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imazapyr
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid

Supplier Sponsors

CAS Number: 81334-34-1Picture of molecule3D/inchi
Other(deleted CASRN):108224-78-8
FDA UNII: 787MX0M5A6
Nikkaji Web:J43.085D
Beilstein Number:5442754
MDL:MFCD00144470
XlogP3-AA:1.20 (est)
Molecular Weight:261.28115000
Formula:C13 H15 N3 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:herbicides / pesticides
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:White to tan powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 171.00 °C. @ 760.00 mm Hg
Vapor Pressure:1.790000 mmHg @ 25.00 °C. (est)
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): 0.220
Soluble in:
 water, 1.13E+04 mg/L @ 25 °C (exp)
 water, 650.3 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Imazapyr ≥95.0%
Odor: characteristic
Use: An insoluble herbicide which belongs to the imidazolinone family
Sigma-Aldrich
For experimental / research use only.
Imazapyr PESTANAL®, analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-duck LD50 > 2150 mg/kg
Pesticide Manual. Vol. 9, Pg. 487, 1991.

oral-mouse LD50 > 2000 mg/kg
Pesticide Manual. Vol. 9, Pg. 486, 1991.

oral-quail LD50 > 2150 mg/kg
Pesticide Manual. Vol. 9, Pg. 487, 1991.

oral-rat LD50 > 5000 mg/kg
Pesticide Manual. Vol. 9, Pg. 486, 1991.

Dermal Toxicity:
skin-rabbit LD50 > 2000 mg/kg
Pesticide Manual. Vol. 9, Pg. 486, 1991.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
herbicides / pesticides
Recommendation for imazapyr usage levels up to:
 not for fragrance use.
 
Recommendation for imazapyr flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Reasoned opinion on the setting of MRLs for imazapyr in genetically modified soya bean and other oilseeds and in lentils
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :54738
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid
Chemidplus:0081334341
RTECS:US5682500 for cas# 81334-34-1
 
References:
 2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):54738
Pubchem (sid):135013557
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C18864
HMDB (The Human Metabolome Database):Search
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•aqueous liquid with wetting agent •imazapyr is formulated as a liquid, a wettable powder (in water soluble bags only), and a granular. •soluble concentrate; granule; emulsifiable concentrate •mixtures: imazapyr + diuron •premix partners: s-metolachlor; fenoxaprop-p-ethyl; fluazifop-p-butyl; glyphosate •nupo6078 herbicide (nufarm americas inc.) imazapyr 27.6% •nufarm imazuron herbicide (nufarm americas inc.) diuron 62.22%, imazapyr 7.78% •arsenal herbicide technical (basf corporation) imazapyr 98.5% •topsite 2.5g herbicide (basf corporation) diuron 2%, imazapyr 0.5% •sahara dg herbicide (basf corporation) diuron 62.22%, imazapyr 7.78% •lightning herbicide (basf corporation) imazapyr 17.5%, imazethapyr 52.5% •lightning d herbicide (basf corporation) dicamba, sodium salt 58.9%, imazapyr 4%, imazethapyr 12% •arsenal 75 sg herbicide (basf corporation) imazapyr 75% •liquid lightning herbicide (basf corporation) imazapyr 5.05%, imazethapyr 15.15% •habitat release 75sg herbicide (basf corporation) imazapyr 75% •imazapyr technical (basf corporation) imazapyr 98% •dupont imazapyr technical (e. i. du pont de nemours and co., inc.) imazapyr 98.5% •dupont imazapyr 75xp herbicide (e. i. du pont de nemours and co., inc.) imazapyr 75% •dupont lineage hwc herbicide (e. i. du pont de nemours and co., inc.) sulfometuron methyl 28.1%, metsulfuron-methyl 7.5%, imazapyr 37.5% •dupont lineage clearstand herbicide (e. i. du pont de nemours and co., inc.) metsulfuron-methyl 9.5%, imazapyr 63.2% •dupont lineage prep herbicide (e. i. du pont de nemours and co., inc.) sulfometuron methyl 15.3%, metsulfuron-methyl 4.1%, imazapyr 54.5% •dupont viewpoint herbicide (e. i. du pont de nemours and co., inc.) metsulfuron-methyl 7.3%, imazapyr 31.6%, aminocyclopyrachlor 22.8% •eh 1135 pgr (pbigordon corp) mefluidide, diethanolamine salt 21.45%, imazapyr 0.15%, imazethapyr, ammonium salt 4.09% •kifix 70 dg herbicide (basf corporation) imazapyr 52.5%, imazapic 17.5% •imazapyr herbicide technical (agan chem mfg, ltd) imazapyr 96.1% •rainbow weed killer 4031 (rainbow technology corporation) diuron 2%, imazapyr 0.5% •topsite 2.5g herbicide (nufarm limited) diuron 2%, imazapyr 0.5% •ssi maxim arsenal 0.5g herbicide (nufarm limited) imazapyr 0.5% •ssi maxim arsenal 5g herbicide (nufarm limited) imazapyr 5% •imazapyr technical (makhteshim-agan of north america inc.) imazapyr 98% •polaris imazapyr technical (makhteshim-agan of north america inc.) imazapyr 98% •alligare mojave 70 eg bareground vegetation control (alligare, llc) diuron 62.22%, imazapyr 7.78% •amtide imazapyr technical 98% (amtide, llc) imazapyr 98.6% •tide imazapyr technical (tide international, usa, inc.) imazapyr 98.6%
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 arsenal
 arsenal 250A
2-(4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl)-3-pyridinecarboxylic acid
2-(4-methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid
 

