Penflufen (Ref: BYF-14182)

Penflufen (Ref: BYF-14182)	Last updated: 12/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A new fungicidal seed treatment of numerous crops including potatoes

Example pests controlled

Black scurf; Stem & stolon canker; Fusarium rot

Example applications

Potatoes; Cereal grains including wheat, barley; Oilseeds; Alfalfa; Legumes; Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/01/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

31/01/2024

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; Canada

Chemical structure

Isomerism

Chemical formula

C₁₈H₂₄FN₃O

Canonical SMILES

CC1=NN(C(=C1C(=O)NC2=CC=CC=C2C(C)CC(C)C)F)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

GOFJDXZZHFNFLV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H24FN3O/c1-11(2)10-12(3)14-8-6-7-9-15(14)20-18(23)16-13(4)21-22(5)17(16)19/h6-9,11-12H,10H2,1-5H3,(H,20,23)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Pyrazolium

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Succinate DeHydrogenase Inhibitor.

CAS RN

494793-67-8

EC number

CIPAC number

826

US EPA chemical code

100249

PubChem CID

11674113

Molecular mass

317.41

PIN (Preferred Identification Name)

rac-5-fluoro-1,3-dimethyl-N-{2-[(2R)-4-methylpentan-2-yl]phenyl}-1H-pyrazole-4-carboxamide

IUPAC name

2'-[(RS)-1,3-dimethylbutyl]-5-fluoro-1,3-dimethylpyrazole-4-carboxanilide

CAS name

N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

Other status information

Potential marine pollutant; PAN listed Highly Hazardous Chemical

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

None identified

Physical state

Off-white coloured powder

Formulations

Property

Value

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

EverGol prime
Emesto Quantum
EverGol Extend

Example products using this active

Formulation and application details

Usually applied as a seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

10.9

Low

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

126000

Methanol

1600

n-Heptane

62000

Toluene

139000

Acetone

Melting point (°C)

111

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

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)

4.1 X 10^-04

Low volatility

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

1.05 X 10^-05

Non-volatile

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

Neutral soln: 209nm=23724, 232nm=10939 shoulder
Acidic soln: 202nm=25030, 230nm=11784 shoulder
Basic soln: 204nm=23010, 234nm=9868 shoulder

Surface tension (mN m⁻¹)

61.6

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

192

Persistent

DT₅₀ (lab at 20 °C)

192

Persistent

DT₅₀ (field)

113

Persistent

DT₉₀ (lab at 20 °C)

837

Very persistent

DT₉₀ (field)

595

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 115-458 days, DT₉₀ range 382-1521 days; Field studies DT₅₀ range 68-224 days, DT₉₀ range 331->1000 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

17.3

Slow

Note

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

Value

Stable

Note

Stable at pH 4,7 & 9 at 50 °C

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

246

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

4.78

Moderately mobile

K_foc

279.9

¹/_n

0.920

Notes and range

EU dossier K_f range 2.705-6.10 mL g⁻¹, K_foc range 209.6-409.5 mL g⁻¹, ¹/_n range 0.875-0.974, soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.19

Calculated

High leachability

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

Value

4.23 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

penflufen-3-hydroxy-butyl

Soil

0.17

Major fraction, Relevant

penflufen-pyrazolyl-AAP

Soil

0.115

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

BYF-14182-3,4-dihydroxy-keto-glucuronide

Animal

BYF-14182-3,4-dihydroxy-ketone

Animal

BYF-14182-homoglutathione

Plant

BYF-14182-pyrazole-4-carboximide

Plant

BYF-14182-bis-desmethyl-3-carboxylic acid

Plant

BYF-14182-4-hydroxy-butyl-malonyl-glucoside

Plant

BYF-14182-2,3,4-trihydroxy

Animal

BYF-14182-3,4-dihydroxy-glucuronide

Animal

BYF-14182-3,4-dihydroxy

Animal

BYF-14182-pentanoic acid

Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

142

Threshold for concern

CT₅₀ (days)

0.53

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Rat (male) Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 4000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1697 mg kg⁻¹ BW/day

Colinus virginianus

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

Colinus virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.103

Cyprinus carpio

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.023

Pimephales promelas 35 day

Moderate

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

> 4.66

Daphnia magna

Moderate

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

1.53

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)

> 4.7

Moderate

Non-target plants

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

> 5.1

Pseudokirchneriella subcapitata

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)

> 108.2

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

Low

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

33.0

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

493

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

250

>
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

250

>
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

Carbon mineralisation: No significant adverse effect

Dose: 3.18 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)

> 2.02

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.04

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)

0.077

Dog SF=100

Dermal penetration studies (%)

0.21-1.45

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for intended uses

Occupational

Acceptable with PPC/PPE

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible liver and thyroid toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H400, H410

EC Risk Classification

Carcinogen category 3: R40
N - Dangerous for the environment: R50/53

EC Safety Classification

WHO Classification

NL (Not listed)

UN Number

3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

penflufen

French

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