Menazon

pp175 · sayfor · sayfos · syphos · r15,175 · saiphos · sayphos · MENAZON

Identifikatoren & physikalische Daten

CAS No.	78-57-9
Summenformel	C6H12N5O2PS2
Durchschnittliche Molmasse	281,3 g/mol
Monoisotopische Masse	281,01700325 g/mol
SMILES	COP(=S)(OC)SCc1nc(N)nc(N)n1
InChIKey	SUYHYHLFUHHVJQ-UHFFFAOYSA-N
PubChem CID	6543
ChEBI	CHEBI:82140
EC No.	201-123-4
DTXSID	DTXSID9042120
Lokaler Name	Menazon

Chemische & physikalische Eigenschaften

XLogP	0,5
Polarare Oberfläche (TPSA)	167
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	9
Frei drehbare Bindungen	5
Schwere Atome	16
Formalladung	0
Komplexität	253
Pestizide	Pesticides -> Organophosphate Insecticides
Geruch	LITTLE OR NO ODOR
Color/Form	COLORLESS CRYSTALS
Löslichkeit	LOW SOLUBILITY IN WATER & ORG SOLVENTSGENERALLY SOL TO ABOUT 10-20% IN HYDROXYLIC SOLVENTSAT ROOM TEMP: 200 G/KG 2-ETHOXYETHANOL, 250 G/KG 2-METHOXYETHANOL, 150 G/KG TETRAHYDROFURFURYL ALCOHOL, 100 G/KG ETHYLENE GLYCOLIn water, 240 mg/l at 20 °C0.24g/L(20 ºC)
Schmelzpunkt	FP: 164-166 °C164-166°
Dampfdruck	0.00000097 [mmHg]9.75X10-7 mm Hg at 25 °C
Food Contact Substances	FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description	Off-white solid[Hawley] Colorless solid[HSDB]
Stability/Shelf Life	SOLID IS STABLE @ TEMP UP TO 50 °C
Dissociation Constants	pKa=3.8
Other Experimental Properties	DECOMP 160-162 °CIt is decomp by strong acids and lyesFORMS CRYSTALLINE PICRATE, HYDROCHLORIDE & DIHYDROGEN CITRATEMERCAPTAN-LIKE ODOR /TECHNICAL PRODUCT/
Siedepunkt	89.5°C
Dichte	1.548±0.06 g/cm3(Predicted)
pKa (Säurekonstante)	4.10±0.10(Predicted)
Farbe	Crystals from MeOH
Henry-Konstante	6.6×103 mol/(m3Pa) at 25℃, HSDB (2015)
CAS Datenbank	78-57-9
EPA chemische Informationen	Menazon (78-57-9)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Gefahrenübersicht	Very toxic cholinesterase inhibitor[Hawley] No significant adverse effects observed in animal studies besides inhibition of cholinesterase activity[HSDB] 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]
Other Hazardous Reactions	A portion of even the most flammable materials is likely to be lost by vaporization. ... The smoke from an open fire used to destroy pesticides will contain some of the poison. Burning should be attempted only in an isolated place. Inhalation of smoke must be avoided. /Pesticides/
Hazard Classes and Categories	Acute Tox. 4 (100%)Acute toxicity - category 4Acute toxicity (Oral) - Category 4Acute Tox. 4 *
Standard Transportation Number	49 216 74Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)49 216 75Organophosphorus pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, liquid)49 105 4449 105 4549 216 76Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (insecticides, other than agricultural, NEC)49 216 77Organophosphorus pesticide, solid, not otherwise specified (compounds and preparations) (agricultural insecticides, NEC, other than liquid)
Shipment Methods and Regulations	No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMO	UN 3018Organophosphorus pesticides, liquid, toxic, not otherwise specifiedUN 3017Organophosphorus pesticides, liquid, toxic, flammable, not otherwise specified, flashpoint between 23 °C and 61 °CUN 2783Organophosphorus pesticides, solid, toxic, not otherwise specifiedUN 2784Organophosphorus pesticides, liquid, flammable, toxic, not otherwise specified, flashpoint less than 23 °CFor more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for MENAZON (6 total), please visit the HSDB record page.
Expositionsschutz und Persönliche Schutzausrüstung	Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs]
Brandbekämpfungsverfahren	If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/
Lagerbedingungen	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 availablefloors 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/
Entsorgungsverfahren	SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Hydrolysis: Mix menazon with lime and sand or other adsorbent in a pit or trench at least 0.5 m deep in a clay soil. Soda ash can be added to the mixture to help speed the reactions when lime is used as the main alkali. Recommendable methods: Incineration & landfill. Peer-review: Large amt: Incinerate in a unit with effluent gas scrubbing (Peer-review conclusions of an IRPTC expert consultation (May 1985))All organic pesticides, whether of botanical or synthetic origin, can be destroyed by incineration. /Organic pesticides/Manufacturers or formulators of very large amounts of pesticides may find it advantageous to build incinerators adequate to destroy all organic pesticides and equipped with scrubbers to remove acid wastes. /Organic pesticides/
