Tetrachlorvinphos
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Tetrachlorvinphos
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CAS No:
961-11-5
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Formula:
C10H9Cl4O4P
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Chemical Name:
Tetrachlorvinphos
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Synonyms:
Tetrachlorovinphos;Phosphoric acid, 2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl ester;Phosphoric acid,2-chloro-1-(2,4,5-trichlorophenyl)ethenyl dimethyl ester;Phosphoric acid,2-chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl ester;Benzyl alcohol,2,4,5-trichloro-α-(chloromethylene)-,dimethyl phosphate;2-Chloro-1-(2,4,5-trichlorophenyl)vinyl dimethyl phosphate;Dimethyl-1-(2,4,5-trichlorophenyl)-2-chlorovinyl phosphate;Dimethyl 2,4,5-trichloro-α-(chloromethylene)benzyl phosphate;IPO 8
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CAS No:
Description
Tetrachlorvinphos appears as colorless crystals or white powder. Somewhat corrosive. (NTP, 1992)
Tetrachlorvinphos appears as colorless crystals or white powder. Somewhat corrosive. (NTP, 1992)|An organophosphate cholinesterase inhibitor that is used as an insecticide. It has low mammalian toxicity. (From Merck Index, 11th ed)
Tetrachlorvinphos Basic Attributes
365.96
365.96
213-506-3
2783
DTXSID1021320
Tan to brown crystalline solid|Powder|Off-white crystalline solid
2919900090
Characteristics
54.57000
5.60150
Mobile Crystals
1.52 g/cm3
97.5 °C
399.5ºC at 760 mmHg
302.8ºC
1.553
11mg/L(20 ºC)
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition sources and untrained individuals. Secure and label area. Protect containers/cylinders from physical damage.
4.2e-08 mm Hg at 68 °F (NTP, 1992)
... Mild chemical odor. /Gardona/
Henry's Law constant = 1.8X10-9 atm-cu m/mol at 25 °C (est)
Off-white, crystalline solid /Technical grade/|Hydroxyl radical reaction rate constant = 2.41X10-11 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
TETRACHLORVINPHOS is slowly hydrolyzed in neutral and aqueous acidic media. Is rapidly hydrolyzed in alkaline media.
Safety Information
I; II; III
6.1
STABLE TO LESS THAN 100 °C; SLOWLY HYDROLYZED IN WATER, 50% LOSS OCCURRING @ 50 °C IN 1300 HR @ PH 3, IN 1060 HR @ PH 7, IN 80 HR @ PH 10.5 /TECHNICAL PRODUCT/
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.|Tetrachlorvinphos stable < 100 °C can be slowly hydrolyzed in water with a 50% loss occurring @ 50 °C in 1300 hr at pH 3, in 1060 hr @ pH 7, in 80 hr @ pH 10.5. Recommendable method: Incineration. Peer review: Incineration @ high temp in a unit with effluent gas scrubbing is recommendable. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|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/
USEPA/OPPTS; Reregistration Eligibility Decision (RED) Tetrachlorvinphos. EPA 738-R-95-041 159 pp. (September 1995). This document provides a thorough review of the scientific data underlying this pesticide's registration and fulfills the EPA's requirement to determine whether pesticides containing this active ingredient are eligible for reregistration before calling in data on products.|USEPA Office of Pesticide Programs; Tolerance Reassessment Eligibility Decision and Reregistration Eligibility Decision Addenda for Tetrachlorvinphos Case No. 032 184 pp. (2006) describes additional actions taken by EPA on the basis of a review of common mechanisms for organophosphate pesticides.|DHEW/NCI; Bioassay of Tetrachlorvinphos for Possible Carcinogenicity (1978) Technical Rpt Series No. 33 DHEW Pub No. (NIH) 78-833
Flash point data are not available for this chemical; however, it is probably combustible. (NTP, 1992)
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, 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.|P201, P202, P261, P264, P270, P271, P273, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P322, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 74 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator away from bases and protect it from moisture. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Worker risks are of concern with the maximum level of protection for mixers, loaders, and applicators in poultry egg production operations applying wettable powder formulations with a low-pressure handwand and paint-on application of the EC formulation. ... The following mitigation measures are required: Restrict the use of low pressure handwands for wettable powder (WP) applications to spot treatment in poultry facilities and require double layer clothing, gloves, and dust/mist respirator for mixers, loaders, and applicators engaging in low pressure handwand activities using the WP formulations in egg and broiler facilities. ... Double layer clothing, gloves, and dust/mist respirator for mixers, loaders, and applicators using dusting equipment to apply WP formulation as dusts. Double layer clothing, gloves, and dust/mist respirator for mixers, loaders, and applicators engaging in paint-on activities using WP formulations.|In addition, worker risks exceeded the /EPA's/ level of concern with baseline PPE for handlers engaging in backpack, dusting, groundboom, and low pressure handwand activities. The following mitigation measures are required: ... Double layer clothing and gloves for workers when handling backrubber devices. Single layer and gloves for loaders and others handling dust bags.. Single layer clothing and gloves for mixers, loaders, and applicators engaging in groundboom activities using the EC and WP formulations. Single layer clothing and gloves for mixers, loaders, and applicators engaging in low pressure handwand activities using the EC formulations in poultry facilities. Single layer clothing and gloves for mixers, loaders, and applicators engaging in backpack spraying activities. Single layer clothing and gloves for workers when handling ear tags, mineral blocks, and pellets (oral larvicide feed-through products).
