Cycloprothrin (Ref: OMS 3049)	Last updated: 05/01/2021
(Also known as: phencyclate)

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GENERAL INFORMATION

Description	Used to control rice water weevils and other insects in paddy fields and on other crops
Example pests controlled	Rice water weevils; Vine weevils; Leaf miners
Example applications	Paddy rice; Fruit and vines; Vegetables; Forestry; Cotton
Efficacy & activity	-
Availability status	Unknown
Introduction & key dates	1987, 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

Also used in

Also used in	-

Chemical structure

Isomerism	Cycloprothrin is a molecule with 2 chiral centres. The commerical product is an isomeric mixture of the 4 stereoisomers. The (1R, alphaR)-isomer demonstrates the greatest insecticidal activity being roughly 5x stronger than the racemic mixture.
Chemical formula	C₂₆H₂₁Cl₂NO₄
Canonical SMILES	CCOC1=CC=C(C=C1)C2(CC2(Cl)Cl)C(=O)OC(C#N)C3=CC(=CC=C3)OC4=CC=CC=C4
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	CGTWCAVZZBLHQH-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C26H21Cl2NO4/c1-2-31-20-13-11-19(12-14-20)25(17-26(25,27)28)24(30)33-23(16-29)18-7-6-10-22(15-18)32-21-8-4-3-5-9-21/h3-15,23H,2,17H2,1H3
2D structure diagram/image available?	Yes

General status

Pesticide type	Insecticide
Substance group	Pyrethroid
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Contact and stomach action, also has anti-feeding and repellent effects. Sodium channel modulator.
CAS RN	63935-38-6
EC number	-
CIPAC number	None allocated
US EPA chemical code	-
PubChem CID	91686
Molecular mass	482.36
PIN (Preferred Identification Name)	(E)-cyano(3-phenoxyphenyl)methyl (1E)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate
IUPAC name	(RS)-a-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate
CAS name	cyano(3-phenoxyphenyl)methyl 2,2-dichloro-1-(4-ethoxyphenyl)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)	2B
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	None identified
Physical state	Dirty yellow coloured liquid

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	-
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)		0.091	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		25.0	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
Boiling point (°C)		140	L1 L = Pesticide manuals and hard copy reference books / other sources 1 = Estimated data with little or no verification	-
Degradation point (°C)		190	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.55 X 1004	Calculated	-
	Log P	4.19	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	High
Bulk density (g ml⁻¹)		1.26	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 internet resources 3 = Unverified data of known source	-
		No dissociation
Vapour pressure at 20 °C (mPa)		0.00213	L3 L = Pesticide manuals and hard copy reference books / other sources 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)	47	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	Moderately persistent
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	Literature studies DT₅₀ range 33 days (flooded sandy clay loam) to 61 days (flooded clay loam)
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	Stable	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	Stable
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	-	-	-
	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 internet resources 2 = Unverified data of unknown source	Slightly mobile
	Koc	3200
	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		0.83	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	1.58 X 10-02	Calculated	-
	Note	-
Potential for particle bound transport index		High	Calculated	-
Potential for loss via drain flow		Slightly mobile	Calculated	-

Other known metabolites

Metabolite name and reference	Aliases	Formation medium / Rate	Estimated maximum occurrence fraction	Metabolising enzymes
2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylic acid	-	Soil	-	-

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)		> 5000	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat	Low
Mammals - Short term dietary NOEL	(mg kg⁻¹)	-	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
	(ppm diet)	20.0		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 5000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Coturnix japonica	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)		> 1.6	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		> 10.0	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Daphnia magna 3 hour	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)	-	-	-
	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)		> 5000	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		1.50	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 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	-
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 ?Possibly, status not identified 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 No data found ?Possibly, status not identified ✓Yes, known to cause a problem Eye irritant Phototoxicant   ?Possibly, status not identified No data found
General human health issues		No further information available

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	Health: H317 Environment: H400, H410
EC Risk Classification	Xi - Irritant: R36/37/38
EC Safety Classification	S26
WHO Classification	U (Unlikely to present an acute hazard)
UN Number	-
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	cycloprothrin
French	-
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-

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Record last updated:	05/01/2021
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