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Pesticides -> Organophosphate Insecticides

Pesticide (Famphur) -> USDA PDB

Oil/water partitioning coefficient: 2.23 (log)

2.28

CRYSTALS

Colorless crystalline powder

Famphur is a crystalline powder. Very toxic. Cholinesterase inhibitor. Restricted use as insecticide.

Colorless solid; [HSDB]

173.8 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID7041966]

182.13 Ų [M+Na]+

169.47 Ų [M+H]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Danger

H300 (92.9%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

A cholinesterase inhibitor; [Hawley] Caused inhibition of cholinesterase activity in rats, birds, and livestock; [HSDB] A highly toxic cholinesterase inhibitor; [CAMEO] No adverse effects to fertility observed in cattle; No information found with regards to teratogenicity or effects on lactation; [REPROTOX] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]

Famphur is used as a pour-on formulation for the control of cattle grubs and to reduce cattle lice infestation to be used at the rate of 1 ounce per 200 pounds body weight, not to exceed a total dosage of 4 ounces. Famphur is to be applied as soon as possible after heel fly activity ceases. Not to be usd on lactating dairy cows or dry dairy cows within 21 days of freshening calves less than 3 months old, animals stressed from castration over-excitement or dehorning, sick or convalescent animals. Animals may be dehydrated and under stress following shipment. Do not treat Brahman bulls.

Famphur is a cholinesterase inhibitor. Do not use this product in animals with exposure to cholinesterase-inhibiting drugs pesticides or chemicals. Limited for beef cattle and nonlactating dairy cows; feed for 10 days; withdraw from dry dairy cows and heifers 21 days prior to freshening; withdraw 4 days prior to slaughter.

Eisler R; Famphur Hazards to Fish, Wildlife, and Invertebrates: A Synoptic Review. NTIS/PB94-156767; Govt Reports Announcements & Index (GRA&I), Issue 13, (1994). Famphur is administered to livestock by intramuscular or subcutaneous injections through the diet, as a dermal pour-on, or as an oral bolus.

P097; As stipulated in 40 CFR 261.33, when famphur, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Tolerances are established for residues of the insecticide O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphorothioate including its oxygen analog (O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphate) in or on the raw agricultural commodities meat, fat, and meat by products of cattle.

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. Famphur (O,O-dimethyl O-(p-(dimethylsulfamoyl)phenyl) phosph is found on List D. Case No: 4039; 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): Famphur (O,O-dimethyl O-(p-(dimethylsulfamoyl)phenyl) phosph; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Organothiophosphates, such as FAMPHUR, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P097, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Potential candidate for liquid injection incineration with a temperature range of 650 to 1600 °C and residence times of 0.1 to 2 seconds. Also, a potential candidate for rotary kiln incineration with a temperature range of 820-1600 °C and residence times of liquids and gases, seconds; solids, hours. Also, a potential candidate for fluidized bed incineration with a temperature range of 450-980 °C and residence times for liquids and gases, seconds; solids, longer.

Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/

Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

If material not on fire and not involved in fire: Keep sparks, flames, and othersources 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, NOS/

Personnel protection: Keep upwind. Wear appropriate chemical protective gloves, boots and goggles. Do not handle broken packages unless wearing appropriate personal protective equipment. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Organophosphorus pesticides, liquid, NOS/

If material not on fire and not involved in fire: Keep sparks, flames, and othersources of ignition away. Keep material out of water sources and sewers. /Organophosphorus pesticides, solid, NOS/

Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Wear appropriate chemical protective gloves, boots and goggles. 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 protective clothing. /Organophosphorus pesticides, solid, NOS/

Tolerances are established for residues of the insecticide O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphorothioate including its oxygen analog (O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphate) in or on the raw agricultural commodities meat, fat, and meat by products of cattle at 0.1 ppm.

LD50 ANAS PLATYRHYNCHOS (MALLARD) ORAL 9.87 MG/KG (95% CONFIDENCE LIMIT 5.88-16.6 MG/KG), 3-4 MO OLD MALES

LC50 COTURNIX JAPONICA (JAPANESE QUAIL) ORAL 68 PPM IN 5-DAY DIET (95% CONFIDENCE LIMIT 59-78 PPM), AGE 14 DAYS (TECHNICAL GRADE)

LC50 PHASIANUS COLCHICUS (RING-NECKED PHEASANT) ORAL 49 PPM IN 5-DAY DIET (95% CONFIDENCE LIMIT 40-61 PPM), AGE 10 DAYS (TECHNICAL GRADE)

LC50 ANAS PLATYRHYNCHOS (MALLARD DUCK) ORAL APPROX 35 PPM IN 5-DAY DIET, AGE 10 DAYS (TECHNICAL GRADE)

For more Ecotoxicity Values (Complete) data for FAMPHUR (6 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a calculated log Kow of 2.28 obtain from its water solubility(1,2), a soil adsorption coefficient (Koc) of 419 can be obtained for famphur(2,SRC). This value suggests that famphur will display moderate mobility in soil(3), and may be expected to adsorb to soil(SRC). Hydrolysis in moist soils may occur by analogy to its behavior in water(4), however, it is not expected to be a rapid fate process(SRC).