Products Intended Primarily for Occupational Use: Application Restrictions: Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application.|Products Primarily for Occupational Use: Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry.|Products Primarily for Occupational Use: Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.|Products Primarily for Occupational Use: Users should remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing.|For more Preventive Measures (Complete) data for TETRACHLORVINPHOS (13 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
RURAL/REMOTE: Tetrachlorvinphos was detected (concentration not reported) outside the spray area in air samples from Niigata, Japan following application of the compound to nearby rice paddy fields on Jun 6-Jul 1, 1988, application rate of 380 g/ha, 1,100 ha; Jun 27-30, 1989, application rate of 380 g/ha, 1,085 ha; and Aug 1-10, 1991, application rate of 375 g/ha, 670 ha(1).
According to analysis conducted by the US Food and Drug Admin from 1989-1994 of 457 mixed feed rations intended for cattle (172 samples), poultry (125 samples), swine (83 samples), pets (61 samples), fish (56 samples) and 48 miscellaneous samples, tetrachlorvinphos was detected in 2 unspecified samples at a concentration range of 0.030 to 0.740 ppm(1).
Toxicity
... Tetrachlorvinphos was ... monodealkylated by ... glutathione alkyl transferase. ... in mice ... pretreatment with diethyl maleate & methyl iodide, which reduce liver glutathione levels, potentiated toxicity of organophosphorus insecticides that are demethylated by glutathione transferase.|The effect of tetrachlorvinphos (TCVP) on liver procaine esterase (PROCase) and procaine toxicity was studied in rats. A single oral dose of 500 mg/kg of TCVP caused a remarkable decrease in PROCase (40% of control) 24 hr later and increased the mortality after injection of procaine (250 mg/kg, ip) from 54 to 87%. Conversely, PROCase was elevated to 140% of the control and mortality decreased from 54 to 25% on day 3. With repeated administration of TCVP (500 mg/kg/day) for 5 days, the PROCase activity that was inhibited on day 1 was gradually restored to normal levels by 5 days and the mortality altered to 25%. The inducible effect on PROCase was examined using desmethyl tetrachlorvinphos, a metabolite of TCVP without inhibitory effect on the enzyme; PROCase activity was enhanced to 1.6-fold of the control and procaine concentration in the brain was reduced to 30% of the control, accompanied with no death of rats after procaine injection. Electrophoresis of the solubilized liver microsomal fraction confirmed the inducible effect of TCVP on PROCase; microsomal protein from the TCVP-treated rate was more deeply stained than that from the control, and the PROCase activity of 2 anodic bands increased in the TCVP-treated microsomes. Thus, TCVP has a dual action on PROCase, inducible and inhibitory, and the direct inhibitory effect of TCVP might mask the increased amt of the enzyme induced by repeated administration of TCVP. The dual effect of TCVP on PROCase would cause the change in procaine toxicity.
LD50 Rat oral 1480 mg/kg (males); between 465 and 965 mg/kg (females)|LD50 Mouse (male) sc 16000 mg/kg body weight|LD50 Rat (male) sc 15000 mg/kg body weight|LD50 Mouse (male) ip 1170 mg/kg body weight|For more Non-Human Toxicity Values (Complete) data for TETRACHLORVINPHOS (13 total), please visit the HSDB record page.
