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チオりん酸O,O-ジメチルO-(3,5,6-トリクロロ-2-ピリジニル)

Chlorpyrifos-methyl

HCID 21803
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
5598-13-0
標準SMILES
COP(=S)(OC)Oc1nc(Cl)c(Cl)cc1Cl
InChIKey
HRBKVYFZANMGRE-UHFFFAOYSA-N
分子式
C7H7Cl3NO3PS
平均分子量
322.5 g/mol
単同位体質量
320.894984

概要

Chlorpyrifos methyl appears as colorless crystals. Corrosive to copper, brass, iron, and tin plate. Used as an insecticide.

名称と識別子

優先名称
Chlorpyrifos-methyl
IUPAC
dimethoxy-sulfanylidene-[(3,5,6-trichloro-2-pyridinyl)oxy]-λ5-phosphane
現地名
チオりん酸O,O-ジメチルO-(3,5,6-トリクロロ-2-ピリジニル)
英語名
Chlorpyrifos-methyl
分子式
C7H7Cl3NO3PS
分子量
322.53

名称と別名

Chlorpyrifos-methyl5598-13-0ReldanTrichlormethylfosChloropyriphos-methylMethyl chlorpyrifosMethyl dursbanMethyl chlorpyriphosCHLORPYRIFOS METHYLNoltranZertellDowco 214
名称をさらに表示
チオりん酸O-3,5,6-トリクロロ-2-ピリジル-O,O-ジメチルメチルダーズバンメチルダースバンチオりん酸O,O-ジメチルO-(3,5,6-トリクロロ-2-ピリジニル)クロロピリフォス-メチルチオりん酸O,O-ジメチルO-(3,5,6-トリクロロ-2-ピリジル)クロルピリホスメチルレルダンO,O-ジメチル-3,5,6-トリクロロ-2-ピリジルホスホロチオアートクロルピリホスメチル標準品O,Oジメチル3,5,6トリクロロ2ピリジルホスホロチオアトチオりん酸O-3,5,6-トリクロロ-2-ピリジル-O,O-ジメチル (クロルピリホスメチル)CS_N-11460-250MG_クロルピリホスメチルクロルピリホス-メチルクロルピリホス-メチル STANDARDクロルピリホスメチル 溶液クロルピリホス-メチル Standard, 100 µg/mL in MeOHクロルピリホス・メチルダウレルダンO,O-ジメチル O-3,5,6-トリクロロピリジン-2-イル ホスホロチオアートm3196

物性

構造計算による物性

XLogP
4.3
極性表面積
72.7 Ų
水素結合供与体数
0
水素結合受容体数
5
回転可能結合数
4
重原子数
16
形式電荷
0
複雑度
278

実験および物理化学的性質

SpringerMaterials PropertiesFusion temperature
Pesticides · 6 件

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Organophosphate Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Acaricides, Insecticides

Pesticide

LogP · 2 件

log Kow = 4.31

3.99

OdorSlight mercaptan
Density1.64 at 23 °C
Color/Form · 2 件

White crystals

Amber solid cake

Solubility · 3 件

In water, 4.0 mg/L at 25 °C

In water, 4.76 mg/L at 20 °C

In acetone > 400; methanol 190; hexane 120 (all in g/kg at 20 °C)

Flash Point182 °C (Cleveland open cup)
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound

安全と法規制

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

GHS分類

GHS Classification · 6 件

Warning

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Danger

H302 (62.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P316, P321, P330, P333+P317, P342+P316, P362+P364, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Hazard Traits - Developmental Toxicity; Neurotoxicity

Commission Regulation No 844/2012

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

05/72/EC, Reg. (EU) 2018/1796, Reg. (EU) 2020/17, Reg. (EU) 84/2018, Reg. (EU) No 540/2011, Reg. (EU) No 762/2013

Chlorpyrifos methyl: Does not have an individual approval but may be used under an appropriate group standard

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 - Phosphorothioic acid, O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) ester: Environment tier I assessment
DOT LabelClass 9
Fire HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards Summary · 1 件

A skin irritant; [SAX] May cause skin sensitization; [eChemPortal: ESIS] In a two year feeding study with rats (highest dose level 1 mg/kg/day) no significant adverse gross or histopathological changes were observed as well as no relation to frequency of spontaneous tumors; Effects in a three generation feeding study with rats include inhibition of cholinesterase activity and decreased pup weights in the second and third generation; No significant effects were observed in fertility, gestation, viability, or lactation; No gross or histopathological changes were noted in third generation parental animals; No teratogenic effects observed in a study with rats; [Reference #2] 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] See Chlorpyrifos.

化学と産業

薬理情報

Mechanism of Action · 3 件

Non-systemic insecticide & acaracide with contact, stomach, & vapor action. Cholinesterase inhibitor.

