Pyriminobac-methyl (Ref: KIH-6127)

Pyriminobac-methyl (Ref: KIH-6127)	Last updated: 19/01/2023
(Also known as: KUH-920)

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: Slightly mobile Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate	Human health Low alert Warning: Significant data are missing

GENERAL INFORMATION

Description

A herbicide used post-emergence for the selective control of grass in paddy fields

Example pests controlled

Barnyard grass

Example applications

Paddy rice

Efficacy & activity

Availability status

Introduction & key dates

1996, Japan

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

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

Additional information

Also used in

Chemical structure

Isomerism

Isomeric - substance has one E/Z centre.

Chemical formula

C₁₇H₁₉N₃O₆

Canonical SMILES

CC(=NOC)C1=C(C(=CC=C1)OC2=NC(=CC(=N2)OC)OC)C(=O)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

USSIUIGPBLPCDF-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H19N3O6/c1-10(20-25-5)11-7-6-8-12(15(11)16(21)24-4)26-17-18-13(22-2)9-14(19-17)23-3/h6-9H,1-5H3/b20-10?

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Pyrimidinyloxybenzoic herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Branched chain amino acid synthesis inhibitor. Selective, systemic, absorbed by foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.

CAS RN

136191-64-5

EC number

603-944-7

CIPAC number

US EPA chemical code

PubChem CID

9604652

CLP index number

No data found

Molecular mass

361.35

PIN (Preferred Identification Name)

methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[(1E)-N-methoxyethanimidoyl]benzoate

IUPAC name

methyl (EZ)-2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(1-methoxyiminoethyl)benzoate

CAS name

methyl 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-6-[1-(methoxyimino)ethyl]benzoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White powder

Formulations

Property

Value

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

Kumiai

Example products using this active

Patful

Formulation and application details

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

9.25

Low

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

14600

Methanol

456

n-Hexane

126000

Acetone

64600

Ethyl acetate

Melting point (°C)

105

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

2.04 X 10⁰²

Calculated

Log P

2.31

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.031

Low volatility

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

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

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

205

Stable

Note

In natural water

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

736

Notes and range

Varies with isomer: 972 mL g⁻¹ (E-isomer), 499 mL g⁻¹ (Z-isomer)

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

> 1000

Eisenia foetida

Low

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

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 200

Low

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

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)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 21.2

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 63.8

Daphnia carinata

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

20.6

Pseudokirchneriella subcapitata

Low

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.5

Rat

Other Mammal toxicity endpoints

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

0.009

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

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

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

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

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Name

English

pyriminobac-methyl

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Record last updated:	19/01/2023
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