Tetradifon
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Tetradifon
structure -
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CAS No:
116-29-0
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Formula:
C12H6Cl4O2S
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Chemical Name:
Tetradifon
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Synonyms:
Benzene,1,2,4-trichloro-5-[(4-chlorophenyl)sulfonyl]-;Sulfone,p-chlorophenyl 2,4,5-trichlorophenyl;1,2,4-Trichloro-5-[(4-chlorophenyl)sulfonyl]benzene;V 18;p-Chlorophenyl 2,4,5-trichlorophenyl sulfone;Duphar;Tedion;2,4,4′,5-Tetrachlorodiphenyl sulfone;Tedion V 18;Tetradifon;Tetradiphon;Mition;Roztoczol;Aredion;Akaritox;Polacaritox;Roztoczol extra
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CAS No:
Description
White, crystalline powder. Soluble in chloroform and aromatic hydrocarbons; insoluble in water.ChEBI: A sulfone that is diphenylsulfone in which one of the phenyl groups is substituted by chlorine at position 4, while the other is substituted by a chlorine at positions 2, 4, and 5.
COLOURLESS CRYSTALS.
Tetradifon is a sulfone that is diphenylsulfone in which one of the phenyl groups is substituted by chlorine at position 4, while the other is substituted by a chlorine at positions 2, 4, and 5. It is an organochlorine acaricide, a trichlorobenzene, a sulfone and a member of monochlorobenzenes.
Tetradifon Basic Attributes
356.05
356.05
204-134-2
TIP8EA8VTS
0747
DTXSID7021316
Crystals from benzene|White, crystalline powder
2930909054
Characteristics
42.5
4.6
COLOURLESS CRYSTALS.
1.151 g/cm3 @ Temp: 20 °C
146.5-147.5 °C
484.0±45.0 °C(Predicted)
246.5±28.7 °C
1.623
Solubility in water at 20°C: none
0-6°C
Vapour pressure, Pa at 20°C:
Oral-rat LD50: 566 mg/kg; Oral-dog LD50: 2000 mg/kg
Combustion produces toxic sulfur oxides and chloride gases
ODORLESS
Henry's Law constant = 1.44X10-9 atm-cu m/mol @ 25 °C /Estimated/
Off white to lightly yellowish substance /technical product/|/It is/ resistant to acid or alkali hydrolysis.|Extremely stable, even in strong acids and alkalis. Stable to heat and to sunlight. Resistant to strong oxidizing agents.|Off-white powder with a weak aromatic odor /Technical product/|Hydroxyl radical reaction rate constant = 3.64X10-13 cu cm/molecule-sec @ 25 °C /Estimated/
NON-CORROSIVE
Safety Information
UN30779/PG3
3
22-50/53
60-61
WR5850000
Xn,N
Storehouse ventilated at low temperature and dry; stored separately from oxidants (ammonium nitrate) and food additives
Resistant to strong oxidising agents.
P273-P501
H302-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.
WHO; Environ Health Criteria 67: Tetradifon p.9 (1986)
Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents.
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 198 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/
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. /Organochlorine pesticide, liquid/|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, dry chemical or carbon dioxide. /Organochlorine pesticides, solid, toxic/
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Organochlorine pesticide, 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./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. /Organochlorine pesticide, solid, toxic/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organochlorine pesticide, liquid/|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organochlorine pesticide, liquid/|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 solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Organochlorine pesticide, liquid/
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. ...Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. /Organochlorine pesticides, solid, toxic/|Personnel protection: Void breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organochlorine pesticide, liquid/|If material not of fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Organochlorine 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. Use water spray to knock-down vapors. /Organochlorine pesticide, liquid/
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.
Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
The substance may have effects on the kidneys and liver.
PREVENT DISPERSION OF DUST!
Use ventilation.
Protective gloves.
Wear safety spectacles.
Toxicity
moderately toxic
LD50 Rat oral >14,700 mg/kg|LD50 Rat oral 5000-14700 mg/kg /Technical tetradifon/|LD50 Dog oral 2000 mg/kg|LD50 Mouse ip 75 mg/kg|For more Non-Human Toxicity Values (Complete) data for TETRADIFON (7 total), please visit the HSDB record page.
