Fenthion CAS 55-38-9
Introduction：Basic information about Fenthion CAS 55-38-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Fenthion Basic informationOverview Applications Mode of action Warning and Risk References
| Product Name: | Fenthion |
| Synonyms: | LEBAYCID;LEBAYCID(R);FENCHEM;FENTHION;FASTER;ENTEX(R);ENT 25540;BEILIULIN |
| CAS: | 55-38-9 |
| MF: | C10H15O3PS2 |
| MW: | 278.33 |
| EINECS: | 200-231-9 |
| Product Categories: | NITROPRESS;INSECTICIDE |
| Mol File: | 55-38-9.mol |
Fenthion Chemical Properties
| Melting point | 7.5°C |
| Boiling point | 87°C (0.01 mmHg) |
| density | 1.25 |
| vapor pressure | 7.4 x 10-4 Pa (20 °C) |
| refractive index | nD20 1.5698 |
| Fp | >100 °C |
| storage temp. | 2-8°C |
| solubility | Chloroform (Sparingly), DMSO (Sparingly) |
| form | liquid |
| Water Solubility | 0.0055 g/100 mL |
| Merck | 13,4030 |
| BRN | 1974129 |
| Exposure limits | OSHA PEL: TWA 0.2 mg/m3; ACGIH TLV: TWA 0.2 mg/m3 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | agriculture cleaning products cosmetics environmental food and beverages personal care |
| InChI | 1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3 |
| InChIKey | PNVJTZOFSHSLTO-UHFFFAOYSA-N |
| SMILES | COP(=S)(OC)Oc1ccc(SC)c(C)c1 |
| CAS DataBase Reference | 55-38-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Fenthion(55-38-9) |
| EPA Substance Registry System | Fenthion (55-38-9) |
Safety Information
| Hazard Codes | T;N,N,T,Xn,F |
| Risk Statements | 21/22-23-48/25-50/53-68-67-65-38-11 |
| Safety Statements | 36/37-45-60-61-62 |
| RIDADR | UN 2810/3017 |
| WGK Germany | 3 |
| RTECS | TF9625000 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29309090 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 2 Inhalation Acute Tox. 3 Dermal Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 Muta. 2 STOT RE 1 Oral |
| Hazardous Substances Data | 55-38-9(Hazardous Substances Data) |
| Toxicity | LD50 in male, female rats (mg/kg): 215, 245 orally (Gaines) |
| Overview | Fenthion is an organothiophosphate insecticide, avicide, and acaricide. Like most other organophosphates, it acts as a cholinesterase inhibitor[1, 2]. It has relatively low toxicity towards humans and mammals and is listed as moderately toxic compound in U.S. Environmental Protection Agency and World Health Organization toxicity class. However, it is highly toxic to birds. It can be used in agriculture and against mosquito larvae in tropical fresh waters[2, 3]. Fenthion is a contact and stomach insecticide, which can be used for the treatment of many sucking, biting pests, especially mosquitoes, fruit flies, stem borers, and Eurygaster cereal bugs. Specially, it is toxic to both the adult and immature forms[larvae] of the mosquitoes. Due to that it has been used extensively in the U.S. for controlling intestinal worms, fenthion no longer has FDA approval due to an excess number of poisoning deaths. Fenthion is available in dust, emulsifiable concentrate, granular, liquid concentrate, spray concentrate, ULV and wettable powder formulations[4]. |
| Applications | Fenthion is used for field and post-harvest treatment of various fruits, vegetables, and ornamentals[including sugar cane, rice, field corn, beets, pome and stone fruits, citrus fruits, pistachio, cotton, olives, coffee, cocoa and vines], for mosquito control in water and septic tanks, for pest control in commercial and domestic areas and as an ectoparasiticide in cattle[1, 2,5]. Fenthion is also used for quarantine control of Queensland fruit fly and other fruit flies through post-harvest treatments[dipping, flood sprays and non-recirculating low volume sprays]. It is highly effective in the treatment of various pests including fruit flies, leafhoppers, cereal bugs, stem borers, mosquitoes, animal parasites, mites, aphids, codling moths, and weaverbirds[6]. While it is effective as an insecticide, it is also moderately toxic to mammals, and highly toxic to birds. Based on its high toxicity to birds, fenthion is used in various parts of the world for weaverbird control. Pest control operators have used it to control pigeons around public buildings, as well. Once contacting bird, fenthion can subject to rapid absorption through the skin and killing birds. Acute symptoms of fenthion poisoning in birds include tearing of the eyes, foamy salivation, lack of movement, tremors, congestion of the windpipe, lack of coordination in walking, and an abnormally rapid rate of breathing or difficult breathing. It is usually applied as a paste to roosting areas when utilized for such purposes[6, 7]. Fenthion has also been tested in dogs and cows for possible control of parasites[8]. |
