Pyrimethanil (Ref: SN 100309)

Pyrimethanil (Ref: SN 100309)	Last updated: 12/01/2021
(Also known as: ZK 100309)

GENERAL INFORMATION

Description

A fungicide used to control fungal pathogens on fruit, vegetables and ornamentals

Example pests controlled

Grey mould; Powdery mildew; Scab; Downym mildew; Phomopis leaf spot; Botrytis

Example applications

Almonds; Pistachios; Fruit including grapes, stone fruits (except cherries), pome fruits, strawberries; Potatoes and other tuberous and corm vegetables; Tomatoes.; ornamentals

Efficacy & activity

Efficiacy demonstrated via field trials and extensive use

Availability status

Current

Introduction & key dates

1998, USA

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Czech Republic/Austria

Date EC 1107/2009 inclusion expires

30/04/2021

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

Chemical structure

Isomerism

Chemical formula

C₁₂H₁₃N₃

Canonical SMILES

CC1=CC(=NC(=N1)NC2=CC=CC=C2)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ZLIBICFPKPWGIZ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H13N3/c1-9-8-10(2)14-12(13-9)15-11-6-4-3-5-7-11/h3-8H,1-2H3,(H,13,14,15)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
pyrimethanil	-

General status

Pesticide type

Fungicide

Substance group

Anilinopyrimidine

Minimum active substance purity

975 g kg⁻¹

Known relevant impurities

EU dossier - cyanamide <0.5g kg⁻¹

Substance origin

Synthetic

Mode of action

Protective action with some curative properties. Inhibits methionine protein synthesis.

CAS RN

53112-28-0

EC number

414-220-3

CIPAC number

714

US EPA chemical code

288201

PubChem CID

91650

Molecular mass

199.28

PIN (Preferred Identification Name)

IUPAC name

N-(4,6-dimethylpyrimidin-2-yl)aniline

CAS name

4,6-dimethyl-N-phenyl-2-pyrimidinamine

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

White to off-white crystalline powder

Related substances & organisms

propylene glycol

chlorothalonil

Formulations

Property

Value

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

Scala
Walabi
Botrynil

Example products using this active

BASF

Formulation and application details

Often supplied as a soluble concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

110

Moderate

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

23700

n-Hexane

412300

Toluene

388800

Acetone

616900

Ethyl acetate

Melting point (°C)

96.3

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

189.9

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.92 X 10⁰²

Calculated

Log P

2.84

Moderate

Bulk density (g ml⁻¹)

1.19

Dissociation constant pKa) at 25 °C

3.52

Weak base

Vapour pressure at 20 °C (mPa)

1.1

Low volatility

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

2.2 X 10^-03

Non-volatile

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

Neutral solution: 205nm = 16280, 211nm = 13450, 229nm = 4870, 271nm = 27200
Acidic solution: 205nm = 16450, 245nm = 12260, 260nm = 14620, 317nm = 5300

Surface tension (mN m⁻¹)

63.31

at 20°C 0.1 g l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

50.9

Moderately persistent

DT₅₀ (lab at 20 °C)

50.9

Moderately persistent

DT₅₀ (field)

31.4

Moderately persistent

DT₉₀ (lab at 20 °C)

254.1

Persistent

DT₉₀ (field)

143.9

DT₅₀ modelling endpoint

44.4

normalised geometric mean

Note

EU 2017 dossier lab studies DT₅₀ (actual) range 26.8-71.8 days, DT₉₀ (actual) range 89.1-377.1 days, Soils=4; Field studies DT₅₀ (normalised) range 5.3-34.5 days, DT₉₀ (actual) range 59.4-143.9 days, Soils=10

Dissipation rate RL₅₀ on plant matrix

Value

6.1

Note

Published literature RL₅₀ range 2.7-12.0 days, 2 field & undercover grown crops, various matrices, n=4

Dissipation rate RL₅₀ on and in plant matrix

Value

15.1

Note

Published literature RL₅₀ range 3.0-57.0 days, 5 field & undercover grown crops, various matrices, n=12

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Not significant degradation route

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

Value

Stable

Note

Stable pH 5 to pH 9 at 22 °C

Water-sediment DT₅₀ (days)

81.0

Moderately fast

Water phase only DT₅₀ (days)

6.7

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

8.38

Moderately mobile

K_foc

355.7

¹/_n

0.864

Notes and range

EU 2017 dossier kf range 2.51-23.44 mL g⁻¹, K_foc range 75-751 mL g⁻¹, ¹/_n range 0.833-0.907, Soils=9

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.17

Calculated

Transition state

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

Value

9.13 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

2-amino-4,6-dimethylpyrimidine (Ref: AE-F1312593)

Soil

0.115

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

(2-(4-hydroxyanilino)-4,6-dimethylpyrimidine

Animal

2-anilino-4,6-dimethylpyrimidin-5-ol

Animal

2-amino-4,6-dimethyl-pyrimidine

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

4150

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 139

Rat

Moderate

(ppm diet)

> 900

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

> 239

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5200 mg kg feed⁻¹

Colinus virginianus

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

95.96

Colinus virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

10.56

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

1.6

Oncorhynchus mykiss LOEC

Moderate

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

2.9

Daphnia magna

Moderate

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

0.94

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)

4.0

Chironomus riparius

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

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

7.8

Lemna gibba

Moderate

Non-target plants

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

1.2

Raphidocelis 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)

> 100

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)

> 400

Bombus terrestris

Low

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

> 579.7

Bombus terrestris

Low

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)

313

Eisenia foetida corr

Moderate

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

4.12

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

63 / 18

Mortality / Fecundity [Dose: 1 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

38 / 52

Mortality / Fecundity [Dose: 1.04 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect [Dose: 1.08 mg kg⁻¹ soil]
Carbon mineralisation: No significant adverse effect [Dose: 10.8 mg kg⁻¹ soil]

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)

4150

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.98

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.17

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)

None allocated

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

0.13

Rat SF=100

Dermal penetration studies (%)

1.0-46.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

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

Eye irritant

Phototoxicant

General human health issues

Possible liver, kidney, adrenals, bladder and thyroid toxicant
USEPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Environment: H411

EC Risk Classification

N - Dangerous for the environment: R51, R53

EC Safety Classification

WHO Classification

III (Slightly hazardous)

UN Number

3082

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

pyrimethanil

French

pyrimethanil

German

Pyrimethanil

Danish

pyrimethanil

Italian

pirimetanil

Spanish

pirimetanil

Greek

Polish

pyrimetanil

Swedish

pyrimetanil

Hungarian

pirimetanil

Dutch

pyrimethanil

Record last updated:	12/01/2021
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