グラモキソン

Paraquat dichloride

HCID 15938CAS 1910-42-5

基本情報

標準SMILES
C[n+]1ccc(-c2cc[n+](C)cc2)cc1.[Cl-].[Cl-]
InChIKey
FIKAKWIAUPDISJ-UHFFFAOYSA-L
分子式
C12H14Cl2N2
平均分子量
257.16 g/mol
単同位体質量
256.0534038

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
1,1'-Dimethyl-4,4'-bipyridinium dichlorideOrtho paraquat clParaquat-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

実験および物理化学的性質

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

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)

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

化学的性質

化学的特性off-white powder

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral];H311: Toxic in contact with skin [Danger Acute toxicity, dermal];H315: Causes skin irritation [Warning Skin corrosion/irritation];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H330: Fatal if inhaled [Danger Acute toxicity, inhalation];H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H372 **: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure];H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

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

危険有害性情報

Regulatory Information · 5 件

Hazard Traits - Hazard Trait Undefined;Authoritative List - CECBP - Priority Chemicals;Report - if used as a fragrance or flavor ingredient

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

Status: Active Update: 26-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/29834

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;IMAP assessments - 4,4'-Bipyridinium, 1,1'-dimethyl-, dichloride: Environment 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)
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.

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.;Signs and Symptoms of Acute Paraquat Exposure: Signs and symptoms of acute exposure to paraquat may be severe and include nausea, vomiting, diarrhea, and abdominal pain. A burning sensation of the mouth and esophagus with possible ulceration may occur following ingestion. Eye exposure may result in corneal opacification (cloudiness). Dermatitis and nail atrophy may occur following dermal contact. Delayed effects include transient reversible liver injury, acute renal failure, and progressive pulmonary fibrosis with associated dyspnea (shortness of breath) and pulmonary edema.;Emergency Life-Support Procedures: Acute exposure to paraquat may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination.;Inhalation Exposure:;1. Move victims to fresh air. Emergency personnel should avoid self-exposure to paraquat.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures.;4. RUSH to a health care facility.;Dermal/Eye Exposure:;1. Remove victims from exposure. Emergency personnel should avoid self- exposure to paraquat.;2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;3. Remove contaminated clothing as soon as possible.;4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes.;5. Wash exposed skin areas three times with soap and water.;6. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures.;7. RUSH to a health care facility.;Ingestion Exposure:;1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support.;2. Obtain authorization and/or further instructions from the local hospital for performance of other invasive procedures.;3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of paraquat is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water flush immediately - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

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.;Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal.;Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area.;Large spills: dike far ahead of spill for later disposal. (EPA, 1998)

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 Effects · 1 件

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.;Dermatotoxin - Skin burns.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.;Fibrogenic - Inducing tissue injury and fibrosis (scarring).;ACGIH Carcinogen - Not Classifiable.

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).

法規制情報

Regulatory Information · 5 件

Hazard Traits - Hazard Trait Undefined;Authoritative List - CECBP - Priority Chemicals;Report - if used as a fragrance or flavor ingredient

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

Status: Active Update: 26-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/29834

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.)

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

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。

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.]

関連反応

3 件

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