DDD (Ref: ENT 4225)

DDD (Ref: ENT 4225)	Last updated: 07/01/2021
(Also known as: dichlorodiphenyldichloroethane; tetrachlorodiphenylethane; TDE; p,p'-DDD; ME-1700)

SUMMARY

DDD is a banned and obsolete insecticide that is also a metabolite of DDT. It is practically insoluble in water and is not highly volatile. It is, like DDT, very environmentally perssitent in both soils and water. It is toxic to humans through ingestion, inhalation and via skin absorption and has been linked with cancer, is mutagenic and various negative reproduction/fertility effects. It is also an endocrine disrupter. It is toxic to most animal species but data is not abundant.

GENERAL INFORMATION

Description

A now obsolete insecticide that was formerly used to kill a wide range of insect pests especially those that carry disease. It is also a pesticide transformation product of DDT

Example pests controlled

Mosquitoes; Lice

Example applications

Vegetables; Cotton; Peanuts; Forestry; Public health situations

Efficacy & activity

Not applicable

Availability status

Obsolete, banned

Introduction & key dates

1944, first reported

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

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

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

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

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

Chemical formula

C₁₄H₁₀Cl₄

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

AHJKRLASYNVKDZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H10Cl4/c15-11-5-1-9(2-6-11)13(14(17)18)10-3-7-12(16)8-4-10/h1-8,13-14H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
DDD	-

General status

Pesticide type

Insecticide, Metabolite

Metabolite Type

Soil

Substance group

Organochlorine

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Non-systemic stomach and contact action

CAS RN

72-54-8

EC number

200-783-0

CIPAC number

199

US EPA chemical code

029101

PubChem CID

6294

Molecular mass

320.04

PIN (Preferred Identification Name)

IUPAC name

1,1-dichloro-2,2-bis(4-chlorophenyl)ethane

CAS name

1,1'-(2,2-dichloroethylidene)bis(4-chlorobenzene)

Other status information

Common environmental pollutant

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Clear to off-white coloured crystals

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

DDT

Soil

Not assessed under 91/414 or 1107/2009

P,P'-DDT

Soil

Not assessed under 91/414 or 1107/2009

O,P'-DDT

Soil

Not assessed under 91/414 or 1107/2009

O,O'-DDT

Soil

Not assessed under 91/414 or 1107/2009

Formulations

Property

Value

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

Rhothane

Example products using this active

Rohm & Haas

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.09

Low

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

Melting point (°C)

110

Boiling point (°C)

350

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.05 X 10⁰⁶

Calculated

Log P

6.02

High

Bulk density (g ml⁻¹)

1.385

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.18

at 25 °C

Low volatility

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

4.0 X 10^-06

Non-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

Not considered to be biodegradeable.

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1000

Very persistent

DT₅₀ (lab at 20 °C)

160

Persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Environmentally stable

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Stable

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

131000

Notes and range

Literature data ranges 130600 to 131800 mL g⁻¹

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

-2.46

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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

113

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)

> 4814

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.07

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 0.009

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)

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)

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)

113

Rat

Moderate

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

1200

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Percutaneous LD₅₀ > 10000 mg kg⁻¹

Rat

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

Risk from residues in food but the substance is now banned

Occupational

PPE/PPC essential

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

US drinking water standards are variable by State: Minnesota 1.0 µg l⁻¹, Florida 0.1 µg l⁻¹

Drinking Water MAC (μg l⁻¹)

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

Moderately toxic by ingestion, inhalation and skin absorption
Endocrine issues - Competitive binding to androgen receptors
Whilst DDD is linked with cancer one particular isomeric form (o,p'-DDD) has been used to treat cancer of the adrenal gland

Handling issues

Property

Value and interpretation

General

Combustible
Incompatible with alkalis, strong oxidisers

CLP classification 2013

Health: H301, H312, H351
Environment: H400, H401

EC Risk Classification

Not classified: Obsolete

EC Safety Classification

Not classified: Obsolete

WHO Classification

O (Obsolete substance)

UN Number

2761

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

DDD

French

TDE

German

TDE

Danish

TDE

Italian

TDE

Spanish

TDE

Greek

Polish

dichlorodifenylodichloroetan

Swedish

Hungarian

Dutch

TDE

Record last updated:	07/01/2021
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