Ametoctradin (Ref: BAS 650F)

Ametoctradin (Ref: BAS 650F)	Last updated: 14/01/2021
(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 chonic health impacts have been identified.

GENERAL INFORMATION

Description

Novel 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, Germany, first UK approval July 2010

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2026

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands

Date EC 1107/2009 inclusion expires

31/07/2023

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

Latin America from late 2010

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 group

Triazolopyrimidine

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

CIPAC number

818

US EPA chemical code

PubChem CID

15604010

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

Suitable for IPM

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

None identified

Physical state

Brown granular solid

Related substances & organisms

mancozeb

dimethomorph

Formulations

Property

Value

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

Resplend
Decabane
Zampro
Enervin
Orvego
Initium

Example products using this active

BASF

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)

Not expected to self ignite; Not highly flammable

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

2.51 X 10⁰⁴

Calculated

Log P

4.4

High

Bulk 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

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 on plant matrix

Value

Note

Dissipation rate RL₅₀ 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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

89.6

Non-mobile

K_oc

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

44.9

Slightly mobile

K_foc

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

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

4-(7-amino-5-ethyl(1,2,4) triazolo(1,5-a)pyrimidin-6-yl) butanoic acid (Ref: M650 F01)

Soil

0.539

Major fraction, Relevant

3-(7-amino-5-ethyl)(1,2,4)triazolo(1,5-alpha)pyrimidin-6-yl)butanoic acid (Ref: M650 F02)

Soil

0.130

Major fraction, Relevant

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

Soil

0.570

Major Fraction, Relevant

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

Soil

0.557

Major Fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

M650F06

Humans; Animals

M650F28

Plants

-
Note: Minor product

M650F31

Soil

M650F32

Plants

-
Note: Minor product

M650F33

Soil; Plants

M650F48

M650F38

Plants; Water (photolysis)

M650F51

Water (photolysis)

M650F29

Plants

M650F39

Plants

M650F18

Plants

M650F13

Plants

M650F14

Plants

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

219

Threshold for concern

CT₅₀ (days)

0.52

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⁻¹ BW/day

Anas platyrhynchos

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

≥ 115.2

Colinius virginianus

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.065

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

> 0.048

Pimephalis promelas 33 day

Moderate

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

> 0.59

Daphnia magna

Moderate

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

0.044

Daphnia magna

Moderate

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)

Non-target plants

> 570

10 species
Vegetative vigour, ER₅₀
as g ha⁻¹

> 570

10 species
Seedling emergence, ER₅₀
as g ha⁻¹

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

> 0.118

Pseudokirchneriella subcapitata

Moderate

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

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)

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)

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

> 1000

Eisenia foetida

Low

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

20.4

Eisenia foetida

Chronic NOEC (mg kg⁻¹)

> 268

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

3.2

>, as L product ha⁻¹ (BAS 651 00F: conc 300g l⁻¹)
Typhlodromus pyri

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

3.2

>, as L product ha⁻¹ (BAS 651 00F: conc 300g l⁻¹)
Aphidius rhopalosiphi

% Effect

Soil micro-organisms

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

Dose: 3.84 mg kg⁻¹ 28 days

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)

> 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)

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

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

CLP classification 2013

Health: H302

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R52/53, R51/53

EC Safety Classification

S2, S13, S20/21, S36/37, S46

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

ametoctradin

French

ametoctradine

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Record last updated:	14/01/2021
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