Phenthoate
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Phenthoate
structure -
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CAS No:
2597-03-7
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Formula:
C12H17O4PS2
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Chemical Name:
Phenthoate
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Synonyms:
Benzeneacetic acid,α-[(dimethoxyphosphinothioyl)thio]-,ethyl ester;Acetic acid,mercaptophenyl-,ethyl ester,S-ester with O,O-dimethyl phosphorodithioate;Acetic acid,mercaptophenyl-,ethyl ester,S-ester with O,O-dimethyl phosphorodithioate;Acetic acid,mercaptophenyl-,ethyl ester O,O-dimethyl phosphorodithioate;Phosphorodithioic acid,O,O-dimethyl ester,S-ester with ethyl mercaptophenylacetate;Bayer 18,510;ENT 23438;Cidial;Dimephenthoate;O,O-Dimethyl S-α-ethoxycarbonylbenzyl phosphorodithioate;Elsan;S-α-Ethoxycarbonylbenzyl dimethyl phosphorothiolothionate;Papthion;Phenthoate;Tsidial;L 561;BAY 33051;S-[α-(ethoxycarbonyl)benzyl] O,O-dimethyl phosphorodithioate;Montecatini L 561;Fenthoate;Pap;ENT 27386GC;Phendal;Cidemul;Bayer 18510;Tagson;Dhanusan 50;Shaluosong;61361-99-7;75513-84-7
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CAS No:
Description
ChEBI: An organic thiophosphate that is ethyl mandelate in which the hydroxy group has been replaced by a (dimethoxyphosphorothioyl)sulfanediyl group.
Phenthoate is an organic thiophosphate that is ethyl mandelate in which the hydroxy group has been replaced by a (dimethoxyphosphorothioyl)sulfanediyl group. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an acaricide and an agrochemical. It is an organic thiophosphate, an organothiophosphate insecticide and an ethyl ester.
Phenthoate Basic Attributes
320.36
320.36
219-997-0
DTXSID6042280
COLORLESS, CRYSTALLINE SOLID
29309090
Characteristics
102
4900
Colorless, crystalline solid. Aromatic.
1.226 g/cm3 @ Temp: 20 °C
17-18 °C
70-80 °C @ Press: 5 x 10-5-2 Torr
165-170 deg C
1.564
soluble in aromatic hydrocarbons, ketones, alcohols, chloroform, and carbon tetrachloride. Barely soluble in ... petroleum ether.
2-8°C
5.3×10 -3 (40 °C)
Oral-rat LD50: 71 mg/kg; Oral-Mouse LD50: 138 mg/kg
Open flame is flammable; heat decomposes toxic phosphorus oxide and sulfur oxide gas
AROMATIC
Decomposes when heated to 120 °C.|5X10-5 mbar @ 40 °C
Safety Information
III
6.1(b)
UN 2810
21/22-50/53
22-36/37-60-61
AI7875000
Xn,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Biological activity of the product remains practically unvaried for 2 years under environmental conditions, provided the product is stored in its unopened and undamaged original containers, in shaded and possibly well-aired places.
