Flupyradifurone (Ref: BYI 02960)

Flupyradifurone (Ref: BYI 02960)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A novel insecticide used to control sucking pests in a variety of cropping situations.

Example pests controlled

Aphids, Hoppers, Whiteflies, Cicadas, Colorado potato beetle, Squash bugs, Psyllids.

Example applications

Vegetables; Fruits; Grapes; Date palm; Coffee; Cocoa

Efficacy & activity

Availability status

Current

Introduction & key dates

2012 discovered

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

09/12/2025

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

09/12/2025

EU Candidate for substitution (CfS)

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

USA

Chemical structure

Isomerism

Chemical formula

C₁₂H₁₁ClF₂N₂O₂

Canonical SMILES

C1C(=CC(=O)O1)N(CC2=CN=C(C=C2)Cl)CC(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

QOIYTRGFOFZNKF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H9ClF2N2O2/c12-9-2-1-7(4-15-9)16(5-10(13)14)8-3-11(17)18-6-8/h1-4,10H,5-6H2

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Butenolide

Minimum active substance purity

>960 g kg⁻¹

Known relevant impurities

EU Dossier: none delcared

Substance origin

Synthetic

Mode of action

Systemic, a nicotinic AChR agonist active via ingestion and contact. It is an adult knockdown product that also offers some control of nymph and egg stages.

CAS RN

951659-40-8

EC number

CIPAC number

US EPA chemical code

122304

PubChem CID

16752772

Molecular mass

288.68

PIN (Preferred Identification Name)

4-([(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino)furan-2(5H)-one

IUPAC name

4-((6-chloro-3-pyridylmethyl)(2,2-difluoroethyl)amino)furan-2(5H)-one

CAS name

4-(((6-chloro-3-pyridinyl)methyl)(2,2-difluoroethyl)amino)-2(5H)-furanone

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White powder with weak, uncharacteristic odour at 99.4% purity

Formulations

Property

Value

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

Sivanto

Example products using this active

Bayer CropScience

Formulation and application details

The main available formulations are those for foliar and drench/drip use and a seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3200

High

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

0.05

n-Heptane

3700

Toluene

250000

Ethyl acetate

250000

Methanol

Melting point (°C)

69.0

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

270

Flashpoint (°C)

Not expected to self-ignite; Not highly flammable

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

1.58 X 10⁰¹

Calculated

Log P

1.2

at 25 °C

Low

Bulk density (g ml⁻¹)

1.43

Dissociation constant pKa) at 25 °C

No dissociation

Vapour pressure at 20 °C (mPa)

9.1 X 10^-04

Low volatility

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

8.2 X 10^-08

Non-volatile

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

pH 7.0: 213nm=9615; 259nm=25800
pH 2.0: 214nm=9389, 259nm=26577
pH 10.0: 213nm=9996; 259nm=25955

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

57.1

Moderately persistent

DT₅₀ (lab at 20 °C)

57.1

Moderately persistent

DT₅₀ (field)

130

Persistent

DT₉₀ (lab at 20 °C)

522.5

Very persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 38.6-210 days, DT₉₀ range 209-898 days, Soils =16; Manufacturers data DT₅₀ lab studies range 33-371 days; DT₅₀ field ranges 8.3 - 251 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.35

Fast

Note

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

Value

Note

Water-sediment DT₅₀ (days)

230

Slow

Water phase only DT₅₀ (days)

31.4

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

98.4

Notes and range

Data for European and US soils; Brazilian soils K_oc = 333 mL g⁻¹

Freundlich

K_f

2.26

Moderately mobile

K_foc

98.4

¹/_n

0.866

Notes and range

EU dossier K_f range 0.597-3.822 mL g⁻¹, K_foc range 85.2-132.2 mL g⁻¹, ¹/_n range 0.845-0.902, Soils=6

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

4.24

Calculated

High leachability

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

Value

1.77 X 10⁰⁰

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

6-chloronicotinic acid

Soil

0.171

Major fraction; Relevant

difluoroacetic acid

Soil

0.339

Major fraction; Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-[(2,2-difluoroethyl)amino]furan-2(5H)-one

DFEAF

Plants; Livestock; Soil; Water

(6-chloropyridin-3-yl)methanol

CHMP

flupyradifuronehydroxy

BYI 02960-hydroxy

flupyradifuronesuccinamide

BYI 02960-succinamide

flupyradifuroneazabicyclosuccinamide

BYI 02960-azabicyclosuccinamide

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 300

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

232

Colinus virgianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 70.5

Pimephales promelas

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

4.4

Pimephales promelas

Moderate

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

> 77.6

Daphnia magna

Moderate

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

3.2

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)

> 67.7

Lemna gibba

Low

Non-target plants

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

> 100

Pseudokirchneriella subcapitata

Low

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)

> 200

Apis mellifera

Low

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

1.2

Apis mellifera

Moderate

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)

> 100

Bombus terrestris

Low

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)

10.59

Osmia bicornis

Moderate

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)

185.6

Eisenia foetida

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.5

<
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

17.3

Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 3.34 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)

> 300

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.67

Rat

Other Mammal toxicity endpoints

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

0.064

Rat SF=100

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

0.15

Rabbit 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)

0.06

Rat SF=100

Dermal penetration studies (%)

0.4-17

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

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

Liver and thyroid target organs

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302, H373
Environment: H400, H410, H412

EC Risk Classification

None allocated at this time

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

flupyradifurone

French

flupyradifurone

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	12/01/2021
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