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Cyphenothrin (Ref: S 2703)
(Also known as: D,D-T-cyphenothrin; OMS 3032; d-cyphenothrin)
SUMMARY
Cyphenothrin is a pyrethroid insecticide with public health and industrial applications. It has a low aqueous solubility and is non-volatile. Whilst it is not expected to be persistent in soil systems, it may be persistent in water systems depending on local conditions. Based on its physico-chemical properties it is not expected to leach to groundwaters. It is highlt toxic to aquatic life and moderately tpxic to honeybees. Cyphenothrin is also moderately toxic to mammals if consummed.
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
Warning:
Significant data are missing
Ecotoxicity
High alert:
Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High
Human health
Moderate alert:
Mammals acute toxicity: Moderate; Possible Endocrine distrupter
GENERAL INFORMATION
Description
Used to control insect pests in non-agricultural situations
Example pests controlled
Flies; Midges; Cockroaches; Ticks; Lice; Fleas
Example applications
Domestic, public health and industrial situations
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1986, Japan
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
                 
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
Australia, USA
Chemical structure
Isomerism
Cyphenothrin is a chiral molecule. The technical material is a mixture of various optical isomers each having different insecticidal activity. Different commercial products may contain different isomers in varing proportions.
Chemical formula
C₂₄H₂₅NO₃
Canonical SMILES
CC(=CC1C(C1(C)C)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
FJDPATXIBIBRIM-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C24H25NO3/c1-16(2)13-20-22(24(20,3)4)23(26)28-21(15-25)17-9-8-12-19(14-17)27-18-10-6-5-7-11-18/h5-14,20-22H,1-4H3
2D structure diagram/image available?
Yes
General status
Pesticide type
Insecticide
Substance groups
Pyrethroid insecticide; Pyrethroid ester insecticide
Minimum active substance purity
>98%
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic, rapid knockdown with contact and stomach action damaging insects nervous system. Sodium channel modulator.
CAS RN
39515-40-7
EC number
254-484-5
CIPAC number
804
US EPA chemical code
129013
PubChem CID
38283
CLP index number
No data found
Molecular mass
375.46
PIN (Preferred Identification Name)
(E)-cyano(3-phenoxyphenyl)methyl (1E,3E)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
IUPAC name
(RS)-α-cyano-3-phenoxybenzyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CAS name
cyano(3-phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other status information
-
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
Bemisia tabaci
Physical state
Yellow viscous liquid
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Sumitomo Chemical Co
  • SC Johnson and Son
Example products using this active
  • Gokilaht
  • S2703 Forte
  • Pesguard LG OBA
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.01
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
at 25 °C		 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
48400
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane		 -
92700
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
500000
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Xylene		 -
Melting point (°C)
25
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Boiling point (°C)
154
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
130
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
4.17 X 1006 Calculated -
Log P
6.62
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.08
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
Not applicable
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
No dissociation
Vapour pressure at 20 °C (mPa)
0.12
E3 E = Manufacturers safety data sheets
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)
12
Q3 Q = Miscellaneous data from online sources
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
-
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
- - -
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
B5 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
5 = Verified data used for regulatory purposes
 Stable
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
 Non-mobile
Koc
9224
Notes and range
Estimated
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
0.04 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
5.34 X 10-03 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Non-mobile Calculated -
Bio-concentration factor
BCF (l kg⁻¹)
Low risk
V2 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
2 = Unverified data of unknown source
 Low risk
CT₅₀ (days)
- -
Known metabolites

None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
318
E3 E = Manufacturers safety data sheets
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)
> 5620
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
2.0
V2 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
2 = Unverified data of unknown source
 Moderate
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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.00034
B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
4 = Verified data
Oncorhynchus mykiss		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.000056
B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
4 = Verified data
Oncorhynchus mykiss		 High
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.00043
B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
4 = Verified data
Daphnia magna		 High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.00009
B4 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here )
4 = Verified data
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)
- - -
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)
318
E3 E = Manufacturers safety data sheets
3 = Unverified data of known source
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
5000
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 1.85
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
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
May be absorbed through the skin
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
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
Harmful if swallowed
Handling issues
Property
Value and interpretation
General
May emit toxic and irritating fumes under fire conditions
Prevent generation of spray mists
IMDG Transport Hazard Class 9
CLP classification 2013
-
WHO Classification
II (Moderately hazardous)
UN Number
UN3082
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
cyphenothrin
French
-
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
cyfenotryna
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
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