グラモキソン

Paraquat

HCID 15939CAS 1910-42-5

基本情報

標準SMILES
C[n+]1ccc(-c2cc[n+](C)cc2)cc1
InChIKey
INFDPOAKFNIJBF-UHFFFAOYSA-N
分子式
C12H14N2+2
平均分子量
186.25 g/mol
単同位体質量
186.11460129

概要

Paraquat is an organic cation that consists of 4,4'-bipyridine bearing two N-methyl substituents loctated at the 1- and 1'-positions. It has a role as a geroprotector and a herbicide. It derives from a hydride of a 4,4'-bipyridine.

名称と識別子

優先名称
Paraquat
IUPAC
1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-ium
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

PARAQUAT4685-14-7Paraquat ionParaquat dication1,1'-Dimethyl-4,4'-bipyridiniumDimethyl viologenStarfireMethyl viologen (2+)4,4'-Bipyridinium, 1,1'-dimethyl-Methyl viologen ion(2+)N,N'-Dimethyl-4,4'-bipyridinium1,1'-Dimethyl-4,4'-bipyridyldiylium
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METHYL VIOLOGENTOTALMETHYL VIOLOGEN DICHLORIDEesgramPARAQUAGRAMOXONEParaquat dichloridPARAQUAT DICHLORIDE TETRAHYDRATE1,1'-Dimethyl-4,4'-bipyridinium Dichloride1,1'-Dimethyl-4,4'-bipyridinium Dichloride
1-methyl-4-(1-methylpyridin-1-ium-4-yl)pyridin-1-iumN,N'-Dimethyl-4,4'-bipyridinium dicationN,N'-Dimethyl-gamma,gamma'-dipyridyliumDTXSID3034799PLG39H7695CHEBI:34905Viologen, MethylRefChem:6102

データベース識別子

CAS
1910-42-5、4685-14-7
PubChem CID
15939
DTXSID
DTXSID3034799
ChEMBL
CHEMBL74469
ChEBI
CHEBI:34905
UNII
PLG39H7695
EC Number
225-141-7
Nikkaji
J913J

物性

構造計算による物性

XLogP
1.7
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
0
回転可能結合数
1
重原子数
14

実験および物理化学的性質

Chemical ClassesCarcinogens
Pesticides · 4 件

Pesticide -> EPA IRIS

Herbicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Herbicides, Bipyridyl

LogPlog Kow = -4.22 at pH 7.4
OdorOdorless
Density · 2 件

1.24

1.24 @ 20°C

Color/Form · 4 件

Yellow solid

Off-white powder

...a liquid in various strengths... The form marketed in the U.S. has a blue dye to keep it from being confused with beverages, a sharp odor to serve as a warning, and an agent to cause vomiting if someone drinks it.

Yellow-white hygroscopic powder

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

H290 (100%): 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)

Aggregated GHS information provided per 28 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

危険有害性情報

Regulatory Information · 4 件

Regulation (EC) No 1107/2009 (amended)

2003/112/EC

Paraquat: HSNO Approval: HSR003041 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 - 4,4'-Bipyridinium, 1,1'-dimethyl-: Human health tier I assessment
Fire Potential · 2 件

This chemical is a combustible solid.

Non-flammable in aqueous formulations.

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] Highly toxic via ingestion, inhalation, and skin absorption; [Hawley] See Paraquat dichloride.

Special Reports · 4 件

FAO/WHO; Pesticide Residues in Food - Joint FAO/WHO Meeting on Pesticide Residues: Paraquat (2003) provides documentation of the evaluation by the Joint FAO/WHO Meeting on Pesticide Residues to establish an adi for paraquat.[Available from, as of March 11, 2010: http://www.inchem.org/documents/jmpr/jmpmono/v2003pr08.htm]

USEPA/OPP; Reregistration Eligibility Decision Document - Paraquat Dichloride EPA-738-F-96-018 (August 1997). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of June 25, 2015: http://www.epa.gov/pesticides/reregistration/status.htm]

