Dodine (Ref: BAS 365F)

Dodine (Ref: BAS 365F)	Last updated: 18/01/2021
(Also known as: cytrex; doguadine; tsitrex; CL 7521; carpene)

GENERAL INFORMATION

Description

A fungicide used to control scab, leaf spot and other foliar diseases. 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

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/05/2024

UK 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

31/05/2021

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
✓		✓	✓	✓	✓	✓	✓	✓

Also used in

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₃₃N₃O₂

Canonical SMILES

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

Isomeric SMILES

No data

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 group

Guanidine

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

CAS RN

2439-10-3

EC number

219-459-5

CIPAC number

101

US EPA chemical code

044301

PubChem CID

17110

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

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

Dodifun 400SC
Radspor L
Syllit 400SC

Example products using this active

Clayton
Greencrop
Hermoo

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)

Not expected to self ignite; Not highly flammable

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

1.78 X 10⁰¹

Calculated

Log P

1.25

Low

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

10472

Non-mobile

K_oc

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

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-2.95

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

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: Dodine-M01

guanidine

Plant

0.36

urea

Plant

dodecyl guanidine carboxylic acid

Animal

octylguanidine carboxylic acid

Animal

hexylguanidine carboxylic acid

Animal

Ref: Dodine-M02

hydroxydodecylguanidine

Animal (Urinary)

0.23

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

851

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.57

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.099

Pimephales promelas 30 day

Moderate

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

0.018

Daphnia magna

High

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

0.0044

Daphnia magna

High

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)

Non-target plants

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

0.0028

Pseudokirchneriella subcapitata

High

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)

> 100

Low

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

> 200

Low

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)

547

Eisenia foetida

Moderate

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

171

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

1800

>, 48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

7512

>, 7 day
Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 9 kg ha⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.041

Aquatic invertebrates

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)

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

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

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 Code is usually 9

CLP classification 2013

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

EC Risk Classification

Xn - Harmful: R22
Xi - Irritant: R36/38
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S26, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

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

Record last updated:	18/01/2021
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