AQUATIC FATE: Hydrolysis under neutral conditions is expected to occur slowly, as an experimental half-life of 115 days has been obtained(1). Hydrolysis in basic waters is expected to occur at a more rapid rate, with an experimental half-life of 6 and 60 days at pH 11 and pH 10, respectively(1,SRC). A calculated Koc of 419(2,SRC), based on the estimated log Kow, 2.289(3), suggests that famphur would be expected to adsorb to sediment and suspended organic matter(SRC). A calculated bioconcentration factor of 31.8(2,SRC), also based on log Kow(3), suggests that bioconcentration in fish and aquatic organisms is not expected to be a significant fate process(SRC).

Based on a calculated log Kow of 2.28 obtain from its water solubility(1,2), a soil adsorption coefficient (Koc) of 419 can be obtained for famphur(2,SRC). This value suggests that famphur will display moderate mobility in soil(3), and may be expected to adsorb to soil(SRC).

Veterinarians treating grub infestations in cattle with pour-on applications of famphur and other organic phosphorus pesticides in poorly ventilated areas occasionally reported nausea, headaches, and irritation of the throat and facial skin. Blood cholinesterase activities were not reduced in these cases, and alkyl phosphate metabolites were only occasionally found in the urine.

Famphur was produced commercially for use as an insecticide, and in the control of cattle grubs, reindeer grub fly, the reindeer nostril fly, and to reduce lice infestations(1,2). It may have entered the environment as a fugitive emission during its manufacture and formulation, or as a result of its application to control pests(SRC). The EPA lists famphur's status as cancelled(3).

BO-ANA FAMPHUR IS A CHOLINESTERASE-INHIBITOR. ... ON OCCASION, CATTLE TREATED WITH BO-ANA MAY SHOW SIGNS OF ORGANOPHOSPHATE POISONING.

SIGNS OF INTOXICATION /IN MALE MALLARD DUCKS ADMIN ORALLY 35% PURE FAMPHUR AT LD50 OF 9.87 MG/KG (RANGE 5.88-16.6) WERE/ REGURGITATION, GOOSE-STEPPING ATAXIA, WING DROP, TREMORS, TONIC SEIZURES.

ORAL FAMPHUR CAUSED REDN IN PLASMA CHOLINESTERASE ACTIVITY @ 25 PPM IN FEMALE RATS @ 45 DAYS, IN WHOLE BLOOD CHOLINESTERASE @ 3 AND 25 PPM, & IN BRAIN CHOLINESTERASE @ 25 PPM. IT CAUSED INCR IN GLUTAMIC PYRUVIC TRANSAMINASE IN FEMALES IN THE 3 AND 25 PPM 90 DAY GROUP. A SIGNIFICANT INCR IN THE PACKED CELL VOLUME OF FEMALE RATS EXPOSED TO 3 PPM FOR 45 DAYS WAS ALSO OBSERVED.

FREE LIVING NESTLING STARLINGS WERE DOSED WITH 0, 0.3, 1.0 OR 3.0 MG FAMPHUR/KG/DAY. ON DAY 19, BRAIN CHOLINESTERASE IN BIRDS DOSED WITH 3 MG WAS 85% BELOW CONTROLS. BRAIN & PLASMA CHOLINESTERASE ACTIVITY LEVELS OF BIRDS IN 1.0 & 0.3 MG/KG GROUP WERE ALSO BELOW CONTROLS.

For more Non-Human Toxicity Excerpts (Complete) data for FAMPHUR (10 total), please visit the HSDB record page.

An experimental rate constant for the hydrolysis of famphur under neutral conditions at 25 °C has been determined to be 2.5X10-4 1/hr, corresponding to a calculated half life of 115 days(1). The rate constant for hydrolysis under basic conditions at 25 °C has been determined to be 5 l/m hr at pH 11 (1), which corresponds to a half-life of approximately 6, and 60 days at pH 11 and pH 10, respectively(SRC).

Famphur is used as a pour-on formulation for the control of cattle grubs and to reduce cattle lice infestation to be used at the rate of 1 ounce per 200 pounds body weight, not to exceed a total dosage of 4 ounces. Famphur is to be applied as soon as possible after heel fly activity ceases. Not to be usd on lactating dairy cows or dry dairy cows within 21 days of freshening calves less than 3 months old, animals stressed from castration over-excitement or dehorning, sick or convalescent animals. Animals may be dehydrated and under stress following shipment. Do not treat Brahman bulls.

Famphur is a cholinesterase inhibitor. Do not use this product in animals with exposure to cholinesterase-inhibiting drugs pesticides or chemicals. Limited for beef cattle and nonlactating dairy cows; feed for 10 days; withdraw from dry dairy cows and heifers 21 days prior to freshening; withdraw 4 days prior to slaughter.

