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Temephos

Temephos structure

Temephos 

structure
  • CAS No:

    3383-96-8

  • Formula:

    C16H20O6P2S3

  • Chemical Name:

    Temephos

  • Synonyms:

    Phosphorothioic acid,Op,Op′-(thiodi-4,1-phenylene) Op,Op,Op′,Op′-tetramethyl ester;Phosphorothioic acid,O,O′-(thiodi-p-phenylene) O,O,O′,O′-tetramethyl ester;Phosphorothioic acid,O,O′-(thiodi-4,1-phenylene) O,O,O′,O′-tetramethyl ester;Phosphorothioic acid,O,O-dimethyl ester,O,O-diester with 4,4′-thiodiphenol;EI 52160;Experimental Insecticide 52,160;Abate;Biothion;AC 52160;O,O,O′,O′-Tetramethyl O,O′-thiodi-p-phenylene phosphorothioate;Diphos (pesticide);Temephos;Difos;Difenphos;Diphos;Nephis;Temefos;Nephis 1G;Abathion;Ecopro 1707;Procida;Biothon;ENT 27165;Lavifos;Mosq;Azai-SS;Abate 4E;Mosquit TB 10;Mosquit TB 100;Temecal;O,O,O′,O′-Tetramethyl-O,O′-sulfanediylbis(1,4-phenylene)diphosphorothioate;53320-58-4

  • Categories:

    Active Pharmaceutical Ingredients  >  Other Chemical Drugs

Description

Abate is the trade name for Temephos, the known organophosphate larvicide. Abate is used to treat water infested with disease-carrying fl eas, to control mosquito, midge, and black fl y larvae. Abate quickly controls mosquito and other insect populations because it kills insect larvae before they mature, and the residual activity of abate prevents further insect populations. On decomposition, abate produces oxides of carbon, phosphorous, and sulfur. Temephos is a solid at ro


Temephos appears as white crystalline solid or liquid (above 87°F). Used as an insecticide. Technical grade is a viscous brown liquid. (NIOSH, 2016)|COLOURLESS OR WHITE CRYSTALS OR LIQUID.|White, crystalline solid or liquid (above 87°F).|White, crystalline solid or liquid (above 87°F). [insecticide] [Note: Technical grade is a viscous, brown liquid.]


Temephos appears as white crystalline solid or liquid (above 87°F). Used as an insecticide. Technical grade is a viscous brown liquid. (NIOSH, 2016)|Temephos is an organic sulfide that is diphenyl sulfide in which the hydrogen at the para position of each of the phenyl groups has been replaced by a (dimethoxyphosphorothioyl)oxy group. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide, an agrochemical and an ectoparasiticide. It is an organic thiophosphate, an organothiophosphate insecticide and an organic sulfide. It derives from a 4,4'-thiodiphenol.|Diphos has been used in trials studying the treatment of Plasmodium Falciparum Malaria.|An organothiophosphate insecticide.

Temephos Basic Attributes

466.47

466.47

222-191-1

ONP3ME32DL

0199

755842

3077|2783

DTXSID1032484

Colorless crystals|White, crystalline solid or liquid (above 87 degrees F) [Note: Technical grade is a brown, viscous liquid].

2930909061

Characteristics

145

6

Temephos appears as white crystalline solid or liquid (above 87°F). Used as an insecticide. Technical grade is a viscous brown liquid. (NIOSH, 2016)

1.3200

30.5 °C

248-257°F (Decomposes)

ABATE 4-E 167 deg F (Closed Cup); ABATE 6-E 109 deg F (Closed Cup); ABATE 200-E 113 deg F (Closed Cup); ABATE 500-E 142 deg F (Closed Cup)

1.612

0.003 g/100 mL

2-8°C

9.5×10 -6 Pa (20-25 °C)

Oral-Rat LD50: 1000 mg/kg; Oral-Mouse LD50: 223 mg/kg

Combustion produces toxic sulfur oxides and phosphorous oxide gases

Henry's Law constant = 1.2X10-9 atm-cu m/mole at 25 °C (est)

203.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|187.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Color: brown viscous liquid; density: 1.32; index of refraction: 1.586 to 1.588 at 25 °C/D. /Technical temephos/|Hydrolyzed by strong acids and alkalis|Amber viscous liquid; decomposes at 120-125 °C. /Technical (>90% pure)/|Optimum stability is at pH 5-7 and below 49 °C

No rapid reaction with air. No rapid reaction with water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Organothiophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Combustible Solid

Safety Information

III

6

UN 3077

3

21/22-51/53

22-37-61-60

TF6890000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Stable at 25 deg C for a least 2 years.

