Ametoctradin (Ref: BAS 650F)

Ametoctradin (Ref: BAS 650F)	Last updated: 31/10/2024
(Also known as: LS 0115)

SUMMARY

Ametoctradin is a fungicide approved for use in many countries for the control of economically damaging fungal diseases on fruit and vegetables. It has a low aqueous solubility and a low volatility. It tends not to be persistent in soils but can be in aquatic bodies under certain conditions. Based on the substances chemical properties there is a low risk of it leaching to groundwater. It generally has a low to moderate toxicity to biodiversity. It is not highly toxic to humans and no chronic health impacts have been identified.

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: Fish acute ecotoxicity: High	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide of the triazolopyrimidine class for the control of certain diseases on potatoes and other crops

Example pests controlled

Late blight; Downy mildews

Example applications

Potatoes; Tomates; Grapes; Curcubits; Lettuce; Cucumber; Vegetables including brassicas, leeks, onions, shallots

Efficacy & activity

Pilot and field studies have demonstrated its efficacy

Availability status

Current

Introduction & key dates

2009, introduced Germany; 2012, first UK approval

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2031

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

31/12/2025

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

Latin America, Morroco

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₂₅N₅

Canonical SMILES

CCCCCCCCC1=C(N2C(=NC=N2)N=C1CC)N

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

GGKQIOFASHYUJZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H25N5/c1-3-5-6-7-8-9-10-12-13(4-2)19-15-17-11-18-20(15)14(12)16/h11H,3-10,16H2,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
ametoctradin	-

General status

Pesticide type

Fungicide

Substance groups

Triazolopyrimidine fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier: amitrol <50mg kg⁻¹; o-xylene <2/0 g kg⁻¹

Substance origin

Synthetic

Mode of action

Selective, preventative, mitochondrial respiration inhibitor by interferring with complex III

CAS RN

865318-97-4

EC number

688-188-6

CIPAC number

818

US EPA chemical code

119210

PubChem CID

15604010

CLP index number

No data found

Molecular mass

275.39

PIN (Preferred Identification Name)

5-ethyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

IUPAC name

5-ethyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

CAS name

5-ethyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

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)

Examples of recorded resistance

None identified

Physical state

Brown granular solid

Formulations

Property

Value

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

BASF

Example products using this active

Resplend
Decabane
Zampro
Enervin
Orvego
Initium

Formulation and application details

Usually supplied as water dispersible granules or suspension concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.15

Low

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

7200

Methanol

100

Toluene

800

Ethyl acetate

1900

Acetone

Melting point (°C)

198

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

234

Flashpoint (°C)

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

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Fat solubility of residues

Solubility

Soluble

Data type

Observed in metabolism and farm animal feeding studies. Detected in eggs and hen fat.

Density (g ml⁻¹)

1.117

Dissociation constant pKa) at 25 °C

2.78

Strong acid

Vapour pressure at 20 °C (mPa)

2.1 X 10^-07

Low volatility

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

4.13 X 10^-07

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Acid soln: 218nm=29557, 241nm=4259, 261nm=2026, 295nm=14288
Neutral soln: 217nm=26485, 237nm=1781, 256nm=3356, 268nm=2530, 294nm=9861
Basic soln: 224nm=12107, 237nm=2775, 256nm=4182, 268nm=3795, 295nm=9977

Surface tension (mN m⁻¹)

72.3

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.8

Non-persistent

DT₅₀ (lab at 20 °C)

1.8

Non-persistent

DT₅₀ (field)

19.7

Non-persistent

DT₉₀ (lab at 20 °C)

11.3

Non-persistent

DT₉₀ (field)

168

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 1-5-3.5 days, DT₉₀ range 6.3-21 days, field studies DT₅₀ range 8.4-130.8 days, DT₉₀ range 48.8-420 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

38.4

Stable

Note

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

Value

Stable

Note

Stable at pH 4, 5, 7 & 9 at 25 °C

Water-sediment DT₅₀ (days)

1.5

Fast

Water phase only DT₅₀ (days)

1.0

Moderately fast

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)

89.6

Non-mobile

K_oc (mL g⁻¹)

7713

Notes and range

EU dossier K_d range 35.8-120 mL g⁻¹, K_foc range 3620-11200 mL.g, soils=7

Freundlich

K_f (mL g⁻¹)