The acetylcholinesterase, carboxylesterase, and cytochrome p450 monooxygenase activities of three strains of Oryzaephilus srinamensis (L.) were examined to better understand biochemical mechanisms of resistance. The three strains were VOS49 and VOSCM, selected for resistance to malathion and chlorpyrifos-methyl, respectively, and VOS48, a standard susceptible strain. Cross-resistance to malathion and chlorpyrifos-methyl was confirmed in VOS49 and VOSCM. Acetylcholinesterase activity was not correlated to resistance among these strains. VOS49 and VOSCM showed elevated levels of carboxylesterase activity based on p-nitrophenylacetate, alpha-naphthyl acetate, or beta-naphthyl acetate substrates. PAGE zymograms showed major differences in caboxylesterase isozyme banding among strains. VOSCM had one strongly staining isozyme band. A band having the same Rf-value was very faint in VOS48. The VOS49 carboxylesterase banding pattern was different from both VOSCM and VOS48. Cytochrome p450 monooxygenase activity was based on cytochrome p450 content, aldrin epoxidase activity, and oxidation of organophosphate insecticides, all elevated in resistant strains. The monooxygenase activity varied with insecticide substrate and resistant strain, suggesting specific cytochromes P450 may exist for different insecticides. The monooxygenase activity of the VOS49 strain was much higher with malathion than chlorpyrifos-methyl as substrates, whereas VOSCM monooxygenase activity was higher with malathion than chlorpyrifos-methyl as substrates. Results are discussed in the context of resistance mechanisms to organophosphate insecticides in O. surinamensis.

The mechanism of action is inhibition of acetylcholinesterase activity.

Biological Half-Life · 1 件

Two male Sprague-Dawley rats (approximately 200 g) were gavaged with (14)C-radiolabelled chlorpyrifos-methyl (purity >99%; 377 MBq/mmol; labelled at positions 2 and 6 on the pyridyl ring) at a dose level of 16 mg/kg bw (in corn oil). ... Levels of radioactivity indicated rapid clearance from blood, and the peak level seen at 5 hr had declined by 50% at approximately 9 hr following administration, suggesting an initial half-life of approximately 4 hr.

Metabolism/Metabolites · 6 件

Thyroid hormones are vital to a host of human physiological functions in both children and adults. Exposures to chemicals, including chlorpyrifos, have been found to modify thyroid signaling at environmentally relevant levels in animal studies. The aim of this study was to examine circulating T4 and TSH levels in relation to urinary concentrations of 3,5,6-trichloro-2-pyridinol (TCPY), a metabolite of the organophosphorus insecticides chlorpyrifos and chlorpyrifos-methyl, using data from individuals 12 years and older from the U.S. National Health and Nutrition Examination Surveys (NHANES). NHANES datasets from 1999 to 2000 and 2001-2002 were combined, and individuals with thyroid disease, those taking thyroid medications, and pregnant women were excluded (N = 3249). Multivariable linear regression models for relationships between log-transformed urinary TCPY and serum total T(4) or log (TSH) were constructed adjusting for important covariates. Models were stratified by sex and a categorical age variable (12-18, 18-40, 40-60, and >60 years). In male participants, an interquartile range (IQR) increase in urinary TCPY was associated with statistically significant increases in serum T(4) of 3.8% (95th CI 0.75 to 7.0) among those 12-18 years of age and 3.5% (95th CI 0.13 to 7.0) in the 18-40 year age group, relative to median T4 levels using unweighted models. An IQR increase in TCPY was also associated with decreases in TSH of 10.7% (-18.7-2.05) among men 18-40 years old and 20.0% (95th CI -28.9 to -9.86) among men >60 years old. Conversely, urinary TCPY was positively associated with TSH in females >60 years of age. /3,5,6-Trichloro-2-pyridinol (chlorpyrifos-methyl metabolite)/

関連反応

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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
M 3196
ent27520
dowco214
Reldan F
Chlorpyriphos-methylDursban methylTumarReldan 50 ECMethylchlorpyrifosPhosphorothioic acid, O,O-dimethyl O-(3,5,6-trichloro-2-pyridinyl) esterDTXSID6032352ENT 27520

データベース識別子

CAS
5598-13-0
PubChem CID
21803
DTXSID
DTXSID6032352
ChEMBL
CHEMBL1370646
ChEBI
CHEBI:34632
UNII
O49S38267J
EC Number
227-011-5
Nikkaji
J3.075I
Decomposition · 2 件

When heated to decomposition it emits very toxic fumes of /hydrogen chloride, nitrogen oxides, phosphorus oxides, & sodium oxides/.

DT50 = 3 days (pH 8)

Melting Point45.5-46.5 °C

物理化学的性質

融点
45.5 · 45.5-46.5°C
沸点
347.3 · 347.3±52.0 °C(Predicted)
比重(密度)
1.64 g/cm3 · 1.64 g/cm3(Temp: 23 °C)
闪点
100 °C · >100 °C
貯蔵温度
4 °C · APPROX 4°C
溶解性
Chloroform: Slightly Soluble
酸解離定数(Pka)
-5.59 · -5.59±0.10(Predicted)
外見
結晶性固体
色
アンバー
水溶解度
4 mg/L · 4mg/L(25℃)
Merck
13 · 13,2208
BRN
1541078 · 1541078
Henry's Law Constant
4.1 · 4.1×100 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
農業環境
InChI
1S/C7H7Cl3NO3PS/c1-12-15(16,13-2)14-7-5(9)3-4(8)6(10)11-7/h3H,1-2H3
InChIKey
HRBKVYFZANMGRE-UHFFFAOYSA-N
SMILES
COP(=S)(OC)Oc1nc(Cl)c(Cl)cc1Cl
CAS データベース
5598 · 5598-13-0(CAS DataBase Reference)
NISTの化学物質情報
o,o-Dimethyl-o-(3,5,6-trichloro-2-pyridyl)phosphorothioate(5598-13-0)
EPAの化学物質情報
Chlorpyrifos-methyl (5598-13-0)
化学的性質 · 1 件

