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N-(1,3-ジチオラン-2-イリデン)アミドりん酸ジエチル

Phosfolan

HCID 13689
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
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基本情報

CAS
947-02-4
標準SMILES
CCOP(=O)(N=C1SCCS1)OCC
InChIKey
ILBONRFSLATCRE-UHFFFAOYSA-N
分子式
C7H14NO3PS2
平均分子量
255.3 g/mol
単同位体質量
255.01527265

概要

Phosfolan is a colorless to yellow solid. Used as an insecticide. (EPA, 1998)

名称と識別子

優先名称
Phosfolan
IUPAC
N-diethoxyphosphoryl-1,3-dithiolan-2-imine
現地名
N-(1,3-ジチオラン-2-イリデン)アミドりん酸ジエチル
英語名
PHOSFOLAN
分子式
C7H14NO3PS2
分子量
255.29

名称と別名

Phosfolan947-02-4PhospholanCYOLANECyolane insecticideAmerican cyanamid 47031American cyanamide 47031American cyanamid CL-47031American cyanamid AC 47,031OMS 646CyalaneCyolan
名称をさらに表示
シオランN-(1,3-ジチオラン-2-イリデン)アミドりん酸ジエチルN-(1,3-ジチオラン-2-イリデン)ホスホルアミド酸ジエチルホスホラン(ジエトキシホスフィニル)ジチオイミド炭酸サイクリックエチレンエステルホスホラン標準品ホスホラン STANDARDホスホラン Standard, 1000 µg/mL in Acetoneホスホラン Standard, 1000 µg/mL in MeOHN-(ジエトキシホスホリル)-1,3-ジチオラン-2-イミンoms646ac47031Cayolancl47031ei47031
ENT 25,830DTXSID1042285AC 47031CL 47031EI 470312-(Diethoxyphosphinylimino)-1,3-dithiolaneCHJ98J84AYDiethyl 1,3-dithiolan-2-ylidenephosphoramidate

データベース識別子

CAS
947-02-4

物性

構造計算による物性

XLogP
0.6
極性表面積
98.5 Ų
水素結合供与体数
0
水素結合受容体数
6
回転可能結合数
5
重原子数
14
形式電荷
0
複雑度
241

実験および物理化学的性質

PesticidesPesticides -> Organophosphate Insecticides
Color/FormSOLID
Solubility · 3 件

SOL IN CYCLOHEXANONE

SOL IN WATER, ACETONE, BENZENE, ETHANOL, CYCLOHEXANE, TOLUENE; SLIGHTLY SOL IN ETHER; SPARINGLY SOL IN HEXANE

Water solubility 650,000 mg/L at 25 deg

Boiling Point · 2 件

239 to 244.4 °F at 0.001 mmHg (EPA, 1998)

410 °C @760 [mm Hg]

Melting Point · 3 件

98.6 to 113 °F (EPA, 1998)

36.5 °C

39.5 °C

Vapor Pressure · 2 件

0.000053 [mmHg]

0.0001 [mm Hg] @25 °C

Physical Description · 2 件

Phosfolan is a colorless to yellow solid. Used as an insecticide. (EPA, 1998)

Colorless to yellow solid; [CAMEO] Yellow crystalline solid; [MSDSonline]

Stability/Shelf LifeStable in aq soln under neutral or slightly acidic conditions but hydrolyzed at pH greater than 9 or less than 2.
Collision Cross Section

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

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory InformationThe 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.)
DOT LabelPoison
Fire Hazards · 1 件

(Non-Specific -- Organophosphorus Pesticide, n.o.s.) This material may burn but does not ignite readily. Container may explode in heat of fire. When heated to decomposition, it emits very toxic fumes of oxides of phosphorus, sulfur, and nitrogen. Hydrolyzed by alkalies. (EPA, 1998)

Health HazardsSimilar to parathion. Death may result due to respiratory arrest as a result of paralysis of respiratory muscles and intense bronchoconstriction. Also considered a cholinesterase inhibitor. (EPA, 1998)
Hazards Summary · 1 件

Decreased erythrocyte cholinesterase activity in heavy occupational exposure by 31-43% by the end of the first hour; Nearly half of the cholinesterase activity had recovered by 48 hours, with full recovery taking 3-4 weeks; No adverse clinical observations in 90 day feeding with dogs at 1 mg/kg; Cholinesterase inhibition noted in animal studies, but no chronic neurotoxicity seen in chickens surviving high doses; [HSDB] 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]

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

... IN PLANTS & ANIMALS, /PHOSFOLAN/ IS METABOLIZED AT THE N-P BOND TO LESS TOXIC, WATER-SOLUBLE COMPOUNDS.

