Flucythrinate (Ref: OMS 2007)

Flucythrinate (Ref: OMS 2007)	Last updated: 26/08/2024
(Also known as: CL 222705; BAS 329; fluorocythrin)

SUMMARY

Flucythrinate is a pyrethroid insecticide once used to control a wide range of pests on various fruit and vegetables but now largely obsolete. It has a low aqueous solubility and a low volatility. It is moderately persistent in soils but less so in water. Based on its physico-chemical properties it is not expected to leach to groundwater. Toxicity data for biodiversity is sparse but high for mammals, bees, fish and aquatic invertebrates. Flucythrinate is high toxic to humans via the oral route and it is considered to be a neurotoxicant.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Bees acute contact ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide and acaricide used to control a wide range of pests on various fruit and vegetables

Example pests controlled

Aphids; Whiteflies; Beetles; Spidermites; Bollworms; Leafworms

Example applications

Fruit including citrus; Vines; Vegetables including beans, brassicas, cucurbits, Cotton; Maize; Tomatoes; Peppers

Efficacy & activity

Availability status

Current

Introduction & key dates

1982, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

A molecule with two chiral centres

Chemical formula

C₂₆H₂₃F₂NO₄

Canonical SMILES

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

Isomeric SMILES

International Chemical Identifier key (InChIKey)

GBIHOLCMZGAKNG-CGAIIQECSA-N

International Chemical Identifier (InChI)

InChI=1S/C26H23F2NO4/c1-17(2)24(18-11-13-21(14-12-18)32-26(27)28)25(30)33-23(16-29)19-7-6-10-22(15-19)31-20-8-4-3-5-9-20/h3-15,17,23-24,26H,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Acaricide

Substance groups

Pyrethroid insecticide; Pyrethroid caricide; Pyrethroid ester insecticide; Pyrethroid ester acaricide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

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

CAS RN

70124-77-5

EC number

274-322-7

CIPAC number

406

US EPA chemical code

118301

PubChem CID

50980

CLP index number

No data found

Molecular mass

451.46

PIN (Preferred Identification Name)

(E)-cyano(3-phenoxyphenyl)methyl (2S)-2-[4-(difluoromethoxy)phenyl]-3-methylbutanoate

IUPAC name

(RS)-α-cyano-3-phenoxybenzyl (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyrate

CAS name

cyano(3-phenoxyphenyl)methyl (αS)-4-(difluoromethoxy)-a-(1-methylethyl)benzeneacetate

Other status information

OSPAR soc

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Haematobia irritans, Helicoverpa armigera, Lucilia cuprina, Plutella xylostella, Scirtothrips citri, Spodoptera littoralis

Physical state

Dark amber viscous liquid

Formulations

Property

Value

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

King Tech Corp
BASF
American Cyanamid

Example products using this active

AAstar
Cybolt
Pay-Off
Fuching Jujr

Formulation and application details

Usually supplied as emulsifiable concentrates and wettable powders

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.5

Low

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

250000

Acetone

25000

Methanol

73500

n-Heptane

225000

Ethyl acetate

Melting point (°C)

Not applicable

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

(closed cup)

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

5.01 X 10⁰⁴

Calculated

Log P

4.7

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.19

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.0012

Low volatility

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

1.08 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.6

Note

Published literature RL₅₀ range 3.3-5.9 days, 3 field crops, various matrices, n=4

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

Note

pH sensitive: DT₅₀ 40 days at pH 3, 52 days at pH 5, 6.3 days at pH 9 all at 27 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

100000

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-1.32

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

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

2500

Threshold for concern

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

2510

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

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

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

0.078

Apis mellifera

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)

Chronic

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 bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

== 0.32

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000006

Oncorhynchus mykiss 54 day

High

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

0.0083

Daphnia magna

High

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

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.000006

Americamysis bahia

High

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)

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

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

Rat

High

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

1000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

4.85

Rat

Other Mammal toxicity endpoints

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

0.02

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

List II

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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

Highly toxic

Handling issues

Property

Value and interpretation

General

Flammable liquid
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H301, H312, H330, H373
Environment: H400, H410
Handling: H226

WHO Classification

Ib (Highly hazardous)

UN Number

UN1992

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flucythrinate

French

flucythrinate

German

Flucythrinat

Danish

flucythrinat

Italian

flucitrinate

Spanish

flucitrinato

Greek

Polish

flucytrynat

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	26/08/2024
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