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グラモキソン

Paraquat dichloride

HCID 15938
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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
1910-42-5
標準SMILES
C[n+]1ccc(-c2cc[n+](C)cc2)cc1.[Cl-].[Cl-]
InChIKey
FIKAKWIAUPDISJ-UHFFFAOYSA-L
分子式
C12H14N2.2Cl
平均分子量
257.16 g/mol
単同位体質量
256.0534038

概要

Paraquat dichloride is a colorless to yellow crystalline solid. Used as a contact herbicide and desiccant. (EPA, 1998)

名称と識別子

優先名称
Paraquat dichloride
IUPAC
1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium dichloride
現地名
グラモキソン
英語名
Paraquat dichloride
分子式
C12H14Cl2N2
分子量
257.16

名称と別名

Paraquat dichloride1910-42-5Methyl viologenMethyl viologen dichloridePathclearPillarxoneCrisquatDexuronGramixelGramuronEsgramToxer total
名称をさらに表示
1,1'-ジメチル-4,4'-ビピリジニウムジクロリド1,1'-ジメチル-4,4'-ビピリジニウムジクロリド水和物1,1'-ジメチル-4,4'-ビピリジニウム·ジクロリドメチルビオローゲン1,1'-ジメチル-4,4'-ビピリジニウム·2クロリドパラコートジクロリドグラモキシンメチルビオロゲンジクロリドパラクァットジクロリドメチルビオロゲン1,1'-ジメチル-4,4'-ビピリジニウム=ジクロリドパラコ-トパラコートジクロリド標準品メチルビオロゲン水和物二塩化メチルビオロゲンパラコト1,1′-ジメチル-4,4′-ジピリジニウム二塩化物1,1'-ジメチル-4,4'-ビピリジニウム=ジクロリド (別名 パラコートまたはパラコートジクロリド)二塩化パラコート二塩化1,1'-ジメチル-4,4'-ビピリジウム1,1'-ジメチル-4,4'-ビピリジニウム=ジクロリドN 水和物TOTALPARAQUAParaquat dichloridPARAQUAT DICHLORIDE TETRAHYDRATE
Ortho paraquat clParaquat-dichloride1,1'-Dimethyl-4,4'-bipyridinium dichlorideCekuquatGaloksonGramoxoneHerbaxonHerboxone

データベース識別子

CAS
1910-42-5、4685-14-7
PubChem CID
15938
DTXSID
DTXSID7024243
ChEMBL
CHEMBL458019
ChEBI
CHEBI:28786
UNII
2KZ83GSS73
EC Number
217-615-7

物性

構造計算による物性

極性表面積
7.8 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
1
重原子数
16
形式電荷
0
複雑度
145

実験および物理化学的性質

Pesticides · 2 件

Pesticide -> EPA IRIS

Pesticides -> Herbicides, Bipyridyl

LogP-4.5
Density · 4 件

1.24 to 1.26 at 68 °F (NTP, 1992)

1.24 g/cm³

1.24

1.24

Solubility · 3 件

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)

Solubility in water, g/100ml at 20 °C: 62

Miscible

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3 件

Decomposes (NIOSH, 2024)

decomposes

Decomposes

Decomposition300 °C
Melting Point · 3 件

Decomposes 572 °F (EPA, 1998)

572 °F (decomposes)

572 °F (Decomposes)

Vapor Pressure · 5 件

Approximately 0 (EPA, 1998)

0.0000001 [mmHg]

Vapor pressure, Pa at 25 °C:

<0.0000001 mmHg

<0.0000001 mmHg

Physical Description · 5 件

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

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

P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H290 (13.6%): May be corrosive to metals [Warning Corrosive to Metals]

P234, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Hazard Traits - Hazard Trait Undefined

Paraquat dichloride is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

REACH registered substance: Paraquat-dichloride (EC: 217-615-7)

Paraquat dichloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

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 - 4,4'-Bipyridinium, 1,1'-dimethyl-, dichloride: Human health tier I assessment
DOT LabelPoison
Fire Hazards · 2 件

Avoid strong oxidizers. (EPA, 1998)

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsCan cause death due to severe injury to the lungs. The lowest lethal oral dose reported in humans is 43 mg/kg. (EPA, 1998)

化学と産業

薬理情報

Biological Half-LifeAnimal studies: less than 6 hours; other animal studies have found measurable paraquat 26 days after ingestion; [TDR, p. 991]
Metabolism/Metabolites · 1 件

Paraquat is poorly absorbed after oral exposure. It is not metabolized but is reduced to an unstable free radical which is then re-oxidized to reform the cation and produce a superoxide anion. It is excreted moslty in the urine,and in small fraction also in the feces (A606, L1008).

