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4-トリチルモルホリン

Trifenmorph

HCID 14993
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1420-06-0
標準SMILES
c1ccc(C(c2ccccc2)(c2ccccc2)N2CCOCC2)cc1
InChIKey
ZJMLMBICUVVJDX-UHFFFAOYSA-N
分子式
C23H23NO
平均分子量
329.4 g/mol
単同位体質量
329.17796436

概要

Trifenmorph is a member of morpholines.

名称と識別子

優先名称
Trifenmorph
IUPAC
4-tritylmorpholine
現地名
4-トリチルモルホリン
英語名
TRIFENMORPH
分子式
C23H23NO
分子量
329.43

名称と別名

Trifenmorph4-TritylmorpholineTriphenmorphe4-(Triphenylmethyl)morpholine1420-06-0N-TritylmorpholineFRESCONMorpholine, 4-trityl-Shell WL 8008Morpholine, N-trityl-Morpholine, 4-(triphenylmethyl)-N-(Triphenyl-methyl)morpholine
名称をさらに表示
4-トリチルモルホリントリフェンモルフトリチルモルホリン4-(トリフェニルメチル)モルホリンフレスコンN-トリチルモルホリントリフェンモルフ標準品トリフェンモルフ STANDARDトリフェンモルフ Standard, 100 µg/mL in MeOHWL-8008shellwl8008TREFENMORPHTRIPHENMORPHTriphenomorphn-trityl-morpholin
H1IL51K9CWDTXSID6042492RefChem:191559DTXCID4022492215-812-2WL 8008Caswell No. 898ATrifenmorph [ISO:BSI]

データベース識別子

CAS
1420-06-0
PubChem CID
14993
DTXSID
DTXSID6042492

物性

構造計算による物性

XLogP
4.6
極性表面積
12.5 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
4
重原子数
25
形式電荷
0
複雑度
339

実験および物理化学的性質

Pesticides · 3 件

Molluscicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Molluscicides

Color/Form · 2 件

Crystals from ethanol

Colorless crystalline solid

Solubility · 2 件

In water, 2.0X10-2 mg/L at 20 °C

At 20 °C (g/L): carbon tetrachloride 300; chloroform 450; tetrachloroethylene 255

CorrosivityNon-corrosive
Melting Point · 2 件

176 °C

MP: 176-178 °C, resolidifying and remelting at 185-187 °C; (technical melts 150-170 °C, and again at 170-185 °C)

Vapor Pressure0.00000003 [mmHg]
Physical DescriptionColorless solid; Technical product is light brown solid; [HSDB]
Stability/Shelf LifeIT IS STABLE TO HEAT & ALKALIES, BUT IS HYDROLYZED BY MILD ACID CONDITIONS TO MORPHOLINE & TRIPHENYLMETHANOL. SLIGHT DECOMPOSITION OCCURS IN UV LIGHT.
Other Experimental Properties · 2 件

Stable to heat and alkali but hydrolyzed by mild acidic conditions to morpholine and triphenylmethanol

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

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

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

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

危険有害性情報

Regulatory Information2002/2076
Hazards Summary · 1 件

In high-dose animal studies, causes somnolence and changes to liver; [RTECS] Highly selective snail neurotoxin; Also hazardous to some fish and slightly toxic to vertebrates; Toxic by ingestion or skin absorption; Oral LD50 (rat) = 100-200 mg/kg in chlorinated solvents and 1200-1600 mg/kg in other organic solvents; Dermal LD50 (rat) = 1000 mg/kg; Readily metabolized and excreted in mammals; [INCHEM PDS: Triphenmorph]

Hazard Classes and Categories · 2 件

Acute toxicity - category 4

Acute Tox. 4 *

安全と保護具

Disposal Methods · 2 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Residues in containers should be emptied in a diluted form into a deep pit taking care to avoid ground waters. The empty container may be decontaminated by rinsing two or three times with water and detergent and scrubbing the sides. The hands should be protected during this work. Decontaminated containers should not be used for any other purpose.

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

Rats and dogs were given (14)C labeled frescon as single oral doses. Frescon rapidly hydrolyzed to triphenylcarbinol and morpholine in the stomach. Morpholine was rapidly absorbed and excreted largely unchanged though some was degraded. Triphenylcarbinol was absorbed slowly and oxidized to p-hydroxyphenyldiphenylcarbinol. Triphenylcarbinol and its p-hydroxy analog were found in urine, bile and feces, both free and conjugated with glucuronic acid. Traces of ortho- and meta-hydroxyphenyldiphenylcarbinol were detected both free and conjugated. There appeared to be three glucuronide fractions, possibly diglucuronides of hydroxytriphenylcarbinols, carbinol-group derived glucuronides and phenolic-group derived glucuronides.

Fish (S. mossambicus) were exposed to frescon for 22 hr. Analyses of fish indicated the presence of unchanged frescon and a small amount of morpholine. Similar results were observed when bile was analyzed.