化学的特性Chlorpyrifos-methyl is a general use organophosphate insecticide registered in 1985. It is used for the control of stored grain pests, weevils, moths, borers, beetles and mealworms, red fl our beetle, grain moth, for seed treatment. It is effective against rice stem borer, aphids, cutworms, plant and leaf hoppers, mole crickets, moths and stored grain pests. It is poorly soluble in water, moderately soluble in hexane and alcohols, and readily soluble in other organic solvents, such as acetone, benzene, and chloroform

Reactive GroupAmines, Phosphines, and Pyridines
Special Reports · 1 件

USEPA/Office of Prevention, Pesticides and Toxic Substances; Report of the Food Quality Protection Act (FQPA) Tolerance Reassessment Progress and Risk Management Decision (TRED) for Chlorpyrifos-methyl (January 2001). EPA issues a TRED for a pesticide that requires tolerance reassessment decisions, but does not require a reregistration eligibility decision at present because: the pesticide was initially registered after November 1, 1984, and by law is not included within the scope of the reregistration program; EPA completed a RED for the pesticide before FQPA was enacted on August 3, 1996; or the pesticide is not registered for use in the U.S. but tolerances are established that allow crops treated with the pesticide to be imported from other countries.[Available from, as of October 12, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]

FIFRA Requirements · 5 件

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl [O,-O,-dimethyl O-(3,5,6-trichloro-2-pyridyl)] phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities:[Table#6543]

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl (O,-O-dimethyl-O-(3,5,6-trichloro-2-pyridyl) phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities when present therein as a result of application to stored grains:[Table#6544]

Where a tolerance is established for triclopyr, chloropyrifos, and chlorpyrifos-methyl having the common metabolite 3,5,6-trichloro-2-pyridinol on the same raw agricultural commodity, the total amount of such residues shall not exceed the highest established tolerance for any of the pesticides having the metabolites.

Recent actions for Chlorpyrifos-methyl:[Table#6545]

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

Reactivity Profile · 1 件

A chlorinated organophosphate derivative. Organophosphates 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. It is incompatible with strong acids and bases.

Air and Water ReactionsHydrolyzed by strong acid and base.
Hazard Classes and Categories · 5 件

Acute Tox. 4 (62.2%)

Skin sensitisation - category 1

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Skin Sens. 1

安全と保護具

Fire FightingExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
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]

Storage ConditionsDo not contaminate water, food or feed by storage ... Store in a cool, dry location. Do not store in direct sunlight. Do not use or store near heat or open flame. /Storcide II Grain, Bin and Warehouse Insecticide/
Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Disposal Methods · 5 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Improper disposal of excess pesticide is a violation of Federal law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the hazardous waste representative at the EPA Regional Office for guidance. /Storcide II Grain, Bin and Warehouse Insecticide/

Rigid, non-refillable containers small enough to shake (i.e., with capacities equal to or less than 5 gallons). ... Do not reuse or refill this container. Offer for recycling, if available. Triple rinse or pressure rinse container (or equivalent) promptly after emptying ... Once container is rinsed, offer for recycling if available, or puncture and dispose of in a sanitary landfill or incineration, or if allowed by state and local authorities, by burning. If burned stay out of smoke. /Storcide II Grain, Bin and Warehouse Insecticide/

Rigid non-refillable containers that are too large to shake (i.e., with capacities greater than 5 gallons). ... Do not reuse or refill this container... Cleaning the container before final disposal is the responsibility of the person disposing of the container. Once container is rinsed, offer for recycling if available or puncture and dispose of in a sanitary landfill, or incineration, or if allowed by state and local authorities, by burning. If burned stay out of smoke. /Storcide II Grain, Bin and Warehouse Insecticide/

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

Preventive Measures · 5 件

Users and persons in treated areas should: Avoid inhalation of treated grain dust. Users should wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Users should remove clothing/PPE immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Users should remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Storcide II Grain, Bin and Warehouse Insecticide/

Do not apply this product in a way that will contact workers or other persons, either directly or through drift. Only protected handlers may be in the area during application. /Storcide II Grain, Bin and Warehouse Insecticide/

Do not apply directly to water, or to areas where surface water is present or to intertidal areas below the mean high water mark. Do not discharge directly or indirectly into surface waters. /Storcide II Grain, Bin and Warehouse Insecticide/

Wash hands, arms and face thoroughly with soap and water after handling and before eating or smoking. Routinely shower or bathe after work and wash all clothing with soap and hot water before reusing. /Storcide II Grain, Bin and Warehouse Insecticide/

For more Preventive Measures (Complete) data for CHLORPYRIFOS-METHYL (6 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Allowable Tolerances · 3 件

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl [O,-O,-dimethyl O-(3,5,6-trichloro-2-pyridyl)] phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities:[Table#6541]

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl (O,-O-dimethyl-O-(3,5,6-trichloro-2-pyridyl) phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities when present therein as a result of application to stored grains:[Table#6542]

Where a tolerance is established for triclopyr, chloropyrifos, and chlorpyrifos-methyl having the common metabolite 3,5,6-trichloro-2-pyridinol on the same raw agricultural commodity, the total amount of such residues shall not exceed the highest established tolerance for any of the pesticides having the metabolites.