IPCS; Poisons Information Monograph 399: Paraquat (October 2000). A global database with evaluated information on substances (chemicals, pharmaceuticals, poisonous plants, and poisonous and venomous animals) commonly involved in cases of poisoning.[Available from, as of March 5, 2010: http://www.inchem.org/pages/pims.html]

WHO; Environmental Health Criteria No. 39: Paraquat and Diquat (1984)[Available from, as of March 29, 2010: http://www.inchem.org/documents/ehc/ehc/ehc39.htm]

FIFRA Requirements · 5 件

Tolerances are established for residues of the desiccant, defoliant, and herbicide paraquat (1,1'-dimethyl-4,4'-bipyridinium-ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3463]

Tolerances with regional registration as defined in section 180.1(n), are established for residues of the pesticide paraquat (1,1'-dimethyl-4,4' bipyridinium ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3464]

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. /Paraquat (dichloride) and paraquat bis (methylsulfate)/[Table#3465]

The Agency has determined that paraquat dichloride products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Under the Food Quality Protection Act of 1996, the Agency has determined that there is a reasonable certainty that no harm will result to infants and children from aggregate exposure to paraquat dichloride. There are no residential uses of paraquat dichloride, therefore, there are no risks of dermal or inhalation exposure to infants, children or the general population. Additionally, paraquat is not expected to be a contaminant of drinking water. The Agency has also concluded that there are no other chemicals with a common mode of toxicity as that of paraquat. Therefore, the Agency concludes that products containing paraquat dichloride for all uses are eligible for reregistration as specified in this RED. /Paraquat dichloride/

For more FIFRA Requirements (Complete) data for Paraquat (6 total), please visit the HSDB record page.

安全と保護具

Fire Fighting Procedures · 2 件

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. Poisonous gases are produced in fire. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. Containers may explode in fire. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors or shows any signs of deforming), withdraw immediately to a secure position.

If involved in a fire, control with dry powder or alcohol-resistant foam ... Protective clothing and self-contained breathing apparatus should be worn, to avoid skin contamination and the breathing of toxic fumes. Confine the use of water spray to the cooling of unaffected stock, thus avoiding the accumulation of polluted run-off from the site.

Storage Conditions · 2 件

This chemical is inactivated by inert clays and anionic surfactants. Store in tightly closed containers in a cool, well-ventilated area away from oxidizers, alkylaryl-sulfonate wetting agents, light. Where possible, automatically pump material from drums or other storage containers to process containers. Sources of ignition such as smoking and open flames are prohibited where this chemical is handled, used, or stored. Metal containers involving the transfer of this chemical should be grounded and bonded. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Wherever this chemical is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings.

Store technical material and formulations away from heat, under lock and key, and out of reach of children, animals, and unauthorized personnel. Store in an area designated for pesticide storage, preferably without drains. Store away from foodstuffs and animal feed.

Cleanup Methods · 3 件

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Avoid exposure by the use of appropriate protective clothing, gloves, and goggles or masks. Keep spectators away from leaking or spilled product and prevent smoking, and the use of naked flames, in the immediate vicinity ... Prevent liquid from spreading to other cargo, vegetation, or waterways by containing it with the most readily available barrier material, e.g., earth or sand. Absorb spilled liquid and cover contaminated areas with earth, lime, sand, or other absorbent material; sweep up and place in a secure container for subsequent safe disposal. Spillage: Avoid exposure by the use of appropriate protective clothing and face-shield. Empty any product remaining in damaged or leaking containers into a clean empty drum and label. Absorb spillage with lime, damp sawdust, sand, or earth and dispose of safely ... If spillage is large, contain it by building a barrier of earth or sandbags. Decontaminate empty, damaged, or leaking containers with a 10% sodium carbonate solution, added at the rate of at least 1 L per 20 L drum. Puncture or crush containers to prevent reuse.

If paraquat is spilled, ... ventilate area of spill. Collect spilled material in the most convenient and safe manner and deposit in sealed containers for reclamation. Liquid containing paraquat should be absorbed in vermiculite, dry sand, earth, or a similar material.

