Temephos

HCID 5392CAS 3383-96-8

Grundinformationen

Standard-SMILES
COP(=S)(OC)Oc1ccc(Sc2ccc(OP(=S)(OC)OC)cc2)cc1
InChIKey
WWJZWCUNLNYYAU-UHFFFAOYSA-N
Summenformel
C16H20O6P2S3
Durchschnittliche Molmasse
466,5 g/mol
Monoisotopische Masse
465,98972462

Überblick

Temephos appears as white crystalline solid or liquid (above 87 °F). Used as an insecticide. Technical grade is a viscous brown liquid. (NIOSH, 2024)

Namen und Bezeichner

Bevorzugter Name
Temephos
IUPAC
[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-dimethoxy-sulfanylidene-λ5-phosphane
Lokaler Name
Temephos
Englischer Name
Temephos
Summenformel
C16H20O6P2S3
Molmasse
466.47

Namen und Synonyme

temephosTemefos3383-96-8ABATEDifosDifenphosAbathionBiothionProcidaNephisBithionNephis 1G
Weitere Namen anzeigen
AbatEcoprooms786swebatcl52160
NimitexNimitoxSwebateEcopro 1707LyporDiphos (pesticide)TetrafenphosAbaphos

Datenbank-Bezeichner

CAS
3383-96-8
PubChem CID
5392
DTXSID
DTXSID1032484
ChEMBL
CHEMBL1355821
ChEBI
CHEBI:38954
UNII
ONP3ME32DL
EC Number
222-191-1
Nikkaji
J4.517I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6
Polarare Oberfläche (TPSA)
145 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
9
Frei drehbare Bindungen
10
Schwere Atome
27

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesFusion temperature
Pesticides · 5 Einträge

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Temephos) -> USDA PDB

Pesticide

LogP · 2 Einträge

log Kow = 5.96

5.96

Density · 5 Einträge

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

1.3 g/cu cm

1.3 g/cm³

1.32

1.32

Color/Form · 2 Einträge

Colorless crystals

White, crystalline solid or liquid (above 87 degrees F) [Note: Technical grade is a brown, viscous liquid].

Solubility · 6 Einträge

Insoluble (NIOSH, 2024)

Soluble in common organic solvents such as diethyl ether, aromatic and chlorinated hydrocarbons.

Soluble in acetonitrile, carbon tetrachloride, ether, toluene

In hexane, 9.6 g/L

In water, 9.0X10-6 g/L at 10 °C; 2.7X10-4 g/L at 20 °C; 7.0X10-4 g/L at 30 °C

In water, 0.27 mg/L at 25 °C

Physikochemische Eigenschaften

Schmelzpunkt
30 · 30-31°C
Siedepunkt
518.5 · 518.5±60.0 °C(Predicted)
Dichte
1.32 · 1.3200
Dampfdruck
9.5 · 9.5×10-6Pa (20-25 °C)
storage temp.
2 · 2-8°C
Löslichkeit
100 mg/mL · DMSO : ≥ 100 mg/mL (214.38 mM)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H302 (61.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P319, P321, P330, P361+P364, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 78 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H311: Toxic in contact with skin [Danger Acute toxicity, dermal]

Gefahrenhinweise

Regulatory Information · 4 Einträge

Hazard Traits - Developmental Toxicity; Neurotoxicity

2002/2076

Temephos: HSNO Approval: HSR002880 Approved with controls

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.)

Other Safety InformationIMAP assessments - Phosphorothioic acid, O,O'-(thiodi-4,1-phenylene) O,O,O',O'-tetramethyl ester: Environment tier I assessment
DOT LabelClass 9
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

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

Fire PotentialCombustible. Liquid formulations containing organic solvents may be flammable.
Health HazardsExcerpt from NIOSH Pocket Guide for Temephos:

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

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

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 2 Einträge

Excerpt from NIOSH Pocket Guide for Temephos:

(General first aid procedures)

Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store in an area without drain or sewer access.
Exposure Control and Personal Protection · 1 Eintrag

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]

Fire Fighting Procedures · 2 Einträge

Water, foam, carbon dioxide, dry chemical. /Malathion/

Extinguish fire using agent suitable for type of surrounding fire. /Malathion/

Toxikologische Informationen

InteractionsMixture of abate and malathion are appreciably more toxic in rats than either compound alone.
Target OrgansEyes, respiratory system, central nervous system, cardiovascular system, blood cholinesterase
Ecotoxicity Values · 5 Einträge

LD50; Species: Anas platyrhynchos (Mallard duck, male, age 4-7 months) oral 79.4 mg/kg (95% confidence limit 38.5-163 mg/kg) /sample purity 92%/

LD50; Species: Anas platyrhynchos (Mallard duck, female, age 2-4 months) oral 31.5 ppm (95% confidence limit: 18.1-54.9 ppm)

LD50; Species: Anas platyrhynchos (Mallard duck, egg) egg immersion 107 ug/g egg for 30 sec (in oil vehicle) /from table/

LC50; Species: Anas platyrhychos (Mallard duck, age 17 days) dietary 894 ppm for 5 days (95% confidence limit 575-1910 ppm) /Technical 86.8%/

For more Ecotoxicity Values (Complete) data for TEMEPHOS (81 total), please visit the HSDB record page.

