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Imazethapyr (Ref: AC 252925)
Last updated: 11/02/2021
(Also known as: CL 252925)
GENERAL INFORMATION
Description
A herbicide used to control a variety of broad-leaved weeds and grasses in numerous crops
Example pests controlled
Barnyardgrass, Crabgrass, Cocklebur, Pigweeds, Stinkweed Nightshade, Wild mustard, Velvetleaf, Foxtail, Morning-glory
Example applications
Soybeans; Peanuts; Beans and peas
Efficacy & activity
-
Availability status
Current
Introduction & key dates
1989
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
-
Date EC 1107/2009 inclusion expires
Expired
EU Candidate for substitution (CfS)
-
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
Australia, USA
Chemical structure
Isomerism
A chiral molecule existing in the R- and S-forms, the R-isomer is considered to be the most biologically active.
Chemical formula
C₁₅H₁₉N₃O₃
Canonical SMILES
CCC1=CN=C(C(=C1)C(=O)O)C2=NC(C(=O)N2)(C)C(C)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
XVOKUMIPKHGGTN-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C15H19N3O3/c1-5-9-6-10(13(19)20)11(16-7-9)12-17-14(21)15(4,18-12)8(2)3/h6-8H,5H2,1-4H3,(H,19,20)(H,17,18,21)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
imazethapyr -
General status
Pesticide type
Herbicide
Substance group
Imidazolinone
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Systemic with contact and residual activity. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS.
CAS RN
81335-77-5
EC number
-
CIPAC number
700
US EPA chemical code
128922
PubChem CID
54740
Molecular mass
289.33
PIN (Preferred Identification Name)
-
IUPAC name
5-ethyl-2-[(RS)-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]nicotinic acid
CAS name
2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-5-ethyl-3-pyridinecarboxylic acid
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
Many recorded cases, Amaranthus hybridus, Amaranthus lividus, Amaranthus palmeri
Physical state
Colourless crystals
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Clearpath
  • Newpath
  • Pivot
  • Pursuit
  • Overtop
Example products using this active
  • AgroCare
  • BASF: Makhteshim Agan Group
  • KingTai Chemicals Co.
Formulation and application details
Usually supplied as an aqueous concentrate
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
1400
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
48200
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone		 -
105000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
5000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene		 -
900
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Heptane		 -
Melting point (°C)
171
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
Decomposes before boiling
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Degradation point (°C)
180
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
3.09 X 1001 Calculated -
Log P
1.49
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Low
Bulk density (g ml⁻¹)
1.11
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
2.1
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 -
pKa(2) 3.9
Vapour pressure at 20 °C (mPa)
1.33 X 10-02
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.30 X 10-02
Z2 Z = Kingtai Chemials website (click here )
2 = Unverified data of unknown source
 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)
90
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
 Moderately persistent
DT₅₀ (lab at 20 °C)
513
B3 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
3 = Unverified data of known source
 Very persistent
DT₅₀ (field)
51
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Lab studies DT₅₀ range 126-900 days, field studies DT₅₀ range 14-290 days Northern USA and 7-19 days southern USA
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ on and in plant matrix
Value
15.2
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
Note
Published literature RL₅₀ range 6.5-32.1 days, 6 field crops, various matrices, n=6
Aqueous photolysis DT₅₀ (days) at pH 7
Value
52
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Stable
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Stable
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
 Mobile
Koc
52
Notes and range
UK PSD lab studies 20-22 mL g⁻¹ silt loam soils; Other sources: 100 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
3.90 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
9.67 X 10-01 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Mobile Calculated -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
1.6
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
Viscera		 Low potential
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Rat		 Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
818
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Rat		 Moderate
(ppm diet)
10000 -
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)
> 340
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Oncorhynchus mykiss		 Low
Fish - Chronic 21 day NOEC (mg l⁻¹)
97.0
P4 P = Other governments and regulators
4 = Verified data
Pimephales promelas		 Low
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 1000
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Daphnia magna		 Low
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
103.0
P3 P = Other governments and regulators
3 = Unverified data of known source
Daphnia magna		 Low
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)
0.008
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
Lemna gibba		 High
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
71
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
Raphidocelis subcapitata		 Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 100
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
> 24.6
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderate
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)
10000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
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
B5 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
5 = Verified data used for regulatory purposes
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)
3.27
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)
0.44
B4 B = UK CRD and ACP evaluation documents / and other Defra (UK) documents (click here )
4 = Verified data
UK ACP 1999		 -
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
;
B3 B = DNA damage/repair (EFSA database)
3 = Negative
;
C3 C = Gene mutation (EFSA database)
3 = Negative
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
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
✓Yes, known to cause a problem
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
Prevent generation of dust
Corrosive
CLP classification 2013
Environment: H400, H410
EC Risk Classification
Xn - Harmful: R21/22
Xi - Irritant: R36/38
N - Dangerous for the environment: R52
EC Safety Classification
-
WHO Classification
U (Unlikely to present an acute hazard)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
imazethapyr
French
imazethapyr
German
Imazethapyr
Danish
imazethapyr
Italian
imazetapir
Spanish
imazetapir
Greek
-
Polish
imazetapyr
Swedish
-
Hungarian
-
Dutch
-
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