Imazamethabenz-methyl (Ref: AC 222293)	Last updated: 11/02/2021
(Also known as: imazamethabenz, methyl variant; CL 222293)

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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; 1998, first registered 1988

UK regulatory status

UK COPR regulatory status	Not approved
Date COPR inclusion expires	Expired
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	UK
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

Also used in

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 group	Imidazolinone
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	-
CIPAC number	529
US EPA chemical code	128842
PubChem CID	54744
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 Classification (HRAC)	B
Herbicide Resistance Classification (WSSA)	2
Insecticide Resistance Classification (IRAC)	Not applicable
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Avena fatua, Alopecurus myosuroides
Physical state	Off-white powder

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Assert
Example products using this active	BASF Nufarm Americas Inc.
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 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		291000	C4 C = AGRITOX (click here ) 4 = Verified data Acetone	-
		135000	C4 C = AGRITOX (click here ) 4 = Verified data Chloroform	-
		57500	C4 C = AGRITOX (click here ) 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 (click here ) 4 = Verified data	Low
Bulk 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. MS in preparation 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 (click here ) 4 = Verified data	Non-volatile
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 4 = Verified data	Moderately persistent
	DT₅₀ (lab at 20 °C)	47	K4 K = Research datasets, e.g. Pandora, Demetra 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 on plant matrix	Value	-	-	-
	Note	-
Dissipation rate RL₅₀ on and in plant matrix	Value	-	-	-
	Note	-
Aqueous photolysis DT₅₀ (days) at pH 7	Value	36	K4 K = Research datasets, e.g. Pandora, Demetra 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 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 4 = Verified data	Moderately fast

Soil adsorption and mobility

Property		Value	Source; quality score; and other information	Interpretation
Linear	Kd	-	H3 H = The US ARS pesticide properties database (click here ) 3 = Unverified data of known source	Mobile
	Koc	35
	Notes and range	Other sources: 51 mL g⁻¹ (DW3)
Freundlich	Kf	-	-	-
	Kfoc	-
	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	-

Key metabolites

Metabolite	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
imazamethabenz (Ref: AC 263840)	Soil	-	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	Low risk	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source Based on LogP < 3	Low risk
	CT₅₀ (days)	-		-
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 year	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)		-	-	-
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
Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		> 220	J4 J = Pesticide Action Network database (click here ) 4 = Verified data Daphnia magna	Low
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)		-	-	-
Non-target plants		-	-	-
		-	-	-
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 (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 internet resources 2 = Unverified data of unknown source Unknown species	Low
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 4 = Verified data	Low
	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 pollinators (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other pollinators (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
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)		-	-	-
Other soil macro-organisms	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Other arthropod (1)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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	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)		0.0625	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
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
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

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
EC Risk Classification	Xi - Irritant: R36 N - Dangerous for the environment: R50
EC Safety Classification	-
WHO Classification	U (Unlikely to present an acute hazard)
UN Number	-
Waste disposal & packaging	-

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

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Record last updated:	11/02/2021
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