/BIRDS and MAMMALS/ Pheasants showed convulsions, tremors and prostration during 2nd and 3rd day following treatment. /Oral; technical product/|/BIRDS and MAMMALS/ The /EPA/ relied on studies using three avian test species. From its review of these data, the Agency concludes that tetrachlorvinphos is practically non-toxic to birds. Mallard duck LD50 >2000 mg/kg; ring-necked pheasant LD50 >2000 mg/kg. and chukar LD50 >2000 mg/kg /From table/. On a subacute dietary basis, tetrachlorvinphos is practically nontoxic to birds. Two studies, one on the mallard duck and one on the bobwhite quail produced LC50s > 5000 ppm.|/AQUATIC SPECIES/ The results of the two 96-hour acute toxicity studies indicate that tetrachlorvinphos is highly toxic to both cold- and warmwater fish. (Test material 94% a.i; Bluegill sunfish 96 hr LC50 of 0.53 ppm and Channel catfish 96 hr LC50 of 0.53 ppm). Formulated product testing on fish has been required because the LC values of the technical pesticide is less than the 50 EEC in the aquatic environment. The results of the 96-hour acute toxicity study with rainbow trout as the test species and with a 75% formulated product (LC50 of 0.43 ppm) indicate that tetrachlorvinphos is highly toxic to freshwater fish|/AQUATIC SPECIES/ The chronic effect of an exposure to a sublethal concentration of commercial formulation of 4 organophosphorus insecticides such as ..., gardona (tetrachlorvinphos) ... on midvitellogenic ovaries of Mystus vittatus was investigated using several histological and histochemical techniques. The loss of stage II and III oocytes accompanied by a significant decline in gonadosomatic index was recorded. The vitellogenesis in treated fishes was ceased as the oocytes did not advance to further stages as evidence by the absence of lipid yolks and the lack of a PAS positive follicular layer. The RNA content of remaining stage I oocytes of exposed fishes resembled that of the stage I oocytes of the control fishes. The absence of delta 5-3 beta-hydroxysteroid dehydrogenase suggested the lack of steroidogenesis. Reduced glucose-6-phosphate dehydrogenase activity was also observed.|For more Ecotoxicity Excerpts (Complete) data for TETRACHLORVINPHOS (7 total), please visit the HSDB record page.
A bioassay of technical grade tetrachlorvinphos for possible carcinogenicity was conducted by administering the test chemical in feed to Osborne-Mendel rats and B6C3F1 mice. Groups of 50 rats of each sex were administered tetrachlorvinphos at one of two doses for 80 wk, then observed for 31 additional wk. Time weighted avg doses were either 4,250 or 8,500 ppm. Matched controls consisted of groups of 10 untreated rats of each sex; pooled controls, used for statistical evaluation, consisted of the matched controls combined with 45 untreated male and 45 untreated female rats from similar bioassays of four other test chemicals. All surviving rats were killed at 111 wk. Groups of 50 mice of each sex were administered tetrachlorvinphos at one of two doses, either 8,000 or 16,000 ppm for 80 wk, then observed for 12 additional wk. Matched controls consisted of groups of 10 untreated mice of each sex; pooled controls, used for statistical evaluation, consisted of the matched controls combined with 40 untreated male and 40 untreated female mice from similar bioassays of four other test chemicals. All surviving mice were killed at 90-92 wk. ... Under the conditions of this bioassay, the administration of technical grade tetrachlorvinphos in Osborne-Mendel rats was associated with proliferative lesions of the C cells of the thyroid and cortical adenomas of the adrenal /gland/ in females. In female B6C3F1 mice, the incidence of neoplastic nodule of the liver was associated with treatment, and in male mice tetrachlorvinphos was carcinogenic, causing hepatocellular carcinoma of the liver. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Positive; Male Mice: Positive; Female Mice: Positive.
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/
Tetrachlorvinphos is not known to occur in nature(1).
Tetrachlorvinphos's production may result in its release to the environment through various waste streams; its use as an insecticide and acaricide(1) will result in its direct release to the environment(SRC). In the US, crop uses were voluntarily canceled from product registrations in 1987(2). Its use in the control of ticks and fleas on pets and pet sleeping areas and in collars and shampoos for direct treatment of pets(3) will result in its release to the environment through various waste streams(SRC). Its use in cattle mineral licks(3) will reslut in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,000(SRC), determined from a log Kow of 3.53(2) and a regression-derived equation(3), indicates that tetrachlorvinphos is expected to have low mobility in soil(SRC). Volatilization of tetrachlorvinphos from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 4.2X10-8 mm Hg(4), and water solubility, 11 mg/L(5). Tetrachlorvinphos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). A biodegradation half-life of <8 days in soil(6) suggest that biodegradation may be an important fate process in soil(SRC).