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

用途と製造

Uses · 3 件

Used as a contact herbicide on weeds; [EXTOXNET] Used in animal experiments as a model of Parkinson's syndrome at doses several orders of magnitude greater than occupational exposure levels; [PMID 16217247]

Farming (Pesticides) [Category: Industry]

Paraquat is used as a quaternary ammonium herbicide; one of the most widely used herbicides in the world. It is also often used in science to catalyze the formation of reactive oxygen species (ROS). (L421).

Use ClassificationHERBICIDES
応用分野 · 6 件

解説パラコート,無色の結晶.分解点340 ℃.水溶解度620 g L-1(20 ℃).光化学系Ⅰから電子を受けとり,酸素分子を還元して超酸化物を発生させ,細胞膜を損傷する非選択性除草剤.

用途パラコート,白色結晶で水に溶ける。茎葉に処理することによって植物体内で活性酸素を生成し,ほとんどすべての雑草を枯死させる。土壌中では速やかに分解される。

用途酸化還元酵素又は酵素系の水素(電子)受容体、供与体、中間電子伝達体。

用途ビピリジニウム系除草剤の商品名で,一般名としてパラコートが用いられる。イギリスのICI社が,同系列の除草剤,ジクワットにひきつづいて,1950年代に開発した除草剤である。非選択的,非ホルモン系除草剤で,茎葉散布により接触的に殺草作用を示す。土壌表面で容易に吸着,不活性化するので,果樹園の下草の除草,非農地の除草に適し,水稲刈取り後のミズガヤツリ,マツバイの除草にも用いられる。パラコート, この薬剤は,光合成の明反応系から生ずる励起電子により還元を受け,さらに空気中の酸素により酸化されてもとの構造にもどる際に,生体内に過酸化物が生じ,これが殺草作用の原因となる。

関連反応

3 件
反応記録を作成
HRID 1674471 の反応式
HRID 1674471生成物としてuspto-grants-2011_08
HRID 1674472 の反応式
HRID 1674472生成物としてuspto-grants-2011_08
HRID 1762394 の反応式
HRID 1762394生成物としてuspto-grants-1989_05

化合物ノート

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ノートを作成反応を作成見積依頼を出す

Paraquat dichloride is a colorless to yellow crystalline solid. Used as a contact herbicide and desiccant. (EPA, 1998)

Yellow solid with a faint, ammonia-like odor. [herbicide] [Note: Paraquat may also be found commercially as a methyl sulfate salt C12H14N2+2CH3SO4.]; [NIOSH]

COLOURLESS HYGROSCOPIC CRYSTALS.

[herbicide] [Note: Paraquat may also be found commercially as a methyl sulfate

Yellow solid with a faint, ammonia-like odor. [herbicide] [Note: Paraquat may also be found commercially as a methyl sulfate salt C12H14N2 • 2CH3SO4.]

物理化学的性質

融点
300 °C · >300 °C(lit.)
沸点
403.89 °C · 403.89°C (rough estimate)
比重(密度)
1.25 · 1.25
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
1.64 · 1.6400 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
Methanol (Sligthly)
外見
結晶または結晶性粉末
色
ベージュまたはピンクからブラウン
水溶解度
溶ける
Merck
7031 · 7031
安定性
安定。強力な酸化剤とは相容れない。
LogP
-4.5 at · -4.5 at 20℃
CAS データベース
1910 · 1910-42-5(CAS DataBase Reference)
EPAの化学物質情報
Paraquat dichloride (1910-42-5)

