D-carvone

D-carvone	Last updated: 24/05/2024
(Also known as: p-mentha-6,8-dien-2-one; S-carvone; spearment oil component; (+)-carvone)

GENERAL INFORMATION

Description

A fungicide and plant growth regulator often used as a potato sprouting inhibitor

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

D-carvone is the S-isomer of chiral carvone

Chemical formula

C₁₀H₁₄O

Canonical SMILES

CC1=CCC(CC1=O)C(=C)C

Isomeric SMILES

CC1=CC[C@H](CC1=O)C(=C)C

International Chemical Identifier key (InChIKey)

ULDHMXUKGWMISQ-SECBINFHSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
D-carvone	-

General status

Veterinary substance type

Metabolite Type

Soil, Groundwater

Substance groups

Plant-derived substance

Minimum active substance purity

>930g kg⁻¹

Known relevant impurities

Substance origin

Natural

Mode of action

Inhibits cell growth

Molecular targets

CAS RN

2244-16-8

EC number

218-827-9

CIPAC number

602

US EPA chemical code

PubChem CID

Therapeutic Class

ATCvet Code

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

150.21

PIN (Preferred Identification Name)

IUPAC name

(S)-5-isopropenyl-2-methylcyclohex-2-en-1-one

CAS name

(S)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-one

Other status information

Relevant Environmental Water Quality Standards

Physical state

Colourless to pale yellow liquid

Related substances & organisms

orange oil

carvone

L-carvone

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)

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

250000

Xylene

250000

Heptane

25000

Ethyl acetate

250000

Acetone

Melting point (°C)

-43

Freezing point

Boiling point (°C)

233

as Carvone

Degradation point (°C)

Flashpoint (°C)

as Carvone

Octanol-water partition coefficient at pH 7, 20 °C

2.51 X 10⁰²

Calculated

Log P

2.4

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

0.957

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

1900

as Carvone

Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.6

as Carvone

Moderately volatile

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)

57.2

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)

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

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (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)

Low risk

Based on LogP < 3

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)

> 2000

Rat as Carvone

Low

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)

> 1000

Expert judgement

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)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

100

Expert judgement

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

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 20.3

Oncorhynchus mykiss

Moderate

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)

> 9.59

Daphnia magna

Moderate

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)

4.58

Unknown species

Moderate

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

Intermediate (class II)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat as Carvone

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

4000

Rat as Carvone

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.66

Rat 4 hr as Carvone

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.025

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

None allocated

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.025

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

PPE/PPC recommended

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

May cause gastrointestinal tract irritation with nausea, vomiting and diarrhoea
Skin sensitiser
Possible kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Flammable

CLP classification 2013

Health: H304, H317, H315

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

D-carvone

French

d-carvone

German

d-Carvon

Danish

d-carvon

Italian

d-carvone

Spanish

d-carvone

Greek

Polish

d-karwon

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/05/2024
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