Cyhalothrin (Ref: OMS 2011)	Last updated: 04/01/2024
(Also known as: PP 563; cyhalothrine)

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SUMMARY

Cyhalothrin is a pyrethroid insecticide and acaricide. It has a low aqueous solubility and is not volatile. It may be environmentally persistent depending on local conditions. There is a low risk of cyhalothrin leaching to groundwater. It is highly toxic to fish and honeybees. Cyhalothrin has a moderate mammalian oral toxicity, an endocrine disrupter and an irritant.

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 High alert: Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Endocrine disrupter Warning: Significant data are missing

GENERAL INFORMATION

Description	An insecticide and acaricide used to control crops pests and animal ectoparasites
Availability status	Current
Introduction & key dates	circa 1982, Australia
Examples of species treated	-

Approval status

GB VMR 2013/2033 approval status	-
EU Regulatory approval status	-

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)	OOAOVGPMANECPJ-RWEUCVCFSA-N
International Chemical Identifier (InChI)	InChI=1S/4C23H19ClF3NO3/c4*1-22(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/h4*3-12,17-18,20H,1-2H3/b4*19-12-/t2*17-,18+,20-;2*17-,18-,20-/m1010/s1
2D structure diagram/image available?	Yes

General status

Veterinary substance type	-
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	Non-systemic with contact and stomach action. Some repellant properties. Sodium channel modulator.
Molecular targets	-
CAS RN	68085-85-8
EC number	268-450-2
CIPAC number	405
US EPA chemical code	128867
PubChem CID	5281873
CLP index number	No data found
ATCvet Code	-
Therapeutic Class	-
Controlled Drug?	No
Regulation 37/2010 MRL Classification	-
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	-
Physical state	Yellow-brown viscous oil
Related substances & organisms	gamma-cyhalothrin lambda-cyhalothrin

Formulations

Property	Product	Manufacturer	Authorisation Route	UK Legal Class
Example products 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)		0.004	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	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 data from online sources 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; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 2 = Unverified data of unknown 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)		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 (mPa)		1.00 X 10-09	B3 B = UK CRD and ACP Evaluation Documents / and other DEFRA (UK) documents; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		1.80 X 10-02	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Non-volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-
Refractive Index		-	-	-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
Soil degradation (days) (aerobic)	DT₅₀ (typical)	57	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	Moderately persistent
	DT₅₀ (lab at 20 °C)	57	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	Moderately persistent
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	Note	Lab studies DT₅₀ range 32-82 days
Manure DT₅₀ (days)		-	-	-
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. Dataset is no longer available. 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		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		-2.20	Calculated	Low leachability
Bio-concentration factor	BCF (l kg⁻¹)	1950	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source Whole fish	Threshold for concern
	CT₅₀ (days)	Not available		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
(RS)-alpha-amido-3-phenoxybenzyl-(1-RS)-cis,trans-3-(ZE-2-chloro-3,3,3-trifluoro prop-1-enyl)-2,2-dimethylcyclopropanecarboxylate	-	-	-
(1RS)-Cis-3-(2-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-car boxylic acid	-	-	-
3-phenoxybenzoic acid (Ref: 692)	-	-	-
3-phenoxybenzaldehyde	-	-	-

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
3-phenoxybenzaldehyde	3-PBAl	Plants	-	-

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		140	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 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; Also Chemicals Regulation Division, Health and Safety Executive (HSE), UK (click here ) 5 = Verified data used for regulatory purposes Rat	High
	(ppm diet)	20		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		5000	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 Anas platyrhynchos	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)		> 1000	R4 R = Peer reviewed scientific publications 4 = Verified data Eisenia foetida	Low
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)	0.027	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 Apis mellifera	High
	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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		0.00046	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 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 / FAO data, IPCS INCHEM data (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)		-	-	-
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)		140	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 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)		-	-	-
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 (%)		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	-
Mammalian dose elimination route and rate		-	-	-

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 IMDG Transport Hazard Class 6.1
CLP classification 2013	Health: H301, H312, H330 Environment: H400, H410
WHO Classification	II (Moderately hazardous)
UN Number	UN3352
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	cyhalothrin
French	cyhalothrine
German	Cyhalothrin
Danish	cyhalothrin
Italian	cialotrina
Spanish	cihalotrina
Greek	-
Polish	cyhalotryna
Swedish	-
Hungarian	cihalotrin
Dutch	-
Norwegian	-

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Record last updated:	04/01/2024
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