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Details

Stereochemistry RACEMIC
Molecular Formula C15H19N3O3
Molecular Weight 289.3297
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMAZETHAPYR

SMILES

CCC1=CN=C(C2=NC(C)(C(C)C)C(=O)N2)C(=C1)C(O)=O

InChI

InChIKey=XVOKUMIPKHGGTN-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Imazethapyr is an imidazole compound used as a selective herbicide. It is applied preplant incorporated, preemergence, at cracking, and postemergence. The compound controls weeds by reducing the levels of three branched-chain aliphatic amino acids, isoleucine, leucine and valine, through the inhibition of aceto-hydroxyacid synthase, an enzyme common to the biosynthetic pathway for these amino acids. This inhibition causes a disruption in protein synthesis which, in turn, leads to an interference in DNA synthesis and cell growth. The compound is used to control grasses and broadleaved weeds including barnyardgrass, crabgrass, cocklebur, panicums, pigweeds, nightshade, mustard, smartweed, velvetleaf, jimsonweed, foxtails, seedling johnsongrass, lambsquarters, morningglory and others. Tolerant crops include soybeans, peanuts, dry and edible beans, peas, alfalfa and imidazolinone resistant/tolerant corn. Additional research is being conducted on other leguminous crops. Acetolactate synthase inhibition is the primary mechanism of action of imazethapyr (IM).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.353 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Atrial fibrillation and mortality among patients with acute coronary syndromes without ST-segment elevation: results from the PURSUIT trial.
2001-07-01
CM can play critical role in reducing medical errors.
2001-07
A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies.
2001-07
Strategy for identifying biomarkers of aging in long-lived species.
2001-07
Smallest region of overlapping deletion in 1p36 in human neuroblastoma: a 1 Mbp cosmid and PAC contig.
2001-07
Full face rejuvenation in three dimensions: a "face-lifting" for the new millennium.
2001-06-27
How to help your staff strengthen customer service: a do-able approach.
2001-06-08
Differential sensorimotor processing of vestibulo-ocular signals during rotation and translation.
2001-06-01
Slowing of voluntary and involuntary saccades: an early sign in spinocerebellar ataxia type 7.
2001-06
On determining the relationship between blood alcohol concentration and smooth pursuit eye movements.
2001-06
Optimal smoothing in visual motion perception.
2001-06
Adaptive changes in dynamic properties of human disparity-induced vergence.
2001-06
Cortical input to the nucleus of the optic tract and dorsal terminal nucleus (NOT-DTN) in macaques: a retrograde tracing study.
2001-06
Cancellation of self-induced retinal image motion during smooth pursuit eye movements.
2001-06
An fMRI study of anticipation and learning of smooth pursuit eye movements in humans.
2001-05-25
From knowing what to knowing where: modeling object-based attention with feedback disinhibition of activation.
2001-05-15
Reconstruction of target speed for the guidance of pursuit eye movements.
2001-05-01
Do people make environments or do environments make people?
2001-05
Effects of one night of sleep deprivation on hormone profiles and performance efficiency.
2001-05
The human TINF2 gene organisation and chromosomal localization.
2001-05
Biomechanics of the cervical spine Part 3: minor injuries.
2001-05
Sensorimotor integration compensates for visual localization errors during smooth pursuit eye movements.
2001-05
Development of potent truncated glucagon antagonists.
2001-04-26
Poor performance in smooth pursuit and antisaccadic eye-movement tasks in healthy siblings of patients with schizophrenia.
2001-04-15
[Glutaminergic hypothesis of schizophrenia: clinical research studies with ketamine].
2001-04-11
Effect of lipid-lowering therapy on early mortality after acute coronary syndromes: an observational study.
2001-04-07
Performance of time-frequency representation techniques to measure blood flow turbulence with pulsed-wave Doppler ultrasound.
2001-04
The effects of litigation on symptom expression: a prospective study following mild traumatic brain injury.
2001-04
From computing with numbers to computing with words. From manipulation of measurements to manipulation of perceptions.
2001-04
Developing the knowledge base of family practice.
2001-04
Letting the cat out of the bag.
2001-04
Sorption of ametryn and imazethapyr in twenty-five soils from Pakistan and Australia.
2001-03
Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations.
2001-03
Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling.
2001-03
Which duration of postsaccadic slowing identifies anticipatory saccades during smooth pursuit eye movements?
2001-03
[Treatment of refractory cardiac failure by resynchronization].
2001-03
Why are some people happier than others? The role of cognitive and motivational processes in well-being.
2001-03
Role of ferrihydrite in adsorption of three imidazolinone herbicides.
2001-03
How employees respond to personal offense: the effects of blame attribution, victim status, and offender status on revenge and reconciliation in the workplace.
2001-02
Visual fields and foraging in procellariiform seabirds: sensory aspects of dietary segregation.
2001-01
Assessment of the risk of fall, related to visual stimulation, in patients with central vestibular disorders.
2001-01
Adaptive data acquisition in MRI.
2001-01
Ecosystem approaches to human health.
2001
Decreases in blood perfusion of the anterior cingulate gyri in Anorexia Nervosa Restricters assessed by SPECT image analysis.
2001
New Zealand pathologists: a case study in occupational control.
2001
Life, liberty, the pursuit of happiness,... and health care?
2001
The flash-lag phenomenon: object motion and eye movements.
2001
Using decision tree induction to model oculomotor data.
2001
Compulsive checking behavior of quinpirole-sensitized rats as an animal model of Obsessive-Compulsive Disorder(OCD): form and control.
2001
Conversion therapy revisited: parameters and rationale for ethical care.
2001
Patents

