3′-Isopropoxy-2-methylbenzanilide

ChEBI: A member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-methylbenzoic acid with the amino group of 3-(ispropyloxy)aniline. A fungicide used to control diseases caused by Basidomycetes including Rhizoctonia

Mepronil is a member of the class of benzamides, obtained by formal condensation of the carboxy group of 2-methylbenzoic acid with the amino group of 3-(ispropyloxy)aniline. A fungicide used to control diseases caused by Basidomycetes including Rhizoctonia and Puccinia spp. It has a role as an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor and an antifungal agrochemical. It is a member of benzamides, an aromatic ether and a benzanilide fungicide.

Preparation Method One: Preparation of N-Acetyl-M-aminophenol 25g (0.23mol) m-aminophenol, 18.0g (0.30mol) acetic acid, 25g (0.264mol) acetic anhydride and 25mL water were mixed, stirred and dissolved, and heated in an oil bath for 1h , Cooled to 5℃, filtered, washed with water, and dried to obtain 23g of product with a yield of 66.5%. Preparation of N-acetyl m-isopropoxyaniline 30.2g (0.2mol) N-acetyl m-aminophenol, 4.8g (0.22mol) sodium hydroxide and 100mL of ethanol were mixed, stirred and dissolved, then added 32.0g ( 0.26mol) isopropyl bromide, heated to reflux for 5h, placed to room temperature, filtered to remove solid sodium bromide, distilled off 80% ethanol, cooled and filtered to obtain 38g of product, yield 98%. Preparation of m-isopropoxyaniline 38.6g (0.2mol) N-acetyl m-isopropoxyaniline, a certain amount of 35% hydrochloric acid and 200mL water were mixed, heated in an oil bath, and reacted at 100～110℃ for 2h. Then neutralize with 30% sodium hydroxide aqueous solution to neutrality, separate the oil layer, the water layer is taken with ether benzene, the oil layers are combined, dried with magnesium sulfate, the ether is distilled off, and then distilled under reduced pressure to obtain the product 25.5g, yield 85% . The preparation of o-toluoyl chloride involves the reaction of o-toluoic acid with chlorinated sulfoxyl chloride to produce o-toluoyl chloride. This process is mature. Synthesis of rust inhibitors 15.1g (0.1mol) of m-isopropoxyaniline, 120mL of acetone and 4.2g (0.05mol) of sodium carbonate were mixed, cooled to -5 to -3°C with stirring, and 15.5g was slowly added dropwise (0.1mol) o-Toluoyl chloride, react at 0℃ for 2h, filter to remove sodium chloride, distill acetone from mother liquor, wash with water, recrystallize and dry to obtain 26g of product. The yield was 96.37%. Preparation method Preparation of di-amino amino component Nitrobenzene is sulfonated by fuming sulfuric acid, then neutralized to generate sodium meta-nitrobenzenesulfonate, reduced to sodium meta-aminobenzenesulfonate, and then alkali-melted and acidified to generate meta-amino group phenol. Preparation of 2-methyl-N-(3'-hydroxyphenyl)benzamide In the presence of phosphorus trichloride, o-methylbenzoic acid is reacted with m-aminophenol dry benzene solvent to obtain 2-methyl- N-(3'-hydroxyphenyl)benzamide. Synthesis of rust inhibitors 2-methyl-N-(3'-hydroxyphenyl)benzamide and 2-chloropropane are reacted in sodium hydroxide methanol solution to prepare rust inhibitors. 

Mepronil is an benzanilide based fungicide found in the raw materials of herbal medicine.

Molecular Weight:269.34
XLogP3:3.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:269.141578849
Monoisotopic Mass:269.141578849
Topological Polar Surface Area:38.3
Heavy Atom Count:20
Complexity:316
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes