Dieldrin (Ref: ENT 16225 )

Dieldrin (Ref: ENT 16225 )	Last updated: 14/11/2024
(Also known as: dieldrex; dieldrite; SD 3417; dieldrine)

SUMMARY

Dieldrin is an obsolete insecticide. It has a low aqueous solubility and is volatile. Based on its chemical properties, it is not expected to leach to groundwater. Its data suggests it is very persistent in soils and is non-mobile. It is highly toxic to mammals with a high potential for bioaccumulation. It is a neurotoxin and probably a mutagen. Dieldrin has a moderate toxicity to birds, aquatic invertebrates and algae but considered to be more toxic to fish and 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 High alert: Very persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High; Bees acute unknown ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Genotoxic; Endocrine disrupter; Reproduction/development effects; Neurotoxicant

GENERAL INFORMATION

Description

An obsolete cyclodiene insecticide. Can also be a pesticide transformation product

Example pests controlled

Termites; Locusts; Wood eating insects; Fabric eating insects

Example applications

Wood; Fabrics; Public health situations

Efficacy & activity

Availability status

Considered obsolete but may be available in some countries; Banned in many countries

Introduction & key dates

1949, first reported

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 pesticide

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

Yes

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

Dieldrin is a stereoisomer of endrin

Chemical formula

C₁₂H₈Cl₆O

Canonical SMILES

C1C2C3C(C1C4C2O4)C5(C(=C(C3(C5(Cl)Cl)Cl)Cl)Cl)Cl

Isomeric SMILES

C1[C@@H]2[C@H]3[C@@H]([C@H]1[C@H]4[C@@H]2O4)[C@]5(C(=C([C@@]3(C5(Cl)Cl)Cl)Cl)Cl)Cl

International Chemical Identifier key (InChIKey)

DFBKLUNHFCTMDC-PICURKEMSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H8Cl6O/c13-8-9(14)11(16)5-3-1-2(6-7(3)19-6)4(5)10(8,15)12(11,17)18/h2-7H,1H2/t2-,3+,4+,5-,6-,7+,10+,11-

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
dieldrin	Unstated isomer

General status

Pesticide type

Insecticide, Metabolite

Metabolite Type

Soil

Substance groups

Cyclodiene insecticide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Central nervous system stimulant. GABA-gated chloride channel antagonist. Contact and stomach action

CAS RN

60-57-1

EC number

200-484-5

CIPAC number

US EPA chemical code

045001

PubChem CID

969491

CLP index number

602-049-00-9

Molecular mass

380.91

PIN (Preferred Identification Name)

(1aR,2R,2aS,3S,6R,6aR,7S,7aS)-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth[2,3-b]oxirene

IUPAC name

(1R,4S,4aS,5R,6R,7S,8S,8aR)-1,2,3,4,10,10-hexachloro-1,4,4a,5,6,7,8,8a-octahydro-6,7-epoxy-1,4:5,8-dimethanonaphthalene

CAS name

(1aR,2R,2aS,3S,6R,6aR,7S,7aS)-rel-3,4,5,6,9,9-hexachloro-1a,2,2a,3,6,6a,7,7a-octahydro-2,7:3,6-dimethanonaphth(2,3-b)oxirene

Other status information

WFD priority substance; POP; LRTAP Annex I; PAN Dirty Dozen; OSPAR soc; Marine Pollutant; Rotterdam Convention (Class O) - subject to PIC regulations

Relevant Environmental Water Quality Standards

EU Directive 2008/105/EC EQS sum of all cyclodiene pesticides in: Inland surface waters as annual average: 0.01 µg l⁻¹; Other surface waters; 0.005 µg l⁻¹

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Many recorded cases, Agriotes lineatus, Agriotes obscurus, Anopheles sacharovi, Blattella germanica, Chironomus zealandicus, Epitrix cucumeris, Plusia gamma

Physical state

White to light brown crystals

Related substances & organisms

endrin

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

aldrin

Soil

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Shell Chemical Co.
Hyman

Example products using this active

Octalox
Panoram D-31
Alvit
Dieldrex

Formulation and application details

Usually supplied in a variety of formulations including wettable powders, granules and emulsifiable concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.14

Low

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

Melting point (°C)

177

Boiling point (°C)

385

Degradation point (°C)

Flashpoint (°C)

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

5.01 X 10⁰³

Calculated

Log P

3.7

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.75

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.024

Low volatility

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

6.50 X 10^-02

Non-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)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1400

Very persistent

DT₅₀ (lab at 20 °C)

2000

Very persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data, PIC DGD DT₅₀ 5 years; Other sources: DT₅₀ 800-900 days (R3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

6.8

Note

Published literature RL₅₀ range 6.5-7.0 days, 2 field crops, various matrices, n=2

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.0

Note

Published literature RL₅₀ range 2.0-10.0 days, 6 field crops, various matrices, n=8

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

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

12000

Notes and range

Freundlich

K_f (mL g⁻¹)

1563

K_foc (mL g⁻¹)

¹/_n

0.95

Notes and range

Mean of 3 soils. Organic K_f=4246; Sandy loam K_f=338; Sand K_f=106

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.26

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

35000

Whole body (Literature values Log BCF range 1.4-4.1 ())

High potential

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

0.5

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

Birds - Acute LD₅₀ (mg kg⁻¹)

153

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

100

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)

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)

0.32

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)

0.029

Trigona spinipes

High

Mode of exposure

Contact

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

0.0036

Megachile rotundata

High

Mode of exposure

Contact

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)

0.0012

Oncorhynchus mykiss

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

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

0.00225

Danio rerio Embryo

High

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

0.25

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)

Chironomus dilutus 10 day LC₅₀

Moderate

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

0.1

Chlorella pyrenoidosa

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀, development (mg l⁻¹)

> 0.015

Crassostrea gigas Embryo

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)

Rat

High

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

Rat

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

List II

Exposure Routes

Public

Occupational

Can be absorbed into the body via dermal and inhalation routes

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.03

PIC DGD - WHO recommendation max limit 0.03 µg l⁻¹

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Extremely hazardous
Exposure can lead to convulsions
IARC Group 3 carcinogen - not classifiable; CLP data - suspected carcinogen; US EPA - probable human carcinogen
Endocrine issues - Competitive binding to androgen receptors, estrogenic effect

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H301, H310, H351, H372
Environment: H400, H410

WHO Classification

Ib (Highly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

dieldrin

French

dieldrine

German

Dieldrin

Danish

dieldrin

Italian

dieldrin

Spanish

dieldrin

Greek

dieldrin

Polish

dieldryna

Swedish

Hungarian

Dutch

dieldrine

Norwegian

Record last updated:	14/11/2024
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