Phoxim CAS NO.14816-18-3

Product Name: Phoxim

Synonyms: Phoxim-d5 (deuterated);4-Ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitril 4-sulfide;4-Ethoxy-7-phenyl-3,5-dioxa-8-aza-4-phospha-oct-6-ene-8-nitrile-4-sulfide;5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile,4-ethoxy-7-phenyl-4-sulfide;alpha-(((diethoxyphosphinothioyl)oxy)imino)-benzeneacetonitril;B 77488;b77488;BAY 5621

CAS: 14816-18-3

MF: C12H15N2O3PS

MW: 298.3

EINECS: 238-887-3

Product Categories: Agro-Chemicals;Organics;INSECTICIDE;AcaricidesPesticides&Metabolites;Alpha sort;Insecticides;NULL;N-PPesticides;OrganophorousAlphabetic;P;PER - POLA;Pesticides;Pesticides&Metabolites

Mol File: 14816-18-3.mol

Phoxim Structure

Phoxim Chemical Properties

Melting point 5.55°C

Boiling point bp0.01 102°

density d420 1.176

vapor pressure 2.1×10-3 Pa (20 °C)

refractive index nD20 1.5405

storage temp. 0-6°C

form liquid

Water Solubility 1.5 mg l-1 (20 °C)

InChIKey ATROHALUCMTWTB-WYMLVPIESA-N

CAS DataBase Reference 14816-18-3(CAS DataBase Reference)

NIST Chemistry Reference Phoxim(14816-18-3)

EPA Substance Registry System 3,5-Dioxa-6-aza- 4-phosphaoct-6-ene-8-nitrile, 4-ethoxy-7-phenyl-, 4-sulfide(14816-18-3)

Safety Information

Hazard Codes Xn;N,N,Xn

Risk Statements 22-50/53-62-43

Safety Statements 36-60-61-46-36/37

RIDADR UN 2810

WGK Germany 3

RTECS MD4740000

HazardClass 6.1(b)

PackingGroup III

HS Code 29269090

Toxicity LD50 orally in mice: >2000 mg/kg (Vinopal, Fukuto)

MSDS Information

Provider Language

4-Ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile 4-sulfide English

Phoxim Usage And Synthesis

Chemical Properties yellowish oily liquid, Specific gravity: 1.176 (20°C)

Uses Insecticide.

Uses Phoxim is used to control stored product insect pests in silos and barns. It is also used to control household insects such as ants and other public health pests. Agricultural targets include caterpillars and soil insects in maize, vegetables, cotton and potatoes.

Safety Profile Poison by ingestion. An experimental teratogen. When heated to decomposition it emits very toxic fumes of CN-, NO,, PO,, and SO,. See also NITRILES.

Metabolic pathway The primary metabolic step in the metabolism of phoxim in most biological systems is hydrolysis to the oxime, which may occur either oxidatively or via oxidative desulfuration followed by hydrolysis of the oxon which is much more hydrolytically labile. Stage II metabolism in plants involves the oxime group of the oxaminophenylacetonitrile moiety being reduced to an amine followed by its conjugation with malonic acid. Phoxim is one of a quite large group of insecticidal organophosphates which generates tetraethyl pyrophosphate and its thio analogues under the influence of light. These are compounds which are very active as acetylcholinesterase inhibitors and highly toxic to mammals.

Degradation Phoxim is relatively slowly hydrolysed in water. The half-lives at pH 4,7 and 9 were 26.7, 7.2 and 3.1 days, respectively (PM). Drager (1977) reported a half-life of 145 min in pH 11.5 50% aqueous propanol at 37 °C. It is gradually decomposed under UV irradiation (PM).

The photodecomposition of [32P]phoximon cotton leaves and glass plates was investigated by Drager (1971) who characterised the more hydrophobic organic-soluble components by TLC, GLC and 1H NMR and MS of the purified products. The cotton plants were irradiated with natural sunlight and mercury-vapour lamps at an average light intensity of 3500-4000 lux. On both glass plates and irradiated cotton leaves, phoxim was degraded relatively quickly to one major hydrophobic component, the concentration of which reached a maximum after about one day. This material was identified as the thiono-thiolo rearranged compound O,O-diethyl a-cyanobenzylideneamino-thiophosphorothioate (2). This transformation is an activation step as 2 is a highly active acetylcholinesterase inhibitor. No metabolite 2 was formed on cotton leaves placed in the dark so it can be considered to be a photochemical product rather than a plant metabolite. Additional minor metabolites were tetraethyl pyrophosphate (3) and O,O,O',O'-tetraethyl thiophosphorothioate (4) which formed to a greater extent on the glass plates rather than the cotton leaves.

Phoxim Preparation Products And Raw materials

Preparation Products Fenpropathrin+Phoxim,E.C.

Raw materials Etanol-->Methanol-->Sulfuric acid -->Sodium nitrite-->Triethylamine-->Chlorine-->Water-->Benzeneacetonitrile-->Phosphorus pentasulfide-->THIOPHOSPHORYL CHLORIDE-->Diethyl chlorothiophosphate-->Ethyl nitrite-->2-Cyanobenzyloxime

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