P260-P273-P280-P284-P304 + P340 + P310-P403 + P233
H302 + H312-H330-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Hydrolysis: Mix phenthoate with excess CaO /calcium oxide/ or NaOH /sodium /hydroxide/ and sand or other adsorbent in a pit or trench at least 0.5 m deep in a clay soil. Sodium hydroxide or Na2CO3 /sodium carbonate/ can also be added to the mixture to help speed the reactions when CaO is used as the main alkali. The amount of CaO or NaOH to use depends on the amount of pesticide to be disposed of and, to some extent, the concn of active ingredient in the pesticide and the actual chemical nature of the active ingredient. A practical guideline, in the absence of specific directions, is to use an approximate volume or weight of alkali from one-half to the same as that of the pesticide. For dilute formulations, such as a 1% soln or dust, the amount of CaO or NaOH can be reduced by one-half. For very concentrated pesticides (over 80% active ingredient) the amount of CaO or NaOH can be doubled, but the concentrate should be mixed first with water (or soapy water) before reaction with the alkali. For safety, a preliminary test should be made in which very small amounts of the pesticide and alkali are mixed and observed briefly to make sure it does not react too vigorously. Sizable quantities of pesticides can be disposed of in several smaller batches, rather than all at once, for added safety. Recommendable method: Incineration. Peer-review: Large amounts should be incinerated in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/|Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P312, P322, P330, P363, P391, and P501|Danger|H302+H312 (92.68%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]|P260, P264, P270, P271, P273, P280, P284, P301+P312, P302+P352, P304+P340, P310, P312, P320, P322, P330, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P281, P301+P310, P304+P312, P304+P340, P307+P311, P308+P313, P312, P314, P321, P330, P405, and P501
Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/|WORKERS HANDLING AND APPLYING ORGANOPHOSPHATE PESTICIDES (OPP) MUST ... BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES, AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. THE SIGNALMEN FOR AERIAL DUSTING OPERATIONS SHOULD BE EQUIPPED WITH A HAT AND CAPE MADE OF POLYVINYL CHLORIDE OR A FABRIC IMPREGNATED WITH A WATER REPELLENT. /PESTICIDES, ORGANOPHOSPHORUS/
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/
Avoid inhalation and contact with eyes and skin.|In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/|Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/|Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/|For more Preventive Measures (Complete) data for PHENTHOATE (9 total), please visit the HSDB record page.
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Organophosphorus pesticide, liquid, flammable, poisonous; Organophosphorus pesticide, liquid, flammable, toxic; Organophosphorus pesticide, liquid, poisonous, flammable; Organophosphorus pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for PHENTHOATE (16 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.
phenthoate was found in only a few out of 108 soil samples taken from a paddy field in 1982(1).
URBAN/SUBURBAN: Phenthoate was detected in ambient air in Kitakyushu at a total concentration of 1.3 ng/cu m for each of two sampling dates (July 21-22, 1991 and April 23-24, 1992)(1).
Toxicity
highly toxic
Phenthoate ... was rapidly hydrolyzed by rat liver and plasma carboxylesterases to the corresponding non-toxic metabolite, phenthoate acid. A partially purified enzyme isolated from rat liver microsomes was 7-fold more effective in hydrolyzed phenthoate than the microsomal fraction. O,S,S-Trimethyl phosphorodithioate (TMPDT) and O,O,S-trimethyl phosphorothioate (TMPT), 2 impurities present in technical formulations of phenthoate, were examined for their inhibiting effects on the esterase degradation of (phenyl-14)C-phenthoate in vitro. Incubation of (14)C-phenthoate with rat liver and plasma carboxylesterases in the presence of these impurities greatly diminished the amount of phenthoate acid formed. TMPDT was superior in its inhibitory action against rat liver carboxylesterase to that of TMPT. TMPDT was equipotent in inhibiting crude rat liver and plasma carboxylesterases than rat liver carboxylesterases.|The in vitro metabolism of phenthoate (O,O-dimethyl S-(alpha-(carboethoxy)benzyl)phosphorodithioate) was followed in rats after oral administration of a nontoxic dose of 100 mg/kg. The same metabolic study was conducted following coadministration of 0.5% O,S,S-trimethyl phosphorodithioate (OSS-Me). When administered alone, phenthoate was metabolized principally by carboethoxy ester hydrolysis and cleavage of the P-O and C-S bonds, resulting in at least 6 metabolites. The primary urinary metabolite excreted was phenthoate acid. Coadministration of 0.5% OSS-Me did not alter the types of metabolites excreted. However, a reduction of the carboxylesterase-catalyzed product (phenthoate acid) was observed, indicating that the enzyme responsible for the major pathway of phenthoate detoxication was inhibited.|The levels of total lipids, free fatty acids, cholesterol, and lipase activity were studied in selected tissues of Channa punctatus Bloch during individual and combined exposures of carbaryl and phenthoate. The total lipid levels decreased with elevated levels of free fatty acids and lipase activity during all exposures, suggesting increased lipid hydrolysis to derive energy as an attempt to face the pesticide toxic stress. The cholesterol levels showed an elevated trend. ... The effect produced by carbaryl + phenthoate treatment remained higher than either of the pesticides alone, suggesting the manifestation of an additive effect.|Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/|For more Interactions (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
LD50 MOUSE ORAL 350-400 MG/KG /TECHNICAL PRODUCT/|LD50 RAT ORAL 300-400 MG/KG /TECHNICAL PRODUCT/|LD50 Rat oral 77.7 mg/kg|LD50 Rat oral 118 mg/kg|For more Non-Human Toxicity Values (Complete) data for PHENTHOATE (10 total), please visit the HSDB record page.
