1,3-dichloropropene (Ref: D D92)

1,3-dichloropropene (Ref: D D92)	Last updated: 24/10/2024
(Also known as: alpha-chloroallyl chloride; gamma-chloroallyl chloride; DCP; dichloro-1,3-propene; 1,3-D; dichloropropene)

SUMMARY

1,3-dichloropropene is a halogenated hydrocarbon used as a soil fumigant. It is highly soluble in water and many organic solvents. It is highly volatile. It is not persistent in soil or aquatic systems under normal conditions. It is moderately toxic to mammals, a recognised irritant and is unlikely to bioaccumulate. It is moderately toxic to birds, honeybees, earthworms and most aquatic organisms.

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: Drainflow: Mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High	Human health High alert: Genotoxic; Reproduction/development effects

GENERAL INFORMATION

Description

A soil nematicide used pre-planting as a fumigant to control soil-borne pests and for suppressing weed seed germination

Example pests controlled

Most species of cyst and free-living nematodes; Corky ringspot (Tobacco rattle virus)

Example applications

Vegetables including peppers, zucchini, aubergine; Fruit including melon, tomato; Forage crops including grasses and legumes; Fibre crops; Nursery crops

Efficacy & activity

Availability status

Current

Introduction & key dates

1956, introduction

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Spain/France

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

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

Australia, Morocco

Chemical structure

Isomerism

Isomeric - a mixture of the geometric cis- and trans-isomers

Chemical formula

C₃H₄Cl₂

Canonical SMILES

C=CC(Cl)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

UOORRWUZONOOLO-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+

2D structure diagram/image available?

Yes

General status

Pesticide type

Nematicide, Insecticide, Other substance

Other bioactivity & uses

Bactericide

Substance groups

Halogenated hydrocarbon insecticide; Halogenated hydrocarbon nematicide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - 1,2-dichloropropane 0.1 g kg⁻¹

Substance origin

Synthetic

Mode of action

Soil fumigant that penetrates into the nematodes via mouth and cuticle

CAS RN

542-75-6

Alternative/old CAS RN

Cis-Isomer: 010061-01-5; Trans-isomer: 010061-02-6

EC number

208-826-5

CIPAC number

675

US EPA chemical code

029001

PubChem CID

24726

CLP index number

602-030-00-5

Molecular mass

110.97

PIN (Preferred Identification Name)

(EZ)-1,3-dichloropropene

IUPAC name

(EZ)-1,3-dichloropropene

CAS name

1,3-dichlor-1-propene

Other status information

Severe water pollutant; Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

Colourless to pale straw-coloured, volatile liquid

Formulations

Property

Value

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

Dow AgroSciences

Example products using this active

Telone II
Telone EC Drip
Telone C-17
Dorlone EC
Condor

Formulation and application details

Used as a fumigant. May also be applied as a liquid via drip irrigation systems or soil injection. Up to 280 kg/ha are applied.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2450 / 2520

Cis / Trans Isomer

High / High

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

250000

Xylene

250000

Methanol

250000

Acetone

250000

Ethyl acetate

Melting point (°C)

-85 / <-25

Cis / Trans Isomer

Boiling point (°C)

103.8 / 114.5

Cis / Trans Isomer

Degradation point (°C)

Flashpoint (°C)

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

6.61 X 10⁰¹ / 1.26 X 10⁰²

Calculated

Log P

1.82 / 2.1

Cis / Trans Isomer

Low / Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.22

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.76 X 10⁰⁶ / 2.98 X 10⁰⁶

Cis / Trans Isomer

Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable / Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

170 / 101

Cis / Trans Isomer

Volatile / Volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

CIS: Neutral solution 201.5nm = 4741
Acidic solution 202.7nm = 4409
Basic solution 209.2nm = 2668 TRANS: Neutral solution 201nm = 7220
Acidic solution 204nm = 8520
Basic solution 267nm = 51.1

Surface tension (mN m⁻¹)

