Fenthion

Description

Fenthion is a colorless oily liquid (technical grade, brown oily liquid 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 a yellow-to-brown oil.

The Uses of Fenthion

Fenthion is an organothiophosphate used as an insecticide. Fenthion is also a potent acaricide.

The Uses of Fenthion

antihypertensive

The Uses of Fenthion

Insecticide; acaricide.

The Uses of Fenthion

Insecticide for control of fruit ?ies, leaf hoppers and cereal bugs. Fenthion is also used as an acaracide.

What are the applications of Application

Fenthion is an organothiophosphate used as an insecticide

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 insecticidal activities.

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 skin absorption; use may be restricted, cholinesterase inhibitor. Toxic by skin absorption; questionable carcinogen.

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 for use in EU countries. Used in 20 countries including Australia. There are 23 global suppliers.

Trade name

B 29493®; BACID®; BAY 29493®; BAYCID®; BAYER 29493®; BAYER 9007®; BAYER S-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 involved in 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 sulfoxide which has a higher insecticidal activity than the parent compound. The subsequent oxidation of the sulfoxide to fenthion sulfone, the biological activity of which is considerably lower, is slow in plants but of major significance in animals. An additional route of bioactivation is through oxidative desulfuration to form fenoxon and, in all, five oxidative metabolites (fenthion sulfoxide, fenthon sulfone, fenoxon, fenoxon sulfoxide and fenoxon sulfone) have been detected in most biological systems. 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 to that of fenamiphos and although no studies have described the fate of the phenolic moiety for fenthion, it is likely that it will be metabolised by similar 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.

Degradation

Fenthion is stable in light, stable to acid and moderately stable to alkaline conditions. The DT₅₀s at pH 4, 7 and 9 were 223, 151 and 151 days respectively (PM).
The effect of the cuticular waxes of fruit upon the photodegradation of fenthion was studied by Cabras et al. (1997). Waxes were extracted with acetone and the fenthion added to the solution. The wax plus fenthion was applied as a film which was irradiated by natural sunlight. The analysis of fenthion and its metabolites was by GLC-FID (Cabras and Plumitallo, 1991). The potential metabolites synthesised were fenthion sulfoxide (2), fenthion sulfone (3), fenoxon (4), fenoxon sulfoxide (5) and fenoxon sulfone (6). Waxes from different fruits affected the decay rate, with wax from oranges and nectarines increasing the rate of decomposition but cuticular wax from olives retarding the rate. In all cases the products of photodegradation were fentluon sulfoxide (2), which steadily increased with time, and fenthion sulfone (3), which remained at a low but detectable level throughout the experiment. Minelli et al. (1996) exposed fenthion in glass jars to natural sunlight and analysed the photodegradation products by GLC-FID. The major product was fenthion sulfoxide (2) which very slowly degraded to the sulfone (3). This in turn was even more slowly photo-oxidised to fenoxon sulfone (6). The routes for the photodegradation of fenthion are shown in Scheme 1.

Toxicity evaluation

Acute oral LD₅₀ for rats: ca. 250 mg /kg

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 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

Hydrolysis and landfill for small quantities; incineration with flue gas scrubbing for large amounts. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office