Imazethapyr

Basic Info

Common NameImazethapyr(F06068)
2D Structure
FRCD IDF06068
CAS Number81335-77-5
PubChem CID54740
FormulaC15H19N3O3
IUPAC Name

5-ethyl-2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid

InChI Key

XVOKUMIPKHGGTN-UHFFFAOYSA-N

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)

Canonical SMILES

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

Isomeric SMILES

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

Synonyms
        
            Pivot
        
            5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid
        
            IMAZETHAPYR
        
            81335-77-5
        
            Pursuit
        
            Imazethapyr [ANSI:BSI:ISO]
        
            HSDB 6678
        
            EPA Pesticide Chemical Code 128922
        
            Imazethapyr aqueous solution
        
            CL 263499
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAlpha-amino acid or derivatives - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Imidazolyl carboxylic acid derivative - Imidazolinone - Pyridine - 2-imidazoline - Heteroaromatic compound - Azacycle - Organoheterocyclic compound - Carboxylic acid amidine - Carboxylic acid - Monocarboxylic acid or derivatives - Amidine - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organonitrogen compound - Organooxygen compound - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Properties

Property NameProperty Value
Molecular Weight289.335
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Complexity475
Monoisotopic Mass289.143
Exact Mass289.143
XLogP2
Formal Charge0
Heavy Atom Count21
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.6483
Human Intestinal AbsorptionHIA+0.9704
Caco-2 PermeabilityCaco2-0.6390
P-glycoprotein SubstrateSubstrate0.5000
P-glycoprotein InhibitorNon-inhibitor0.8441
Non-inhibitor0.8747
Renal Organic Cation TransporterNon-inhibitor0.9404
Distribution
Subcellular localizationMitochondria0.8110
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7441
CYP450 2D6 SubstrateNon-substrate0.8217
CYP450 3A4 SubstrateNon-substrate0.6397
CYP450 1A2 InhibitorNon-inhibitor0.6796
CYP450 2C9 InhibitorNon-inhibitor0.8095
CYP450 2D6 InhibitorNon-inhibitor0.8910
CYP450 2C19 InhibitorNon-inhibitor0.6682
CYP450 3A4 InhibitorNon-inhibitor0.7300
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8429
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9986
Non-inhibitor0.9481
AMES ToxicityNon AMES toxic0.7428
CarcinogensNon-carcinogens0.7344
Fish ToxicityLow FHMT0.5829
Tetrahymena Pyriformis ToxicityHigh TPT0.9142
Honey Bee ToxicityLow HBT0.8835
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7782
Carcinogenicity (Three-class)Non-required0.6142
Model Value Unit
Absorption
Aqueous solubility-3.2859LogS
Caco-2 Permeability0.5376LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7938LD50, mol/kg
Fish Toxicity1.8825pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4287pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PeanutsAustralia0.1mg/kg
MaizeAustralia0.05mg/kg
Soybean OilIndia0.1mg/kg
PeasIsrael0.01mg/kg
Kidney BeansCanada0.1mg/kg
Lima BeansCanada0.1mg/kg
Navy BeansCanada0.1mg/kg
Pinto BeansCanada0.1mg/kg
Runner BeansCanada0.1mg/kg
Snap BeansCanada0.1mg/kg
SoybeansCanada0.1mg/kg
Tepary BeansCanada0.1mg/kg
Wax BeansCanada0.1mg/kg
PeasCanada0.1mg/kg
Fenugreek SeedsCanada0.05mg/kg
Rapeseeds (Canola)Canada0.05mg/kg
Dry Adzuki BeansCanada0.1mg/kg
Dry Black BeansCanada0.1mg/kg
Dry Cranberry BeansCanada0.1mg/kg
Dry Dutch Brown BeansCanada0.1mg/kg

References

TitleJournalDatePubmed ID
Organomineral Interactions and Herbicide Sorption in Brazilian Tropical andSubtropical Oxisols under No-Tillage.J Agric Food Chem2016 May 2526666375
Effects of the Herbicide Imazethapyr on Photosynthesis in PGR5- and NDH-DeficientArabidopsis thaliana at the Biochemical, Transcriptomic, and Proteomic Levels.J Agric Food Chem2016 Jun 827215288
Imazethapyr and imazapic, bispyribac-sodium and penoxsulam: zooplankton anddissipation in subtropical rice paddy water.Sci Total Environ2015 May 125659307
Analyzing Arabidopsis thaliana root proteome provides insights into the molecular bases of enantioselective imazethapyr toxicity.Sci Rep2015 Jul 826153126
Trace concentrations of imazethapyr (IM) affect floral organs development andreproduction in Arabidopsis thaliana: IM-induced inhibition of key genesregulating anther and pollen biosynthesis.Ecotoxicology2015 Jan25348600
Are Nutrient Stresses Associated with Enantioselectivity of the Chiral Herbicide Imazethapyr in Arabidopsis thaliana?J Agric Food Chem2015 Dec 226566036
The impact of herbicide-resistant rice technology on phenotypic diversity andpopulation structure of United States weedy rice.Plant Physiol2014 Nov25122473
Physiological and molecular basis of acetolactate synthase-inhibiting herbicideresistance in barnyardgrass (Echinochloa crus-galli).J Agric Food Chem2013 Jan 1623237199
Imazethapyr enantioselectively affects chlorophyll synthesis and photosynthesis in Arabidopsis thaliana.J Agric Food Chem2013 Feb 1323343119
Leaching of three imidazolinone herbicides during sprinkler irrigation.J Environ Qual2012 May-Jun22565269
Role of exogenously supplied ferulic and p-coumaric acids in mimicking the modeof action of acetolactate synthase inhibiting herbicides.J Agric Food Chem2011 Sep 2821870840
Transgenic sugar beet tolerant to imidazolinone obtained byAgrobacterium-mediated transformation.Tsitol Genet2011 May-Jun21774399
Faster degradation of herbicidally-active enantiomer of imidazolinones in soils.Chemosphere2010 May20416927
Sorption characteristics of atrazine and imazethapyr in soils of new zealand:importance of independently determined sorption data.J Agric Food Chem2009 Nov 2519874020
Enantioselectivity in the phytotoxicity of herbicide imazethapyr.J Agric Food Chem2009 Feb 2519199589
Cross-resistance to herbicides of five ALS-inhibiting groups and sequencing ofthe ALS gene in Cyperus difformis L.J Agric Food Chem2009 Feb 2519191488
Nitrogen assimilation studies using 15N in soybean plants treated withimazethapyr, an inhibitor of branched-chain amino acid biosynthesis.J Agric Food Chem2006 Nov 1517090128
Imazethapyr aqueous photolysis, reaction quantum yield, and hydroxyl radical rateconstant.J Agric Food Chem2006 Apr 516569055
The residual effect of imazethapyr applied in soybean to barley and winter wheat in Romania.Commun Agric Appl Biol Sci200617390828
Adsorption of pesticides from water by functionalized organobentonites.J Agric Food Chem2005 Sep 2116159179