Imazaquin

Imazaquin is an imidazolinone herbicide which inhibits acetohydroxy acid synthase (AHAS). Imazaquin displays high mobility in soils[1].

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.

Preparation method-Preparation of 2-amino-2,3-dimethylbutyronitrile Dissolve 61.36g of sodium cyanide and 79g of ammonium chloride in 400mL of 28% ammonia water, and add 1mol of methyl isopropyl ketone dropwise at room temperature. After stirring overnight, the oil layer was separated, the water layer was extracted with dichloromethane, the oil layers were combined, dried, and desolventized to obtain the product. The yield is 90%, and the purity is 94%-95.9%. Preparation of 2-amino-2,3-dimethylbutyramide Add 0.1mol 2-amino-2,3-dimethylbutyronitrile dropwise to 29.7mL of concentrated sulfuric acid under cooling at a temperature below 25°C, and then slowly raise the temperature to 100 Incubate the reaction at ℃ for 1 hour to hydrolyze the cyano group, and then add 85 mL of concentrated ammonium hydroxide below 75 ℃ to generate 2-amino-2,3-dimethylbutanamide. After extraction with dichloroethane, the organic phase was dried, concentrated and recrystallized to obtain 0.091 mol of amide with a yield of 91%. Preparation of quinoline-2,3-dicarboxylic acid Dissolve 0.01mol 2,3-dichlorobutyric acid diethyl ester in chlorobenzene, add equimolar aniline, 3.6g 33% sodium hydroxide, 0.14g tetrabutyl chloride Ammonium was stirred for 2h at 75～80℃, cooled and separated. The organic phase was dissolved in 0.0046mol of the corresponding diethyl ester, and the yield was 46%. Dissolve 0.02mol of the diethyl ester in 40mL of toluene, add it to the Vilsmeier reagent at room temperature, then heat to reflux for 2h, pour the reaction solution into 60mL of water, separate the layers, detoluene the organic layer, and recrystallize the residue to obtain 0.0148mol of quinone Diethyl phenoline-2,3-dioxate with a yield of 74%, hydrolyzed under alkaline conditions to obtain quinoline-2,3-dicarboxylic acid with a yield of 98%. Vilsmeier test preparation: 0.03mol of dimethylformamide is dissolved in 12mL of toluene, and 0.03mol of phosphorus trichloride is dripped at 20～30℃, and the Vilsmeier reagent is prepared by incubating and stirring for 60 minutes. The preparation of quinoline-2,3-dicarboxylic acid anhydride is prepared by intramolecular dehydration of quinoline-2,3-dicarboxylic acid, and the dehydrating agent is phosgene or acetic anhydride. Synthesis of imidazolinic acid Dissolve 40g 2-amino-2,3-dimethylbutyramide in 500mL acetonitrile, add 60g quinoline-2,3-dicarboxylic anhydride, react at 50～60℃ for 2h, and cool to The solid was filtered out after room temperature. This solid was dissolved in 435 mL of 1.5 mol/L sodium hydroxide solution and heated at 80-85° C. for 2 h to obtain 49 g of imidazolinic acid with a yield of 82%. Preparation method Diimidazolinic acid can also be obtained by one-step reaction of 2-methylquinoline with elemental sulfur and 2-amino-2,3-dimethylbutanamide to obtain the corresponding 2-imidazolidinyl derivative, and then the After the role of base lithium, it reacts with carbon dioxide to prepare imidazoquinoline acid. This process route shortens the reaction process and has potential application value.

Herbicides that control most annual and perennial grasses and broad-leaved weeds

Molecular Weight:311.33
XLogP3:2.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:311.12699141
Monoisotopic Mass:311.12699141
Topological Polar Surface Area:91.6
Heavy Atom Count:23
Complexity:545
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes