Phosalone
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Phosalone
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CAS No:
2310-17-0
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Formula:
C12H15ClNO4PS2
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Chemical Name:
Phosalone
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Synonyms:
Phosphorodithioic acid,S-[(6-chloro-2-oxo-3(2H)-benzoxazolyl)methyl] O,O-diethyl ester;Phosphorodithioic acid,O,O-diethyl ester,S-ester with 6-chloro-3-(mercaptomethyl)-2-benzoxazolinone;NIA 9241;RP 11974;O,O-Diethyl S-[6-chloro-3-(mercaptomethyl)-2-benzoxazolinone]phosphorodithioate;Phosalone;Phosalon;Zolone PM;Zolone;Zolone 35EC;Phosphorodithioic acid O,O-diethyl S-[(6-chloro-2-oxobenzoxazolin-3-yl)methyl] ester;Chipman 11974;Benzophosphate;S-[6-Chloro-3-(mercaptomethyl)-2-benzoxazolinone] O,O-diethyl phosphorodithioate;3-(O,O-Diethyldithiophosphorylmethyl)-6-chlorobenzoxazolinone;6-Chloro-3-(O,O-diethyldithiophosphorylmethyl)benzoxazolone;S-(6-Chloro-2-oxobenzoxazolin-3-yl)methyl diethyl phosphorothiolothionate;Rubitox;Agria 1060;Zolone Flo;Fosalon;KB insectes;Fozolone;11129-09-2;12650-35-0;29562-46-7;54182-71-7
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CAS No:
Description
Phosalone is a member of the organophosphate family of insecticides. It is used as both an insecticide and acaricide.
Solid|COLOURLESS OR WHITE CRYSTALS WITH CHARACTERISTIC ODOUR.
Phosalone is a member of the class of 1,3-benzoxazoles carrying a [(diethoxyphosphorothioyl)sulfanyl]methyl group at the nitrogen atom, an oxo group at position 2 and a chloro group at position 6. It is an organothiophosphate insecticide. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an acaricide and an agrochemical. It is an organothiophosphate insecticide, an organochlorine insecticide, a carbamate ester and a member of 1,3-benzoxazoles.
Phosalone Basic Attributes
367.81
367.81
218-996-2
448B85HT8M
0797
2783
DTXSID1024259
Crystals|White|Colorless
2934999021
Characteristics
105
4.3
Solid
1.39 g/cm3
47.5-48 °C
446.7±55.0 °C at 760 mmHg
100 °C
1.609
Solubility in water, g/100ml at 25°C: 0.0003 (very poor)
0-6°C
Vapour pressure at 25°C: negligible
Oral-rat LD50: 85 mg/kg; Oral-Mouse LD50: 73 mg/kg
Decomposes toxic phosphorus oxide, sulfur oxide, nitrogen oxide, chloride gas by heating
Garlic
Henry's Law constant = 3.94X10-7 atm-cu m/mole at 25 °C (est)
Hydrolyzed by strong alkalis and acids|Hydroxyl radical reaction rate constant = 2.38X10-10 cu cm/molec-sec at 25 °C (est)
Non-corrosive
Safety Information
III
6.1(b)
2783
3
21-25-50/53-43-20/21
36/37-45-60-61
TD5175000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable under normal laboratory conditions for a period of 2 years.
