化工社化工社 化学情報印刷レポート · 研究参考用
ジムピラート
チオりん酸=O-(2-イソプロピル-6-メチル-4-ピリミジニル)=O,O-ジエチル · バスジン · ジアジノン · ダイアジノン · スペクトラシド · チオりん酸O,O-ジエチルO-(2-イソプロピル-6-メチル-4-ピリミジニル) · チオりん酸O,O-ジエチル-O-(2-イソプロピル-6-メチル-4-ピリミジニル) · ネオシドール
識別子と物理属性
| CAS No. | 333-41-5 |
|---|---|
| 分子式 | C12H21N2O3PS |
| 平均分子量 | 304.35 g/mol |
| 単同位体質量 | 304.10105016 g/mol |
| SMILES | CCOP(=S)(OCC)Oc1cc(C)nc(C(C)C)n1 |
| InChIKey | FHIVAFMUCKRCQO-UHFFFAOYSA-N |
| PubChem CID | 3017 |
| ChEMBL | CHEMBL388560 |
| ChEBI | CHEBI:34682 |
| EC No. | 206-373-8 |
| DTXSID | DTXSID9020407 |
| 現地名 | ジムピラート |
化学・物理的性質
| XLogP | 3.8 |
|---|---|
| 極性表面積 | 85.6 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 6 |
| 回転可能結合数 | 7 |
| 重原子数 | 19 |
| 形式電荷 | 0 |
| 複雑度 | 307 |
| 物質分類 | Teratogens |
| SpringerMaterials Properties | Boiling point |
| 農薬 | PesticidesAcaricides, InsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Organophosphate InsecticidesPesticides -> Insecticides -> Organophosphorus insecticides -> Organothiophosphate insecticides -> Heterocyclic organothiophosphate insecticidesRepellents, Veterinary substances, Acaricides, Insecticides |
| LogP（分配係数） | log Kow = 3.813.11 |
| 臭い | Faint ester-like odor |
| 密度 | 1.117 at 68 °F (USCG, 1999) - Denser than waterwill sinkSpecific gravity: 1.116-1.118 at 20 °C/4 °CRelative density (water = 1): 1.11.12 |
| Color/Form | Colorless oilClear, colorless liquid |
| 溶解度 | less than 1 mg/mL at 75 °F (NTP, 1992)Completely miscible with common organic solvents, e.g. ethers, alcohols, benzene, toluene, hexane, cyclohexane, dichloromethane, acetone, petroleum oils.Freely soluble in ketonesSolubility in water: 0.004% at 20 °CSolubility in water: 60 mg/L at 20 °CIn water, 40 mg/L at 25 °CChloroform: Slightly Solubleやや溶ける。 0.004g/100mL |
| 引火点 | 82 to 105 °F (commercial solutions) (NTP, 1992)104.4 °C c.c.180 °F |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 沸点 | Decomposes >248 °F (NTP, 1992)BP: 125 °C at 1 mm Hg306°C |
| 融点 | >120°C (dec.) |
| 蒸気圧 | 1.2 x 10-2 Pa (25 °C) |
| 屈折率 | nD20 1.4978-1.4981 |
| 貯蔵条件 | APPROX 4°C |
| pKa（酸解離定数） | 1.21±0.30(Predicted) |
| 外観・状態 | Liquid |
| 色 | Light brown to brown |
| 由来生物 | rabbit |
| Merck | 13,3019 |
| BRN | 273790 |
| ヘンリー定数 | 4.6×101 mol/(m3Pa) at 25℃, Muir et al. (2004) |
| 安定性 | Moisture Sensitive |
| 主な用途 | 農業環境 |
| InChI | 1S/C12H21N2O3PS/c1-6-15-18(19,16-7-2)17-11-8-10(5)13-12(14-11)9(3)4/h8-9H,6-7H2,1-5H3 |
| InChIKey | FHIVAFMUCKRCQO-UHFFFAOYSA-N |
| SMILES | CCOP(=S)(OCC)Oc1cc(C)nc(n1)C(C)C |
| CAS データベース | 333-41-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Diazinone(333-41-5) |
| EPAの化学物質情報 | Diazinon (333-41-5) |
化学的特性
Diazinon is available as a colorless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agricultural and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, crops pests, and household pests like fl ies, fl eas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes, such as nitrogen oxides, phosphorous oxides, and sulfur oxides. It reacts with strong acids and alkalis with the possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classifi ed as an RUP. Depending on the type of formulation, diazinon is classifi ed as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)DangerH302 (72.8%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P273, P280, P301+P317, P302+P352, P308+P316, P317, P318, P319, P321, P330, P362+P364, P391, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 規制情報 | Hazard Traits - CarcinogenicityDevelopmental ToxicityEnvironmental toxNeurotoxicityCommission Regulation (EC) No 451/20002007/393Diazinon: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| その他の安全情報 | IMAP assessments - Phosphorothioic acid, O,O-diethyl O-[6-methyl-2-(1-methylethyl)-4-pyrimidinyl] ester: Human health tier I assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Not flammable. POISONOUS GASES ARE PRODUCED WHEN HEATED. Oxides of sulfur and of phosphorus are generated in fires. (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion if formulations contain flammable/explosive solvents. |
| 火災の可能性 | PRACTICALLY NONFLAMMABLE. |
| 健康有害性 | LIQUID: POISONOUS IF SWALLOWED. Irritating to skin and eyes. (USCG, 1999) |
| 有害性の概要 | Diazinon is the common name of an organophosphorus pesticide used to control pest insects in soil, on ornamental plants, and on fruit and vegetable field crops. It was formerly used as the active ingredient in household and garden products used to control pests such as flies, fleas, and cockroaches. Diazinon is a synthetic chemical, it does not occur naturally in the environment. Pure diazinon is colorless and practically odorless oil. Preparations used in agriculture and by exterminators contain 85-90% diazinon and appear as a pale to dark-brown liquid. Diazinon preparations sold in the past for home and garden use contained 1-5% diazinon in a liquid or as solid granules. Most diazinon used is in liquid form, but it is possible to be exposed to the solid form. Diazinon does not dissolve easily in water and does not burn easily.In animals, diazinon has a half-life of about 12 hours. Cows completely eliminate diazinon within two weeks of the last exposure. [http://ace.orst.edu/info/nptn] Classified as mildly or moderately toxic depending upon the formulation[EXTOXNET] Diazinon causes hepatic steatosis in high-dose feeding studies of rats. [Zimmerman, p. 394] 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] |
