Guazatine (Ref: EM 379)

Guazatine (Ref: EM 379)	Last updated: 04/02/2024
(Also known as: guanoctine; MC 25; iminoctadine)

SUMMARY

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: Birds acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide seed dressing used to control a range of pathogens mainly on citrus fruit.

Example pests controlled

Septoria, Fusarium, Alternaria and Helminthosporium spp.

Example applications

Citrus fruits including oranges, manderines, lemons, grapefruit, pineapple, melon; Sugarcane

Efficacy & activity

Availability status

Current

Introduction & key dates

1974, introduced Sweden; circa 1986, commercially available

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Korea; Taiwan

Chemical structure

Isomerism

None

Chemical formula

C₁₈H₄₁N₇

Canonical SMILES

C(CCCCN=C(N)N)CCCNCCCCCCCCN=C(N)N

Isomeric SMILES

International Chemical Identifier key (InChIKey)

RONFGUROBZGJKP-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H41N7/c19-17(20)24-15-11-7-3-1-5-9-13-23-14-10-6-2-4-8-12-16-25-18(21)22/h23H,1-16H2,(H4,19,20,24)(H4,21,22,25)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Guanidine fungicide; Aliphatic nitrogen fungicide

Minimum active substance purity

500 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Inhibition of lipid biosynthesis. Multi-site activity. Broad-spectrum. Protectant

CAS RN

13516-27-3

Alternative/old CAS RN

108173-90-6

EC number

236-855-3

CIPAC number

361

US EPA chemical code

498200

PubChem CID

3526

CLP index number

No data found

Molecular mass

355.57

PIN (Preferred Identification Name)

1,1'-(iminodioctamethylene)diguanidine

IUPAC name

1,1'-(iminodioctamethylene)diguanidine

CAS name

N,N'-(iminodi-8,1-octanediyl)bis[guanidine]

Other status information

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)

M07

Examples of recorded resistance

Physical state

Brown solid, product is orange liquid

Related substances & organisms

iminoctadine triacetate

iminoctadine tris(albesilate)

Formulations

Property

Value

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

Makhteshim-Agan
Murphy
Kenogard
Nippon Soda Co.

Example products using this active

Ravine Plus
Panoctine 35
Kenopel
Panolil
Mitrol
Befran

Formulation and application details

Often supplied as an aqueous solution for use as a seed treatment

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

6000000

High

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

2000000

Ethanol

510000

Methanol

100

Acetone

100

Toluene

Melting point (°C)

Boiling point (°C)

100

Degradation point (°C)

165

Flashpoint (°C)

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

1.00 X 10^-04

Calculated

Log P

-4.0

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.06

Dissociation constant pKa) at 25 °C

Pka(2) = 4.6, Acetate salt of strong base

Vapour pressure at 20 °C (mPa)

0.01

Low volatility

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

3.80 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

No absorbance above 290nm

Surface tension (mN m⁻¹)

66.87

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

68.5

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 10.8-38.2 days, DT₉₀ range 36-127 days; Other studies Lab studies DT₅₀ range 400-600 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

469

Note

Apple leaves, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 for 30 days at 25 °C

Water-sediment DT₅₀ (days)

100

Slow

Water phase only DT₅₀ (days)

Stable

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.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Non-mobile

K_oc

25000

Notes and range

Literature K_oc range 3646-46250 mL g⁻¹

Freundlich

K_f

492.1

Non-mobile

K_foc

14152

¹/_n

1.09

Notes and range

EU dossier K_f range 85.33-2404 mL g⁻¹, K_foc range 3646-15390 mL g⁻¹, ¹/_n range 0.999=1.271, Soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.19

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

Bio-concentration factor

BCF (l kg⁻¹)

0.04

Low potential

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

308

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 10

Rat

High

(ppm diet)

> 200

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

> 27

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

57.9

Columba livia

High

Birds - Short term dietary (LC₅₀/LD₅₀)

164.4 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

18.9

Coturnix japonica

Moderate

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

3420

Eisenia foetida

Low

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

14.4

Eisenia foetida

Moderate

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

103.4

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

> 100

Apis mellifera

Low

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

> 59

Apis mellifera

Moderate

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

Chronic

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

> 120

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortilty LR₅₀ g ha⁻¹

> 120

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ g/h

> 120

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.42

Lepomis macrochirus

Moderate

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

0.044

Oncorhynchus mykiss

Moderate

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

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

0.15

Daphnia magna

Moderate

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)

0.0135

Raphidocelis subcapitata

Moderate

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

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)

308

Rat

Moderate

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

1064

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.163

Rat

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 (%)

0.4-6.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (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

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
Although no conclusive evidence regarding carcinogenity available some studies raise concerns

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Ensure adequate ventilation when using
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302, H312, H315, H318, H330, H335
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

guazatine

French

triacétate de guazatine

German

Guazatin

Danish

guazatin

Italian

guazatina

Spanish

guazatina

Greek

Polish

guazatyna

Swedish

guazatinacetater

Hungarian

guazatin

Dutch

Norwegian

Record last updated:	04/02/2024
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