Disposal Methods · 5 件

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Paraquat is rapidly inactivated in soil. It is also inactivated by anionic surfactants. Therefore an effective and environmentally safe disposal method would be to mix the product with ordinary household detergent and bury the mixture in clay soil.

If incineration facilities are unavailable for a particular organic or metallo-organic pesticide (except organic mercury, lead, cadmium, and arsenic compounds), additional disposal methods include, soil injection, chemical degradation, burial (in a designated landfill), or well injection. However, persons considering the chemical degradation method should contact EPA's Regional Administrator ... prior to attempting disposal, while the well injection method should only be considered after all reasonable alternative measures have been explored and found to be less satisfactory in terms of environmental protection. If the above approved disposal methods are unavailable, temporary storage of organic and metallo-organic pesticides (except organic mercury, lead, cadmium and arsenic compounds), may be undertaken. /Organic or metallo-organic pesticide/

For more Disposal Methods (Complete) data for Paraquat (7 total), please visit the HSDB record page.

Preventive Measures · 5 件

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in a manner such that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

Entry Restrictions. For sole-active-ingredient end-use products that contain paraquat the product labeling must be revised to adopt the entry restrictions set forth in this section. Any conflicting entry restrictions on the current labeling must be removed. For multiple-active-ingredient end-use products that contain paraquat the entry restrictions set forth in this section must be compared to the entry restrictions on the current labeling and the more protective must be retained. A specific time period in hours or days is considered more protective than "sprays have dried" or "dusts have settled."

The /USEPA/ is establishing the following entry restrictions for non-Worker Protection Standard occupational uses of paraquat end-use products: Do not enter or allow others to enter the treated area until sprays have dried.

For more Preventive Measures (Complete) data for Paraquat (8 total), please visit the HSDB record page.

Allowable Tolerances · 2 件

Tolerances are established for residues of the desiccant, defoliant, and herbicide paraquat (1,1'-dimethyl-4,4'-bipyridinium-ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3457]

Tolerances with regional registration as defined in section 180.1(n), are established for residues of the pesticide paraquat (1,1'-dimethyl-4,4' bipyridinium ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3458]

毒性情報

Body Burden · 1 件

The concentration of paraquat in urine of hand-operated knapsack sprayers in Malaysian rubber plantations ranged from less than 0.01 mg/L to 0.32 mg/L during continuous spray period. Fourteen days following post-spraying, the urinary paraquat concentration was undetectable (less than 0.01 mg/L) for all sprayers(1).

Interactions · 5 件

As a result of nuclear power plants accidents such as Chernobyl or Fukushima, some people were exposed to external and internal ionizing radiation (IR). Human brain is highly sensitive to IR during fetal and postnatal period when the molecular processes are not completely finished. Various studies have shown that exposure to low doses of IR causes a higher incidence of cognitive impairment. On the other hand, in industrialized countries, people are daily exposed to a number of toxicant pollutants. Exposure to environmental chemicals, such as paraquat (PQ), may potentiate the toxic effects induced by radiation on brain development. In this study, we evaluated the cognitive effects of concomitant exposure to low doses of internal radiation ((137)Cs) and PQ during neonatal brain development. At the postnatal day 10 (PND10), two groups of mice (C57BL/6J) were exposed to (137)Cs (4000 and 8000 Bq/kg) and/or PQ (7 mg/kg). To investigate the spontaneous behavior, learning, memory capacities and anxiety, behavioral tests were conducted in the offspring at two months of age. The results showed that cognitive functions were not significantly affected when (137)Cs or PQ were administered alone. However, alterations in the working memory and anxiety were detected in mice exposed to (137)Cs combined with PQ.

Superoxide dismutase (SOD), glutathione, and d-propranolol were evaluated for their ability to protect against paraquat dichloride toxicity in rats. SOD significantly prolonged and increased survival of exposed rats.

