13509-41-6

Basic information

• Product Name: O-methyl phenylcarbamothioate
• CAS NO: 13509-41-6
• Molecular Formula: C₈H₉NOS
• Molecular Weight: 167.2282
• Mol File: 13509-41-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 227.5°C at 760 mmHg
• Flash Point: 91.4°C
• Density: 1.222g/cm³
• Vapor Pressure: 0.0774mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: O-methyl phenylcarbamothioate(CAS DataBase Reference)
• NIST Chemistry Reference: O-methyl phenylcarbamothioate(13509-41-6)
• EPA Substance Registry System: O-methyl phenylcarbamothioate(13509-41-6)

Safety Data

• Hazardous Substances Data: 13509-41-6(Hazardous Substances Data)

Usage

General Description

O-methyl phenylcarbamothioate is a chemical compound that belongs to the class of phenylcarbamothioate pesticides. It is also known by its trade name "Tolclofos-methyl" and is widely used as a fungicide for protecting crops such as fruit trees, strawberries, potatoes, and vegetables from various fungal diseases. O-methyl phenylcarbamothioate works by inhibiting the enzyme succinate dehydrogenase in fungal cells, disrupting their energy production and ultimately leading to their death. However, it is important to handle this chemical with care as it is toxic to aquatic organisms and can have harmful effects on human health if not used properly. Therefore, it is essential to follow safety guidelines and regulations when using O-methyl phenylcarbamothioate in agricultural or industrial settings.

Upstream product

• 67-56-1 methanol 
• 102-08-9 N,N-diphenylthiourea 
• 98-95-3 nitrobenzene 
• 56-23-5 tetrachloromethane 
• 76-89-1 methyl benzilate 
• 103-72-0 phenyl isothiocyanate 
• 683-63-6 O-methyl thiocarbamate 
• 98-80-6 phenylboronic acid 
• 108-90-7 chlorobenzene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 105-45-3 acetoacetic acid methyl ester 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 3319-20-8 C₁₄H₁₀ClF₃N₂OS₂ 
• 19046-09-4 (4-nitro-phenyl)-(4-nitro-phenylsulfanyl)-diazene 
• 63321-86-8 2-methoxybenzothiazole 
• 1609553-12-9 (Ph₃P)₂Cu(I)[MeOC(=S)N(H)Ph]Cl 
• 1258410-91-1 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranosyl O-methyl phenylcarbamothioate 
• 1258410-92-2 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranosyl O-methyl phenylcarbamothioate 
• 149160-55-4 {(Cy)3phosphinegold(I)-SC(=NPh)OMe} 
• 149160-50-9 {triphenylphosphinegold(I)-SC(=NPh)OMe} 
• 149160-46-3 {triethylphosphinegold(I)-SC(=NPh)OMe} 
• 5407-58-9 2-butoxy-6-nitro-benzothiazole 
• 70292-57-8 2-ethoxy-6-nitro-1,3-benzothiazole 
• 4308-10-5 2-methoxy-6-nitrobenzo[d]thiazole 
• 13509-38-1 N-phenyl-S-methyl-thiocarbamate 
• 603-54-3 N,N-diphenylurea 

Relevant articles and documents

Computational tools for mechanistic discrimination in the reductive and metathesis coupling reactions mediated by titanium(IV) isopropoxide

A theoretical study has been carried out at the B3LYP/LANL2DZ level to compare the reactivity of phenyl isocyanate and phenyl isothiocyanate towards titanium(IV) alkoxides. Isocyanates are shown to favour both mono insertion and double insertion reactions. Double insertion in a head-to-tail fashion is shown to be more exothermic than double insertion in a head-to-head fashion. The head-to-head double insertion leads to the metathesis product, a carbodiimide, after the extrusion of carbon dioxide. In the case of phenyl isothiocyanate, calculations favour the formation of only mono insertion products. Formation of a double insertion product is highly unfavourable. Further, these studies indicate that the reverse reaction involving the metathesis of N,N ′-diphenyl carbodiimide with carbon dioxide is likely to proceed more efficiently than the metathesis reaction with carbon disulphide. This is in excellent agreement with experimental results as metathesis with carbon disulphide fails to occur. In a second study, multilayer MM/QM calculations are carried out on intermediates generated from reduction of titanium(IV) alkoxides to investigate the effect of alkoxy bridging on the reactivity of multinuclear Ti species. Bimolecular coupling of imines initiated by Ti(III) species leads to a mixture of diastereomers and not diastereoselective coupling of the imine. However if the reaction is carried out by a trimeric biradical species, diastereoselective coupling of the imine is predicted. The presence of alkoxy bridges greatly favours the formation of the d,l (±) isomer, whereas the intermediate without alkoxy bridges favours the more stable meso isomer. As a bridged trimeric species, stabilized by bridging alkoxy groups, correctly explains the diastereoselective reaction, it is the most likely intermediate in the reaction.

Organocatalytic, difluorocarbene-based S-difluoromethylation of thiocarbonyl compounds

Upon treatment with trimethylsilyl 2,2-difluoro-2-fluorosulfonylacetate (TFDA) and a catalytic amount of N,N,N′,N′-tetramethyl-1,8-diaminonaphthalene, secondary thioamides and thiocarbamates undergo selective difluoromethylation on the sulfur atom to give S-difluoromethyl thioimidates and thioiminocarbonates in good yields, respectively. This is the first report on the synthesis of acyclic difluoromethyl thioimidates and thioiminocarbonates. The key for S-difluoromethylation is the organocatalytic generation of difluorocarbene (:CF2) under mild conditions, which prevents decomposition of the substrates. This process provides an efficient approach to pharmaceuticals and agrochemicals bearing a difluoromethylsulfanyl group, starting from widely available thiocarbonyl compounds.

Effect of successive increase in alcohol chains on reaction with isocyanates and isothiocyanates

The reaction of isocyanates and isothiocyanates with long-chain alcohols, e.g. n-hexanol, n-heptanol and n-octanol, exclusively gave N-aryl-O-alkyl carbamates, while N-aryl-O-alkyl carbamates were formed along with symmetrical 1,3-disubstituted ureas and thioureas when the same reactions were carried out with small-chain alcohols at room temperature without using any solvent.