化学的性質

化学的特性off-white powder

Hazards Summary · 1 件

Contact injuries in workers include skin rashes, burns, eye damage from splashes, nail damage, and nasal bleeding. Parquat absorption through the skin can contribute to systemic toxicity, especially when contacting damaged skin or sensitive areas like the buttocks and genitalia. Toxic ingestion: low doses (<20 mg/kg) cause local irritation to oral and GI mucosa; moderate doses (20-40 mg/kg) cause renal, liver and lung damage with respiratory failure within 2-3 weeks; high doses (>40 mg/kg) cause pulmonary fibroplasia, respiratory failure, and death within 1-7 days. [ACGIH] Classified as highly toxic, paraquat may be used only by certified applicators. [EXTOXNET] Prolonged contact will cause blistering of skin. Poisoning usually occurs after toxic ingestion, e.g., attempted suicide. [EPA Pesticides] Phototoxic contact dermatitis reported in farmworkers; [Kanerva, p. 1823] A multigenerational study in rats given 100 ppm or 300 ppm dietary paraquat showed no effects on fertility or neonatal morbidity and mortality. In mice, maternal feeding with 125 ppm paraquat caused increased mortality in pups that was related to lung injury. [ACGIH] Among the many herbicides in use, only the bipyridyl compounds have appeared to produce hepatic injury in humans. Even these agents have produced hepatic injury only as the result of ingestion of large amounts, not because of environmental contamination and questionably as the result of occupational exposures. [Zimmerman, p. 415] Paraquat has a chemical structure similar to MPTP, but animal studies have failed to show that paraquat causes parkinsonism. [Rosenstock, p. 1111] See Paraquat.

Reactive GroupQuaternary Ammonium and Phosphonium Salts
EC ClassificationSymbol: T+, N; R: 24/25-26-36/37/38-48/25-50/53; S: (1/2)-22-28-36/37/39-45-60-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
Reactivity Profile · 1 件

PARAQUAT DICHLORIDE is stable in acidic media, but unstable in alkaline media. It is photochemically decomposed by UV irradiation in aqueous solutions and is rapidly inactivated by soil. The neat chemical may be sensitive to light. This compound is corrosive to metal and it can react with strong acids, bases, and oxidizing agents. It is hydrolyzed by alkali compounds and it is inactivated by inert clays and anionic surfactants. (NTP, 1992)

Chemical DangersDecomposes above 300 °C . This produces toxic fumes including nitrogen oxides and hydrogen chloride. Attacks metals.
Flammable LimitsNoncombustible Solid

安全と保護具

Fire Fighting · 2 件

This material is a bipyridilium compound. Procedures for bipyridilium pesticides are as follows. Small fires: dry chemical, carbon dioxide, water spray, or foam. Large fires: water spray, fog, or foam. Move container from fire area if you can do so without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material. (EPA, 1998)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 件

Fresh air, rest. Refer immediately for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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

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

First Aid · 2 件

Warning: Effects occur in two stages, immediate and delayed. Caution is advised. Exposure to paraquat may be fatal; there is no effective antidote.

(General first aid procedures)

Safe StorageKeep in a well-ventilated room. Well closed. Separated from food and feedstuffs. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access.
Exposure Control and Personal Protection0.1 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Nonfire Spill Response · 1 件

(Non-Specific -- Bipyridilium Pesticide) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. If water pollution occurs, notify appropriate authorities. Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors.

Spillage Disposal · 1 件

Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Eye PreventionWear face shield or eye protection in combination with breathing protection if powder.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST! STRICT HYGIENE!

毒性情報

Treatment · 1 件

In case of oral exposure, administer charcoal as a slurry. Consider after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. The treatment is symptomatic and supportive. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, remove contaminated clothing and jewellery. Wash the skin, including hair and nails, vigorously; do repeated soap washings. Discard contaminated clothing. (T36)

Target Organs · 2 件

Respiratory

Eyes, skin, respiratory system, heart, liver, kidneys, gastrointestinal tract

Health Effects · 1 件

It can cause temporary damage to nails and if swalloed, may cause nose bleeding. Long term exposures to paraquat would most likely cause lung and eye damage. Some suspect a possible link to a greater incidence of Parkinson's disease. Pancreatitis may develop in some cases of acute. Paraquat is caustic to the oral, esophageal, and gastric mucosa (T36, A545, L421).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 3 件

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

inhalation, skin absorption, ingestion, skin and/or eye contact

Inhalation (T44) ; oral (T44) ; eye contat (T44) ; dermal (T44)

Toxicity Summary · 1 件

The mechanisms of the toxic effects of paraquat are largely the result of a metabolically catalyzed single electron oxidation reduction reaction, resulting in depletion of cellular NADPH and the generation of potentially toxic forms of oxygen such as the superoxide radical (A607). Recent studies have demonstrated paraquat cytotoxicity occurs in the mitochondria and particularly in mitochondrial-rich tissues. The mitochondrial NADH-dependent PQ reductase containing a voltage-dependent anion channel 1 (VDAC1) appears to be largely responsible for paraquat cytotoxicity. When mitochondria are incubated with NADH and paraquat, the superoxide anion is produced, and the mitochondria rupture. Ruptured mitochondria lead to rapid cell death (A3102).