A SINGLE ORAL DOSE (2 MG/KG) TO RAT OF [(14)C-(C=N)]PHOSFOLAN WAS RAPIDLY METABOLIZED TO GIVE AS MAJOR METABOLITES THIOCYANATE AND CARBON DIOXIDE (20%). ... FOURTEEN MINOR URINARY METABOLITES WERE IDENTIFIED ... THE LIKELY INITIAL STEPS IN BIOTRANSFORMATION OF PHOSFOLAN ARE P-N CLEAVAGE &/OR S-OXIDATION.

Results are presented of studies on the metabolism of two (14)C-dithiolane insecticides (phosfolan and mephosfolan) labeled in the imido carbon position. Rats, cotton plants, and a simulated rice paddy environment were used in the studies. In rats, both insecticides showed their major degradation route to be hydrolysis to iminodithiolane, then to thiocyanate, then CO2. In cotton plants treated with mephosfolan, hydroxylation of the methyl moiety of the iminodithiolane ring and conjugation as glucoside was a significant pathway. When a rice paddy environment was treated with mephosfolan, mephosfolan was found in the rice plants, but did not accumulate in the rice grain. The rice plants assimilated mephosfolan rapidly, degraded it, and incorporated the (14)C-carbon into the natural plant products. Mephosfolan was readily metabolized by fish in the paddy environment into the thiocyanate and many polar metabolites.

Absorption, Distribution and Excretion · 2 件

A SINGLE ORAL DOSE (2 MG/KG) TO THE RAT OF (14)C-(C=N)PHOSFOLAN (CYOLANE) WAS RAPIDLY METABOLIZED ... THIOCYANATE WAS PRESENT IN LIVER, KIDNEY, & FAT, & WAS ALSO EXCRETED IN THE URINE (24%).

CYOLANE IS ... ACTIVE ... IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION.

用途と製造

Uses · 3 件

Used as systemic insecticide; [HSDB]

Farming (Pesticides) [Category: Industry]

SYSTEMIC INSECTICIDE; LEAF-PENETRATING, FOR LEAF-FEEDING LARVAE AND OTHER COTTON INSECTS. /DISCONTINUED/

Methods of ManufacturingBY THE REACTION OF 2-IMINO-1,3-DITHIOLAN WITH DIETHYL PHOSPHOROCHLORIDATE.

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

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
PubChem CID
13689
DTXSID
DTXSID1042285
ChEBI
CHEBI:82145
UNII
CHJ98J84AY
EC Number
213-423-2
Nikkaji
J9.472B
165.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1042285]
Other Experimental PropertiesBP: 115-118 °C @ 1X10-3 MM HG; COLORLESS TO YELLOW SOLID; SOLUBILITY: 650 G/L WATER; SOL IN ACETONE, BENZENE, CYCLOHEXANE, ETHANOL, TOLUENE; SLIGHTLY SOL IN ETHER; SPARINGLY SOL IN HEXANE /TECHNICAL/

物理化学的性質

融点
40.75 °C · 40.75°C
沸点
116.5 °C · 116.5°C
比重(密度)
1.42 · 1.42±0.1 g/cm3(Predicted)
屈折率
25 D · n25D 1.5463
貯蔵温度
2 · 2-8°C
溶解性
クロロホルム(微量)、メタノール(微量)
酸解離定数(Pka)
-4.95 · -4.95±0.20(Predicted)
外見
個体
色
白からオフホワイトへ
Henry's Law Constant
5.1 · 5.1×104 mol/(m3Pa) at 25℃, Ebert et al. (2023)
EPAの化学物質情報
Phosfolan (947-02-4)

化学的性質

化学的特性Phosfolan is a colorless to yellow solid.

Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsUSEPA; Chemical Profile: Phosfolan (1985). Chemical identity; exposure limits; physicochemical data; fire and explosion data; reactivity data; health hazrads; uses (insecticide); precautions for safe handling and use.
Reactivity Profile · 1 件

Organophosphates, such as PHOSFOLAN, 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.