/BIRDS and MAMMALS/ Tetradifon is relatively non-toxic for birds. ...Its toxicity /was studied/ for 4 species: bobwhite quail, ring-necked pheasant, mallard (all at 10 days of age), and 12-day-old Japanese quail. Tetradifon was included in food at concentrations of up to 5000 mg/kg and fed to the birds for 5 days. The mortality rate was estimated at 8 days. Bobwhite quail showed a 10% mortality rate at 5000 mg tetradifon/kg diet, but no deaths occurred in any other species.|/BIRDS and MAMMALS/ Signs of intoxication of mallards after oral administration of LD50 (more than 2000 mg/kg): ataxia, wing twitching, imbalance, and slowness. Signs appeared as soon as 1 hr after treatment. Remission had occurred by the day following treatment.|/AQUATIC SPECIES/ Waterfleas (Daphnia magna) were exposed to water suspensions of tetradifon of 0.2 or 2.0 mg/L for 48 hr (both concentrations exceed the water solubility of tetradifon). No toxic effects were observed.|/AQUATIC SPECIES/ The guppy (Lebistes reticulatus) showed signs of intoxication when exposed to tetradifon at 1 mg/L for 5 hr but recovered completely after being transferred to untreated water. Guppies, 3-4 weeks old, did not show any signs of intoxication when exposed to suspensions containing 2 mg technical tetradifon/L for 96 hr.|For more Ecotoxicity Excerpts (Complete) data for TETRADIFON (8 total), please visit the HSDB record page.
Tetradifon's former production and use(1) in the US as an acaricide(2) in airblast spray for fruit orchards(3) resulted in its direct release to the environment(SRC). The compound is manufactured in Spain(4).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7700(SRC), determined from a log Kow of 4.61(2) and a regression-derived equation(3), indicates that tetradifon is expected to be immobile in soil(SRC). Volatilization of tetradifon from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant estimated as 1.44X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.40X10-10 mm Hg(2), and water solubility, 7.80X10-2 mg/L(2). Tetradifon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). One persistence study indicated that 81% of tetradifon applied to an orchard with loamy soil (3.1% organic content, pH 7.4 and 26% clay) persisted for a minimum of 6 months; post application time was not given and samples were collected in the summer of 1967 and tested in 1968(4). Tetradifon did not persist in silty clay (4.9% organic content, pH 7.4 and 42% clay) approximately 2 yrs postapplication(4). Incubation of tetradifon with inocula of rumina bacteria or ciliated protozoa under anaerobic conditions suggests that tetradifon is not nutritionally used for growth of the organism and that this compound does not stimulate endogenous gas production(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7700(SRC), determined from a log Kow of 4.61(2) and a regression-derived equation(3), indicates that tetradifon 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 1.44X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 2.40X10-10 mm Hg(2), and water solubility, 7.80X10-2 mg/L(2). According to a classification scheme(4), an estimated BCF of 1900(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Based on a persistence study in soil(6), biodegradation of tetradifon in water may not be an imporatant fate process.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetradifon, which has a vapor pressure of 2.40X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase tetradifon may be removed from the air by wet and dry deposition(SRC). Particulate-phase tetradifon is stable in sunlight(3).
Tetradifon is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(1) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).
An estimated BCF of 1900 was calculated for tetradifon(SRC), using a log Kow of 4.61(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).
The Koc of tetradifon is estimated as 7,700(SRC), using a log Kow of 4.61(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that tetradifon is expected to be immobile in soil.
The Henry's Law constant for tetradifon is estimated as 1.44X10-9 atm-cu m/mole(SRC) derived from its vapor pressure, 2.40X10-10 mm Hg(1), and water solubility, 7.80X10-2 mg/L(1). This Henry's Law constant indicates that tetradifon is expected to be essentially nonvolatile from moist soil or water surfaces(2). Tetradifon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
SURFACE WATER: Tetradifon was qualitatively detected from natural waters beside the Mediterranean Sea in November of 1984(1). Tetradifon was qualitatively detected in Green Bay and the Fox River, two aquatic systems in the Lake Michigan water basin(2).
Tetradifon was detected at concns of 0.006 and 0.044 ppm in 2 of 216 total-diet samples from 18 markets consisting of 82 foods collected from 3 different geographical areas(1). Tetradifon was detected in 1 of 6 fruit composites from Boston, MA at a concn of 0.044 ppm, 2 of 6 fruit composites from Los Angeles, CA at concns of 0.006 and 0.011 ppm, and 1 of 6 meat, fish and poultry composites from Los Angeles, CA at a concn of 0.076 ppm from June 1965 to April 1966(2). During October 1, 1981 to September 30, 1986, tetradifon was found in 6 of 19,851 agricultural commodities at a concn range of >0-0.1 ppm(3). Tetradifon residues were qualitatively detected in 2 of 13,085 food samples during FY89(4) and it was found in raw agricultural commodities during FY78-82(5).
