Ametryn

Chemical properties

White, crystalline powder. Slightly soluble in water; soluble in organic solvents.

Chemical properties

Ametryn is a colorless powder

The Uses of Ametryn

Ametryn is a methylthiotriazine based herbicide which inhibits photosynthesis and other enzymatic processes. Ametryn is used to control broadleaf weeds and annual grasses in pineapple, sugarcane and b ananas.

The Uses of Ametryn

Pre-emergence and post-emergence herbicides.

The Uses of Ametryn

Herbicide used to control broad-leaved and grass weeds in corn, sugarcane, certain citrus subtropical fruits (bananas, pineapple) and in noncropland. Preharvest and postharvest desiccant used in potatoes to control both crop and weeds

Definition

ChEBI: A methylthio-1,3,5-triazine that is 2-(methylsulfanyl)-1,3,5-triazine substituted by an ethylamino and an isopropylamino group at positions 4 and 6 respectively.

Production Methods

Ametryn is a colorless crystal synthesized by reacting atrazine with methyl mercaptan in the presence of an equivalent of NaOH or by reacting 2-mercapto-4-ethylamino-6-isopropylamino- 1,3,5-triazine with a methylating agent in the presence of NaOH. It is stable in slightly acidic or alkaline media, but is hydrolyzed to the inactive 6-hydroxy derivative in strong acidic or basic media.

General Description

Crystals. Melting point 190-192°F (88-89°C). Used as a herbicide.

Reactivity Profile

An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Toxic by ingestion.

Health Hazard

Moderately toxic by ingestion; human toxic-ity data not available; a mild irritant to skinand eye.
LD50 oral (rat): 508 mg/kg
LD50 oral (mouse): 965 mg/kg
LD50 skin (rabbit): >5000 mg/kg.

Flammability and Explosibility

Non flammable

Agricultural Uses

Herbicide: Ametryn is a herbicide which inhibits photosynthesis and other enzymatic processes. It is used to control broadleaf weeds and annual grasses in pineapple, sugarcane and bananas. Uses are being supported in the U.S. only for the following agricultural crops: field corn, popcorn, sugarcane, and pineapple (EPA, 2005). Used in premixes with atrazine, diuron, simazine, and terbutryn. Not approved for use in the EU.

Trade name

AMESIP®; AMERTREX®; AMETREX; AMETRON SC®; AMETRYNE TECHNICAL®; AMIGAN®; AMULEX; CRISATRINE®; CRISATRINA®; DORUPLANT®; EVIK®; G-34162®; GESAPAX®; HERBIPAK®; KRISMAT®; OXON PRIMATOL Z 80®; SANCOPAX®; TRINATOX-D®

Potential Exposure

Ametryn, a triazine and an organosulfide, amine compound A potential danger to those involved in the manufacture, formulation and application of this selective herbicide.

Carcinogenicity

No carcinogenic response was observed at the highest dose tested in lifetime studies, 2000 ppm, for both rats and mice.

Environmental Fate

Biological. Cook and Hütter (1982) reported that bacterial cultures were capable of degrading ametryne forming the corresponding hydroxy derivative (hydroxyametryne)
Soil. Although no products were reported, the half-life in soil is 70–120 days (Worthing and Hance, 1991)
Groundwater. According to the U.S. EPA (1986) ametryn has a high potential to leach to groundwater
Chemical/Physical. Hydrolyzes to the 6-hydroxy analog, especially in the presence of
Photolytic. The dye-sensitized photodecomposition of ametryn was studied in aqueous, aerated solutions (Rejto et al., 1983). When an aqueous ametryn solution was irradiated in sunlight for several hours, 2-(methylthio)-4-(isopropylamino)-6-amino-

Shipping

UN2763 Triazine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Incompatibilities

Triazines are incompatible with nitric acid. Amines are chemical bases, they neutralize acids to form salts plus water with an exothermic reaction. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides.

Waste Disposal

In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.