Dimefox (ISO)

Dimefox

HCID 8264CAS 115-26-4

Grundinformationen

Standard-SMILES
CN(C)P(=O)(F)N(C)C
InChIKey
PGJBQBDNXAZHBP-UHFFFAOYSA-N
Summenformel
C4H12FN2OP
Durchschnittliche Molmasse
154,12 g/mol
Monoisotopische Masse
154,06712785

Überblick

Dimefox is a colorless liquid with a fishy odor. Used as an insecticide; is neither produced nor used in the U.S. Not registered as a pesticide in the U.S. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Dimefox
IUPAC
N-[dimethylamino(fluoro)phosphoryl]-N-methylmethanamine
Lokaler Name
Dimefox (ISO)
Englischer Name
DIMEFOX
Summenformel
C4H12FN2OP
Molmasse
154.12

Namen und Synonyme

DIMEFOX115-26-4Tetramethylphosphorodiamidic fluorideTerrasytumHananeTerra-SytamPestox IVPestox XIVPestox 14Terra-SystamTetra SytamBFPO
Weitere Namen anzeigen
bfpEMTBs-14cr409tl792ZNF179RNF112R75574
DIFOWacker S 14/10Bis(dimethylamido)fluorophosphateBisdimethylaminofluorophosphine oxideFluophosphoric acid di(dimethylamide)Tetramethyldiamidophosphoric fluorideCR 409TL 792

Datenbank-Bezeichner

CAS
115-26-4
PubChem CID
8264
DTXSID
DTXSID8041870
ChEBI
CHEBI:82119
UNII
N8RU9F1IQD
EC Number
204-076-8
Nikkaji
J5.264G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,1
Polarare Oberfläche (TPSA)
23,6 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

SpringerMaterials Properties31P nuclear magnetic resonance spectrum
Pesticides · 3 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

LogPlog Kow = -0.43 /Estimated/
OdorFishy odor
Density · 3 Einträge

1.115 at 68 °F (EPA, 1998) - Denser than water; will sink

1.1151 at 20 °C/4 °C

1.115 @ 20°C

Color/FormColorless liquid

Physikochemische Eigenschaften

Siedepunkt
126 ℃ · 126℃ (60 Torr)
Dichte
1.1151 g/cm3 · 1.1151 g/cm3 (20 ºC)
Brechungsindex
1.4267 · 1.4267 (589.3 nm 20℃)
Flammpunkt
100 °C · 100 °C
storage temp.
4 °C · +4°C
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

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

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

Danger

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

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

Gefahrenhinweise

Regulatory Information2002/2076
DOT LabelPoison
Fire Hazards · 1 Eintrag

(Non-Specific -- Insecticide, Liquid, Poisonous, n.o.s.) Highly toxic fumes are given off upon decomposition with heat. Container may explode in heat of fire. Decomposes rapidly in the presence of chlorine. Oxidizes slowly in strong oxidizing agents. (EPA, 1998)

Health HazardsThis material is extremely toxic; the probable oral lethal dose (human) is 5-50 mg/kg, or 7 drops to 1 teaspoonful for a 150-lb. person. Death may occur from respiratory arrest. Hazards of vapor toxicity are high. (EPA, 1998)
Hazards Summary · 1 Eintrag

Very toxic cholinesterase inhibitor; [Merck Index] 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 GroupAmines, Phosphines, and Pyridines

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Insecticide, Liquid, Poisonous, n.o.s.) Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Ventilate closed spaces before entering them. Move container from fire area if you can do so without risk. 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 · 1 Eintrag

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. 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/

Storage Conditions · 4 Einträge

... 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 temperature ... 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 suitable distance from inhabited buildings, animal shelters, & food stores; moreover, they must be inaccessible to unauthorized persons, children, & domestic animals. /Prothoate/

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/

Nonfire Spill Response(Non-Specific -- Insecticide, Liquid, Poisonous, n.o.s.) Avoid inhalation. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors.

