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834-12-8

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834-12-8 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 834-12-8 differently. You can refer to the following data:
1. White, crystalline powder. Slightly soluble in water; soluble in organic solvents.
2. Ametryn is a colorless powder

Uses

Different sources of media describe the Uses of 834-12-8 differently. You can refer to the following data:
1. Pre-emergence and post-emergence herbicides.
2. 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.
3. 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

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.

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.

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

Flammability and Explosibility

Nonflammable

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 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.

Check Digit Verification of cas no

The CAS Registry Mumber 834-12-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,3 and 4 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 834-12:
(5*8)+(4*3)+(3*4)+(2*1)+(1*2)=68
68 % 10 = 8
So 834-12-8 is a valid CAS Registry Number.
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)

834-12-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name ametryn

1.2 Other means of identification

Product number -
Other names Crisatrine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Herbicide
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:834-12-8 SDS

834-12-8Synthetic route

methylthiol
74-93-1

methylthiol

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine
1912-24-9

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine

A

isopropyl chloride
75-29-6

isopropyl chloride

B

ametryn
834-12-8

ametryn

Conditions
ConditionsYield
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

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

ametryn
834-12-8

ametryn

Conditions
ConditionsYield
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

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

ametryn
834-12-8

ametryn

Conditions
ConditionsYield
In tetrahydrofuran; water for 24h; Reflux;65.3%
6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine
1912-24-9

6-chloro-N-ethyl-N'-isopropyl-1,3,5-triazine-2,4-diamine

ametryn
834-12-8

ametryn

2,4-dichloro-6-isopropylamino-1,3,5-triazine
3703-10-4

2,4-dichloro-6-isopropylamino-1,3,5-triazine

ametryn
834-12-8

ametryn

Conditions
ConditionsYield
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

Methoxycarbonylsulfenyl chloride

ametryn
834-12-8

ametryn

C11H19N5O2S2
99384-47-1

C11H19N5O2S2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane46%
ametryn
834-12-8

ametryn

Hydroxyatrazine
2163-68-0

Hydroxyatrazine

Conditions
ConditionsYield
With dipotassium peroxodisulfate Quantum yield; Kinetics; Further Variations:; Reagents; UV-irradiation;
ametryn
834-12-8

ametryn

A

methylthiol
74-93-1

methylthiol

B

N2-ethyl-N4-isopropyl-1,3,5-triazin-2,4-diamine
4150-65-6

N2-ethyl-N4-isopropyl-1,3,5-triazin-2,4-diamine

C

Hydroxyatrazine
2163-68-0

Hydroxyatrazine

Conditions
ConditionsYield
In water at 24.85℃; pH=6; Kinetics; Irradiation;
ametryn
834-12-8

ametryn

cucurbit[8]uril
259886-51-6

cucurbit[8]uril

C48H48N32O16*C9H17N5S

C48H48N32O16*C9H17N5S

Conditions
ConditionsYield
With formic acid In methanol at 40℃; for 48h;
cucurbituril
80262-44-8

cucurbituril

ametryn
834-12-8

ametryn

A

C36H36N24O12*C9H17N5S

C36H36N24O12*C9H17N5S

B

2C36H36N24O12*C9H17N5S

2C36H36N24O12*C9H17N5S

Conditions
ConditionsYield
With formic acid In methanol at 40℃; for 48h;
ametryn
834-12-8

ametryn

cucurbituril
259886-50-5

cucurbituril

C9H17N5S*C42H42N28O14

C9H17N5S*C42H42N28O14

Conditions
ConditionsYield
With formic acid In methanol at 40℃; for 48h;
(2E)-but-2-enedioic acid
110-17-8

(2E)-but-2-enedioic acid

ametryn
834-12-8

ametryn

ametryn fumarate

ametryn fumarate

Conditions
ConditionsYield
In ethanol; water at 45℃;
maleic acid
110-16-7

maleic acid

ametryn
834-12-8

ametryn

ametryn maleate

ametryn maleate

Conditions
ConditionsYield
In ethanol; water at 45℃;
MCPA
94-74-6

MCPA

ametryn
834-12-8

ametryn

2-methyl,4-chlorophenoxyacetic acid ametryn

2-methyl,4-chlorophenoxyacetic acid ametryn

Conditions
ConditionsYield
In n-heptane at 5℃;
3,6-dichloro-O-anisic acid
1918-00-9

3,6-dichloro-O-anisic acid

ametryn
834-12-8

ametryn

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)

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
ConditionsYield
In n-heptane at 50℃; for 48h;

834-12-8Relevant articles and documents

Preparation method of ametryn

-

Paragraph 0038; 0039, (2018/09/21)

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.

Methyl aryl thioether compound, and synthetic method and applications thereof

-

Paragraph 0179; 0180; 0181, (2017/07/21)

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.

Halopyridyl triazolinone herbicides and herbicidal use thereof

-

, (2008/06/13)

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.

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