DDE (Ref: HSDB 1625)

DDE (Ref: HSDB 1625)	Last updated: 26/08/2024
(Also known as: dichlorodiphenyldichloroethylene; DDT dehydrochloride; p,p'-DDE)

GENERAL INFORMATION

Description

Chemical transformation product formed by the dehydrohalogenation of DDT. Has insecticidal properties but no significant commercial applications.

Availability status

Not applicable

Introduction & key dates

Not applicable

Examples of veterinary uses

Examples of species treated

Approval status

VMR 2013/2033 approval status (GB/UK)

EU Regulatory approval status

Chemical structure

Isomerism

Consists of three isomeric forms p,p'-DDE, o,p'-DDE and o,o'-DDE. p,p'-DDE is the dominant isomer.

Chemical formula

C₁₄H₈Cl₄

Canonical SMILES

C1=CC(=CC=C1C(=C(Cl)Cl)C2=CC=C(C=C2)Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UCNVFOCBFJOQAL-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H8Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
DDE	-

General status

Veterinary substance type

Metabolite Type

Soil, Groundwater

Substance groups

Organochloride substance

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Central nervous system stimulant. GABA-gated chloride channel antagonist. A weak androgen receptor antagonist.

Molecular targets

CAS RN

72-55-9

EC number

200-784-6

CIPAC number

292

US EPA chemical code

PubChem CID

3035

Therapeutic Class

ATCvet Code

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

318.02

PIN (Preferred Identification Name)

IUPAC name

1,1-bis-(4-chlorophenyl)-2,2-dichloroethene

CAS name

1,1-dichloro-2,2-bis(p-chlorophenyl)-ethylene

Other status information

OSPAR soc, Banned; Hazardous air pollutant

Relevant Environmental Water Quality Standards

Physical state

White crystalline solid

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

O,O'-DDT

Soil

O,O'-DDT

Groundwater

Relevancy unknown

O,P'-DDT

Soil

O,P'-DDT

Groundwater

Relevancy unknown

lindane

Soil

DDT

Soil

DDT

Groundwater

Relevancy unknown

P,P'-DDT

Soil

P,P'-DDT

Groundwater

Relevancy unknown

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)

0.12

Low

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

Melting point (°C)

Boiling point (°C)

336

Degradation point (°C)

Flashpoint (°C)

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

3.24 X 10⁰⁶

Calculated

Log P

6.51

High

Fat solubility of residues

Solubility

Likely to be soluble

Data type

Based on chemical group

Density (g ml⁻¹)

1.402

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

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

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

5000

Very persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

5000

Very persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Environmentally stable

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)

50000

K_oc (mL g⁻¹)

Notes and range

Log K_oc given as 4.7

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)

1800

Oncorhynchus mykiss

Threshold for concern

CT₅₀ (days)

Not available

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

1-chloro-2,2-bis(p-chlorophenyl)ethylene

DDMU

Humans; Rats

2,2-bis(bis(p-chlorophenyl)ethylene

DDNU

Humans; Rats

2,2-bis(p-chlorophenyl)acetaldehyde

DDCHO

Humans; Rats

2,2-bis(p-chlorophenyl)acetic acid

DDA

Humans; Rats

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

880

Rat

Moderate

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)

825

Colinus virginianus

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)

Lumbricus terrestris

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)

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)

== 0.032

Oncorhynchus mykiss

High

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)

0.001

Bosmina longirostris

High

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)

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)

880

Rat

Moderate

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

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 I

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

DDE is mainly excreted in the bile. Excretion is slow with a biologic half-life of about 8 yr.

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Toxic if ingested, inhaled and via skin absorption
Xenoestrogen agent
Mutagenic
Endocrine issues - Competitive binding to androgen receptors
US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

P,P'-DDE is sensitive to exposure to light
Incompatible with strong oxidising substances and strong bases
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302, H311, H315, H331, H332
Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

UN2761

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

DDE

French

German

Danish

Italian

Spanish

Greek

Polish

dichlorodifenylodichloroetylen

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	26/08/2024
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