Air and Water ReactionsHydrolyzed by alkalis. [EPA, 1998].
Hazard Classes and Categories · 4 件

Acute Tox. 2 (100%)

Acute toxicity (dermal) - category 1

Acute toxicity (Oral) - Category 2

Acute Tox. 1

安全と保護具

Fire Fighting(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. Wear positive pressure breathing apparatus and special protective clothing.
First AidNote: Phosfolan is a cholinesterase inhibitor.
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]

Nonfire Spill Response(Non-Specific -- Organophosphorus Pesticide, n.o.s.) Keep unnecessary people away. Do not touch spilled material. Use water spray to reduce vapors. Take up spills with noncombustible absorbent materials.
Isolation and EvacuationExcerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:
Protective Action Criteria (PAC) · 3 件

0.027 [mg/m3]

0.29 [mg/m3]

1.8 [mg/m3]

Personal Protective Equipment (PPE) · 1 件

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

毒性情報

Ecotoxicity Values · 5 件

LD50 HOUSE SPARROW PERCUTANEOUS 18 MG/KG

LD50 HOUSE SPARROW ORAL 2.4 MG/KG

LD50 QUELEA PERCUTANEOUS 10 MG/KG

LD50 QUELEA ORAL 1.8 MG/KG

LD50 Mallard 3 mo old males oral 3.18 mg/kg (95% confidence limit 2.52-4.00 mg/kg) /Technical, 89.5%/

Environmental Fate · 5 件

TERRESTRIAL FATE: IT IS NON-PERSISTENT IN SOIL ... .

TERRESTRIAL FATE: THE BIOLOGICAL HALF LIFE OF CYOLANE IN SANDY LOAM SOIL COLUMN WAS 3.5 DAYS. TOTAL CYOLANE IN DRAINAGE WATER AFTER 14 DAYS WAS 60.6% OF THE ORIGINAL AMT PLACED ON THE COLUMN. ONE HR AFTER CYOLANE WAS PLACED ON THE COLUMN, 20.62% WAS FOUND IN THE FIRST INCH, 10.08% IN THE SECOND INCH, 4.46% IN THE THIRD INCH, 4.61% IN THE FOURTH INCH, 9.50% IN THE FIFTH INCH, AND 19.46% IN THE SIXTH INCH.

TERRESTRIAL FATE: If released to soil, an estimated soil adsorption coefficient of 2.8(1-2,SRC) indicates that cyolane will display very high mobility in soil(3). Cyolane may undergo slow hydrolysis in basic soils with a pH >9(2,SRC).

AQUATIC FATE: If released to water, cyolane is expected to undergo rapid sensitized photolysis(1-2). The half-life for the sunlight photolysis of cyolane is expected to range from 14-18 days in the upper layer of clear water(1). Cyclic S,S-dipropylene dithiocarbonate, 2-imino-5-methyl-1,3-dithilane, diethyl phosphate, ethyl phosphate and phosphoric acid are produced in this reaction(1). Cyolane may undergo slow hydrolysis in basic waters with a pH >9(3,SRC). An estimated bioconcentration factor of 0.32(3-4,SRC) and an estimated soil adsorption coefficient of 2.8(3-4,SRC) indicate that cyolane will not bioconcentrate in fish and aquatic organisms nor will it adsorb to sediment and suspended organic matter(SRC).

ATMOSPHERIC FATE: If released to the atmosphere, cyolane may undergo a rapid gas-phase reaction with photochemically produced hydroxyl radicals. An estimated half-life for this process is 7 hours(2,SRC). It may undergo atmospheric removal by direct photolytic degradation(1,2,SRC). The water solubility of cyolane, 650,000 mg/L at 25 °C(4) indicates that it may also undergo atmospheric removal by wet deposition processes(SRC).

Adverse EffectsOther Poison - Organophosphate
Soil Adsorption/Mobility · 1 件

A soil adsorption coefficient of 2.8 can be calculated for cyolane using an appropriate regression equation(1,SRC) and its water solubility, 650,000 mg/L at 25 °C(2). This value indicates that cyolane will display very high mobility in soil(3).