| Mode of action | Fenthion belongs to one of a class of insecticides referred to as organophosphates[1,9]. These chemicals act by interfering with the activities of cholinesterase, an esterase that lyses choline-based esters, several of which serve as neurotransmitters. Thus, it is either of two enzymes that catalyze the hydrolysis of these cholinergic neurotransmitters, such as breaking acetylcholine into choline and acetic acid. These reactions are necessary to allow a cholinergic neuron to return to its resting state after activation. Therefore, it is essential for the proper working of the nervous systems of both humans and insects[10, 11]. |
| Warning and Risk | Fenthion can provide both acute toxicity and chronic toxicity. Acute toxicity[12] It is moderately toxic if ingested, inhaled, or absorbed through the skin. It affects the central nervous, cardiovascular, and respiratory systems, and may irritate eyes and mucous membranes. When inhaled, the first effects may include bloody or runny nose, coughing, chest discomfort, difficult or short breath, and wheezing due to constriction or excess fluid in the bronchial tubes. Skin contact with organophosphates may cause localized sweating and involuntary muscle contractions. Eye contact will cause bleeding, tears, pupil constriction, pain, and blurred vision. Symptoms of acute exposure to organophosphate or cholinesterase-inhibiting compounds may also include the following: dizziness, tremor, nausea, abdominal cramps, sweating, blurred vision, headache, numbness, tingling sensations, incoordination, difficulty breathing or respiratory depression, and slow heartbeat. Very high doses may result in unconsciousness, incontinence, and convulsions or fatality[12]. Chronic toxicity Carcinogenic effectsThe National Cancer Institute performed carcinogenicity tests on fenthion that indicated that this insecticide might be a carcinogen in male mice. However, no carcinogenic effects were observed in other two-year feeding studies of rats and mice[13]. Reproductive effects-Single injections of 40 or 80 mg/kg of fenthion into the abdominal cavities of pregnant female mice caused poisoning in the developing fetuses, particularly when administered on days 10 through 12 of gestation. There were significantly more abnormalities in the offspring of female mice that had received 40 mg/kg on days 8 or 10 of pregnancy[14, 15]. Teratogenicity effects-Some reduction in fetal weight occurred, but no defects were found in mice that were given intraperitoneal doses of up to 80 mg/kg of fenthion in single day or 3-day periods during the period of gestation in which organs are formed[16]. |
| References |
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| Description | Fenthion is a colorless oily liquid (technical grade, brown oilyliquid with a mercaptan-like odor). |
| Chemical Properties | yellow brown oily liquid |
| Chemical Properties | Pure fenthion is a colorless liquid. Technical fenthion is a yellow or brown oily liquid with a weak garlic odor. It is insoluble or very sparingly soluble in water, but soluble in all organic solvents, alcohols, ethers, esters, halogenated aromatics, and petroleum ethers. It is grouped by the US EPA under RUP and hence requires handling by qualifi ed, certifi ed, and trained workers. Fenthion is used for the control of sucking and biting pests, i.e., fruit fl ies, stem borers, mosquitoes, and cereal bugs. In mosquitoes, it is toxic to both the adult and immature forms (larvae). The formulations of fenthion include dust, emulsifi able concentrate, granular, liquid concentrate, spray concentrate, ULV, and wettable powder. |