Female adult beagles (9-14 kg) were continuously infused with 2.5% or 5.0% taurine (into the radial vein at a rate of 0.85 mL/kg/min for 2 hr) 1 min prior to the injection of paraquat (20 mg/kg sc). Other female beagles were infused with either glycine (40 mM/dL) or 0.9% saline solution prior to paraquat challenge. Pharmacokinetic studies revealed that taurine infusion increased the blood concentration of paraquat and reduced the net content in the kidney and to a lesser extent, in the lung. The excretion of paraquat into the urine was unaltered by taurine infusion. All four beagles infused with 5.0% taurine and injected with 20 mg/kg of paraquat showed a stable condition with tail up and flicking during the infusion, whereas all control dogs given saline or glycine were vomiting and the tail was down between the legs. The infusion of 2.5% taurine had protective effects to a lesser extent against these symptoms. Urinary vol in beagles infused with 5.0% taurine and injected with paraquat was 4 times greater than that in animals given saline and the paraquat injection. The tissue/blood ratio of paraquat in beagles infused with taurine before paraquat injection was sharply reduced compared to dogs infused with saline solution or glycine.

The time required for niacin treated rats to reach 50% mortality increased from 60 to 120 hr and the death rate decreased from 75 to 55%. Niacin prevents a decrease of cellular adenine dinucleotide during paraquat poisoning as has been demonstrated in bacteria.

For more Interactions (Complete) data for Paraquat (25 total), please visit the HSDB record page.

Target OrgansRespiratory
Ecotoxicity Values · 5 件

LD50; Species: Anas platyrhynchos (Mallard) oral 199 mg/kg (95% confidence limit 144-276 mg/kg)

LD50; Species: Anas platyrhynchos (Mallard) percutaneous 600 mg/kg (95% confidence limit 424-848 mg/kg)

LC50; Species: Coturnix japonica (Japanese quail) juvenile 14 days post-hatch; diet 948 ppm for 5 days (95% confidence interval: 768-1168 ppm)

LD50; Species: Drosophila melanogaster (Fruit fly) age 5 days, wild type Oregon-R-strain; environmental exposure route 20 mM for 48 hr

For more Ecotoxicity Values (Complete) data for Paraquat (42 total), please visit the HSDB record page.

Environmental Fate · 4 件

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 15,473-1,000,000(2-7), indicate that paraquat is expected to be immobile in soil(SRC). These values along with field studies and soil column leaching studies have demonstrated that paraquat is strongly adsorbed to soil constituents and does not leach under environmental conditions(8-10). Volatilization of paraquat from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of <3.0X10-14 atm-cu m/mole(SRC), based upon its vapor pressure, <7.5X10-8 mm Hg(11), and water solubility, 6.2X10+5 mg/L(11). Paraquat is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(11). The biodegradation of paraquat is very slow because it strongly adsorbs to clay or organic matters in soils making paraquat unavailable to biodegrade(12). When not in the adsorbed-state, paraquat biodegrades(13-15). Some photodegradation may occur on plant leaves or soil surfaces exposed to sunlight(11-12). Field degradation half-lives in soil are reported as 99-4747 days(7,16-17).

AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 15,473-1,000,000(2-7), indicate that paraquat is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(8) based upon an estimated Henry's Law constant of <3.0X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, <7.5X10-8 mm Hg(9), and water solubility, 6.2X10+5 mg/L(9). Paraquat does not undergo hydrolysis based on tests conducted at pH 5, 7 and 9(10). According to a classification scheme(11), BCFs of 0.05-6.9 reported in rainbow trout, green sunfish, bluegill and channel catfish(12-13), suggest bioconcentration in aquatic organisms is low(SRC). Paraquat present in solution in the unabsorbed state may biodegrade easily in water(14). But when paraquat is adsorbed to clay or organic matter in water, biodegradation will be very slow(14-15). Paraquat will be completely removed from most surface waters in 8-12 days due to sorption to suspended solids and sediment in water; after being fixed to sediment and suspended solids, the disappearance of paraquat is slow(7).