P261-P273-P280-P301 + P310 + P330-P302 + P352 + P312-P304 + P340 + P312
H301 + H311-H317-H332-H410
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 ... : Mix phosalone with excess lime and sand or other adsorbent ... . Sodium carbonate can be added to the mixture to help speed the reactions when lime is used as the main alkali. ... (Peer-review conclusions of an IRPTC expert consultation (May 1985))
EPA/OPP; Organophosphorus Cumulative Risk Assessment - 2006 Update. p 40. (August 2006) Downloadable as a zipped pdf file from http://www.epa.gov/pesticides/cumulative/2006-op/index.htm as of June 20, 2007 provides a comparative risk assessment of organophosphorus pesticides and evaluates the risk posed by existing exposure scenarios.|EPA/OPP; Finalization of Interim Reregistration Eligibility Decisions (IREDs) and Interim Tolerance Reassessment and Risk Management Decisions (TREDs) for the Organophosphate Pesticides, and Completion of the Tolerance Reassessment and Reregistration Eligibility Process for the Organophosphate Pesticides. Memorandum dated July 31, 2006 indicates that the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) are indeed eligible for reregistration; and (2) the pesticide tolerances covered by the IREDs and TREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) meet the safety standard under Section 408(b)(2) of the FFDCA. The phosalone TRED was completed in 2001.|USEPA/Office of Pesticide Programs; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Phosalone p.12 EPA 738-R-01-001 (January 2001). EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of June 15, 2007: http://www.epa.gov/pesticides/reregistration/status.htm]
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P333+P313, P363, P391, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 201 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P307+P311, P309+P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P311, P312, P314, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501
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 pestices, solid, NOS/
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.|A STUDY WAS CONDUCTED TO PROVIDE INFORMATION FOR THE ESTABLISHMENT OF A WORKER REENTRY PERIOD. HEALTH SCIENTISTS RECOMMENDED 21 DAY REENTRY INTERVAL ON THE BASIS ON THIS STUDY.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, NOS/|Personnel protection: Keep upwind. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, NOS/|For more Preventive Measures (Complete) data for PHOSALONE (6 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 PHOSALONE (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.
/Phosalone/ is moderately irritating to the skin and eyes.
Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Separated from food and feedstuffs. Well closed. Keep in a well-ventilated room. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
A harmful concentration of airborne particles can be reached quickly.
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 could cause death. The substance is mildly irritating to the eyes and skin.
Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms. Repeated or prolonged contact may cause skin sensitization.
NO open flames.
PREVENT DISPERSION OF DUST!
Avoid inhalation of dust and mist. Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection if powder.
SOIL: The concn of phosalane in 15 cm sandy loam soil cores taken from test plots sprayed at 1050 g/ha and 2100 g/ha was 0.293 and 1.18 ppm shortly after application, 0.165 and 0.493 ppm 6 days after application, and 0.072 and 0.121 ppm 14 days after application(1).
Toxicity
highly toxic
Rats were given chlorpromazine (I) (0.02 mg/day, orally), zolone (II) (0.0386 mg/day, orally), or both drugs together for 5 wk. Histological and histochemical study of liver tissue showed both morphological and enzymological damage resulting from drug treatment. Combination treatment caused more damage than treatment with I or II alone. I appears to be a hepatotoxin, and the increased alteration of hepatocytes after combination treatment may be the result of a II-induced increase in metabolism of I, with rapid formation of hepatotoxic free radicals.
LD50 Rat male oral 120-170 mg/kg|LD50 Mouse oral 180 mg/kg|LD50 Guinea pig oral 380 mg/kg|LD50 Rat percutaneous 1500 mg/kg|For more Non-Human Toxicity Values (Complete) data for PHOSALONE (9 total), please visit the HSDB record page.
/AQUATIC SPECIES/ The level of acetylcholinesterase (AChE) in brain regions of /the tropical fish/ Oreochromis mossambicus at different intervals showed the extent of phosalone toxicity. Significant inhibition of AChE at the end of 96 hr in the brain regions was observed. In contrast to AChE inhibition, the monoamine oxidase (MAO) activity showed significant increase in the regions of cerebral hemispheres, dien/mesencephalon, cerebellum and medulla oblongata. The increase of MAO activity in the brain regions under phosalone toxicity is considered to be one of the mechanisms to maintain the amines level in O. mossambicus.|/AQUATIC SPECIES/ Effect of multiple sublethal concentrations of phosalone on whole animal and kidney oxygen consumption, hematological indices and serum enzymes of freshwater fish, Oreochromis mossambicus, were carried out over a 90 day exposure period. Significant changes were observed which have been indicating that the presence of hypoxic condition in the biosystem, gradual increase in the rate of synthesis of hemoglobin and disruption of liver function during the toxicity of phosalone.|/OTHER TERRESTRIAL SPECIES/ /Phosalone is one of the/ Group II: moderately toxic pesticides (LD50 2.0 to 10-99 ug/bee): These can be used in the vicinity of bees if dosage, timing, the method of application are correct, but should not be applied directly on bees in the field or at colonies.|/OTHER TERRESTRIAL SPECIES/ An acute dose of phosalone, an organophosphate pesticide, widely used in crop fields, injected to Rana tigrina, intraperitoneally, inhibited the different inorganic ion linked ATPase enzymes of the central nervous system (CNS). Six discrete CNS compartments, namely telencephalon, mid-brain, rhombencephalon, cervical spinal cord, thoracic spinal cord and lumbar spinal cord showed markedly diminished ATPase activity. ATPases inhibition affected the neuronal activity and muscular coordination leading to moribund or comatose phase in the poisoned frogs. The specific inhibition of Mg(2+)-ATPase suggests the uncoupling action of the compound in the neuronal tissue. Increased oxygen uptake in the brain regions of phosalone-treated frogs also supports the above uncoupling action.|For more Ecotoxicity Excerpts (Complete) data for PHOSALONE (6 total), please visit the HSDB record page.
