Piperonyl cyclonene (Ref: ENT-2818)	Last updated: 25/10/2024
(Also known as: piperonly cyclohexanone)

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GENERAL INFORMATION

Description	A substance with some insecticidal activity but mainly used as a synergist with pyrethroid insecticides and rotenone
Availability status	Current
Introduction & key dates	-
Examples of veterinary uses	-
Examples of species treated	-

Approval status

VMR 2013/2033 approval status (GB/UK)	-
EU Regulatory approval status	-

Chemical structure

Isomerism	Isomeric. Technical material is a racemate.
Chemical formula	C₁₉H₂₄O₃
Canonical SMILES	CCCCCCC1=CC(=O)CC(C1)C2=CC3=C(C=C2)OCO3
Isomeric SMILES	-
International Chemical Identifier key (InChIKey)	JBVNWTXRFKZNBQ-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C19H24O3/c1-2-3-4-5-6-14-9-16(11-17(20)10-14)15-7-8-18-19(12-15)22-13-21-18/h7-8,10,12,16H,2-6,9,11,13H2,1H3
2D structure diagram/image available?	Yes

General status

Veterinary substance type	-
Other bioactivity & uses	Synergist
Substance groups	Synergest
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Hinders metabolic resistance by inhibiting detoxification enzymes
Molecular targets	-
CAS RN	119-89-1
EC number	-
CIPAC number	-
US EPA chemical code	-
PubChem CID	8410
Therapeutic Class	-
ATCvet Code	-
Controlled Drug?	-
Regulation 37/2010 MRL Classification	-
Molecular mass	300.4
PIN (Preferred Identification Name)	rac-(5R)-5-(2H-1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-en-1-one
IUPAC name	(5RS)-5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-en-1-one
CAS name	5-(1,3-benzodioxol-5-yl)-3-hexyl-2-cyclohexen-1-one
Other status information	-
Relevant Environmental Water Quality Standards	-
Physical state	-
Related substances & organisms	piperonyl butoxide piperonyl sulfoxide

Formulations

Property	Product	Manufacturer	Authorisation Route	Legal Class (GB/UK)
Example products (past and present) 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)		-	-	-
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		-	-	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	-	-	-
	Log P	-	-	-
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		-	-	-
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
Maximum UV-vis absorption L mol⁻¹ cm⁻¹		-	-	-
Surface tension (mN m⁻¹)		-	-	-
Refractive Index		-	-	-
Environmental release		-

Degradation

Property		Value	Source; quality score; and other information	Interpretation
Soil degradation (days) (aerobic)	DT₅₀ (typical)	-	-	-
	DT₅₀ (lab at 20 °C)	-	-	-
	DT₅₀ (field)	-	-	-
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	Note	-
Manure DT₅₀ (days)		-	-	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	-	-	-
	Note	-
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		-	-	-
Sediment phase only DT₅₀ (days)		-	-	-
Air degradation		As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	-	-
	Koc (mL g⁻¹)	-
	Notes and range	-
Freundlich	Kf (mL g⁻¹)	-	-	-
	Kfoc (mL g⁻¹)	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	-	-	-
	CT₅₀ (days)	-		-

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		-	-	-
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)		-	-	-
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)	-	-	-
	Chronic	-	-	-
	Notes	-
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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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	-	-	-
Marine bivalves		-	-	-

HUMAN HEALTH AND PROTECTION

General

Property		Value	Source; quality score; and other information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		-	-	-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		-	-	-
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
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	-
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 No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant No data found No data found No data found Respiratory tract irritant Skin irritant Skin sensitiser No data found No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		No information available

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	-
WHO Classification	Not listed (Not listed)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	piperonyl cyclonene
French	pipéronyl cyclonène
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	25/10/2024
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