2008-58-4

Usage

Uses

Used in Herbicide Industry:
2,6-Dichlorobenzamide is used as a metabolite in the herbicide industry for its role in the degradation process of herbicides. It is derived from the herbicide 2,6-Dichlorobenzonitrile (D431945), which is employed to control the growth of unwanted plants in various agricultural and horticultural applications. The presence of 2,6-Dichlorobenzamide as a metabolite indicates the persistence and potential environmental impact of the herbicide in question.

Metabolic pathway

Oral doses of DCB are excreted by rats as DCB, two monohydroxy-DCBs, 2-chloro-5-hydroxy-6- (methylthio)benzamide, and 2-chloro-5-hydroxy-6-[S- (N-acetyl)-cysteinyl]benzamide. Biliary excretion (33% of the dose), enterohepatic circulation, and intestinal microfloral metabolism are involved in the formation of 2-chloro-5-hydroxy-6-(methylthio)benzamide. The major route for the metabolism of DCB is the conjugation with glutathione in a process involving phenyl ring hydroxylation at the ortho position to the S-glutathionyl moiety. Two mechanisms can be processed for the formation of hydroxylated metabolites resulting from the epoxidation at the 2- and 3-positions of the phenyl ring (for the proposed mechanisms: see the text).

InChI:InChI=1/C7H5Cl2NO/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H2,10,11)

Upstream product

• 1194-65-6 2,6-dichloro-benzonitrile 
• 4659-45-4 2,6-Dichlorobenzoyl chloride 
• 7722-84-1 dihydrogen peroxide 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 144-55-8 sodium hydrogencarbonate 
• 6575-28-6 (1E)-2,6-dichlorobenzaldehyde oxime 
• 118-69-4 2,6-dichlorotoluene 
• 55-21-0 benzamide 
• 15258-73-8 2,6-dichlorobenzyl alcohol 
• 50-30-6 2,6-dichlorobenzoic acid 
• 6575-25-3 1,3-dichloro-2-ethynyl-benzene 
• 19393-92-1 1-bromo-2,6-dichlorobenzene 
• 3019-71-4 Trichloroacetyl isocyanate 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 35377-49-2 2,6-dichlorobenzoyl isocyanate 
• 35409-97-3 N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-urea 
• 35372-56-6 N-(2,6-dichlorobenzoyl)-N'-(4-fluorophenyl)urea 
• 35366-75-7 1-(2,6-Dichloro-benzoyl)-3-(3-fluoro-phenyl)-urea 
• 116800-83-0 N-(Bis-methylsulfanyl-methylene)-2,6-dichloro-benzamide 
• 119448-94-1 (2,6-Dichloro-benzoyl)-dithiocarbamic acid methyl ester 
• 50822-24-7 1-(2,6-Dichloro-benzoyl)-3-(2-trifluoromethyl-phenyl)-urea 
• 608-31-1 2,6-Dichloroaniline 
• 960249-95-0 1,1-dimethylethyl [(2.6-dichlorophenyl)carbonyl]carbamate 
• 92207-23-3 1-(2,6-dichlorobenzoyl)-3-(2,4,6-trichlorophenyl)-urea 
• 67048-60-6 3-(2,6-dichloro-phenyl)-isothiazole-4-carboxylic acid ethyl ester 
• 67048-84-4 3-(2,6-dichloro-phenyl)-isothiazole-4,5-dicarboxylic acid 
• 67048-68-4 3-(2,6-dichloro-phenyl)-isothiazole-4,5-dicarboxylic acid dimethyl ester 
• 19547-33-2 3-(2,6-dichloro-phenyl)-isothiazole-4-carboxylic acid 

Relevant academic research and scientific papers

A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides

Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.

Acid-promoted palladium(II)-catalyzed ortho-halogenation of primary benzamides: En route to halo-arenes

Br?nsted acid-promoted palladium(II)-catalyzed regioselective installation of halogens (Br, Cl, and I) to the aromatic ring of benzamide derivatives has been achieved using primary amides. A wide variety of benzamides were compatible under established conditions to afford the halogenated products without installing any external auxiliary. Mild reaction conditions, use of primary amide as a directing group, external additive-free conditions, and gram-scale reaction are some appealing features of this protocol. Detailed experimental results revealed that Br?nsted acid plays a critical role in this transformation.

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.

A halogenated benzamide compound preparation method (by machine translation)

The invention discloses a halogenated benzamide compound preparation method. The preparation method, comprises the following steps: adding the hydrogen peroxide to type I compounds, water and alkali are mixed to obtain a mixed solution of, shown in the following reaction; wherein X is halogen, n is 1, 2, 3, 4 or 5; states the type I compound charging capacity of at least 8 g, the hydrogen peroxide and the formula I compound in a molar ratio of 1:1 - 1.6: 1; the hydrogen peroxide addition time is 2 - 10 and H. The invention for the preparation of the water as the reaction solvent, to avoid the use of organic solvent, and in reducing the amount on the basis of raw materials, can still reach the higher yield and the product quality is good, the operation is simple, three wastes, economic effect is high, and is suitable for industrial production. (by machine translation)

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.

Ferric perchlorate-mediated one-step reaction of [60]fullerene with primary amides for the synthesis of fullerooxazoles

The facile one-step reaction of [60]fullerene with primary amides promoted by cheap and easily available ferric perchlorate afforded a series of interesting fullerooxazole derivatives. The reaction was tolerant of a large variety of primary amides containing aryl, alkyl, and cinnamyl groups. A possible reaction mechanism for product formation was proposed.

Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide

To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.

Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety

A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.

Silica-sulfuric acid: Novel, simple, efficient and reusable catalyst for hydration of nitrile to amide

Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatography method and characterized by 1H NMR, 13C NMR and mass spectral analysis.