Isazofos
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Isazofos
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CAS No:
42509-80-8
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Formula:
C9H17ClN3O3PS
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Chemical Name:
Isazofos
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Synonyms:
Phosphorothioic acid,O-[5-chloro-1-(1-methylethyl)-1H-1,2,4-triazol-3-yl] O,O-diethyl ester;CGA 12223;Miral;Ciba-Geigy A 12223;A 12223;Isazophos;CIBA 12223;Miral 10G;Isazofos;Triumph;Brace 10G;Brace;Triumph (insecticide);57425-06-6;65357-77-9
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CAS No:
Isazofos Basic Attributes
313.74
313.74
255-863-8
CF67CG9STQ
DTXSID7034676
Amber liquid|Yellowish liquid|Yellow liquid
2933990012
Characteristics
90.5
3.82
1.22 g/cm3 @ Temp: 20 °C
<25 °C
170 °C @ Press: 760 Torr
188.1ºC
1.573
In water, 69 mg/l at 20 deg C
0-6°C
7.45 x 10 -3 Pa (20 °C)
LD50 in rats (mg/kg): 60 orally; 250-700 dermally (Dawes)
pKa=4.0
Safety Information
II
6.1(a)
3018
3
24/25-26-43-48/20-50/53
28-36/37-38-45-59-61
TE7760000
T+,N
P260-P273-P280-P284-P301 + P310-P310
H301 + H311-H317-H330-H373-H410
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.
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P314, P320, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. 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, dry chemical or carbon dioxide. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic/|If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) /Organophosphorus pesticides, solid, toxic/
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/|Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organophosphorus pesticides, liquid, flammable, toxic; Organophosphorus pesticides, liquid, toxic; Organophosphorus pesticides, solid, toxic/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, toxic|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, toxic/|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Organophosphorus pesticides, liquid, flammable, toxic/|For more Preventive Measures (Complete) data for ISAZOFOS (10 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.
Toxicity
The combination of certain herbicides with insecticides can inhibit crop growth. Greenhouse studies were conducted to evaluated interaction effects of herbicides and insecticides with/without protectant, on corn and weed species. 'Northrup King 9283' hybrid corn showed greater sensitivity to acetanilide herbicides than 'Cargill 7567'. Neither the insecticides terbufos nor isazofos appeared to enhance this sensitivity....
LC50 Rat inhalation 236 mg/cu m/4 hr|LD50 Rat skin 290 mg/kg|LD50 Rat oral 40-60 mg/kg|LD50 Rat (female) dermal 118 mg/kg.|LD50 Rat (male) dermal >3100 mg/kg.
/PLANTS/ Phytotoxic to potatoes and tobacco.
Isazofos' former production may have resulted in its release to the environment through various waste streams; its use as a nematicide and insecticide(1) resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 91.3 to 385(2), indicate that isazofos is expected to have high to moderate mobility in soil(SRC). Isazophos has a pKa of 4; in soils with lower pH, Koc values are expected to be higher as protonated species are readily sorbed to exchange sites in the soil(5). Volatilization of isazofos from moist soil surfaces is expected(SRC) given a Henry's Law constant of 5.21X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 8.7X10-5 mm Hg(4), and water solubility, 69 mg/l(4). Isazofos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Isazofos was reported to have a half-life in soil of 10 days in laboratory studies(3). Field half-lives of 34 days(4) and 2.5 to 48.4 days, have been reported(2). A half-life of 40 days at 25 deg has been reported for photolysis of isazofos on soil (pH 5)(2).|AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 91.3 to 385(7), indicates that isazofos may be expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(8) based upon a Henry's Law constant of 5.21X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 8.7X10-5 mm Hg(2), and water solubility, 69 mg/l(2). Using this Henry's Law constant and an estimation method(8), volatilization half-lives for a model river and model lake are 270 and 2000 days, respectively(SRC). According to a classification scheme(3), an estimated BCF of 170(SRC), from its log Kow of 3.82(4) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Isazofos is hydrolyzed more rapidly in alkali than in acids; half-lives were calculated at 20 °C as 85 days (pH 5), 48 days (pH 7), and 19 days (pH 9)(6). A half-life of 4 days at 25 deg has been reported for photolysis of isazofos in water (pH 7.5)(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isazofos, which has a vapor pressure of 8.7X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase isazofos 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 3.8 hours(SRC), calculated from its rate constant of 9.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase isazofos may be removed from the air by wet and dry deposition(SRC). While isazofos is susceptible to photolysis in water and on soil(4), no data were found regarding the direct photolysis in air of isazofos by sunlight(SRC).
