Description
Prometon is a non-selective herbicide. It is moderately soluble in water, volatile and, based on its chemical properties, it is highly mobile and has a high potential to leach to groundwater. It can be highly persistent in both soil and aquatic systems. It has a relatively low mammalian toxicity and is not expected to bioaccumulate. It is classified as an irritant. It is moderately toxic to birds, most aquatic species and honeybees.
Chemical Properties
Colorless crystalline solid or white powder.
Odorless.
Uses
Nonselective preemergence and postemergence herbicide used to control most
annual and perennial broad-leaved weeds, grasses and brush weeds on noncrop land.
Uses
Nonselective herbicide.
Definition
ChEBI: A methoxy-1,3,5-triazine that is 6-methoxy-1,3,5-triazine-2,4-diamine in which the one of the hydrogens of each amino group is substituted by an isopropyl group.
Production Methods
The industrial synthesis of prometon begins with the formation of the 1,3,5-triazine ring, typically derived from cyanuric chloride or melamine. The triazine core undergoes sequential nucleophilic substitution with isopropylamine to introduce the two diisopropylamino groups at the 2- and 4-positions. The final step involves methoxylation at the 6-position using sodium methoxide or methanol under basic conditions. These reactions are carried out in organic solvents such as acetone or acetonitrile under controlled temperature and pH to ensure high yield and selectivity. After synthesis, the crude product is purified through crystallisation or solvent extraction.
Hazard
Toxic by ingestion.
Agricultural Uses
Herbicide: A non-selective pre-emergence and post-emergence herbicide. Use around buildings, storage areas, industrial sites, fences, recreational areas, rights-of-way, railroads, pipelines, lumberyards, tank farms, and similar areas. Controls broadleaf weeds and grasses over an extended period of time. Not listed for use in EU countries. Registered for use in the U.S.
Trade name
ACME® Prometon; G-31435®; GESAFRAM® 50; GESAFRAM®; GESAGRAM®; GROUND ZERO®; KLEENWALK®; NIX®; NOXALL®; ONTRACK®; PRIMATOL® (prometon); PROMETONE®; WEED-GO®
Mechanism of action
Non-selective, systemic absorbed by foliage and roots, inhibits photosynthesis. Affects photosystem II competing with plastoquinone and modifying electron transport processes.
Potential Exposure
A nonselective pre-emergence and
postemergence triazine herbicide. Use around buildings,
storage areas, industrial sites, fences, recreational areas,
rights-of-way, railroads, pipelines, lumberyards, tank farms,
and similar areas. Controls broadleaf weeds and grasses
over an extended period of time
Environmental Fate
Soil. Degrades in soil yielding hydroxy metabolites and dealkylation of the side chains
(Hartley and Kidd, 1987).
Photolytic. Pelizzetti et al. (1990) studied the aqueous photocatalytic degradation of
prometon and other s-triazines (ppb level) using simulated sunlight (λ >340 nm) and
titanium dioxide as a photocatalyst. Prometon rapidly degraded forming cyanuric acid,
nitrates, the intermediate tentatively identified as 2,4-diamino-6-hydroxy-N,N′-bis(1-methylethyl)-1,3,5-triazine and other intermediate compounds similar to those found for atrazine. Mineralization of cyanuric acid to carbon dioxide was not observed (Pelizzetti et al.,
1990).
Shipping
UN2763 Triazine pesticides, solid, toxic, Hazard
Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explo-
sions. Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. UV causes decomposition.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical
incinerator equipped with an afterburner and scrubber. All
federal, state, and local environmental regulations must be
observed. In accordance with 40CFR165, follow recom-
mendations for the disposal of pesticides and pesticide
containers. Containers must be disposed of properly by
following package label directions or by contacting your
local or federal environmental control agency, or by
contacting your regional EPA office.
