2655-14-3

Basic information

• Product Name: XMC
• Synonyms: XMC;XMC emulsion;XMC STANDARD;3,5-dimethyl-phenomethylcarbamate;3,5-Dimethylphenyl Methylcarbamate;3,5-Dimethylphenyl N-methylcarbamate;3,5-dimethylphenylmethylcarbamate;3,5-dimethylphenyln-methylcarbamate
• CAS NO: 2655-14-3
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Product Categories: Pharmaceutical Raw Materials
• Mol File: 2655-14-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 101-102℃ (toluene pentane )
• Boiling Point: 311.75°C (rough estimate)
• Flash Point: 114.2°C
• Appearance: /
• Density: 0.54 g/cm3
• Vapor Pressure: 0.00931mmHg at 25°C
• Refractive Index: 1.5150 (estimate)
• Storage Temp.: 0-6°C
• PKA: 12.38±0.46(Predicted)
• Water Solubility: 470 mg l-1 (20 °C)
• CAS DataBase Reference: XMC(CAS DataBase Reference)
• NIST Chemistry Reference: XMC(2655-14-3)
• EPA Substance Registry System: XMC(2655-14-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 2655-14-3(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
3,5-Xylyl methylcarbamate is used as an insecticide for the control of various pests, particularly leafhoppers and planthoppers, which are known to cause significant damage to rice crops. Its application helps protect the rice plants from these pests, ensuring a healthy yield.
Used in Tea Crop Protection:
In addition to its use in rice crops, 3,5-Xylyl methylcarbamate is also employed as a pesticide in the protection of green tea crops. It is specifically used to control tea green leafhoppers, which can cause severe damage to tea plants if left unchecked. By using XMC, tea farmers can maintain the quality and quantity of their tea harvest.
Used in Pesticide Formulation:
3,5-Xylyl methylcarbamate is an essential component in the formulation of various pesticides. Its inclusion in these formulations enhances their effectiveness against a range of pests, making it a valuable asset in the agricultural industry.

Metabolic pathway

Metabolic pathways for XMC involve hydroxylation of ring-methyl groups, N-methyl groups and of the phenyl ring. Hydrolysis of the ester moiety occurs in soils.

Degradation

XMC is rapidly hydrolysed in alkaline media to afford the phenol (2). It is relatively stable in neutral and weakly acidic aqueous solutions even at temperatures up to 90 °C. Aqueous solutions of XMC are stable to light(PM).

InChI:InChI=1/C10H13NO2/c1-7-4-8(2)6-9(5-7)13-10(12)11-3/h4-6H,1-3H3,(H,11,12)

Upstream product

• 22013-97-4 N-methyl-thiocarbamic acid S-methyl ester 
• 108-68-9 3,5-Dimethylphenol 
• 96-31-1 N,N'-Dimethylurea 
• 624-83-9 methyl isocyanate 

Relevant articles and documents

One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

A general procedure for the synthesis of alkyl and aryl alkylcarbamates starting from the corresponding 5-methyl N-alkylthiocarbamates is described. This procedure consists of three steps that are carried out in a one-pot fashion, without isolating the intermediate N-alkylcarbamoyl chlorides or alkyl isocyanates. All the target products were obtained in high yields (16 examples, average yield 91%). To be noted is the recovery of a co-product of industrial interest, dimethyl disulfide, in a half mole amount for each mole of thiocarbamate, with complete exploitation of the reagent. The alkyl isocyanates, if required, can also be isolated in high yields. Georg Thieme Verlag Stuttgart.

An easy and efficient one-step procedure for the preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

A general, one-step procedure for the synthesis of alkyl and aryl alkylcarbamates, by the direct reaction of S-methyl N-alkylthiocarbamates with alcohols or phenols in toluene at reflux in the presence of triethylamine, is reported. All the target products were obtained in high yield (15 examples, average yield 94%) and very high purity (>99.2%). The recovery of a co-product of industrial interest, methanethiol, in an amount of one mole for each mole of thiocarbamate, with complete exploitation of the reagent, should also be noted. Georg Thieme Verlag Stuttgart.