P260, P264, P270, P280, P302+P352, P305+P351+P338, P309+P311, P312, P314, P322, P332+P313, P337+P313, P363, P405, P501

H303

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|Hydrolysis: No hydrolysis was observed several hr at 40 °C and pH 11 or at pH 8 and room temp for several weeks. Essentially complete hydrolysis may be obtained upon heating in concentrated KOH /potassium hydroxide/ for 20 min. Recommendable method: Incineration. Peer-review: For large amt incineration in a unit with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|The following wastewater treatment technologies have been investigated for Malathion: Biological treatment and reverse osmosis. /Malathion/|Molten salt combustion: The melts contained either sodium carbonate or potassiumcarbonate. The use of potassium carbonate is of interest because the combustion product, potassium chloride can be used as a fertilizer. Destruction of the pesticide was greater than 99.9%. No pesticides were detected in the melt; however, traces of pesticides were detected in the off- gas. The conc of pesticides in the off-gas were generally well below the TLV. /Malathion/|Hydrolysis: The overalls polluted with malathion should be shaken and soaked in a soap-and-soda soln for 6-8 hr. Then the overalls must be washed 2-3 times in a hot soap-and-soda soln and rinsed carefully. Containers are decontaminated with 5% caustic or washing soda (300-500 g per 10 l of water). The containers are filled with this soln, kept for 5-12 hr, then washed with ample water. If soda is not at hand, wood ash may be used instead. /Malathion/

Incompatible with alkaline substances.|Strong acids, bases.

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Temephos (September 2000). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 28, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]|ANON; Temephos; Commission of the European Communities, 2920 Luxembourg, Grand Duchy of Luxembourg; International Programme on Chemical Safety (IPCS), World Health Organization, 1211 Geneve 27, Switzerland, p.2 (1991). International chemical safety card. Short term exposure effects: skin absorption; delayed effects; neurotoxic effects (cholinesterase inhibition). Long term exposure effects: cholinesterase inhibition.|USEPA; Reregistration Eligibility Decision (RED) Database for Temephos (3383-96-8). (September 2000).[Available from, as of May 1, 2009: http://www.epa.gov/oppsrrd1/REDs/temephos_red.htm]|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summary for Temephos (3383-96-8).[Available from, as of May 11, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|U.S. Environmental Protection Agency/Office of Pesticide Program's Chemical Ingredients Database on Temephos (3383-96-8).[Available from, as of May 22, 2009: http://npirspublic.ceris.purdue.edu/ppis/]

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)|Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (95.92%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P314, P322, P330, P361, P363, P391, P405, and P501|Aggregated GHS information provided by 49 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P302+P352, P305+P351+P338, P309+P311, P312, P314, P322, P332+P313, P337+P313, P363, P405, and P501|H311: Toxic in contact with skin [Danger Acute toxicity, dermal]|P260, P264, P270, P273, P280, P302+P352, P305+P351+P338, P309+P311, P312, P314, P322, P337+P313, P361, P363, P391, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. (NIOSH, 2016)|Pilots must use an enclosed cockpit and must wear chemical resistant gloves when entering or leaving an aircraft contaminated by pesticide residues. Used gloves must be stored in a closed chemical resistant container, such as a plastic bag, to prevent contamination of the inside of the cockpit.|When mixers and loaders use a closed system designed by the manufacturer to enclose the pesticide to prevent it from contacting handlers or other people and the system is functioning properly and is used and maintained in accordance with the manufacturer's written operating instructions, the handlers may wear long-sleeve shirt and long pants, shoes plus socks, chemical-resistant gloves and chemical-resistant apron, must wear protective eye wear if the system operates under pressure, and must have immediately available for use in an emergency, such as a broken package, spill, or equipment breakdown, all PPE necessary for mixers and loaders in the PPE section of this labeling.|Mixers, loaders, and applicators involved in hand-held spray applications must wear long-sleeved shirt and long pants, shoes and socks, chemical resistant gloves.|Aerial applicators and flaggers must wear long-sleeved shirt and long pants, shoes and socks, chemical resistant headgear (flaggers only).|For more Personal Protective Equipment (PPE) (Complete) data for TEMEPHOS (8 total), please visit the HSDB record page.|(See protection codes)

