Imazamethabenz-methyl (Ref: AC 222293)	Last updated: 29/08/2024
(Also known as: imazamethabenz, methyl variant; CL 222293)

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

GENERAL INFORMATION

Description	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	Current
Introduction & key dates	1982, first reported; 1988, first registered

GB regulatory status

GB COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
GB LERAP status	No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status	Not approved
Dossier rapporteur/co-rapporteur	-
Date EC 1107/2009 inclusion expires	Expired
EU Candidate for substitution (CfS)	Not applicable
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	USA

Chemical structure

Isomerism	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	No data
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?	Yes

General status

Pesticide type	Herbicide
Substance groups	Imidazolinone herbicide
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Selective, systemic absorbed through roots and leaves. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.
CAS RN	81405-85-8
EC number	617-231-3
CIPAC number	529
US EPA chemical code	128842
PubChem CID	54744
CLP index number	No data found
Molecular mass	288.3
PIN (Preferred Identification Name)	-
IUPAC 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
CAS name	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 Class (HRAC MoA class)	B
Herbicide Resistance Class (WSSA MoA class)	2
Insecticide Resistance Class (IRAC MoA class)	Not applicable
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	Avena fatua, Alopecurus myosuroides
Physical state	Off-white powder
Related substances & organisms	imazamethabenz

Formulations

Property	Value
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

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		1114	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		291000	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Acetone	-
		135000	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Chloroform	-
		57500	C4 C = AGRITOX dataset. Dataset is no longer available. 4 = Verified data Xylene	-
		400	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source n-Hexane	-
Melting point (°C)		131	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)		93	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source (closed cup)	-
Octanol-water partition coefficient at pH 7, 20 °C	P	3.47 X 1001	Calculated	-
	Log P	1.54	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Low
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		0.3	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Dissociation constant pKa) at 25 °C		2.9	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	-
		Strong acid
Vapour pressure at 20 °C (mPa)		1.50 X 10-03	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		5.05 X 10-07	H4 H = The US ARS pesticide properties database. Dataset is no longer available. 4 = Verified data	Non-volatile
Volatilisation as max % of applied dose lost	From plant surface	-	-	-
	From soil surface	-	-	-
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)	47	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)	47	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	-	-	-
	Note	General literature DT₅₀ range 45-57 days (R3)
Dissipation rate RL₅₀ (days) on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ (days) on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	36	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Stable
	Note	-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7	Value	133	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Persistent
	Note	Slow at pH 5 to pH7, rapid at pH 9
Water-sediment DT₅₀ (days)		-	-	-
Water phase only DT₅₀ (days)		7	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Moderately fast
Sediment phase only DT₅₀ (days)		-	-	-
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		-

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd (mL g⁻¹)	-	H3 H = The US ARS pesticide properties database. Dataset is no longer available. 3 = Unverified data of known source	Mobile
	Koc (mL g⁻¹)	35
	Notes and range	Other sources: 51 mL g⁻¹ (DW3)
Freundlich	Kf (mL g⁻¹)	-	-	-
	Kfoc (mL g⁻¹)	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		4.11	Calculated	High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	1.21 X 1000	Calculated	-
	Note	-
Potential for particle bound transport index		Medium	Calculated	-
Potential for loss via drain flow		Mobile	Calculated	-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk		-	-	-
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source Based on LogP < 3	Low risk
	CT₅₀ (days)	-		-

Known soil metabolites

Metabolite	Major/Minor fraction	Estimated maximum occurrence fraction	Notes
imazamethabenz (Ref: AC 263840)	-	-	-

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 5000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Short term dietary NOEL	(mg kg⁻¹)	12.5	L2 L = Pesticide manuals and hard copy reference books / other sources 2 = Unverified data of unknown source Rat 2 yr	High
	(ppm diet)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		> 2150	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Anas platyrhynchos	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)		> 123	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Eisenia foetida	Moderate
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)	-	-	-
	Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 100	K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here ) 4 = Verified data	Low
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	-	-	-
	Chronic	-	-	-
	Notes	-
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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		> 100	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Oncorhynchus mykiss	Low
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		-	-	-
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		> 220	J4 J = Pesticide Action Network database (click here ) 4 = Verified data Daphnia magna	Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		78.1	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	Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		50	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Unknown species	Low
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	NOEAEC mg l⁻¹	-	-	-
Marine bivalves		-	-	-

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	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		2000	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rabbit	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		5.8	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
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	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 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 No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ?Possibly, status not identified XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser ✓Yes, known to cause a problem XNo, known not to cause a problem No data found Eye irritant Phototoxicant   ✓Yes, known to cause a problem No data found
General human health issues		May cause irreversible eye damage

Handling issues

Property	Value and interpretation
General	Prevent generation of mists Corrosive
CLP classification 2013	Not classified: Obsolete
WHO Classification	U (Unlikely to present an acute hazard)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	imazamethabenz-methyl
French	imazamethabenz
German	Imazamethabenz-methyl
Danish	imazamethabenz-methyl
Italian	imazamethabenz
Spanish	imazametabenz-metil
Greek	-
Polish	imazametabenz metylu
Swedish	-
Hungarian	-
Dutch	imazamethabenzmethyl
Norwegian	-

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Record last updated:	29/08/2024
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