Toxikologische Informationen

Interactions · 3 Einträge

Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/

Barbiturates are potentiated by anticholinesterases. Although barbiturates may be used cautiously in treating convulsions, extreme care is essential in handling poisonings due to anticholinesterases, particularly organophosphorus pesticides. Echothiophate, a cholinesterase inhibitor used as miotic, potentiates other such inhibitors ... used for other purposes (additive effects) or possibly synergistic. Those exposed to organophosphate insecticides must take strict precautions. ... Organophosphorus insecticides: additive anticholinesterase effects. Hazardous. Patients on Anticholinesterases (even topical, such as eye drops) should avoid areas where organophosphorus insecticides /have/ recently /been/ used. /Anticholinesterase/

Anticholinesterase (organophosphorus) insecticides antagonize polarizing muscle relaxants. Phenothiazines /and thioxanthenes/: ... May enhance toxic effects of organophosphorus insecticides. /Organophosphorus insecticide/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.2(SRC), determined from a water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that dimefox is expected to have very high mobility in soil(SRC). Volatilization of dimefox from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.11 mm Hg(4), and water solubility, 1X10+6 mg/L (miscible)(2). Dimefox is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.2(SRC), determined from a water solubility of 1X10+6 mg/L (miscible)(2) and a regression-derived equation(3), indicates that dimefox is not 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 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.11 mm Hg(4), and water solubility, 1X10+6 mg/L (miscible)(2). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of -0.43(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Dimefox may hydrolyze in aquatic environments(SRC), based on a half-life of 8.8 days measured in an ethanol/buffer solution (20:80) at pH 6.0 and 70 °C(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimefox, which has a vapor pressure of 0.11 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimefox 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 6.0 hours(SRC), calculated from its rate constant of 6.40X10-11 cu cm/molecule-sec at 25 °C(3). Dimefox does not contain chromophores that absorb light at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOther Poison - Organophosphate
Medical Surveillance · 4 Einträge

Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications /meaning further clinical evaluations/ 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 /be protected from exposure from/ pesticides. /Organophosphorus pesticides/

... 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/

... There is no change in red blood cell cholinesterase activity in adults associated with age. ... Activity of this enzyme increases progressively during the first year of life, it is higher in children under 3 yr of age than in older children, and it is markedly higher in 5 yr old children than in 3 yr olds. /Organic phosphorus 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/

Soil Adsorption/Mobility · 1 Eintrag

The Koc of dimefox is estimated as 2.2(SRC), using a water solubility of 1X10+6 mg/L (miscible) (1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dimefox is expected to have very high mobility in soil.

Human Toxicity Excerpts · 5 Einträge

/HUMAN EXPOSURE STUDIES/ Amount too small for chem detection can cause blurred vision. Predominant effects are on peripheral tissue & not on CNS.

/HUMAN EXPOSURE STUDIES/ In a study lasting 70 days, whole blood cholinesterase was not inhibited in a total of four men and women who ingested the compound at a dosage of 0.002 mg/kg/day, but it was reduced about 25% by a dosage of 0.0034 mg/kg/day. In another study, a dosage of 0.004 mg/kg/day gradually caused a 40% reduction in whole blood cholinesterase by the 49th day of exposure when inhibition stabilized until dosing ended on the 95th day. This effect was entirely due to lowering of red cell cholinesterase since the plasma enzyme remained unchanged. Whole-blood activity recovered to 90% of normal within 56 days after dosing stopped ... .

/HUMAN EXPOSURE STUDIES/ A follow-up study of 232 people three years after a history of organophosphorus pesticide poisoning disclosed only one person with slight residual blurring of vision that might have been related to the earlier poisoning, though at the time of poisoning over one third of the people had blurring, which lasted only a day or two after exposure was discontinued. The possile exceptional case had findings suggestive of basilar artery insufficiency, rather than effects of poisoning. /Organophosphorus pesticide poisoning/

/HUMAN EXPOSURE STUDIES/ The effects of acute intoxication by anti-cholinesterase agents are manifested by muscarinic and nicotinic signs and symptoms and, except for compounds of extremely low lipid solubility, by signs referable to the CNS. Local effects are due to the action of vapors or aerosols at their site of contact with the eyes or respiratory tract, or due to the local absorption after liquid contamination of the skin or mucous membranes, including those of the gastrointestinal tract. Systemic effects appear within minutes after inhalation of vapors or aerosols. In contrast, the onset of symptoms is delayed after gastrointestinal and percutaneous absorption. The duration of effects is determined largely by the properties of the compound: its lipid solubility, whether it must be activated, the stability of the organophosphorus-AChE bond, and whether "aging" of the phosphorylated enzyme has occurred. /Anticholinesterase agents/

For more Human Toxicity Excerpts (Complete) data for DIMEFOX (19 total), please visit the HSDB record page.

