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Cyhalothrin (Ref: OMS 2011)
Last updated: 18/06/2020
(Also known as: PP 563; cyhalothrine)

GENERAL INFORMATION
Description
An insecticide and acaricide used to control crops pests and animal ectoparasites
Example pests controlled
Whitefly; Cutworms; Leafminers; Red spidermite
Example applications
Ornamentals; Apples & pears
Efficacy & activity
-
Availability status
Current
Introduction & key dates
circa 1982, Australia
UK regulatory status
UK approval status
Not approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Not approved
Dossier rapporteur/co-rapporteur
-
Date inclusion expires
Expired
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
Yes
Approved for use (✓) or known to be used (#) in the following EU-27 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
A chiral molecule that consists of a mixture of four stereoisomers.
Chemical formula
C₂₃H₁₉ClF₃NO₃
Canonical SMILES
CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(C(F)(F)F)Cl)C
Isomeric SMILES
CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C(/C(F)(F)F)\Cl)C
International Chemical Identifier key (InChIKey)
ZXQYGBMAQZUVMI-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18?,20-/m1/s1
2D structure diagram/image available?
Yes
General status
Pesticide type
Insecticide, Veterinary substance
Substance group
Pyrethroid
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic with contact and stomach action. Some repellant properties. Sodium channel modulator.
CAS RN
68085-85-8
EC number
268-450-2
CIPAC number
405
US EPA chemical code
128867
PubChem CID
5281873
Molecular mass
449.85
PIN (Preferred Identification Name)
rac-(E)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
IUPAC name
(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS)-3-[(Z)-2-chloro-3,3,3-trifluoropropenyl]-2,2-dimethylcyclopropanecarboxylate
CAS name
cyano(3-phenoxyphenyl)methyl (1R,3R)-rel-3-((1Z)-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
Other status information
PAN Listed as Highly Hazardous Chemical; OSPAR soc; 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)
3
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
Aphis gossypii, Helicoverpa armigera, Spodoptera litura, Tribolium castaneum, Haematobia irritans, many others
Physical state
Yellow-brown viscous oil
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
-
Example products using this active
-
UK LERAP status
No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.004
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone
-
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol
-
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene
-
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Ethyl acetate
-
Melting point (°C)
Not applicable
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Boiling point (°C)
Decomposes before boiling
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Degradation point (°C)
275
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Flashpoint (°C)
204
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
(closed cup)
-
Octanol-water partition coefficient at pH 7, 20 °C
P
6.31 X 1006 Calculated -
Log P
6.8
B2 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
2 = Unverified data of unknown source
High
Bulk density (g ml⁻¹)
1.25
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Hydrolysis prevents accurate determination
Vapour pressure at 20 °C
1.00 X 10-09
B3 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C
1.80 X 10-02
H4 H = The US ARS pesticide properties database (click here )
4 = Verified data
Non-volatile
GUS leaching potential index
-2.20 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
High Calculated -
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)
57
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
57
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Moderately persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Lab studies DT₅₀ range 32-82 days
Dissipation rate RL₅₀ on plant matrix
Value
5.2
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature RL₅₀ range 3.4-10.8 days, 5 field crops, various matrices, n=5
Dissipation rate RL₅₀ on and in plant matrix
Value
4.9
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Note
Published literature RL₅₀ range 1.6-10.3 days, 3 field crops, various matrices, n=3
Aqueous photolysis DT₅₀ (days) at pH 7
Value
Stable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Stable
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Note
Hydrolysed slowly pH 7 to pH 9, faster at pH 9
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
H3 H = The US ARS pesticide properties database (click here )
3 = Unverified data of known source
Non-mobile
Koc
180000
Notes and range
Best available data
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
(RS)-alpha-amido-3-phenoxybenzyl-(1-RS)-cis,trans-3-(ZE-2-chloro-3,3,3-trifluoro prop-1-enyl)-2,2-dimethylcyclopropanecarboxylate - Soil - -
(1RS)-Cis-3-(2-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-car boxylic acid - Soil (Aerobic) - -
3-phenoxybenzoic acid - Soil (Aerobic) - -
3-phenoxybenzaldehyde 3-PBAl Plants; Soil (Aerobic) - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
1950
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Whole fish
Threshold for concern
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
140
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Rat
Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
2.4
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Rat
High
(ppm diet)
20 -
Birds - Acute LD₅₀ (mg kg⁻¹)
5000
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Anas platyrhynchos
Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.00046
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
Lepomis macrochirus
High
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.38
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
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)
- - -
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)
0.027
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
High
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)
> 1000
R4 R = Peer reviewed scientific publications
4 = Verified data
Eisenia foetida
Low
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)
140
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Rat
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
200
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.086
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rar 4 hr
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.005
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
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.02
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
JMPR 2007
-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
0.0025
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
EU 2001
-
Dermal penetration studies (%)
0.3
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
EU 2001
-
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
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
Yes, known to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
No data found
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
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
Moderately toxic
Handling issues
Property
Value and interpretation
General
Prevent generation of dust
CLP classification 2013
Health: H301, H312, H330
Environment: H400, H410
EC Risk Classification
Xn - Harmful: R20, R21, R22
N - Dangerous for the environment: R50 R53
EC Safety Classification
S13, S60, S61
WHO Classification
II (Moderately hazardous)
UN Number
3352
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
cyhalothrin
French
cyhalothrine
German
Cyhalothrin
Danish
cyhalothrin
Italian
cialotrina
Spanish
cihalotrina
Greek
-
Polish
cyhalotryna
Swedish
-
Hungarian
cihalotrin
Dutch
-

Record last updated: 18/06/2020
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