Fenpropathrin (Ref: OMS 1999)

Fenpropathrin (Ref: OMS 1999)	Last updated: 02/01/2021
(Also known as: S 3206)

GENERAL INFORMATION

Description

An acaricide and insecticide used to control many species of mite and other insects

Example pests controlled

Mites; Whiteflies; Leaf miners; Armyworms; Loopers; Aphids; Tortrix moths; Cutworms; Stem borers

Example applications

Fruit including apples, citrus, currants, grapes and peaches; Vegetables including beans, cabbage, cucumber, aubergine; Cotton; Hops; Maize

Efficacy & activity

Availability status

Current

Introduction & key dates

1981, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

Expired

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

A chiral molecule existing in the S- and R-forms. The commercial product is mixture of stereoisomers, the (S)-isomer primarily responsible for the bioactivity.

Chemical formula

C₂₂H₂₃NO₃

Canonical SMILES

CC1(C(C1(C)C)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

XQUXKZZNEFRCAW-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H23NO3/c1-21(2)19(22(21,3)4)20(24)26-18(14-23)15-9-8-12-17(13-15)25-16-10-6-5-7-11-16/h5-13,18-19H,1-4H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
fenpropathrin	-

General status

Pesticide type

Insecticide, Acaricide

Substance group

Pyrethroid

Minimum active substance purity

>90%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic with contact and stomach action. Sodium channel modulator.

CAS RN

39515-41-8

Alternative/old CAS RN

64257-84-7

EC number

254-485-0

CIPAC number

426

US EPA chemical code

127901

PubChem CID

47326

Molecular mass

349.42

PIN (Preferred Identification Name)

rac-(R)-cyano(3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropane-1-carboxylate

IUPAC name

(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate

CAS name

cyano(3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropanecarboxylate

Other status information

OSPAR soc; Severe Marine Pollutant; 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

Aphis gossypii, Bemisia tabaci, Bemisia argentifolii, Scirtothrips citri, Tetranychus cinnabarinus, Tetranychus urticae, Trialeurodes vaporariorum

Physical state

Yellow-brown solid with characteristic odour

Related substances & organisms

acephate

fenitrothion

Formulations

Property

Value

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

Danitol
Fenthrin
Platino
Rody
Meothrin

Example products using this active

Agro-Care Chemical Industry Group Ltd
Valent U.S.A. Corp.
Fortune Ag
Sumitomo

Formulation and application details

Usually supplied as an emulsifiable concentrate or suspension concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.33

Low

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

25200

Methanol

23000

n-Hexane

50000

Xylene

50000

Ethyl acetate

Melting point (°C)

47.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

205

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

1.10 X 10⁰⁶

Calculated

Log P

6.04

High

Bulk density (g ml⁻¹)

1.15

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.76

Low volatility

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

1.82 X 10⁰¹

Moderately volatile

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)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ on plant matrix

Value

5.0

Note

Mandarin leaves, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

1.8

Note

Published literature RL₅₀ range 0.9-4.1 days, 4 field & undercover grown crops, various matrices, n=4

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Slow

Note

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

Value

1130

Very persistent

Note

Water-sediment DT₅₀ (days)

Fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

5000

Notes and range

Freundlich

K_f

283.5

Non-mobile

K_foc

35660

¹/_n

Notes and range

K_f range 184-486 mL g⁻¹, K_foc range 22105-51158 mL g⁻¹, ¹/_n - no data, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.80

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

Potential for loss via drain flow

Non-mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2,2,3,3-tetramethylcyclopropanecarboxylic acid

TMCA

Plants

3-(4-hydroxyphenoxy)benzoic acid

4'HO3PBA

Animal

dephenyl-fenpropathrin

Soil

4'-hydroxy-fenpropathrin

Soil

3-phenoxybenzoic acid

Soil; Animal

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

1100

Whole fish

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

870

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.5

Rat

High

(ppm diet)

100

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

Birds - Acute LD₅₀ (mg kg⁻¹)

1089

Anas platyrhynchos

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)

> 0.0023

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 0.00053

Daphnia magna

High

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

0.00022

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)

Unknown species

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)

> 0.05

High

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)

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)

184

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

% Effect

Harmful

[Dose: 300 g ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Moderately harmful

[Dose: 300 g ha⁻¹]
Chrysoperla carnea

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)

870

Rat

Moderate

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

870

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.096

Rat

Other Mammal toxicity endpoints

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

0.03

JMPR 1993

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

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

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

; ; ; ;

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

Highly toxic

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H301, H312, H330
Environment: H400, H410

EC Risk Classification

T+ - Very toxic: R26
T - Toxic: R25
Xn - Harmful: R21
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S28, S36/37, S38, S45, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

fenpropathrin

French

fenpropathrine

German

Fenpropathrin

Danish

fenpropathrin

Italian

fenpropatrin

Spanish

fenpropatrin

Greek

Polish

fenpropatryna

Swedish

fenpropatrin

Hungarian

Dutch

Record last updated:	02/01/2021
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