41643-35-0

Basic information

• Product Name: NAPROPAMIDE
• Synonyms: (R)-N,N-Diethyl-2-(1-naphthalenyloxy)propanamide;(R)-napropamide
• CAS NO: 41643-35-0
• Molecular Formula: C17H21NO2
• Molecular Weight: 271.35
• Mol File: 41643-35-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: NAPROPAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NAPROPAMIDE(41643-35-0)
• EPA Substance Registry System: NAPROPAMIDE(41643-35-0)

Safety Data

• Hazardous Substances Data: 41643-35-0(Hazardous Substances Data)

Usage

Description

NAPROPAMIDE, also known as Napropamide M, is an amide chiral herbicide specifically designed for the control of noxious weeds that cause significant yield losses in agricultural produce. It is the (R)-enantiomer of N,N-diethyl-2-(naphthalen-1-yloxy)propanamide, which contributes to its effectiveness in targeting and eliminating unwanted weeds.

Uses

Used in Agricultural Industry:
NAPROPAMIDE is used as a herbicide for controlling the growth of noxious weeds, such as Echinochloa crus-galli, which are known to cause substantial yield losses in agricultural produce. Its chiral amide structure allows for targeted action against these weeds without causing harm to the desired crops, making it a valuable tool in maintaining agricultural productivity and ensuring a stable food supply.

Upstream product

• 90-15-3 α-naphthol 
• 15299-99-7 Napropamide 

Relevant articles and documents

Enantioseparation of napropamide by supercritical fluid chromatography: Effects of the chromatographic conditions and separation mechanism

Supercritical fluid chromatography (SFC) is already used for enantioseparation in the pharmaceutical industry, but it is rarely used for the separation of chiral pesticides. Comparing with high performence liquid chromatography, SFC uses much more environmnetal friendly and economic mobile phase, supercritical CO2. In our work, the enantioseparation of an amide herbicide, napropamide, using three different polysaccharide-type chiral stationary phases (CSPs) in SFC was investigated. By studying the effect of different CSPs, organic modifiers, temperature, back-pressure regulator pressures, and flow rates for the enantioseparation of napropamide, we established a rapid and green method for enantioseparation that takes less than 2?minutes: The column was CEL2, the mobile phase was CO2 with 20% 2-propanol, and the flow rate was 2.0?mL/min. We found that CEL2 demonstrated the strongest resolution capability. Acetonitrile was favored over alcoholic solvents when the CSP was amylose and 2-propanol was the best choice when using cellulose. When the concentration of the modifiers or the flow rate was decreased, resolutions and analysis times increased concurrently. The temperature and back-pressure regulator pressure exhibited only minor influences on the resolution and analysis time of the napropamide enantioseparations with these chiral columns. The molecular docking analysis provided a deeper insight into the interactions between the enantiomers and the CSPs at the atomic level and partly explained the reason for the different elution orders using the different chiral columns.

Enantioselective Catabolism of Napropamide Chiral Enantiomers in Sphingobium sp. A1 and B2

Napropamide [N,N-diethyl-2-(1-naphthalenyloxy)propenamide, NAP] is a highly efficient and broad-spectrum amide herbicide. Little is known about the bacterial catabolism of its different enantiomers. Here, we report the isolation of two NAP-degrading strains of Sphingobium sp., A1 and B2, and the different catabolic pathways of different enantiomers in these two strains. Strain A1 dioxygenated NAP at different positions of the naphthalene ring of different enantiomers, leading to the complete degradation of R-NAP while producing a dead-end product from S-NAP. Strain B2 cleaved the amido bonds of both enantiomers, but only the product from S-NAP could be further transformed to form α-naphthol and mineralize in strain B2. The degradation rates of R-NAP and S-NAP in the combination degradation by strains A1 and B2 were 24.8 and 7.5 times that in the single-strain degradation by strain B2 or A1, respectively, showing enhanced synergistic catabolism between strains A1 and B2. This study provides new insights into the enantioselective catabolic network of the chiral herbicide NAP in microorganisms.

METHOD FOR THE MANUFACTURE OF N, N-DIALLKYLLACTAMIDE

The invention relates to a method for the manufacture of N,N-dialkyllactamide, whereby at least one of the compounds selected from the series consisting of alkyl lactate, lactide and polylactic acid is mixed with dialkylamine in order to form a reaction mixture, under conditions whereby aminolysis takes place in the reaction mixture. The method is characterized in that the reaction mixture further comprises a Lewis acid. As a result of the invented method, N,N-dialkyllactamides can be manufactured in high yields and with high optical purity.