Furathiocarb
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Furathiocarb
structure -
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CAS No:
65907-30-4
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Formula:
C18H26N2O5S
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Chemical Name:
Furathiocarb
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Synonyms:
6-Oxa-3-thia-2,4-diazadecanoic acid,2,4-dimethyl-5-oxo-,2,3-dihydro-2,2-dimethyl-7-benzofuranyl ester;CGA 73102;Deltanet;Furathiocarb;Promet 666SCO;Promet;78320-89-5
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CAS No:
Description
Furathiocarb is a carbamate ester and a member of 1-benzofurans. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide and an agrochemical.
Furathiocarb Basic Attributes
382.47
382.47
265-974-3
WZI2IZ80UY
DTXSID3052725
Yellow, viscous liquid.
Characteristics
93.6
4.70
Yellow, viscous liquid.
1.148 g/cm3 @ Temp: 20 °C
<25 °C
160 °C @ Press: 0.01 Torr
1.551
In water, 11 mg/l @ 25 deg C
0-6°C
3.9X10-3 mPa (2.9X10-8 mm Hg) @ 25 deg C
190.73 Ų [M+H]+ [CCS Type: TW]
Safety Information
I
6.1(a)
UN 2811
25-26-36/38-43-48/22-50/53
28-36/37-38-45-60-61
DF6652100
T+,N
Stable up to 400 deg C.
P260-P273-P280-P284-P301 + P310 + P330-P304 + P340 + P310
H301-H315-H317-H319-H330-H334-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, P305+P351+P338, P310, P314, P320, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P284, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P314, P320, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 197 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P284, P301+P310, P302+P352, P304+P340, P307+P311, P310, P312, P314, P320, P321, P330, P333+P313, P363, P403+P233, P405, and P501
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.|The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed at least once a week and each time it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Pesticides/|Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for FURATHIOCARB (16 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.|Severe marine pollutant
Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/
Toxicity
LD50 Rat oral 53 mg/kg|LD50 Mouse oral 327 mg/kg|LD50 Rat percutaneous >2,000 mg/kg|LC50 Rat inhalation 0.214 mg/l air/4 hr
/BIRDS and MAMMALS/ As a rule, birds are not very sensitive to carbamates... . /Carbamate pesticides/|/AQUATIC SPECIES/ Although carbamates are not very stable under aquatic conditions, and will not persist long in this environment, some carbamates are highly toxic for invertebrates and fish, others /are/ much less /toxic/. Some /carbamates/ bioaccumulate in fish, mainly because the metabolism is slow in /these animals/. /Carbamate pesticides/|/OTHER TERRESTRIAL SPECIES/ Toxic to bees.
Furathiocarb's production may result in its release to the environment through various waste streams; its use as an insecticide(1) results in its direct release to the environment(SRC). It is not registered for use in the US(2).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from a structure estimation method(2), indicates that furathoicarb is expected to have low mobility in soil(SRC). Volatilization of furathiocarb from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.9X10-8 mm Hg(3) and water solubility, 11 mg/l(3). Furathiocarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). In soil, furathiocarb is rapidly decomposed to carbofuran(3). The half-life of [14C-methyl]-furathiocarb in Montardon soil after pretreatment with various methylcarbamates is 3-6 days(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from a structure estimation method(2), indicates that furathiocarb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.9X10-8 mm Hg(4), and water solubility, 11 mg/l(4). According to a classification scheme(5), an estimated BCF of 830(SRC), from its log Kow of 4.70(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The half-life for furathiocarb in water at pH 9 is 4 days(4). Thiodicarb, a chemical that is structurally similar to furathiocarb, is stable in water at pH 6, and is rapidly hydrolyzed at pH 9 and slowly at pH 3(4). Aqueous suspensions of thiodicarb are decomposed in sunlight(4).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), furathiocarb, which has a vapor pressure of 2.9X10-8 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase furathiocarb 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 10 hours(SRC), calculated from its rate constant of 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase furathiocarb may be removed from the air by wet and dry deposition(SRC). Thiodicarb, a chemical that is structurally similar to furathiocarb, is susceptible to photolysis in aqueous suspension(2); however, no data were found regarding the direct photolysis of either of these chemicals by sunlight in air(SRC).
The rate constant for the vapor-phase reaction of furathiocarb with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The half-life for furathiocarb in water at pH 9 is 4 days(2). Thiodicarb, a chemical that is structurally similar to furathiocarb, is stable in water at pH 6, and is rapidly hydrolyzed at pH 9 and slowly at pH 3(2). Aqueous suspensions of thiodicarb are decomposed in sunlight(2).