| 輸送番号・ガイド（DOT） | 2783 152 |
| 反応性グループ | Amines, Phosphines, and Pyridines |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | Eisler RDiazinon Hazards to Fish, Wildlife, and Invertebrates: A Synoptic ReviewGovt Reports Announcements & Index (GRA&I), Issue 24 (1986). Ecological and toxicological aspects were reviewed with special references to fishery and wildlife resources.Tafuri J, Roberts JOrganophosphate PoisoningAnn Emerg Med 16 (2): 193-202 (1987). Review of human insecticide diagnosis.Mullins DE et alDisposal of Concentrated Solution of Diazinon Using Organic Absorption and Chemical and Microbial DegradationPestic Sci 25 (3): 241-254 (1989).DHEW/NCIBioassay of Diazinon for Possible Carcinogenicity (1979) Technical Rpt Series No. 137 DHEW Pub No. (NIH) 79-1392USEPA/Office of Pesticide ProgramsReregistration Eligibility Decision Document - Diazinon (July 2006). 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 November 20, 2011: http://www.epa.gov/pesticides/reregistration/status.htm] |
| FIFRA 要件 | Tolerances are established for residues of the insecticide diazinon O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl)phosphorothioate in or on the following food commodities:[Table#1000]Tolerances with regional registrations, as defined in part 180.1(l), are established for residues of the insecticide diazinon O,O-diethyl O-(6-methyl-2-(1-methylethyl)-4-pyrimidinyl)phosphorothioate in or on the following food commodities: [Table#1001]EPA has concluded, after completing its assessment of the cumulative risks associated with exposures to all of the OPs /organophosphates/, that: (1) the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment ... are indeed eligible for reregistrationand (2) the pesticide tolerances covered by the IREDs and TREDs that were pending the results of the OP cumulative assessment ... meet the safety standard under Section 408(b)(2) of the FFDCA. Thus, with regard to the OPs, EPA has fulfilled its obligations as to FFDCA tolerance reassessment and FIFRA reregistration, other than product-specific reregistration.The Agency has completed its assessment of the occupational and ecological risks associated with the use of pesticides containing the active ingredient diazinon, as well as a diazinon-specific dietary risk assessment that has not considered the cumulative effects of organophosphates as a class. Based on a review of these data and public comments on the Agency's assessments for the active ingredient diazinon, EPA has sufficient information on the human health and ecological effects of diazinon to make interim decisions as part of the tolerance reassessment process under FFDCA and reregistration under FIFRA, as amended by FQPA. The Agency has determined that agricultural use of diazinon, based on currently approved labeling, pose occupational and ecological risks. However, the Agency believes that these risks can likely be acceptably mitigated through changes to pesticide labeling and formulations. Accordingly, the Agency has determined that products containing diazinon are eligible for reregistration provided that: (i) additional data that the Agency intends to require confirm this interim decision (ii) the risk mitigation measures outlined in this document are adopted and label amendments are made to reflect these measuresand (iii) cumulative risks considered for the organophosphates support a final reregistration eligibility decision.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Diazinon is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0238Pesticide type: Insecticide, fungicide (nematicide)Registration Standard Date: 12/25/88Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): diazinonData Call-in (DCI) Date(s): 10/19/92, 03/03/95, 10/13/95, 03/14/96AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. |
| 消火 | Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer immediately for medical attention. |
| 応急処置 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures) |
| 安全保管 | Provision to contain effluent from fire extinguishing. Separated from strong oxidants, strong acids, bases and food and feedstuffs. Keep in a well-ventilated room. Store in an area without drain or sewer access. |
| Firefighting Hazards | ... Vapors are heavier than air and will collect in low areas. Containers may explode in fire. ... |
