Chlorfenapyr (Ref: MK 242)

Chlorfenapyr (Ref: MK 242)	Last updated: 27/11/2019
(Also known as: AC 303630; CL 303630)

SUMMARY

Chlorfenapyr is a broad spectrum insecticide that does not have EU approval for use. It has a low aqueous solubility, low volatility and, based on its chemical properties, would not normally be expected to leach to groundwater. It is not usually persistent in soil or water systems. It has a moderate mammalian oral toxicity but no other data on human health impact has been identified. There are also gaps in ecotoxicilogical data but it is know to be highly toxic to birds, fish and aquatic invertebrates.

GENERAL INFORMATION

Description

Used to control many insects and mites including those resistant to carbamate, organophosphate and pyrethroid compounds

Example pests controlled

Spider mites; Caterpillars; Thrips; Fungus gnats

Example applications

Greenhouse ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

2001, USA

UK regulatory status

UK approval status

Not approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Not approved

Dossier rapporteur/co-rapporteur

Spain

Date inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Australia

Chemical structure

Isomerism

Isomeric

Chemical formula

C₁₅H₁₁BrClF₃N₂O

Canonical SMILES

CCOCN1C(=C(C(=C1C(F)(F)F)Br)C#N)C2=CC=C(C=C2)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

CWFOCCVIPCEQCK-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H11BrClF3N2O/c1-2-23-8-22-13(9-3-5-10(17)6-4-9)11(7-21)12(16)14(22)15(18,19)20/h3-6H,2,8H2,1H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide, Miticide

Substance group

Pyrrole

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Limited systemic activity, mainly stomach but some contact action. Uncoupler of oxidative phosphorylation.

CAS RN

122453-73-0

EC number

CIPAC number

570

US EPA chemical code

129093

PubChem CID

91778

Molecular mass

407.62

PIN (Preferred Identification Name)

4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

IUPAC name

4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile

CAS name

4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

Other status information

Chemical subject to PIC regulations

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

Earias vittella, Tetranychus urticae

Physical state

White powdery solid

Formulations

Property

Value

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

Pirate
Pylon
Shark

Example products using this active

BASF
AgroCare
FCC

UK LERAP status

No UK approval for use as a pesticide under EC Regulation 1107/2009

Formulation and application details

Usually supplied as suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.112

at 25 °C

Low

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

8900

Hexane

70900

Methanol

754000

Toluene

1410000

Dichloromethane

Melting point (°C)

101

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

6.76 X 10⁰⁴

Calculated

Log P

4.83

High

Bulk density (g ml⁻¹)

1.53

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

9.81 X 10^-03

at 25 °C

Low volatility

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

5.81 X 10^-04

at 25 °C

Non-volatile

GUS leaching potential index

-0.01

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.4

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ on plant matrix

Value

2.87

Note

Published literature RL₅₀ range 2.85-2.89 days, 2 crops, various matrices, n=2

Dissipation rate RL₅₀ on and in plant matrix

Value

3.7

Note

Published literature RL₅₀ range 1.4-7.0 days, 8 field and undercover grown crops, various matrices, n=11

Aqueous photolysis DT₅₀ (days) at pH 7

Value

6.2

Moderately fast

Note

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

12000

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-pyrroline-3-carbonitrile,4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-chlorfenapyr

Soil

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: CL 303268

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

441

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.007

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.00871

Cyprinodon variegatus 33 day

High

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

0.0061

Daphnia magna

High

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

0.00357

Daphnia magna

High

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)

Non-target plants

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

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)

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

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

0.12

Apis mellifera

High

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)

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

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

441

Rat

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

1.9

Rat

Other Mammal toxicity endpoints

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

0.015

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

0.015

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Occupational

Occupational exposure may occur through dermal contact

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possile testicular and uterine toxicant
USEPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302, H331
Environment: H400, H410

EC Risk Classification

T - Toxic: R23
Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S13, S36/37, S45, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

chlorfenapyr

French

chlorfénapyr

German

Chlorfenapyr

Danish

chlorfenapyr

Italian

clorfenapir

Spanish

clorfenapir

Greek

chlorfenapyr

Polish

chlorofenapir

Swedish

Hungarian

Dutch

chloorfenapyr

Record last updated:	27/11/2019
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