Combustible. Liquid formulations containing organic solvents may be flammable.

Water, foam, carbon dioxide, dry chemical. /Malathion/|Extinguish fire using agent suitable for type of surrounding fire. /Malathion/

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.|Environmental consideration: Landspill: Dig a pit, pond, lagoon, or holding areato contain liquid or solid material /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. /Malathion/|Environmental consideration: Water spill: If dissolved ... apply activated carbon at ten times the spilled amount /in region of 10 ppm or greater concentration/. Remove trapped material with suction hoses. Use mechanical dredges, or lifts to remove immobilized masses of pollutants and precipitates. /Malathion/|Spills of malathion on floors shall be absorbed with absorbing clay. Sweeping compound may be utilized to facilitate the removal of all visible traces of malathion contaminated clay. Equipment and fixtures contaminated with malathion shall be decontaminated with an alkaline solution (5% sodium hydroxide). /Malathion/|For more Cleanup Methods (Complete) data for TEMEPHOS (6 total), please visit the HSDB record page.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|This product may be applied only by public health officials, personnel of mosquito abatement districts, and other similar government agencies or personnel under contract to these entities.|The pesticide should only be applied when the potential for drift to adjacent sensitive areas (e.g. residential areas, non-target bodies of water, known habitat for threated or endangered species, non-target crops) is minimal (e.g. when wind is blowing away from the sensitive areas).|For more Preventive Measures (Complete) data for TEMEPHOS (13 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Temephos is slightly irritating to eyes but is not a skin irritant or a dermal sensitizer.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 15 mg/cu m. /Total dust/|Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 5 mg/cu m. /Respirable fraction/|Vacated 1989 OSHA PEL TWA 10 mg/cu m is still enforced in some states. /Total particulate/|Vacated 1989 OSHA PEL TWA 5 mg/cu m is still enforced in some states. /Respirable fraction/

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 mg/cu m, total particulate.|Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m, respirable fraction.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.

A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.

Cholinesterase inhibition. The substance may cause effects on the nervous system. This may result in convulsions and respiratory depression. The effects may be delayed. Medical observation is indicated. Exposure far above the OEL could cause death.

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

NO open flames.

PREVENT DISPERSION OF DUST! PREVENT GENERATION OF MISTS!

Use ventilation (not if powder), local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear face shield or eye protection in combination with breathing protection.

SEDIMENT: The concentration of temephos in sediment samples taken from several locations in NJ and CA, date not provided, were less then 0.1 ppm(1).

Toxicity

highly toxic

Mixture of abate and malathion are appreciably more toxic in rats than either compound alone.

LD50 Rabbit female dermal 970 mg/kg|LD50 Rabbit male dermal 1930 mg/kg|LD50 Rat oral male 8600 mg/kg|LD50 Rat oral female 13,000 mg/kg|For more Non-Human Toxicity Values (Complete) data for TEMEPHOS (15 total), please visit the HSDB record page.