Natural Pollution SourcesCyolane is an anthropogenic compound and it is not known to be produced by natural sources. (SRC)
Human Toxicity Excerpts · 2 件

WORKERS EXPOSED TO PHOSFOLAN SHOWED A HIGH REDUCTION IN CHOLINESTERASE ACTIVITY OF THE ERYTHROCYTES. THIS DECR IN THE ACTIVITY AT THE END OF THE FIRST HR RANGED 13.6-43.8% AND 31.1-43.8% IN THE LESS EXPOSED AND HIGHLY EXPOSED WORKERS, RESPECTIVELY. ABOUT HALF OF THE INHIBITED ENZYME ACTIVITY WAS RECOVERED AFTER 48 HR. THE RATE OF RECOVERY WAS SLOW AFTER THAT & IT TOOK APPROX 3-4 WK TO RETURN TO PREEXPOSURE LEVEL.

Symptomatology: 1. Nausea ... vomiting, abdominal cramps, diarrhea, excessive salivation ... 2. Headache, giddiness, vertigo & weakness. 3. Rhinorrhea & sensation of tightness in chest are common in inhalation exposure. 4. Blurring or dimness of vision, miosis ... Tearing, ciliary muscle spasm, loss of accommodation & ocular pain ... Mydriasis ... sometimes seen ... probably due to sympatho-adrenal discharge. 5. Bradycardia or tachycardia. Varying degrees of AV heart block are described, as well as atrial arrhythmias. 6. Loss of muscle coordination, slurring of speech, fasciculations & twitching of muscles (particularly of tongue & eyelids, & generalized profound weakness. 7. Mental confusion, disorientation & drowsiness. 8. Difficulty in breathing, excessive secretion of saliva & of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi & hypertension (presumably due to asphyxia). 9. Random jerky movements, incontinence, convulsions, & coma. 10. Death primarily due to resp arrest arising from failure of resp center, paralysis of resp muscles, intense bronchoconstriction or all three. /Parathion/

Artificial Pollution SourcesCyolane is an experimental systemic insecticide use for the control of several cotton, cabbage and tobacco insects(1-2) and it was released to the environment where it was experimentally used(SRC).
Environmental Bioconcentration · 1 件

A bioconcentration factor of 0.32 can be calculated for cyolane using an appropriate regression equation(1,SRC) and its water solubility, 650,000 mg/L at 25 °C(2). This value indicates that cyolane will not bioconcentrate in fish and aquatic organisms(SRC).

Non-Human Toxicity Excerpts · 5 件

IN 90-DAY FEEDING TRIALS DOGS RECEIVING 1 MG/KG DAILY SHOWED NO CLINICAL SYMPTOMS.

CYOLANE-TREATED ALFALFA HAY WAS FED TO COW 1 YR AFTER TREATMENT OF ALFALFA. CHOLINESTERASE WAS DEPRESSED & DID NOT RETURN TO NORMAL LEVELS UNTIL 3 MO AFTER FEEDING OF CYOLANE-CONTAMINATED HAY HAD BEEN DISCONTINUED.

Signs of intoxication /in mallards/: Polydipsia, ataxia, wings spread, wing-drop, falling, prostration, using wings for pedestrian locomotion, immobility, wing tremors, bradypnea, dyspnea, spasms, tonic convulsions, terminal wing-beat convulsions and opisthotonos. Signs appeared as soon as 8 min and mortalities usually occurred about 30 min after treatment. Prolonged signs included asthenia and myasthenia. Remission took up to 1 wk. /Technical, 85.9%; oral admin/

MUSCARINIC SIGNS OF /ORGANOPHOSPHORUS CMPD/ ... CONSIST OF HYPERSALIVATION, LACRIMATION, SWEATING & NASAL DISCHARGE. MIOSIS, DYSPNEA, VOMITING, DIARRHEA & FREQUENCY OF URINATION ... NICOTINIC EFFECTS CONSIST OF FASCICULATION OF MUSCLES, WEAKNESS & PARALYSIS. THE CENTRAL EFFECTS INCL NERVOUSNESS, APPREHENSION, ATAXIA, CONVULSIONS & COMA. DEATH IS DUE TO RESP FAILURE, OR SOMETIMES CARDIAC ARREST. THERE IS LITTLE DIFFERENCE BETWEEN SYMPTOMS PRODUCED BY DIFFERENT ... CMPD, BUT ROUTE OF ABSORPTION MAY INFLUENCE ONE SYSTEM MORE THAN ANOTHER. /ORGANOPHOSPHORUS CMPD/