Articles:

PubMed:Enantioselective effects of herbicide imazapyr on Arabidopsis thaliana.
PubMed:Evaluation of stem injection for managing giant reed (Arundo donax).
PubMed:Characterization of multiple-herbicide-resistant Italian ryegrass (Lolium perenne spp. multiflorum).
PubMed:Persistence and sorption of imazapyr in three Argentinean soils.
PubMed:Rethinking the composition of a rational antibiotic arsenal for the 21st century.
PubMed:Schistosomiasis chemotherapy.
PubMed:Differential expression of acetohydroxyacid synthase genes in sunflower plantlets and its response to imazapyr herbicide.
PubMed:Impact of the ahas transgene and of herbicides associated with the soybean crop on soil microbial communities.
PubMed:Development of transgenic imazapyr-tolerant cowpea (Vigna unguiculata).
PubMed:Root biomass response to foliar application of imazapyr for two imidazolinone tolerant alleles of sunflower (Helianthus annuus L.).
PubMed:Effects of the herbicide imazapyr on juvenile Oregon spotted frogs.
PubMed:Acetohydroxyacid synthase (AHAS) in vivo assay for screening imidazolinone-resistance in sunflower (Helianthus annuus L.).
PubMed:Comparability of imazapyr-resistant Arabidopsis created by transgenesis and mutagenesis.
PubMed:Effects of herbicides on Behr's metalmark butterfly, a surrogate species for the endangered butterfly, Lange's metalmark.
PubMed:Response to imazapyr and dominance relationships of two imidazolinone-tolerant alleles at the Ahasl1 locus of sunflower.
PubMed:Inheritance and molecular characterization of broad range tolerance to herbicides targeting acetohydroxyacid synthase in sunflower.
PubMed:Prospects for malaria elimination in non-Amazonian regions of Latin America.
PubMed:Acute toxicity of commonly used forestry herbicide mixtures to Ceriodaphnia dubia and Pimephales promelas.
PubMed:A minimal DNA cassette as a vector for genetic transformation of soybean (Glycine max).
PubMed:Potato (Solanum tuberosum) greenhouse tuber production as an assay for asexual reproduction effects from herbicides.
PubMed:Faster degradation of herbicidally-active enantiomer of imidazolinones in soils.
PubMed:Isolation, characterization of a strain capable of degrading imazethapyr and its use in degradation of the herbicide in soil.
PubMed:Soil-less bioassays for early screening for resistance to imazapyr in sunflower (Helianthus annuus L.).
PubMed:Improved extraction and clean-up of imidazolinone herbicides from soil solutions using different solid-phase sorbents.
PubMed:Crops with target-site herbicide resistance for Orobanche and Striga control.
PubMed:Effects of low concentrations of herbicides on full-season, field-grown potatoes.
PubMed:Molecular and biochemical characterization of an induced mutation conferring imidazolinone resistance in sunflower.
PubMed:Dissipation of four forest-use herbicides at high latitudes.
PubMed:Mineralization of herbicides imazapyr and imazaquin in aqueous medium by, fenton, photo-fenton and electro-fenton processes.
PubMed:Mutations of the ALS gene endowing resistance to ALS-inhibiting herbicides in Lolium rigidum populations.
PubMed:Biolistic-mediated genetic transformation of cowpea (Vigna unguiculata) and stable Mendelian inheritance of transgenes.
PubMed:Characterizing and designing polycation-clay nanocomposites as a basis for imazapyr controlled release formulations.
PubMed:Application of saturation transfer double difference NMR to elucidate the mechanistic interactions of pesticides with humic acid.
PubMed:High-efficiency transformation by biolistics of soybean, common bean and cotton transgenic plants.