Environmental Fate · 5 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 18,250 to 31,800(2) indicate that temephos is expected to be immobile in soil(SRC). Volatilization of temephos from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Temephos is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.9X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). A biodegradation half-life of 17.2 days under aquatic conditions(2) suggests that biodegradation may be a moderately important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 18,250 to 31,800(2) indicate that temephos is expected to adsorb to suspended solids and sediment(SRC). Temephos has been reported to rapidly partition to sediment and suspended organic matter and become strongly adsorbed(3,4). Volatilization from water surfaces is not expected(5) based upon an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). According to a classification scheme(7), a BCF of 2,300(2) suggests bioconcentration in aquatic organisms is very high(SRC). A biodegradation half-life in water of 17.2 days under aerobic conditions(2) suggests that biodegradaton may be an important environmental fate process in water(SRC).

AQUATIC FATE: Temephos was added to pond water in beakers to give an initial concentration of 0.1 ppm. The dissipation was measured at temperatures of 10, 25 and 38 °C. Within 48 hours, the concentration of temephos in the pond water reached a steady state of 0.02-0.04 ppm with no significant difference observed for the three temperatures. The majority of temephos was found associated with organic matter in the pond water. Hydrolysis and oxidation may account for some of the dissipation; however, most of the temephos was adsorbed to organic matter and slowly released to achieve the steady state(1).

AQUATIC FATE: The time for 90% disappearance of temephos applied at 10 ppb to the surface of artificial polyethylene-lined ponds and activated by leaf litter (sediment) was 1.05 days. Ten days were required for a decline of temephos concentration to 0.01 ppb. Adsorption by polyethylene played a significant role in temephos disappearance, with a maximum of 1560 ppb adsorbed in <1 day. The rapid adsorption corresponded to rapid partitioning. This was followed by desorption from polyethylene, such that small amounts of insecticide were rereleased into the aqueous phase and, after a time, equilibrium was reached. The behavior of insecticides in artificial ponds may not completely reflect the behavior in natural systems(1).

For more Environmental Fate (Complete) data for TEMEPHOS (6 total), please visit the HSDB record page.

Food Survey ValuesThe concentration of temephos in California rice grain and foliage, date not provided, ranged from 0.01-0.07 and <0.01 ppm, respectively(1).
Adverse EffectsOther Poison - Organophosphate

Regulatorische Informationen

FIFRA Requirements · 2 Einträge

The Agency has previously identified and required the submission of the generic (i.e., active ingredient specific) data necessary to support reregistration of products containing temephos active ingredients. The Agency has completed its assessment of the human health and ecological risks associated with the use of pesticides containing the active ingredient temephos of organophosphates as a class. Based on a review of these data and public comments on the Agency's assessments for the active ingredient temephos, EPA has sufficient information on the human health and ecological effects of temephos to make a reregistration eligibility decision. Because temephos has no dietary or residential exposure concerns, it is not subject to further cumulative assessment for other organophosphates. This ... /Reregistration Eligibility Decision document/ identifies risk reduction measures that are necessary to allow the continued use of temephos. Appendix B. identifies the generic data requirements that the Agency reviewed as part of its determination, and lists the submitted studies that the Agency found acceptable. Based on its current evaluation of temephos alone, the Agency has determined that temephos products, unless amended and used as specified in this document, would present risks inconsistent with FIFRA. Accordingly, should the registrant fail to implement any of the risk mitigation measures identified in this /Reregistration Eligibility Decision/ document, the Agency may take regulatory action to address the risk concerns from use of temephos. For temephos, if all changes outlined in this document are incorporated into the labels, then the risks associated with current use patterns will be mitigated.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Temephos is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0006; Pesticide type: insecticide; Registration Standard Date: 8/1/81; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): temephos; Data Call-in (DCI) Date(s): 11/21/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.

Sicherheitsdaten

OEB
B
OEL
TWA: 10 mg/m3 (total)
wgk
3
tsca
TSCA listed
ridadr
UN 3077
RTECS-Nr.
TF6890000

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 2 Einträge

Abate is a cholinesterase inhibiting insecticide.

Organophosphates poison insects and humans primarily by phosphorylation of the acetylcholinesterase enzyme at nerve endings. /Organophosphate Cholinesterase-inhibiting pesticides/

Biological Half-LifeWhen (3)H temephos was administered to rats by mouth, radioactivity reached a peak in blood between 5 & 8 hr & then dissipated with half-life of about 10 hr.
Metabolism/Metabolites · 5 Einträge

Studies with tritium-labeled abate indicated that this insecticide was relatively resistant to metabolic degradation. Residues on bean leaves ... consisted primarily of intact abate- about 70% of applied dose. The major metabolite was the sulfoxide derivative- less than 5% of the dose. Traces of sulfone derivative, oxygen analog, and glucosidic conjugates of phenolic hydrolysis products from abate and its sulfoxide & sulfone derivatives were also observed.