FIELD STUDY: Paraquat resides are removed rapidly from water by adsorption on aquatic weeds and by strong adsorption to bottom mud. Decaying weeds also transport paraquat to bottom mud(1).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), paraquat, which has a vapor pressure of <7.5X10-8 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase paraquat may be removed from the air by wet and dry deposition(SRC). Paraquat does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 件

In tests on sunflower seeds treated with 0.25 or 0.5 kg paraquat/ha, residues of up to 0.9 mg/kg were found in the whole seed, up to 1.2 mg/kg in sunflower meal, and no residue in the oil(1). Paraquat was detected at 0.05 mg/kg in potatoes treated with paraquat as a desiccant, there was no change after the potatoes had been boiled(1). Paraquat was not detected (detection limit 0.02 mg/kg) in 40 composite vegetable samples from Ontario, Canada collected 1980-1985(2). Paraquat was detected in <2% of raw and processed food commodities analyzed under a regulatory monitoring program run 1978-1986 by The Food and Drug Administration(3-4). Commodities included: fruits, vegetables, grains, milk, dairy products, seafood and a variety of processed foods(3-4).

Paraquat residues detected in food crops 3-21 days after desiccation(1).[Table#3466]

法規制情報

FIFRA Requirements · 5 件

Tolerances are established for residues of the desiccant, defoliant, and herbicide paraquat (1,1'-dimethyl-4,4'-bipyridinium-ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3463]

Tolerances with regional registration as defined in section 180.1(n), are established for residues of the pesticide paraquat (1,1'-dimethyl-4,4' bipyridinium ion) derived from application of either the bis(methyl sulfate) or the dichloride salt (both calculated as the cation) in or on the following food commodities:[Table#3464]

Classified for restricted use and limited to use by or under the direct supervision of a certified applicator. /Paraquat (dichloride) and paraquat bis (methylsulfate)/[Table#3465]

The Agency has determined that paraquat dichloride products, labeled and used as specified in this Reregistration Eligibility Decision, will not pose unreasonable risks or adverse effects to humans or the environment. Under the Food Quality Protection Act of 1996, the Agency has determined that there is a reasonable certainty that no harm will result to infants and children from aggregate exposure to paraquat dichloride. There are no residential uses of paraquat dichloride, therefore, there are no risks of dermal or inhalation exposure to infants, children or the general population. Additionally, paraquat is not expected to be a contaminant of drinking water. The Agency has also concluded that there are no other chemicals with a common mode of toxicity as that of paraquat. Therefore, the Agency concludes that products containing paraquat dichloride for all uses are eligible for reregistration as specified in this RED. /Paraquat dichloride/

For more FIFRA Requirements (Complete) data for Paraquat (6 total), please visit the HSDB record page.

CERCLA Reportable Quantities · 1 件

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Paraquat dichloride is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . /Paraquat dichloride/

State Drinking Water Guidelines · 3 件

(AZ) ARIZONA 3 ug/L

(FL) FLORIDA 31.5 ug/L

(ME) MAINE 3 ug/L

Federal Drinking Water GuidelinesEPA 30 ug/L

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

Mechanism of Action · 5 件

The innate immune response is important in paraquat-induced acute lung injury, but the exact pathways involved are not elucidated. The objectives of this study were to determine the specific role of the NLRP3 inflammasome in the process. Acute lung injury was induced by administering paraquat (PQ) intraperitoneally. NLRP3 inflammasome including NLRP3, ASC, and caspase-1 mRNA and protein expression in lung tissue and IL-1beta and IL-18 levels in BALF were detected at 4, 8, 24, and 72 hr after PQ administration in rats. Moreover, rats were pretreated with 10, 30, and 50 mg/kg NLRP3 inflammasome blocker glybenclamide, respectively, 1 h before PQ exposure. At 72 hr after PQ administration, lung histopathology changes, NLRP3, ASC, and caspase-1 protein expression, as well as secretion of cytokines including IL-1beta and IL-18 in BALF were investigated. The NLRP3 inflammasome including NLRP3, ASC, caspase-1 expression, and cytokines IL-1beta and IL-18 levels in PQ poisoning rats were significantly higher than that in the control group. NLRP3 inflammasome blocker glybenclamide pretreatment attenuated lung edema, inhibited the NLRP3, ASC, and caspase-1 activation, and reduced IL-1beta and IL-18 levels in BALF. In the in vitro experiments, IL-1beta and IL-18 secreted from RAW264.7 mouse macrophages treated with paraquat were attenuated by glybenclamide. In conclusion, paraquat can induce IL-1beta/IL-18 secretion via NLRP3-ASC-caspase-1 pathway, and the NLRP3 inflammasome is essential for paraquat-induced acute lung injury.

