834-12-8

Usage

Uses

Used in Agriculture:
Ametryn is used as a pre-emergence and post-emergence herbicide for controlling broad-leaved and grass weeds in crops such as corn, sugarcane, and certain citrus and subtropical fruits like bananas and pineapples.
Used in Non-cropland:
Ametryn is also used as a herbicide in non-cropland to manage unwanted vegetation.
Used in Potato Farming:
Ametryn serves as a preharvest and postharvest desiccant in potatoes, helping to control both the crop and weeds.

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.

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/kgLD50 oral (mouse): 965 mg/kgLD50 skin (rabbit): >5000 mg/kg.

Flammability and Explosibility

Nonflammable

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 groundwaterChemical/Physical. Hydrolyzes to the 6-hydroxy analog, especially in the presence ofPhotolytic. 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.

InChI:InChI=1/C9H17N5S/c1-5-10-7-12-8(11-6(2)3)14-9(13-7)15-4/h6H,5H2,1-4H3,(H2,10,11,12,13,14)

Synthetic route

methylthiol (74-93-1) + 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) → isopropyl chloride (75-29-6) + ametryn (834-12-8)

Conditions	Yield
With ZSM-5 In isopropyl alcohol at 90 - 110℃; under 3675.37 - 5850.59 Torr; for 1h; Temperature; Pressure; Reagent/catalyst; Sealed tube;	A 70.91 g B 99.9%

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) + carbonic acid dimethyl ester (616-38-6) → ametryn (834-12-8)

Conditions	Yield
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere;	84%
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere;	84%

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) + sodium thiomethoxide (5188-07-8) → ametryn (834-12-8)

Conditions	Yield
In tetrahydrofuran; water for 24h; Reflux;	65.3%

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine (1912-24-9) → ametryn (834-12-8)

2,4-dichloro-6-isopropylamino-1,3,5-triazine (3703-10-4) → ametryn (834-12-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / water; toluene / 0.25 h / 15 - 20 °C 2: tetrahydrofuran; water / 24 h / Reflux View Scheme

Methoxycarbonylsulfenyl chloride (26555-40-8) + ametryn (834-12-8) → C11H19N5O2S2 (99384-47-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	46%

ametryn (834-12-8) → Hydroxyatrazine (2163-68-0)

Conditions	Yield
With dipotassium peroxodisulfate Quantum yield; Kinetics; Further Variations:; Reagents; UV-irradiation;

ametryn (834-12-8) → methylthiol (74-93-1) + N2-ethyl-N4-isopropyl-1,3,5-triazin-2,4-diamine (4150-65-6) + Hydroxyatrazine (2163-68-0)

Conditions	Yield
In water at 24.85℃; pH=6; Kinetics; Irradiation;

ametryn (834-12-8) + cucurbit[8]uril (259886-51-6) → C48H48N32O16*C9H17N5S

Conditions	Yield
With formic acid In methanol at 40℃; for 48h;

cucurbituril (80262-44-8) + ametryn (834-12-8) → C36H36N24O12*C9H17N5S + 2C36H36N24O12*C9H17N5S

Conditions	Yield
With formic acid In methanol at 40℃; for 48h;

ametryn (834-12-8) + cucurbituril (259886-50-5) → C9H17N5S*C42H42N28O14

Conditions	Yield
With formic acid In methanol at 40℃; for 48h;

(2E)-but-2-enedioic acid (110-17-8) + ametryn (834-12-8) → ametryn fumarate

Conditions	Yield
In ethanol; water at 45℃;

maleic acid (110-16-7) + ametryn (834-12-8) → ametryn maleate

Conditions	Yield
In ethanol; water at 45℃;

MCPA (94-74-6) + ametryn (834-12-8) → 2-methyl,4-chlorophenoxyacetic acid ametryn

Conditions	Yield
In n-heptane at 5℃;

3,6-dichloro-O-anisic acid (1918-00-9) + ametryn (834-12-8) → 3,6-dichloro-2-methoxybenzoic acid : 4-N-ethyl-6-methylsulfanyl-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine (1:1)

Conditions	Yield
In n-heptane at 50℃; for 48h;

Upstream product

• 3703-10-4 2,4-dichloro-6-isopropylamino-1,3,5-triazine 
• 1912-24-9 6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine 
• 5188-07-8 sodium thiomethoxide 
• 74-93-1 methylthiol 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 74-93-1 methylthiol 
• 4150-65-6 N²-ethyl-N⁴-isopropyl-1,3,5-triazin-2,4-diamine 
• 2163-68-0 Hydroxyatrazine 