Absorption, Distribution and Excretion · 1 件

In dogs, rats and mice /trifenmorph/ was rapidly metabolized by gastrointestinal enzymes to triphenylcarbinol, and morpholine. Triphenylcarbinol was absorbed slowly and it was oxidized by hepatic systems to para-hydroxyphenyldiphenylcarbinol and also, ortho- and meta-hydroxytriphenylcarbinols to a lesser extent. Morpholine was rapidly absorbed and excreted in the urine unchanged as a glucuronic acid conjugate. Triphenylcarbinol and its hydroxy derivatives were found in urine and feces as free compounds and in three glucuronide fractions; diglucuronides, carbinol-group glucuronide and phenolic-groups glucuronides. In (14)C-labelled tracer dose studies no (14)CO2 was respired and, after 96 hours only 3% of the radioactivity remained in the carcass.

用途と製造

Uses · 5 件

Used as molluscicide to kill aquatic and semi-aquatic snails carrying parasites; [HSDB]

For trifenmorph (USEPA/OPP Pesticide Code: 498300) 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./

Molluscicide /Former US/

関連反応

1 件
反応記録を作成
HRID 80304 の反応式
HRID 80304生成物としてuspto-grants-2014_09

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
ChEMBL
CHEMBL2086832
ChEBI
CHEBI:82264
UNII
H1IL51K9CW
EC Number
215-812-2
Nikkaji
J7.484E

Light brown crystals, 90-95% pure /Technical grade/

物理化学的性質

融点
174 · 174-176°, resolidifies and melts again at 185-187°
沸点
467.03 °C · 467.03°C (rough estimate)
比重(密度)
1.0859 · 1.0859 (rough estimate)
屈折率
1.5614 · 1.5614 (estimate)
酸解離定数(Pka)
4.58 · 4.58±0.10(Predicted)
水溶解度
20 ug/L · 20ug/L(20℃)
Henry's Law Constant
7.6 · 7.6×104 mol/(m3Pa) at 25℃, HSDB (2015)
EPAの化学物質情報
Trifenmorph (1420-06-0)
Preventive Measures · 3 件

Mixing, if not mechanical, should always be carried out with a paddle of appropriate length. Avoid contact with mouth and eyes. Before eating, drinking or smoking, hands and other exposed skin should be thoroughly washed with alkaline soap.

Keep /technical trifenmorph/ away from foodstuffs and animal feeds.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Personal Protective Equipment (PPE) · 2 件

When opening a container and when mixing, protective impermeable boots, clean overalls, impermeable gloves and a respirator should be worn.

Closed systems and forced ventilation may be required to reduce, as much as possible, the exposure of workers to the chemical.

毒性情報

Ecotoxicity Values · 5 件

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout) yearling; Concentration: 0.1 mg/L for 96 hr, pH 6.9-7.0 /Conditions of bioassay not specified in source examined/ /16.5% emulsifiable concentrate/

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout) yearling; Concentration: 0.52 mg/L for 96 hr, pH 6.9-7.0, hard water /Conditions of bioassay not specified in source examined/ /16.5% Emulsifiable concentrate/

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout) yearling; Concentration: 1.5 mg/L for 96 hr, pH 6.9-7.0, hard water /Conditions of bioassay not specified in source examined/ /50% paste/

LC50; Species: /Oncorhynchus mykiss/ (Rainbow trout) yearling; Concentration: 0.08 mg/L for 96 hr, pH 6.9-7.0 /Conditions of bioassay not specified in source examined/ /50% paste/

For more Ecotoxicity Values (Complete) data for Trifenmorph (17 total), please visit the HSDB record page.

Environmental Fate · 5 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+5(SRC), determined from a structure estimation method(2), indicates that trifenmorph is expected to be immobile in soil(SRC). Volatilization of trifenmorph from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.3X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Trifenmorph is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). In soil within a few weeks, trifenmorph is aerobically converted to triphenyl methanol which undergoes slow hydroxylation(5).

TERRESTRIAL FATE: Half of N-tritylmorpholine applied to soil was lost in 1 to 4 weeks.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3.7X10+5(SRC), determined from a structure estimation method(2), indicates that trifenmorph 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 1.3X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 280(SRC), from an estimated log Kow of 4.21(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Under mild acid conditions, trifenmorph is hydrolyzed to morpholine and triphenylmethanol(3). Biodegradation is not an important environmental fate process in water(SRC) based on the slow rate reported for soil(7).

AQUATIC FATE: The fate of the molluscicide trifenmorph (N-tritylmorpholine) following its use in irrigation systems to control the intermediate hosts of schistosomes was studied by laboratory and field experiments. Laboratory studies with 14C-trifenmorph indicated that bean plants did not take up detectable residues when the soil in which they were grown was irrigated with water containing trifenmorph in concentrations likely to occur in the field. These laboratory studies have been complemented by field irrigation studies of growing crops in southern Africa and the Sudan. Residues of trifenmorph and its breakdown product triphenylmethanol could not be detected in the crops and the limit of detectability was 0.01-0.02 ppm. These results indicate that residues are not likely to be present in irrigated crops following the treatment of the irrigation water systems with trifenmorph(1).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trifenmorph, which has an estimated vapor pressure of 2.8X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase trifenmorph 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 2.5 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trifenmorph may be removed from the air by wet or dry deposition(SRC). Slight decomposition occurs in UV light(4).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Ecotoxicity Excerpts · 4 件

/AQUATIC SPECIES/ Fish were killed in canals treated for 6 hr with frescon to yield concentration of 0.1 ppm.