BACKGROUND: Paraquat (PQ) poisoning is a lethal toxicological challenge that served as a disease model of acute lung injury and pulmonary fibrosis, but the mechanism is undetermined and no effective treatment has been discovered. METHODS AND FINDINGS: We demonstrated that PQ injures mitochondria and leads to mtDNA release. The mtDNA mediated PBMC recruitment and stimulated the alveolar epithelial cell production of TGF-beta1 in vitro. The levels of mtDNA in circulation and bronchial alveolar lavage fluid (BALF) were elevated in a mouse of PQ-induced lung injury. DNaseI could protect PQ-induced lung injury and significantly improved survival. Acute lung injury markers, such as TNFalpha, IL-1beta, and IL-6, and marker of fibrosis, collagen I, were downregulated in parallel with the elimination of mtDNA by DNaseI. These data indicate a possible mechanism for PQ-induced, mtDNA-mediated lung injury, which may be shared by other causes of lung injury, as suggested by the same protective effect of DNaseI in bleomycin-induced lung injury model. Interestingly, increased mtDNA in the BALF of patients with amyopathic dermatomyositis-interstitial lung disease can be appreciated. CONCLUSIONS: DNaseI targeting mtDNA may be a promising approach for the treatment of PQ-induced acute lung injury and pulmonary fibrosis that merits fast tracking through clinical trials.

Paraquat (PQ), one of the most widely used herbicides, has been used for several decades in agriculture. Some studies suggest that PQ has effects on the immune system. Moreover, previous studies have shown that PQ imparted some immunosuppressive effects. In the present study, cytotoxicity assays using splenic NK cells from mice treated for 28 days with PQ (at 0.2, 1, and 5 mg/kg) were performed to determine whether PQ altered the function of NK cells. Given that PQ was expected to induce an immunosuppressive effect, it was hypothesized that a gene involved in cellular metal ion homeostasis, metallothionein-1 (MT-1), could play an important role in this outcome. This belief was based on the fact that MT1 encodes a protein responsible for zinc ion homeostasis, and that a reduction in free zinc ion levels impairs NK cell function. The results showed that PQ treatments led to increased MT expression in several organs (liver, kidneys, testes) and in splenocytes, caused a reduction of both free zinc ions in sera and in free intracellular zinc, and reduced the expression of GATA-3, a zinc-finger transcription factor important for maturation and activity of T-cells and NK cells. These results provide a basis for a new molecular mechanism to describe potential immunosuppressive effects of PQ in vivo.

Paraquat (PQ) causes selective degeneration of dopaminergic neurons in the substantia nigra pars compacta, reproducing an important pathological feature of Parkinson disease. Oxidative stress, c-Jun N-terminal kinase activation, and alpha-synuclein aggregation are each induced by PQ, but details of the cell death mechanisms involved remain unclear ... A Bak-dependent cell death mechanism /has been identified/ that is required for PQ-induced neurotoxicity. PQ induced morphological and biochemical features that were consistent with apoptosis, including dose-dependent cytochrome c release, with subsequent caspase-3 and poly(ADP-ribose) polymerase cleavage. Changes in nuclear morphology and loss of viability were blocked by cycloheximide, caspase inhibitor, and Bcl-2 overexpression. Evaluation of Bcl-2 family members showed that PQ induced high levels of Bak, Bid, BNip3, and Noxa. Small interfering RNA-mediated knockdown of BNip3, Noxa, and Bak each protected cells from PQ, but Bax knockdown did not. Finally, ... the sensitivity of Bak-deficient C57BL mice /was tested/ and found ... to be resistant to PQ treatments that depleted tyrosine hydroxylase immuno-positive neurons in the substantia nigra pars compacta of wild-type mice.

