テメホス

Temephos

HCID 5392CAS 3383-96-8

基本情報

標準SMILES
COP(=S)(OC)Oc1ccc(Sc2ccc(OP(=S)(OC)OC)cc2)cc1
InChIKey
WWJZWCUNLNYYAU-UHFFFAOYSA-N
分子式
C16H20O6P2S3
平均分子量
466.5 g/mol
単同位体質量
465.98972462

概要

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

名称と識別子

優先名称
Temephos
IUPAC
[4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-dimethoxy-sulfanylidene-λ5-phosphane
現地名
テメホス
英語名
Temephos
分子式
C16H20O6P2S3
分子量
466.47

名称と別名

temephosTemefos3383-96-8ABATEDifosDifenphosAbathionBiothionProcidaNephisBithionNephis 1G
名称をさらに表示
O,O,O',O'-テトラメチル-O,O'-チオジ-p-フェニレンホスホロチオエートネフィステメホスネフィス1Gビチオン4,4'-チオビスフェノールビス(チオりん酸O,O-ジメチル)(チオジ-4,1-フェニレンビスオキシ)ビスホスホノチオ酸O,O,O',O'-テトラメチルプロシダ実験殺虫剤52160アバチオンジフェンホス[チオジ(1,4-フェニレンオキシ)]ビス(チオホスホン酸)O,O,O',O'-テトラメチルエコプロ-1707ビオチオンアバートジホス(殺虫剤)テメホス標準品O,O,O',O'-テトラメチル-O,O'-チオジ-p-フェニレンホスチオジ(p-フェニレン)-ジオキシ-ビス(チオホスホン酸)O,O,O’,O’-テトラメチルチオジ(パラ-フェニレン)-ジオキシ-ビス(チオホスホン酸) O,O,O',O'-テトラメチル (別名テメホス)AbatEcoprooms786swebatcl52160
NimitexNimitoxSwebateEcopro 1707LyporDiphos (pesticide)TetrafenphosAbaphos

データベース識別子

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

物性

構造計算による物性

XLogP
6
極性表面積
145 Ų
水素結合供与体数
0
水素結合受容体数
9
回転可能結合数
10
重原子数
27

実験および物理化学的性質

SpringerMaterials PropertiesFusion temperature
Pesticides · 5 件

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Pesticide (Temephos) -> USDA PDB

Pesticide

LogP · 2 件

log Kow = 5.96

5.96

Density · 5 件

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 件

Colorless crystals

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

Solubility · 6 件

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

物理化学的性質

融点
30 · 30-31°C
沸点
518.5 · 518.5±60.0 °C(Predicted)
比重(密度)
1.32 · 1.3200
蒸気圧
9.5 · 9.5×10-6Pa (20-25 °C)
貯蔵温度
2 · 2-8°C
溶解性
100 mg/mL · DMSO : ≥ 100 mg/mL (214.38 mM)

安全と法規制

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Regulatory Information · 4 件

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 件

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:

安全と保護具

Fire Fighting · 2 件

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 件

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 件

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 件

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 件

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

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

毒性情報

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 件

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 件

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

法規制情報

FIFRA Requirements · 2 件

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.

安全データ

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

化学と産業

薬理情報

Mechanism of Action · 2 件

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 件

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 件

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.

用途と製造

Uses · 6 件

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 件

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 件

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
応用分野 · 4 件

用途農薬?殺虫剤

説明Abate 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).

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

一般的な説明White crystalline solid or liquid. Boiling point 87°F. Used as an insecticide. Technical grade is a viscous brown liquid.

上流・下流製品情報

サプライヤー50 社

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
盐城通铭生物科技有限公司15195160625 · [email protected]
上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]

関連反応

2 件

関連ノート

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