When rats were fed Abate, 60% of the material appeared in ... feces as the oxygen analog of Abate and its sulfoxide. The thiodiphenol, sulfinyldiphenol and sulfonyldiphenol were also found. In the urine, sulfate and glucoside conjugates of the hydrolysis products of Abate and sulfoxide as well as sulfone analogs accounted for 39.5% of the material administered. ... Five compounds found in feces and three in urine were not identified.

Larvae of the mosquito (Aedes aegypti L) metabolized Abate to sulfoxides and sulfones of Abate, the oxygen analog, and the demethylated analog. Some conjugates were also formed. In the housefuly, all expected metabolic products were found internally either as the intact ester or as hydrolyzed material ...

Abate yields in rat, abate sulfoxide and thiodiphenol. /From table/

For more Metabolism/Metabolites (Complete) data for TEMEPHOS (8 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationPesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Absorption, Distribution and Excretion · 4 Einträge

Dermal penetration of (14)C-labeled abate was measured in rats, rabbits, and dogs. Absorption was assessed by monitoring excreted radioactivity in urine and feces for 7 days and analysis of tissue specimens /were conducted/. Absorption would be expected to be less than 3% of applied dose. No evidence of bodily retention or pooling of radioactive moiety was demonstrated.

In guinea pig, /oral/ absorption apparently was less than in rat, & biliary excretion of metabolites was demonstrated.

When (3)H temephos was administered to rats by mouth, radioactivity reached a peak in the blood between 5 and 8 hr and then dissipated within a half-life of about 10 hr. Appreciable radioactivity was found only in the GI tract and fat. Both in the feces and in the fat, most of the radioactivity came from unchanged insecticide, but small amounts of the sulfoxide were present also. Traces of temephos were found in the urine ... .

In mammals, elimination of mainly of unchanged temephos in the feces and urine.

Verwendung und Herstellung

Uses · 6 Einträge

Used to kill mosquito, midge, and black fly larvae in lakes, ponds, and wetlands; also used to kill fleas and human lice; [EXTOXNET]

Farming (Pesticides) [Category: Industry]

For temephos (USEPA/OPP Pesticide Code: 059001) ACTIVE products with label matches. /SRP: Registered for 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./

Larvicide for mosquitoes, black flies, and midges and in other applications.

Effective in controlling fleas on dogs and cats and lice on humans. On crops, it is effective in controlling cutworms, thrips on citrus, and lygus bugs.

Control of "river blindness" (onchoceraiasis) ... by killing the insect vector (black fly) carrying filaria of this disease.

U.S. Production(1974) Negligible (consumption)
Consumption Patterns38% as a larvicide on agricultural crops; 62% as a larvicide in other applications. (1971)
Methods of Manufacturing · 2 Einträge

Reaction of 4,4'-thiodiphenol and o,o-dimethyl phosphorochloridothioate

Preparation: J. B. Lovell, R. W. Baer, BE 648531 C.C. 63, 11433e (1965); eidem, US 3317636 (1964, 1967 both to American Cyanamid).

Formulations/Preparations · 5 Einträge

Granular and emulsifiable concentrate.

4 lb/gal EC; also 500 g/l (4.15 lb/gal); 50% water-dispersible powder (wdp); 1 sg insecticide (high density, sandcore granules ... For control of mosquito larvae in dense vegetation); 2g insecticide, 5g insecticide (low density granules for aquatic insect control in open waters and along shores).

Abate 4-E should be extended only with water or aromatic solvents containing at least 85 aromatics (such as Panasol AN-2 and Han 132). Granules 1, 2 & 5% AI. Granules 1%, 2%, 500 E EC, 50% WP.

Temephos is available as 10, 43, and 50% emulsifiable concentrates; 50% wettable powder; and 1, 2, and 5% granules.

For more Formulations/Preparations (Complete) data for TEMEPHOS (26 total), please visit the HSDB record page.

Use ClassificationINSECTICIDES
Anwendungen · 2 Einträge

BeschreibungAbate is the trade name for Temephos, the known organophosphate larvicide. Abate is used to treat water infested with disease-carrying fleas and control mosquito, midge, and black fly larvae. Abate quickly controls mosquito and other insect populations because it kills insect larvae before they mature, and the residual activity of abate prevents insect populations. On decomposition, abate produces oxides of carbon, phosphorous, and sulphur. Exposures to abate in workplaces cause adverse health effects (refer to Temephos for details).

VerwendenTemephos is an organophosphate larvicide used to treat water infested with disease-carrying insects.

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