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Phoxim

Phoxim Structure
CAS No.
14816-18-3
Chemical Name:
Phoxim
Synonyms
Foxim;PHOXIM;Phoxin;b77488;VOLATON;oms1170;Phoxime;Sebacil;sra7502;Valexon
CBNumber:
CB2255860
Molecular Formula:
C12H15N2O3PS
Molecular Weight:
298.3
MOL File:
14816-18-3.mol
Modify Date:
2024/7/22 17:51:23

Phoxim 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
solubility Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
Water Solubility 1.5 mg l-1 (20 °C)
form liquid
color Colorless to light yellow
Stability Hygroscopic, Moisture Sensitive
InChIKey ATROHALUCMTWTB-WYMLVPIESA-N
CAS DataBase Reference 14816-18-3(CAS DataBase Reference)
NIST Chemistry Reference Phoxim(14816-18-3)
EPA Substance Registry System Phoxim (14816-18-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H302-H311-H317-H330-H361f-H410
Precautionary statements  P201-P260-P273-P280-P304+P340+P310-P403+P233
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)

Phoxim Chemical Properties,Uses,Production

Description

Phoxim is a light yellow liquid, Solubility in water is 1.5 mg/L (20 ?C). It is readily soluble in most organic solvents and slightly in aliphatic hydrocarbons. Log Kow = 3.38. It is relatively slowly hydrolyzed in aqueous media; DT50 (22 ?C) at pH 4, 7, and 9 is 26.7, 7.2, and 3.1 d, respectively.

Chemical Properties

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

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.

Metabolism

Phoxim is oxidatively desulfurated to the oxon, which inhibits housefly AChE 270 times as quickly as bovine AChE. In mammals, the oxon is immediately hydrolyzed into diethyl hydrogen phosphate. The direct cleavage of the oxime ester bond of phoxim, the hydrolytic transformation of the nitrile group into carboxyl, and deethylation also contribute to the low mammalian toxicity. Elimination is very quick, 97% of the dose being excreted in the urine and feces in 24 h. Degradation in soils is also very rapid. By photochemical reactions, the thiooxime phosphate isomer, tetraethyl pyrophosphate, and its monothio analog are produced in small amounts on foliage.

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Benzoyl cyanide-0-(diethoxyphosphinothioyl)oxime BAYTHION BAYTHION(R) PHOXIM O,O-Diethyl O-(alpha-cyanobenzylideneamino)phosphorothioate O,O-DIETHYL-2-CYANOBENZYLIDENEAMINO-OXOPHOSPHONOTHIOATE 4-Ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile 4-sulfide ALPHA-[[(DIETHOXYPHOS-PHINOTHIOYL)OXY]IMINO]BENZENE-ACETONITRILE VOLATON VOLATON(R) OMS 1170 oms1170 (Diethoxy-thiophosphoryloxyimino)-phenyl acetonitrile (diethoxy-thiophosphoryloxyimino)-phenylacetonitrile 2-(Diethoxyphosphinothioyloxyimino)-2-phenylacetonitrile 3,5-Dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile, 4-ethoxy-7-phenyl-, 4-sulfide 3,5-Dioxa-6-aza-4-phospha-oct-6-ene-8-nitrile,4-ethoxy-7-phenyl-,4-sulfide bayer77488 baysra7502 Benzeneacetonitrile, [[(diethoxyphosphinothioyl)oxy]imino]- Benzeneacetonitrile, alpha-[[(diethoxyphosphinothioyl)oxy]imino]- Benzoyl cyanide O-(diethoxyphosphinothioyl)oxime benzoylcyanideo-(diethoxyphosphinothioyl)oxime ENT 27488 ent27488 Glyoxylonitrile, phenyl-, oxime O,O-diethyl phosphorothioate glyoxylonitrile,phenyl-,oxime,o,o-diethylphosphorothioate O,O-Diaethyl-O-(alpha-cyanbenzyliden-amino)-thionphosphat O,O-Diaethyl-O-(alpha-cyano-benzylidenamino)-monothiophosphat O,O-Diethyl alpha-cyanobenzylideneamino-oxyphosphonothioate O,O-Diethyl phosphorothioate, O-ester with phenylglyoxylonitrile oxime O,O-Diethyl-alpha-cyanobenzylidineaminooxyphosphonothiate O,O-Diethyl-O-(.alpha.-cyanobenzylideneamino)thiophosphate O,O-Diethyl-O-(-cyanobenzylideneamino)thiophosphate o,o-diethylphosphorothioate,o-esterwithphenylglyoxylonitrileoxime Phenylglyoxylnitrile oxime O,O-diethyl phosphorothioate Phenylglyoxylonitrile Oxime O,O-diethyl phosphorothioate phenylglyoxylonitrileoximeo,o-diethylphosphorothioate Phoxime Phoxin Sebacil sra7502 Valexon Valexone Volathion Volation Phosphorothioic acid O-(α-cyanobenzylideneamino) O,O-diethyl Phoxim 100mg [14816-18-3] Phoximsolution,100ppm phoxim,Valaxon O,O-Diethyl O-(alpha-cyanobenzylideneamino)phosphorothioate 4-Ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile 4-sulfide alpha-[[(Diethoxyphosphinothioyl)oxy]imino]benzeneacetonitrile 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