Dialifos (ISO)

Dialifor

HCID 25146CAS 10311-84-9

Grundinformationen

Standard-SMILES
CCOP(=S)(OCC)SC(CCl)N1C(=O)c2ccccc2C1=O
InChIKey
MUMQYXACQUZOFP-UHFFFAOYSA-N
Summenformel
C14H17ClNO4PS2
Durchschnittliche Molmasse
393,8 g/mol
Monoisotopische Masse
393,00251433

Überblick

Dialifor is a white crystalline solid, also reported as a colorless oil, colorless. Used as an insecticide and acaricide (kills beetles, ticks, mites, etc.). (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Dialifor
IUPAC
2-(2-chloro-1-diethoxyphosphinothioylsulfanylethyl)isoindole-1,3-dione
Lokaler Name
Dialifos (ISO)
Englischer Name
DIALIFOS
Summenformel
C14H17ClNO4PS2
Molmasse
393.85

Namen und Synonyme

DialifosDIALIFORTorakDialiphos10311-84-9DialiphorHercules 14503ENT 27320DTXSID0037522O,O-Diethyl S-(2-chloro-1-phthalimidoethyl)phosphorodithioateS-(2-Chloro-1-phthalimidoethyl) O,O-diethyl phosphorodithioate8480K0VB4E
Weitere Namen anzeigen
imideH-14503ent27320rodithioate
Phosphorodithioic acid, O,O-diethyl ester, S-ester with N-(2-chloro-1-mercaptoethyl)phthalimidePhosphorodithioic acid, S-(2-chloro-1-phthalimidoethyl) O,O-diethyl esterS-(2-Chloro-1-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl)O,O-diethyl phosphorodithioateN-(2-Chloro-1-(diethoxyphosphinothioylthio)ethyl)phthalimideS-(2-Chloro-1-phthalmidoethyl)-O,O-diethylphosphorothionateDTXCID8017522Phosphorodithioic acid, S-(2-chloro-1-phthalimidoethyl)-O,O-diethyl esterO,O-Diethyl phosphorodithioate S-ester with N-(2-chloro-1-mercaptoethyl) phthalimide

Datenbank-Bezeichner

CAS
10311-84-9
PubChem CID
25146
DTXSID
DTXSID0037522
ChEMBL
CHEMBL1901826
ChEBI
CHEBI:82158
UNII
8480K0VB4E
EC Number
233-689-3
Nikkaji
J3.118F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
113 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
8
Schwere Atome
23

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 4 Einträge

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Dialifos) -> USDA PDB

LogP · 2 Einträge

log Kow = 4.69

4.69

Color/Form · 2 Einträge

White crystalline solid; also reported as oil

COLORLESS

Solubility · 5 Einträge

Sol in aromatic hydrocarbons, ethers, esters, ketones

Very soluble in cyclohexanone; slightly soluble in aliphatic hydrocarbons, alcohols

In acetone 760, isophorone 400, chloroform 620, xylene 570, diethyl ether 500, ethanol <10, hexane <10 (all in g/kg at 20 °C)

Soluble in common organic solvents

In water, 0.18 mg/L at 25 °C

CorrosivityNON-CORROSIVE

Physikochemische Eigenschaften

Schmelzpunkt
68 ℃ · 68℃
Siedepunkt
465.9 · 465.9±55.0 °C(Predicted)
Dichte
1.435 · 1.435±0.06 g/cm3(Predicted)
Flammpunkt
100 °C · 100 °C
storage temp.
0 · 0-6°C
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 2 Einträge

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsReleases nitrogen oxides, sulfur oxides, and phosphorus oxides when heated. Readily hydrolyzed by concentrated alkali. Avoid alkali. (EPA, 1998)
Health HazardsThis material can cause serious symptoms and in extreme cases death by respiratory arrest. (EPA, 1998)
Hazards Summary · 1 Eintrag

A cholinesterase inhibitor; [Hawley] A mild skin and eye irritant; In an exposure of 120 vineyard workers, symptoms included dizziness, weakness, headache, blurred vision, and tightness in the chest; Most plasma and red cell values were depressed more than 60%. All fully recovered, although 85 received medical attention and three were hospitalized; [HSDB] Some evidence of reproductive effects in feeding study with hamsters; [RTECS] No adverse gross or histopathological observations in three generation oral study with rats; No teratogenic effects observed in two studies with rabbits and one with macaques; No evidence of mutagenicity; No clinical observations of neurotoxicity in study with birds; Mildly irritating to skin and eyes of rabbits; Effects in high-dose feeding studies with rodents include cholinesterase inhibition and some evidence of liver necrosis; No significant effects observed in gross, histopathological, or tumor frequency in long term feeding studies with rats; [INCHEM JMPR] 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]