Occupational exposure to tetradifon in the past may have occurred through inhalation of dust and dermal contact with this compound at workplaces where tetradifon was produced or used. Monitoring data indicate that the general population may have been exposed to tetradifon ingestion of food and drinking water, and via inhalation of ambient air in the vicinity of spray operations. Current occupational and general population exposures in the United States are expected to be low or non-existent since tetradifon is no longer produced or used in the US(SRC). The compound is manufactured in Spain(1).|Potential dermal exposure of workers to tetradifon during airblast spraying of fruit orchards has been determined to be 36.4 mg/hr(1). Potential respiratory exposure of workers to tetradifon during airblast spraying of fruit orchards has been determined to be 0.07 mg/hr(1). In pesticide formulating plants, the most hazardous exposure of pesticides, such as tetradifon, may have been from spillage; furthermore, there was a high potential for exposure at mixing and bagging stations(1). Crop workers may have been unintentionally exposed to tetradifon during application; however, their main exposure resulted from contact with treated foliage or with pesticide or pesticide-contaminated material made airborne through agitation of foliage during work activity(1). Incidental to treating a crop, some pesticides, such as tetradifon, may have drifted onto workers in neighboring fields or in nearby suburban areas without there being any intent to treat those areas(1). Dusts tend to remain suspended longer than sprays, sometimes resulting in a cloud carried for a considerable distance from the point of release from an airplane(1). Therefore, exposure of the general population to tetradifon may have occurred through ingestion of contaminated foods(2,3) as well as from inhalation of dust and dermal contact resulting from spraying nearby fruit orchards(1).
Drug Information
In varying degrees, organochlorines are absorbed from the gut and also by the lung and across the skin. /Soild Organochlorines/|In rats, following oral administration of a single dose, 70% was excreted via the bile in the feces within 48 hr.
The 2 impurities 2,4,5-trichlorophenyl phenyl sulfone and dichlorophenyl phenyl sulfone were isolated from /technical grade/ tetradifon by GLC. They were identified by comparison for their mass spectra and retention times with those of synthesized samples. The impurities have identical mass no (m/e= 320) and very similar mass spectra and GLC retention times to those of 2,3,7,8-tetrachlorodibenzodioxin, a likely toxic impurity of tetradifon. This similarity can be a reason of substantial errors in the GLC determination or mass fragmentation of this toxic impurity.
Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Treatment is symptomatic and supportive. Oils should not be used as either cathartics or dermal cleansing agents, as they increase absorption. Gastric lavage and use of activated charcoal and sodium sulfate are indicated for ingestion. If dermal exposure occurred, contaminated clothes should be removed, and the skin should be thoroughly cleansed with soap and water. Management of seizures in both children and adults is with Valium or phenobarbital. Respiratory depression and even respiratory arrest, especially with concomitant use of Valium and phenobarbital in children, may occur. These drugs preferably should be used only in critical care areas where emergency endotracheal intubation can be performed. /It is recommended/ that epinephrine not be utilized in patients with organochlorine poisoning, as the organochlorines induce myocardial irritability and ventricular arrhythmias may occur. However, dopamine may be necessary in the event of hypotension unresponsive to fluid administration, and epinephrine may be necessary in the event of cardiopulmonary arrest. /Organochlorine insecticides/|Persons exceptionally exposed to organochlorine pesticides by any route should be observed for sensory disturbances, incoordination, speech slurring, mental aberrations, and involuntary motor activity that would warn of imminent convulsions. If convulsions occur, place the victim in the left lateral decubitus position with the head down. Move away furniture or other solid objects that may be a source of injury. If jaw movements are violent, place padded tongue blades between the teeth to protect the tongue. Whenever possible, remove dentures and other removable dental work. Aspirate oral and pharyngeal secretions, and, when possible, insert an oropharyngeal airway to maintain an open passage unobstructed by the tongue. Minimize noise and any manipulation of the patient that may trigger seizure activity. Administer oxygen by mask. Maintain pulmonary gas exchange by mechanically assisted ventilation whenever respiration is depressed. /Solid organochlorine insecticides/|If organochlorine has been ingested in a quantity sufficient to cause poisoning and the patient presents within an hour, consideration should be given to gastric decontamination procedures... If the patient presents more than an hour after ingestion activated charcoal may still be beneficial. If the victim is convulsing, it is almost always necessary first to control seizures before attempting gastric decontamination... /Solid organochlorine insecticides/|Do not give epinephrine, other adrenergic amines or atropine unless absolutely necessary because of enhanced myocardial irritability induced by chlorine hydrocarbons, which predisposes to ventricular fibrillation. Do not give animal or vegetable oils or fats by mouth. They enhance gastrointestinal absorption of the lipophilic organochlorines. /Solid organochlorine insecticides/
/HUMAN EXPOSURE STUDIES/ In photo-patch tests on 51 patients, ...tetradifon /was found/ to be one of the least active compounds of 29 pesticides tested.|/OTHER TOXICITY INFORMATION/ No reports of human poisonings have followed its extensive use in Europe.
