299-84-3

Basic information

• Product Name: FENCHLORPHOS
• Synonyms: KORLAN(R);ETROLENE;FENCHLORPHOS;DOW ET-14;RONNEL;RONNEL(R);O,O-DIMETHYL O-(2,4,5-TRICHLOROPHENYL) PHOSPHOROTHIATE;O,O-DIMETHYL-O-[2,4,5-TRICHLOROPHENYL]-PHOSPHOROTHIOATE
• CAS NO: 299-84-3
• Molecular Formula: C₈H₈Cl₃O₃PS
• Molecular Weight: 321.55
• EINECS: 206-082-6
• Product Categories: Alpha sort;E-GAlphabetic;F;FA - FLPesticides;Insecticides;Organophorous;Pesticides&Metabolites
• Mol File: 299-84-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 41.0℃
• Boiling Point: 97at0.01mmHg
• Flash Point: -18 °C
• Appearance: /solid
• Density: 1.485 g/cm3 (25 ºC)
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.5585 (589.3 nm 20℃)
• Storage Temp.: APPROX 4°C
• Solubility: Soluble in acetone, carbon tetrachloride, ether, kerosene, methylene chloride, and toluene (Windholz et al., 1983)
• Water Solubility: 0.00 g/100 mL
• Merck: 13,8337
• BRN: 1885571
• CAS DataBase Reference: FENCHLORPHOS(CAS DataBase Reference)
• NIST Chemistry Reference: FENCHLORPHOS(299-84-3)
• EPA Substance Registry System: FENCHLORPHOS(299-84-3)

Safety Data

• Hazard Codes: Xn,N,F
• Statements: 21/22-50/53-67-65-38-11
• Safety Statements: 25-36/37-60-61-62
• RIDADR: UN 1145 3/PG 2
• WGK Germany: 3
• RTECS: TG0525000
• Hazardous Substances Data: 299-84-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 299-84-3 differently. You can refer to the following data:
1. Powder or granules. Insoluble in water; soluble in most organic solvents.
2. Ronnel is a white to light tan crystalline solid.

Uses

Different sources of media describe the Uses of 299-84-3 differently. You can refer to the following data:
1. Insecticide.
2. Systemic insecticide in livestock

General Description

White to light-tan crystalline solid. Mp: 41° C, Density :1.49 g cm-3 at 25°C. Biocidal (toxic to all animal life in differing degrees) by its action as a cholinesterase inhibitor. Used as an insecticide. Degrades readily in the environment by hydrolysis and oxidation.

Reactivity Profile

FENCHLORPHOS is non-flammable and non-combustible. Decomposes with heating to evolve toxic and corrosive vapors (hydrogen chloride, phosphorus oxides, sulfur oxides). Incompatible with strong oxidizing agents.

Hazard

Toxic by ingestion and inhalation. Cholinesterase inhibitor, use may be restricted. Questionable carcinogen.

Health Hazard

Ronnel is a weak cholinesterase inhibitor and has low toxicity. On both single and repeated doses, ronnel affects the pseudoesterase of the plasma rather than the true acetylcholinesterase of the red blood cells.Ronnel has not been shown to potentiate the effect of other commonly used organophosphorus insecticides.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. A cholinesterase inhibitor. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, POx, and SOx. See also PARATHION and CHLOROPHENOLS.

Potential Exposure

Ronnel is both an organochlorine and organophosphorus compound; potential danger to those involved in manufacture, formulation and application of this insecticide for farm (livestock) and household uses. Degrades readily in the environment by hydrolysis and oxidation .

Environmental Fate

Chemical/Physical. Though no products were identified, the reported hydrolysis halflife at pH 7.4 and 70°C using a 1:4 ethanol/water mixture is 10.2–10.4 hours (Freed et al., 1977). Ronnel decomposed at elevated temperatures on five clay surfaces, each treated with hydrogen, calcium, magnesium, aluminum and iron ions. At temperatures <950°C (125, 300 and 750°C), bentonite clays impregnated with technical ronnel (18.6 wt %) decomposed to 2,4,5-trichlorophenol and a rearrangement product tentatively identified as O-methyl S-methyl-O-(2,4,5-trichlorophenyl) phosphorothioate (Rosenfield and Van Valkenburg, 1965). At 950°C, only the latter product formed. It was postulated that this compound resulted from an acid-catalyzed molecular rearrangement reaction. Ronnel also undergoes base-catalyzed hydrolysis at elevated temperatures. Products include methanol and a new compound that is formed via cleavage of a methyl group from one of the methoxy groups, which is then bonded to the sulfur atom (Rosenfield and Van Valkenburg, 1965). Ronnel is stable to hydrolysis over the pH range of 5–6 (Mortland and Raman, 1967). However, in the presence of a Cu(II) salt (as cupric chloride) or when present as the exchangeable Cu(II) cation in montmorillonite clays, ronnel is completely hydrolyzed via first-order kinetics in <24 hours at 20°C. The calculated half-life of ronnel at 20°C for this reaction is 6.0 hours. It was suggested that decomposition in the presence of Cu(II) was a result of coordination of the copper atom through the oxygen or sulfur on the phosphorus atom resulting in the cleavage of the side chain containing the phosphorus atom forming O,O-ethyl-O-phosphorothioate and 1,2,4-trichlorobenzene (Mortland and Raman, 1967). Emits very toxic fumes of chlorides, sulfur and phosphorus oxides when heated to decomposition (Lewis, 1990).