Fluid insecticidal formulations for treatment of parasitic insect larvae by dermal application

The present invention relates to the use of polysiloxanes containing at least one quaternary ammonium group as formulation auxiliary in formulations of larvicidal and/or ovicidal active compounds and to compositions containing a) a larvicidal and/or ovicidal active compound and b) a polysiloxane derivative with at least one quaternary ammonium group per molecule, and, if appropriate, further auxiliaries and carriers.

Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives

The present invention provides a process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives comprising reacting an amine, alcohol, or oxime nucleophile with a urea in an inert organic solvent.

Pyrazole oxime derivatives and compositions

A pyrazole oxime derivative represented by the general formula (I) which is useful as an insecticide and fungicide, STR1 wherein the structural elements are defined in the specification, and the method of controlling said pests. The compounds represented by the general formula (I) can be synthesized by the methods disclosed in the specification.

Process for preparing ureas

The present invention provides a novel process for preparing herbicidal and insecticidal ureas, carbamates and carbamate derivatives of the formula E is -O- or -C(R4)2- ;, R is C1-C7 alkyl;, R1 is H, C1-C7 alkyl, C3-C7 cycloalkyl, phenyl, or C1-C4 alkylphenyl;, R2 is H, C1-C7 alkyl, C3-C7 cycloalkyl, C2-C7 alkenyl, C2-C7 alkynyl, or phenyl optionally substituted with Cl, Br, -NO2, -CF3, C1-C4 alkyl, C1-C4 alkoxy, or -N(C1-C4 alkyl)2;, R3 is H, F, Cl, Br, -CF3, C1-C7 alkyl option-ally substituted with F, Cl, or Br, -S(O)nC1-C7 alkyl, C1-C7 alkoxy, C3-C7 cycloalkyl optionally substituted with F, Cl, or Br, or phenyl optionally substituted with F, Cl, Br, -NO2, -CF3, or C1-C4 alkyl;, R4 is H or C1-C4 alkyl;, R5 is C1-C7 alkoxy or -S(O)nC1-C7 alkyl;, R6 is C1-C5 alkyl optionally substituted with F, Cl, or Br, C3-C5 cycloalkyl, phenyl, or, , - X is R3, -N=CH-N(C1-C4 alkyl)2, -N(C1-C4 alkyl)2 or -N(C2-C4 alkenyl)2, Y is H or S(O)nC1-C7 alkyl;, Z is H, C1-C4 alkyl, Cl, F, Br, haloalkyl, -NO2, -N(C1-C4 alkyl)2, -C≡N, phenyl, -S(C1-C4 alkyl), or C1-C4 alkoxy;, n is 0, 1, or 2; and, m is 1, 2 or 3,comprising reacting a nucleophile of the formula A-H, wherein A is as defined above, with a urea of the formula wherein each R is independently chosen from R as set forth above and each R1 is independently chosen from R1 as set forth above.

Process for the production of N-methylcarbamates

Process for the production of N-methylcarbamates: STR1 (wherein RO- is the radical of a substituted phenol or of a naphthol), wherein: in a first reaction step methylamine and diphenyl carbonate are reacted with each other, operating in the liquid phase and as a continuous process, in order to form phenol and phenyl-N-methylurethane; in a second reaction step phenyl-N-methylurethane, within the related reaction mixture outcoming from the first step, is thermally continuously decomposed, to yield a gaseous stream containing methyl isocyanate, from which the components different than methyl isocyanate are condensed off; in a third step the methyl isocyanate stream, outcoming from the second step, after an optional preliminary condensation, is continuously fed and contacted with a solution of a substituted phenol or of a naphthol in an inert organic solvent, containing a basic catalyst, to form N-methylcarbamate (I); N-methylcarbamate (I) is finally recovered from the reaction mixture outcoming from the third step.