Reactive GroupAmides and Imides

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Organophosphorus Pesticide, Solid, n.o.s.) Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First AidWarning: Effects may be delayed up to 12 hours. Caution is advised.
Exposure Control and Personal Protection · 1 Eintrag

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 · 3 Einträge

This material may not burn but does ignite readily. For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use water spray, fog, or foam. Stay upwind; keep out of low areas. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter material. Wear positive pressure breathing apparatus and special protective clothing. Poisonous gases are produced in fire including nitrogen oxides, phosphorus oxides, and sulfur oxides. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. Containers may explode in fire. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.

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/

Storage ConditionsStore in tightly closed containers in a cool, well vented area away form strong bases.
Cleanup Methods · 1 Eintrag

Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

Toxikologische Informationen

Ecotoxicity Values · 5 Einträge

LC50 Salmo gairdneri (Rainbow trout) 0.55-1.08 mg/L/24 hr /Conditions of bioassay not specified/

LD50 (Apis mellifera) Honeybee 0.034-0.038 mg/bee

LD50 Mallard duck oral 940 mg/kg

LC50 Goldfish 1.80-8.30 mg/L/96 hr /Conditions of bioassay not specified/

For more Ecotoxicity Values (Complete) data for DIALIFOR (10 total), please visit the HSDB record page.

Environmental Fate · 4 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,500(SRC), determined from a log Kow of 4.69(2) and a regression-derived equation(3), indicates that dialifor is expected to be immobile in soil(SRC). Volatilization of dialifor from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 6.2X10-8 mm Hg(3), and water solubility, 0.18 mg/L(4). Aqueous hydrolysis half-lives of 1.8 hr at 37.5 °C and pH 7.4, 14 hr at 20 °C and pH 7.4, and 15 days at 20 °C and pH 6.1(5), indicate that hydrolysis may be an important fate process of dialifor in moist soil(SRC); however this process may be attenuated by adsorption. Dialifor is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data for dialifor were not available(SRC, 2007).

TERRESTRIAL FATE: Dialifor was reported to have a half-life of 11.9 days at 23.9 °C on foliage in grape fields(1). Dialifor exhibited half-lives of 140 and 150 days when applied to a moist clay loam at pH 6.2, 20 °C, and respective concns of 1 and 0.1 ppm(2).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,500(SRC), determined from a log Kow of 4.69(2) and a regression-derived equation(3), indicates that dialifor is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 6.2X10-8 mm Hg(4), and water solubility, 0.18 mg/L(4). According to a classification scheme(5), an estimated BCF of 820(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, dialifor undergoes rapid hydrolysis. Aqueous hydrolysis half-lives of 1.8 hr at 37.5 °C and pH 7.4, 14 hr at 20 °C and pH 7.4, and 15 days at 20 °C and pH 6.1(7), indicate that hydrolysis will be the primary fate process of dialifor in water. Biodegradation data for dialifor were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dialifor, which has a vapor pressure of 6.2X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dialifor is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.5 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dialifor may be removed from the air by wet or dry deposition(SRC). Dialifor does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Food Survey ValuesON ORANGES & LEMONS, RESIDUE HALF-LIFE OF TORAK WAS 40-60 DAYS & 60-80 DAYS. THERE WAS NO EVIDENCE OF PRESENCE OF THE OXYGEN ANALOG ... .
Adverse EffectsOther Poison - Organophosphate
Soil Adsorption/MobilityThe Koc of dialifor is estimated as 8500(SRC), using a log Kow of 4.69(1)and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dialifor is expected to be immobile in soil.
Human Toxicity Excerpts · 4 Einträge

/HUMAN EXPOSURE STUDIES/ Human volunteers were given Torak as corn oil soln or gelatin capsules: single daily doses of 0, 10, 0.03 or 0.1 mg/kg or three divided doses totaling 0, 0.01, 0.02, 0.03 or 0.95 mg/kg/day. Plasma cholinesterase & tributyrinase were inhibited @ 0.05 mg/kg or more, but diethylsuccinase was not inhibited at any dosage.

