Napropamide

Napropamide Basic information
Product Name:Napropamide
Synonyms:2-(1-naphthyloxy)-n,n-diethylpropionamide;2-(alpha-naphthoxy)-n,n-diaethyl-propionsaeureamid;2-(alpha-Naphthoxy)-N,N-Diethylpropionamide;Devrinol T;N,N-diethyl-2-(1-naphthalenyloxy)-Propanamide;n,n-diethyl-2-(1-naphthalenyloxy)propionamide;2-(A-NAPHTHOXY)-N,N-DIETHYL PROPIONAMIDE;Napropamide (25%)
CAS:15299-99-7
MF:C17H21NO2
MW:271.35
EINECS:239-333-3
Product Categories:DA - DH;Amides;HERBICIDE;Carbonyl Compounds;Organic Building Blocks;Alphabetic;D
Mol File:15299-99-7.mol
Napropamide Structure
Napropamide Chemical Properties
Melting point 73-78 °C (lit.)
Boiling point 414.44°C (rough estimate)
density 1.0288 (rough estimate)
refractive index 1.5675 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly), Methanol (Sparingly)
pka-0.82±0.70(Predicted)
form Solid
color Brown
Water Solubility 73mg/L(20 ºC)
Merck 13,6442
BRN 6809160
LogP3.360
CAS DataBase Reference15299-99-7(CAS DataBase Reference)
NIST Chemistry ReferenceNapropamide(15299-99-7)
EPA Substance Registry SystemNapropamide (15299-99-7)
Safety Information
RIDADR UN3082 (liquid)
WGK Germany 2
RTECS UE3600000
HS Code 29242990
Hazardous Substances Data15299-99-7(Hazardous Substances Data)
ToxicityLD50 in mice (g/kg): >5 orally, >1 i.p., >1 s.c. (Kawada)
MSDS Information
ProviderLanguage
SigmaAldrich English
Napropamide Usage And Synthesis
Chemical PropertiesColorless crystalline solid (pure). Technical form is tan to brown solid.
UsesHerbicide.
UsesPreemergence control of annual grasses and certain broad-leaved weeds in mint, orchards, small fruits, tobacco, turf, vegetable crops and ornamentals
UsesNapropamid is used as a pesticide.
DefinitionChEBI: N,N-diethyl-2-(naphthalen-1-yloxy)propanamide is a monocarboxylic acid amide that is propanamide substituted by two ethyl groups at the nitrogen atom and a naphthalen-1-yloxy group at position 2. It is an aromatic ether, a monocarboxylic acid amide and a member of naphthalenes.
General DescriptionNapropamid is a soil herbicide, which can be either sprayed on the surface or incorporated.It can be mainly used for weed control management.
HazardLow toxicity.
Agricultural UsesHerbicide: A General Use Pesticide (GUP) that is compatible with many other fungicides and herbicides. Used to control broadleaf weeds and annual grasses on a variety of crops including vegetables, fruit trees, fruit bushes, oil seed rape, vines, sunflowers, olives, tobacco and mint.
Trade nameCOLZOR TRIO® (dimethachlor + napropamide + clomazone); DEVRINOL®; NAPROGUARD®; WAYLAY®; R-7165®
Potential ExposureA amide/alkanamide general use pesticide and herbicide that is compatible with many other fungicides and herbicides. Used to control broadleaf weeds and annual grasses on a variety of crops including vegetables, fruit trees; fruit bushes, oil seed rape, vines, sunflowers, olives, tobacco, and mint.
Environmental FateSoil. Degrades slowly in soil to 1-naphthol, 1,4-naphthoquinone, 2-(a-naphthoxy)-Nethylpropionamide and 2-(a-naphthoxy)propionamide (Hartley and Kidd, 1987). In moist loam or sandy-loam soils at 70–90°C, the half-life was 8–12 weeks. However, the persistence may be as long as 9 months under conditions where microbial growth is limited (Ashton and Monaco, 1991). Gerstl and Yaron (1983a) reported that the half-life of napropamide in soil can range from 34 to 201 days depending upon the organic matter content, soil texture, soil moisture content and analytical method.
Plant. Rapidly metabolized in tomatoes and several fruit trees forming the watersoluble hexose conjugates of 4-hydroxynapropamide (Humburg et al., 1989; Ashton and Monaco, 1991).
Photolytic. Napropamide decomposes under UV light. Under laboratory conditions, irradiation of an aerated aqueous solution with UV light gave 2-hydroxypropananilide, 2- propenanilide and pyruvinanilide as the major products. Minor photoproducts i

ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required
IncompatibilitiesSlowly hydrolyzes in water, releasing ammonia and forming acetate salt.
Waste DisposalSmall amounts may be destroyed by alkaline hydrolysis. Admixture with alkali can be followed by soil burial. Larger quantities can be disposed of by incineration in admixture with acetone or xylene and using effluent gas scrubbing.
Napropamide Preparation Products And Raw materials
Raw materialsChlorine-->Diethylamine-->Propionic acid-->1-Naphthol-->Propionyl chloride-->Propionamide-->2-Chloropropionic acid
Propisochlor CARPROPAMID 2-Naphthoxyacetic acid Metazachlor Diflufenican Diethyl oxalate Pretilachlor CYCLOPROPANECARBOXAMIDE 2,2-DI-N-PROPYLACETAMIDE Diethyl ether Mefenpyr-diethyl Propionamide Propyzamide Celiprolol Diethyl malonate Ethylene glycol diethyl ether Mefenacet L-Alanyl-L-Glutamine

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