Tetradifon

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organochlorine Pesticides

Pesticide (Tetradifon) -> USDA PDB

log Kow= 4.61

4.6

4.61

1.151 @ 20 °C

Relative density (water = 1): 1.5

Crystals from benzene

White, crystalline powder

Solubility in acetone 67.3, methanol 3.46, ethyl acetate 67.3, hexane 1.52, dichloromethane 297, xylene 105 (all in g/L, 20 °C)

Soluble in aromatic hydrocarbon solvents, dioxan

AT 18 °C: 0.4 G/100 G PETROLEUM ETHER; 7.1 G/100 G ETHYL ACETATE; 10.5 G/100 G METHYL ETHYL KETONE; AND 1.6 G/100 G CARBON TETRACHLORIDE.

In water, 7.80X10-2 mg/L @ 20 °C

Sol in water ... at 20 °C, 0.08 mg/l.

Solubility in water at 20 °C: none

146.5 - 147.5 °C

MELTING POINT: 144 °C /Technical product/

148-149 °C

2.40X10-10 mm Hg at 20 °C

Vapor pressure, Pa at 20 °C:

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 3 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 (click each P-code to see the statement)

Tolerances are established for residues of the insecticide tetradifon (2,4,5,4'-tetrachlorodiphenyl sulfone) in or on raw agricultural commodities as follows: apple; apricot; cherry; citron, citrus; crabapples; cucumber; fig; fig, dried fruit; grapefruit; grape; hop, dried; hop, vine; lemon; lime; meat; melon; milk; nectarine; orange, sweet; peach; pear; peppermint; plum, prune, fresh; pumpkin; quince; spearmint, tops; strawberry; and tangerine.

Pesticide chemicals that cause related pharmacological effects will be regarded as having an additive deleterious action. Where residues from two or more chemicals in the same class are present in or on a raw agricultural commodity the tolerance for the total of such residues shall be the same as that having the lowest numerical tolerance in this class. Tetradifon is a member of the class of chlorinated organic pesticides.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetradifon is found on List B. Case No: 2655; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 4-Chlorophenyl 2,4,5-trichlorophenyl sulfone; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Acute Tox. 4 (100%)

Specific target organ toxicity - Single exposure - Category 2 (respiratory organs)

49 216 72; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, nec, other, than agricultural).

49 216 73; Organochlorine pesticide (compounds and preparations), solid (poison b) insecticides, agricultural, nec, other than liquid).

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.

Refer for medical attention .

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/

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.

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/

LD50 Mallard oral > 2,000 mg/kg, male, 4 mo old

LC50 Colinus virginianus (Bobwhite quail) dietary >5000 mg/kg/8 day

LC50 Coturnix japonica (Japanese quail) dietary >5000 mg/kg/8 day

LC50 Anas platyrhyncus (Mallard duck) dietary >5000 mg/kg/8 day

For more Ecotoxicity Values (Complete) data for TETRADIFON (12 total), please visit the HSDB record page.

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 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).

/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.

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.

/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.

Tetradifon concns averaged 1190 and 194 ng/g fresh weight in dead and live Mugil spp. viscera, respectively; tetradifon respective concns averaged 467 and 456 ng/g in dead and live Mugil spp. muscle taken from natural waters beside the Mediterranean sea(1).

Tolerances are established for residues of the insecticide tetradifon (2,4,5,4'-tetrachlorodiphenyl sulfone) in or on raw agricultural commodities as follows: apple; apricot; cherry; citron, citrus; crabapples; cucumber; fig; fig, dried fruit; grapefruit; grape; hop, dried; hop, vine; lemon; lime; meat; melon; milk; nectarine; orange, sweet; peach; pear; peppermint; plum, prune, fresh; pumpkin; quince; spearmint, tops; strawberry; and tangerine.

Pesticide chemicals that cause related pharmacological effects will be regarded as having an additive deleterious action. Where residues from two or more chemicals in the same class are present in or on a raw agricultural commodity the tolerance for the total of such residues shall be the same as that having the lowest numerical tolerance in this class. Tetradifon is a member of the class of chlorinated organic pesticides.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Tetradifon is found on List B. Case No: 2655; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): 4-Chlorophenyl 2,4,5-trichlorophenyl sulfone; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

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.

Used as acaricide (controls eggs and young mites) for deciduous fruits, citrus, cotton, vegetables, coffee, rice, tea, and other crops; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Acaracide. Ovicide on deciduous fruits, citrus, cotton and other crops.

Insecticide

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.

Prepn: produced by Friedel-Craft's reaction between 2,4,5-trichlorobenzenesulfonyl chloride and monochlorobenzene.

Prepn: ... /it is made/ by sandmeyer diazotization of 2,4,5-trichloro-4'-aminodiphenyl sulfone in presence of cuprous chloride.

Tetradifon is made by the reaction of chlorosulfonic acid plus 1,2,4- trichlorobenzene and benzene.

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.