/AQUATIC SPECIES/ ... Aquatic micro-flora and -fauna were uneffected at 0.2 ppm.

/AQUATIC SPECIES/ /Trifenmorph/ above 0.03 ppm /may be/ harmful to fish.

/OTHER TOXICITY INFORMATION/ /N-tritylmorpholine/ is highly specific, being harmless to plants, insects, and most vertebrates, though it is moderately toxic to some species of fish.

Soil Adsorption/Mobility · 2 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trifenmorph can be estimated to be 3.7X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that trifenmorph is expected to be immobile in soil.

KOC = 37,500 (calculated from water solubility by regression equations). /From table/

Artificial Pollution SourcesTrifenmorph's former production may have resulted in its release to the environment through various waste streams; its former use as a molluscicide(1) resulted in its direct release to the environment(SRC).
Environmental BiodegradationAEROBIC: In soil within a few weeks, trifenmorph is aerobically converted to triphenyl methanol which undergoes slow hydroxylation.
Environmental Bioconcentration · 3 件

An estimated BCF of 280 was calculated in fish for trifenmorph(SRC), using an estimated log Kow of 4.21(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Sarotherodon mossambicus /Mozambique talapia/, juvenile, exhibited a bioconcentration factor of 1,300 after 55 hr.

Bioconcentration factor = 5,600 (calculated from water solubility by regression equations). /From table/

Volatilization from Water/Soil · 1 件

The Henry's Law constant for trifenmorph is estimated as 1.3X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that trifenmorph is expected to be essentially nonvolatile from water and moist soil surfaces(2). Trifenmorph is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Non-Human Toxicity Excerpts · 2 件

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The mammalian and avian toxicities of N-tritylmorpholine (Frescon, WL 8008), a compound active against the snails that are the intermediate hosts of schistosomes, are reported. ... Administered percutaneously to rats, N-tritylmorpholine produced no ill-effects at 1000 mg/kg. N-Tritylmorpholine fed in the diets of rats at 100 ppm for 90 days produced no significant effect. ...

/GENOTOXICITY/ Trifenmorph was not mutagenically active in a microbial Ames test.

Environmental Abiotic Degradation · 2 件

The rate constant for the vapor-phase reaction of trifenmorph with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate of hydrolysis of 14C-trifenmorph is dependent on the pH of the water (relatively high at low pH values of <7.0) and concentration of the compound(2). Under mild acidic conditions, trifenmorph is hydrolyzed to morpholine and triphenylmethanol(4). Mud and sediment gradually adsorb trifenmorph and carbinol(3). Slight decomposition occurs in UV light(3).

The rate of hydrolysis of 14C-trifenmorph is dependent on the pH of the water (relatively high at low pH values of <7.0) and concentration of the compound(1).

Probable Routes of Human ExposureOccupational exposure and general population exposure should be low or non-existent since trifenmorph is no longer produced or used in the US. (SRC)

安全データ

毒性
LD50 orally in rats: 1200-2000 mg/kg (Boyce)
hs_code
29349990
risk_code
22-50/53
hazard_code
Xn,N
safety_code
60-61
有毒物質データの
1420-06-0(Hazardous Substances Data)

As molluscicide (against snails which carry bilharzia flukes) /Former use in USA/

Effective against aquatic and semi-aquatic snails. Recommended for application to irrigation and other moving water systems ... and in static water ... . Also recommmended for application to Lymnaea truncatula /dwarf pond snail; also known as Galba truncatula/ habitats ... to control fascioliasis. /Former use in USA/

Impurities... Tar impurities: 20 g/kg; volatile matter: 100 g/kg.
Methods of ManufacturingAdams et al, US Patent 3,577,413 (1971 to Shell).
Formulations/Preparations · 4 件

Trade Names: Frescon, WL 8008, Trifenmorph.

Emulsifiable concentrate.

Frescon Paste: active ingredient 50% N-tritylmorpholine.

FRESCON: (PRODUCT DISCONTINUED BY SHELL INTERNATIONAL CHEMICAL, LONDON)

General Manufacturing Information · 1 件

World Health Organization has specified the chemical and physical requirements for technical trifenmorph WHO/SMT/5, 4-(triphenylmethyl)morpholine content: 900.0 g/kg; acidity: calculated as H2SO4 1 g/kg; water content: 1 g/kg; tar impurities: 20 g/kg; volatile matter: 100 g/kg.

応用分野

使用As molluscicide (against snails carrying bilharzia flukes).

上流・下流製品情報

上流原料

4-(ジメチルアミノ)-1-(トリフェニルメチル)ピリジニウムクロリドトリチルクロリドベンゾフェノントリフェニルメタノールブロモベンゼンモルホリン

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