For more Mechanism of Action (Complete) data for Paraquat (10 total), please visit the HSDB record page.

Biological Half-Life · 5 件

Assessment of accumulation of paraquat in the lungs: 3 week inhalation study in rats (15 exposures). ...Lung concentrations in the high dose group peaked on about day 4 (4.71 mg paraquat/l), dropping to about half that concentration with continued dosing. Mean lung weights increased sharply after the fifth exposure in the high dose group to about 170% of controls. The elimination half-life was about 2 days.

... The concentration-time curve in 15 adult patients (not hemodialyzed) was best described by a bi-exponential curve, with the elimination half-lives of the early and late phase being 5 and 84 hours, respectively.

A biexponential body burden curve was observed in hamsters following intratracheal instillation of (14)C paraquat. Elimination rate was slow, beta value of 0.014 hr which corresponds to a half-life of 50 hr.

Half-life for absorption of radioactivity from lung of hamster administered dichloride salt intratracheally was 21 hr.

For more Biological Half-Life (Complete) data for Paraquat (6 total), please visit the HSDB record page.

Metabolism/Metabolites · 3 件

Paraquat was not metabolized by rats. After oral administration (gastric intubation) of single doses of paraquat dichloride or dimethylsulfate to Wistar strain male and female rats, most of the administered radioactivity (69-96%) was excreted in feces as unchanged paraquat. After subcutaneous injection of these compounds, unchanged paraquat appeared mostly in urine (73-96% of the administered radioactivity). Paraquat used in this study (radiochemical purity: 99-100%) was labeled with (14)C in the methyl groups. The doses used for gastric intubation ranged from 0.5 to 50 mg/kg and for subcutaneous injection, from 12.5 to 24 mg/kg. Most of the radioactivity was detected in feces within 2-3 days after dosing and in urine, within 1 day after dosing. Following oral administration of paraquat, up to 30% of the dose appeared in feces in a degraded form. This was due to the microbial degradation of paraquat in the gut. That microbial degradation of paraquat occurred in feces was shown in an in vitro experiment in which fecal homogenates were incubated with added paraquat for 24 hours. In that experiment, 40-50% of paraquat was destroyed. However, a similar experiment with sterilized fecal homogenates produced only minor loss (trace amounts) of added paraquat. /Paraquat dichloride/

Three Warren hens were given gelatin capsules containing (14)C-ring-labelled paraquat (purity, 99.7%; specific activity, 1.216 x 105 dpm/mg) at a daily dose of 4.52 mg of paraquat ion (0.247 mCi) for 10 days. ...Residues in tissues were generally unchanged paraquat. A small amount of a metabolite, 1-methyl-(4'-pyridyl), was found in the livers and kidneys.

An English white nanny goat was dosed with (14)C-ring-labelled paraquat (purity, 99.7%; specific activity, 2.28 x 104 dpm/ug) in the diet at a dose equivalent to 100 ug of paraquat ion/g of diet ... for 7 days. ... Residues in tissues were generally unchanged paraquat. In the liver, small amounts of 4-(1,2-dihydro-1-methyl-2-oxo-4-pyridyl)-1-methyl pyridinium ion and 1-methyl-4-(4'-pyridyl) pyridinium ion were found. The latter compound was also found in peritoneal fat.

MeSH Pharmacological ClassificationPesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.
Absorption, Distribution and Excretion · 5 件

In a fatal case of paraquat poisoning in a pregnant woman, who developed the typical symptoms and signs of paraquat poisoning and at postmortem had the typical lung pathology of paraquat poisoning, the fetal lungs were normal. ...However, ...the details /as reported/ of nine pregnant women who deliberately ingested paraquat, stated that paraquat in one case was concentrated 4-6 times in the fetus. In another of the cases, the amniotic fluid contained paraquat at twice the concentration of that in the maternal blood.