Work ... must not be carried out by young persons under 18 yr, expectant or nursing mothers, or persons for whom work with toxic chemicals is contraindicated on account of their state of health; the same applies to alcoholics. Contraindications for work with organophosphorus pesticides are organic diseases of the CNS, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases and circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of the liver & kidneys, eye diseases (chronic conjunctivitis and keratitis). /Organophosphorus pesticides/
Phenthoate's former production and use as an insecticide/acaricide(1) would have resulted in its release to the environment through various waste streams(SRC).
Aquatic fate: ... Phenthoate was fairly stable in phosphate buffer with a half-life of approx 12 days at pH 8.0. Major hydrolysis products were phenthoate acid, demethylphenthoate, and demethylphenthoate oxone.|Terrestrial Fate: ... Phenthoate, in the form of an emulsifiable concentrate ... was applied to the citrus trees at 4 and 8 oz active ingredient/100 gal. Fresh fruit and soil exhibited typical first order decay for phenthoate, with levels after 7 days in peel < 1 ppm; pulp levels never exceeded 0.04 ppm (orange, 7 days). Maximum phenthoate soil levels occurred at the tree drip line near the surfate (0.55 ppm) but decayed to 0.12 ppm after 28 days; maximum oxon occurred at 14 days for these samples (0.04 ppm). Lemon peel oil, resulting from the 8 oz/100 gal treatment, incurred the highest phenthoate residues (16 ppm) as well as oxon (2.2 ppm). Wash water after-water rinse) contained negligible residues of phenthoate and oxon.|TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2420(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that phenthoate should have slight mobility in soil(SRC). Volatilization of phenthoate should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.48X10-9 atm-cu m/mole(SRC) calculated from experimental values for vapor pressure(4) and water solubility(5) but may occur from dry soil surfaces(SRC) based on an experimental vapor pressure of 2.6X10-6 mm Hg(4). The field half-life of phenthoate in soil has been determined to be 35 days(4). The values for the overall dissipation rate from soils (ks) for phenthoate are 0.0141, 0.0156, 0.0229, and 0.2865 per day for a clay, silt clay, sandy loam, and a fine loamy sand, respectively(6). Half-lives of phenthoate on foliage are 1.9, 1.5, 3.1, and 3.6 days on citrus, citrus, lemon, and orange crops, respectively(7). According to a Japanese MITI biodegradation test(8), biodegradation of phenthoate is not expected to be an important fate process in soil(SRC). However, soil biodegradation studies have shown that biodegradation in soil can occur within 30-75 days(9).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2420(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(1), indicates that phenthoate would adsorb to suspended solids and sediment(SRC) in the water. Phenthoate would be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 5.48X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(3) and water solubility(4). Experimental BCF values for phenthoate of 3.7-29 and 7.1-34 (carp)(5), 36 (topmouth gudgeon)(6), and 713 (willow shiners)(7) suggest that phenthoate will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(8). Phenthoate has estimated base-catalyzed hydrolysis half-lives of 2.4 years at pH of 8, and 24 years at a pH of 7(9). According to a Japanese MITI biodegradation test(5), biodegradation of phenthoate is not expected to be an important fate process in water(SRC). However, soil biodegradation studies have shown that biodegradation in soil can occur within 30-75 days(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenthoate, which has an experimental vapor pressure of 2.6X10-6 mm Hg at 25 °C(2), will exist as a vapor in the ambient atmosphere. Vapor-phase phenthoate is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 5 hours(3,SRC). Particulate-phase phenthoate may be physically removed from the air by wet and dry deposition(SRC). Sunlight causes phenthoate to undergo photochemical conversion of its P:S group to a P:O group with a rate of 0.0600/min and a conversion half-life of 11 minutes(4).
