Endrin

Endrin	Last updated: 18/01/2021
(Also known as: nendrin; OMS 197; aldrin epoxide; Experimental Insecticide 269)

SUMMARY

Endrin is an obsolete, multi-use organochlorine insecticide that is not approved for use in the EU. It has a low aqueous solubility and is non-volatile. Based on its chemical properties it is not expected to leach to groundwater. Endrin tends to be persistent in soil systems. It is highly toxic to mammals and is a neurotoxin. It is also highly toxic to birds, honeybees and most aquatic organisms but slightly less so to earthworms.

GENERAL INFORMATION

Description

A multi-use but now obsolete pesticide used to control insects, rodents, and birds.

Example pests controlled

Aphids; Lygus bugs; Grasshoppers; Small mammals including mice, voles

Example applications

Field crops; Cotton; Grains; Rice; Sugarcane

Efficacy & activity

Availability status

Obsolete, Banned

Introduction & key dates

1950s

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

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

Also used in

Chemical structure

Isomerism

Isomeric

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-GKRDHZSOSA-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-/m0/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
endrin	Unstated isomer

General status

Pesticide type

Insecticide, Avicide, Rodenticide

Substance group

Organochlorine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Broad-spectrum, with contact and stomach action. Is a chloride channel-blocking agent.

CAS RN

72-20-8

EC number

200-775-7

CIPAC number

US EPA chemical code

041601

PubChem CID

12358480

Molecular mass

380.91

PIN (Preferred Identification Name)

(1aR,2R,2aR,3R,6S,6aS,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

1,2,3,4,10,10-hexachloro-6,7-epoxy-1,4,4a,5,6,7,8,8a-octahydro-exo-1,4-exo-5,8-dimethanonaphthalene

CAS name

(1aR,2R,2aR,3R,6S,6aS,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 - regulated by Stockholm Convention; LRTAP Annex I; PAN Dirty Dozen; OSPAR soc; Severe Marine Pollutant

Relevant Environmental Water Quality Standards

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

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not known

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Many recorded cases, Aphis gossypii, Culex pipiens pipiens, Empoasca biguttula, Leptocorisa oratorius, Spodoptera littoralis, many others

Physical state

White crystals

Formulations

Property

Value

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

Endrex
Mendrin
Nendrin
Hexadrin

Example products using this active

Shell Chemical Company
Velsicol

Formulation and application details

Available in a variety of formulations including wettable powders and emulsifiable concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.24

Low

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

Melting point (°C)

200

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

1.58 X 10⁰³

Calculated

Log P

3.2

High

Bulk density (g ml⁻¹)

1.84

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

2.0 X 10^-07

Low volatility

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

1.48 X 10^-01

Moderately volatile

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)

4300

Very persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Other sources: DT₅₀ up to 12 years (R3); FAO state DT₅₀ 4-14 days

Dissipation rate RL₅₀ on plant matrix

Value

3.3

Note

Birdsfoot trefoil leaves, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

4.0

Note

Published literature RL₅₀ range 1.0-7.0 days, 2 field crops, various matrices, n=2

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)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

10000

Notes and range

Other sources: 31623 mL g⁻¹ (R3)

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

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

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

endrin aldehyde
Note: Persistent

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

3970

(whole body Literature values log BCF range 2.2-3.4 ())

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 7.5

Rat

High

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)

5.6

Anas platyrhynchos

High

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.00073

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.00012

Cyprinodon variegatus

High

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

0.0042

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

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

Honeybees (Apis spp.)

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

> 0.46

High

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)

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 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

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

> 66

Lumbricus terrestris

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

> 7.5

Rat

High

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

5.0

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

0.0002

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 I; List II

Exposure Routes

Public

Occupational

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Non-statutory WHO drinking water guideline 0.0006 mg l⁻¹

UK EA QS database 2018

Drinking Water MAC (μg l⁻¹)

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

Highly toxic
Endocrine issues - Competitive binding to androgen receptors

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H300, H311
Environment: H400, H410

EC Risk Classification

T+ - Very toxic: R28
T - Toxic: R24
N - Dangerous for the environment: R50, R53

EC Safety Classification

S1/2, S22, S36/37, S45, S60, S61

WHO Classification

O (Obsolete substance)

UN Number

2761

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

endrin

French

endrine

German

Endrin

Danish

endrin

Italian

endrin

Spanish

endrin

Greek

endrin

Polish

endryna

Swedish

Hungarian

Dutch

endrine

Record last updated:	18/01/2021
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