/BIRDS and MAMMALS/ Signs of acute intoxication /from oral administration in birds/: asthenia, ataxia, low carriage, fluffed feathers, fasciculation, tremors, salivation, lacrimation, tracheal congestion, miosis, muscular weakness, tachycardia, tachypnea, tetany, immobility. ... Signs appeared as soon as 5 min & mortalities usually occurred between 1 & 24 hr after treatment ... . /Sample purity 92%/|/AQUATIC SPECIES/ The shrimp Leander tenuicornis is abundant in southeastern Queensland intertidal marsh pools and was chosen as an indicator species for toxicological studies with pesticides. Acute toxicity to this crustacean of temephos and 3 pesticide compounds under evaluation for registration in Australia (Bacillus thuringiensis var. israelensis, s-methoprene, and pyriproxyfen) was tested in 96-hr laboratory trials. Temephos was the most toxic compound, with a median lethal concentration (LC50) of 0.01 ppm (0.33 times the estimated field concentration [EFC] for a 15-cm-deep pool). ...|/AQUATIC SPECIES/ Laboratory evaluations were conducted in southeastern Queensland, Australia, to determine the toxicity of ... temephos ... to Culex annulirostris (Skuse), an Australian freshwater mosquito vector of arboviruses, and to Caradina indistincta Calman, a co-habiting nontarget shrimp species. ... The lethal dose ratio for temephos /was/ 0.05, suggesting that /it is/ environmentally unsuitable.|/AQUATIC SPECIES/ Laboratory studies were conducted to determine the sublethal effects of exposure to selected larvicides on the critical swimming speed of crimson-spotted rainbowfish, Melanotaenia duboulayi (Castlenau). This native fish is common throughout southeastern Queensland, and it is increasingly being distributed as a biological control agent of mosquitoes. The selected larvicides included ... temephos ... Exposure to temephos at 10 times the effective field concentration (EFC; 0.33 mg/L) ... resulted in a significant reduction in the /critical swimming speed/ of M. duboulayi under controlled conditions.|For more Ecotoxicity Excerpts (Complete) data for TEMEPHOS (13 total), please visit the HSDB record page.

Temephos' production may result in its release to the environment through various waste streams; its use as a pesticide to control the larvae of midges, blackfly, and mosquitoes, as well as controlling moths and flies(1) will result in its direct release to the environment(SRC). Temephos is applied directly to surface water in the case of midge, blackfly and mosquito control(2). Its use for controlling fleas on cats and dogs, and lice on humans(1) may also result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 18,250 to 31,800(2) indicate that temephos is expected to be immobile in soil(SRC). Volatilization of temephos from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Temephos is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). A biodegradation half-life of 17.2 days under aquatic conditions(2) suggests that biodegradation may be a moderately important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 18,250 to 31,800(2) indicate that temephos is expected to adsorb to suspended solids and sediment(SRC). Temephos has been reported to rapidly partition to sediment and suspended organic matter and become strongly adsorbed(3,4). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). According to a classification scheme(7), a BCF of 2,300(2) suggests bioconcentration in aquatic organisms is very high(SRC). A biodegradation half-life in water of 17.2 days under aerobic conditions(2) suggests that biodegradaton may be an important environmental fate process in water(SRC).|AQUATIC FATE: Temephos was added to pond water in beakers to give an initial concentration of 0.1 ppm. The dissipation was measured at temperatures of 10, 25 and 38 °C. Within 48 hours, the concentration of temephos in the pond water reached a steady state of 0.02-0.04 ppm with no significant difference observed for the three temperatures. The majority of temephos was found associated with organic matter in the pond water. Hydrolysis and oxidation may account for some of the dissipation; however, most of the temephos was adsorbed to organic matter and slowly released to achieve the steady state(1).|AQUATIC FATE: The time for 90% disappearance of temephos applied at 10 ppb to the surface of artificial polyethylene-lined ponds and activated by leaf litter (sediment) was 1.05 days. Ten days were required for a decline of temephos concentration to 0.01 ppb. Adsorption by polyethylene played a significant role in temephos disappearance, with a maximum of 1560 ppb adsorbed in <1 day. The rapid adsorption corresponded to rapid partitioning. This was followed by desorption from polyethylene, such that small amounts of insecticide were rereleased into the aqueous phase and, after a time, equilibrium was reached. The behavior of insecticides in artificial ponds may not completely reflect the behavior in natural systems(1).|For more Environmental Fate (Complete) data for TEMEPHOS (6 total), please visit the HSDB record page.

