Introduction：Basic information about Imazapyr acid CAS 81334-34-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Imazapyr acid Basic information
| Product Name: | Imazapyr acid |
| Synonyms: | AC 252925;CL 252925;2-(4-Methyl-5-oxo-4-propan-2-yl-1H-imidazol-2-yl)pyridine-3-carboxylic acid;Arsenal 250A;Charper;2-(5-Oxo-4-methyl-4-isopropyl-1H-imidazole-2-yl)pyridine-3-carboxylic acid;AC-243997;Imazapyr Standard |
| CAS: | 81334-34-1 |
| MF: | C13H15N3O3 |
| MW: | 261.28 |
| EINECS: | 617-219-8 |
| Product Categories: | Pesticides intermediate;Analytical Standards;Alpha sort;Alphabetic;Herbicides;H-MAnalytical Standards;Imidazolinone;IPesticides&Metabolites;Pesticides&Metabolites |
| Mol File: | 81334-34-1.mol |
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Imazapyr acid Chemical Properties
| Melting point | 169-173°C |
| Boiling point | 404.53°C (rough estimate) |
| density | 1.1923 (rough estimate) |
| vapor pressure | 0-0Pa at 20-25℃ |
| refractive index | 1.5600 (estimate) |
| storage temp. | 0-6°C |
| pka | 1.9, 3.6(at 25℃) |
| BRN | 5442754 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | agriculture
environmental |
| InChI | InChI=1S/C13H15N3O3/c1-7(2)13(3)12(19)15-10(16-13)9-8(11(17)18)5-4-6-14-9/h4-7H,1-3H3,(H,17,18)(H,15,16,19) |
| InChIKey | CLQMBPJKHLGMQK-UHFFFAOYSA-N |
| SMILES | C1(C2NC(=O)C(C)(C(C)C)N=2)=NC=CC=C1C(O)=O |
| LogP | -3.97-0.04 at 20℃ and pH3-9.9 |
| Dissociation constant | 1.7-11.1 at 20℃ |
| CAS DataBase Reference | 81334-34-1(CAS DataBase Reference) |
| EPA Substance Registry System | Imazapyr (81334-34-1) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36-52/53 |
| Safety Statements | 26-61 |
| WGK Germany | 2 |
| RTECS | US5682500 |
| HS Code | 29333990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 |
| Hazardous Substances Data | 81334-34-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: >5000 mg/kg; dermally in rabbits: >2000 mg/kg (Paxman) |
Imazapyr acid Usage And Synthesis
| Chemical Properties | solid |
| Uses | Imazapyr is an analytical standard used for proteomics research. |
| Definition | ChEBI: 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid is a pyridinemonocarboxylic acid that is nicotinic acid which is substituted at position 2 by a 4,5-dihydro-imidazol-2-yl group, which in turn is substituted at positions 4, 4, and 5 by isopropyl, ethyl, and oxo groups, respectively. It is a member of pyridines, a member of imidazolines, an imidazolone and a pyridinemonocarboxylic acid. |
| Pharmacology | Imazapyr kills plants by inhibiting acetolactate synthase(ALS) (I50 = 5 μM), which is the first common enzyme inthe biosynthesis of the branched chain amino acids, valine,leucine, and isoleucine. Imazapyr is rapidly absorbedthrough the leaves of plants. Once it enters the plant,imazapyr rapidly translocates to the growing points andgrowth ceases within 1 day after herbicide applicationfollowed by chlorosis and then necrosis of the growingpoints. Total plant death will occur within 2 to 3 weeksafter treatment. |
| Environmental Fate | Imazapyr is weakly to moderately adsorbed on sandy loamand silt loam soils. The Freundlich adsorption coefficient ranges from 0 to 7.8 (15). Because imazapyr is a weak acidand exists in different ionic states, soil pH has an effect onsoil binding properties. The anionic form predominates atsoil pH as low as 5.5, and this form bindsweakly to soil. Theneutral or molecular form is important at soil pH from 4to 6.5. This form binds to soil organic matter and clay. Thecationic form is important at pH less than 4. Because thesoil is a heterogeneous mixture of acid and base chemicalgroups, there may be sites within a particular soil that are2 to 3 pH units higher or lower than the average pH. Thecationic form will bind tightly to the lower pH components.Because of these interactions, small decreases in pH below 6 will result in large increases in binding. The half-life ofimazapyr in the soil is 25–142 d (14). Imazapyr remainsin the top 30 cm of the soil with low leaching potential.The degradation route of imazapyr in the soil has not beendetermined. |
| Metabolism | Plant Metabolism. The selectivity of imazapyr is due todifferential rates and routes of metabolism in tolerantcrops versus susceptible weeds (3). The half-lifeof imazapyr in tolerant crops has not been accuratelydetermined. The metabolic route of imazapyr is not clear.The parent compound can be metabolized to a tricycliccompound (33, Fig. 15) in some species, but the primarymetabolite is an imidazopyrrolo-pyridine derivative (34,Fig. 15). This compound does not inhibit acetolactatesynthase, the target site for the imidazolinones, and itis immobile in the plant (4).
Animal Metabolism. Metabolism studies in the ratshowed that imazapyr is rapidly excreted in the urine (5).There was no accumulation of imazapyr or any of itsderivatives in the liver, kidney, muscle, fat, or blood. |
| Toxicity evaluation | Imazapyr has shown no mutagenic or genotoxic activityin the Ames assay, mammalian cell gene mutation assay,in vitro chromosome aberration assay, in vitro unscheduledDNA synthesis (URS) assay, or the in vivo dominantlethal assay in male rats.This herbicide also has a low potential for bioaccumulationin fish. |
Imazapyr acid Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Tetrahydrofuran-->Diethyl oxalate-->Sodium ethoxide-->4-Methylpyridine-->3-METHOXYPROPIONIC ACID-->Diethyl oxalacetate-->Diethyl succinate-->L-ASPARTIC ACID-->2-Ethylacrylaldehyde-->2-Amino-2,3-dimethylbutyronitrile |