Personal Protective Equipment (PPE) · 2 件

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Mixers, loaders, applicators and other handlers must wear: Long-sleeved shirt and long pants, chemical-resistant gloves, such as barrier laminate, butyl rubber, nitrile rubber, or Viton and protective eye equipment. In addition, applicators applying to empty grain bins must wear: A NIOSH-approved respirator with any N, R, P, or HE filter. /Storcide II Grain, Bin and Warehouse Insecticide/

毒性情報

Treatment · 1 件

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 3 件

Symptoms, lesions and changes in clinical chemistry and hematology were examined in goats orally dosed with dursban (150 mg/kg), reldan (150 mg/kg) and their mixture (300 mg/kg) in certain proportions. More rapid death and severe changes occurred in goats receiving reldan and dursban at 50% of the combined dose than either of the individual compounds.

At the dose of 600 mg/kg, which decreased hepatic nonprotein sulfhydryls (NPSH) by 90%, acetaminophen did not potentiate the effects of the organophosphorus insecticides methylchlorpyrifos, methylparathion or dichlorovos on esterases. On the other hand, depletion of hepatic NPSH by diethylmaleate increased the toxicities of the insecticides. While the reported inhibition of mixed function oxidase activity by acetaminophen may explain the lack of potentiation of methylchlorpyrifos and methylparathion which need to be converted to their oxygen analogs, its failure in potentiating the toxicity of dichlorvos, which does not require metabolic activation, suggests that other mechanisms are involved. Acetaminophen decreased NPSH only in the liver and, to a minor extent, in the kidney, while diethylmaleate caused significant depletion of NPSH in several tissues.

Human volunteer studies have been conducted by orally administering the pesticides deltamethrin (0.01 mg/kg/day) or pirimicarb (0.02 mg/kg/day) at the acceptable daily intake (ADI) together with chlorpyrifos-methyl (0.01 mg/kg/day), in order to investigate any potential interactions that may occur during dietary exposure. Deltamethrin and pirimicarb are metabolised in vivo by hydrolytic enzymes, which may be susceptible to inhibition by esterase-inhibiting compounds, such as chlorpyrifos-methyl. Urine samples were collected at time points up to at least 48 h post-exposure and metabolites were quantified. Urinary metabolite excretion data obtained from the mixed exposures were compared with data obtained from the same individuals given a dose of each individual pesticide on a separate occasion. Metabolite excretion profiles for both pesticides administered as a mixed dose with chlorpyrifos-methyl were qualitatively similar to those obtained for the individual doses. Peak excretion of deltamethrin and pirimicarb metabolites occurred at around 4h post-exposure for both the individual and the mixed exposure scenarios, and metabolite excretion was almost complete within 24h. No statistically significant differences were found between the individual and mixed doses for either metabolite excretion half-life or metabolite levels quantified in 24-h total urine collections. The data presented here indicate that no significant toxicokinetic interactions occur between either deltamethrin or pirimicarb and chlorpyrifos-methyl when orally administered together at the ADI.

Health Effects · 1 件

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

Ecotoxicity Values · 5 件

LD50; Species: Callipepla californica (California Quail) age 9-11 months; oral via capsule 334 mg/kg bw (95% confidence interval: 265-421 mg/kg bw)

LC50; Species: Anas platyrhynchos (Mallard Duck) age 9 days; diet >5620 ppm for 8 days

LC50; Species: Anas platyrhynchos (Mallard Duck) juvenile; diet <5000 ppm for 8 days (95% confidence interval: 2500-5000 ppm)