|TERRESTRIAL FATE: The half-life of tetrachlorvinphos in soil has been reported to range from approximately 15-22 days(1). When tetrachlorvinphos granules were applied at 1.5 kg/ha, residues persisted for 60 days(2). Within 7 days of application residues were detected to a depth of 22.5 cm(2). In another study, when tetrachlorvinphos was sprayed on peas, small amounts of the insecticide penetrated to 15 cm depth(3). The transformation rate of tetrachlorvinphos in four soils at 15 °C was determined from the residue remaining after 30 days of incubation in the laboratory in subdued daylight(4). The rates are approximately first order, corresponding to half-lives (soil, half-life): of medium loam (pH 8.0, water content 19% on dry weight), 9 days; clay loam (pH 8.0, water content 20% on dry weight), 6 days; sandy loam (pH 7.9, water content 16% on dry weight), 6 days; peat (pH 6.4, water content 100% on dry weight), 11 days, respectively(4,5). The degradation rate was greater than would be expected on the basis of in vitro hydrolysis studies, and the reaction in soil is probably mostly microbial(6). Taking into account the adsorption and transformation rates, there should be negligible leaching of tetrachlorvinphos from the root zone(5).|TERRESTRIAL FATE: Granules of tetrachlorvinphos were applied to soil (sandy loam illite clay, pH 8.2, organic carbon 0.32%) in bands at 1.5 kg/ha in a field study. The compound was applied in September and rainfall was 7, 12, 0, 4, 32, and 0 mm in Sept, Oct, Nov, Dec, Jan, and Feb, respectively. Residues of tetrachlorvinphos reached beyond the 15 cm depth. Tetrachlovinphos concentrations in the 1-15 cm layer were 5.0, 3.5, 2.5, 1.25, 0.3, and not detected after 0, 7, 15, 30, 45, and 60 days respectively(1). Concentrations in the 15-30 cm layer were 0.55, 0.50, 0.30, and not detected after 7, 15, 30, and 45 days respectively(1). A field half-life of 14 days was calculated(1).|TERRESTRIAL FATE: After application to soil, the initial degradation product is 2,4,5-trichlorophenacyl chloride; after 30 days, the major metabolites are 1-(2',4',5'-trichlorophenyl)ethan-1-ol, 1-(2',4',5'-trichlorophenyl)-2-chloroethan-1-ol, and 2,4,5-trichloroacetophenone(1). The main metabolites in soil are also plant metabolites and therefore plants would not be exposed to residues in the soil that were not also present in the crops as a result of foliar application(2). In laboratory studies there was no evidence of isomerization(2). However, since the pesticide was mixed into the soil, there was no opportunity for photochemical reactions as would be possible under field conditions when tetrachlorvinphos is applied to the soil surface(2).|For more Environmental Fate (Complete) data for TETRACHLORVINPHOS (6 total), please visit the HSDB record page.
The rate constant for the vapor-phase reaction of tetrachlorvinphos with photochemically-produced hydroxyl radicals has been estimated as 2.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 16 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of tetrachlorvinphos with ozone has been estimated as 3.0X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2).|Tetrachlorvinphos undergoes slow hydrolysis in acid and rapid hydrolysis in base. In acid and neutral solution, dealkylation occurs and in alkaline solution, the P-O bond is ruptured(1). The half-life at pH 7 and 50 °C was 12 days(1). At pH 3, the half-lives were 90 days at 5 °C and 45 days at 60 °C(1). At pH 10, 50% decomposition occurred within 24 hr(1). Another source reports the disappearance half-lives at 50 °C as 54 days (pH 3), 44 days (pH 7), and 80 hr (pH 10.5)(3). A third source reports the hydrolysis half-lives as 50 days at pH 3 and 3.3 days at pH 5, presumably at room temperature(4). At 38 °C, the hydrolysis half-life is 37 hours at pH 9.1(5). On exposure to UV radiation, tetrachlorvinphos underwent cis isomerization leading to a cis-trans equilibrium that was not altered by further irradiation(2). In nonpolar solvents and on dry soil and glass or leaf surfaces, photoisomerism is the principal reaction(4). After prolonged exposure to sunlight on a leaf, where photolysis is faster than on dry soil or a glass plate and slower than in solution, polar metabolites appear(4). The half-life of tetrachlorvinphos on a leaf is approximately 6 days(4). In addition to the cis isomer, products included 2,4,5-trichlorophenacyl chloride, 1-(2,4,5-trichlorophenyl)ethan-1-ol, 2,4,5-trichloroacetophenone, and 1-(2,4,5-trichlorophenacyl)ethan-1-ol(2).
40.74|An estimated BCF of 17 was calculated in fish for tetrachlorvinphos(SRC), using a log Kow of 3.53(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
1.02e+03 L/kg|The Koc of tetrachlorvinphos is estimated as 2,000(SRC), using a log Kow of 3.53(1) and a regression-derived equation(2). A calculated Koc of 1,170 based on a water solubility of 11 ppm has also been reported(3). According to a classification scheme(3), these estimated Koc values suggest that tetrachlorvinphos is expected to have low mobility in soil.|The distribution coefficients of tetrachlorvinphos in three glasshouse soils from The Netherlands and water were (cu dm/kg): sand (pH 6.9, 3.1% organic matter), 20.0; sandy loam (pH 7.0, 3.6% organic matter), 19.6; loam (pH 7.1, 9.7% organic matter), 115(1).