Paraquat was poorly absorbed after oral administration to rats, dogs and mice. Once absorbed, paraquat was rapidly distributed to most tissues but especially to lungs and kidneys. Tissues other than lungs did not retain paraquat.

In a dermal absorption study with healthy adult male volunteers, 0.3% of the applied (14)C-paraquat dichloride was absorbed through the intact skin (forearms, and back of the hands and lower legs) during the 24-hour exposure period. /Paraquat dichloride/

Absorbed paraquat is distributed via the bloodstream to practically all organs and tissues of the body, but no prolonged storage takes place in any tissue. The distribution of paraquat is best described by a three-compartment open model with input to and elimination from the central compartment ... The lung then selectively accumulates paraquat from the plasma, by an energy dependent process.

For more Absorption, Distribution and Excretion (Complete) data for Paraquat (28 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used as a contact herbicide for weed control in grass seed crops and orchards; a crop desiccant and defoliant on cotton and potato vines; harvest aid for soybeans; [HSDB] A quick-acting herbicide; [ACGIH]

Farming (Pesticides) [Category: Industry]

For paraquat (USEPA/OPP Pesticide Code: 061603) 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./

For paraquat dichloride (USEPA/OPP Pesticide Code: 061601) 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./ /Paraquat dichloride/

Desiccation of seed crops; noncrop and industrial weed control in bearing and nonbearing fruit orchards, shade trees, and ornamentals. Defoliation and desiccation of cotton. Harvest aid in soybeans, sugarcane, guar, and sunflowers, for pasture renovation, for use in "No-Till" or before planting or crop emergence, dormant alfalfa and clover, directed spray, and for killing potato vines. Eradication of weeds in rubber plantations, coffee plantations, and paddy bund. Talent /trade name/ postemergence in bananas, cocoa, coffee, coconuts, citrus, and sugarcane.

A widely used non-selective herbicide that kills all green plant tissue it contacts, especially grasses and weeds. Has been used to kill marijuana crops.

ImpuritiesThe only impurity permitted in paraquat is free 4,4'-bipyridyl at a maximum level of 0.25%.
U.S. Imports · 2 件

(1972) 3.39 X 10+9 g

(1975) 4.29 X 10+9 g (Dichloride)

Consumption Patterns100% for herbicide and desiccant use (1973)
Methods of Manufacturing · 4 件

Paraquat can be prepared by direct quaternization of 4,4'-bipyridyl with methyl chloride or dimethyl sulfate in water.

Paraquat is made by the reaction of 4,4'-bipyridyl with methyl chloride in water. The 4,4'-bipyridyl is made by the reaction of pyridine with sodium in liquid ammonia to give 4,4'-tetrahydrobipyridyl which is oxidized by air to give 4,4'-bipyridyl.

Preparation: ... By reacting aqueous methyl chloride with 4,4'bipyridyl, which is obtained by treating pyridine with sodium in liquid ammonia giving pyridyl radical which dimerizes to tetrahydro-4,4'-bipyridyl and this is oxidized by air, as ... dichloride ... /Dichloride/

Preparation: ... Produced by reaction of 4,4'-bipyridyl with dimethyl sulfate in water. /Paraquat dimethyl sulfate/

Formulations/Preparations · 5 件

Granular, solid, soluble concentrate.

Premix Partners: Asulam; Diquat Dibromide; Diruon; Monolinuron.

Paraquat Concentrate ES (Syngenta Crop Protection, LLC): Active ingredient: Paraquat dichloride 45.6%. /Paraquat dichloride/

Gramoxone Inteon (Syngenta Crop Protection, LLC): Active ingredient: Paraquat dichloride 30.1%. /Paraquat dichloride/

For more Formulations/Preparations (Complete) data for Paraquat (26 total), please visit the HSDB record page.

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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