Tau-fluvalinate (Ref: SAN 527l)

Tau-fluvalinate (Ref: SAN 527l)	Last updated: 11/10/2023
(Also known as: taufluvalinate; MK 128; fluvalinate)

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 acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

Main application is to control Varroa mite in beehives.

Availability status

Current

Introduction & key dates

1985

Examples of species treated

Bees

Chemical structure

Isomerism

Isomeric mixture. Epimeric.

Chemical formula

C₂₆H₂₂ClF₃N₂O₃

Canonical SMILES

CC(C)C(C(=O)OC(C#N)C1=CC(=CC=C1)OC2=CC=CC=C2)NC3=C(C=C(C=C3)C(F)(F)F)Cl

Isomeric SMILES

CC(C)[C@H](C(=O)OC(C#N)C1=CC(=CC=C1)OC2=CC=CC=C2)NC3=C(C=C(C=C3)C(F)(F)F)Cl

International Chemical Identifier key (InChIKey)

INISTDXBRIBGOC-XMMISQBUSA-N

International Chemical Identifier (InChI)

InChI=1S/C26H22ClF3N2O3/c1-16(2)24(32-22-12-11-18(14-21(22)27)26(28,29)30)25(33)35-23(15-31)17-7-6-10-20(13-17)34-19-8-4-3-5-9-19/h3-14,16,23-24,32H,1-2H3/t23?,24-/m1/s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Insecticide, Acaricide

Substance groups

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

Minimum active substance purity

920 g kg⁻¹

Known relevant impurities

EU dossier - toluene 5g kg⁻¹

Substance origin

Synthetic

Mode of action

Contact and stomach action. Sodium channel modulator.

Molecular targets

CAS RN

102851-06-9

EC number

600-363-0

CIPAC number

786

US EPA chemical code

109302

PubChem CID

91768

CLP index number

607-238-00-X

ATCvet Code

QP53AC10

Therapeutic Class

Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: Bees)

Molecular mass

502.9

PIN (Preferred Identification Name)

(RS)-a-cyano-3-phenoxybenzyl N-(2-chloro-a,a,a-trifluoro-p-tolyl)-D-valinate

IUPAC name

(RS)-α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-D-valinate

CAS name

cyano(3-phenoxyphenyl)methyl N-(2-chloro-4-(trifluoromethyl)phenyl)-D-valinate

Other status information

Relevant Environmental Water Quality Standards

Physical state

Colourless viscous liquid

Related substances & organisms

fluvalinate

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

Apistan

Vita (Europe) Ltd

UK National authorisation

Authorised veterinary medicine for general sale (AVM - GSL)

Formulation and application details

Often supplied as an oil in water emulsion that is mixed with water and used as a crop spray. For use in beehives, impregnated strips are available.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.00103

Low

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

100000

Hexane

500000

Acetone

500000

Methanol

500000

Toluene

Melting point (°C)

-14.1

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

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

1.05 X 10⁰⁷

Calculated

Log P

7.02

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.266

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

4.55 X 10^-08

Low volatility

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

1.20 X 10^-04

Non-volatile

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

Neutral solution: 257nm = 17614, 300nm = 2276
Acidic solution: 257nm = 17295, 300nm = 2262
Basic solution: 257nm = 24324, 300nm = 4108

Surface tension (mN m⁻¹)

Refractive Index

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

27.8

Non-persistent

DT₅₀ (field)

3.5

Non-persistent

DT₉₀ (lab at 20 °C)

137.5

Persistent

DT₉₀ (field)

41.4

Note

EU dossier lab studies DT₅₀ range 8.1-89.1 days (normalised), DT₉₀ range 49.6-295.9 days; field studies DT₅₀ range 1.64-8.95 days, DT₉₀ range 11.8-307 days

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

Data for summer sunlight at 40 deg N

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

Value

22.5

Non-persistent

Note

pH sensitive: DT₅₀ 48 days at pH 5, 1.25 days at pH 9, all at 20 °C

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

3000

Non-mobile

K_oc

135000

Notes and range

EU dossier K_d range 1000-4608 mL g⁻¹, K_oc range 110000-160000 mL g⁻¹, Soils=9

Freundlich

K_f

970

Non-mobile

K_foc

186000

¹/_n

0.92

Notes and range

EU dossier K_f range 340-1600 mL g⁻¹, K_foc range 31000-340400 mL g⁻¹, ¹/_n range 0.73-1.1, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.69

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

1979

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

anilino acid

Major fraction

0.199

Adama verified data

haloaniline

Major fraction

0.289

Adama verified data

4-{[(1R)-1-carboxy-2-methylpropyl]amino}-3-chlorobenzoic acid

Photolysis

2-amino-2-oxo-1-(3-phenoxyphenyl)ethyl N-[2-chloro-4-(trifluoromethyl)phenyl]-D-valinate

Photolysis

3-phenoxybenzoic acid

Major fraction (anaerobic)

0.714

Anaerobic; Adama verified data

3-phenoxybenzaldehyde

Photolysis

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

anilino acid

Relevancy unknown

haloaniline

Relevancy unknown

3-phenoxybenzoic acid

Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-{[2-chloro-4-(trifluoromethyl)phenyl]amino}-4-methyl-2-(3-phenoxyphenyl)pentanenitrile

decarboxy fluvalinate

Plant

3-(4-hydroxyphonoxy)benzoic acid

Animal (Urine)

decarboxy-fluvalinate
Note: Rat Oral LD50 >2000

Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

546

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

≥ 40

Unknown species Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2510

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 455 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Colinus virginianus NOEC

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

1.44

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 1.44 kg ha⁻¹ 28 days

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

9.6

Folsomia candida 28d

Non-target plants

Honeybees (Apis spp.)

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

Apis mellifera

Moderate

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

12.6

Apis mellifera

Moderate

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)

31.3

Bombus terrestris

Moderate

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) as % Mortality at dose 48 g ha⁻¹

100

Coccinella septempunctata Larvae

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

< 48

Aphidius rhopalosiphi adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

0.049

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.000794

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.000064

Pimephales promelas 35 day

High

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

0.0089

Daphnia magna

High

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

0.000021

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)

0.00024

Chironomus riparius

High

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)

> 42.0

Scenedesmus subspicatus

Low

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

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)

546

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.56

Rat

Other Mammal toxicity endpoints

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

0.005

Rat SF=100

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

0.05

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)

0.0044

Rat

Dermal penetration studies (%)

0.15-3.09

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Risks only acceptable if PPE/PPC worn

Mammalian dose elimination route and rate

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

Possible liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H315
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

UN2810

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

tau-fluvalinate

French

tau-fluvalinate

German

Tau-fluvalinate

Danish

tau-fluvalinat

Italian

tau-fluvalinato

Spanish

tau-fluvalinate

Greek

tau-fluvalinate

Polish

tau-fluwalinat

Swedish

tau-fluvalinat

Hungarian

Dutch

tau-fluvalinaat

Norwegian

tau-fluvalinat

Record last updated:	11/10/2023
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