Introduction：Basic information about Imazaquin acid CAS 81335-37-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Imazaquin acid Basic information
| Product Name: | Imazaquin acid |
| Synonyms: | IMAZAQUIN;imazaquin acid;2-(4-ISOPROPYL-4-METHYL-5-OXO-4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-QUINOLINE-3-CARBOXYLIC ACID;2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl)-3-quinolinecarboxylic acid;(+/-)-2-[4,5-DIHYDRO-4-METHYL-4-(1-METHYLETHYL)-5-OXO-1H-IMIDAZOL-2-YL]-3-QUINOLINECARBOXYLIC ACID;SCEPTER;SCEPTER(R);imazaquin (bsi,ansi,draft e-iso) |
| CAS: | 81335-37-7 |
| MF: | C17H17N3O3 |
| MW: | 311.34 |
| EINECS: | |
| Product Categories: | Alphabetic;Analytical Standards;Herbicides;Imidazolinone;IPesticides&Metabolites;Alpha sort;H-MAnalytical Standards;Pesticides&Metabolites |
| Mol File: | 81335-37-7.mol |
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Imazaquin acid Chemical Properties
| Melting point | 219-224°C |
| Boiling point | 451.38°C (rough estimate) |
| density | 1.1420 (rough estimate) |
| refractive index | 1.6500 (estimate) |
| storage temp. | 0-6°C |
| pka | 3.10±0.30(Predicted) |
| BRN | 5450078 |
| Major Application | agriculture
environmental |
| InChI | 1S/C17H17N3O3/c1-9(2)17(3)16(23)19-14(20-17)13-11(15(21)22)8-10-6-4-5-7-12(10)18-13/h4-9H,1-3H3,(H,21,22)(H,19,20,23) |
| InChIKey | CABMTIJINOIHOD-UHFFFAOYSA-N |
| SMILES | CC(C)C1(C)N=C(NC1=O)c2nc3ccccc3cc2C(O)=O |
| CAS DataBase Reference | 81335-37-7(CAS DataBase Reference) |
| EPA Substance Registry System | Imazaquin (81335-37-7) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 21 |
| Safety Statements | 36 |
| WGK Germany | 2 |
| RTECS | VB2009800 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal |
| Hazardous Substances Data | 81335-37-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 5000 mg/kg; LC50 (96 hr) in rainbow trout: 100 mg/l (Congleton) |
Imazaquin acid Usage And Synthesis
| Uses | Agricultural chemical. |
| Definition | ChEBI: 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid is a quinolinemonocarboxylic acid that is quinoline-3-carboxylic acid which is substituted by a 4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl group at position 2. It is a quinolinemonocarboxylic acid, an imidazolone and a monocarboxylic acid. |
| Hazard | Moderately toxic by ingestion and skin contact. Low toxicity by inhalation. |
| Pharmacology | Plant Metabolism. The selectivity of imazaquin is due todifferential rates and routes of metabolism in tolerantcrops versus susceptible weeds (3). The primarymetabolite in soybeans is a pyrroloquinoline acetamide(41, Fig. 18), which is immobile in the plant and is notan inhibitor of acetolactate synthase. This metabolite isfurther broken down to eventually yield a dicarboxylic acid.
Animal Metabolism. Metabolism studies in the ratshowed that they rapidly excreted unchanged imazaquinin the urine (5). There was no accumulation of imazaquin or any of its derivatives in the liver, kidney, muscle,fat, or blood. There was no detectable residue in theliver, kidney, muscle, or fat of lactating goats andlaying hens, which were fed imazaquin for 7 consecutivedays (5). |
| Metabolism | Imazaquin kills plants by inhibiting acetolactate synthase(ALS) (I50 = 1 μM), which is the first commonenzyme in the biosynthesis of the branched chain aminoacids, valine, leucine, and isoleucine. Imazaquin is rapidlyabsorbed through the roots of plants. Once it entersthe plant, imazaquin rapidly translocates to the growingpoints and growth ceases within 1 day after herbicideapplication followed by chlorosis and then necrosis of thegrowing points. Total plant death will occur within 2 to3 weeks after treatment. |
| Toxicity evaluation | Imazaquin has shown no mutagenic or genotoxic activity inthe Ames assay, mammalian cell gene mutation assay, invitro 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 forbioaccumulation in fish. |
Imazaquin acid Preparation Products And Raw materials
| Raw materials | Ammonium hydroxide-->Aniline-->Quinoline-->Dichloroethane-->2-N-BUTOXYETHYL METHACRYLATE-->3-Methyl-2-butanone-->Butyramide-->Tetrabutyl ammonium chloride-->2,3-dichlorobutyric acid |