A base-catalyzed second-order hydrolysis rate constant of 5.4X10-4 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 106 and 105 days at pH values of 7 and 8, respectively(1). Hydrolysis of temephos at pH 5, 7, and 9 at a concentration of 30 ug/L showed no significant hydrolysis over a 30 day period(2). Under basic conditions, temephos hydrolyzes to 4,4'-thiodiphenol(3). It is hydrolyzed by alkalies and strong acids(4). Sunlight induced photolysis of 600 ppm temephos in methanol produced the corresponding sulfone and this reaction may also occur in sun lit natural waters(5). The reported half-life of C-14 labeled temephos under 24 hours of continuous irradiation (xenon arc lamp) is 15 days (k = 4.3X10-2 days), for 30 ug/L of temephos in unbuffered solutions at pH 6.5 to 7.0 and 25 °C(2). The predominant photolysis product was temephos sulfoxide at 11%(2).

A BCF of 2,300 was reported in a 28-day dynamic study of 120 acclimated fish exposed to C-14 labeled temephos at a concentration of 0.65 ug/L. Rapid uptake of temephos was observed and primarily intact temephos was detected. However, metabolism of the parent compound to temephos sulfoxide, was the major degradate. Detection of additional metabolites such as 4,4'-thiodiphenol, phosphorthioic acid, O-p-(p-hydroxyohenylthio)phenyl, O,O'-dimethyl ester and phosphoric acid, O-p-(p-hydroxypheny1thio)phenyl dimethyl ester were found(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

1.00e+05 L/kg|Freundlich adsorption coefficients calculated from adsorption/desorption studies ranged from 7.3-541 for temephos and was dependant upon organic carbon content of the soil. The Koc values for temephos were measured using 14-C labeled temephos at concentrations of 5, 8, 11, and 26 ppb. The results indicated Koc values in loamy sand (Delaware) 18,250, sandy loam (Princeton) 16,250, silt loam (Nebraska) 31,800, and loam (Ontario) 22,800. Temephos adsorption to sediment steadily increased to a maximum after two days of exposure, but temephos degradation products have shown to adsorb less strongly to soils(1). According to a classification scheme(2), these Koc values suggest that temephos is expected to be immobile in soil.

The Henry's Law constant for temephos is estimated as 2.0X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that temephos is expected to be essentially nonvolatile from water surfaces(2). The Henry's Law constant for temephos indicates that volatilization from moist soil surfaces is not expected(SRC). Temephos is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-8 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: The concentration of temephos in surface water samples taken from several locations in NJ and CA, date not provided, ranged from 2 to 11 ppb(1). After aerial application, the concentration of temephos in ponds was as high as 62 ug/L(2).

The concentration of temephos in California rice grain and foliage, date not provided, ranged from 0.01-0.07 and <0.01 ppm, respectively(1).

Occupational exposure to temephos may occur through inhalation of dust and dermal contact with this compound at workplaces where temephos is produced or used. Monitoring and use data indicate that the general population may be exposed to temephos via ingestion of some fish/seafood and drinking water, and dermal contact with consumer products containing this compound. Aerial application of temephos over aquatic sites may contaminate surface and drinking waters. (SRC)

Drug Information

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Dermal penetration of (14)C-labeled abate was measured in rats, rabbits, and dogs. Absorption was assessed by monitoring excreted radioactivity in urine and feces for 7 days and analysis of tissue specimens /were conducted/. Absorption would be expected to be less than 3% of applied dose. No evidence of bodily retention or pooling of radioactive moiety was demonstrated.|In guinea pig, /oral/ absorption apparently was less than in rat, & biliary excretion of metabolites was demonstrated.|When (3)H temephos was administered to rats by mouth, radioactivity reached a peak in the blood between 5 and 8 hr and then dissipated within a half-life of about 10 hr. Appreciable radioactivity was found only in the GI tract and fat. Both in the feces and in the fat, most of the radioactivity came from unchanged insecticide, but small amounts of the sulfoxide were present also. Traces of temephos were found in the urine ... .|In mammals, elimination of mainly of unchanged temephos in the feces and urine.