LD50; Species: Anas platyrhynchos (Mallard Duck) oral via capsule >1590 mg/kg

For more Ecotoxicity Values (Complete) data for CHLORPYRIFOS-METHYL (32 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 1190 to 8100(2) indicate that chlorpyrifos-methyl is expected to have low to no mobility in soil(SRC). Volatilization of chlorpyrifos-methyl from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-5 mm Hg(2), and water solubility, 4.0 mg/L(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Chlorpyrifos-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. In soil, chlorpyrifos-methyl undergoes microbial degradation to 3,5,6-trichloropyridin-2-ol, which is subsequently degraded to other organochlorine compounds and CO2(2). Chlorpyrifos-methyl is susceptible to aqueous hydrolysis (half-lives of 27 to 13 days at pH 4 through pH 9)(2), therefore abiotic hydrolysis in moist soil is expected to have some importance as a fate process(SRC). Abiotic degradation of chlorpyrifos-methyl can occur in salt marsh sediment through reaction with bisulfide and polysulfide ions at rates comparable to anaerobic microbial degradation(4). The degradation half-life (both abiotic and biotic) of chlorpyrifos-methyl was measured in soils incubated in a greenhouse at 23-26 °C(5); half-lives were 7, 6, 6, and 11 days in sandy, organic-rich orchard, agricultural, and volcanic area soils, respectively(5). A soil dissipation half-life range of 1.5 to 33 days has been reported(2,6) with an average dissipation half-life of 7 days(6).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 1190 to 8,100(2) indicate that chlorpyrifos-methyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.4X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 2.25X10-5 mm Hg(2), and water solubility, 4.0 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 28 and 207 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilation half-life from a model pond is about 15 years if adsorption is considered(5). According to a classification scheme(6), BCF values of 802(7) and 95(8) in fish, suggest bioconcentration in aquatic organisms is moderate to high(SRC). The hydrolysis half-life of chlorpyrifos-methyl in water at pHs 6.1 and 7.4 were 26 and 13 days, respectively, at 20 °C(9). Hydrolysis half-lives of 27 days (pH 4), 21 days (pH 7) and 13 days (pH 9) have also been reported(2). Aqueous photolysis maybe an important environmental fate process is indicated by half-lives of 1.8 days (June sunlight) and 3.8 days (December sunlight)(2); a half-life of 10 days was calculated(SRC) for sensitized photo-oxidation in natural waters containing humic acid sensitizers that are exposed to sunlight(10).

Food Survey Values · 5 件

As part of the FDA Total Diet Study since 1991, the mean concentration of chlorpyrifos-methyl was determined in the following market basket commodities(1).[Table#6546]

As part of the Belgian Total Diet Study between 1991-1993, the concentration range of chlorpyrifos-methyl was determined in the following market basket commodities (ppm): grape, washed (0.05-0.5); wheat flower, raw (0.05-0.5); nectarine, washed (0.05); pepper, steamed (0.1); bran, raw (0.05-0.5)(12). The mean concentration of chlorpyrifos-methyl in Egyptian market basket commodities (ppm) were as follows for the year 1995: tomato (0.07); apple (0.15); grape (0.13)(2).

Chlorpyrifos-methyl was detected in fresh and canned peaches sampled in Greece in 2000 with maximum concentration of 0.12 mg/kg(1).

A study was undertaken to assess the effects of storage intervals and of milling procedures on the dissipation of chlorpyrifos-methyl and pirimiphos-methyl residues in post-harvest-treated wheat grain and to obtain scientific data on the compliance of the processed products with safety requirements concerning baby foods. The insecticide formulations were applied on stored wheat at recommended rates (20 mL/ton). The initial concentration levels in whole grain were determined in samples taken 1 hr after treatment. The dissipation of residues and their distribution in different fractions of the milled grain were studied after various storage intervals, from 7 to 270 days after treatment. Samples of treated grain were milled in a fractionating laboratory mill and eight fractions - bran, semolina, three types of groats and three types of flour - were collected and analysed for pesticide residues. The residues were determined by an analytical method based on acetone extraction, graphitized carbon clean-up and GC-ECD, respectively, and GC-NPD determination of residues. The limits of determination of both pesticides were 0.005 mg/kg, which is high enough for enforcement of the European Commission Directive that established a maximum residue level of 0.01 mg/kg for any pesticide in cereal-based baby food. The results showed that the pesticides chlorpyrifos-methyl and pirimiphos-methyl applied post-harvest on wheat as grain protectants were distinguished by relatively low rates of degradation in the grain under practical storage conditions. Milling did not significantly reduce the bulk of the chemicals but resulted in the distribution of residues in various processed products. The main part of the insecticides deposited on the grain remained in the bran and partly in semolina fractions. After 270 days of treatment, the residues of chlorpyrifos-methyl were within the range 0.8-2.1 mg/kg and of pirimiphos-methyl - between 0.6 and 3.7 mg/kg in the various types of flour(1).

Chlorpyrifos-methyl residues in grain foods typical of the normal Kuwait diet. Residues in prepared dishes were as follows (mg/kg, % frequency): sandwiches 0-0.33, 60; fast food 0.01-0.09, 100; Arabic snacks 0.01-0.012, 33(1).