P097; As stipulated in 40 CFR 261.33, when famphur, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

Tolerances are established for residues of the insecticide O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphorothioate including its oxygen analog (O,O-dimethyl-O-p-(dimethylsulfamoyl) phenyl phosphate) in or on the raw agricultural commodities meat, fat, and meat by products of cattle.

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. Famphur (O,O-dimethyl O-(p-(dimethylsulfamoyl)phenyl) phosph is found on List D. Case No: 4039; 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): Famphur (O,O-dimethyl O-(p-(dimethylsulfamoyl)phenyl) phosph; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1,000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Organophosphorus derivatives act by combining with and inactivating the enzyme acetylcholinesterase (AChE). ... The inactivation of cholinesterase by cholinesterase inhibitor pesticides allows the accumulation of large amounts of acetylcholine, with resultant widespread effects that may be ... separated into 4 categories: (1) Potentiation of postganglionic parasympathetic activity. ... (2) Persistent depolarization of skeletal muscle ... (3) Initial stimulation following depression of cells of central nervous system ... (4) Variable ganglionic stimulation or blockade ... /Cholinesterase inhibitor pesticides/

FAMPHUR WAS DEGRADED AT VARYING RATES BY MICE, AMERICAN COCKROACH, AND MILKWEED BUGS. ... IN ADDITION TO FAMPHUR, BOTH FAMOXON AND N-DESMETHYL FAMPHUR WERE FOUND. TWO WHITE-FACED WESTERN EWES & ONE HEIFER CALF WERE TREATED WITH TRITIATED FAMPHUR. IN ADDITION TO THE OXYGEN ANALOG, O-DESMETHYL, O,N-BISDESMETHYL, TWO GLUCURONIDES, P-HYDROXYBENZENESULFONIC ACID, AND SEVERAL UNKNOWN METABOLITES WERE OBSERVED. IN RATS, MAJOR METABOLITE WAS DIMETHYLSULFAMOYLPHENYL GLUCURONIDE. O,N-BISDESMETHYL FAMPHUR, METHYLSULFAMOYLPHENYL GLUCURONIDE, AND P-HYDROXYBENZENE SULFONIC ACID WERE ALSO OBSERVED.

FAMPHUR WAS DEGRADED AT GREATLY DIFFERING RATES IN MICE, FEMALE AND MALE COCKROACHES, AND MILKWEED BUGS. N-DEMETHYLATION OCCURRED ONLY IN INSECTS.

Famphur was injected into muscle of reindeer. Residues /famphur and its oxon/ were detectable for 4.5 days in liver, 12 days in kidney, 12 days in shoulder muscle. After 20 days, a residue was found only at site of injection in shoulder muscle.

WHEN SHEEP WERE TREATED IV, FAMPHUR WAS ELIMINATED RAPIDLY, WITH 98% OF THE ADMIN DOSE BEING RECOVERED WITHIN 48 HR & NEARLY ALL OF THE RADIOACTIVITY BEING EXCRETED IN THE URINE. AFTER IM ADMIN, 64% OF ADMIN DOSE WAS RECOVERED IN EXCRETA AFTER 72 HR.

SC FAT FROM COWS TREATED @ 150 MG FAMPHUR/KG BODY WT CONTAINED MAX RESIDUES OF FAMPHUR (ABOUT 10 PPM, AVG) 1 DAY AFTER TREATMENT. LEVELS OF TREATMENT @ 50 MG/KG AND 25 MG/KG YIELDED RESIDUES OF 2.08 & 1.8 PPM, RESPECTIVELY.

Used as veterinary insecticide for grubs and lice; [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."

Registration cancelled

MEDICATION (VET)

To a mixture of N,N-dimethyl-1-phenol-4-sulfonamide (5.0 g, 0.025 mol) and sodium hydroxide (1.0 g, 0.025 mol) in 50 ml of water are added separately and simultaneously O,O-dimethyl phosphorochloridothioate (4.0 g, 0.025 mol) and a solution of sodium hydroxide (1.0 g, 0.025 mol in 25 ml water).

ONE GALLON OF BO-ANA POUR-ON CONTAINS 1.04 LB OF FAMPHUR.

FAMIX MEDICATED PREMIX, ADMIN IN FEED. /DATA FROM TABLE/

Formulation type Pour-on; Dustable powder

Phosphorothioic acid, O-[4-[(dimethylamino)sulfonyl]phenyl] O,O-dimethyl ester: ACTIVE

PREPN: BERKELHAMMER, US PATENT 3,005,004 (1961 TO AMERICAN CYANAMID).

POUR BO-ANA FAMPHUR ALONG BACKLINE FROM SHOULDERS TO TAILHEAD AT RATE OF 1 OZ/200 LB WT. DO NOT REPEAT TREATMENT. TREATMENT WITHIN 4-6 WK OF GRUB EMERGENCE IS OF LITTLE VALUE AND MAY RESULT IN TOXIC EFFECTS DUE TO KILLING OF MIGRATING LARVAE. TREATMENT IS LESS EFFECTIVE IN WET ANIMALS OR ANIMALS EXPOSED TO RAIN AFTER TREATMENT.