1014-70-6

Basic information

• Product Name: 2,4-Bis(ethylamino)-6-(methylthio)-1,3,5-triazine
• Synonyms: 2,4-BIS(ETHYLAMINO)-6-METHYLTHIO-1,3,5-TRIAZINE;GY-BON;GYBON(R);G32911;AURORA KA-3877;SIMETRYN;SIMETRYNE;N,N'-DIETHYL-6-(METHYLTHIO)-1,3,5-TRIAZINE-2,4-DIAMINE
• CAS NO: 1014-70-6
• Molecular Formula: C₈H₁₅N₅S
• Molecular Weight: 213.3
• EINECS: 213-801-7
• Product Categories: HERBICIDE;NULL
• Mol File: 1014-70-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 82-83°C
• Boiling Point: 312.8°C (rough estimate)
• Flash Point: 191.6 °C
• Appearance: /
• Density: 1.1553 (rough estimate)
• Vapor Pressure: 2.17E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 0-6°C
• PKA: 4.05±0.10(Predicted)
• Water Solubility: 0.45g/L(room temperature)
• Merck: 13,8610
• BRN: 11728
• CAS DataBase Reference: 2,4-Bis(ethylamino)-6-(methylthio)-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Bis(ethylamino)-6-(methylthio)-1,3,5-triazine(1014-70-6)
• EPA Substance Registry System: 2,4-Bis(ethylamino)-6-(methylthio)-1,3,5-triazine(1014-70-6)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 22-50/53-R50/53-R22
• Safety Statements: 2-60-61-S61-S60-S2
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: XY4025000
• Hazardous Substances Data: 1014-70-6(Hazardous Substances Data)

Usage

Description

2,4-Bis(ethylamino)-6-(methylthio)-1,3,5-triazine, also known as Simetryne, is a methylthiotriazine-based herbicide. It is a white crystalline compound that is easily soluble in organic solvents such as methanol, ethanol, and chloroform. Simetryne has a solubility of 450mg/L in water at 22°C and is prone to decomposition under acidic, alkaline, or high-temperature conditions. As a selective, systemic, and transmissible triazepine herbicide, it can be absorbed through the roots and leaves of weeds, inhibiting their photosynthesis and leading to the death of the leaves due to a lack of greenness and yellowing.

Uses

Used in Rice Paddy:
Simetryne is used as a herbicide in rice paddies to control various types of weeds, including barnyardgrass, ox hair grass, sagebrush, Alisma, wild cigu, mother grass, and Xiaoci grass. It is effective in preventing the growth of these weeds, ensuring a healthy crop yield.
Used in Combination with Other Herbicides:
Simetryne can be combined with other herbicides such as salamander and butachlor to expand the herbicide spectrum, providing broader weed control and enhancing the effectiveness of the treatment.
Used in Other Crops:
In addition to rice paddies, Simetryne is also used for weed control in corn, soybean, wheat, peanut, and cotton crops. Its selective nature allows it to target specific weeds without causing harm to the desired crop, making it a valuable tool in agricultural practices.

Synthesis

In the presence of sodium hydroxide, cyanuric chloride reacts with monoethylamine and sodium methyl mercaptan to give Simetryne.

InChI:InChI=1/C8H15N5S/c1-4-9-6-11-7(10-5-2)13-8(12-6)14-3/h4-5H2,1-3H3,(H2,9,10,11,12,13)

Upstream product

• 122-34-9 Simazine 
• 616-38-6 carbonic acid dimethyl ester 
• 5759-58-0 2,4,6-tris(methylthio)-1,3,5-triazine 
• 75-04-7 ethylamine 

Relevant articles and documents

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.

Synergistic herbicidal mixtures

PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.

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