160171-18-6

Usage

InChI:InChI=1/C14H16Cl3NO2/c1-4-14(3,12(19)7-15)18-13(20)9-5-10(16)8(2)11(17)6-9/h5-6H,4,7H2,1-3H3,(H,18,20)

Upstream product

• 113485-46-4 3,5-dichloro-4-methylbenzoyl chloride 
• 209809-70-1 2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyl-5-methyleneoxazoline 
• 87-90-1 trichloroisocyanuric acid 
• 39652-34-1 3,5-dichloro-4-methylbenzoic acid 
• 156052-68-5 zoxamide 
• 118725-00-1 methyl (R)-2-amino-2-methyl-butyrate hydrochloride 
• 3059-97-0 (2R)-2-amino-2-methylbutanoic acid 
• 92760-72-0 L-isovalin methyl ester hydrochloride 
• 595-40-4 L-isovaline 

Relevant academic research and scientific papers

A systematic evaluation of zoxamide at enantiomeric level

Zoxamide is a recently discovered chiral fungicide that applied to agricultural production, but the potential environmental risk may be underestimated because the risk posed by either enantiomer has not been adequately assessed. Therefore, systemic evaluation of zoxamide was first carried out at the enantiomeric level. Enantioselective bioactivity against target pathogens (Phytophthora capsici Leonian, Alternaria solani, Botryis cinerea, Colletotrichum gloeosprioides Penz, Phytophthora sojae Kaufmann & Gerdemann) was explored, and the order of the bioactivity was R-zoxamide > Rac-zoxamide > S-zoxamide, with a 9.9- to 140.0-times difference between two enantiomers. Molecular docking simulation was utilized to clarify the mechanism underlying the observed differences in enantioselective bioactivity, and the result indicated that a difference of Van der waals force between R/S-zoxamide and the specific receptor gave rise to the different antifungal activity. The enantioselective toxicity result demonstrated that R-zoxamide had 4.9- to 10.8- times greater acute toxicity to Selenastrum capricornutum and Daphnia magna than S-zoxamide. S-zoxamide degraded faster under aerobic condition in all three types of soils, giving rise to an enrichment of high-risk R-enantiomer. Under anaerobic condition, however, no significant difference in dissipation rate was observed between two enantiomers. R-zoxamide was 1.5- to 3.5-times more bioactive and 1.1- to 1.5-times more toxic than Rac-zoxamide, which means developing R-zoxamide instead of racemate is a potential way to reduce pesticide dosage without loss of efficacy against target organisms and that an inactive isomer would no more be released to the environment. This study may have implications for better practical application and environmental risk assessment of zoxamide enantiomers.

Method for preparing benzamide compound

The invention provides a method for preparing a benzamide compound, and belongs to the technical field of organic synthesis. The method for preparing a benzamide compound provided by the invention comprises the following steps: mixing aryl-substituted dihydrooxazole, an acidic catalyst, water and a reaction solvent, and carrying out hydrolysis ring-opening reaction to obtain the benzamide compound, wherein the acidic catalyst is p-toluenesulfonic acid or sulfonic acid ion exchange resin. According to the invention, p-toluenesulfonic acid or sulfonic acid ion exchange resin is used as an acidiccatalyst, under the catalytic action of the p-toluenesulfonic acid or sulfonic acid ion exchange resin, aryl-substituted dihydrooxazole is subjected to hydrolysis ring-opening reaction to obtain thebenzamide compound, only metered toluenesulfonic acid or sulfonic acid ion exchange resin needs to be catalyzed, the toluenesulfonic acid or sulfonic acid ion exchange resin is convenient to remove after the reaction is completed, almost no waste is generated, and industrial production is convenient to achieve.

Enantiomer mixture and preparation method and application thereof

The invention provides an enantiomer mixture and a preparation method and application thereof, and belongs to the technical field of pesticide chemistry and organic synthesis. The enantiomer mixture is a mixture of S-zoxamide and R-zoxamide, and the enant

N-acetonylbenzamide fungicides

This invention relates to new compositions comprising predominantly one enantiomer of an N-acetonylbenzamide fungicide, methods of preparing N-acetonylbenzamides, and their use as fungicides.

Process for the manufacture of acetonylbenzamides

Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.

Method for controlling resistant fungi

A method for controlling phytopathogenic fungi is disclosed. The method uses a fungicidal composition which has been found to be effective against strains of fungi which are resistant to benzimidazole fungicides. When combined with one or more of benzimidazole, thiophanate, or dicarboximide fungicides, and applied to a mixed population of sensitive and resistant fungi, the fungicidal compound of the present invention is more effective against the mixed population of fungi than either of the fungicidal compounds alone.

Development of a process for triazine-promoted amidation of carboxylic acids

A process has been developed for the triazine-promoted amidation of carboxylic acids. We have identified 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) as a cost-effective reagent for this transformation. The procedure is a suitable alternative to traditional amidation processes when an acid chloride cannot be prepared from the corresponding carboxylic acid due to safety, stability, or handling concerns.

Metal salt catalyzed process to oxazolines and subsequent formation of chloroketones

This invention relates to a process for the preparation of an α-chloroketone compound comprising the steps of (i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline (ii) chlorinating the 5-methyleneoxazoline using trichloroisocyanuric acid to produce a chlorinated oxazoline intermediate and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene, R is a hydrogen atom or alkyl, and R1and R2are each independently an alkyl or substituted alkyl group, or R1and R2together with the carbon atom to which they are attached form a cyclic structure. Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.

N-acetonylbenzamide fungicides

This invention relates to new compositions comprising predominantly one enantiomer of an N-acetonylbenzamide fungicide, methods of preparing N-acetonylbenzamides, and their use as fungicides.

Process for the manufacture of acetonylbenzamides

Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.