C656948-benzoic acid

Rat; Plants

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanol
Note: MWt=225.60

AE C656948-pyridyl-hydroxyethyl

Animals

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl beta-D-glucopyranoside
Note: MWt=387.3

AE C656948-hydroxyethyl-glc

Plants

-
Note: MWt=549.89

AE C656948-hydroxyethyl-di-glc

Plants

-
Note: MWt=401.73

AE C656948-hydroxyethyl-GA

Animal; Rat

-
Note: MWt=241.6

AE C656948-ethyl-diol

Rat

-
Note: MWt=417.73

AE C656948-ethyl-diol-GA

Rat

-
Note: MWt=239.58

AE C656948-pyrodyl-acetic acid

Animal; Rat; Plants

-
Note: MWt=255.58

AE C656948-hydroxy-PAA

Animal; Rat

-
Note: MWt=401.73

AE C656948-PAA-glycoside

Plant

-
Note: MWt=356.75

AE C656948-pyridyl-methyl-cystein

Rat

Ref: BCS-AA10634
Note: MWt=360.26

AE C656948-lactame

Photolysis

Ref: AE C657188
Note: MWt=225.26

AE C656948-pyridyl-carboxylic acid

Rat; Plants; Soil

3-(methylsulfinyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: AE 1344122)
Note: MWt=253.20

AE C656948-methyl-sulfoxide

Plants; Soil

3-chloro-2-methyl-5-(trifluoromethyl)pyridine
Note: MWt=195.57

AE C656948-picoline

1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl 6-O-(carboxyacetyl)-beta-D-glucopyranoside
Note: MWt=660.91

AE C656948-8-hydroxy-glc-MA

Plants

2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl)-beta-D-glucopyranosiduronic acid
Note: MWt=588.85

AE C656948-8-OH-GA

Animal; Fish; Rat

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

3.4

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginians

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1643 mg/Kg BW/day

Anas platyrhynchos

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.98

Coleonyx variegatus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.135

Pimephalis promelas 33 day

Moderate

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

> 100

Daphnia magna

Low

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

1.25

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)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

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

2.32

Moderate

Non-target plants

> 0.25

Fagopyrum esculentum
Seedling emergence, ER₅₀
as g ha⁻¹

> 0.50

Beta vulgais
Vegetative vigour, ER₅₀
as g ha⁻¹

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

> 1.13

Skeletonema costatum

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)

> 102.3

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

Low

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

11.42

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

103.8

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

2000

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

2000

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 3.33 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)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.11

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.012

Rat SF=100

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

0.5

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

Rat SF=100

Dermal penetration studies (%)

1-3

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for intended uses

Occupational

Acceptable for intended uses

European MRLs

EU MRL pesticide database

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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver, thyroid and blood toxicant

Handling issues

Property

Value and interpretation

General

Not oxidising or explosive
IMDG Transport Code is usually 9

CLP classification 2013

Environment: H411

EC Risk Classification

N - Dangerous for the environment: R51/53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fluopyram

French

German

Danish

Italian

Spanish

Greek

Polish

Swedish

fluopyram

Hungarian

Dutch

Record last updated:	15/11/2019
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