24691-80-3

Usage

Uses

Used in Agricultural Industry:
Fenfuram is used as a seed-treatment fungicide for the control of bunts and smuts in cereals. Its application helps protect crops from these fungal diseases, ensuring better yield and quality of the harvested grains.
Used in Fungicide Production:
Fenfuram is utilized in the production of fungicides due to its succinate dehydrogenase inhibitory properties. This characteristic allows it to effectively combat fungal infections in various crops, making it a valuable component in the development of agricultural chemicals.

InChI:InChI=1/C12H11NO2/c1-9-11(7-8-15-9)12(14)13-10-5-3-2-4-6-10/h2-8H,1H3,(H,13,14)

Upstream product

• 5555-00-0 2-methylfuran-3-carbonyl chloride 
• 62-53-3 aniline 
• 6141-58-8 methyl 2-methyl-3-furancarboxylate 
• 7429-90-5 aluminium 
• 93-98-1 N-phenyl benzoyl amide 

Downstream Products

• 1449384-35-3 N-cyclopropyl-2-methyl-N-phenylfuran-3-carboxamide 
• 5612-67-9 2-methyl-furan-3-carboxaldehyde 
• 79190-45-7 acide β-(methyl-2 furyl)-3 acrylique 
• 79190-43-5 2-Methyl-N-phenyl-furan-3-carboximidoyl chloride 

Relevant academic research and scientific papers

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Manganese Catalyzed Direct Amidation of Esters with Amines

The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.

Methyl Esters as Cross-Coupling Electrophiles: Direct Synthesis of Amide Bonds

Amide bond formation and transition metal-catalyzed cross-coupling are two of the most frequently used chemical reactions in organic synthesis. Recently, an overlap between these two reaction families was identified when Pd and Ni catalysts were demonstrated to cleave the strong C-O bond present in esters via oxidative addition. When simple methyl and ethyl esters are used, this transformation provides a powerful alternative to classical amide bond formations, which commonly feature stoichiometric activating agents. Thus far, few redox-active catalysts have been demonstrated to activate the C(acyl)-O bond of alkyl esters, which makes it difficult to perform informed screening when a challenging reaction needs optimization. We demonstrate that Ni catalysts bearing diverse NHC, phosphine, and nitrogen-containing ligands can all be used to activate methyl esters and enable their use in direct amide bond formation.

Nickel-Catalyzed Amide Bond Formation from Methyl Esters

Despite being one of the most important and frequently run chemical reactions, the synthesis of amide bonds is accomplished primarily by wasteful methods that proceed by stoichiometric activation of one of the starting materials. We report a nickel-catalyzed procedure that can enable diverse amides to be synthesized from abundant methyl ester starting materials, producing only volatile alcohol as a stoichiometric waste product. In contrast to acid- and base-mediated amidations, the reaction is proposed to proceed by a neutral cross coupling-type mechanism, opening up new opportunities for direct, efficient, chemoselective synthesis.

Fungicidal composition for seed dressing

The present invention relates to a fungicidal composition intended for the protection of the multiplication products of cultivated plants, containing: (a) 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol; (b) one or more fungicides suitable for the protection of the said multiplication products, optionally one or more insecticides, (c), an agriculturally acceptable inert vehicle and an agriculturally acceptable surfactant. The invention also relates to a method for protecting the multiplication products of plants against fungal diseases using these compositions.

Transformation thermique des β-(methyl-2 furyl)-3 acryloylazides: Nouveau mode de formation de certaines pyrimidines

In boiling diphenyl ether, β-3-(2-methylfuryl)acryloylazides were not transformed to the expected furopyridones according to the Eloy and Deryckere reaction but 5-substituted pyrimidine-2,4-diones, generated by dimerization of vinyl isocyanates issued from Curtius reaarangement of the starting material, were obtained.

Process for the manufacture of a furancarboxylic acid anilide

A process for the manufacture of furancarboxylic acid anilides of the general formula STR1 in which R1 represents an aryl group or an alkyl group, R2 and R3 each represent an alkyl group or hydrogen, by a ring-closure reaction of a β-ketoester with an α-haloaldehyde or α-haloketone, in the presence of a stoichiometric amount of a halide-binding substance to form a furancarboxylic acid ester, and by subsequent anilidation, the reaction being performed in two stages, the ring-closure reaction being carried out in the presence of a mixture of alkaline earth metal carbonates and pyridine in a ratio of from 1000 to 5:1 Val, based on the hydrohalic acid liberated, at temperatures between 50° and 100° C.; and after separation in said second stage, the furancarboxylic ester is reacted while stirring with aniline in up to 20 times molecular excess, in the presence of equimolar amounts based on the furancarboxylic acid, of magnesium dianilide and/or aluminum trianilide in liquid phase or in suspension at temperatures between 20° and 180° C., under normal pressure. The furancarboxylic acid anilides have an outstanding pesticidal action.

Fungicidal dispersions of carboxylic acid amides

Fungicidal dispersions comprising a carboxylic acid amide, other than pyracarbolide, as the fungicidally-active ingredient and an aluminum chelate of a polynuclear hydroxy-quinone as a crystal growth stabilizer, dispersed in a paraffinic mineral oil, a liquid triglyceride, or a liquid ester formed between a C1 -C12 monoalcohol and a C2 -C10 mono- or di-carboxylic acid.