PubMed:Abiotic degradation (photodegradation and hydrolysis) of imidazolinone herbicides.
PubMed:Comparative genotoxicity evaluation of imidazolinone herbicides in somatic cells of Drosophila melanogaster.
PubMed:CSR1, the sole target of imidazolinone herbicide in Arabidopsis thaliana.
PubMed:Test of APEX for nine forested watersheds in East Texas.
PubMed:Utilization and degradation of imazaquin by a naturally occurring isolate of Arthrobacter crystallopoietes.
PubMed:Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatography.
PubMed:Responses of enantioselective characteristics of imidazolinone herbicides and Chiralcel OJ column to temperature variations.
PubMed:Modelling the leaching of imazapyr in a railway embankment.
PubMed:Photochemical degradation of imazamox in aqueous solution: influence of metal ions and anionic species on the ultraviolet photolysis.
PubMed:High-performance liquid chromatographic separation of imidazolinone herbicide enantiomers and their methyl derivatives on polysaccharide-coated chiral stationary phases.
PubMed:Influence of metal salts on the photodegradation of imazapyr, an imidazolinone pesticide.
PubMed:Effectiveness of management interventions to control invasion by Rhododendron ponticum.
PubMed:Molecular characterization of true and ectopic gene targeting events at the acetolactate synthase gene in Arabidopsis.
PubMed:Biodegradation of imazapyr in typical soils in Zhejiang Province, China.
PubMed:Off-target herbicide deposition associated with treating individual trees.
PubMed:Poor competitive fitness of transgenically mitigated tobacco in competition with the wild type in a replacement series.
PubMed:Saltcedar control and water salvage on the Pecos river, Texas, 1999-2003.
PubMed:Biodegradation of imazapyr by free cells of Pseudomonas fluorescene biotype II and Bacillus cereus isolated from soil.
PubMed:Population dynamics of Digitaria spp submitted to selection pressure by herbicides in sugarcane crop.
PubMed:Imidazolinone-tolerant crops: history, current status and future.
PubMed:[Human health and pesticides used in the spraying of illicit crops: an issue of science or politics?].
PubMed:A comparative toxicologic and genotoxic study of the herbicide arsenal, its active ingredient imazapyr, and the surfactant nonylphenol ethoxylate.
PubMed:Use of imazapyr against Equisetum arvense on Swedish railway tracks.
PubMed:The fate of imazapyr in a Swedish railway embankment.
PubMed:Evaluation of resistance in Amaranthus quitensis Kunth populations to imazethapyr and other imidazolinones.
PubMed:Tandem constructs to mitigate transgene persistence: tobacco as a model.
PubMed:Cross-resistance pattern and alternative herbicides for Cyperus difformis resistant to sulfonylurea herbicides in Korea.
PubMed:Herbicide resistance in Aster squamatus conferred by a less sensitive form of acetolactate synthase.
PubMed:Sulfonylurea herbicide-resistant Monochoria vaginalis in Korean rice culture.
PubMed:Rapid, noninvasive screening for perturbations of metabolism and plant growth using chlorophyll fluorescence imaging.
PubMed:Effects of the herbicide imazapyr on benthic macroinvertebrates in a logged pond cypress dome.
PubMed:Transformation of carrots with mutant acetolactate synthase for Orobanche (broomrape) control.
PubMed:Cross-resistance to imidazolinone herbicides in chlorsulfuron-resistant Raphanus raphanistrum.
PubMed:A comparison between mouse and fish micronucleus test using cyclophosphamide, mitomycin C and various pesticides.