Preventive Measures	In some situations where personnel may become accidently contaminated ... it is necessary to provide shower bath in addition to the usual washing facilities. Special arrangements for cleaning clothing & overalls may be necessary ... /Pesticides/Special aircraft should preferably be used for spraying or dusting toxic organophosphorus pesticides. ... aerial spraying or dusting gives rise to clouds which spread over larger surfaces than clouds produced by ground application. Aerial spraying should therefore be carried out on windless days only. Residential areas, water supply sources, etc must be avoided. ... When aircraft approaches, signalmen /guiding the aircraft/ should leave the windward side. ... The local population should be informed about the site & time of aerial pesticide treatment. Access of unauthorized persons & especially children to the area to be treated must be ... forbidden. Warning signs should be placed at the limits of the area. Ground spraying must be carried out with compressed-air spraying equipment towed by tractors with closed cabs. /Organophosphorus pesticides/Small packages of pesticides are preferable for individual application in order to limit the quantities to be weighed & metered. A special vessel with long stirring rod for dilution & suspension of the poison must be available in order to reduce manual handling to a minimum. The strict observance of hygiene rules--no smoking & no food intake during work. Thorough washing with soap after work, changing protective clothing before going home--is of utmost importance. /Organophosphorus pesticides/Containers ... should be cleaned with a suspension of bleaching powder in water or with other alkaline soln after soaking for 24 hr and then be rinsed with hot water. /Organophosphorus pesticides/For more Preventive Measures (Complete) data for MENAZON (8 total), please visit the HSDB record page.
Personal Protective Equipment (PPE)	Respiratory protection (supplied-air respirator with full facepiece or self-contained breathing apparatus) should be available where these compounds are manufactured or used and should be worn in case of emergency and overexposure. /Phosphorus compounds/WORKERS HANDLING AND APPLYING ORGANOPHOSPHATE PESTICIDES (OPP) MUST ... BE GIVEN PERSONAL PROTECTIVE EQUIPMENT COMPRISING OVERALLS MADE OF A TIGHT FABRIC OR POLYVINYL CHLORIDE, GLOVES, AND RUBBER BOOTS. THEY MUST WEAR A RESPIRATOR WITH AN ACTIVATED-CARBON GAS FILTER CARTRIDGE AFFORDING PROTECTION FOR A DETERMINED NUMBER OF WORKING HOURS. THE EYES SHOULD BE PROTECTED BY GOGGLES. THE SIGNALMEN FOR AERIAL DUSTING OPERATIONS SHOULD BE EQUIPPED WITH A HAT AND CAPE MADE OF POLYVINYL CHLORIDE OR A FABRIC IMPREGNATED WITH A WATER REPELLENT. /PESTICIDES, ORGANOPHOSPHORUS/
Wechselwirkungen	.../MENAZON/ CAN CAUSE PARALYTIC EFFECTS IN ATROPINIZED HENS...EFFECTS OCCUR WITHIN 24 HR OF EXPOSURE & HENS RECOVER IN ABOUT A MONTH.Some phenothiazines may antagonize & some may potentiate the toxic anticholinesterase effects of ... /organophosphorus insecticides/. /Organophosphate cholinesterase inhibitors/In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/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 ... RECENTLY ... USED. /ANTICHOLINESTERASE/ANTICHOLINESTERASE (ORGANOPHOSPHORUS) INSECTICIDES ANTAGONIZE POLARIZING MUSCLE RELAXANTS. PHENOTHIAZINES /AND THIOXANTHENES/: ... MAY ENHANCE TOXIC EFFECTS OF ORGANOPHOSPHORUS INSECTICIDES. /INSECTICIDES, ORGANOPHOSPHORUS/
Ökotoxizitätswerte	LC50 Harlequin fish 220 mg/l/48 hr
Umweltverhalten	TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 210(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(3), indicates that Menazon will have moderate mobility in soil(SRC). Based on limited data, Menazon is expected to biodegrade in soil(SRC). A half-life of 23 days was measured for Menazon (at 10 ppm) in a sandy loam soilMenazon at 250 ppm disappeared at a similar rate(4). Volatilization of Menazon should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.5X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(5) and water solubility(2). Volatilization from dry soil surfaces(SRC) is not expected based on a measured vapor pressure of 9.75X10-7 mm Hg(4). This compound is expected to photodegrade on soil surfacesin sunlight, Menazon photooxidizes with the conversion of the P:S group to P:O with a decomposition half-life of 10.5 hours(6).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 210(SRC), determined from a measured water solubility(2) and a recommended regression-derived equation(1), indicates that Menazon may adsorb to suspended solids and sediment in water(SRC). Based on limited data from soil studies, Menazon may biodegrade in water(SRC). A half-life of 23 days was measured for Menazon (at 10 ppm) in a sandy loam soilMenazon at 250 ppm disappeared at a similar rate(3). Menazon should not volatilize from water surfaces based on an estimated Henry's Law constant of 1.5X10-9 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(2). An estimated BCF value of 30(1,SRC), from a measured water solubility(2), suggests that Menazon may moderately bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), Menazon, which has an estimated vapor pressure of 9.75X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase Menazon 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 about 5 hours(3,SRC). Particulate-phase Menazon may be physically removed from the air by wet and dry deposition(SRC).
Unerwünschte Wirkungen	Other Poison - Organophosphate
