Bupirimate (Ref: PP 588)

Bupirimate (Ref: PP 588)	Last updated: 15/03/2024
(Also known as: bupirimat; R-70588)

SUMMARY

A pyrimidine fungicide active against powdery mildew. It has a low aqueous solubility and a low volatility. Depending on local conditions, bupirimate may be moderately persistent in both soil and aquatic systems. It is moderately toxic to most fauna and flora species. It has a low oral toxicity to mammals and is a skin and eye irritant.

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: Moderately persistent; Drainflow: Slightly mobile; Potential for particle bound transport: Medium	Ecotoxicity Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health High alert: Endocrine disrupter

GENERAL INFORMATION

Description

A pyrimidine fungicide active against powdery mildew

Example pests controlled

Powdery mildew

Example applications

Apples; Pumpkins; Squash; Strawberry; Blackcurrant; Raspberry; Gooseberry; Hops; Courgette; Ornamentals

Efficacy & activity

Availability status

Current

Introduction & key dates

1975, first reported; 1975, first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/08/2029

UK LERAP status

Crop 5m - See Authorisation for Crop LERAP Details

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands/UK

Date EC 1107/2009 inclusion expires

31/08/2024

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

Australia

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₂₄N₄O₃S

Canonical SMILES

CCCCC1=C(N=C(N=C1OS(=O)(=O)N(C)C)NCC)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

DSKJPMWIHSOYEA-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H24N4O3S/c1-6-8-9-11-10(3)15-13(14-7-2)16-12(11)20-21(18,19)17(4)5/h6-9H2,1-5H3,(H,14,15,16)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Pyrimidine fungicide

Minimum active substance purity

945 g kg⁻¹

Known relevant impurities

EU dossier - ethirimol, toluene

Substance origin

Synthetic

Mode of action

Systemic with curative and protectant action. Nucleic acid synthesis - adenosin-deaminase.

CAS RN

41483-43-6

EC number

255-391-2

CIPAC number

261

US EPA chemical code

228100

PubChem CID

38884

CLP index number

612-288-00-0

Molecular mass

316.42

PIN (Preferred Identification Name)

5-butyl-2-(ethylamino)-6-methylpyrimidin-4-yl dimethylsulfamate

IUPAC name

5-butyl-2-ethylamino-6-methylpyrimidin-4-yl dimethylsulfamate

CAS name

5-butyl-2-(ethylamino)-6-methyl-4-pyrimidinyl dimethylsulfamate

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

Physical state

Fine white powder to waxy tan coloured solid depending upon purity

Formulations

Property

Value

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

Makhteshim

Example products using this active

Nimrod 25EC

Formulation and application details

Usually supplied as an emulsifiable concentrate that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

13.06

Low

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

23670

n-Heptane

250000

Xylene

250000

Methanol

250000

Acetone

Melting point (°C)

46.9

Boiling point (°C)

232

Degradation point (°C)

Flashpoint (°C)

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

4.79 X 10⁰³

Calculated

Log P

3.68

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.2

Dissociation constant pKa) at 25 °C

4.4

Weak acid

Vapour pressure at 20 °C (mPa)

0.057

Low volatility

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

1.35

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

Neutral solution: 241nm = 21400
Acidic solution: 218nm = 14300, 235nm = 21800
Basic solution: 241nm = 21200

Surface tension (mN m⁻¹)

35.4

at 25°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

107

Persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

332

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 54.4-734 days, DT₉₀ range 126-1432 days; field studies DT₅₀ range 23-69 days; Defra state DT₅₀ range 35-90 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

3.5

Note

Cucumber leaves, undercover, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.02

Fast

Note

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

Value

Moderately persistent

Note

Not greatly senstive to pH but faster under acid conditions

Water-sediment DT₅₀ (days)

42.5

Moderately fast

Water phase only DT₅₀ (days)

6.2

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.

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

Slightly mobile

K_foc

1882

¹/_n

0.94

Notes and range

EU dossier K_f range 12-125 mL g⁻¹, K_foc range 882-2822 mL g⁻¹, ¹/_n range 0.871-1.017, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.11

Calculated

Low leachability

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

Value

2.27 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

1.0

Calculated using the Atkinson method, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

185

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

de-ethylated bupirimate (Ref: DE-B)

Major fraction

0.142

tri-hydroxylated ethirimol

Minor fraction

ethirimol (Ref: PP149)

Major fraction

0.412

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

4-(2-hydroxy-4-ethylamino-6-methylpyrimidinyl)-butan-2-ol

3-hydroxy ethirimol

Rat (Urine); Plant

ethirimol-glucuronide

Rat (Urine, Bile)

methoxy-hydroxy-methyl ethirimol

Surface water

de-ethyl-bupirimate; DE-B

Surface water; Sediment

2-amino-5-butyl-6-methylpyrimidin-4-ol

de-ethyl-ethirimol

Plant

1-ethylguanidine

ethyl guanidine

Plant

urea

Plant

guanidine

Plant

ethirimol (Ref: PP149)

PP149

Surface water; Sediment; Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

4000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 100

Rat

Moderate

(ppm diet)

> 1000

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

> 200

Unknown species Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 10000

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 2091 mg kg feed⁻¹

Anas platyrhynchos

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

≥ 98

Coturnix japonica

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

7.3

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 0.4 mg kg⁻¹ 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

9.0

Formosia candida corr

Non-target plants

Honeybees (Apis spp.)

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

> 50

Apis mellifera

Moderate

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

> 200

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) as % Mortality at dose 0.2 kg ha⁻¹

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as % Mortality at dose 50 g ha⁻¹

Aphidius rhopalosiphi Mummies

Beneficial insects (Predatory mites) as % Mortality at dose 0.174 kg ha⁻¹

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)

1.0

Lepomis macrochirus

Moderate

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

0.3

Oncorhynchus mykiss

Moderate

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

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

> 3.41

Daphnia magna

Moderate

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

0.56

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)

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

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

1.6

Pseudokirchneriella 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)

4000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.9

Rat

Other Mammal toxicity endpoints

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

0.05

Dog SF=100

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

None alocated

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

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

0.05

Dog SF=100

Dermal penetration studies (%)

1.3-12.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses - PPE advised

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

; ; ; ;

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

Possible liver & thyroid toxicant
Endocrine issues - Activation of Pregnane X cellular receptor
CLP data - suspected carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317, H351
Environment: H410

WHO Classification

III (Slightly hazardous)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

bupirimate

French

bupirimate

German

Bupirimat

Danish

bupirimat

Italian

bupirimate

Spanish

bupirimato

Greek

Polish

bupirymat

Swedish

Hungarian

bupirimate

Dutch

bupirimaat

Norwegian

Record last updated:	15/03/2024
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