An estimated BCF of 830 was calculated for furathiocarb(SRC), using a log Kow of 4.70(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), provided the compound is not altered physically or chemically after being released into the environment(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc for furathiocarb can be estimated to be 1,600(SRC). According to a classification scheme(2), this estimated Koc value suggests that furathiocarb is expected to have low mobility in soil.
The Henry's Law constant for furathiocarb is 1.3X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.9X10-8 mm Hg(1), and water solubility, 11 mg/l(1). This Henry's Law constant indicates that furathiocarb is expected to be essentially nonvolatile from water surfaces(2). Furathiocarb's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Furathiocarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Furathiocarb was analyzed for but not detected (detection limit=0.2 mg/kg) in the Danish National Pesticide Monitoring Program 1995-1996 for selected food commodities(1).
Occupational exposure to furathiocarb may occur through inhalation and dermal contact with this compound at workplaces where furthiocarb is produced or used. Monitoring data indicate that exposure to the general public is limited. (SRC)
Drug Information
Little information is available on the distribution of carbamates in the various organs and tissues in mammals following exposure by inhalation or the oral route. The organs in which residues have been reported are the liver, kidneys, brain, fat, and muscle.The half-life in the rat is of the order of 3 - 8 hr. It seems that the excretion of carbamates via urine is also rapid in man, and that the metabolic pathways in man are the same as those in the rat. /Carbamate pesticides/|The pharmacokinetics of furathiocarb were studied in vivo in male Sprague-Dawley rats following dermal treatment. HPLC and post-column derivatization were used for the analysis of furathiocarb and its metabolites (carbofuran, 3-hydroxycarbofuran and 3-ketocarbofuran). Carbofuran and 3-hydroxycarbofuran were detected in plasma and urine rather than furathiocarb. 3-Ketocarbofuran, another potential metabolite, was not observed in any sample. The concentration of carbofuran was higher than that of 3-hydroxycarbofuran in plasma, but the reverse was the case in urine. The corresponding area under the plasma concentration-time curve, Tmax, and Cmax values of carbofuran and 3-hydroxycarbofuran for 1,500 mg/kg doses were 2.4-8.0 mg equiv/ml, 12 hr and 0.1-0.4 mg equiv/ml, respectively. T1/2 was calculated only for 3-hydroxycarbofuran (28 hr). Two metabolites were excreted in a dose-dependent manner without saturation.
Metabolic transformation in rats proceeds via rapid and complete hydrolysis, followed by oxidation and conjugation. Excretion occurs mainly via kidney.|The first step in the metabolism of carbamates is hydrolysis to carbamic acid, which decomposes to carbon dioxide (CO2) and the corresponding amine. The mechanism of hydrolysis is different for N -methyl and N-dimethyl derivatives. The N-methyl carbamates pass through an isocyanate intermediate, whereas in the hydrolysis of N-dimethylcarbamates, an addition product with a hydroxyl ion is formed yielding the alcohol and N-dimethyl substituted acid. The rate of hydrolysis by esterases is faster in mammals than in plants and insects. Apart from hydrolysis, oxidation also takes place including: hydroxylation of the aromatic ring, O-dealkylation, N -methyl hydroxylation, N-dealkylation, oxidation of aliphatic side chains, and sulfoxidation to the corresponding sulfone. Oxidation is associated with the mixed-function oxidase (MFO) enzymes. Conjugation leads to the formation of O- and N- glucuronides, sulfates, and mercapturic acid derivatives in mammals. Glycosides and phosphates are conjugation products more common in plants. /Carbamate Pesticides/|The pharmacokinetics of furathiocarb were studied in vivo in male Sprague-Dawley rats following dermal treatment. HPLC and post-column derivatization were used for the analysis of furathiocarb and its metabolites (carbofuran, 3-hydroxycarbofuran and 3-ketocarbofuran). Carbofuran and 3-hydroxycarbofuran were detected in plasma and urine rather than furathiocarb. 3-Ketocarbofuran, another potential metabolite, was not observed in any sample. ...
