ホスホロジチオ酸O-エチルO-[4-(メチルチオ)フェニル]S-プロピル

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Sulprofos) -> USDA PDB

Pesticide

log Kow = 5.48

5.48

4.9

Phosphorus odor

Mercaptan-like odor

1.2 (NIOSH, 2024) - Denser than water; will sink

1.20 at 20 °C/20 °C

1.2 g/cm³

1.20

1.20

Low (NIOSH, 2024)

Sol in organic solvents.

In water, 0.31 mg/l at 20 °C

Solubility in water, mg/l at 20 °C: 0.31 (very poor)

Low

155-158 °C at 0.1 mm Hg

155 °C

-15 °C /technical grade/

-15 °C

less than 8 mmHg (NIOSH, 2024)

0.0000012 [mmHg]

0.084 mPa (6.3X10-7 mm Hg) at 20 °C; 0.16 mPa (1.2X10-6 mm Hg) at 25 °C

Vapor pressure, Pa at 20 °C:

<8 mmHg

<8 mmHg

Danger

H301+H311 (41.4%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard Traits - Environmental tox

2002/2076

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.

High concentrations may cause CNS effects; Cholinesterase inhibitor; [ICSC] 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]

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. Sulprofos is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0076; Pesticide type: insecticide; Registration Standard Date: 08/07/1981; Case Status: The last registered pesticide products containing this pesticide were voluntarily cancelled by their registrants while EPA was developing the RED; Active ingredient (AI): sulprofos; Data Call-in (DCI) Date(s): 08/20/1990, 06/28/1991, 10/13/1995; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled.".

Organothiophosphates 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.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Use alcohol-resistant foam, powder, carbon dioxide.

Fresh air, rest. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

Excerpt from NIOSH Pocket Guide for Sulprofos:

(General first aid procedures)

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: 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/

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/

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 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.

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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 worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

For more Preventive Measures (Complete) data for SULPROFOS (13 total), please visit the HSDB record page.

A combination of sulprofos and malathion caused a fivefold potentiation of acute oral toxicity in rats, based on oral LD50s. Similarly, a simultaneous dosing of sulprofos and azinphos-ethyl yielded a threefold potentiation of toxicity.

In long term therapy, adrenocorticoids antagonize the antiglaucoma effects of anticholinesterases (incr ocular pressure). ... Anticholinergics antagonize the miotic (antiglaucoma) & other muscarinic effects of anticholinesterases on the autonomic & central nervous systems. Tricyclic antidepressants (anticholinergic effects) antagonize the antiglaucoma (miotic) effects of anticholinesterases in glaucoma. ... Antihistamines with anticholinergic effects antagonize the miotic (antiglaucoma) & CNS effects of anticholinesterases. Anticholinesterases potentiate tranquilizing & behavioral changes induced by antihistamines. The actions of anticholinesterase agents on autonomic effector cells, & to some extent those on CNS, are antagonized by atropine, an antidote of choice. Barbiturates are potentiated by anticholinesterases. ... Dexpanthenol potentiates the effects of anticholinesterases. Fluorophosphate insecticides potentiate the effects of other anticholinesterases. /Anticholinesterases/

Barbiturates are potentiated by anticholinesterases. Although barbiturates may be used cautiously in treating convulsions, extreme care is essential in handling poisonings due to anticholinesterases, particularly organophosphorus pesticides. Echothiophate, a cholinesterase inhibitor used as miotic, potentiates other such inhibitors... used for other purposes (additive effects) or possibly synergistic. Those exposed to organophosphate insecticides must take strict precautions. ...Organophosphorus insecticides: additive anticholinesterase effects. Hazardous. Patients on anticholinesterases (even topical, such as eye drops) should avoid areas where organophosphorus insecticides... recently... used. /Anticholinesterase/

Anticholinesterase (organophosphorus) insecticides antagonize polarizing muscle relaxants. Phenothiazines /and thioxanthenes/: ...May enhance toxic effects of organophosphorus insecticides. /Insecticides, organophosphorus/

LC50 Goldfish (Carassius auratus) 30 mg/L/96 hr /Conditions of bioassay not specified in source examined/

LC50 Carp (Cyprinus carpio) 10 mg/L/96 hr /Conditions of bioassay not specified in source examined/

