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Fluvalinate
Last updated: 01/02/2021
(Not known by any other names)
GENERAL INFORMATION
Description
An insecticide used to control a broad range of pests
Example pests controlled
Moths, Aphids, Thrips, Leafhoppers, Beetles, Hemipteran spp.
Example applications
Cotton; Cereals; Fruit trees; Grapes; Vegetables
Efficacy & activity
-
Availability status
Obsolete
Introduction & key dates
1980, first reported
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
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
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
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
Also used in
-
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
Pesticide type
Insecticide, Acaricide, Veterinary substance
Substance group
Pyrethroid
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact and stomach action. Sodium channel modulator.
CAS RN
69409-94-5
EC number
-
CIPAC number
-
US EPA chemical code
109302
PubChem CID
50516
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
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
3A
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Blattella germanica, Ctenocephalides felis, Heliothis virescens, Myzus persicae, Phyllonorycter blancardella, many others
Physical state
Viscous, yellow oil
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Apistan
  • Klartan
  • Minadox
  • Yardex
  • Mavrik
Example products using this active
  • Nippon Saoda
  • Zoecon
Formulation and application details
Available in a range of formulations including emulsifiable concentrates, suspensions and flowable formulations
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 (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 internet resources
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 (click here )
3 = Unverified data of known source
 High
Bulk 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 (click here )
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
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)
7
G3 G = Extension Toxicology network database EXTOXNET (click here )
3 = Unverified data of known source
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
General literature gives DT₅₀ 6-8 days
Dissipation rate RL₅₀ on plant matrix
Value
3.0
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
Note
Chickpea pods, n=1
Dissipation rate RL₅₀ on and in plant matrix
Value
1.95
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
Note
Published literature RL₅₀ range 1.7-2.4, field grown okra & pepper, n=3
Aqueous photolysis DT₅₀ (days) at pH 7
Value
1
G3 G = Extension Toxicology network database EXTOXNET (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 (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)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
1000000
G3 G = Extension Toxicology network database EXTOXNET (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
- - -
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated - -
Note
-
Potential for particle bound transport index
- - -
Potential for loss via drain flow
- - -
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
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
261
G3 G = Extension Toxicology network database EXTOXNET (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 (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)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.0009
G3 G = Extension Toxicology network database EXTOXNET (click here )
3 = Unverified data of known source
Lepomis macrochirus		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.000033
P3 P = Other governments and regulators
3 = Unverified data of known source
Pimephales promelas 30 day		 High
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.074
G3 G = Extension Toxicology network database EXTOXNET (click here )
3 = Unverified data of known source
Daphnia magna		 High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
0.0029
G3 G = Extension Toxicology network database EXTOXNET (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)
- - -
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)
- - -
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
- - -
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 (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 (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
-
MRLs
European
EU MRL pesticide database 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
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
?Possibly, status not identified
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
-
EC Risk Classification
Xn - Harmful: R22
Xi - Irritant: R38
N - Dangerous for the environment: R50, R53
EC Safety Classification
S2, S24, S59, S61
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
fluvalinate
French
fluvalinate
German
Fluvalinate
Danish
fluvalinat
Italian
fluvalinato
Spanish
fluvalinate
Greek
fluvalinate
Polish
fluwalinat
Swedish
fluvalinat
Hungarian
-
Dutch
fluvalinaat
Record last updated: 01/02/2021
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