28249-77-6

Basic information

• Product Name: Thiobencarb
• Synonyms: TOBOSA;(s-(4-chlorobenzyl)n,n-diethylthiolcarbamate);B 3015;b-3015;bolero8ec;Carbamic acid, diethylthio-, S-(p-chlorobenzyl) ester;Carbamothioic acid, diethyl-, S-[(4-chlorophenyl)methyl] ester;diethyl-carbamothioicacid,s-((4-chlorophenyl)methyl)ester
• CAS NO: 28249-77-6
• Molecular Formula: C₁₂H₁₆ClNOS
• Molecular Weight: 257.78
• EINECS: 248-924-5
• Product Categories: HERBICIDE;TF - TOPesticides&Metabolites;Alpha sort;Herbicides;Pesticides&Metabolites;Q-ZAlphabetic;Thiocarbamates
• Mol File: 28249-77-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 1.7°C
• Boiling Point: 126-129°C
• Flash Point: 165.767 °C
• Appearance: Pale yellow/Liquid
• Density: 1.0756 (rough estimate)
• Vapor Pressure: 4.38E-05mmHg at 25°C
• Refractive Index: 1.5630 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: -1.26±0.70(Predicted)
• Water Solubility: 30mg/L(22 oC)
• BRN: 1968440
• CAS DataBase Reference: Thiobencarb(CAS DataBase Reference)
• NIST Chemistry Reference: Thiobencarb(28249-77-6)
• EPA Substance Registry System: Thiobencarb(28249-77-6)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3082
• WGK Germany: 3
• RTECS: EZ7260000
• Hazardous Substances Data: 28249-77-6(Hazardous Substances Data)

Usage

Chemical Properties

Amber-colored, slightly water-soluble, liquid.

Uses

Thiocarbamate herbicide used to control sedges and grasses in rice paddies.

General Description

Pale yellow to brownish yellow liquid. Non corrosive. Used as an herbicide.

Air & Water Reactions

Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.

Reactivity Profile

Thiobencarb is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.

Hazard

Toxic.

InChI:InChI=1/C12H16ClNOS/c1-3-14(4-2)12(15)16-9-10-5-7-11(13)8-6-10/h5-8H,3-4,9H2,1-2H3

Upstream product

• 2430-00-4 2,2,2-trichloro-N,N-diethylacetamide 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 109-89-7 diethylamine 
• 534572-34-4 trichlorothioacetic acid S-(4-chlorobenzyl) ester 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 201230-82-2 carbon monoxide 
• 463-58-1 carbon oxide sulfide 
• 22318-01-0 diethylamonium N,N'-dimethylmonothiocarbamate 

Downstream Products

• 39918-94-0 S-(4-chlorobenzyl) ethylthiocarbamate 
• 50586-77-1 S-(4-chlorobenzyl) acetyl(ethyl)thiocarbamate 
• 104-88-1 4-chlorobenzaldehyde 
• 6258-66-8 (4-chlorophenyl)methanethiol 
• 873-76-7 para-Chlorobenzyl alcohol 
• 51954-76-8 thiobencarb sulfoxide 
• 75-04-7 ethylamine 

Relevant articles and documents

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

Facile one-pot synthesis of S-alkyl thiocarbamates

We report a novel one-pot two-step synthesis of a variety of S-alkyl thiocarbamates. This method offers a two-directional approach making use of trichloroacetyl chloride, requires no complex starting material, incorporates a variety of substituents, and proceeds in high yields.

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.