2,4,4',5-tetrachlorodiphenyl sulfone
The substance can be absorbed into the body by inhalation of dust.
Redness.
Tetradifon Use and Manufacturing
Chlorosulfonation Trichlorobenzene is added dropwise to chlorosulfonic acid. Chlorosulfonic acid is excessive, the reaction temperature is 80~90℃, and the chlorosulfonation time is 3h. The gas discharged from the reaction is absorbed with water. The generated trichlorobenzenesulfonyl chloride is precipitated by cooling, washed with water (if necessary, a small amount of nitric acid is oxidized to convert the low sulfur compound into trichlorobenzenesulfonyl chloride), and finally dehydrated and dried for condensation. Condensation trichlorobenzenesulfonyl chloride and chlorobenzene condensation to form trichlorfon. The reaction is an electrophilic secondary reaction, using AlCl3 or FeCl3 as a catalyst, chlorobenzene is added dropwise, the reaction temperature is 145 to 155°C, and the reaction time is 1.5 to 3 hours. The condensation product was poured into hot water at 90°C, stirred and precipitated trichlorfon, washed and dried to obtain the original powder.
Acaricide.Ovicide on deciduous fruits, citrus, cotton and other crops.
Tedion V-18, emulsifiable concentrate (75.2 g ai/l), wettable powder (188 g/kg). Childion, Tedane, emulsifiable concentrate (tetradifon + dicofol); Dorvert, suspension concentrate (flowable) (50 g tetradifon + 150 g cyhexatin/l); Tedane combi, wettable powder 960 g tetradifon + 135 g dicofol + 50 g dinocap/kg); Turbair Acaricide ultra-low vol liquid (tetradifon + dicofol).|Emulsifiable concentrate, wettable powder, fumigant.|Mixed formulations: (tetradifon +) dicofol; binapacryl; fenitrothion; carbaryl; diazinon + methoxychlor; dicofol + dinocap; cyhexatin; omethoate; dioxathion; parathion.|Technical grade tetradifon is >/=95% pure.|For more Formulations/Preparations (Complete) data for TETRADIFON (6 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies Tetradifon (technical grade) as unlikely to present an acute hazard in normal use; Main Use: acaricide.|The wettable powder is recommended for citrus, coffee, bush fruit, top fruit, grapes, natural nursery stock @ 20 G AI/100 l; ornamentals and vegetables @ 20 G AI/100 l; the ec on cotton @ 240-400 G AI/100 l, groundnuts @ 10-20 G AI/100 tea at 16 G AI/100 l. At these rates it is non-phytotoxic & harmless to honeybee and the natural enemies of spider mites.|...Tetradifon resistance... is readily developed by Panonychus citri.|Compatible with other pesticides.
Product analysis is by gas liquid chromatography. Residues may be determined by gas liquid chromatography .|Nitration product when treated with alkali in presence of pyridine gives color read at 520 nm.|Total chlorine with biphenyl reagent in absence of other organochlorides. Pesticides plant growth regulators and food additives.|Residues may be determined by gas liquid chromatography.|For more Analytic Laboratory Methods (Complete) data for TETRADIFON (6 total), please visit the HSDB record page.
Agrochemicals -> Acaricides, Insecticides|ACARICIDES
Computed Properties
Molecular Weight:356.0
XLogP3:5.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:355.881311
Monoisotopic Mass:353.884261
Topological Polar Surface Area:42.5
Heavy Atom Count:19
Complexity:400
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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