Regulatorische Informationen

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. Dimefox is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Sicherheitsdaten

ridadr
3018
RTECS-Nr.
TD4025000
risk_code
27/28
Toxizität
LD50 in rats (mg/kg): 5.0 i.p.; 7.5 orally (Okinaka)
hazard_code
T+
safety_code
23-28-36/37-38-45

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 5 Einträge

A highly toxic cholinesterase inhibitor.

Unmetabolized dimefox is a moderately strong inhibitor of cholinesterase in vitro; the molar concentration required to cause 50% inhibition is 4x10-5. ... Its action is mainly peripheral, that on the brain being slower in onset.

The signs of poisoning due to organophosphorus cmpd are those due to accumulation of acetylcholine & hence overstimulation of parasympathetic nervous system. It is usual to divide them under 3 headings: muscarinic, nicotinic & central. Muscarinic signs ... consist of hypersalivation, lacrimation, sweating & nasal discharge. Miosis, dyspnea, vomiting, diarrhea & frequency of urination ... Nicotinic effects consist of fasciculation of muscles, weakness & paralysis. Central nervous system effects include nervousness, apprehension, ataxia, convulsions & coma. Death is due to resp failure, or sometimes cardiac arrest. There is little difference between signs produced by different organophosphorus compounds, but route of absorption may influence one system more than another. /Organophosphorus cmpd/

The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/

For more Mechanism of Action (Complete) data for DIMEFOX (10 total), please visit the HSDB record page.

Metabolism/Metabolites · 2 Einträge

Plasma and tissue enzymes are responsible for hydrolysis /of organophosphorus compounds/ to the corresponding phosphoric and phosphonic acids. However, oxidative enzymes are also involved in the metabolism of some organophosphorus compounds. /Anticholinesterase agents/

The organophosphorus anticholinesterase agents are hydrolyzed in the body by a group of enzymes known as A-esterases or paraoxonases. These enzymes are found in the plasma and liver and hydrolyze a large number of organophosphorus compounds ... by cleaving the phosphoester, anhydride, P-F, or P-CN bonds. /Anticholinesterase agents/

Absorption, Distribution and Excretion · 5 Einträge

Following oral administration to rats, elimination is via the urine.

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/

For more Absorption, Distribution and Excretion (Complete) data for DIMEFOX (8 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

Used as systemic insecticide and acaricide mainly for ornamental and non-food crops; [HSDB]

No longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For dimefox (USEPA/OPP Pesticide Code: 443100) there are 0 labels match. /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./

Systemic insecticide and acaricide /SRP 2005: former use/

A systemic pesticide primarily for ornamental and non-food plants /SRP 2005: former use/

U.S. Production · 2 Einträge

(1972) NOT PRODUCED COMMERCIALLY IN US

(1975) NONE

Methods of Manufacturing · 2 Einträge

Prepared by fluorination of bis(dimethylamido)phosphoryl chloride.

By interaction of dimethylamine, phosphoryl chloride, and potassium fluoride in chloroform (Brit patent 688,760).

Formulations/Preparations · 3 Einträge

Terra sytam butanol soln containing 50% wt/vol dimefox together with 17% total of schradan & hexamethyl pyrophosphoramide, which acts as synergist. S-14 is 20% aqueous dilution of terra systam.

Solution /contains/ 50 wt/vol; 10% for S 14/10*.

Technical contains schradan (q.v. ) and tris(dimethylamino)phosphine oxide.

General Manufacturing Information · 4 Einträge

The WHO Recommended Classification of Pesticides by Hazard identifies Dimefox (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.

It is compatible with other pesticides but technical product slowly attacks metals.

This compound ... has been used to control mealybug vector of swollen shoot disease of cacao by implanting soluble capsules about roots. Because of its volatility, dimefox has very short residual activity & is not suited for foliage application.

/Its/... main use is for soil treatment of hops against aphids & red spider mites, being effective, at non-phytotoxic concn, for 6-8 wk.

Anwendungen

VerwendenInsecticide; acaricide.

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