Medical Surveillance	Workers handling & applying pesticides must undergo an annual medical examination at the beginning of each agricultural season. Contraindications for work with /organophosphorus pesticides/ are organic diseases of the central nervous system, mental disorders & epilepsy, pronounced endocrine & vegetative disorders, pulmonary tuberculosis, bronchial asthma, chronic respiratory diseases, cardiovascular diseases & circulatory disorders, gastrointestinal diseases (peptic ulcer), gastroenterocolitis, diseases of liver & kidneys, eye diseases (chronic conjunctivitis & keratitis). The blood cholinesterase activity must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in cholinesterase activity of 25% or more must be transferred to other work where they are not exposed to organophosphorus pesticides until this activity is completely restored. Persons with initial signs of indisposition should cease work with pesticides. /Organophosphorus pesticides/A final diagnosis of mild to moderate acute organophosphate pesticide poisoning is rarely justified unless all of the following five conditions are present: 1. A definite history of exposure to an organophosphate pesticide. 2. A latent interval of not more than a few hours between that last exposure and the onset of illness. 3. A clinical picture in which most or all of the following signs or symptoms are present: headache, blurred vision, weakness, tightness in chest, and constricted pupils. 4. Reduction of plasma and RBC cholinesterase activity to a level substantially below 50% of baseline values. Because of the wide normal range of RBC cholinesterase in the population, symptoms may be present with reported "normal" levels. 5. An acute illness that is not substantially longer than 48 hours. The classic presentation for acute organophosphate toxicity includes history, evidence of exposure to organophosphate (garlic odor), signs/symptoms of cholinergic excess, improvement with atropine or pralidoxime, and inhibition of cholinesterase in blood. /Organophosphate pesticide poisoning/... Surveillance of workers could be carried out through measurement of blood or urinary levels of the cmpd to which they are exposed, or through measurement of a metabolite. /Organic phosphorus pesticides/
Soil Adsorption/Mobility	The Koc of Menazon is estimated as approximately 210(SRC), using a measured water solubility of 240 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that Menazon has moderate mobility in soil(SRC). Menazon penetrated in small amounts, to about 15 cm depth, when applied to the soil surface(4).
Human Toxicity Excerpts	...CHOLINESTERASE INHIBITORAll the organophosphorus insecticides have a cumulative effect by progressive inhibition of cholinesterase ... /Organophosphorus insecticides/The symptoms of chronic poisoning due to organophosphorus pesticides include headache, weakness, feeling of heaviness in head, decline of memory, quick onset of fatigue, disturbed sleep, loss of appetite, & loss of orientation. Psychic disorders, nystagmus, trembling of the hands & other nervous system disorders can be observed in certain cases. Sometimes neuritis, paresis & paralysis develop. /Organophosphorus pesticides/Organophosphorus cmpd can produce dermal irritation but most are weak sensitizers. /Organophosphate cmpd/For more Human Toxicity Excerpts (Complete) data for MENAZON (17 total), please visit the HSDB record page.
Artificial Pollution Sources	If Menazon is used as an insecticide and acaricide(1) and as a systemic aphicide(2), then it will be released to the environment(SRC).
Environmental Biodegradation	A half-life of 23 days was measured for Menazon (at 10 ppm) in a sandy loam soilMenazon at 250 ppm disappeared at a similar rate(1).
Environmental Bioconcentration	An estimated BCF value of 30 was calculated for Menazon(SRC), using a measured water solubility(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms is moderate, not high(SRC).
Volatilization from Water/Soil	The Henry's Law constant for Menazon is estimated as 1.5X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 9.75X10-7 mm Hg(1), and water solubility, 240 mg/l(2). This value indicates that Menazon will be essentially nonvolatile from water surfaces(3,SRC). Menazon's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces should not occur(SRC).
Non-Human Toxicity Excerpts	LISTED AS RELATIVELY SAFE ORGANOPHOSPHATE (RAT ACUTE ORAL LD50 GREATER THAN 500 MG/KG BODY WT) /FROM TABLE/...RABBITS TREATED FOR 24 HR WITH 500 TO 800 MG/KG ON SHAVED BACK SUFFERED NO LOCAL OR SYSTEMIC TOXIC EFFECTS. NINETY-DAY 'NO EFFECT' LEVEL IN RAT IS 30 PPM. IN 2 YR STUDY @ 4000, 1000 & 250 PPM IN DIET...NO SIGNIFICANT EFFECTS OTHER THAN ON CHOLINESTERASE.Menazon is an effective insecticide for mustard aphid control, with little toxicity to the predator Coccinella septempunctata, as shown by median lethal concn values.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/For more Non-Human Toxicity Excerpts (Complete) data for MENAZON (7 total), please visit the HSDB record page.
R-Sätze (R)	22-52/53
Toxizität	LD50 orally in male, female rats: 1020, 1450 mg/kg (Gaines)
Gefahrensymbole	Xn
Sicherheitshinweise (S)	61
Gefahrstoffdaten	78-57-9(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Insecticide; acaricide.