The Henry's Law constant for tetrachlorvinphos is estimated as 1.8X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 4.2X10-8 mm Hg(1), and water solubility, 11 mg/L(3). This Henry's Law constant indicates that tetrachlorvinphos is expected to be essentially nonvolatile from water surfaces and moist soil(4). Tetrachlorvinphos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
GROUNDWATER: According to EPA's Pesticides in Groundwater Database, tetrachlorvinphos was not found in groundwater tested in California (n=12) in 1984-1989 and Indiana (n=161) in 1987-1988(1).|DRINKING WATER: In EPA's 5-yr National Pesticide Survey of drinking water wells, tetrachlorvinphos was not detected in the 783 rural domestic wells and 566 community water system wells tested nationwide(1).|SURFACE WATER: Tetrachlorvinphos was not found in monthly samples of surface water in The Netherlands at 6 sites in a bulb-growing area between August 1989 and Jan 1990(1). Samples from tile drains and water courses in 7 locations in The Netherlands with many glasshouses (n=22) resulted in two samples with detectable (>0.1 ug/L) levels of tetrachlorvinphos, 0.3 ug/L and 0.2 ug/L(2).|RAIN/SNOW/FOG: Rainwater from the area around Naaldwijk, The Netherlands, a region of intensive greenhouse horticultural activities and a less farm intensive region near Lake Nieuwkoopse Plassen, The Netherlands, was analyzed for the presence of tetrachlorvinphos(1). Samples were collected in the field after 14-day sampling periods at May 28, June 11, June 25, and July 9, 1997. Rainfall totals were 33.4, 22.2, 28.4, and 74.1 mm at Naaldwijk and 51.7, 9.5, 32.2, and 51.3 mm at Lake Nieuwkoopse Plassen. Tetrachlorvinphos was not detected in any of the samples tested, detection limit 0.03 ng/L(1). In samples from a rural area in Niigata City, Niigata Prefecture, in Japan. Paddy fields are located 200 to 400 m away. Monthly tetrachlorvinphos concentrations starting in Apr, 1992 and going through Oct, 1992 were (precipitation in mm): not detected (127); 0.78 (111); 18.4 (98); 25.7 (115); 120 (91); 16.4 (45); 1.9 (148), all in ug/sq m/month; it was not detected in precipitation collected from November 1992 through March, 1993(2).
In a 1992-1993 FDA statistically-based study, tetrachlorvinphos was not found in domestic (n=710) and imported (n=949) pears or domestic (n=1,219) and imported (n=144) tomatoes at a 0.03 ppm level of quantitation(1). In a 10-year FDA study of ready-to-eat foods (230 food items, 17,050 samples), tetrachlorvinphos was only found in 1 sample of raw peaches at 0.0050 ppm(2). No tetrachlorvinphos (detection limit 2.0 ppm) was found on 6,970 samples of produce surveyed between 1989 and 1991(3). Of 19,851 samples of domestic and imported food and feed surveyed by the FDA Los Angeles District Laboratory between 1981 and 1986, only two contained tetrachlorvinphos, one in the range 0.05-0.1 ppm and the other in the range 0.1-0.5 ppm(4).|Tetrachlorvinphos residues were found in FDA's Total Adult Diet Study (3744 samples) in FY83-86(1). The number of positive samples was not reported, indicating an incidence level of <2%(1). During FDA's regulatory monitoring of domestic and imported adult food eaten by infants and children between FY85 and FY91 (>10,000 surveillance samples), tetrachlorvinphos was only found in 2 of 2,464 samples of domestic apples with a maximum residue 0.26 ppm; a trace was found in 1 of 351 samples of imported apple juice(2). Tetrachlorvinphos was not detected in any of the 27 market baskets of infant and adult foods eaten by infants and children during this time period(2).
EXPERIMENTAL: No residues of tetrachlorvinphos or 2,4,5-tetrachloroacetophenone, a metabolite, were detected in milk of a cow given dietary concns of 5 mg/kg of tetrachlorvinphos(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 644 workers (123 of these were female) were potentially exposed to tetrachlorvinphos in the US(1). The NOES Survey does not include farm workers. Occupational exposure to tetrachlorvinphos may occur through inhalation of dust and dermal contact with this compound at workplaces where tetrachlorvinphos is produced or used. Monitoring and use data indicate that the limited general population may be exposed to tetrachlorvinphos via inhalation of ambient air following field application and dermal contact with consumer products containing tetrachlorvinphos(SRC).