Adverse EffectsOther Poison - Organophosphate
Toxicity Summary · 2 件

IDENTIFICATION: Chlorpyrifos-methyl is an organophosphate pesticide used to control insects on fruits, vegetables and cereal plants. It is used to control insects in grain storage areas. This pesticide is a granular crystalline solid with a mercaptan odor. It is soluble in acetone, acetonitrile, benzene, carbon disulfide, carbon tetrachloride, chloroform, diethyl ether, ethanol, methanol, n-octanol and hexane. It is insoluble in water. HUMAN EXPOSURE: Fourteen male volunteers were divided into two treatment groups of 5 men each and a control group of four men. Chlorpyrifos-methyl was administered by gelatin capsule in a single daily dose for four weeks. Plasma and erythrocyte cholinesterase activities were not depressed at the levels tested. Hematology, blood chemistry, urinalysis, blood pressure, pulse and ophthalmology were not affected by the treatment. ANIMAL STUDIES/BIRDS: This pesticide was administered to groups of Sprague-Dawley CD strain rats in the diet for 104 weeks. There was no compound related effect on the incidence of spontaneous tumors. Chlorpyrifos-methyl administered orally to mice from day 7 through day 13 of gestation. Animals were sacrificed on day 18 and pups were removed by caesarean section. No significant difference was observed between control and treated groups concerning the number of implants and number of deaths. Body weights were lower in both males at the highest dose level. An increased incidence of cleft palate and a delay of ossification of the cervicovertebral body were observed at the high dose. When pregnant mice were dosed with a single oral dose on the seventh or eleventh day of pregnancy, there was no effect on mortality or body weights of the fetuses. A skeletal abnormality was observed (exencephalia, cleft palate, liberation of bone fragments of the cervicovertebral arch). Undiluted chlorpyrifos-methyl applied directly to the conjunctival sac of rabbits caused signs of irritation, which subsided after 24-48 hr. No corneal injury was noted. No significant skin reaction occurred when undiluted pesticide was applied to shaved and abraded skin of rabbits for prolonged periods. Chlorpyrifos-methyl was administered to rats in a three generation (two litters per generation) reproduction study. The pesticide was dosed orally. No treatment related effects were noted on behavior, survival and body weight gain or food consumption oberved in parental animals. Pup weights of the second litter, third generation were significantly less than control. There was no effect on sex ratio. In adults of the third generation, plasma cholinesterase activity decreased in both sexes at different dose levels. Mallard ducks, Bobwhite quail, Japanese quail were fed various doses of this pesticide for five days and observed for a further three days showed body weight and food consumption reduced for the Bobwhite and Japanese quail and at higher dose for the Mallard duck. Whole blood cholinesterase was inhibited. When 2,6-(14)C ring labeled chlorpyrifos-methyl was administered as a single dose to rats, radioactivity was readily absorbed and excreted. After 72 hr, 90-93% of the radioactivity was eliminated from the body. Urinary metabolites included 3,5,6-trichloro-2-pyridinol and unidentified activity at the origin by thin layer chromatography.

Average Daily Intake · 1 件

Between the years 1984-1986, the mean daily intake per unit body weight (ug/kg body wt/day) of chlorpyrifos-methyl was measured for the following age groups: 6-11 mo (0.0135), 2 yr (0.0323), 14-16 yr female (0.0118), 14-16 yr male (0.0158), 25-30 yr female (0.0101), 25-30 yr male (0.0116), 60-65 yr female (0.0092), and 60-65 yr male (0.0107)(1).

Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ Static bioassays were made to determine acute toxicity of chlorpyrifos-methyl, a wide spectrum organophosphorus insecticide and potential toxic pollutant of aquatic ecosystem, Guppy fish (Poecilia reticulata). Bioassays were made at a regulated temperature of 22+/-1 degrees C and were repeated three times. Lethal doses of the insecticides were determined using LC50 software programme of U.S. EPA based on Finney's Probit Analysis statistical method. The 96 hr LC50 value and 95% confidence limit of chlorpyrifos-methyl for Guppy was estimated as 1.79 (1.47-2.10) mg/L. The fish exposed to chlorpyrifos-methyl exhibited behavioral changes in the form of neurotoxin toxicity: less general activity than control group, loss of equilibrium, erratic swimming and staying motionless at a certain location generally at mid-water level for prolonged periods. The 1 mg/L (lowest) concentration had similar behavior (NOEC) with the control group.

Signs and Symptoms · 1 件

Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

Acute Toxicity LinkChemical: CHLORPYRIFOS-METHYL

法規制情報

FIFRA Requirements · 5 件

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl [O,-O,-dimethyl O-(3,5,6-trichloro-2-pyridyl)] phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities:[Table#6543]

Tolerances are established for the combined residues of the insecticide chlorpyrifos-methyl (O,-O-dimethyl-O-(3,5,6-trichloro-2-pyridyl) phosphorothioate and its metabolite (3,5,6-trichloro-2-pyridinol) in or on the following food commodities when present therein as a result of application to stored grains:[Table#6544]

Where a tolerance is established for triclopyr, chloropyrifos, and chlorpyrifos-methyl having the common metabolite 3,5,6-trichloro-2-pyridinol on the same raw agricultural commodity, the total amount of such residues shall not exceed the highest established tolerance for any of the pesticides having the metabolites.

Recent actions for Chlorpyrifos-methyl:[Table#6545]

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

安全データ

wgk
2
rtecs
TG0700000
ridadr
UN 3077
PRTR法
第2種指定化学物質
hs_code
29333990
risk_code
43-50/53-36-20/21/22-11
hazard_code
Xi;N,N,Xi,Xn,F
safety_code
36/37-60-61-36-26-16
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
5598-13-0(Hazardous Substances Data)

The urinary metabolites of chlorpyrifos-methyl were investigated by TLC ... . The primary metabolite was identified by co-chromatography as 3,5,6-trichloro-2-pyridinol (TCP). Additional non-mobile material was stated to be conjugated TCP. Metabolites were not quantified, and fecal metabolites were not investigated.