Phosalone's production may result in its release to the environment through various waste streams; its former use as an insecticide and acaricide(1) resulted in its direct release to the environment(SRC). Phosalone cannot be produced, distributed, or sold in the US however its use is approved in many countries throughout Europe and Asia(1).
TERRESTRIAL FATE: Based on a classification scheme(1), a Koc range of 1,800(2) to 12,608(3), indicates that phosalone is expected to have slight to negligible mobility in soil(SRC). Volatilization of phosalone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Phosalone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.5X10-8 mm Hg(SRC), determined from a fragment constant method(5). Slow mineralization (0.5-2.5% of 14-CO2 in 84 days) when incubated under anaerobic conditions in moist or flooded soil(6) indicates that biodegradation is not an important environmental fate process in soil(SRC).|TERRESTRIAL FATE: IN SOIL, INITIAL STAGES WERE APPARENTLY SAME AS IN PLANTS. HOWEVER RED MATERIAL WAS OBSERVED & IDENTIFIED AS SUBSTITUTED PHENOXAZONE. DISULFIDE FORMED BY OXIDATION OF PHOSPHORODITHIOATE.|TERRESTRIAL FATE: If sprayed on plants, phosalone persists for about 14 hr, being converted into the corresponding phosphorothioate which is rapidly hyrolyzed(1). Another study showed that half-life of phosalone applied to apples, grapes and alfalfa was 2.5, 9.9-16.0, and 4.0 days, respectively(3). When (phenyl-14C) phosalone was uniformly incorporated into moist (75% field capacity) and flooded Matapeake loam and Monmouth fine sandy loam at 10 ppm and incubated at 22 °C, it was found that the field half-life in soil was 3-7 days with loss attributed to extensive binding and condensation(2).|TERRESTRIAL FATE: An analysis of soil extracts and volatilized material, indicate that volatilization was not a major loss mechanism (<0.1%). After 85 days in moist soil, 8.5% and 9.9% of phosalone was converted to CO2, 16.9 and 11.2% were extractable residues, and 74.9 and 79.3% were bound residues. For the flooded soils the values were 0.5 and 2.7%, 11.9 and 11.2%, and 87.6 and 88%, respectively. The bound fraction was primarily associated with the fulvic acids in soil. Approximately 8% of the extractable 14C remaining in the moist Matapeake soil after 85 days was phosalone(2). Based on the products identified in soil, a metabolic pathway was proposed in which phosalone undergoes extensive binding and condensation in soil, similar to many aniline-based herbicides. Metabolism proceeds by oxidation of the phosalone to the oxon, cleavage of the O,O-diethyl methyl phosphorodithioate linkage to form 6-chloro-2-benzoxalinone, and opening of the heterocyclic ring followed by condensation to form 2-amino-7-chloro-3H-phenoxazin-3-one(1), the same dimer formed from 4-chloroaniline in soil(3).|For more Environmental Fate (Complete) data for PHOSALONE (7 total), please visit the HSDB record page.
