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Fluvalinate
Last updated: 09/01/2024
(Not known by any other names)
GENERAL INFORMATION
Description
A topical pyrethroid insecticide used to control a broad range of animal pests but now considered to be obsolete
Availability status
Considered obsolete but may be available in some countries
Introduction & key dates
1980, first reported
Examples of veterinary uses
Used to control common insect pests such as mites, ticks and fleas
Examples of species treated
Cattle
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
Fluvalinate is a chiral molecule. Technical fluvalinate material is an isomeric mixture of the R- and S-isomers. However, commerical products now only use the R-isomer (tau-fluvalinate)
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
No data
International Chemical Identifier key (InChIKey)
INISTDXBRIBGOC-UHFFFAOYSA-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
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Antiinfective
Substance groups
Pyrethroid insecticide; Pyrethroid acaricide; Pyrethroid ester insecticide; Pyrethroid ester acaricide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact and stomach action. Sodium channel modulator.
Molecular targets
[Sodium channel, Modulator]
CAS RN
69409-94-5
EC number
805-993-1
CIPAC number
432
US EPA chemical code
109302
PubChem CID
50516
CLP index number
No data found
Therapeutic Class
Nervous system: Anesthetics; Psycholeptics
ATCvet Code
QP53AC10
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
502.91
PIN (Preferred Identification Name)
(RS)-a-cyano-3-phenoxybenzyl N-(2-chloro-a,a,a-trifluoro-p-tolyl)-DL-valinate
IUPAC name
(RS)-α-cyano-3-phenoxybenzyl N-(2-chloro-α,α,α-trifluoro-p-tolyl)-DL-valinate
CAS name
cyano(3-phenoxyphenyl)methyl N-[2-chloro-4-(trifluoromethyl)phenyl]-DL-valinate
Other status information
Potential groundwater pollutant; PAN Bad Chemical Actor
Relevant Environmental Water Quality Standards
-
Physical state
Viscous, yellow oil
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.002
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
25
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
7.08 X 1003 Calculated -
Log P
3.85
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
Soluble
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Data type
Regulatory data - observed in metabolism and farm animal feeding studies
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Density (g ml⁻¹)
- - -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
0.013
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
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)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
7
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
General literature gives DT₅₀ 6-8 days
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
1
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Moderately fast
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 Stable
Note
Stable under normal environmental temperatures and pH
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.
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
1000000
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 -
Koc
-
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
3-phenoxy benzoic acid - Water (photolysis) - -
anilino acid - Water (photolysis) - -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
261
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 2510
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
Colinus virginianus		 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)
- - -
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)
0.0009
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
Lepomis macrochirus		 High
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
0.000033
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Pimephales promelas 30 day		 High
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.074
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
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)
0.0029
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
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
- - -
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)
261
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
20000
G3 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
3 = Unverified data of known source
 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
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
-
Mammalian dose elimination route and rate
Mainly metabolised and excreated in urine but a proportion is excreted unchanged in faeces
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
✓Yes, known to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
✓Yes, known to cause a problem
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
✓Yes, known to cause a problem
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
Liver and kidney toxicant
Endocrine issues - Binding to human sex hormone, inhibition of progesterone production
Handling issues
Property
Value and interpretation
General
Not explosive
CLP classification 2013
-
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
fluvalinate
French
fluvalinate
German
Fluvalinate
Danish
fluvalinat
Italian
fluvalinato
Spanish
fluvalinate
Greek
fluvalinate
Polish
fluwalinat
Swedish
fluvalinat
Hungarian
-
Dutch
fluvalinaat
Norwegian
-
Record last updated: 09/01/2024
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