| Chemical Properties | Fenthion is a colorless liquid (when pure)with a weak, garlic-like odor. The technical grade is ayellow-to-brown oil. |
| Uses | Insecticide for control of fruit ?ies, leaf hoppers and cereal bugs. Fenthion is also used as an acaracide. |
| Uses | antihypertensive |
| Uses | Fenthion is an organothiophosphate used as an insecticide. Fenthion is also a potent acaricide. |
| Uses | Insecticide; acaricide. |
| Definition | ChEBI: An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen atom of the hydroxy group is replaced by a 3-methyl-4-(methylsulfanyl)phenyl group. It exhibits acaricidal and insecticidalactivities. |
| General Description | Yellow to tan oily liquid with a slight odor of garlic. |
| Reactivity Profile | Fenthion may react with strong reducing agents such as hydrides to generate highly toxic and flammable phosphine gas. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. |
| Hazard | Toxic by ingestion, inhalation, and skinabsorption; use may be restricted, cholinesteraseinhibitor. Toxic by skin absorption; questionablecarcinogen. |
| Health Hazard | Fenthion is moderately toxic to mammals, and highly toxic to birds. Exposures to fenthion cause poisoning with symptoms among occupational workers as observed with organophosphate pesticide-induced toxicity. These include, but are not limited to, numbness, tingling sensations, incoordination, headache, dizziness, tremor, nausea, abdominal cramps, sweating, blurred vision, diffi culty breathing or respiratory depression, and slow heart beat. Very high doses may result in unconsciousness, incontinence, and convulsions or fatality. Reports have indicated that exposures to fenthion cause adverse effects on the central and peripheral nervous systems, and the heart of exposed workers. |
| Fire Hazard | Fenthion is probably combustible. |
| Agricultural Uses | Insecticide, Larvicide, Veterinary medicine: Not registered for use in the U.S. Not approved foruse in EU countries. Used in 20 countries includingAustralia. There are 23 global suppliers. |
| Trade name | B 29493®; BACID®; BAY 29493®;BAYCID®; BAYER 29493®; BAYER 9007®; BAYERS-1752®; BAYTEX®; ENTEX®; LEBAYCID®;MPP®; MPP (pesticide) OMS 2®; PHENTHION®;PILARTEX®; QUELETOX®; S 1752®; SPOTTON®;SULFIDOPHOS®; TALODEX®; TIGUVON® |
| Potential Exposure | A potential danger to those involvedin the manufacture, formulation, or application of this agricultural chemical and pesticide; insecticide |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Speed in removing material from skinis of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If thischemical has been inhaled, remove from exposure, beginrescue breathing (using universal precautions, includingresuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit. Ifexposure and/or symptoms have occurred, the person shouldbe under medical observation for several days, as somesymptoms may be delayed. |
| Environmental Fate | Biological. From the first-order biotic and abiotic rate constants of fenthion in estuarine water and sediment/water systems, the estimated biodegradation half-lives were 22.4 and 3.9–14.5 days, respectively (Walker et al., 1988). Surface Water. In estuarine water, the half-life of fenthion was 4.6 days (Lacorte et al., 1995). Plant. In plants, fenthion oxidizes to the mesulfenfos and sulfone which further degrades to the sulfone phosphate before undergoing hydrolysis (Hartley and Kidd, 1987). Photolytic. Fenthion was oxidized to the corresponding sulfoxide and trace amounts (<5% yield) of sulfone when sorbed on soil and exposed to sunlight. The photosensitized oxidation was probably due to the presence of singlet oxygen. The degradation rate was higher in soils containing the lowest organic carbon (Gohre and Miller, 1986). Chemical/Physical. Stable at temperatures below 210°C (Worthing and Hance, 1991). Emits very toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987; Lewis, 1990). |