LD50 Anas platyrhynchos (Mallard duck) eggs exposed once for 30 sec in an 18 day study period, 34 lb/acre application rate (95% confidence interval: 22-52 lb/acre)

LC50 Anas platyrhynchos (Mallard duck, 11 day old) diet 983 ppm/ 8 day (95% confidence interval: 732.5-1,320.9 ppm)

For more Ecotoxicity Values (Complete) data for SULPROFOS (14 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 12,000(2) and 13,500(3), measured in soil, indicate that sulprofos is expected to have no mobility in soil(SRC). Volatilization of sulprofos from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.6X10-7 atm-cu m/mole derived from its vapor pressure, 6.3X10-7 mm Hg(4), and water solubility, 0.31 mg/l(4). Sulprofos is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). The half-life of sulprofos in soils ranges from several days to several weeks depending upon soil type, and the major metabolites are sulprofos sulfoxide and sulprofos sulfone(4). Hydrolysis in moist soils may occur based on hydrolysis half-lives in water (22 °C) of 26, 151, and 51 days at pH 4, 7, and 9, respectively(4).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 12,000(2), and 13,500(3) measured in soil, indicate that sulprofos is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 8.6X10-7 atm-cu m/mole derived from its vapor pressure, 6.3X10-7 mm Hg(5), and water solubility, 0.31 mg/L(5). According to a classification scheme(6), an estimated BCF of 3300(SRC), from a log Kow of 5.48(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). The hydrolysis half lives of sulprofos at 22 °C are 26 days at pH 4, 151 days at pH 7 and 51 days at pH 9(5). Sulprofos is also expected to undergo biodegradation in aquatic environments based on shake-flask tests containing estuarine water only or estuarine water and sediment(8). First order rate constants were 0.00817 1/hr in sediment/water slurries and 0.00148 1/hr in water, respectively(8); corresponding to half-lives of 3.5 days and 19.5 days, respetively.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulprofos, which has a vapor pressure of 6.3X10-7 mm Hg at 20 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase sulprofos 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 4 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase sulprofos may be removed from the air by wet and dry deposition(SRC). Sulprofos is also susceptible to direct photolysis; for thin films in sunlight, 50% decomposition was observed in <2 days(2).

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

inhalation, ingestion

Results of five field studies reporting the half-lives of dislodgeable residues on cotton plants in Arizona were: 1.0, 0.9, 0.76, 0.8, and 0.6 days(1). In these studies 0 to 12.3 mm of rain fell and the mean temperature ranged from 27.0 to 31.4 °C. A similar study in Texas resulted in a half-life of 0.5 days(1). In a study of foliar washoff, sulprofos was applied to mature cotton plants as an emulsifiable concentrate with a water carrier and simulated rain (51 mm in 1 hr) was applied at different times after application(2). Residues became increasingly resistant to washoff with increasing time interval between application and initial rainfall with 92%, 75%, and 50% washoff when the initial rain occurred 2, 29, and 146 hours after application. The mean amount of insecticide washed from the plants were related to the mean loading on the plants and decreased with time. On the average, the first 2 to 3 minutes of rain removed 50% of the total amount of insecticide washed from the plants by the 51 mm rainfall. After fully expanded leaves of field-grown cotton plants were treated in-situ with 100 ug of 32P- or 14C-labeled sulprofos, it was found that about half the dose was absorbed, mostly during the first day(3). Surface and internal residues of the insecticide and its toxic derivatives diminished to insignificant levels after 8 and 32 days, respectively.

Pupillary constriction, muscle cramp, excessive salivation. Headache. Sweating. Dizziness. Nausea. Diarrhoea. Vomiting. Laboured breathing. Unconsciousness. Symptoms may be delayed.

MAY BE ABSORBED! Further see Inhalation.

Blurred vision.

See Inhalation.

nausea, vomiting, abdominal cramps, diarrhea, salivation; headache, dizziness, lassitude (weakness, exhaustion); rhinorrhea (discharge of thin nasal mucus), chest tightness; blurred vision, miosis; cardiac irreg; muscle fasciculation; dyspnea (breathing difficulty)

The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. This substance may be hazardous to the environment. Special attention should be given to fish and wildlife. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.