The rate constant for the vapor-phase reaction of phosalone with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Phosalone is relatively stable to hydrolysis in neutral and acid solution, but hydrolyzes in alkaline solutions to 6-chloro-2-oxobenzoxazole and diethylphosphorothioic acid(2). Approximately 25% of phosalone applied to moist soil in the laboratory and kept in the dark as a control for a photolysis experiment, hydrolyzed to 6-chloro-2-oxobenzoxazole in 15 days(2). It was not clear whether the hydrolysis was microbially mediated. A hydrolysis rate of 0.00350/day has been reported(3), corresponding to a half-life of 198 days(SRC). Phosalone contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC). A photolysis rate of 0.69/day(4) has been reported(3), corresponding to a half-life of approximately one day(SRC). Sunlight reacts with phosalone resulting in the first order conversion of P=S to P=O to form phosalone-oxon(5). The rate constant and half-life for this reaction in air is 0.0081 1/min and 86 min, respectively(5). Under controlled laboratory conditions, the half-life of phosalone under simulated solar light was 4.75 days on a soil surface and 8.5 days on a glass surface(2). It is not clear whether an appreciable fraction of phosalone sprayed onto crops is present in the vapor phase(SRC).|... PERSISTS ON PLANTS FOR ABOUT 14 HR BEING CONVERTED TO THE CORRESPONDING PHOSPHOROTHIOATE WHICH IS RAPIDLY HYDROLYZED.
An estimated BCF of 470 was calculated in fish for phosalone(SRC), using a log Kow of 4.38(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).|Soil treated with phosalone and aged 84 days was introduced into a model ecosytem and the bioaccumulation of phosalone determined in algae, snails, daphnids (Daphnia magna) and mosquito fish (Gambusa affinis). The BCF was about 300(1) which indicates a high potential for bioaccumulation(2). However, phosalone was toxic to daphnids and fish and therefore the results may not be valid.|In a model ecosystem, phosalone was concentrated to a moderate level in fish and to lower levels in snails and algae. Several metabolites were observed but not identified.
426.58 L/kg|A Koc value for phosalone of 1,800 has been reported(1). Values arrived at using various soils from Australia ranged from 2,587 (pH 7.6, OC 10.2 g/kg, clay 210 g/kg) to 6,078 (pH 5.1, OC 20.0 g/kg, clay 40 g/kg) to 12,608 (pH 7.2, OC 23.2 g/kg, clay 879 g/kg) with one outlier at 85,528. This latter soil is characterized as being rich in proteinaceous material and containing abundant alkyl and methoxy groups(2). According to a classification scheme(3), these Koc values suggest that phosalone is expected to have low mobility or be immobile in soil. In thin layer chromatography experiments, phosalone was practically immobile in 4 soils (Rf was 0.02-0.07)(4). It was more mobile in a fifth soil, a Lakeland sandy loam (Rf = 0.26)(4). The Freundlich K values for phosalone adsorbed to two pond sediments were 12.05 and 28.90, respectively(3). The Freundlich 1/n values were 0.54 and 0.66, respectively(3). The non-linear nature of the isotherms suggests that the sorption process is complex and there are different types of binding sites(3). A possible explanation for this behavior is phosalone's hydrolysis and subsequent formation of strongly bound condensation products(6).|(14)C-Labeled phosalone was nearly immobile in leaching studies with four soils but moved somewhat in Lakeland sandy loam. When aged in aerobic and flooded soils, phosalone was not appreciably mobile but some radioactivity streaked to high Rf values. Phosalone predominated in the streak but there were unidentified materials present also.|(14)C-labeled phosalone was incorporated into moist and flooded Matapeake loam and Monmouth fine sandy loam. Disappearance from these soils was rapid and appeared as (14)C-bound soil residues. Ring cleavage accounted for only a small (ca. 8.5%) amount of the loss and volatilization was negligible. From (14)C-ring-labeled phosalone, 79% of (14)C was bound to soil and distributed in fulvic acid, humic acid, and humin. Polar metabolites were the major metabolites in flooded soils but were not identified. In addition to phosalone, three compounds were identified with MS as phosalone oxon, 6-chloro-2-benzoxazolinone and 2-amino-7-chloro-3H-phenoxazin-3-one. The half-life of phosalone was calculated to be between 3 and 7 days.
