55814-41-0

Basic information

• Product Name: Mepronil
• Synonyms: 2-methyl-n-(3-(1-methylethoxy)phenyl)-benzamid;b1-2459;Benzamide, 2-methyl-N-(3-(1-methylethoxy)phenyl)-;kco-1;N-(3-Isopropoxyphenyl)-2-methylbenzamide;BASITAC;BASITAC(R);MEPRONIL
• CAS NO: 55814-41-0
• Molecular Formula: C₁₇H₁₉NO₂
• Molecular Weight: 269.34
• Product Categories: FUNGICIDE
• Mol File: 55814-41-0.mol

Chemical Properties

• Melting Point: 84-89°C
• Boiling Point: 412.48°C (rough estimate)
• Flash Point: 159.7 °C
• Appearance: White viscous liquid with slight pungent odour
• Density: 1.0483 (rough estimate)
• Vapor Pressure: 8.56E-05mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Very Slightly)
• PKA: 13.10±0.70(Predicted)
• Water Solubility: 12 mg l-1(20 °C)
• BRN: 2381749
• CAS DataBase Reference: Mepronil(CAS DataBase Reference)
• NIST Chemistry Reference: Mepronil(55814-41-0)
• EPA Substance Registry System: Mepronil(55814-41-0)

Safety Data

• WGK Germany: 2
• RTECS: CV5581700
• Hazardous Substances Data: 55814-41-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Mepronil is used as a fungicide for controlling Basidiomycetes diseases in various crops such as rice, cereals, potatoes, vegetables, sugar beet, fruit, vines, tobacco, turf grass, and other crops. It helps in preventing the growth and spread of fungal infections, ensuring a healthy yield and crop protection.
Used in Herbal Medicine:
Mepronil is also utilized in the raw materials of herbal medicine, where it serves as a fungicidal agent to protect plants from diseases and promote their overall health. Its presence in herbal medicine ingredients highlights its potential for use in a broader range of applications beyond traditional agriculture.

Metabolic pathway

Mepronil is an analogue of flutolanil containing a 2-methyl group as opposed to the 2-trifluoromethyl group. The compounds have the same mode of action and are metabolised via similar routes except that the methyl group of mepronil provides an extra site for metabolic attack. The compound is metabolised by dealkylation and hydroxylation at both the methyl and isopropyl groups and by aryl hydroxylation. Some hydrolysis occurs in plants and animals.

Degradation

Mepronil is stable to light, heat and air and in solution over a pH range of 3-10. It is hydrolysed under strongly alkaline conditions (PM). Mepronil on a silica gel surface exposed to sunlight between September and December (Japan) was 66% degraded with an estimated half-life of 36 days. This could be shortened by the addition of the photosensitiser xanthone (Yumita and Yamamoto, 1982). Irradiation of an aqueous solution with UV light at 30 °C afforded 32% degradation in 80 hours. 14C-Aniline and 14C-carbonyl labelling was used in these experiments. Carbonyl label afforded marpally more metabolites, indicating that some amide bond cleavage occurred. Twelve photo-products were identified and four unknowns were detected. Aqueous photolysis afforded somewhat fewer products than the surface irradiation. Hydroxylation occurred initially at four positions in the molecule and these were followed by further oxidation, hydrolysis, cyclisation or cleavage. The products are shown in Scheme 1. The major products (5-10%) of surface photolysis were compounds 2, 3 and 4 and on aqueous photolysis were 6 and 13 with an unknown derived only from carbonyl labelling.

InChI:InChI=1/C17H19NO2/c1-12(2)20-15-9-6-8-14(11-15)18-17(19)16-10-5-4-7-13(16)3/h4-12H,1-3H3,(H,18,19)

Upstream product

• 64-17-5 ethanol 
• 942-13-2 isopropyl 2-methylbenzoate 
• 41406-00-2 3-isopropoxyaniline 
• 118-90-1 ortho-methylbenzoic acid 
• 88991-53-1 3-(1-Methylethoxy)nitrobenzene 
• 87-24-1 ethyl 2-methylbenzoate 
• 55814-53-4 3'-hydroxy-2-methylbenzanilide 
• 75-26-3 isopropyl bromide 

Downstream Products

• 64922-09-4 N-(Dichloro-fluoro-methylsulfanyl)-N-(3-isopropoxy-phenyl)-2-methyl-benzamide 
• 1449384-36-4 N-cyclopropyl-N-(3-isopropoxyphenyl)-2-methylbenzamide 

Relevant articles and documents

Direct Amidation of Carboxylic Acids with Nitroarenes

N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.

Chromium-Catalyzed Activation of Acyl C-O Bonds with Magnesium for Amidation of Esters with Nitroarenes

Here, we report a chromium-catalyzed activation of acyl C-O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

Process for producing 2-alkylbenzanilide

2-Alkylbenzanilide is produced by reacting an alkyl 2-alkylbenzoate having the formula STR1 wherein X represents a lower alkyl group and R represents a lower alkyl group with an aniline having the formula STR2 wherein Y represents hydrogen atom, an alkoxy

Compositions and methods of combatting bacteria and fungi using 2-methylbenzanilide derivatives

An agricultural germicide having the formula SPC1 Wherein R represents C1-12 alkyl, alkenyl, alkynyl, benzyl or chlorobenzyl.