Napropamide is a widely used herbicide. It has a low mammalian toxicity but is is a known skin and eye irritant. It is moderately soluble in water, and is quite volatile. It is moderately persistent in soil systems and data suggests that under certain conditions it may be persistent in water. It has a low toxicity to birds but is moderately toxic to most aquatic species, honeybees and earthworms.
Colorless crystalline solid (pure). Technical
form is tan to brown solid.
Napropamid is used as a pesticide.
Preemergence control of annual grasses and certain broad-leaved weeds in mint,
orchards, small fruits, tobacco, turf, vegetable crops and ornamentals
The industrial synthesis of napropamide begins with the preparation of the key intermediate 2-(1-naphthalenyloxy)propanoic acid. This is typically synthesised by reacting 1-naphthol with 2-chloropropionic acid or its derivatives under basic conditions, forming an ether linkage between the naphthalene ring and the propanoic acid side chain. The resulting intermediate is then subjected to amidation using diethylamine, often in the presence of coupling agents or activating reagents such as thionyl chloride or carbodiimides to facilitate the formation of the amide bond. These reactions are carried out in organic solvents like toluene or acetonitrile under controlled temperature and pH to ensure high yield and purity.
ChEBI: 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.
Napropamid is a soil herbicide, which can be either sprayed on the surface or incorporated.It can be mainly used for weed control management.
Herbicide: 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.
COLZOR TRIO® (dimethachlor + napropamide
+ clomazone); DEVRINOL®; NAPROGUARD®;
WAYLAY®; R-7165®
Selective, systemic, absorbed through roots and translocated. Acts by preventing root cell elongation and so disrupting growth. Inhibition of very long chain fatty acids (VLCFA, inhibition of cell division)
A 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.
Soil. 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
UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous
hazardous material, Technical Name Required
Slowly hydrolyzes in water, releasing
ammonia and forming acetate salt.
Small 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.