44.9

Slightly mobile

K_foc (mL g⁻¹)

3779

¹/_n

0.767

Notes and range

EU dossier K_f range 14.2-72.8 mL g⁻¹, K_foc range 1580-6620 mL g⁻¹, ¹/_n range 0.677-0.842, soils=7

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.55

Calculated

Low leachability

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

Value

1.02 X 10^-02

Calculated

Note

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

3.26

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

219

Threshold for concern

CT₅₀ (days)

0.52

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

7-amino-5-ethyl{1,2,4)triazolo(1,5-a)pyrimidin-6-carboxylic acid (Ref: M650 F04)

Major fraction

0.557

BASF verified

Ref: M650F31

Minor fraction

Ref: M650F33

Minor fraction

4-(7-amino-5-ethyl(1,2,4) triazolo(1,5-a)pyrimidin-6-yl) butanoic acid (Ref: M650F01)

Major fraction

0.539

BASF verified

3-(7-amino-5-ethyl)(1,2,4)triazolo(1,5-alpha)pyrimidin-6-yl)butanoic acid (Ref: M650F02)

Major fraction

0.130

BASF verified

4-(7-amino-5-ethyl(1,2,4)triazolo(1,5-a)pyrimidin-6-yl)acetic acid (Ref: M650 F03)

Major fraction

0.570

BASF verified

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)

7-amino-5-ethyl{1,2,4)triazolo(1,5-a)pyrimidin-6-carboxylic acid (Ref: M650 F04)

Not relevant

60000

4-(7-amino-5-ethyl(1,2,4)triazolo(1,5-a)pyrimidin-6-yl)acetic acid (Ref: M650 F03)

Not relevant

60000

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

M650F39

Plants

M650F18

Plants

M650F13

Plants

M650F14

Plants

4-(7-amino-5-ethyl(1,2,4) triazolo(1,5-a)pyrimidin-6-yl) butanoic acid
Note: EFSA, 2012

M650F01

Surface water; Sediment

3-(7-amino-5-ethyl)(1,2,4)triazolo(1,5-alpha)pyrimidin-6-yl)butanoic acid
Note: EFSA, 2012

M650F02

Surface water; Sediment

4-(7-amino-5-ethyl(1,2,4)triazolo(1,5-a)pyrimidin-6-yl)acetic acid (Ref: M650 F03)
Note: EFSA, 2012

M650F03

Surface water; Sediment

7-amino-5-ethyl{1,2,4)triazolo(1,5-a)pyrimidin-6-carboxylic acid (Ref: M650 F04)
Note: EFSA, 2012

M650F04

Surface water; Sediment

6-(7-amino-5-ethyl[1,2,4]triazolo[1,5-alpha]pyrimidin-6-yl)hexanoic acid

M650F06

Humans; Animals

M650F28

Plants

M650F32

Plants

M650F33

Plants

M650F48

M650F38

Plants; Water (photolysis)

M650F51

Water (photolysis)

M650F29

Plants

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

≥ 939

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 785 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

≥ 115.2

Colinus virginianus

Moderate

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

> 1000

Eisenia foetida

Low

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

> 20.4

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 3.84 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

>= 268

Folsomia candida

Non-target plants

> 570

10 species
Vegetative vigour, ER₅₀
as g ha⁻¹

> 570

10 species
Seedling emergence, ER₅₀
as g ha⁻¹

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)

> 111.5

Apis mellifera

Low

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

> 9600

Aphidius rhopalosiphi

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

> 9600

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)

> 0.065

Oncorhynchus mykiss

High

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

> 0.048

Pimephales promelas 33 day

Moderate

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

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

> 0.59

Daphnia magna

Moderate

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

0.044

Daphnia magna

Moderate

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)

221.6

Chironomus riparius

Low

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

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

> 0.118

Pseudokirchneriella subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.3

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

Rat SF=100

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

None allocated

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

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

2.0

Rat SF=100

Dermal penetration studies (%)

0.5-3.0

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

GB MRL levels for some commodities subject to change in late 2021

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

; ; ; ;

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

Harmful if swallowed

Handling issues

Property

Value and interpretation

General

Not explosive
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Stability may be affected by light

TRANSLATIONS

Language

Name

English

ametoctradin

French

ametoctradine

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	31/10/2024
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