(Also known as: (+)-pulegone; d-pulegone; (R)-(+)-enantiomer)
SUMMARY
Hazard alerts
The following Pesticide Hazard Tricolour (PHT) 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. The alerts for Highly Hazardous Pesticides (HHPs) are based on applying the FAO/WHO (Type 1) and the PAN (Type II) criteria to PPDB data. Further details on the HHP indicators are given in the tables below. Neither the PHT nor the HHP hazard alerts take account of usage patterns or exposure, thus they do not represent risk.
PHT: Environmental fate
PHT: Ecotoxicity
PHT: Human health
Highly Hazardous Pesticide
Ecotoxicity High alert: Birds acute ecotoxicity: High; Bees acute unknown ecotoxicity: High
Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Possible Carcinogen; Reproduction/development effects
Warning: Significant data are missing
GENERAL INFORMATION
Description
A botanical substance, common in some plant essential oils, that exhibits bioactivity
Example pests controlled
Fleas; General insects including mites, whiteflies, aphids, mosquitoes, weevils, ants; Various fungal pathogen and microorganisms
Example applications
Stored grains; Domestic households and gardens
Efficacy & activity
-
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
GB LERAP status
No UK approval for use as a pest control agent
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
-
Chemical structure
Isomerism
Pulegone exhibits optical isomerism due to a single chiral centre at the carbon bearing the methyl group (position 5). This results in two enantiomers: the naturally predominant (R)-(+)-pulegone and the less common (S)-(-)-pulegone. No geometrical (E/Z) isomerism occurs at the C=C bond because the two substituents on the terminal carbon are identical methyl groups. Other potential isomers, such as isopulegone, are constitutional (structural) isomers rather than stereoisomers of pulegone itself.
Repellent; Insecticide; Fungicide; Antimicrobial; Other substance
Other bioactivity & uses
Flavouring; Fragrance
Substance groups
Plant-derived substance; Monoterpene ketone
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Natural
Mode of action
The mode of action is not fully clear and is multifaceted. As an insecticide, it has neurotoxic effects, acting as positive allosteric modulators of insect GABA receptors, potentially disrupting neurotransmission and leading to hyperexcitation, paralysis or death. It can also inhibit key insect enzymes leading to oxidative stress, accumulation of damaging reactive species, and enhanced vulnerability to the compound itself or mixtures. It acts as an antifeedant, disrupting probing/feeding behaviour and may affect oviposition or embryonic development in eggs. It’s strong odour contributes to its insect repellency. As a fungicide in inhibits mycelial growth, respiration and thought to deactivate fungi by disrupting the structure and function of fungal cell membranes and organelles.
Example manufacturers & suppliers of products using this active now or historically
Not currently produced specifically for pest management
Example products using this active
-
Formulation and application details
-
Commercial production
Pulegone is commercially produced primarily through natural extraction from essential oils, especially pennyroyal mint (Mentha pulegium), of the volatile oil obtained by steam distillation of the leaves and flowering tops of the plant, cultivated mainly for this purpose in regions supporting mint production. Synthetic production is possible but not common due to sufficient natural supply and toxicity-related market constraints. Small quantities are also obtainable via in vitro shoot cultures of peppermint (Mentha piperita) in fermenters but these are not significant for bulk commercial output.
Impact on climate of production and use
Data for specific plant oils is scarce. However, from publicly available data the carbon footprint of plant oils has been estimated at between 1.0 and 4.0 kg CO₂e per kg of oil. This depends on the plant oil content, agricultural practices and processing methods used.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C at pH 7 (mg l⁻¹)
173.7
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
at 25 °C
Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Ethanol
-
Miscible
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Chloroform
-
Miscible
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Carbon tetrachloride
-
Melting point (°C)
-
-
-
Boiling point (°C)
224
F3 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 ) 3 = Unverified data of known source
-
Degradation point (°C)
-
-
-
Flashpoint (°C)
88
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
1.58 X 1003
Calculated
-
Log P
3.2
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
High
Fat solubility of residues
Solubility
-
-
-
Data type
-
-
-
Density (g ml⁻¹)
0.93
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
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
Peaks at 253 nm (in methanol) with minor absorbance between 290-700 nm
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
Surface tension (mN m⁻¹)
-
-
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
Readily biodegradable
Soil degradation (days) (aerobic)
DT₅₀ (typical)
-
-
-
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
-
Dissipation rate RL₅₀ (days) on plant matrix
Value
-
-
-
Note
-
Dissipation rate RL₅₀ (days) 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
-
-
-
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
-
-
-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated
-
-
Note
-
Potential for particle bound transport index
-
-
-
Potential for loss via drain flow
-
-
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
50.0
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Rat
Moderate
Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)
> 80
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Rat
Moderate
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
> 18.75
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Mice NOAEL
Moderate
Birds - Acute LD₅₀ (mg kg⁻¹)
< 1.0
F3 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 ) 3 = Unverified data of known source
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)
0.1
F3 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 ) 3 = Unverified data of known source
Apis mellifera
High
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)
-
-
-
Beneficial insects (Butterflies)
Contact
-
-
-
Notes
-
Oral
-
-
-
Notes
-
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
18.56
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Unknown species
Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
-
-
-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative
No data found
Reproduction / development effects
Acetyl cholinesterase inhibitor
Neurotoxicant
?Possibly, status not identified
No data found
No data found
Respiratory tract irritant
Skin irritant
Skin sensitiser
No data found
✓Yes, known to cause a problem
XNo, known not to cause a problem
Eye irritant
Phototoxicant
✓Yes, known to cause a problem
No data found
General human health issues
Hepatotoxic High exposure may increase liver/kidney weights, hyaline glomerulopathy, bile duct hyperplasia, and hepatocyte hypertrophy IARC Group 2B, possibly carcinogenic to humans
Handling issues
Property
Value and interpretation
General
Combustible
CLP classification 2013
-
WHO Classification
-
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
Sensitive to light - store in a dark place; Stable under recommended storage condition
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
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Ecotoxicity
Human health
Warning:
