34622-58-7

Basic information

• Product Name: ORBENCARB
• Synonyms: LANRAY;LANRAY(R);ORTHOBENCARB;ORBENCARB;b3356;diethyl-carbamothioicacis-((2-chlorophenyl)methyl)ester;diethylthiocarbamicacids-(o-chlorobenzyl)ester;diethylthio-carbamicacis-(o-chlorobenzyl)ester
• CAS NO: 34622-58-7
• Molecular Formula: C₁₂H₁₆ClNOS
• Molecular Weight: 257.78
• Mol File: 34622-58-7.mol

Chemical Properties

• Melting Point: 9℃
• Boiling Point: 350.5 °C at 760 mmHg
• Flash Point: 165.8 °C
• Appearance: Colourless liquid
• Density: 1.179 g/cm³
• Vapor Pressure: 4.38E-05mmHg at 25°C
• Refractive Index: n20/D 1.60
• Storage Temp.: 0-6°C
• PKA: -1.28±0.70(Predicted)
• Water Solubility: 24mg/L(temperature not stated)
• BRN: 1968914
• CAS DataBase Reference: ORBENCARB(CAS DataBase Reference)
• NIST Chemistry Reference: ORBENCARB(34622-58-7)
• EPA Substance Registry System: ORBENCARB(34622-58-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22
• RIDADR: 2902
• WGK Germany: 3
• RTECS: EZ7259400
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 34622-58-7(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
ORBENCARB is used as a pharmaceutical compound for its potential therapeutic applications. Its unique structure allows it to interact with specific biological targets, making it a candidate for the development of new drugs.
2. Used in Chemical Research:
ORBENCARB serves as a valuable compound in chemical research, particularly in the study of monothiocarbamic esters and their reactions. It can be used to explore new synthetic pathways and understand the reactivity of similar compounds.
3. Used in Agrochemical Industry:
ORBENCARB may have potential applications in the agrochemical industry as a component in the development of new pesticides or herbicides. Its specific properties could be harnessed to target and control pests or weeds effectively.
4. Used in Material Science:
In the field of material science, ORBENCARB could be utilized in the development of new materials with unique properties, such as improved stability or reactivity. Its chemical structure may contribute to the creation of advanced materials for various applications.
5. Used in Environmental Applications:
ORBENCARB may also find use in environmental applications, such as in the remediation of contaminated sites or the development of new methods for waste treatment. Its chemical properties could be employed to target and neutralize harmful substances in the environment.

Metabolic pathway

When 14C-orbencarb is applied to the soil surface, plants absorb the radioactivity and orbencarb is rapidly transformed to water-soluble metabolites in the plants. The major metabolites identified are 2-chlorobenzyl alcohol and 2-chlorobenzoic acid both in free and conjugated forms, 2-chlorobenzyl sulfonic acid and methyl 2-chlorobenzylsulfone. Hydroxylated metabolites at the phenyl ring and N-vinyl metabolite are found in soybean plants. Orbencarb degrades more rapidly in soils under upland conditions than in soils under flooded conditions. The major degradation products in the soils are orbencarb sulfoxide, monodesmethylorbencarb, methyl-2- chlorobenzylsulfoxide, methyl-2-chlorobenzylsulfone, and 2-chlorobenzylsulfonic acid.

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

Upstream product

• 463-58-1 carbon oxide sulfide 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 109-89-7 diethylamine 
• 201230-82-2 carbon monoxide 
• 22318-01-0 diethylamonium N,N'-dimethylmonothiocarbamate 

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).

Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur

An industrial and economic carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamate herbicides. In the presence of potassium carbonate and solvent DMSO, S-alkyl thiocarbamates, such as thiobencarb and orbencarb (herbicides) are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C).

Facile S-alkyl thiocarbamate synthesis by a novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur

A novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamates. In the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), S-alkyl thiocarbamates are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1 atm, 20°C). In the absence of DBU, however, no formation of S-alkyl thiocarbamate is observed. The present DBU-assisted carbonylation can also be applied to new synthetic methods for benthiocarb and orthobencarb (herbicides) and carbamoyl chlorides.

Novel synthesis of S-alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst

Carbonyl selenide easily reacted with elemental sulfur at low temperature to form carbonyl sulfide in a good yield, and reaction of ammonium salts of selenocarbamates with elemental sulfur brought about ready transformation to those of thiocarbamates. On the basis of the high catalytic activity of selenium for carbonylation of amines with carbon monoxide in addition to these important findings, a convenient new method for synthesis of S-alkyl thiocarbamates was developed through the carbonylation of amines with carbon monoxide and elemental sulfur in the presence of a selenium catalyst under mild conditions followed by alkylation of ammonium salts of the thiocarbamates with alkyl halides.

Facile synthesis of S-alkyl thiocarbamates through reaction of carbamoyl lithium with elemental sulfur

Efficient synthesis of S-alkyl thiocarbamates was developed. The key step of this synthetic method is a conversion of carbamoyl lithium, generated from lithium dialkylamide and carbon monoxide, to lithium thiocarbamate by addition of elemental sulfur.

Synergistic herbicidal compositions and method

A synergistic herbicidal composition comprising a mixture of, (a) an herbicidally effective amount of a thiolcarbamate of the formula, in which X is hydrogen, chlorine or bromine; and R1 and R2 are independently selected from the group consisting of C1-C6 alkyl and C5-C7 cycloalkyl, and (b) an herbicidally effective amount of a propionic acid derivative compound having the formula, wherein R3 is hydrogen or an agriculturally acceptable salt-forming cation selected from the group consisting of diethanolamine, diethylamine, dimethylamine, sodium and potassium; at a weight ratio of (a) to (b) of from about 1:1 to about 4:1.