The half-life in the rat is of the order of 3-8 hr. /Carbamate pesticides/
Carbamates are effective insecticides by virtue of their ability to inhibit acetylcholinesterase (AChE) in the nervous system. They also inhibit other esterases. The carbamylation of the enzyme is unstable, and the regeneration of AChE is relatively rapid compared with that from a phosphorylated enzyme. Thus, carbamate pesticides are less dangerous with regard to human exposure than organophosphorus pesticides. The ratio between the dose required to produce death and the dose required to produce minimum symptoms of poisoning is substantially larger for carbamate compounds than for organophosphorus compounds. /Carbamate pesticides/
Artificial respiration (via a tracheal tube) should be started at the first sign of respiratory failure and maintained for as long as necessary. Cautious administration of fluids is advised as well as general supportive and symptomatic pharmacological treatment and absolute rest. /Carbamate pesticides/|When dermal exposure occurs, decontamination procedures include removal of contaminated clothes and washing of the skin with alkaline soap or with a sodium bicarbonate solution. Particular care should be taken in the cleaning of the skin area where venupuncture is performed. Blood might be contaminated with carbamates and therefore inaccurate measures of ChE inhibition might result. Extensive eye irrigation with water or saline should also be performed. In the case of ingestion, ...gastric lavage (with the addition of bicarbonate solution or activated charcoal) can also be performed, particularly in unconscious patients, taking care to prevent aspiration of fluids into the lungs (i.e., only after a tracheal tube has been put in place). The volumes of the fluids introduced in the stomach should be recorded and samples of gastric lavage frozen and stored for subsequent chemical analysis. If the formulation of the pesticide involved is available, it should also be stored for further analysis (i.e., detection of toxicologically relevant impurities). A purge to remove the ingested compound can be administered. /Carbamate pesticides/|Specific pharmacological treatment: Atropine- ...The dose and the frequency of atropine treatment varies from case to case, but should maintain the patient fully atropinized (dilated pupils, dry mouth, skin flushing, etc.). Oxime reactivators- There is no rational basis for using these drugs. Furthermore, some unconfirmed reports suggest an increased toxicity of carbamates when oximes have been administered. Diazepam- Diazepam should be included in the therapy of all but the mildest cases. Besides relieving anxiety it appears to counteract some aspects of CNS-derived symptoms that are not affected by atropine. ...Other centrally acting drugs and drugs that may depress respiration are not usually recommended in the absence of artificial respiration procedures. /Carbamate pesticides/|The clinical approach to carbamate toxicity is similar to that for organophosphate poisoning; the major exception is that pralidoxime usually is not recommended. /Carbamates/|For more Antidote and Emergency Treatment (Complete) data for FURATHIOCARB (12 total), please visit the HSDB record page.
/SIGNS AND SYMPTOMS/ The clinical picture of carbamates intoxication results from accumulation of ACh at nerve endings. ...The signs and symptoms can be categorized into the following 3 groups: (a) Muscarinic manifestations - increased bronchial secretion, excessive sweating, salivation, and lachrymation; pinpoint pupils, bronchoconstriction, abdominal cramps (vomiting and diarrhea); and bradycardia. (b) Nicotinic manifestations - fasciculation of fine muscles (in severe cases, diaphragm and respiratory muscles also involved); and tachycardia. (c) Central nervous system manifestations- headache, dizziness, anxiety, mental confusion, convulsions, and coma; and depression of respiratory center. All these signs and symptoms can occur in different combinations and can vary in onset and sequence, depending on the chemical, dose, and route of exposure. The duration of symptoms is usually shorter than that observed in organophosphorus poisoning. Mild poisoning might include muscarinic and nicotinic signs only. Severe cases always show central nervous system involvement; the clinical picture is dominated by the respiratory failure sometimes leading to pulmonary edema due to the combination of the above mentioned symptoms. /Carbamate 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/
deltanit
Furathiocarb Use and Manufacturing
Granules, emulsifiable concentrate, capsule suspension|Liquid seed treatment|Tradenames: 'Deltanet' (Syngenta); 'Promet' (Syngenta).
The WHO Recommended Classification of Pesticides by Hazard identifies Furathiocarb (technical grade) as Class IB: highly hazardous; Main Use: insecticide-applied to soil: not used with herbicides or plant growth regulators.
Product analysis by glc. Residues determined by glc.
Agrochemicals -> Insecticides|Environmental transformation -> Pesticides (parent, predecessor)
Furathiocarb has known environmental transformation products that include carbofuran.
Computed Properties
Molecular Weight:382.5
XLogP3:4.7
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:382.15624311
Monoisotopic Mass:382.15624311
Topological Polar Surface Area:93.6
Heavy Atom Count:26
Complexity:502
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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