...Workers /should/ undergo an annual medical exam... . Contraindications for work with organophosporous pesticides are organic diseases of the CNS, mental disorders and epilepsy, pronounced endocrine disorders... . Blood cholinesterase /SRP: both plasma and RBC/ must be determined before work starts. In the event of prolonged work periods, this activity should be determined at intervals of 3-4 days. Persons exhibiting a fall in choinesterase activity of 25% or more must be transferred to other work where they are not exposed... until /cholinesterase activity/ is... restored. /Organophosphorous pesticides/

Measurement of whole blood-AChE is the most widely adopted method for monitoring the effects of occupational exposure to organophosphorus insecticides. Physiological variations in blood ChE levels occur in a healthy person and are seen among a population. It has been estimated that the coefficient of variation for AChE activity in samples from an individual is 8-11%, and that a decrease of 23% below pre-exposure level may, therefore, be considered significant. If the average of several pre-exposure values were available, then a decrease of 17% would be significant. It has been recommended that, if measured activity is reduced by 30% or more of the pre-exposure value, AChE measurements should be repeated at appropriate intervals to confirm the results. Depressions of AChE or ChE in excess of 20-25% are considered diagnostic of exposure but not, necessarily, indicative of hazard. Depressions of 30-50% or more are considered indicators for removal of an exposed individual from further contact with pesticides until levels return to normal. /Organophosphorus Pesticides/

...Organophosphorus pesticides may undergo hydrolysis in vivo to yield substituted phosphoric acids that are subsequently excreted in urine. Advances in gas chromatography and combined gas chromatography/mass spectrometry (GC/MS) have made it possible to analyse the urine of exposed persons for the presence of appropriate metabolites. It is usually necessary to preserve the sample by the addition of chloroform, to concentrate or extract the metabolite(s), and to convert them to suitably-volatile derivatives that can be detected by GC. Obviously, access to a well-equipped analytical laboratory, capable of the quick processing of samples, is a necessary factor if monitoring by urine analysis is proposed. However, in some cases, simpler and sensitive colorimetric tests are available for screening the urine of exposed persons. Thus, 4-nitrophenol can be measured directly in the urine of workers exposed to parathion. Consideration of the concentration of metabolite(s) in the urine can be helpful in determining patterns of exposure, and these concentrations can be calibrated against the effects on AChE for a particular pesticide. However, the time-course and peak of excretion of metabolites appears to vary according to dose, so that serial sampling and analyses of urine are desirable. Levels of metabolite alone cannot be considered a guide to hazard. This is obvious when it is realized that pesticides that have very different toxicities may yield identical acidic metabolites. Thus, the level of metabolites in urine, after exposure to sufficient amounts of the very toxic parathion-methyl to depress blood-AChE to 50%, will be much lower than that of the identical metabolites, following exposure to the related fenitrothion, which is about 40 times less toxic. /Organophosphorus 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. Sulprofos is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0076; Pesticide type: insecticide; Registration Standard Date: 08/07/1981; Case Status: The last registered pesticide products containing this pesticide were voluntarily cancelled by their registrants while EPA was developing the RED; Active ingredient (AI): sulprofos; Data Call-in (DCI) Date(s): 08/20/1990, 06/28/1991, 10/13/1995; AI Status: The active ingredient is no longer contained in any registered products ... "cancelled.".

The characteristic pharmacological effects of the anti-ChE agents are due primarily to the prevention of hydrolysis of ACh by AChE at sites of cholinergic transmission. Transmitter thus accumulates, and the response to ACh that is liberated by cholinergic impulses or that is spontaneously released from the nerve ending is enhanced. With most of the organophosphorus agents ... virtually all the acute effects of moderate doses are attributable to this action. /Anticholinesterase agents/

The cardiovascular actions of anticholinesterase agents are complex, since they reflect both ganglionic and postganglionic effects of accumulated ACh on the heart and blood vessels. The predominant effect on the heart from the peripheral action of accumulated ACh is bradycardia, resulting in a fall in cardiac output. Higher doses usually cause a fall in blood pressure, often as a consequence of effects of anticholinesterase agents on the medullary vasomotor centers of the CNS. /Anticholinesterase agents/

After absorption, sulprofos was metabolized rapidly and excreted primarily in the urine. The metabolism involved oxidation of the methylthio sulfur to sulfoxide and sulfone derivates and hydrolysis of the phosphorus O-phenyl ester to phenolic metabolites (rat, cow).