The rate constant for the vapor-phase reaction of isazofos with photochemically-produced hydroxyl radicals has been estimated as 9.4X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.8 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Isazofos is hydrolyzed more rapidly in alkali than in acids; half-lives were calculated at 20 °C as 85 days (pH 5), 48 days (pH 7), and 19 days (pH 9)(2). Half-lives of 4 and 40 days at 25 deg have been reported for photolysis of isazofos in water (pH 7.5) and soil (pH 5), respectively(3).
An estimated BCF of 170 was calculated for isazofos(SRC), using a log Kow of 3.82(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).
102.33 L/kg|Koc values of 52.9, 91.3, 139, and 385 have been reported for isazofos in sand (pH 6.5, 0.9% organic matter), sandy loam (pH 8.5, 1.0% om), clay (pH 5.9, 4.8% om), and silt loam (pH 7.5, 1.0% om)(1). According to a classification scheme(2), Koc values in the ranges of 50-150 and 150-500 indicate high and moderate mobility, respectively. In a study using 1.2 meter deep soil monolith lysimeters with a turf cover, isazofos was not detected (detection limit=16 ug/l) in the percolate during the study, Sept 1991-Oct 1993(3). Isazofos was determined to be mobile in a Kentucky bluegrass turf managed as a golf course fairway(4).|Undisturbed soil columns under an irrigation regime similar to agricultural practice (150 ml/day/column) were used to study the mobility of isazophos in soil over 13 weeks(1). 37.15, 1.4, and 0.1% of the initial concn was found in the soil profile, the water leachates and the plant material, respectively(1). Koc values varied with 2190 reported in the top 20 cm and 4320 from the 40 cm depth(1). The pH of the soils used was not provided(1). Mobility of commercial formulations of isazophos was studied using field lysimeters (packed with Honeywood silt loam; 1.5 to 2.8% organic matter) under two moisture regimes(2). Isazophos was eluted from 9 of 12 cores following watering during the first week of the experiment; however, no further elution was reported for the remainder of the experiment(2). Total amounts of isazophos below 10 cm never exceeded 2% of the applied product(2). Kd values of 2.828 and 1.336 were determined(2). Kd values from 0.81 to 2.82 were reported for soils containing organic matter from 2.0 to 4.9%(3). Isazophos has a pKa of 4; in soils with lower pH, Koc values are expected to be higher as protonated species are readily sorbed to exchange sites in the soil(4). Leaching of isazophos was less than 0.1% of the applied amount during a 6 month field study(5).|Persistence of isazophos, as either an emulsifiable concentrate or as granules, was measured in field lysimeters packed with Plainfield sand (1.5% organic matter) and receiving either natural rainfall or supplementary watering(3). Neither isazophos or its metabolite, CGA 17193 (5-chloro-1-isopropyl-3-triazolol), were found in the effluent of lysimeters receiving only rainfall over the 21 week period (223 mm rain fell)(1). Isazophos, applied as an emulsifiable concentrate, was eluted on 22 occasions from the lysimeters; however, when applied as granules, only 4 instances of isazophos elution were reported (total water input of 811 mm)(1).
The Henry's Law constant for isazofos is 5.21X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 8.7X10-5 mm Hg(1), and water solubility, 69 mg/l(1). This Henry's Law constant indicates that isazofos is expected to volatilize slowly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 270 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 2000 days(SRC). Isaozofos' Henry's Law constant indicates that volatilization from moist soil surfaces is expected(SRC). Isazofos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). Pesticides were applied to a 0.2 ha plot of established creeping bentgrass at an on-going field turf experiments in Amherst, Massachusetts, and the concentrations of the pesticides in air were measured following their application(3). Maximum isazofos vapor concentrations for 2 days following three pesticide applications at 2302, 2573, and 2838 g/ha were 0.35, 0.72, and 0.62 ug/cu m, respectively(3).