The Henry's Law constant for phosalone is estimated as 3.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that phosalone is expected to be essentially nonvolatile from water surfaces(2). Phosalone did not volatilize from distilled water in a 15 day static test(3). No phosalone volatilization occurred from a glass plate in 1 hr(4). Phosalone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.5X10-8 mm Hg(SRC), determined from a fragment constant method(5).
GROUNDWATER: In a survey of farm wells in Ontario, Canada, 103 in 1986 and 76 in 1987, phosalone was not detected in any wells at a detection limit of 0.5 ug/L(1). However, phosalone was only used on crops in 2 farms in 1986 and none in 1987(1). In a similar survey of 84 farms in Southern Ontario in 1984, phosalone was also not detected(2). However, only one farm used phosalone. Phosalone levels exceeded 0.1 ug/L in samples sites of North-west Bulgaria collected in 1998(3). Phosalone was not detected in three California wells sampled in 1995 as part of a well water update survey(4).|SURFACE WATER: Phosalone was not detected in the Hogeveense Polder, an area of flower bulb cultivation, sampled monthly from August, 1989 through January, 1990(1).|RAIN/SNOW/FOG: Phosalone tested positive in 6% of 205 rain water samples collected from the intense agricultural region of the Axios River Basin, Greece in 1997-1998 with a range of 0.01 to 0.43 ug/L and a mean of 0.07 ug/L (limit of detection 0.005 ug/L)(1). The maximum annual deposition is 14.0 ug/sq m(1).
In FDA's pesticide monitoring of foods for 1978-1982, phosalone residues were found in 10 of the 1044 composite samples analyzed(1). In FDA's pesticide monitoring program for 1983-1986, 63 of the 3744 samples analyzed contained phosalone(2). For 1985-1991, FDA analyzed pesticide residues in foods eaten by infants and children(3). The protocol mandated using whole, unwashed, and unpeeled fruit. For domestic produce, phosalone residues were found in 36 of 2464 samples of apples and 6 of 571 samples of pears. The maximum residues were 3.1 ppm in apples and 0.93 ppm in pears. For imported foods, phosalone was found in 25 of 735 samples of apples and 4 of 816 samples of pears. The maximum residues were 0.45 ppm in apples and 0.10 ppm in pears.|In FDA's Total Diet Study of 27 market baskets of infant foods and adult foods eated by infants and children for 1985-91, phosalone residues were found in the following food items (number of findings, maximum residue in ppm): Oatmeal with apples and bananas (2,0.005); Dutch apple/apple betty (3,0.043); fruit dessert with tapioca (2,0.003); custard pudding (1,0.008); apple sauce (11,0.026); peaches (8,0.18); pears/pears and pineapple (15,0.085); raw apples (3,0.110); and applesauce (3,0.004)(1). From 1982 to 1986, the FDA Los Angeles District laboratory found phosalone in 3 out of 6391 samples of domestic and 7 out of 12,044 samples of imported food and feed; all residues were found on grapes(3). One residue was between 1 and 2 ppm, while the others were <0.5 ppm(3). In a 1980-84 fruit monitoring program in Ontario, Canada, phosalone was found in 10 of 26 composite samples of sweet cherries at a mean concentration of 0.25 ppm(2).|Phosalone was not found on 354 Ontario-grown vegetable composites analyzed between 1980 and 1985(2). Phosalone was not one of the most commonly found pesticides according to FDA's 1990 Total Diet Study (i.e., fewer than 9 of the 936 samples contained phosalone)(1). Phosalone was not found on any of the 6970 produce samples tested in San Antonio from 1989-1991 above the 2 ppm detection limit(3). Phosalone residues were only detected in the fruit category in FDA's Total Diet studies(1-2). In the FY 1981/1982 Adult Total Diet Study, the mean concn of phosalone in the fruit category was 0.0074 ppm, with 4 positive composites containing 0.017-0.087 ppm phosalone(5). The mean concn in the fruits and fruit juices category in the analogous infant and toodler study was 0.0035 ppm(4).