Rotenone (Ref: ENT 133)

Rotenone (Ref: ENT 133)	Last updated: 23/02/2022
(Also known as: derris root; derris; haiari; barbasco; aker-root)

SUMMARY

A naturally occurring chemical with multiple crop protection applications. It is moderately toxic. It is not environmentally persistent degrading in soil in a few days. It is not expected to leach from soil or contaminate groundwaters. It is highly toxic to all aquatic organisms, earthworms and to honeybees.

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 Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute contact ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate

GENERAL INFORMATION

Description

Used to control a variety of insect pests including parasitic mites, fleas, ticks and mites

Availability status

Current

Introduction & key dates

circa 1935

Examples of species treated

Dogs, Cats, Fowl, Poultry

Chemical structure

Isomerism

A chiral molecule. The technical material is a misture of the cis- and trans-forms

Chemical formula

C₂₃H₂₂O₆

Canonical SMILES

CC(=C)C1CC2=C(O1)C=CC3=C2OC4COC5=CC(=C(C=C5C4C3=O)OC)OC

Isomeric SMILES

CC(=C)[C@H]1CC2=C(O1)C=CC3=C2O[C@@H]4COC5=CC(=C(C=C5[C@@H]4C3=O)OC)OC

International Chemical Identifier key (InChIKey)

JUVIOZPCNVVQFO-HBGVWJBISA-N

International Chemical Identifier (InChI)

InChI=1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
rotenone	-

General status

Veterinary substance type

Insecticide, Antiparasitic

Substance groups

Plant derived substance

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Selective, non-systemic with contact and stomach action. Mitochondrial complex I electron transport inhibitor.

Molecular targets

CAS RN

83-79-4

EC number

201-501-9

CIPAC number

US EPA chemical code

071003

PubChem CID

ATCvet Code

Therapeutic Class

Controlled Drug?

Regulation 37/2010 MRL Classification

No data

Molecular mass

394.42

PIN (Preferred Identification Name)

IUPAC name

(2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno[3,4-b]furo[2,3-h]chromen-6-one

CAS name

(2R,6aS,12aS)-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one

Other status information

Marine Pollutant; Chemical subject to PIC regulations; PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Physical state

White powder

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

None identified

No UK authorisation for use with animals

Not applicable

Formulation and application details

Usually formulated as an emulsifiable concentrate or dust

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

15.0

Low

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

Melting point (°C)

163

Boiling point (°C)

215

Degradation point (°C)

Flashpoint (°C)

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

1.45 X 10⁰⁴

Calculated

Log P

4.16

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

0.67

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

1.0

Low volatility

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

1.13 X 10^-08

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)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Best available data

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

1.3

Non-persistent

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

10000

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.00

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

Lepomis macrochirus

Low potential

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 132

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Dog

High

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2600

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)

> 150

Eisenia foetida

Moderate

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)

> 0.24

Apis mellifera

High

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

> 12

Apis mellifera

Moderate

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)

> 0.68

Bombus terrestris 72hr

High

Literature LD₅₀ values range 0.17-0.97 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

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Harmful

Parasitic wasp

Beneficial insects (Predatory mites)

Moderately harmful

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0019

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0012

Oncorhynchus mykiss 32 day LOEC

High

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.004

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.001

Daphnia magna

High

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)

0.0057

Unknown species

High

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)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 132

Rat

Moderate

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

5000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.019

Rat

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 0.20 mg kg⁻¹

Rat

Subcutaneous LD₅₀ = 20.0 mg kg⁻¹

Rabbit

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

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Moderately toxic

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9 or 6.1

CLP classification 2013

Health: H301, H315, H319, H335
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

2588 for active, products usually 2811

Waste disposal & packaging

Packaging Group II (medium danger) or III (minor danger)

TRANSLATIONS

Language

Name

English

rotenone

French

rotenone

German

Rotenon

Danish

rotenon

Italian

rotenone

Spanish

rotenona

Greek

Polish

rotenon

Swedish

rotenon

Hungarian

Dutch

rotenon

Record last updated:	23/02/2022
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