Fenamiphos

Base Information

• Chemical Name: Fenamiphos
• CAS No.: 22224-92-6
• Molecular Formula: C13H22NO3PS
• Molecular Weight: 303.362
• Hs Code.: 2930909064
• European Community (EC) Number: 244-848-1
• ICSC Number: 0483
• UN Number: 2783
• UNII: H4NO3L2HBE
• DSSTox Substance ID: DTXSID3024102
• Nikkaji Number: J11.420K
• Wikipedia: Fenamiphos
• Wikidata: Q32693
• NCI Thesaurus Code: C163656
• Metabolomics Workbench ID: 45099
• ChEMBL ID: CHEMBL1313005
• Mol file: 22224-92-6.mol

Synonyms:Bay 68138;ethyl 4-(methylthio)m-tolyl isopropylphosphoroamidate;fenamiphos;Nemacur;phenamiphos

Chemical Property of Fenamiphos

Chemical Property:

• Appearance/Colour: Brown waxy solid or colorless solid
• Vapor Pressure: 7.67E-06mmHg at 25°C
• Melting Point: 49 °C
• Refractive Index: 1.524
• Boiling Point: 375.6 °C at 760 mmHg
• PKA: -0.09±0.70(Predicted)
• Flash Point: 181 °C
• PSA: 82.67000
• Density: 1.14 g/cm³
• LogP: 4.62920
• Storage Temp.: 0-6°C
• Water Solubility.: 0.07 g/100 mL
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 303.10580174
• Heavy Atom Count: 19
• Complexity: 314
• Transport DOT Label: Poison

Purity/Quality:

Fenamiphos90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N, T+
• Hazard Codes: T+;N,N,T+
• Statements: 24-28-50/53-36-26/28
• Safety Statements: 23-28-36/37-45-60-61-35-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=O)(NC(C)C)OC1=CC(=C(C=C1)SC)C
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system. This may result in convulsions and respiratory failure. Cholinesterase inhibition. Exposure could cause death. The effects may be delayed. Medical observation is indicated.
• Description: Fenamiphos is a colourless crystal or a tan, waxy solid. It is non-corrosive to metals and breaks down readily in strong acids and bases. Fenamiphos is used as a nematicide and an insecticide for use on a wide variety of field, vegetable, and fruit crops. Fenamiphos has been used primarily to control nematodes and thrips on various agricultural crops (i.e., citrus, grapes, peanuts, pineapples, tobacco, etc.) and non-agricultural (i.e., turf and ornamentals) sites.Alternatively, it can also be used for the treatment of other kinds of invertebrates such as sucking insects and spider mite. Fenamiphos takes effects through inhibiting the acetylcholinesterase in the pests. There are no residential uses for fenamiphos and is a Restricted Use Pesticide (RUP) due to high acute toxicity and toxicity to wildlife. Fenamiphos is a colorless crystalline substance. Solubility in water is 400 mg/L (20 ?C). It is soluble in polar organic solvents. Log Kow = 3.3(20 ?C). It is stable in aqueous media; DT50 (22 ?C) at pH 4, 7, and 9 are 1, 8, and 3 yr.
• Uses: Nematocide. Fenamiphos is primarily used to control nematodes in a wide range of crops and in turf. It will also control mites and sucking insects in crops. Nematocide and insecticide. Systemic broad spectrum nematocide with anticholinesterase activity. Nematocide.

Technology Process of Fenamiphos

There total 2 articles about Fenamiphos which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(methylthio)-m-cresol (3120-74-9) + sodium ethanolate (141-52-6) + isopropylamine (75-31-0) → FENAMIPHOS (22224-92-6)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/0040-4020(95)00413-3

Reference yield:

→ FENAMIPHOS (22224-92-6)

Guidance literature:

Reference yield:

FENAMIPHOS (22224-92-6) → (1-methylethyl)phosphoramidic acid ethyl 3-methyl-4(methylsulfinyl)phenyl ester (31972-43-7,124793-11-9)

Guidance literature:

With perfluoro cis-2-n-butyl-3-n-propyloxaziridine; In various solvent(s); at 0 ℃; for 0.166667h; Yield given;

DOI:10.1016/0040-4020(95)00413-3

upstream raw materials:

4-(methylthio)-m-cresol

sodium ethanolate

isopropylamine

Downstream raw materials:

(1-methylethyl)phosphoramidic acid ethyl 3-methyl-4(methylsulfinyl)phenyl ester

(R)-(+)-ethyl 3-methyl-4-(methylthio)-phenyl (1-methylethyl)phosphoramidate

(S)-(-)-ethyl 3-methyl-4-(methylthio)-phenyl (1-methylethyl)phosphoramidate

Refernces

• 1、 Terreni, Marco,Pregnolato, Massimo,Resnati, Giuseppe,Benfenati, Emilio. "Selective Sulfur Oxygenation in Phosphoroamidate, Thionophosphate, and Thiophosphate Agrochemicals by Perfluoro-cis-2,3-dialkyloxaziridine". . p. 7981 - 7992. Retrieved 2007/10/02.