/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. Loss of Muscle Coordination, Slurring of Speech, Fasciculations & Twitching of Muscles (Particularly of Tongue & Eyelids), & Generalized Profound Weakness. 6. Mental Confusion, Disorientation & Drowsiness. /Parathion/

/SIGNS AND SYMPTOMS/ Symptomatology: 7. Difficulty in Breathing, Excessive Secretion of Saliva & of Resp Tract Mucus, Oronasal Frothing, Cyanosis, Pulmonary Rales & Rhonchi & Hypertension, (Presumably Due to Asphyxia). 8. Random Jerky Movements, Incontinence, Convulsions, & Coma. 9. Death Primarily Due to Resp Arrest Arising from Failure of Resp Center, Paralysis of Resp Muscles, Intense Bronchoconstriction or All Three. /Parathion/

/SURVEILLANCE/ Among a crew of 120 grape pickers (110 men and 10 women), 15 became sick one day, 100 additional workers became sick the next day, and three more became sick the 3rd day. Some were only dizzy or mildly weak. Others also had headaches, blurred vision, and tightness in the chest. Most plasma and red cell values were depressed more than 60%. Eighty-five of the workers received medical attention. Most were treated with atropine and some with 2-PAM. Three workers were hospitalized. Recovery was uneventful. The vineyard had been treated with dialifos and a less toxic compound, phosalone. On the basis of measurements made soon after the illnesses, it was concluded that the leaf residues of dialifos and of its oxon that caused poisoning were 100 and 2 ppm, respectively. Because of some evidence that the insecticide had been applied recently and in view of the relatively small proportion of oxon in the residues, this may have been an example of simple reentry poisoning.

Regulatorische Informationen

FIFRA Requirements · 1 Eintrag

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. Dialifor is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0010; Pesticide type: insecticide (acaricide); Registration Standard Date: 02/27/85; 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): Dialifor; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

CERCLA Reportable Quantities · 1 Eintrag

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Dialifor is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Sicherheitsdaten

ridadr
2783
RTECS-Nr.
TD5165000
risk_code
24-28-50/53
Toxizität
LD50 in adult male, female rats (mg/kg): 24, 6 orally (Gaines, Linder)
hazard_code
T+,N
safety_code
28-36/37-45-60-61

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

OPs /including dialifor/ 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...

Metabolism/Metabolites · 3 Einträge

Torak ... was almost completely metabolized when admin to dairy cow in feed (5 ppm) for 4 days. 3% of unchanged ... recovered from feces. ... urinary diethyl phosphorothionate accounted for 33% of the dose; only traces of diethyl phosphate were detected. Incubation ... with beef-liver prepn ... yielded diethyl phosphorothionate ... .

... /Torak/ was unchanged after 8 hr in presence of fresh rumen fluid ... .

First metabolic step is ... oxidation to the thiophosphate.

Absorption, Distribution and Excretion · 2 Einträge

Torak ... was almost completely metabolized when admin to dairy cow in feed (5 ppm) for 4 days. 3% of unchanged /Torak/ recovered from feces, but none was found in urine or milk. /Torak/

In mammals, following oral administration, dialifos is rapidly eliminated, principally in the urine, as the o-phthalic acid salt.

Verwendung und Herstellung

Uses · 6 Einträge

Used as acaricide and insecticide for fruits, nuts, potatoes, vegetables, cotton, and other crops; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For dialifor (USEPA/OPP Pesticide Code: 102501) there are 0 label matches. /SRP: Not registered for current 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./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

/DIALIFOS/ IS A NON-SYSTEMIC INSECTICIDE AND ACARICIDE EFFECTIVE IN CONTROLLING MANY INSECTS AND MITES ON APPLES, CITRUS, GRAPES, NUT TREES, OILSEED RAPE, POTATOES AND VEGETABLES

Methods of Manufacturing... BY CHLORINATION OF N-VINYLPHTHALIMIDE FOLLOWED BY REACTION WITH O,O-DIETHYL HYDROGEN PHOSPHORODITHIOATE.
Formulations/Preparations · 2 Einträge

'TORAK'; EMULSIFIABLE CONCENTRATE (240 AND 480 G TECHNICAL PRODUCT/L).

Dialifos is available in formulations of 24-72% emulsifiable concentrate.

Use ClassificationPharmaceuticals
General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies Dialifor (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

Anwendungen

VerwendenInsecticide; acaricide.

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