Occupational exposure to isazofos may have occurred through inhalation and dermal contact with this compound at workplaces where isazofos was produced or used. Occupational exposure and general population exposure should be low or non-existent since isazofos is no longer produced or used. (SRC)|Secondary exposure of children through contact with their parents' contaminated clothing can also occur. /Organophosphorus pesticides/
Drug Information
Metabolism occurs principally by oxidation, hydrolysis by esterases, and by transfer of portions of the molecule to glutathione. Oxidation of organophosphorus insecticides may result in more or less toxic products. The glutathione transferase reactions produce products, that are, in most cases, of low toxicity. Hydrolytic and transferase reactions affect both thioates and their oxons. /Organophosphorus Pesticides/
Organophosphorus insecticides exert their acute effects in both insects and mammals by inhibiting acetylcholinesterase (AChE) in the nervous system with subsequent accumulation of toxic levels of acetylcholine (ACh), which is a neurotransmitter. In many cases, the organophosphorylated enzyme is fairly stable, so that recovery from intoxication may be slow. /Organophosphorus Pesticides/
Airway protection. Ensure 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/|Atropine sulfate. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access if difficult to obtain. ...The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate disposition of organophosphate. Recrudescence of poisoning may occur if tissue concentrations of organophosphate remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but it is ineffective against nicotinic actions, specifically muscle weakness and twitching, and respiratory depression. Despite the limitations, atropine is often a life-saving agent in organophosphate poisonings. Favorable response to a test dose of atropine ...can help differentiate poisoning by anticholinesterase agents from other conditions. However, lack of response, with no evidence of atropinization (atropine refractoriness) is typical of more severe poisonings. The adjunctive use of nebulized atropine has been reported to improve respiratory distress, decrease bronchial secretions, and increase oxygenation. ...Do not administer atropine or pralidoxime prophylactically to workers exposed to organophosphate pesticides. Prophylactic dosage with either atropine or pralidoxime may mask early signs and symptoms of organophosphate poisoning and thus allow the worker to continue exposure and possibly progress to more severe poisoning. Atropine itself may enhance the health hazards of the agricultural work setting: impaired heat loss due to reduced sweating and impaired ability to operate mechanical equipment due to blurred vision. This can be caused by mydriasis, one of the effects of atropine. /Organophosphate pesticides/|Glycopyrolate has been studied as an alternative to atropine and found to have similar outcomes using continuous infusion. Ampules... of glycopyrolate were added to... saline and this infusion was titrated to the desired effects of dry mucous membranes and heart rate above 60 beats/min. During this study, atropine was used as a bolus for a heart rate less than 60 beats/min. The other apparent advantage to this regimen was a decreased number of respiratory infections. This may represent an alternative when there is a concern for respiratory infection due to excessive and difficult to control secretions, and in the presence of altered level of consciousness where the distinction between atropine toxicity or relapse of organophosphate poisoning is unclear. /Organophosphate pesticides/|Pralidoxime. Before administration of pralidoxime, draw a blood sample (heparinized) for cholinesterase analysis (since pralidoxime tends to reverse the cholinesterase depression). Administration pralidoxime (Protopam, 2-PAM), a cholinesterase reactivator, in cases of severe poisoning by organophosphate pesticides in which respiratory depression, muscle weakness, and/or twitching are severe. When administered early (usually less than 48 hours after poisoning) pralidoxime relieves the nicotinic as well as the muscarinic effects of poisoning. Pralidoxime works by reactivating the cholinesterase and also by slowing the "aging" process of phosphorylated cholinesterase to a non-reactivatable form. ...Dosage of pralidoxime may be repeated in 1-2 hours, then at 10-12 hour intervals if needed. In