기본 정보
- 표준 SMILES
CCOC(=O)C(SP(=S)(OC)OC)c1ccccc1- InChIKey
XAMUDJHXFNRLCY-UHFFFAOYSA-N- 분자식
- C12H17O4PS2
- 평균 분자량
- 320.4 g/mol
- 단동위원소 질량
- 320.03058765
개요
Phenthoate is an organic thiophosphate that is ethyl mandelate in which the hydroxy group has been replaced by a (dimethoxyphosphorothioyl)sulfanediyl group.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 acaricide, an agrochemical and an EC 3.1.1.7 (acetylcholinesterase) inhibitor. It is an ethyl ester, an organothiophosphate insecticide and an organic thiophosphate.
이름 및 식별자
- 우선 이름
- Phenthoate
- IUPAC
- ethyl 2-dimethoxyphosphinothioylsulfanyl-2-phenylacetate
- 현지명
- 에틸2-디메톡시포스피노티오일술파닐-2-페닐-아세테이트
- 영어명
- ethyl 2-dimethoxyphosphinothioylsulfanyl-2-phenyl-acetate
- 분자식
- C12H17O4PS2
- 분자량
- 320.36
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
2597-03-7、61361-99-7、61362-00-3、61391-87-5- PubChem CID
- 17435
- DTXSID
DTXSID6042280- ChEMBL
CHEMBL1476858- ChEBI
CHEBI:34917- UNII
- J96Q7F091K
- EC Number
- 219-997-0
- Nikkaji
- J3.033C
물성
구조 계산 물성
- XLogP
- 3.7
- 극성 표면적
- 102 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 8
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 324
실험 및 물리화학적 성질
Pesticides
Pesticides
Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Organophosphate Insecticides
Pesticide
Pesticide (Phenthoate) -> USDA PDB
LogP
Kow = 4900
3.32
Solubility
REDDISH-YELLOW OIL; SOLUBILITY: IN WATER @ 20 °C= 200 MG/L (TECHNICAL GRADE); IN HEXANE @ 20 °C= 120 G/L; GREATER THAN 200 G/L IN 1,2-DIMETHOXYETHANE, 20 °C (PURE); IN PETROLEUM SPIRIT @ 20 °C= 100-170 G/L /TECHNICAL/
11 MG/L WATER @ 24 °C
Miscible in all proportions with methanol, ethanol, benzene, xylene, acetone, cyclohexanone, methylcellosolve, carbon tetrachloride and carbon disulfide, ethyl ether, dioxane, and cyclohexane
Soluble in aromatic hydrocarbons, ketones, alcohols, chloroform, and carbon tetrachloride. Barely soluble in ... petroleum ether.
Vapor Pressure
0.0000026 [mmHg]
2.6X10-6 mm Hg at 25 °C
안전 및 규제
GHS 분류
GHS Classification
Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)
Danger
H302+H312 (90.5%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P260, P264, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P316, P317, P320, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
유해성 정보
Hazards Summary
No evidence of mutagenicity; [HSDB] In 116 week feeding study with rats cholinesterase activity was depressed, but no significant histopathological findings or increased tumor frequency; [Reference #1] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
FIFRA Requirements
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ethyl alpha-((dimethoxyphosphinothioyl)thio)benzeneacetate is found on List B. Case No: 2800; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Ethyl alpha-((dimethoxyphosphinothioyl)thio)benzeneacetate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
DOT Emergency Guidelines
/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.
DOT Hazard Classification
Phenthoate
Severe marine pollutant
Other Hazardous Reactions
A portion of even the most flammable materials is likely to be lost by vaporization. ... The smoke from an open fire used to destroy pesticides will contain some of the poison. Burning should be attempted only in an isolated place. Inhalation of smoke must be avoided. /Pesticides/
Hazard Classes and Categories
Acute Tox. 4 (97.6%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 3
Acute Tox. 4 *
Standard Transportation Number
49 216 74; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 75; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 105 44; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 105 45; Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)
49 216 76; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)
49 216 77; Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, other than liquid)
Shipment Methods and Regulations
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.
Shipping Name/ Number DOT/UN/NA/IMO
UN 3018; Organophosphorus pesticides, liquid, toxic, not otherwise specified
UN 3017; Organophosphorus pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint between 23 °C and 61 °C
UN 2783; Organophosphorus pesticides, solid, toxic, not otherwise specified
UN 2784; Organophosphorus pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °C
For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for PHENTHOATE (6 total), please visit the HSDB record page.
