Mepanipyrim (Ref: KUF 6201)

Mepanipyrim (Ref: KUF 6201)	Last updated: 12/01/2021
(Also known as: KIF 3535)

GENERAL INFORMATION

Description

A fungicide used to control a wide range of fungal diseases mainly on salads and fruit.

Example pests controlled

Grey mould (Botryotinia fuckeliana); Scab

Example applications

Strawberries; Grapes; Blackberries; Raspberries; Tomatoes; Apples; Pears; Cucumber; Peppers; Aubergine

Efficacy & activity

Efficacy demonstrated via long term use and experimental field studies

Availability status

Current

Introduction & key dates

1995

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

Belgium/Greece

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

Chemical structure

Isomerism

Chemical formula

C₁₄H₁₃N₃

Canonical SMILES

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

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

CIFWZNRJIBNXRE-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H13N3/c1-3-7-13-10-11(2)15-14(17-13)16-12-8-5-4-6-9-12/h4-6,8-10H,1-2H3,(H,15,16,17)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Other susbtance

Other constituent type

Bactericide, Wood preservative

Substance group

Anilinopyrimidine

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - toluene < 5g kg⁻¹

Substance origin

Synthetic

Mode of action

Non-systemic with preventative action. Inhibits protein synthesis.

CAS RN

110235-47-7

EC number

432-140-7

CIPAC number

611

US EPA chemical code

288203

PubChem CID

86296

Molecular mass

223.27

PIN (Preferred Identification Name)

IUPAC name

N-(4-methyl-6-prop-1-ynylpyrimidin-2-yl)aniline

CAS name

4-methyl-N-phenyl-6-(1-propynyl)-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 crystals

Formulations

Property

Value

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

Frupica SC

Example products using this active

Certis

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)

2.08

Low

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

139000

Acetone

15400

Methanol

102000

Ethyl acetate

277000

Dichloromethane

Melting point (°C)

132.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

288

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.91 X 10⁰³

Calculated

Log P

3.28

High

Bulk density (g ml⁻¹)

1.205

Dissociation constant pKa) at 25 °C

2.7

Strong acid

Vapour pressure at 20 °C (mPa)

0.0232

Low volatility

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

1.67 X 10^-03

Non-volatile

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

Neutral solution: 344nm = 3170, 287nm = 29400
Acidic solution: 358nm = 5020, 278nm = 28300
Basic solution: 344nm = 3220, 287nm = 29800

Surface tension (mN m⁻¹)

72.0

at 24 °C 99.7%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

142.2

Persistent

DT₅₀ (lab at 20 °C)

142.2

Persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

582.5

Very persistent

DT₉₀ (field)

188

DT₅₀ modelling endpoint

Note

EU 2016 dossier Lab studies DT₅₀ range 38.8-253.9 days, DT₉₀ range 128.9->1000 days, Soils=4; EU 2001 dossier Lab studies DT₅₀ range 46-191 days, DT₉₀ range 152.9-636 days, field study DT₅₀ range 34-75 days, DT₉₀ range 114-249.3 days

Dissipation rate RL₅₀ on plant matrix

Value

4.7

Note

Tomato fruit, undercover, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

8.2

Note

Published literature RL₅₀ range 3.6-12.8 days, 2 field & undercover grown crops, various matrices, n=2

Aqueous photolysis DT₅₀ (days) at pH 7

Value

21.4

Slow

Note

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

Value

Stable

Note

Stable pH 5 to pH 7 to pH 9 under environmental conditions, DT₅₀ 57 days at pH 9, 70 °C

Water-sediment DT₅₀ (days)

14.5

Fast

Water phase only DT₅₀ (days)

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

44.88

Slightly mobile

K_foc

874

¹/_n

0.83

Notes and range

EU dossier K_f range 6.32-159.8, K_foc range 395-5859 mL g⁻¹, Soils=5

pH sensitivity

Yes - increases as pH decreases

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.86

Calculated

Transition state

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

Value

6.53 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-methyl-6-(1-propynyl)-pyrimidin-2-ylamine

Soil

1-(2-anilino-6-methylpyrimidin-4-yl)-2-propanone

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

280

Threshold for concern

CT₅₀ (days)

0.8

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

7.0

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 ppm feed

Anas platyrhynchos

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

100

Colinius virginianus NOEC

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.74

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.029

Oncorhynchus mykiss

Moderate

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

0.63

Daphnia magna

Moderate

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

0.031

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)

1.2

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)

0.23

Raphidocelis subcapitata

Moderate

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

1.2

Unknown species

Low

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)

> 50

Apis mellifera

Moderate

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)

> 100

Bombus terrestris

Low

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

> 100

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)

> 500

corr

Moderate

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

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

Beneficial capacity [Dose: 0.5 kg ha⁻¹]
Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

-96

Beneficial capacity [Dose: 0.5 kg ha⁻¹]
Trichogramma cacoeciae

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect [Dose 5.2 mg kg⁻¹ soil]
Carbon mineralisation: No significant adverse effect

Dose: 3.34 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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.59

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.012

Rat SF=200

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

0.1

Rabbit SF=100

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

0.1

Rabbit SF=100

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

0.012

Rat SF=200

Dermal penetration studies (%)

0.4-13.0

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

No data found

Eye irritant

Phototoxicant

General human health issues

Possible liver & prostate toxicant
USEPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H351
Environment: H400, H410

EC Risk Classification

Carcinogen category 2: R41
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36/37, S46, S60, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

mepanipyrim

French

mepanipyrim

German

Mepanipyrim

Danish

mepanipyrim

Italian

mepanipirim

Spanish

mepanipirina

Greek

Polish

mepanipyrim

Swedish

mepanipyrim

Hungarian

Dutch

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