very severe poisonings, dosage rates may be doubled. Repeated doses of pralidoxime are usually required. In cases that involve continuing absorption of organophosphate (as after ingestion of large amounts), or continuing transfer of highly lipophilic organophosphate from fat into blood, it may be necessary to continue administration of pralidoxime for several days beyond the 48 hour post-exposure interval usually cited as the limit of its effectiveness. ...Blood pressure should be monitored during administration because of the occasional occurrence of hypertensive crisis. Administration should be slowed or stopped if blood pressure rises to hazardous levels. Be prepared to assist pulmonary ventilation mechanically if respiration is depressed during or after pralidoxime administration. If intravenous injection is not possible, pralidoxime may be given by deep intramuscular injection. /Organophosphate pesticides/|For more Antidote and Emergency Treatment (Complete) data for ISAZOFOS (17 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ Signs and symptoms of acute intoxication by organophosphorus insecticides include muscarinic, nicotinic, and central nervous system (CNS) manifestations. Symptoms may develop rapidly, or there may be a delay of several hours after exposure before they become evident. The delay tends to be longer in the case of more lipophilic compounds, which also require metabolic activation. Symptoms may increase in severity for more than one day and may last for several days. In severe cases, respiratory failure is a dominant effect. /Organophosphorus Pesticides/|/SIGNS AND SYMPTOMS/ Principal effects /of anticholinesterases as toxic components of insecticides/ on eye, whether from local contact or systemic poisoning, are miosis and spasm of accommodation for near vision. /Anticholinesterases/
CGA 12223
Isazofos Use and Manufacturing
Isocyanate Preparation of Chlorocarbonyl Phenyldichloride Tetracarbamoyl chloride reacts with carbon tetrachloride to remove hydrogen chloride to produce methyl isocyanate, and then to pass chlorine gas under light, chlorination temperature 35℃, and chlorine flux per hour 15 ~18g, reaction time is more than 10h, chlorinated liquid is distilled under normal pressure, and the fraction of 115~118℃ is collected, the yield is 70%. For the preparation of isopropylhydrazine, add isopropyl bromide dropwise to 85% hydrazine hydrate. The dropwise addition temperature is less than 35°C. The addition is completed in about 2 to 3 hours. The temperature is raised to 55 to 60°C and the reaction is performed for 3 hours. Cool and extract with ether, yield 65%. After neutralization with hydrochloric acid, concentration and crystallization to obtain isopropylhydrazine hydrochloride. Preparation of isoxazolol Isopropylhydrazine or isopropylhydrazine hydrochloride and solvent were cooled to below 20 °C, and equimolar chlorocarbonyl isocyanide dichloride was added dropwise at a temperature of 20 °C for 20 min. It was stirred at room temperature for 1 h, heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated under reduced pressure. The residue was recrystallized to obtain a white solid, mp 98-100 °C, yield 45%. Synthesis of chlorazophos. Izozole, anhydrous potassium carbonate and solvent were heated and refluxed for 2h, cooled to room temperature, and equimolar O, O-diethylthiophosphoryl chloride was added dropwise. After the completion of the drip, the temperature was raised to reflux for 3h. Filtration and filtrate desolvation under reduced pressure to obtain a yellow transparent liquid, n20D1.4868, yield >90%. Urea Phosgene Method
Nematocide; turf insecticide.
Emulsifiable concentrates, granules|Tradenames: 'Brace' * (Ciba-Geigy); 'Miral' * (Novartis); 'Triumph' * (Ciba-Geigy); 'Victor' * (Ciba-Geigy) .
The WHO Recommended Classification of Pesticides by Hazard identifies Isazofos (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|The basic producer of isazophos is Syngenta
FDA Method 232.4. Organophosphorous Residues General Methods for Nonfatty Foods Using Acetone Extraction and Isolation in Organic Phase. Analysis by GLC.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:313.74
XLogP3:3.9
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:313.0416773
Monoisotopic Mass:313.0416773
Topological Polar Surface Area:90.5
Heavy Atom Count:18
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Recommended Suppliers of Isazofos
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