|Results of a 1993-1994 U.S. Food and Drug Administration study of 769 domestic and 1.062 imported fresh apples and 598 domestic and 612 imported processed rice samples resulted in phosalone detections of 1% (max 0.23 ppm) and 9% (max 3.2 ppm) in the domestic and imported apple samples, respectively(1). It was not detected in the rice samples(1). Results of a 1992-1993 U.S. Food and Drug Administration study of 710 domestic and 949 imported fresh pear and 1,219 domestic and 144 imported tomato samples resulted in phosalone detections of <1% (max 0.58 ppm) not detected in the domestic and imported pear samples(2). It was not detected in the tomato samples(2). A U.S. Market Basket Survey conducted from 1982-1991 that analyzed 234 processed food items containing 5,000 food types resulted in phosalone detections of 107 times found in 18 foods with an ave concn of 0.0252 ug/g(3). Individual results in this study were: apple products were detected 6 times at an ave concn of 0.0678 ug/g; baby food (Dutch apple or Apple Betty), detected 4 times at a concentration of 0.0438 ug/g; baby food, oatmeal, applesauce or banana, detected 2 times, ave concn 0.0035 ug/g; baby food, peaches, detected 10 times, ave concn 0.050 ug/g; baby food, pears or pears with pineapple, detected 10 times, ave concn 0.0326 ug/g; cereal, raisin bran, detected 3 times, ave concn 0.0283 ug/g; cherries, sweet, raw, detected 2 times, ave concn 0.0125 ug/g; grapes, purple or green, detected one, ave concn 0.0920 ug/g; peaches, raw, detected 2 times, ave concn 0.0410 ug/g; plums, purple, raw, detected once, ave concn 0.0080 ug/g; prunes, dried, detected 19 times, ave concn 0.0111 ug/g; raisins, dried, detected 4 times, ave concn 0.0420 ug/g(3). Phosalone residues on fruits and vegetables samples over a five-year period from 1991-1995 (1,536 vegetable and 802 fruits samples) were noted in 104 samples (a total of 4.4% of all samples) with one violation; concentration in ug/g, no of samples: <0.01, 5; <0.05, 12; <0.1, 14; <0.5, 38; <1, 17; <5, 17; <10, 1; >/=10, 0(4). 3 of 72 and 3 of 96 apple samples in 1995 and 1996, respectively, and 1 of 15 peach samples in 1996, tested positive for phosalone as part of the Danish National Pesticide Monitoring program of 4,182 samples collected from January 1995 through December 1996(5). Residues in 18 of 69 Spanish honey samples collected in 1988, 1989 and 1990 ranged from 3-37 ug/kg, mean of 10.3 ug/kg(6).|Phosalone was detected, not quantified in a survey of imported foods conducted in the US in 2003(1). The compound was not detected in canned and fresh peaches from Skydra, Greece collected in August 2000, detection limit of 20 ug/kg(2). Phosalone residues on fresh prunes, after washing for 5 minutes, after washing for 25 minutes, after drying, after drying and rehydration, and after a combination of 5 minutes washing, drying and rehydration were 0.21, 0.07, 0.08, 0.62, 0.49, and 0.24 mg/kg, respectively(3).
Occupational exposure should be low or non-existent since phosalone is no longer produced or used in the US (1992)(1). In a 1987 California survey of pesticide-related occupational exposures 55 workers were exposed to phosalone residues in the field and 1 was exposed using a mixer/loader for ground applications(2). In the past, phosalone was applied directly to crops as a spray and exposure to this compound was primarily by inhalation and in the field where it was applied. Monitoring data indicate that the general population may be exposed to phosalone strictly as a result of consumption of imported foods(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.)|Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)
In rats, phosalone was rapidly metabolized when admin orally. Three unidentified cmpd were present in urine. When carbonyl-c was labeled, 65.4% of label appeared as (14)co2 & 32.4% in urine & feces within 4 days.
Phosalone-oxon, which was formed in treated plants, degraded more rapidly than phosalone. In plants they were attacked hydrolytically @ p-s-c link.