Drug Information
/VET/ An insecticide, tetrachlorvinphos is currently applied dermally to livestock to control flies and mites; used as a feed-through (oral) larvicide in cattle, hogs, goats, and horses; in cattle ear tags to control flies; in poultry dust boxes to control poultry mites; and as paint on and sprays in poultry houses. Tetrachlorvinphos also is used as a dust/powder, aerosol, and pump spray on pets and in pet sleeping areas, and in collars and shampoos for direct treatment of pets.
Fifty-five pet dogs (23 in study 1; 22 in study 2) of different breeds and weights were treated with over-the-counter flea collars containing tetrachlorvinphos (TCVP). During study 1, fur of treated dogs was monitored for transferable TCVP residues using cotton gloves to pet the dogs during 5-min rubbings post-collar application. ... Average amounts of TCVP transferred from the fur of the neck (rubbing over the collar) and from the back to gloves at 3 days post-collar application were 23,700+/-2100 and 260+/-50 ug/glove, respectively. ... During study 2, transferable TCVP residues to cotton gloves were monitored during 5-min rubbings post-collar application. Transferable residues were also monitored on cotton tee shirts worn by children and in the first morning urine samples obtained from adults and children. Average amounts of TCVP transferred to gloves at 5 days post-collar application from the neck (over the collar) and from the back were 22,400+/-2900 and 80+/-20 ug/glove, respectively. Tee shirts worn by children on days 7-11 contained 1.8+/-0.8 ug TCVP/g shirt. No significant differences were observed between adults and children in urinary 2,4,5-trichloromandelic acid (TCMA) levels; however, all TCMA residues (adults and children) were significantly greater than pretreatment concentrations (alpha=0.05)...|EPA has data from multiple sources that show tetrachlorvinphos feed-through products decrease cholinesterase levels /in horses/. EPA is therefore requesting the registrants add label statements to horse oral larvicides which state that the product is a chlolinesterase inhibitor, describe signs of cholinesterase inhibition in horses, caution against the use with other cholinesterase inhibiting compounds, and direct horse owners to consult a veterinarian before using products containing tetrachlorvinphos on debilitated, aged, pregnant or nursing animals.|The most frequently reported clinical signs of cholinesterase inhibition in the horse are abdominal pain, lethargy, sweating, tearing and excessive salivation. If these signs are seen in horses, consult your veterinarian immediately.|Several comments were submitted /to EPA/ ... associating reproduction problems in pregnant mares with use of tetrachlorvinphos feed-through products.
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.)|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.)
A study was conducted with male CD rats using doses of 0.01, 0.1, 1, or 5 mg/sq cm radiolabeled tetrachlorvinphos, with some of each dose group sacrificed at 0.5, 1, 2, 4, or 10 hours. Additionally, there was a group of animals, sacrificed at 72 hours, in which the skin was washed at 10 hours. The area of the dermal application was washed to recover unabsorbed tetrachlorvinphos. Then, the skin, urine, feces, and carcass were analyzed for percent of total tetrachlorvinphos applied. For the group sacrificed at 10 hours, 84% of the total applied (0.1 mg/sq cm ) tetrachlorvinphos was recovered in the wash, and 9.57% remained in the skin, urine, feces, and carcass. This absorption value, 9.57%, is used for assessing human risk following dermal exposure. The percent absorption increased with the duration of exposure and generally decreased with increasing dose. The actual quantity of tetrachlorvinphos absorbed increased with increasing dose.|Laying hens were treated with a wettable powder formulation of stirofos (Rabon, 2-chloro-1-(2,4,5-trichlorophenyl) vinyl dimethylphosphate) by dipping in a 0.5 or 1.0% actual ingredient (AI) water suspension of a 50% wettable powder (WP) stirfos formulation. Stirofos residues were detected in eggs within 1 day after treatment and reached maximum levels 3 days after dipping (0.021 and .035 ppm in the low- and high-dose birds, respectively). After that time, levels of residues in eggs declined rapidly and no sample contained detectable quantities (less than .004 ppm) of stirofos after 21 days...|Single oral dose to rats of (14)C-labelled tetrachlorvinphos ... almost completely eliminated in the urine in 4 days (44-78% during the first 24 hr and 4-15% during the second 24 hr). 78% of the radioactive material was excreted in urine, 16.5% in the feces and 0.5% in the expired air, probably as (14)CO2.
