Pirimicarb (Ref: OMS 1330)

Pirimicarb (Ref: OMS 1330)	Last updated: 22/08/2024
(Also known as: pyrimicarbe; ENT 27766; PP 062)

SUMMARY

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: Drainflow: Moderately mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Reproduction/development effects; Acetyl cholinesterase inhibitor; Neurotoxicant

GENERAL INFORMATION

Description

An insecticide for aphid control in a wide range of crops

Example pests controlled

Aphids of various types including woolly aphid, green peach aphid and the cabbage aphid

Example applications

Wheat; Fruit including strawberries, apples, citrus; Vegetables; Potatoes; Beet crops; Cotton; OSR; Tobacco; Grasshouse crops; Ornamentals

Efficacy & activity

Efficiacy demonstrated via field trials and extensive use across globally.

Availability status

Current

Introduction & key dates

1969, first reported; 1970, first marketed

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2027

UK 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

Sweden

Date EC 1107/2009 inclusion expires

15/03/2025

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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, Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₁H₁₈N₄O₂

Canonical SMILES

CC1=C(N=C(N=C1OC(=O)N(C)C)N(C)C)C

Isomeric SMILES

International Chemical Identifier key (InChIKey)

YFGYUFNIOHWBOB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
pirimicarb	-

General status

Pesticide type

Insecticide

Substance groups

Carbamate insecticide; Dimethylcarbamate insecticide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective, systemic with contact, stomach and respiratory action. Acetylcholinesterase (AChE) inhibitor.

CAS RN

23103-98-2

EC number

245-430-1

CIPAC number

231

US EPA chemical code

106101

PubChem CID

31645

CLP index number

006-035-00-8

Molecular mass

238.39

PIN (Preferred Identification Name)

IUPAC name

2-dimethylamino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate

CAS name

2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate

Other status information

Marine Pollutant; Potential groundwater contaminant

Relevant Environmental Water Quality Standards

UK non-statutory standard for the protection of aquatic life: freshwater and saltwater annual average: 1.0 µg l⁻¹; max acceptable conc. 5 µg l⁻¹

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Aphis gossypii, Aphis nasturtii, Myzus persicae, Nasonovia ribisnigri, Phorodon humuli

Physical state

White solid

Formulations

Property

Value

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

AgriGuard
Clayton
Standon
Syngenta

Example products using this active

Aphox
Dovetail
Pirimor
Pirikill
Pirimor

Formulation and application details

Often supplied as wettable granules that are mixed with water and used as a spray but also available in many other formulations

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3100

High

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

235000

Xylene

350000

Methanol

370000

Acetone

280000

Ethyl acetate

Melting point (°C)

91.6

Boiling point (°C)

325

Degradation point (°C)

Flashpoint (°C)

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

5.01 X 10⁰¹

Calculated

Log P

1.7

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

4.4

Weak base

Vapour pressure at 20 °C (mPa)

0.43

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

3.30 X 10^-05

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

47.4

24 hr

Volatilisation is potentially a concern for short and long range air transport

From soil surface

89.5

24 hr

Volatilisation is potentially a concern for short and long range air transport

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

218.8nm = 5760, 244.7nm = 20900, 272.4nm = 855, 313.5nm = 3800

Surface tension (mN m⁻¹)

64.2

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

73.6

Moderately persistent

DT₅₀ (lab at 20 °C)

73.6

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

348.2

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU 2017 dossier lab studies DT₅₀ (actual) range 5.5-274 days, DT₉₀ (actual) range 18.1->1000 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

5.5

Note

Published literature RL₅₀ range 1.6-14.6 days, 9 field & under cover grown crops, various matrices, n=15

Aqueous photolysis DT₅₀ (days) at pH 7

Value

6.0

Moderately fast

Note

DT₅₀ 0.5 days summer, 12 days winter

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C after 32 days

Water-sediment DT₅₀ (days)

168

Slow

Water phase only DT₅₀ (days)

29.6

Slow

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]; [Peppers: 23.0 days @ 4 DegC]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

8.29

Moderately mobile

K_foc (mL g⁻¹)

388

¹/_n

0.87

Notes and range

EU dossier K_f range 0.35-26.0 mL g⁻¹, K_foc range 45.0-730 mL g⁻¹; ¹/_n range 0.83-0.91, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.35

Calculated

Low leachability

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

Value

1.68 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

1.0

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)

(Other literature Log BCF range 1.5-1.7 (R3))

Low potential

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

2-dimethylamino-5,6-dimethylpyrimidin-4-ol (Ref: R31805)

Major fraction

0.265

5,6-dimethyl-2-(methylamino)pyrimidin-4-ol (Ref: R34865)

Major fraction

0.312

5,6-dimethyl-2-(methylformamido)pyrimidin-4-yl dimethylcarbamate (Ref: R34885)

Major fraction

0.124

1,1-dimethylguanidine (Ref: R16210)

Photolysis

2-amino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (Ref: R35140)

Minor fraction

0.002

5,6-dimethyl-2-(methylamino)pyrimidin-4-yl dimethylcarbamate (Ref: R34836)

Major fraction

0.192

Aerobic, Photolysis

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-amino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate (Ref: R35140)

Plant

desmethylformamido pirimicarb (Ref: R34885)
Note: Plant DT50 Lettuce leaves 0.94-1.29 days, R4

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

142

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 37.5

Rat

High

(ppm diet)

> 750

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

81.8

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

20.9

Colinus virginianus

High

Birds - Short term dietary (LC₅₀/LD₅₀)

394 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

12.1

Anas platyrhynchos NOEL

Moderate

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

653

Eisenia foetida

Moderate

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

5.46

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 5.0 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

33.0

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

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

17.8

Apis mellifera 120 hr

Moderate

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

4.0

Apis mellifera 24 hr

Moderate

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

2.51

Apis mellifera

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)

8.5

Bombus terrestris 24 hr

Moderate

Mason bees (Osmia spp.)

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

115.1

Osmia bicornis

Low

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 48 hr

620

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

835

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)

> 100

Pimephales promelas

Low

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

< 18

Oncorhynchus mykiss

Low

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

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

0.017

Daphnia magna

High

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

0.0009

Daphnia magna

High

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)

> 60

Chironomus riparius 48 hr

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

> 10

Chironomus riparius

Low

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)

140

Pseudokirchneriella subcapitata

Low

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

Unknown species

Low

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)

142

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.75

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.035

Dog SF=100

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

0.1

Rat 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)

0.035

Dog SF=100

Dermal penetration studies (%)

0.1-14.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

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

Extensive metabolism, excreted mainly in the urine with smaller amounts in the faeces (up to 10%)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin
US EPA - probable human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 6.1
Not expected to auto-ignite; Not highly flammable
Not compatible with strong oxidising agents

CLP classification 2013

Health: H301, H317, H331,H351
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

UN2757

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

Chemically stable under standard ambient conditions

TRANSLATIONS

Language

Name

English

pirimicarb

French

pyrimicarbe

German

Pirimicarb

Danish

pirimicarb

Italian

pirimicarb

Spanish

pirimicarb

Greek

pirimicarb

Polish

pirimikarb

Swedish

pirimikarb

Hungarian

pirimicarbe

Dutch

pirimicarb

Norwegian

pirimikarb

Record last updated:	22/08/2024
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