안전 및 보호
Exposure Control and Personal Protection
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
Fire Fighting Procedures
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/
Storage Conditions
... MUST BE STORED IN ITS SEALED ORIGINAL CONTAINERS, IN WELL-AIRED, FRESH & DRY STOREHOUSES OR IN SHADED & POSSIBLY WELL-AIRED PLACES. IT IS RECOMMENDED THAT THE PRODUCT'S TEMP ... NOT EXCEED 25-30 °C, & KEEP ... AWAY FROM SOURCES OF HEAT FREE FLAMES OR SPARK-GENERATING EQUIPMENT. CONTAINERS MUST BE STACKED IN SUCH A WAY AS TO PERMIT FREE CIRCULATION OF AIR ... AT BOTTOM & INSIDE OF PILES. STORAGE AREAS MUST BE LOCATED AT A SUITABLE DISTANCE FROM INHABITED BUILDINGS, ANIMAL SHELTERS, & FOOD STORES; MOREOVER, THEY MUST BE INACCESSIBLE TO UNAUTHORIZED PERSONS, CHILDREN, & DOMESTIC ANIMALS.
Rooms used for storage only should be soundly constructed & fitted with secure locks. Floors should be kept clear & pesticides clearly identified. If repacking is carried out in storage rooms, adequate light should be available; floors should be impervious & sound ... . /Pesticides/
Pesticides containers must be provided with labels indicating the degree of toxicity of the product they contain. The labels must not only give a short description of how to use the prepn, but also state basic precautions to be taken when applying it. /Organophosphorus pesticides/
Pesticides of any degree of toxicity should be transported in containers which are clearly labelled, leak-proof, and not easily damaged. They should never be transported /or stored/ beside, or above any type of food, and all spillages should be immediately reported. /Pesticides/
Disposal Methods
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))
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.
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/
Preventive Measures
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.
Personal Protective Equipment (PPE)
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/
독성 정보
Interactions
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.
Ecotoxicity Values
LD50 Pheasant oral 218 mg/kg
LC50 Japanese quail oral 3536 ppm in 5-day diet (95% confidence limit 50.3-74.3 ppm), age 14 days /Technical material, 95%/
LC50 Ring-necked pheasant oral 2775 ppm in 5-day diet (95% confidence limit 45.1- 62.4 ppm), age 10 days /Technical material, 95%/
LC50 Mallard duck oral approx 4500 ppm in 5-day diet, age 10 days /Technical material, 95%/
For more Ecotoxicity Values (Complete) data for PHENTHOATE (10 total), please visit the HSDB record page.
Food Survey Values
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).
Medical Surveillance
Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/
A final diagnosis of mild to moderate acute organophosphate pesticide poisoning is rarely justified unless all of the following five conditions are present: 1. A definite history of exposure to an organophosphate pesticide. 2. A latent interval of not more than a few hours between that last exposure and the onset of illness. 3. A clinical picture in which most or all of the following signs or symptoms are present: headache, blurred vision, weakness, tightness in chest, and constricted pupils. 4. Reduction of plasma and RBC cholinesterase activity to a level substantially below 50% of baseline values. Because of the wide normal range of RBC cholinesterase in the population, symptoms may be present with reported "normal" levels. 5. An acute illness that is not substantially longer than 48 hours. The classic presentation for acute organophosphate toxicity includes history, evidence of exposure to organophosphate (garlic odor), signs/symptoms of cholinergic excess, improvement with atropine or pralidoxime, and inhibition of cholinesterase in blood. /Organophosphate pesticide poisoning/
... Surveillance of workers could be carried out through measurement of blood or urinary levels of the cmpd to which they are exposed, or through measurement of a metabolite. /Organic phosphorus pesticides/
Soil Adsorption/Mobility
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).
Human Toxicity Excerpts
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.
Environmental Biodegradation
A four-week biodegradation study using 30 mg/l sludge and a phenthoate concentration of 100 mg/l gave a theoretical BOD of 0-3%(1). In various soils (silty clay loam, clay, and sandy loam), 50% of the phenthoate present degraded within 10 days, and over 95% within 30 days(2). In a drier soil (fine sandy loam), 62% of the phenthoate remained after 75 days, but less than 1% remained after an additional 75 days(2). This degradation was attributed to loss by soil microorganisms(2).
Environmental Bioconcentration
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).
규제 정보
FIFRA Requirements
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Ethyl alpha-((dimethoxyphosphinothioyl)thio)benzeneacetate is found on List B. Case No: 2800; Pesticide type: insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Ethyl alpha-((dimethoxyphosphinothioyl)thio)benzeneacetate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
화학 및 산업
약리 정보
Mechanism of Action
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.
Metabolism/Metabolites
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.
Absorption, Distribution and Excretion
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.
용도 및 제조
Uses
Used as insecticide and acaricide for rice, vegetables, fruits, and tea; [HSDB]
Cancelled--no longer registered as a pesticide for use in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
The active ingredient is no longer contained in any registered pesticide products ... "cancelled."
INSECTICIDE; ACARICIDE
Useful for protection of rice, vegetables, fruits, and tea against chewing and sucking insects.
Methods of Manufacturing
/Manufactured/ by the interaction of ethyl-alpha-bromo, alpha-phenyl acetate with O,O-dimethyl phosphorodithiochloridate
Reaction of ethyl phenylacetate with O,O-dimethyl dithiophosphoric acid (alpha bromination/dehydrobromination)
Formulations/Preparations
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.
General Manufacturing Information
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.
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