Signs and Symptoms · 6 件

Cough. Sore throat. Headache. Nosebleeds.

Redness.

Redness. Burning sensation. Pain.

Sore throat. Abdominal pain. Nausea. Vomiting. Diarrhoea.

irritation eyes, skin, nose, throat, respiratory system; epistaxis (nosebleed); dermatitis; fingernail damage; irritation gastrointestinal tract; heart, liver, kidney damage

Eye or skin irritation; hypotension may develop after large ingestion; epistaxis and sore throat may develop after inhalation. Nausea, vomiting, diarrhea, and abdominal pain are common (T36).

Acute Toxicity LinkChemical: PARAQUAT
ICSC Environmental Data · 1 件

The substance is very toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. 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.

EPA IRIS Information · 3 件

Paraquat

Respiratory

4.5 x 10 ^-3 mg/kg-day

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity Data · 2 件

LCLo (rat) = 1 mg/m3/6H for respirable dust;

LD50: 150 mg/kg (Oral, Rat) (L1008) LD50: >480 mg/kg (Dermal, Rabbit) (L1008)

安全データ

OEB
D
OEL
TWA: 0.1 mg/m3 (resp) [skin]
wgk
3
IDLA
1 mg/m3
rtecs
DW2275000
ridadr
UN 2811 6.1/PG 1
毒性
LD50 orally in rats: 125 mg/kg (Conning)
PRTR法
第一種指定化学物質
hs_code
29333990
risk_code
24/25-26-36/37/38-48/25-50/53
化審法
(5)-3722
安衛法
57,57-2
hazard_code
T+,N
safety_code
22-28-36/37/39-45-60-61-28A
hazard_class
6.1(a)
packing_group
II
毒劇物取締法
毒物

説明Paraquat dichloride is a dark blue liquid, non-combustible, stable herbicide chemical. It is incompatible with strong oxidising agents. On contact with fire paraquat decomposes gives off irritating or toxic fumes (or gases), nitrogen oxides, and hydrogen chloride. Paraquat dichloride contact and storage destroys metal. Paraquat dichloride hydrolyses in alkaline media and reacts with aluminium to produce hydrogen gas. Paraquat (N,N′-dimethyl-4,4′-bipyridinium dichloride) is one of the most widely used herbicides in the world. Paraquat dichloride is a herbicide currently registered to control weeds and grasses in many agricultural and non-agricultural areas. It is used preplant or preemergence on vegetables, grains, cotton, grasses, sugar cane, peanuts, potatoes, and tree plantation areas; post-emergence around fruit crops, vegetables, trees, vines, grains, soybeans, and sugar cane. It is also used on non-crop areas such as public airports, electric transformer stations, and around commercial buildings to control weeds. It has been reported that about seven pesticide products are registered which contain the active ingredient paraquat dichloride and classified as restricted use pesticides (RUPs). Paraquat dichloride and the products are primarily intended for ‘Occupational Use’. In the United States, Paraquat is classified as ‘restricted commercial use’, and people must obtain a license to use the product.

一般的な説明Colorless to yellow crystalline solid. Used as a contact herbicide and desiccant.

調製方法

純化方法Recrystallise the dichloride from MeOH/acetone mixture. It has also been recrystallised three times from absolute EtOH [Bancroft et al. Anal Chem 53 1390 1981]. Dry it at 80o in a vacuum. [Beilstein 23/8 V 30.]

上流・下流製品情報

上流原料

ピリジン4-ヨードピリジン4,4'-ビピリジル4-ピリジルボロン酸1,1'-ジメチル-4,4'-ビピリジニウム·2ヨージドジメチル硫酸ククルビット[7]ウリル 水和物クロロ酢酸ヨードメタン4-ブロモピリジンクロロメタン