Hydrolysis: Phenthoate was fairly stable in phosphate buffer with a half-life of approx 12 days at pH 8.0. The major hydrolysis products were phenthoate acid, dimethylphenthoate, and demethylphenthoate oxone.|The rate constant for the vapor-phase reaction of phenthoate with photochemically produced hydroxyl radicals has been estimated as 7.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Sunlight causes phenthoate to undergo photochemical conversion of its P:S group to a P:O group with a rate of 0.0600/min and a decomposition half-life of 11 minutes(2). Phenthoate has an estimated base-catalyzed hydrolysis rate constant of 8.9X10-3 L/mol-sec which corresponds to a half-life of 2.4 years at pH of 8, and 24 years at a pH of 7(3).
48.98|Bioconcentration factor = 31 (calculated from water solubility by regression equations). /From table/|A six-week bioconcentration study using carp and phenthoate concentrations of 2.5 and 0.25 ug/l gave BCF values of 3.7-29 and 7.1-34, respectively(1). Another bioconcetration study using topmouth gudgeon in a continuous flow system gave a BCF value of 36(2). The BCF of phenthoate in the whole body of willow shiners after 168 hours was 713(3). An estimated BCF value of 375 was calculated for phenthoate(SRC), using an experimental log Kow of 3.69(4) and a recommended regression-derived equation(5). According to a recommended classification scheme(6), these BCF values suggest high bioconcentration in aquatic organisms(SRC).
1.00e+03 L/kg|KOC = 240 (calculated from water solubility by regression equations). /From table/|The Koc of phenthoate is estimated as approximately 2420(SRC), using an experimental log Kow of 3.69(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that phenthoate should have slight mobility in soil(SRC).
The Henry's Law constant for phenthoate is estimated as 5.48X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 2.6X10-6 mm Hg(1), and water solubility, 200 mg/l(2). This value indicates that phenthoate will be essentially nonvolatile from water surfaces(3,SRC). Phenthoate's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicates that volatilization from water, and dry and moist soil surfaces should not occur(SRC).
The insecticide phenthoate, was applied to ricefields in Sardinia at rates equivalent to maximum aqueous concn of 0.4-2.8 mg/kg, assuming the water to be 20 cm deep. The concn in water were measured by high-performance liquid chromatography. Residues in 162 water samples, collected from 16 ricefields 1, 4, 7, 10, 12, 18, 21, and 120 days after the last spraying, were all below the limit of determination (0.03 mg/kg). Residues in 40 water samples taken from 5 drainage canals were also < 0.03 mg/kg.|SURFACE WATER: After treatment of citrus trees with 4 lb/gal emulsifiable phenthoate, water samples from a nearby pond (30 m away) had the following average concentrations: not detected 1 day before application, 140 ppb 3 hours after application, 21.8 ppb 1 day after application, and 2.2 ppb 9 days after application(1).
Phenthoate was found as a residue in food during the FDA regulatory monitoring of 30361 and 27700 commercial food samples during the years 1978-1982(1) 1983-1986(2), respectively. Phenthoate was found infrequently in leaf and stem vegetables (2 samples in 1975), in vine and ear vegetables(118 samples in 1974-76), in root vegetables (1 sample in 1975)(3). Phenthoate was detected during the FDA's 1990 regulatory monitoring study of imported and domestic foods(4).
Occupational exposure to organophosphorus pesticides, such as phenthoate, can occur through ingestion, inhalation, and dermal contact(1).
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.)
Most organophosphate compounds are ... absorbed from skin, conjunctiva, gastrointestinal tract, & lung. /Organophosphate compounds/|The rate of dermal absorption /of organophosphorus pesticides/ may be ... influenced by the solvent used. /Organophosphorus pesticides/|Many of the organophosphorus insecticides are excreted in the milk ... /Organophosphorus insecticides/|Following their absorption, most organophosphorus cmpd are excreted almost entirely as hydrolysis products in the urine. /Anticholinesterase agents/|For more Absorption, Distribution and Excretion (Complete) data for PHENTHOATE (6 total), please visit the HSDB record page.