Sample Use Guides

The acute oral LD50 for technical imazethapyr was reported to be >5000 mg/kg for rats.
Route of Administration: Oral
At the highest concentration of 25 mg/L, in vitro acetolactate synthase (ALS) activity was almost completely inhibited by S-(+)-, R-(-)-Imazethapyr and (+/-)-Imazethapyr, there was only 1.1 times differences between S-(+)- and R-(-)-Imazethapyr.
Name Type Language
FABIAN
Preferred Name English
IMAZETHAPYR
HSDB   ISO   MI  
Common Name English
AC-263499
Code English
PURSUIT
Brand Name English
5-ETHYL-2-(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2-YL) NICOTINIC ACID
Systematic Name English
5-ETHYL-2(4-ISOPROPYL-4-METHYL-5-OXO-2-IMIDAZOLIN-2- YL)NICOTINIC ACID, (RS)-
Systematic Name English
IMAZETHAPYR [HSDB]
Common Name English
2-(4,5-DIHYDRO-4-METHYL-4(1-METHYLETHYL)-5-OXO-1H- IMIDAZOL-2YL)-5-ETHYL-3-PYRIDINECARBOXYLIC ACID, (±)-
Systematic Name English
CL-263499
Code English
IMAZETHAPYR, (±)-
Systematic Name English
IMAZETHAPYR [ISO]
Common Name English
IMAZETHAPYR [MI]
Common Name English
3-PYRIDINECARBOXYLIC ACID, 2-(4,5-DIHYDRO-4-METHYL-4-(1- METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL)-5-ETHYL-
Systematic Name English
2-(4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL- 2-YL)-5-ETHYL-3-PYRIDINECARBOXYLIC ACID
Systematic Name English
PIVOT
Brand Name English
3-PYRIDINECARBOXYLIC ACID, 2-(4,5-DIHYDRO-4-METHYL-4-(1- METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL)-5-ETHYL-, (±)-
Systematic Name English
5-ETHYL-2-(4-ISOPROPYL-4-METHYL-5-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL)NICOTINIC ACID, (±)-
Systematic Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 128922
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
Code System Code Type Description
FDA UNII
72T2IN94I4
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID3024287
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY
CAS
81335-77-5
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY
HSDB
6678
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY
ALANWOOD
imazethapyr
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY
MERCK INDEX
m6218
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY Merck Index
PUBCHEM
54740
Created by admin on Mon Mar 31 22:20:52 GMT 2025 , Edited by admin on Mon Mar 31 22:20:52 GMT 2025
PRIMARY