The oxidative desulfuration of the three phosphorothionate insecticides -- chlorpyrifos, chlorpyrifos-methyl, and leptophos--was studied in rat brain and liver. Hepatic microsomes demonstrated activities of 4-28 nmol/g/min, with male activity 2- to 4-fold higher than female activity. Very low desulfuration activity of all three compounds was observed in both microsomal and crude mitochondrial fractions from brain (3-27 pmol/g/min). There were no sex differences in the brain. Although the liver displayed 140- to 2100-fold greater activity than brain on a wet-weight basis, the brain desulfuration activities of these three compounds as well as those of some previously reported phosphorothionates generally correlate well with the toxicity and may be important in determining the overall acute toxicity levels of phosphorothionate insecticides.

Urinary metabolites ... were identified by gas-liquid chromatography, TLC and mass spectrometry as 3,5,6-trichloro-2-pyridinol (TCP) (13.8%), its glucuronide conjugate (68.6%) and the desmethyl metabolite O-methyl-O-(3,5,6-trichloropyridyl) phosphorothioate (17.8%). Feces were not analysed, as they contained less than 5% of the administered radiolabel.

A normal metabolic reaction with phosphorothioates is oxidative desulfuration or isomerization to give the oxon form, which is the more potent inhibitor of acetylcholinesterase. Chlorpyrifosmethyl oxon was not identified in the rat metabolism studies with chlorpyrifos-methyl.

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Absorption, Distribution and Excretion · 5 件

The dermal absorption of Reldan 22 (224 g/L chlorpyrifos-methyl, solvent based) was assessed in vitro using full-thickness male Fischer 344 rat skin. Single (10 uL) 28 hr applications of (14)C-labelled test material (undiluted or 1% aqueous dilution) were made to the epidermal surface of skin discs held in occluded flow diffusion cells at 31 °C. Receptor fluid (tissue culture medium containing 6% polyethylene glycol 20 oleyl ether) was collected at 2 h intervals. The solubility of chlorpyrifosmethyl in the receptor fluid was confirmed to be higher than the applied dose. For the concentrate, total recovery of radioactivity was high (92.27-99.32%). A lag time for penetration of 4-6 hr was observed; this was followed by linear absorption over the following 24 hr. For the spray strength dilution, total recovery of radioactivity was also high (95.05-100.89%). Distribution of radioactivity was consistent for all of the six replicates. A lag time for penetration of 8-10 hr was observed; this was followed by linear absorption over the remainder of the study. The linear absorption rate was calculated to be 10.4 ug/sq cm per hour for the concentrate and 0.039 ug/sq cm per hour for the 1% dilution. Dermal penetration was low for both formulation types.

Two male Sprague-Dawley rats (approximately 200 g) were gavaged with (14)C-radiolabelled chlorpyrifos-methyl (purity >99%; 377 MBq/mmol; labelled at positions 2 and 6 on the pyridyl ring) at a dose level of 16 mg/kg bw (in corn oil). Urine, feces and expired carbon dioxide were collected for up to 72 hr. Blood samples were taken from the tail at intervals throughout the study period. Radioactivity levels were determined by liquid scintillation counting or combustion analysis (fecal samples). Urinary metabolites were identified by thin-layer chromatography (TLC) and autoradiography. Peak blood radioactivity levels were reported at 5 hr, at which point the amount of test material in the blood was calculated to be approximately 3.0% (2.4-3.7%; absolute levels not given) of the administered dose. Levels of radioactivity indicated rapid clearance from blood, and the peak level seen at 5 hr had declined by 50% at approximately 9 hr following administration, suggesting an initial half-life of approximately 4 hr. Excretion of radioactivity was found to be primarily in the urine and largely within 24 hr of administration. Radioactivity levels in expired air were minimal. Residual tissue radioactivity levels at 72 hr were low in all tissues (<1 part per million [ppm]), but varied markedly between the two animals.

When (14)C-bound residues were fed to male rats for 24 hours, the animals eliminated 75% of the radioactivity in urine, 7% in expired air and 8% in faeces after 3 days, indicating that the bound residues were highly bioavailable. A further "bioavailable" amount (4%) was found in selected organs.

Tissue distributions of dichlorvos, an organophosphate, and chlorpyrifos-methyl, an organophosphorothioate, were determined. Tiny amounts of dichlorvos, 0.067 and 0.027 mg/L, were detected in the vitreous humor and cerebrospinal fluid, respectively. Although dichlorvos (0.082-8.99 mg/L or mg/kg) was detected in the thoracic aortic blood, thoracic inferior vena caval blood, pericardial fluid, bile, and spleen, it was strongly suggested that it had diffused postmortem from the stomach, which contained 879 mg, because no dichlorvos was detected in the other blood samples and tissues tested. Substantial amounts (0.615-4.15 mg/L) of chlorpyrifos-methyl were detected in all blood samples, and the order of its concentrations was as follows: pulmonary vessel blood > thoracic inferior vena caval blood > blood in the right cardiac chambers > blood in the left cardiac chambers = thoracic aortic blood > right femoral venous blood. The total amount of chlorpyrifos-methyl in the stomach was 612 mg. However, it was strongly suggested that virtually no chlorpyrifos-methyl diffused from the stomach into surrounding fluids and tissues postmortem because no chlorpyrifos-methyl was detected in the bile and little was found in the pericardial fluids. Neither compound was detected in the urine. In vitro experiments showed that dichlorvos (10 mg/L) almost disappeared from fresh (pH 7.4) and acidified (pH 6.2) blood samples within 24 and 72 hr, respectively. However, 53 and 77% of the original amount of dichlorvos in 0.05M phosphate buffers at pH 7.4 and 6.2 were detected 72 hr later. Chlorpyrifos-methyl (1 mg/L) was very stable in blood samples, regardless of the pH, during the 72-hr study period, but in the pH 7.4 and 6.2 phosphate buffers, approximately 80% of the original amount had degraded after 72 hr. ... When sodium fluoride was added to blood samples, dichlorvos degraded completely within 15 min, and chlorpyrifos-methyl became very unstable. When analyzing samples to detect organophosphorus chemicals, this common preservative should not be added to fluid specimens.

