Dodine (Ref: BAS 365F)

Dodine (Ref: BAS 365F)	Last updated: 13/12/2024
(Also known as: cytrex; doguadine; tsitrex; CL 7521; carpene; N-dodecylguanidine acetate (1:1))

SUMMARY

Dodine is a guanidine fungicide which is currently approved for use in both the UK and the EU. It is highly soluble in water but not most organic solvents. It tends not to be persistent in soil and is non-mobile. Based on its physico-chemical parameters, dodine is not expected to leach to groundwater. It demonstrates a moderate toxicity to mammals, birds and fish but is highly toxic to aquatic invertebrates and algae. It is less toxic to bees. Limited data is available on its toxicity to humans it is considered moderately toxic via the oral route.

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: Potential for particle bound transport: Medium	Ecotoxicity High alert: Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

An acetate salt resulting from the reaction of equimolar amounts of 1-dodecylguanidine and acetic acid used as a fungicide. Also an effective algal growth inhibitor useful in non-agricultural applications.

Example pests controlled

Scab, Leaf spot, Brown rot; Blossom rot; Fusarium wilt; Downey mildew

Example applications

Tree fruit including apple, pear, peach, cherry; Strawberries; Walnuts; Sycamore; Onions; Roses

Efficacy & activity

Availability status

Current

Introduction & key dates

1957, first reported

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2029

GB LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Spain/Germany

Date EC 1107/2009 inclusion expires

15/07/2026

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, USA, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₃₃N₃O₂

Canonical SMILES

CCCCCCCCCCCCN=C(N)N.CC(=O)O

Isomeric SMILES

International Chemical Identifier key (InChIKey)

YIKWKLYQRFRGPM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H29N3.C2H4O2/c1-2-3-4-5-6-7-8-9-10-11-12-16-13(14)15;1-2(3)4/h2-12H2,1H3,(H4,14,15,16);1H3,(H,3,4)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Guanidine fungicide; Aliphatic nitrogen fungicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protectant and eradicant action. Cell membrane disruption.

CAS RN

2439-10-3

EC number

219-459-5

CIPAC number

101

US EPA chemical code

044301

PubChem CID

17110

CLP index number

607-076-00-X

Molecular mass

287.44

PIN (Preferred Identification Name)

N-dodecylguanidinium acetate

IUPAC name

1-dodecylguanidinium acetate

CAS name

dodecylguanidine monoacetate

Other status information

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)

U12

Examples of recorded resistance

Physical state

Colourless to yellow fine waxy powder. Product may be liquid.

Formulations

Property

Value

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

Clayton
Greencrop
Hermoo

Example products using this active

Dodifun 400SC
Radspor L
Syllit 400SC

Formulation and application details

Often supplied as an emulsifiable concentrate or wettable powder

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

930

High

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

n-Heptane

Xylene

Acetone

57000

Ethanol

Melting point (°C)

132.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200.5

Flashpoint (°C)

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

1.78 X 10⁰¹

Calculated

Log P

1.25

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

5.49 X 10^-03

Low volatility

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

1.69 X 10^-06

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

200nm= 2600, 290nm = 1.5

Surface tension (mN m⁻¹)

50.6

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

4.7

Non-persistent

DT₅₀ (lab at 20 °C)

4.8

Non-persistent

DT₅₀ (field)

13.3

Non-persistent

DT₉₀ (lab at 20 °C)

17.8

Non-persistent

DT₉₀ (field)

60.1

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 2.6-8.2 days, DT₉₀ range 10.5-27.2 days; field studies DT₅₀ range 6.7-18.6; DT₉₀ range 22.1-108.3 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.0

Note

Published literature RL₅₀ range 3.6-4.5 days, apple, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

12.6

Moderately fast

Note

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

Value

914

Very persistent

Note

pH sensitive: DT₅₀ 576 days at pH 5, 1198 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

0.33

Fast

Water phase only DT₅₀ (days)

0.18

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)

10472

Non-mobile

K_oc (mL g⁻¹)

4236500

Notes and range

EU dossier K_d range 2202-18019 mL g⁻¹, K_oc range 5.51E05 - 1.29E07 mL g⁻¹, Soils=4

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

-2.95

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

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

3.9

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

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

dodecyl guanidine carboxylic acid

Animal

octylguanidine carboxylic acid

Animal

hexylguanidine carboxylic acid

Animal

hydroxydodecylguanidine

Animal (Urine)

0.23

guanidine

Plant

0.36

urea

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

851

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

800

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

52.61

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

857

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Unknown species Geomean

Moderate

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

547

Eisenia foetida

Moderate

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

171

Eisenia foetida

Low

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 9 kg ha⁻¹ 28 Day

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)

145

Apis mellifera

Low

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

> 200

Apis mellifera

Low

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) as Mortality LR₅₀ g ha⁻¹ 48 hr

> 1800

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

> 7512

Typhlodromus pyri

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)

0.57

Oncorhynchus mykiss

Moderate

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

0.099

Pimephales promelas 30 day

Moderate

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

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

0.018

Daphnia magna

High

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

0.0044

Daphnia magna

High

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

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

1.7

Americamysis bahia

Moderate

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

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

3.2

Chironomus riparius

Moderate

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)

0.0028

Pseudokirchneriella subcapitata

High

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

Mesocosm study data

NOEAEC mg l⁻¹

0.041

Aquatic invertebrates

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)

851

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.45

Rat (nose only aerosol)

Other Mammal toxicity endpoints

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

0.1

Dog SF=100

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

0.1

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)

0.045

Rat SF=100

Dermal penetration studies (%)

1.0

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Possible risk to operators identified even with PPE
Harmful by inhalation

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=0.35 µg l⁻¹

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

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
Serious damage to eyes

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not explected to auto-ignite, Not highly flammable

CLP classification 2013

Health: H302, H315, H319
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable and non-reactive under normal conditions of use, storage and transport.

TRANSLATIONS

Language

Name

English

dodine

French

dodine

German

Dodin

Danish

dodine

Italian

dodina

Spanish

dodina

Greek

dodine

Polish

dodyna

Swedish

dodin

Hungarian

dodine

Dutch

dodine

Norwegian

dodin

Record last updated:	13/12/2024
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