ELSAN DEGRADED RAPIDLY IN /CABBAGE SEEDLING, STRAWBERRY & APPLE FRUIT/ ... & WAS HYDROLYZED TO NON-TOXIC DERIVATIVES. MAIN METABOLITES ... WERE ELSAN CARBOXY DERIVATIVES, MANDELIC ACID & BIS(CARBETHOXYBENZYL)DISULFIDE.|MAJOR URINARY METABOLITES /OF PHENTHOATE IN MICE/ @ DOSAGE OF 30 MG/KG WERE THE O-DEMETHYLATED ACID (25.8%), THE O-DEMETHYLATED OXON ACID (18.4%) & DIMETHYL PHOSPHORODITHIONATE (16.9%). INITIAL PRODUCT OF P-S CLEAVAGE ... WAS FURTHER METABOLIZED INTO CORRESPONDING SULFIDE, MANDELIC ACID, & S-METHYLATED DERIV.|In plants, there is oxidation to the thiophosphate, followed by hydrolysis. Identified metabolites are phosphoric acid, dimethyl and monomethyl phosphate.|Five metabolites were detected in the plasma and urine of a patient following ingestion of the organophosphate insecticide, phenthoate. Intact phenthoate was detected only in gastric lavage fluid. After methylation of acidic extracts of plasma and urine, phenthoate acid, demethyl phenthoate, demethyl phenthoate oxon acid, demethyl phenthoate S-isomer, and demethyl phenthoate acid S-isomer were identified with synthesized phenthoate analogues by gas chromatography and gas chromatograph-mass spectrometry. The main metabolites were phenthoate acid and demethyl phenthoate oxon acid. Although demethyl phenthoate oxon acid was a significant metabolite, no phenthoate oxon, phenthoate oxon acid or demethyl phenthoate oxon were detected. If the oxon was formed in the patient, it may have been rapidly degraded by carboxylesterase or glutathione transferase to demethyl phenthoate oxon acid.|For more Metabolism/Metabolites (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
0.18 Days
Cholinesterase inhibitor.|The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/|Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase. ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/|The main feature of the toxic mechanism of organophosphorus pesticides is inhibition of the esterase enzyme activity, in particular of cholinesterase, which plays an important physiological part. Organophosphorus pesticides can also indirectly interact with the biochemical receptors of acetylcholine. /Organophosphorus pesticides/|For more Mechanism of Action (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
A comatose patient who is diaphoretic, has pinpoint pupils and the odor of an insecticide on clothing or breath, and is noted to have muscle fasciculations represents the classic presentation of organophosphate poisoning. ... Specific steps in management include the following. 1. Decontamination. ... 2 Airway. Establish an airway if necessary. ... 3. Respiratory Status. Respiratory distress, in fact, is commonly found in these patients from multiple causes. ... 4. Cardiac Monitoring. ... 5. Cholinesterase Level. ... 6. Pralidoxime. Pralidoxime is the treatment of choice for organophosphate poisoning and should be used for nearly all patients with clinically significant orgnophosphate poisoning, particularly whose patients with muscular fasciculations and weakness. ... 7. Atropine. Atropine is the physiologic antidote for organophosphate poisoning. A trial dose of atropine should be instituted on clinical ground when one suspects organophosphate intoxication. /Organophosphate poisoning/|Atropine is the antidote of choice as in organophosphate poisoning. Although the total amount of atropine required usually is less, the same initial doses are recommended. Pralidoxime usually is necessary and may reduce the effectiveness of atropine (especially with carbaryl). ... Patients require approximately 6-12 hr of atropine treatment, but all significantly poisoned patients should be observed at least 24 hr after the last atropine dose. /Organophosphate poisoning/|1. INSURE THAT A CLEAR AIRWAY EXISTS BY ASPIRATION OF SECRETIONS IF NECESSARY. ADMIN OXYGEN BY MECHANICALLY ASSISTED PULMONARY VENTILATION IF RESPIRATION IS DEPRESSED. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMIN ATROPINE TO MINIMIZE RISK OF VENTRICULAR FIBRILLATION. IN SEVERE POISONINGS, IT MAY BE NECESSARY TO SUPPORT PULMONARY VENTILATION MECHANICALLY FOR SEVERAL DAYS. 2. ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE. ... IN MODERATELY SEVERE POISONING: ADULT DOSAGE AND CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG BODY WEIGHT. /ORGANOPHOSPHATE PESTICIDES/|2. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWO OR MORE TIMES THE DOSAGES SUGGESTED ABOVE MAY BE NEEDED. THE DOSE OF ATROPINE MAY BE INCREASED AND THE DOSING INTERVAL DECREASED AS NEEDED TO CONTROL SYMPTOMS. CONTINUOUS INTRAVENOUS INFUSION OF ATROPINE MAY BE NECESSARY WHEN ATROPINE REQUIREMENTS ARE MASSIVE. REVERSAL OF MUSCARINIC SYMPTOMS AND SIGNS, NOT AN ARBITRARY DOSE LIMIT, IS THE DESIRED END-POINT. PRESERVATIVE-FREE ATROPINE PRODUCTS SHOULD BE USED WHENEVER POSSIBLE. NOTE: PERSONS NOT POISONED OR ONLY SLIGHTLY POISONED BY ORGANOPHOSPHATES MAY DEVELOP SIGNS OF ATROPINE TOXICITY FROM SUCH LARGE DOSES. FEVER, MUSCLE FIBRILLATIONS, AND DELIRIUM ARE THE MAIN SIGNS OF ATROPINE TOXICITY. IF THESE APPEAR WHILE THE PATIENT IS FULLY ATROPINIZED, ATROPINE ADMINISTRATION SHOULD BE DISCONTINUED, AT LEAST TEMPORARILY, WHILE THE SEVERITY OF POISONING IS REEVALUATED. /ORGANOPHOSPHATE PESTICIDES/|For more Antidote and Emergency Treatment (Complete) data for PHENTHOATE (10 total), please visit the HSDB record page.
A 40% wettable powder of phenthoate was applied to the inside surfaces of houses at a rate of 2 g/sq m. Five spraymen and one mixer applied the material during 5-6 hr/day for three consecutive days. The Nigerian village treated contained 213 homes and 172 other buildings. No complaints related to phenthoate toxicity were elicited from the operators, and they showed no significant decrease in whole blood cholinesterase activity. There were no complaints from the 384 inhabitants of the village and, in a group of over 30 who were tested on day 1 and again on day 10, there was no enzyme inhibition ...|/IT HAS BEEN/ ... DEMONSTRATED THAT IMPURITIES PRESENT IN TECHNICAL GRADE SAMPLES OF ... PHENTHOATE POTENTIATE TOXICITY ... THUS ACCOUNTING FOR GREATER TOXICITY OF TECHNICAL SAMPLES AS COMPARED TO HIGHLY PURIFIED SAMPLES.|All the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/|The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/|For more Human Toxicity Excerpts (Complete) data for PHENTHOATE (17 total), please visit the HSDB record page.
Cidial
Phenthoate Use and Manufacturing
Preparation of ethyl α-bromophenylacetate At 30 °C, slowly drop 70 mol of more than 95% phosphorus trichloride into a mixture of 192 mol phenylacetic acid and 40 L of dichloroethane. After the drop, the reaction was refluxed for 30 min. Continue stirring for 1h. Then, under reflux, 250 mol of absolute ethanol was added dropwise within 1 to 1.5 hours, the drop was completed, and the stirring reaction was continued for 1 hour to end the esterification. After alkaline washing, extraction, neutralization, water washing and solvent removal, the reaction liquid was obtained as brownish red liquid α-bromobenzene ethyl acetate 45kg, content above 91%, yield 87.7%. For the preparation of O, O-dimethyl dithiophosphate, see the preparation method of dimethoate. In the synthesis of Dafengfeng, 160 mol O, O-dimethyl sodium dithiophosphate aqueous solution treated with Na2CO3 was added with 30 L of toluene, and the temperature was raised to 40 to 45°C. A phase transfer catalyst was added, and 100 mol of dropwise was added within 0.5 to 1 h. After the ethyl α-bromophenylacetate was dripped, the reaction was incubated at 65℃ for 4h. After alkaline washing, neutralization, water washing, and solvent removal, red-yellow oily rice paddy crude oil was obtained with a content of 92% and a yield of 88%. .
Phenthoate is an organothiophosphate insecticide used against lepidoptera and houseflies.