| Metabolic pathway | The major route of fenthion metabolism is by oxidation to the sulfoxidewhich has a higher insecticidal activity than the parent compound. Thesubsequent oxidation of the sulfoxide to fenthion sulfone, the biologicalactivity of which is considerably lower, is slow in plants but of majorsignificance in animals. An additional route of bioactivation is throughoxidative desulfuration to form fenoxon and, in all, five oxidativemetabolites (fenthion sulfoxide, fenthon sulfone, fenoxon, fenoxonsulfoxide and fenoxon sulfone) have been detected in most biologicalsystems. Hydrolysis, in contrast to most insecticidal phosphorothioates,appears to proceed via direct hydrolysis of fenthion rather than its oxon.The phenolic leaving group (3-methyl-4-thiomethylphenol) is identical tothat of fenamiphos and although no studies have described the fate of thephenolic moiety for fenthion, it is likely that it will be metabolised bysimilar routes to those described for fenamiphos. |
| storage | : Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with thischemical you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area away from oxidizers, alkalies and alkalinepesticides. A regulated, marked area should be establishedwhere this chemical is handled, used, or stored in compliance with OSHA Standard 1910.1045. |
| Shipping | UN3018 Organophosphorus pesticides, liquid,toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1;Labels: 6.1-Poisonous materials, Technical Name Required. |
| Toxicity evaluation | Acute oral LD50 for rats: ca. 250 mg /kg |
| Degradation | Fenthion is stable in light, stable to acid and moderately stable to alkalineconditions. The DT50s at pH 4, 7 and 9 were 223, 151 and 151 daysrespectively (PM). The effect of the cuticular waxes of fruit upon the photodegradation offenthion was studied by Cabras et al. (1997). Waxes were extracted withacetone and the fenthion added to the solution. The wax plus fenthionwas applied as a film which was irradiated by natural sunlight. Theanalysis of fenthion and its metabolites was by GLC-FID (Cabras andPlumitallo, 1991). The potential metabolites synthesised were fenthionsulfoxide (2), fenthion sulfone (3), fenoxon (4), fenoxon sulfoxide (5) andfenoxon sulfone (6). Waxes from different fruits affected the decay rate,with wax from oranges and nectarines increasing the rate of decompositionbut cuticular wax from olives retarding the rate. In all cases theproducts of photodegradation were fentluon sulfoxide (2), whichsteadily increased with time, and fenthion sulfone (3), which remained ata low but detectable level throughout the experiment. Minelli et al. (1996)exposed fenthion in glass jars to natural sunlight and analysed the photodegradationproducts by GLC-FID. The major product was fenthionsulfoxide (2) which very slowly degraded to the sulfone (3). This in turnwas even more slowly photo-oxidised to fenoxon sulfone (6). The routesfor the photodegradation of fenthion are shown in Scheme 1. |
| Incompatibilities | Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases,strong acids, oxoacids, epoxides, alkaline insecticides.Organothiophosphates are susceptible to formation ofhighly toxic and flammable phosphine gas in the presenceof strong reducing agents such as hydrideds and activemetals. Partial oxidation by oxidizing agents may result inthe release of toxic phosphorus oxides. |
| Waste Disposal | Hydrolysis and landfill forsmall quantities; incineration with flue gas scrubbing forlarge amounts. In accordance with 40CFR165, followrecommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by followingpackage label directions or by contacting your local or federal environmental control agency, or by contacting yourregional EPA office |
Fenthion Preparation Products And Raw materials
| Raw materials | Methanol-->Dimethyl sulfoxide-->Sulfur-->m-Cresol-->Petroleum crude oil-->Dimethyl disulfide-->Fenitrothion-->3-Methyl-4-(methylthio)phenol |
| Preparation Products | FENTHION-SULFOXIDE |