Relevant academic research and scientific papers

Preparation method of ametryn

The invention provides a method for preparing ametryn through a green salt-free technology. The method comprises the following step: under the action of a catalyst, enabling atrazine and methanethiolto react in isopropyl alcohol to prepare the ametryn. According to the method provided by the invention, the production and utilization of sodium thiomethoxide with an offensive odor are avoided; meanwhile, a catalyst with the offensive odor, i.e., trimethylamine hydrochloride, is not used, and the environment-friendly catalyst is used, so that the odor can be avoided radically and the quality ofa product and the environment of a production site are extremely improved; meanwhile, industrial salt is not generated; the method is environmentally friendly and the environment protection cost is greatly reduced.

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

In this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol is practically amenable to multigram-scale synthesis with a lower catalysis loading and a higher yield.

Methyl aryl thioether compound, and synthetic method and applications thereof

The invention discloses a methyl aryl thioether compound represented by formula 2, and a synthetic method and applications thereof. According to the synthetic method, in a reaction solvent, an aryl halide or an aromatic halide, dimethyl carbonate, and potassium thioacetate are taken as reaction raw materials, reaction is carried out in the presence of metal palladium catalyst under the action of a ligand and an alkali so as to obtain the methyl aryl thioether compound. The reaction conditions of the synthetic method are mild; the raw materials are cheap and easily available; reaction operation is simple; yield is relatively high. The methyl aryl thioether compound can be used for providing skeleton structures for the synthesis of a plurality of natural products and medicines, and can be widely applied in industrialized large-scale production.

Design, synthesis, and biological activities of arylmethylamine substituted chlorotriazine and methylthiotriazine compounds

Heterocyclic rings were introduced into the core structure of s-triazine to design and synthesize a series of novel triazines containing arylmethylamino moieties. These compounds were characterized by using spectroscopic methods and elemental analysis. Their herbicidal, insecticidal, fungicidal, and antitumor activities were evaluated. Most of these compounds exhibited good herbicidal activity, especially against the dicotyledonous weeds, and compound F8 was almost at the same level as the control compound atrazine. Their structure-activity relationships were discussed. At the same time, some triazines had interesting fungicidal and insecticidal activities, of which F4 exhibited 100% efficacy against Puccinia triticina even at 20 ppm, and F5 showed Lepidopteran-specific activity in both leaf-piece and artificial diet assays. Moreover, these compounds showed antitumor activities against leukemia HL-60 cell line and lung adenocarcinoma A-549 cell line.

Halopyridyl triazolinone herbicides and herbicidal use thereof

Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.

Process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines

An improved process for the preparation of 2,4-di(alkylamino)-6-alkylthio-s-triazines wherein cyanuric chloride is reacted in successive steps with two appropriate alkylamines and an alkyl mercaptan is described where the improvement involves use of a single water-immiscible solvent and a phase transfer catalyst in the mercaptan addition step.

Novel chloroacetanilide derivatives and herbicides containing the same for use in paddy field

Disclosed herein are novel chloroacetanilide derivatives which act as remarkably effective herbicides when sprayed in a paddy field, the chloroacetanilide derivatives being 2',6'-diethyl-N-[(cis-alkenyloxy)methyl]-2-chloroacetanilides [A] represented by the general formula STR1 wherein R is a cis-form alkenyl group having 4 or 5 carbon atoms. Also disclosed are herbicide compositions for use in a paddy field and containing at least one of said chloroacetanilide derivatives [A] and at least one pyrazole derivative [B] represented by the general formula STR2 wherein R is a hydrogen atom or methyl group and X is a 4-toluenesulfonyl group or benzoylmethyl group; or-α-(2-naphtoxy)-propyonanilide [C] represented by the formula STR3

Heats of Combustion and of Formation of Ametrin and Prometrin

The standard enthalpies of combustion of crystalline 2-methylthio-4-ethylamino-6-isopropylamino-symm-triazine (Ametrin) and 2-methylthio-4,6-bis-(isopropylamino)-symm-triazine (Prometrin) have been determined calorimetrically.The standard enthalpies of formation have been calculated from the results.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

4,5-Dichloroimidazole-2-carboxylic acid derivatives

4,5-Dichloroimidazole-2-carboxylic acid derivatives of the formula STR1 in which the group STR2 represents a carbon atom which has three bonds to hetero-atoms, and their salts with bases, possess insecticidal, acaricidal, fungicidal, nematicidal and herbicidal properties.