Studies with tritium-labeled abate indicated that this insecticide was relatively resistant to metabolic degradation. Residues on bean leaves ... consisted primarily of intact abate- about 70% of applied dose. The major metabolite was the sulfoxide derivative- less than 5% of the dose. Traces of sulfone derivative, oxygen analog, and glucosidic conjugates of phenolic hydrolysis products from abate and its sulfoxide & sulfone derivatives were also observed.|When rats were fed Abate, 60% of the material appeared in ... feces as the oxygen analog of Abate and its sulfoxide. The thiodiphenol, sulfinyldiphenol and sulfonyldiphenol were also found. In the urine, sulfate and glucoside conjugates of the hydrolysis products of Abate and sulfoxide as well as sulfone analogs accounted for 39.5% of the material administered. ... Five compounds found in feces and three in urine were not identified.|Larvae of the mosquito (Aedes aegypti L) metabolized Abate to sulfoxides and sulfones of Abate, the oxygen analog, and the demethylated analog. Some conjugates were also formed. In the housefuly, all expected metabolic products were found internally either as the intact ester or as hydrolyzed material ...|Abate yields in rat, abate sulfoxide and thiodiphenol. /From table/|For more Metabolism/Metabolites (Complete) data for TEMEPHOS (8 total), please visit the HSDB record page.

When (3)H temephos was administered to rats by mouth, radioactivity reached a peak in blood between 5 & 8 hr & then dissipated with half-life of about 10 hr.

Abate is a cholinesterase inhibiting insecticide.|Organophosphates poison insects and humans primarily by phosphorylation of the acetylcholinesterase enzyme at nerve endings. /Organophosphate Cholinesterase-inhibiting pesticides/

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, blurred vision; dizziness; dyspnea (breathing difficulty); salivation; abdominal cramps, nausea, diarrhea, vomiting Target Organs: Eyes, respiratory system, central nervous system, cardiovascular system, blood cholinesterase (NIOSH, 2016)

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.


Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Do not administer atropine or pralidoxime prophylactically to workers exposed to organophosphate pesticides. Prophylactic dosage with either atropine or pralidoxime may mask early signs and symptoms of organophosphate poisoning and thus allow the worker to continue exposure and possibly progress to more severe poisoning. Atropine itself may enhance the health hazards of the agricultural work setting: impaired heat loss due to reduced sweating and impaired ability to operate mechanical equipment due to blurred vision. This can be caused by mydriasis, one of the effects of atropine. /Organophosphate pesticides/|Re-exposures. Persons who have been clinically poisoned by organophosphate pesticides should not be re-exposed to cholinesterase inhibiting chemicals until symptoms and signs have resolved completely and blood cholinesterase activities have returned to at least 80 percent of pre-poisoning levels. If blood cholinesterase was not measured prior to poisoning, blood enzyme activities should reach at least minimum normal levels before the patient is returned to a pesticide contaminated environment. /Organophosphate pesticides/|Contraindications. The following drugs are contraindicated in nearly all organophosphate poisoning cases: morphine, succinylcholine, theophylline, phenothiazines, and reserpine. Adrenergic amines should be given only if there is a specific indication, such as marked hypotension. /Organophosphate pesticides/|Seizure control. Rarely, in severe organophosphate poisonings, convulsions occur despite therapy with atropine and pralidoxime. Insure that causes unrelated to pesticide toxicity are not responsible: head trauma, cerebral anoxia, or mixed poisoning. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for TEMEPHOS (21 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ Human volunteers each ingested 256 mg/day for 5 days or 64 mg/day for 4 weeks without symptoms or detectable effects on plasma or red cell cholinesterase activity.|/SIGNS AND SYMPTOMS/ Symptomatology: Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... Headache, giddiness, vertigo and weakness. Rhinorrhea and sensation of tightness in chest are common in inhalation exposure. Blurring or dimness of vision, miosis ... tearing, ciliary muscle spasm, loss of accommodation and ocular pain ... mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. Loss of muscle coordination, slurring of speech, fasciculations and twitching of muscles (particularly of tongue & eyelids), and generalized profound weakness. Mental confusion, disorientation and drowsiness. /Parathion/|/SIGNS AND SYMPTOMS/ Symptomatology: Difficulty in breathing, excessive secretion of saliva and of respiratory tract mucus, oronasal frothing, cyanosis, pulmonary rales and rhonchi & hypertension, (presumably due to asphyxia). Random jerky movements, incontinence, convulsions, and coma. Death primarily due to respiratory arrest arising from failure of respiratory center, paralysis of respiratory muscles, intense bronchoconstriction or all three. /Parathion/|/SIGNS AND SYMPTOMS/ Anorexia, nausea, vomiting, diarrhea, excessive salivation, pupillary constriction, bronchoconstriction, muscle twitching, convulsions, coma, respiratory failure.|For more Human Toxicity Excerpts (Complete) data for TEMEPHOS (6 total), please visit the HSDB record page.