For more Non-Human Toxicity Excerpts (Complete) data for CYOLANE (7 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 件

The half-lives for the sunlight photolysis of cyolane in distilled water and rice patty water were 18 days and 14 days(1). The products of this photosensitized reaction were cyclic S,S-dipropylene dithiocarbonate, 2-imino-5-methyl-1,3-dithilane, diethyl phosphate, ethyl phosphate and phosphoric acid(1). Aqueous solutions of cyolane initially at a concn of approx 1500 mg/g decreased to approx 100 mg/g after 300 hours of irradiation by Egyptian sunlight(2). Photolysis on leaf surfaces was slower than that observed in water(2). Cyolane is stable to hydrolysis under neutral and acidic pHs (> pH 2) but slowly decomposes at pHs >9(3). An estimated rate constant for the gas-phase reaction of cyolane with photochemically produced hydroxyl radicals of 5.4X10-11 cu cm/molec-sec(4,SRC) translates to an atmospheric half-life of 7 hours(SRC) using an average atmospheric hydroxyl radical concn of 5X10-5 molec/cu m(4).

Environmental Fate/Exposure Summary · 1 件

Cyolane is an anthropogenic compound which was considered as a systemic a systemic insecticide. It could be released to the enivornment if it were produced, formulated or used as an insecticide. If released to soil, it is expected to display very high mobility. Cyolane may undergo slow hydrolysis in basic soils with a pH >9. If released to water, cyolane is expected to undergo rapid sensitized photolysis. The half-life for the sunlight photolysis of cyolane in the upper layer of clear water is expected to range from 14-18 days. Cyolane may undergo slow hydrolysis in basic waters with a pH >9. Cyolane is not expected to bioconcentrate in fish and aquatic organisms nor will it adsorb to sediment and suspended organic matter. If released to the atmosphere, cyolane may undergo a rapid gas-phase reaction with photochemically produced hydroxyl radicals at an estimated half-life of 7 hours. It may also undergo atmospheric removal by direct photolytic degradation and by wet deposition processes. Occupational exposure to cyolane may occur by dermal contact during its production, formulation or use. (SRC).

Non-Human Toxicity Values · 3 件

LD50 CHICKEN ORAL 5.2 MG/KG

LD50 Rat oral 8.9 mg/kg

LD50 Rabbit dermal 23 mg/kg

安全データ

tsca
TSCA listed
rtecs
NJ6475000
ridadr
2783
risk_code
27/28
hazard_code
T+
safety_code
28-36/37-45
hazard_class
6.1(a)
packing_group
I
有毒物質データの
947-02-4(Hazardous Substances Data)
Formulations/Preparations
EMULSIFIABLE CONCENTRATE (250 G AI/LITER) AND GRANULES (20-50 G AI/KG).
General Manufacturing Information · 3 件

Phosphoramidic acid, N-1,3-dithiolan-2-ylidene-, diethyl ester: ACTIVE

... IT IS A SYSTEMIC INSECTICIDE FOR USE AGAINST SUCKING INSECTS, MITES & LEPIDOPTEROUS LARVAE. IT CONTROLS PRODENIA SPECIES & SPODOPTERA LITTORALIS ON COTTON @ 0.75-1.0 KG/HA; JASSIDS & WHITEFLIES @ 0.5 KG/HA; TRICHOPLUSIA NI AT 1 KG/HA; ALSO THRIPS TABACI AT 30 G/100 L.

CYOLANE IS A CONTACT & STOMACH POISON WITH SYSTEMIC ACTIVITY IN PLANTS THROUGH ROOT & FOLIAR ABSORPTION. IN FIELD TRIALS IT HAS GIVEN EXCELLENT CONTROL OF...LYGUS BUGS (LYGUS HESPERUS), ALFALFA WEEVIL (HYPERA POSTICA), MITES, THRIPS, ALABAMA ARGILLACE JASSID AND WHITEFLIES OF COTTON; CYRTOPELTIS OF TOBACCO.

応用分野

使用Phosfolan was identified and determined to be a residual pesticide in okra samples.

一般的な説明Colorless to yellow solid. Used as an insecticide.

上流・下流製品情報

上流原料

酢酸ナトリウムフェニルエーテルDithiolan-2-imine

下流製品

Phosphorous acid chloride and phosphorus dichloride