Imazamethabenz-methyl (Ref: AC 222293)-Pesticide database

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Imazamethabenz-methyl (Ref: AC 222293)

(Also known as: imazamethabenz, methyl variant; CL 222293)

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 High alert: GUS: High leachability; Drainflow: Mobile	Ecotoxicity Moderate alert: Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Possible Reproduction/development effects

GENERAL INFORMATION

A post-emergence herbicide for use in winter cereals and other crops to control grasses and some dicotyledonous weeds

Example pests controlled

Grasses and some dicotyledonous weeds

Example applications

Sunflowers; Wheat; Barley

Efficacy & activity

Availability status

Introduction & key dates

1982, first reported; 1998, first registered 1988

UK regulatory status

UK COPR regulatory status

Date COPR inclusion expires

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Dossier rapporteur/co-rapporteur

Date EC 1107/2009 inclusion expires

EU Candidate for substitution (CfS)

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

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

Chemical structure

A chiral molecule

Chemical formula

C₁₆H₂₀N₂O₃

Canonical SMILES

COC(=O)c1ccc(C)cc1C2=NC(C)(C(C)C)C(=O)N2.COC(=O)c3cc(C)ccc3C4=NC(C)(C(C)C)C(=O)N4

Isomeric SMILES

International Chemical Identifier key (InChIKey)

WXUNXXKSYBUHMK-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H20N2O3/c1-9(2)16(4)15(20)17-13(18-16)12-8-10(3)6-7-11(12)14(19)21-5/h6-9H,1-5H3,(H,17,18,20)

2D structure diagram/image available?

Substance groups

Imidazolinone herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Selective, systemic absorbed through roots and leaves. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.

US EPA chemical code

CLP index number

PIN (Preferred Identification Name)

mix of methyl 6-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-m-toluate and methyl 2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-p-toluate

methyl 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(or 5)-methylbenzoate

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Avena fatua, Alopecurus myosuroides

Off-white powder

Related substances & organisms

imazamethabenz

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

BASF
Nufarm Americas Inc.

Example products using this active

Assert

Formulation and application details

Usually supplied as a liquid concentrate or as soluble granules.

ENVIRONMENTAL FATE

Source; quality score; and other information

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

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

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

C4 C = AGRITOX dataset. Dataset is no longer available.
4 = Verified data

C4 C = AGRITOX dataset. Dataset is no longer available.
4 = Verified data

C4 C = AGRITOX dataset. Dataset is no longer available.
4 = Verified data

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Melting point (°C)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data

Fat solubility of residues

Density (g ml⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Dissociation constant pKa) at 25 °C

DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. Dataset is no longer available.
4 = Verified data

Vapour pressure at 20 °C (mPa)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data

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

Surface tension (mN m⁻¹)

Source; quality score; and other information

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

Moderately persistent

DT₅₀ (lab at 20 °C)

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

General literature DT₅₀ range 45-57 days (R3)

Dissipation rate RL₅₀ on plant matrix

Dissipation rate RL₅₀ on and in plant matrix

Aqueous photolysis DT₅₀ (days) at pH 7

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

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

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

Slow at pH 5 to pH7, rapid at pH 9

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

Moderately fast

Soil adsorption and mobility

Source; quality score; and other information

H3 H = The US ARS pesticide properties database. Dataset is no longer available.
3 = Unverified data of known source

Notes and range

Other sources: 51 mL g⁻¹ (DW3)

Notes and range

Source; quality score; and other information

GUS leaching potential index

High leachability

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

1.21 X 10⁰⁰

Potential for particle bound transport index

Potential for loss via drain flow

Bio-concentration factor

BCF (l kg⁻¹)

Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source

Based on LogP < 3

CT₅₀ (days)

Known soil metabolites

Major/Minor fraction

Estimated maximum occurrence fraction

imazamethabenz (Ref: AC 263840)

Known groundwater metabolites

None

Other known metabolites

None

Terrestrial ecotoxicology

Source; quality score; and other information

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Short term dietary NOEL

L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source

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

Birds - Acute LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Anas platyrhynchos

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Eisenia foetida

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

Soil micro-organisms

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)

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

K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data

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)

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

Source; quality score; and other information

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Oncorhynchus mykiss

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

J4 J = Pesticide Action Network database (click here )
4 = Verified data

Daphnia magna

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)

F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data

Pseudokirchneriella subcapitata

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

Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source

Unknown species

Mesocosm study data

NOEAEC mg l⁻¹

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

Source; quality score; and other information

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

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

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Mammals - Inhalation LC₅₀ (mg l⁻¹)

L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source

Other Mammal toxicity endpoints

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

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

EU MRL pesticide database

GB MRL Register

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Specific human health issues

Endocrine disruptor

XNo, known not to cause a problem

A3 A = Chromosome aberration (EFSA database)
3 = Negative

B0 B = DNA damage/repair (EFSA database)
0 = No data

C0 C = Gene mutation (EFSA database)
0 = No data

D0 D = Genome mutation (EFSA database)
0 = No data

E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data

Reproduction / development effects

Acetyl cholinesterase inhibitor

?Possibly, status not identified

XNo, known not to cause a problem

XNo, known not to cause a problem

Respiratory tract irritant

Skin sensitiser

✓Yes, known to cause a problem

XNo, known not to cause a problem

✓Yes, known to cause a problem

General human health issues

May cause irreversible eye damage

Handling issues

Value and interpretation

Prevent generation of mists
Corrosive

CLP classification 2013

Not classified: Obsolete

WHO Classification

U (Unlikely to present an acute hazard)

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

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