Abate

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact

irritation eyes, blurred vision; dizziness; dyspnea (breathing difficulty); salivation; abdominal cramps, nausea, diarrhea, vomiting


Dizziness. Nausea. Muscle twitching. Sweating. Pupillary constriction, muscle cramp, excessive salivation. Vomiting. Diarrhoea. Laboured breathing. Convulsions. Unconsciousness.


MAY BE ABSORBED! Further see Inhalation.


Blurred vision.

Eyes, respiratory system, central nervous system, cardiovascular system, blood cholinesterase

Temephos Use and Manufacturing

Methods of Manufacturing

Reaction of 4,4'-thiodiphenol and o,o-dimethyl phosphorochloridothioate|Preparation: J. B. Lovell, R. W. Baer, BE 648531 C.C. 63, 11433e (1965); eidem, US 3317636 (1964, 1967 both to American Cyanamid).

Uses

Insecticide.

Production

(1972) 1.5X10+8 g (est)|(1974) Negligible (consumption)

38% as a larvicide on agricultural crops; 62% as a larvicide in other applications. (1971)

Granular and emulsifiable concentrate.|4 lb/gal EC; also 500 g/l (4.15 lb/gal); 50% water-dispersible powder (wdp); 1 sg insecticide (high density, sandcore granules ... For control of mosquito larvae in dense vegetation); 2g insecticide, 5g insecticide (low density granules for aquatic insect control in open waters and along shores).|Abate 4-E should be extended only with water or aromatic solvents containing at least 85 aromatics (such as Panasol AN-2 and Han 132). Granules 1, 2 & 5% AI. Granules 1%, 2%, 500 E EC, 50% WP.|Temephos is available as 10, 43, and 50% emulsifiable concentrates; 50% wettable powder; and 1, 2, and 5% granules.|For more Formulations/Preparations (Complete) data for TEMEPHOS (26 total), please visit the HSDB record page.

Phosphorothioic acid, Op,Op'-(thiodi-4,1-phenylene) Op,Op,Op',Op'-tetramethyl ester: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies Temephos (technical grade) as unlikely to present an acute hazard in normal use; Main Use: insecticide.|Temephos is approved by the WHO for the use as a vector control agent in potable water and recommended application should not exceed a dosage of 1 mg/L.|Where ... /Abate is/ used ... /to control mosquito larvae/, water so treated must not be drunk by humans, livestock or pets, or used in birdbaths or aquariums, at least until ... chem has become diluted to point of insignificance.

Method: OSHA PV2056; Procedure: high performance liquid chromatography using an ultraviolet detector; Analyte: temephos; Matrix: air; Detection Limit: 0.14 mg/cu m.|Method: USGS-NWQL O-2002-01; Procedure: gas chromatography-mass spectrometry; Analyte: temephos; Matrix: filtered natural-water; Detection Limit: 0.0361 ug/L.|Micro: Colorimetric method is based on the hydrolysis of abate to 4,4'-thiodiphenol & reaction with 4-aminoantipyrine & periodate, determination at 485 nm. Gas chromatographic determination of abate using FPD & ECD. Macro: Formulations assayed by GLC or by UV absorption after passage through silica gel.|Product analysis is by HPLC or by GLC. Residues may be determined by colorimetry or by GLC.|Temephos in pesticide formulations is determined by LC method at 254 nm. (Method is suitable for tech temephos and formulations with temephos as only active ingredient.)

Agrochemicals -> Insecticides|INSECTICIDES

Computed Properties

Molecular Weight:466.5
XLogP3:6
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:10
Exact Mass:465.98972587
Monoisotopic Mass:465.98972587
Topological Polar Surface Area:145
Heavy Atom Count:27
Complexity:474
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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