Imazamox

Base Information

• Chemical Name: Imazamox
• CAS No.: 114311-32-9
• Deprecated CAS: 182636-13-1
• Molecular Formula: C15H19N3O4
• Molecular Weight: 305.334
• European Community (EC) Number: 601-305-7
• UNII: UG6793ON5F
• DSSTox Substance ID: DTXSID3034664
• Nikkaji Number: J897.210I
• Wikidata: Q17166948
• ChEMBL ID: CHEMBL1881028
• Mol file: 114311-32-9.mol

Synonyms:imazamox

Chemical Property of Imazamox

Chemical Property:

• Melting Point: 166-167°C
• Refractive Index: 1.602
• PKA: pK1 2.3; pK2 3.3(at 25℃)
• PSA: 100.88000
• Density: 1.31 g/cm³
• LogP: 0.98170
• Storage Temp.: 0-6°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 305.13755610
• Heavy Atom Count: 22
• Complexity: 491

Purity/Quality:

95%TC, ^*data from raw suppliers

Raptor ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Imidazolinone
• Canonical SMILES: CC(C)C1(C(=O)NC(=N1)C2=C(C=C(C=N2)COC)C(=O)O)C
• Description: Imazamox (2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5- (methoxymethyl)-3-pyridinecarboxylic acid) is a systemic herbicide that moves throughout the plant tissue and prevents plants from producing a necessary enzyme, acetolactate synthase (ALS), which is not found in animals. Susceptible plants will stop growing soon after treatment, but plant death and decomposition will occur over several weeks. Imazamox is used for the control of vegetation in and around aquatic sites and terrestrial non-crop sites. It is herbicidally active on many submerged, emergent, and floating broadleaf and monocot aquatic plants in and around standing and slow- moving water bodies. It is used as herbicide on sunflower seed, alfalfa, oilseed rape and soya bean seed and used for the control of most annual and perennial broadleaf weeds and grasses, woody species, and riparian and emergent aquatic weed species. Imazamox is only moderately persistent, and it degrades aerobically in the soil to a non-herbicidal metabolite which is immobile or moderately mobile. Imazamox also degrades by aqueous photolysis. Imazamox is registered throughout the world for use in leguminous crops, including soybeans, alfalfa, and edible beans, as well as in imidazolinone-resistant crops (9). A nonionic surfactant or oil adjuvant is required for maximum activity. Imazamox is much more active when applied post-emergent to the weeds compared with pre-emergence application (9). One difference between imazamox and other imidazolinones is the much shorter interval needed before sensitive follow crops can be planted. This difference is due to the more rapid degradation of imazamox in the soil compared with other imidazolinones.
• Uses: Imazamox is an imidazolinone based acetolactate synthase inhibitor that is utilized as a herbicide for weed control. Herbicide.

Technology Process of Imazamox

There total 6 articles about Imazamox which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methanol (67-56-1) + 2-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]-5-chloromethyl nicotinic acid (124523-81-5) → imazamox (114311-32-9)

Guidance literature:

methanol; 2-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]-5-chloromethyl nicotinic acid; With sodium hydroxide; In water; at 65 ℃; for 1.5h;

With sulfuric acid; In water; pH=4;

Reference yield:

C15H19N3O4 → imazamox (114311-32-9)

Guidance literature:

With dihydrogen peroxide;

Reference yield:

diethyl 5-(methoxymethyl)-2,3-pyridinedicarboxylate → imazamox (114311-32-9)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / pentan-1-ol; water / 1 h / 90 °C

2: picoline; acetic anhydride / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / 75 °C

3: 30 °C / pH 4

4: dihydrogen peroxide

With picoline; dihydrogen peroxide; acetic anhydride; sodium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; pentan-1-ol; water;

upstream raw materials:

methanol

2-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]-5-chloromethyl nicotinic acid

5-(methoxymethyl)-2,3-pyridinedicarboxylic acid

Downstream raw materials:

C₇H₆O₃*C₁₅H₁₉N₃O₄

Refernces

• 1、 -. "2-[(1-CYANOPROPYL)CARBAMOYL]-5-CHLOROMETHYL NICOTINIC ACIDS AND THE USE THEREOF IN MANUFACTURING HERBICIDAL IMIDAZOLINONES". Page/Page column 13. . Retrieved 2010/06/15.
• 2、 -. "Method for Controlling Rust Infections in Leguminous Plants". . . Retrieved 2009/06/27.