Diallyl disulfide

Diallyl disulfide	Last updated: 25/05/2024
(Also known as: garlicin; DAS2)

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 Moderate alert: Drainflow: Moderately mobile	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate Warning: Significant data are missing	Human health Moderate alert: Mammals acute toxicity: Moderate

GENERAL INFORMATION

Description

A major componrnt of garlic extract shown to have insecticidal, fungicidal and other pesticide activity

Example pests controlled

Larval and adult mosquitoes; Other crawling and flying insects; White rot (Sclerotium cepivorum)

Example applications

Onions; Leeks; Ornamentals

Efficacy & activity

Appearance and life cycle

Availability status

Not commercially available as a pesticide

Introduction & key dates

1944, discovered

Taxonomic classification

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

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

Known to be also used in the following countries

USA

Chemical structure

Isomerism

None

Chemical formula

C₆H₁₀S₂

Canonical SMILES

C=CCSSCC=C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PFRGXCVKLLPLIP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
diallyl disulfide	-

General status

Biopesticide type

Insecticide, Fungicide, Other substance

Other bioactivity & uses

Antimicrobial

Substance groups

Plant-derived substance

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Show to interfere with an insects’ sensory receptors, leading to disorientation and death at all life stages

Substance source

Diallyl disulfide is produced by the decomposition of allicin which is emitted duting the decomposition of Alliaceae plants, especially garlic. It is the main component of the distilled garlic oil.

Substance production

Industrially, diallyl disulfide is produced from sodium disulfide and allyl bromide or allyl chloride at temperatures of 40–60 °C in an inert gas atmosphere

Uses

Crop protection; General pest management

Target pests

Larval and adult mosquitoes; Other crawling and flying insects; White rot (Sclerotium cepivorum)

Target host

Onions; Leeks; Ornamentals

Farming system suitability

CAS RN

2179-57-9

EC number

218-548-6

CIPAC number

US EPA chemical code

129087

PubChem CID

16590

Molecular mass

146.3

PIN (Preferred Identification Name)

3-[(prop-2-en-1-yl)disulfanyl]prop-1-ene

IUPAC name

3-[(prop-2-en-1-yl)disulfanyl]prop-1-ene

CAS name

Other status information

FEMA=2028

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

Yellow coloured liquid with strong garlic odour.

Related substances & organisms

garlic oil

Formulations

Property

Product

Manufacturer

Example products

Alli-Up

Platte Chemical Co

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

71.1

Moderate

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

Melting point (°C)

Boiling point (°C)

176

Degradation point (°C)

Flashpoint (°C)

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

3.16 X 10⁰³

Calculated

Log P

3.5

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.03

Dissociation constant pKa) at 25 °C

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)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.0

Non-persistent

DT₅₀ (lab at 20 °C)

1.0

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature: Rapidly breaks down in soil

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

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)

Moderately mobile

K_oc (mL g⁻¹)

184

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

346

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)

> 1000

Unknown species

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)

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

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)

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)

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)

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

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

346

Rat

Moderate

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

1967

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

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

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

Eye irritant

Phototoxicant

No data found

General human health issues

Possible irritant
May have health benefits - protectant against various cancers and cardiovascular disease
May cause respiratory problerms

Handling issues

Property

Value and interpretation

General

Highly flammable
Not explosive or oxidising
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H226, H301, H315, H319

WHO Classification

Not listed (Not listed)

UN Number

UN2810

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

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Record last updated:	25/05/2024
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