OPs /including phosalone/ exert their neurotoxicity by binding to and phosphorylating the enzyme acetylcholinesterase in both the central (brain) and peripheral nervous systems. There are laboratory animal data on OPs for cholinesterase activity in plasma, red blood cell (RBC) and brain, as well as behavioral or functional neurological effects in submitted guideline studies. Measures of acetylcholinesterase inhibition in the peripheral nervous system (PNS) are very limited for the OP pesticides. As a matter of /EPA/ science policy, blood cholinesterase data (plasma and RBC) are considered appropriate surrogate measures of potential effects on PNS acetylcholinesterase activity and of potential effects on the central nervous system (CNS) when brain cholinesterase data are lacking.
The analysis of technical organophosphorus insecticides by (31)P nuclear magnetic resonance showed the major known toxic contaminants to be simple trialkyl phosphorothio- and -dithioic acid esters and the S-alkyl insecticide isomers. Small amt of the bis derivatives & the dithiopyrophosphate were also detected. These contaminants included both byproducts from the synthesis as well as degradation products. This procedure was used to analyze the following technical grade products: ronnel, sulfotepp, methyl parathion, dimethoate, malathion, methidathion, ethion, phosalone, & fenitrothion. /Organophosphorous insecticides/
Refer immediately for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Airway protection. Insure that a clear airway exists. Intubate the patients and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, so as to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /Organophosphate pesticides/|Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. ... Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. ... The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. /Organophosphate pesticides/|Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules of ... glycopyrolate were added to ... saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. ... /Organophosphate pesticides/|Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administer pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ... Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ... Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for PHOSALONE (21 total), please visit the HSDB record page.
/SIGNS AND SYMPTOMS/ Phosalone can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g., accidents or major spills), respiratory paralysis and death.|/SIGNS AND SYMPTOMS/ Symptomatology: 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis ... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain ... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. /Parathion/|/SIGNS AND SYMPTOMS/ Symptomatology: 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/|/SURVEILLANCE/ An illness characterized by weakness, dizziness, and gastrointestinal symtoms was identified among a crew of 30 migrant field-workers employed by a grape grower in Madera County, California, during August 1987. The onset of symptoms occurred between August 24 and August 30 and a median of 9 days from the date of first employment. The first crew member sought medical treatment on August 26, and 10 crew members were admitted to hospital between August 27 and August 30. For most workers, gastrointestinal and constitutional symptoms resolved shortly after admission, but 4 patients had episodes of severe sinus bradycardia persisting for several days. On the day of admission, transient atrioventricular dissociation developed in 2 persons. Interviews with 16 crew members not admitted to the hospital identified only 1 additional worker ill with gastrointestinal symptoms, but all 16 had moderate to severe inhibition of both plasma and red blood cell cholinesterase. Four other workers who were tested but not interviewed also had cholinesterase depression. The crew had had exposure since August 19 to the organophosphate insecticide phosalone, which was last applied to the vineyard on July 21, or 29 days earlier. Although this is the first report unequivocally linking phosalone to field-worker poisoning, the delayed onset and nonspecific nature of the symptoms associated with subacute poisoning may have hindered the recognition of previous similar episodes.
fosalon
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Dizziness. Nausea. Muscle twitching. Sweating. Pupillary constriction, muscle cramp, excessive salivation. Vomiting. Diarrhoea. Laboured breathing. Convulsions. Cough. Blurred vision. Unconsciousness.
Redness. Further see Inhalation.
Redness.
Phosalone Use and Manufacturing
Phosalone is produced by treating O,O-diethyldithiophosphoric acid with N-chloromethyl-5-chlorobenzoxazolone.|REACTION OF 6-CHLORO-3-(CHLOROMETHYL)BENZOXAZOLONE WITH METAL SALT OF PHOSPHORODITHIOIC ACID|Produced by the condensation of sodium O,O-diethyl phosphorodithioate with 6-chloro-3-chloromethyl-3H-benzoxazol-2-one, the latter being obtained by the interaction of urea with 2-aminophenol to give 3H-benzoxazol-2-one which is chlorinated to give the 6-chloro analog ... .
Insecticide, acaricide.