Sulprofos is involved in a series of oxidation reactions that may result in replacing the thiono sulfur with oxygen and/or the addition of first one and then two oxygen atoms to the thioether sulfur. The phosphorus-O-phenyl ester of sulprofos and any of these materials may be hydrolyzed to the free phenols, which are then conjugated and eliminated, usually in the urine. The oxidation of the thioether sulfur to its sulfoxide is catalyzed by microsomal flavin-contain monooxygenase. The major sulprofos metabolites are phenol, phenol sulfoxide, phenol sulfone, and their conjugates. Sulprofos sulfoxide, sulprofos sulfone, O-analog and O-analog sulfone were also identified in pigs, goats and cows but not in the rat or hen.

...Metabolism of this insecticide by the cow involved oxidation of the methylthio sulfur to sulfoxide and sulfone derivatives and hydrolysis of the phosphorus O-phenyl ester to give phenolic metabolites that were excreted primarily in the urine in conjugated form. The low residues secreted into milk were also primarily conjugated phenols.

Sulprofos is rapidly and nearly completely absorbed following oral exposure. In rats, more than 98% of an oral dose of sulprofos was eliminated within 48-72 hr after dosing. Rats that received one 11 mg/kg dose or ten 10 mg/kg doses of sulprofos during 15 days also excreted >96% of the dose (or last dose) within 24 hr. The primary route of excretion was through the urine, and <11% was excreted in the feces. ...Tissues and organs retained </=2% of the dose; the highest residues were in the fat, ovaries, skin, and liver. Less than 1% of the dose was expired as CO2 or volatile organic compounds from any exposure. A previous study had demonstrated that female Sprague-Dawley rats dosed at 10 mg/kg excreted >92% within 24 hr.

Pigs rapidly excreted an oral dose of sulprofos. More than 95% of the dose was excreted in urine by 24 hours. ...Maximum blood levels occurred 4 hours posttreatment, at which time tissue levels were <0.01 ppm, except for 0.27- and 0.53-ppm levels in liver and kidney, respectively. Traces of sulprofos and its sulfoxide were found in the omental fat. All tissue residues were <0.05 ppm of sulprofos equivalents at 48 hours posttreatment.

A lactating Jersey cow was treated orally with the insecticide O-ethyl O-(4-(methylthio)phenyl-14-C) S-propyl phosphorodithioate (BAY NTN 9306) at 0.12 mg/kg as a single oral dose. The administered radiocarbon was essentially quantiatively excreted during a 6-day post-treatment period; about 90% of the dose appeared in urine, about 0.1% in milk and the rest in feces. Ten days after the 1st treatment, the animal was treated again with the radiochemical at 0.62 mg/kg. Twelve hours later, when radiocarbon residues in the blood were maximal, the cow was sacrificed, and tissue and digestive tract content samples were analyzed for metabolites.

Used to control insects on alfalfa, cotton, corn, peanuts, tobacco, and tomatoes; effective against beet armyworm; [ACGIH]

Farming (Pesticides) [Category: Industry]

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

For sulprofos (USEPA/OPP Pesticide Code: 111501) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Non-systemic insecticide with contacty and stomach action. Cholinesterase inhibitor. Used in the control of Lepidoptera, Thysanoptera, Heliothis spp., and other insects in cotton, soya beans, tobacco, vegetables, and tomatoes. /Former use/

200,000 pounds in 1989, 794,000 pounds in 1982

For 1989-1991, 894,000 lbs of sulprofos were applied to cotton crops annually in 11 states. Heaviest usage was in Mississippi followed by Texas.

In 1992, 637,000 acres of cotton crops were treated with 852,000 lbs of sulprofos in 11 states. Heaviest usage was in Mississippi followed by Texas and Louisiana.

Emulsifiable concentrate; Ultra-low volume liquid

Trade names: Bolstar; Helothion

During the reregistration process, EPA approved the registrants' request for voluntary cancellation of sulprofos registrations (61 FR 65218, December 11, 1996) (FRL-5573-6). No active registrations exist for sulprofos.

Sulprofos is a selective organophosphate used to control foliar lepidopterous, dipterous and hemipterous insects. ... It is particularly efficacious in beet and armyworm control. /Former use/