FOR AGRICULTURAL USE. EMULSIFIABLE CONCENTRATE, WETTABLE POWDER, OIL SOLUTION, DUST, GRANULES.|EMULSIFIABLE CONCENTRATE--5% ACTIVE INGREDIENT; DUST-1.5, 2 & 3% ACTIVE INGREDIENT. ... ELSAN MICRO GRANULE 3--3% ACTIVE INGREDIENT ...|THE TECHNICAL GRADE /IS/ (90-92%) PURE ... FOR AGRIC USE: 'CIDIAL 50L', LIQUID (500 G TECH/KG); 'CIDIAL OIL', (50 G TECH + 800 G MINERAL OIL); 'CIDIAL WP40', WP (400 G/KG); 'CIDIAL D', DUST (30 G/KG); 'CIDIAL GRANULES', GRANULES (20 G/KG); 'CIDIAL AS', LIQUID (850 G/KG); 'CIDIAL ULV', ULTRA LOW VOL CONCENTRATE (1 KG/KG). FOR MOSQUITO CONTROL: 'TANONE 50L', LIQUID (500 G/KG); 'TANONE AS', LIQUID (850 G/KG); 'TANONE ULV', ULTRA LOW VOL CONCENTRATE (1 KG/KG).|BAY 33051|For more Formulations/Preparations (Complete) data for PHENTHOATE (28 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies Phenthoate (technical grade) as Class II: moderately hazardous; Main Use: insecticide.|... BRITISH PATENT 834 814; US PATENT 2 947 662.|/IT PROVIDES/ BROAD SPECTRUM OF EFFECTIVENESS ON ... (TEA, MULBERRY, TOBACCO) ...|GOOD IMMEDIATE ACTIVITY WITH BROAD SPECTRUM INCLUDING RICE STEM BORER, GREEN RICE LEAF HOPPER, AND BLACK RICE BUG. ... NON-PHYTOTOXIC TO ALMOST ALL CROPS.|For more General Manufacturing Information (Complete) data for PHENTHOATE (7 total), please visit the HSDB record page.
A rapid and simple method is developed for the determination of organophosphorus pesticides in unpolished rice. The new method incorporated acetonitrile-water (1 + 1) extraction, removal of fats by zinc acetate, and further cleanup on an activated charcoal chromatographic column. The higher fatty acids in the extract react rapidly with zinc acetate to form insoluble zinc carboxylates, which precipate. Additional interferneces were cleaned up on an activated charcoal chromatographic column, and organophosphorus pesticides absorbed on the activated charcoal were eluted with acetone-hexane. ... Pesticides are measured by flame photometric gas chromatography. Recoveries from 50 g unpolished rice samples fortified with 5-50 ug diazinon, 6-30 ug parathion, 8-40 ug fenitrothion and IBP, 10-50 ug dimethoate and fenthoate, 20-100 ug malathion, or 40-200 ug EPN (O-ethyl-O-p-nitrophenyl-phenyl phosphonothioate) ranged from 75.7 to 95.8%|A procedure allowing direct simultaneous separation and detection of herbicides in rice cultivation was developed utilizing a Hibar RP8 column and a Varian 5020 liquid chromatograph equipped with a Valco AH 20 automatic injector. The column was developed with buffer-acetonitrile (40:60-30:70) (phosphate buffer, pH 4.00-3.50) with detection limits of 0.01-0.03 ppm for ... phenthoate.|Organosulfides in aromatic vegetables such as onion, Welsh onion, leek, garlic, and shallot strongly interfere with the analysis of residual organophosphorus pesticides by flame photometric detector (FPD)-GLC. The removal of the interfering substances in onion was investigated using column chromatography. Extraction with acetonitrile, concn of the extreact, and cleanup on an Amberlite XAD-8 column and FPD-GLC was used. Sulfides were efficiently removed to allow the good recovery of /82% of the phenthoate/ ... added to onion samples ... . The method was also used for the analysis of residual organophosphorus pesticides in Welsh onion and leek.|An analytical procedure for the analysis of phenthoate ... and its oxon was described for fresh grapefruit, lemons, and oranges and for 15 fractionated products and soil.|For more Analytic Laboratory Methods (Complete) data for PHENTHOATE (10 total), please visit the HSDB record page.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:320.4
XLogP3:3.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:320.03058836
Monoisotopic Mass:320.03058836
Topological Polar Surface Area:102
Heavy Atom Count:19
Complexity:324
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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