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2783 Organophosphorus pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo- sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Store at temperatures ＜25-30℃. Organothiophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrideds and active metals. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides

Waste Disposal

Incineration with added flam- mable solvent in furnace equipped with afterburner and alkali scrubber . In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesti- cide containers. Must be disposed properly by following package label directions or by contacting your local or fed- eral environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C8H8Cl3O3PS/c1-13-15(12,14-2)16-8-4-6(10)5(9)3-7(8)11/h3-4H,1-2H3

Upstream product

• 16805-78-0 thiophosphorodichloridic acid O-(2,4,5-trichloro-phenyl) ester 
• 95-95-4 2,4,5-trichlorophenol 
• 4901-40-0 O,O-dimethyl O-(2,4-dinitrophenyl) phosphorothioate 
• 2463-84-5 dicapthon 
• 298-00-0 parathion-methyl 
• 90003-76-2 Dimethyl-<2,4,5-trichlor-phenyl>-phosphit 
• 2524-03-0 dimethyl chlorothiophosphate 
• 122-14-5 MEP 

Downstream Products

• 152-18-1 O,O,O-trimethylthiophosphate 
• 95-95-4 2,4,5-trichlorophenol 
• 3983-45-7 ronnel oxon 
• 7141-72-2 Triaethyl-methyl-phosphonium S-methyl-O-<2,4,5-trichlor-phenyl>-thiophosphat 
• 46417-28-1 O-Methyl-O-<2,4,5-trichlor-phenyl>-thiophosphorsaeure 
• 7016-89-9 Tributyl-methyl-phosphonium S-methyl-O-<2,4,5-trichlor-phenyl>-thiophosphat 
• 7016-84-4 Tripropyl-methyl-phosphonium S-methyl-O-<2,4,5-trichlor-phenyl>-thiophosphat 

Relevant articles and documents

Mechanisms of abiotic degradation and soil-water interactions of pesticides and other hydrophobic organic compounds. Part 3. Nucleophilic displacement at the phosphorus centre of the pesticide fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl) phosphorothioate] by oxygen nucleophil...

Rate constants for the reaction of the title compound, 1, with a number of oxygen nucleophiles, including structurally related phenoxides and oxygen-based α-nucleophiles, have been measured in aqueous solution at 25 deg C. A significant α-effect was observed, confirming participation of the nucleophile in the rate-limiting step of the reaction as well as indicating different transition states (TS) for the reaction of α-nucleophiles compared to normal ones. The Broensted-type correlation of log kNu vs. pKa of nucleophiles shows a linear plot for the series of structurally related phenoxides in the pKa range 5.4-10.0, straddling the pKa of the leaving group (3-methyl-4-nitrophenoxide, pKa 7.20), but is curved in the highly basic region corresponding to CF3CH2O- and HO- as nucleophiles. The slope of the linear portion of the plot (βNu) is 0.49 (R2 0.988). The linearity of the plot for the series of structurally related phenoxides is consistent with a concerted mechanism for nucleophilic attack at the P center of the substrate. A value of β1g -0.39 (R2 0.973) is measured for the reaction of PhO- with substituted phenyl dimethyl phosphorothioate esters. Combining the values of βNu and β1g gives βeq = 0.88; these parameters when considered together with the effective charge distribution in the TS, demonstrate that the TS for the symmetrical reaction (in which nucleophile = leaving group = 3-methyl-4-nitrophenoxide) has no significant phosphorylium ion character. The Leffler index points to a concerted reaction in which bond formation is slightly ahead of bound rupture in the TS. Data from the present study are compared with literature data for (thio)phosphoryl group transfer. We propose that, unless special structural and/or environmental features prevail, (thio)phosphoryl transfers between phenoxides are more likely to occur via a concerted mechanism. It is shown that the TS for the concerted transfer of (EtO)2P=O between two PhO- moieties shows more pentacoordiante intermediate character than the symmetrical reaction of 1 due to differences in (i) basicity of PhO- versus 3-CH3,4-NO2PhO-, and (ii) abilities of O and S in the P=X (X = O, S) moiety to stabilize the incoming negative charge.

Alkyl 4-[o-(substituted methyleneamino)phenyl]-3-thioallophanates

Various alkyl 4-[o-(substituted methyleneamino)phenyl] 3-thioallophanates are useful as fungicides and mite ovicides. The compounds are prepared by reacting alkyl 4-(o-aminophenyl)-3-thioallophanates with aldehydes or trialkyl orthoformates. Some of the compounds are prepared by further reacting the reaction product of an alkyl 4-(o-aminophenyl)-3-thioallophanate and a trialkyl orthoformate with a primary or secondary amine. Exemplary species are methyl 4-[o-(o-fluorobenzylideneamino)phenyl]-3-thioallophanate, methyl 4-[o-(4-methylbenzylideneamino)phenyl]-3-thioallophanate and methyl 4-[o-(2-furfurylideneamino)phenyl]-3-thioallophanate.