(1975) 2.72X10+8 G (CONSUMPTION)|(1978) 9.08X10+7 G (CONSUMPTION)
ESSENTIALLY 100% AS AN INSECTICIDE FOR FRUITS AND NUTS
...Include: Emulsifiable concentrate in UK `Zolone' (330 g/L) and in Australia (300 g/L). Various formulations known as `Zolone DT' for use in cotton contain phosalone plus DDT.|Flowable|'Zolone Liquid', 'Rubitox' (in Japan), emulsifiable concentrate (300-350 g ai/l); wettable powder (300 g/kg); dustable powder (25 or 40 g/kg). Mixtures include: (phosalone + parathion-methyl).|Phosalone is available in formulations of 30, 33, and 35% emulsifiable concentrate; 30% wettable powder; and 2.5 and 4% dusts.
The WHO Recommended Classification of Pesticides by Hazard identifies Phosalone (technical grade) as Class II: moderately hazardous; Main Use: insecticide.|Phosalone has no U.S. registrations and nine import tolerances, on almond (hulls), almonds, apples, apricots, cherries, grapes, peaches, pears, and plums (fresh prunes). Phosalone treated crops do not pose risk concerns, and no risk mitigation is necessary at this time.|/Outside the U.S./ Phosalone is used to control mites, apple rust mite, broad mite, brown almond mite, brown mite, spruce spider mite, citrus red mite, European red mite, Pacific spider mite, two-spotted spider mite, thrips, citrus thrips, Colorado potato beetle, plum curculio, pecan weevil, chrysanthemum leafminer, cherry fruit fly, walnut husk fly, apple maggot, whiteflies, aphids, citrus aphids, pecan aphids, buckthorn aphid, apple aphid, green apple aphid, leafcurl plum aphid, thistle aphid, black peach aphid, walnut aphid, rosy apple aphid, wooly apple aphid, potato aphid, rose, aphid, filbert aphid, black cherry aphid, green peach aphid, hop aphid, black pecan aphid, pecan spittlebug, leafhoppers, potato leafhopper, grape, leafhopper, variegated leafhopper, pecan phylloxera, grape phylloxera, pear psylla, European apple sawfly, peach twig borer, potato tuberworm, green fruitworm, orangedog, plume moths, pecan nut casebearer, mineola moth, European corn borer, fruittree leafroller, redbanded leafroller, obliquebanded leafroller, omnivorous leafroller, European leafroller, filbert leafroller, oriental fruit moth, hickory shuckworm, codling moth, filbert worm, grape berry moth, eyespotted bud moth.|Phosalone is applied as broadcast foliar applications using ground or aerial equipment. The maximum use rate per season on labels ranges from 1.6 lb ai/acre/season to 4.0 lb ai/acre/season, however, labels for non-EU countries (Turkey, Czech Republic, and Slovak Republic) do not specify the maximum number of applications allowed. Actual use practices typically result in significantly longer (<35 days) preharvest intervals, no more than 2- 3 applications per year at timings determined by pest pressure and official recommendations.|For more General Manufacturing Information (Complete) data for PHOSALONE (6 total), please visit the HSDB record page.
ANALYSIS OF ORGANOPHOSPHORUS PHOSALONE BY CAPILLARY GC WITH FLAME PHOTOMETRIC DETECTION.|COLORIMETRIC DETERMINATION OF PHOSALONE WITH PALLADIUM CHLORIDE AND P-NITROSO-N,N-DIETHYLANILINE.|Organic thiophosphate agricultural chemicals, such as phosalone, were analyzed by HPLC with on-line photolysis, followed by electrochemical detection using single or dual-electrode approaches for the species generated.|Retention ratio data compiled by the Food and Drug Administration in its Pesticide Analysis Manual (PAM) using packed gas chromatographic columns were examined for usage when capillary gas chromatography was applied for residue analysis. Retention ratios of a selected group of materials listed in the PAM tables were determined isothermally with split injection of 4 WCOT capillary columns coated with 4 different methane silicone coatings. Of the tested reference materials, 90 displayed retention ratios that matched the PAM values on all columns.|Analysis of products: By GLC with thermionic detection. Analysis of residues: By GLC.
Agrochemicals -> Acaricides, Insecticides|Acaricides, Insecticides|INSECTICIDES
Computed Properties
Molecular Weight:367.8
XLogP3:4.4
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:366.9868650
Monoisotopic Mass:366.9868650
Topological Polar Surface Area:105
Heavy Atom Count:21
Complexity:418
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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