Radiolabelled tetrachlorvinphos was given orally to CD rats as a single low dose (5 mg/kg), as a single high dose (250 mg/kg), and in a series of doses (5 mg/kg). It was almost completely metabolized and most of the label was excreted in urine (46-60%) and feces (38-56%) within 48 hours of dosing. Only minor amounts were found in the tissues. Very little unmetabolized parent compound was recovered. The metabolic processes produced a number of different metabolites which were not all identified. The major metabolite observed in feces was trichlorophenylethanol with females eliminating more of this metabolite (18-34% total administered C) than males (13-23%) at all three dosing levels. Trichlorophenylethandiol was also found in feces ranging from 4-7 % in males and 3-6 % in females. A major metabolite in urine, trichloromandelic acid, was excreted in males at 19-26% but only 10-12% in females. At the high dose, females excreted more (25%) desmethyl tetrachlorvinphos than males (11%). However, there was essentially no difference for the low dose group with males (8%) and females (7%.)|The qualitative nature of the residue in ruminants following oral dosing is adequately understood. In a goat metabolism study the major metabolites identified were free 1-(2,4,5- trichlorophenyl)ethanol, conjugated 1-(2,4,5- trichlorophenyl)ethanol, and 2,4,5-trichloroacetophenone. The proposed metabolic pathway in ruminants following oral administration involves conversion of tetrachlorvinphos to trichlorophenylethanol, which is conjugated to glucuronide or further metabolized to trichloroacetophenone.|Also, the qualitative nature of the residue in ruminants following dermal application is adequately understood. The major residues identified were the parent tetrachlorvinphos, free 1-(2,4,5- trichlorophenyl)-ethanol, conjugated 1-(2,4,5- trichlorophenyl)ethanol, and 2,4,5-trichloroacetophenone.|Tetrachlorvinphos was poorly absorbed through the skin, and most residues adjacent to the application site were not metabolized. Residues that entered the general circulation were extensively metabolized in tissues distal to the application site. In the proposed metabolic pathway in ruminants following dermal application, tetrachlorvinphos was metabolized to either 1-(2,4,5- trichlorophenyl)ethanol, which is conjugated to glucuronic acid, or to 2,4,5-trichloroacetophenone, which is converted to 2,4,5- trichlorobenzoic acid.|For more Metabolism/Metabolites (Complete) data for TETRACHLORVINPHOS (11 total), please visit the HSDB record page.
0.10 Days
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/|Cholinesterase activity of plasma is significantly higher in men than in women, and this is true no matter which of several choline esters are used as substrate in measuring the enzyme activity. According to some, the difference is confined to young people. There is no sex difference in the red cell enzyme activity. Serum cholinesterase activity of blacks tends to be lower than whites of the same sex. /Organic phosphorus pesticides/
SYMPTOMS: Symptoms of exposure to this material include increased perspiration, nausea, lachrymation, salivation, blurred vision, diarrhea, pulmonary edema, respiratory embarrassment and convulsions. ACUTE/CHRONIC HAZARDS: This material may be absorbed through the skin and is a lachrymator. It is a cholinesterase inhibitor. This compound is a positive animal carcinogen. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, administer a slurry of activated charcoal in water and simultaneously call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organophosphates and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Organophosphates and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously and consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer atropine. Correct hypoxia before giving atropine ... . Administer pralidoxime chloride (2 PAM). USE UNDER DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. In rare cases diazepam or lorazepam may be necessary ... . Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organophosphates and related compounds/|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/|For more Antidote and Emergency Treatment (Complete) data for TETRACHLORVINPHOS (18 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ Patch tests in human subjects reveal that tetrachlorvinphos has no adverse effect on the skin of normal subjects as well as those with hypersensitivity. None of 50 subjects wearing fabric gloves treated with 0.1% for approximately 3 months (winter) showed poisoning symptoms.|/HUMAN EXPOSURE STUDIES/ Repeated daily doses of up to 15 mg tetrachlorvinphos fed to human volunteers were reported in an abstract to have no effect on plasma or red-cell cholinesterase activities.|/SIGNS AND SYMPTOMS/ Tetrachlorvinphos 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/ 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, and loss of orientation. Psychic disorders, nystagmus, trembling of the hands and other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis and paralysis develop. /Organophosphorus pesticides/|For more Human Toxicity Excerpts (Complete) data for TETRACHLORVINPHOS (15 total), please visit the HSDB record page.
Gardona
Tetrachlorvinphos Use and Manufacturing
REACTION OF 2,2,2',4',5'-PENTACHLOROACETOPHENONE WITH TRIMETHYL PHOSPHITE|Prepn of active Z-isomer: Philips, Ward, Ramsey, US Patents 3,102,842 & 3,553,279 (1963,1971 both to Shell)
For tetrachlorvinphos (USEPA/OPP Pesticide Code: 083702) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|Organophosphate insecticide. It is currently used as a dermal and feed-through (oral) larvicide in cattle, hogs, goats, and horses; in cattle ear tags to control flies in cattle feedlots; in poultry dust boxes to control poultry mites. It is used to control nuisance and public health pests (flies) in and around refuse sites, recreational areas, and for general outdoor treatment.|... control of ticks and fleas on pets and pet sleeping areas and in collars and shampoos for direct treatment of pets|The additive 2-chloro-1-(2,4,5-trichlorophenyl) vinyl dimethylphosphate may be safely used in accordance with the following prescribed conditions: (a) ... used as a feed additive in feed of beef, dairy cattle, and horses at 0.00015 lb (0.07 g) and swine at 0.00011 lb (0.05 g)/100 lb/ of bw/day; (b) ... used for control of fecal flies on manure of treated cattle, horses, and swine. (c) to assure safe use of the additive, the label and labeling of pesticide formulation containing the feed additive shall conform to the label and labeling registered by the US EPA.|For more Uses (Complete) data for TETRACHLORVINPHOS (11 total), please visit the HSDB record page.