For more Absorption, Distribution and Excretion (Complete) data for CHLORPYRIFOS-METHYL (6 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

Used as insecticide, acaricide, and veterinary ectoparasiticide; [Merck Index] Used mainly to protect cereals (including storage); [HSDB] Used as insecticide for stored grains, rice, oil crops, and animal feed; [Reference #1]

Farming (Pesticides) [Category: Industry]

For chlorpyrifos-methyl (USEPA/OPP Pesticide Code: 059102) 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./

Insecticide

Control of Coleoptera, Diptera, Homoptera and Lepidoptera in cereals (including stored grains); and various foliar crop pests ... Industrial and public health uses include control of Muscidae and crawling insects; also employed in disease vector control programs (e.g. Anopheles spp., vectors of malaria).

... Used to control beetles, grain beetles, lesser grain borers, and red flour beetle.

Consumption Patterns · 1 件

Based on 1989 through 1998 usage information, the Agency estimates that chlorpyrifos methyl's total domestic usage averages approximately 80,000 pounds active ingredient for 267,497,000 bushels treated. About 80% of the total pounds of chlorpyrifos a.i. /methyl active ingredient/ is applied to wheat. Approximately 8% of all stored wheat, 5% of sorghum and 5% of barley are treated with chlorpyrifos methyl.

Methods of ManufacturingChlorpyrifos-methyl is produced by reaction of 3,5,6-trichloro-2-pyridinol with O,O-dimethyl phosphorochlorothioate.
Formulations/Preparations · 5 件

USEPA/OPP Pesticide Code 059102; Trade Names: ENT 27520, OMS 1155, DOWCO 214, Trichlormethylfos, Reldan.

Premix Partners: lambda-Cyhalothrin; Deltamethrin.

Emulsifiable concentrate, ultralow volume liquid, fogging concentrate.

Storcide II Grain, Bin and Warehouse Insecticide (Bayer Cropscience LP), Chlorpyrifos-methyl 21.6%, Deltamethrin 3.7%.

Reldan F Insecticidal Chemical (Dow Agrosciences LLC), Chlorpyrifos-methyl 97%.

Use Classification · 4 件

Pharmaceuticals

Acaricides, Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

INSECTICIDES

General Manufacturing InformationThe WHO Recommended Classification of Pesticides by Hazard identifies chlorpyrifos methyl (technical grade) as Class III: slightly hazardous; Main Use: insecticide.
応用分野 · 3 件

説明Chlorpyrifos-methyl is a general use organophosphate insecticide registered in 1985. It is used for the control of stored grain pests, weevils, moths, borers, beetles and mealworms, red flour beetle, and grain moth; for seed treatment; and for warehouse. It is effective against rice stem borer, aphids, cutworms, plant and leaf hoppers, mole crickets and some moths, and stored grain pests. It is poorly soluble in water, moderately soluble in hexane and alcohols, and readily soluble in other organic solvents such as acetone, benzene, and chloroform.

使用Chlorpyriphos-methyl is an derivative of Chlorpyrifos (C425300), an insecticide that acts on the nervous system of insects by inhibiting acetylcholinesterase.

一般的な説明Colorless crystals. Corrosive to copper, brass, iron, and tin plate. Used as an insecticide.

上流・下流製品情報

上流原料

亜鉛 (粉末)1-メチルイミダゾールベンジルトリエチルアンモニウムクロリド窒素クロルピリホス2,3,5,6-テトラクロロピリジンペンタクロロピリジンホスホロチオ酸O,O-ジメチルO-(3-メチル-4-ニトロフェニル)2,3,5-トリクロロ-6-ピリジノール五硫化リン塩化コバルト(II)チオりん酸水素O,O-ジメチル

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補足説明

定義ChEBI: An organic thiophosphate that is O,O-dimethyl hydrogen phosphorothioate in which the hydrogen of the hydroxy group has been replaced by a 3,5,6-trichloropyridin-2-yl group.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorpyrifos-methyl, which has a vapor pressure of 2.25X10-5 mm Hg at 25 °C(2) will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase chlorpyrifos-methyl is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6.6 hrs(SRC), calculated from its rate constant of 58X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase chlorpyrifos-methyl may be removed from the air by wet and dry deposition(SRC). Based on direct photolysis in aqueous solutions(2), chlorpyrifos-methyl is susceptible to direct photolysis in the atmosphere(SRC).

Chlorpyrifos-methyl is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.