PubMed:Haptens and monoclonal antibodies for immunoassay of imidazolinone herbicides.
PubMed:Crystal structure of yeast acetohydroxyacid synthase: a target for herbicidal inhibitors.
PubMed:Evolution of herbicide resistance in weeds: initial frequency of target site-based resistance to acetolactate synthase-inhibiting herbicides in Lolium rigidum.
PubMed:Adsorption of imidazolinone herbicides on smectite-humic acid and smectite-ferrihydrite associations.
PubMed:Adsorption of imidazolinone herbicides on ferrihydrite-humic acid associations.
PubMed:Interaction of imidazolinone herbicides with soil humic acids. Experimental results and molecular modeling.
PubMed:Role of ferrihydrite in adsorption of three imidazolinone herbicides.
PubMed:Synthesis of dimethyl derivatives of imidazolinone herbicides: their use in efficient gas chromatographic methods for the determination of these herbicides.
PubMed:Residue analysis of imazapyr and chlozolinate in water using sunlight.
PubMed:Effect of mutagenesis at serine 653 of Arabidopsis thaliana acetohydroxyacid synthase on the sensitivity to imidazolinone and sulfonylurea herbicides.
PubMed:Capillary electrophoresis determinative and LC-MS confirmatory method for screening selected imidazolinone herbicides from soil.
PubMed:Acute poisoning with a herbicide containing imazapyr (Arsenal): a report of six cases.
PubMed:Development of a method based on liquid chromatography-electrospray mass spectrometry for analyzing imidazolinone herbicides in environmental water at part-per-trillion levels.
PubMed:Simultaneous determination of imidazolinone herbicides from soil and natural waters using soil column extraction and off-line solid-phase extraction followed by liquid chromatography with UV detection or liquid chromatography/electrospray mass spectroscopy.
PubMed:Expression, purification and characterization of Arabidopsis thaliana acetohydroxyacid synthase.
PubMed:Use of ELISA immunoassay kits as a complement to HPLC analysis of imazapyr and triclopyr in water samples from forest watersheds.
PubMed:Metabolism of twelve herbicides by Streptomyces.
PubMed:Inheritance and mechanism of resistance to herbicides inhibiting acetolactate synthase in Sonchus oleraceus L.
PubMed:A double mutant allele, csr1-4, of Arabidopsis thaliana encodes an acetolactate synthase with altered kinetics.
PubMed:Intragenic recombination in the CSR1 locus of Arabidopsis.
PubMed:Persistence and leaching of the herbicide imazapyr in soil.
PubMed:Resistance to Acetolactate Synthase-Inhibiting Herbicides in Annual Ryegrass (Lolium rigidum) Involves at Least Two Mechanisms.
PubMed:High-performance liquid chromatographic determination of the herbicide imazapyr residues in water and soil.
PubMed:Forest worker exposure to airborne herbicide residues in smoke from prescribed fires in the southern United States.
PubMed:Molecular Basis of Imidazolinone Herbicide Resistance in Arabidopsis thaliana var Columbia.
PubMed:Lack of Cross-Resistance of Imidazolinone-Resistant Cell Lines of Datura innoxia P. Mill. to Chlorsulfuron : Evidence for Separable Sites of Action on the Target Enzyme.
PubMed:A Mutation Causing Imidazolinone Resistance Maps to the Csr1 Locus of Arabidopsis thaliana.
PubMed:Acetolactate Synthase Activity in Developing Maize (Zea mays L.) Kernels.
PubMed:Imidazolinones and acetohydroxyacid synthase from higher plants: properties of the enzyme from maize suspension culture cells and evidence for the binding of imazapyr to acetohydroxyacid synthase in vivo.
 
Notes:
None found
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