(1975) 4.54X10+7 G (CONSUMPTION)|(1978) 4.54X10+7 G (CONSUMPTION)|Total US usage in 1978 estimated to be 45,000 kg.
Essentially all US usage in 1978 went for controlling insects on livestock and poultry.|Approximately 900,000 lbs active ingredient of tetrachlorvinphos are used annually
Formulation Types Registered: Technical: 98.7% a.i., Manufacturing use: 97.3% a.i., Wettable powder: 50% a.i., Dust: 1%, 3% a.i,. Granular: 0.18% to 7.76% a.i,. one product 97.3% a.i., Pelleted/Tableted 0.3% to 1.25% a.i. primarily mineral blocks for cattle/livestock. Impregnated material: 3%, 13.7% a.i. pet collars, cattle ear tags. Liquid, ready-to-use: 1% to 2% a.i. spray on/wipe on/backrub materials for pets, horses, cattle. Pressurized liquid: 1% a.i. flea and tick spray for cats. Emulsifiable concentrate: 23%, 24% a.i.|TECHNICAL GARDONA CONTAINS 98% CIS-ISOMER. ... TECHNICAL RABON NOT LESS THAN 94% BY WT AI ... WETTABLE POWDER--50% & 75% ACTIVE. EMULSIFIABLE CONCENTRATES--24% ACTIVE INGREDIENT. GRANULES--5% ACTIVE INGREDIENT. EXPTL FORMULATIONS: DUST CONCENTRATE--50% ACTIVE, SPECIAL ULV SUSPENSIONS.|Revap|Technical grade is typically 98% pure.|For more Formulations/Preparations (Complete) data for TETRACHLORVINPHOS (78 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies Tetrachlorvinphos (technical grade) as unlikely to present an acute hazard in normal use; Main Use: insecticide.|BECAUSE OF RAPID BREAKDOWN, IS NOT EFFECTIVE AGAINST SOIL INSECTS.|... crop uses were voluntarily canceled from product registrations in 1987.
... BY IR SPECTROSCOPY OR GLC (DETAILS FROM SHELL INTERNATIONAL CHEMICAL CO). RESIDUES ... & ITS MAJOR METABOLITES IN PLANTS MAY BE DETERMINED BY GLC.|Method: ASTM D5475; Procedure: gas chromatography with a nitrogen-phosphorus detector; Analyte: tetrachlorvinphos; Matrix: ground water and finished drinking water; Detection Limit: 0.76 ug/L.|Method: EPA-NERL 525.2; Procedure: gas chromatography/mass spectrometry; Analyte: tetrachlorvinphos; Matrix: finished drinking water, source water, or drinking water in any treatment stage; Detection Limit: 0.13 ug/L.|Method: EPA-OSW 8141B (GC-FPD); Procedure: gas chromatography with flame photometric detector; Analyte: tetrachlorvinphos; Matrix: water, soil, and waste samples ; Detection Limit: not provided.|For more Analytic Laboratory Methods (Complete) data for TETRACHLORVINPHOS (7 total), please visit the HSDB record page.
HUMAN ADIPOSE TISSUE; GC/ELECTRON CAPTURE DETECTION; ANALYSIS OF PESTICIDE RESIDUES IN HUMAN SAMPLES.|MATRIX: MILK; PROCEDURE: GC/PHOSPHORUS-SENSITIVE THERMIONIC EMISSION DETECTOR; LIMIT OF DETECTION: 0.03 MG/KG. MATRIX: ANIMAL ADIPOSE TISSUE; PROCEDURE: GC/ELECTRON CAPTURE DETECTION: WATTS, RR (ED); ANALYSIS OF PESTICIDE RESIDUES IN ENVIRONMENTAL SAMPLES.
Agrochemicals -> Insecticides|INSECTICIDES
Computed Properties
Molecular Weight:366.0
XLogP3:3.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:365.896306
Monoisotopic Mass:363.899257
Topological Polar Surface Area:44.8
Heavy Atom Count:19
Complexity:371
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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