69.6 / 61.0

Cis / Trans Isomer

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

10.3

Non-persistent

DT₅₀ (lab at 20 °C)

10.3

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

38.0

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

16.0

Representative worse case

Note

EU 2017 dossier lab studies DT₅₀ range 9.0-14.0 days, DT₉₀ range 30.1-53.1 days, Soils=4; EU 2009 dossier Lab studies DT₅₀ range 8.8-13.5 days, DT₉₀ range 29.1-51.4 days; Other data: Literature lab studies DT₅₀ range typically 6-17 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

650

Stable

Note

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

Value

Non-persistent

Note

DT₅₀ 4.5 days at pH 4, 3 days at pH 9

Water-sediment DT₅₀ (days)

4.9

Fast

Water phase only DT₅₀ (days)

2.6

Moderately fast

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)

0.85

Mobile

K_oc (mL g⁻¹)

46.7

Notes and range

EU 2017 dossier K_d range 0.50-1.55 mL g⁻¹, K_oc range 31.4-73.6

Freundlich

K_f (mL g⁻¹)

0.54

Mobile

K_foc (mL g⁻¹)

33.7

¹/_n

1.00

Notes and range

EU 2017 dossier K_f range 0.32-0.91, K_foc range 21.6-83.0 mL g⁻¹, ¹/_n range 0.92-1.05, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.50

Calculated

Transition state

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

Value

5.96 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

Experimentally measured

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

4.6

Low potential

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

3-chloroallyl alcohol

Major fraction

0.134

3-chloroacrylic acid

Major fraction

0.373

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

3-chloroacrylic acid

Relevant

0.01

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

150

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1264 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

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

55.6

Eisenia foetida

Moderate

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

770

Eisenia foetida

Low

Soil micro-organisms

Nitrogen mineralisation: Chronic effect
Carbon mineralisation: Chronic effect

Dose: 0.77 g product Telone II/kg soil 90 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

78.0

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

6.6

Moderate

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

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)

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) as % Mortality at dose 328 kg ha⁻¹

Hypoaspis aculeifer Adult

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)

2.78

Oncorhynchus mykiss

Moderate

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

0.032

Pimephales promelas

Moderate

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

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

3.58

Daphnia magna

Moderate

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

0.071

Daphnia magna

Moderate

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

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.79

Americamysis bahia

Moderate

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

1.08

Chironomus riparius 2 day

Moderate

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)

14.6

Lemna gibba

Low

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

6.4

Pseudokirchneriella subcapitata

Moderate

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

0.6

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

150

Rat

Moderate

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

333

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

2.7

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.0125

Rat SF=100

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.2

Dog SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.1

Rat SF=100

Dermal penetration studies (%)

100

default probable dermal absorption

Dangerous Substances Directive 76/464

Exposure Routes

Public

Low risk via air, water or food due to usage pattern
Source: WHO

Occupational

Potentially via inhalation and skin absorption
Personal protection clothing and equipment must be worn when re-entering treated areas
Source: WHO/A5

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Non-statutory WHO drinking water guideline 0.02 mg l⁻¹

UK EA QS database 2018

Drinking Water MAC (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

Eye irritant

Phototoxicant

General human health issues

Highly toxic
Some evidence substance has mutagenic potential
Classified as possible carcinogen by IARC & US DHHS; US NTP - suspected carcinogen
Possible urinary, liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Corrosive
Not explosive or oxidising
Flammable liquid
IMDG Transport Hazard Class 3

CLP classification 2013

Handling: H226
Health: H301, H304, H311, H315, H317, H319, H332, H335
Environment: H400

WHO Classification

Not classified: Fumigant (Not classified: Fumigant)

UN Number

UN1993

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

1,3-dichloropropene

French

1,3-dichloropropene

German

1,3-Dichlorpropen

Danish

1,3-dichloropropen

Italian

1,3-dicloropropene

Spanish

1,3-dicloropropene

Greek

Polish

1,3-dichloropropen

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/10/2024
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