| 暴露管理・個人防護 | Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baselineButylcholinesterase activity in serum or plasma = 60% of individual's baselineSample at end of shift[TLVs and BEIs]0.1 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| 消火手順 | Fire Extinguishing Media: dry chemical, foam, carbon dioxide.If material is on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water maybe ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol foam, dry chemical, or carbon dioxide. /Organophosphorous Pesticides, liquid, toxic/In Case of Fire: Use dry chemical, foam, or CO2 extinguishing media. Wear full protective clothing and self-contained breathing apparatus. Evacuate nonessential personnel from the area to prevent human exposure to fire, smoke, fumes, or products of combustion. Prevent use of contaminated building, area, and equipment until decontaminated. /Diazinon 50W/ |
| 保管条件 | Store in original container only in cool, dry, well-ventilated, secure area out of reach of children and animals. |
| 清掃方法 | In case of spill or leak: For small spills, sweep up keeping dust to a minimum, and place in a approved chemical container. Wash the spill area with water containing a strong detergent, absorb with pet litter or other absorbent material, sweep up, and place in a chemical container. Seal the container and handle in an approved manner. Flush the area with water to remove any residue. Do not allow wash water to contaminate water supplies. Wear appropriate PPE. /Diazinon 50W/Personal Protective Equipment (PPE). ... Handlers performing tasks such as cleaning equipment or spill cleanup for which engineering controls are not feasible must wear: coveralls over long-sleeved shirt and long pantschemical-resistant gloveschemical-resistant footwear plus sockschemical-resistant apron if exposed to the concentratea respirator with an organic vapor-removing cartridge with a prefilter approved for pesticides (MSHA/NIOSH approval number prefix TC-23C) or a canister approved for pesticides (MSHA/NIOSH approval number prefix TC-14G) or a NIOSH approved respirator with an organic vapor (OV) cartridge or canister with any R, P, or HE prefilter. /Diazinon 50W/Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commerical sorbents. /Organophosphorous Pesticides, liquid, toxic/Environmental considerations: Water spill: Use natural deep water barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorous Pesticides, liquid, toxic/Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. /Organophosphorous Pesticides, liquid, toxic/ |
| 非火災時の漏出対応 | Stop discharge if possible. Keep people away. Isolate and remove discharged material. Notify local health and pollution control agencies. (USCG, 1999) |
| 処分方法 | 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 qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.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.Pesticide Disposal: Pesticide wastes are toxic. Improper disposal is a violation of Federal law. To avoid harming aquatic organisms in rivers and other surface waters, do not pour spray mixture or rinse water into sanitary drains (for exampletoilets, floor drains, and sinks) or into storm water sewers (for examplestreet drains). If pesticide, spray mixture, or rinsate cannot be disposed of by use according to the label instructions, contact your State Pesticide or Environmental Control Agency or the Hazardous Waste representative of the nearest EPA Regional Office for guidance. /Diazinon 50W/Container Handling: Nonrefillable Container (flexible-bag-all weights): Nonrefillable container. Do not reuse or refill this container. Offer for recycling, if available. Once all water-soluble packets are used according to label instructions, dispose of empty outer bag in a sanitary landfill or by incineration, or, if allowed by State and local authorities, by burning. If burned, stay out of smoke.. /Diazinon 50W/For more Disposal Methods (Complete) data for DIAZINON (9 total), please visit the HSDB record page. |
| 漏出処分 | Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. |
| 毒性学的情報 | CDC-ATSDR Toxicological Profile |
| Treatment | 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. |
| 相互作用 | To investigate possible joint toxic effects of diazinon, propoxur and bisphenol A (BPA) on proliferation of /mouse/ RAW264.7 cells in vitro. Cytotoxicity was assessed by MTT assay. The median inhibiting concentration values (IC50) and 95% confidence interval (CI) of diazinon, propoxur and BPA individually and in mixture (mixed according to ratio of IC50) were established by weighted probit method. The types of toxic interaction of diazinon and BPA and propoxur and BPA were assessed by three methods commonly used for binary mixtures, which were Additional Index Method, Equivalent Effect Curve Method and Logistic Regression Method. After 24-hr expoxure, the IC50 and 95% CI of diazinon, propoxur and BPA to RAW264.7 cells were 194.1 microg/mL (173.4 microg/mL-217.4 microg/mL), 448.4 mg/L (358.2 microg/mL-573.2 microg/mL), and 37.5 microg/mL (35.3 microg/mL-39.9 microg/mL), respectively. Those of mixtures of diazinon and BPA and propoxur and BPA were 168.8 microg/mL (160.1 microg/mL-178.2 microg/mL) and 253.4 microg/mL (236.0-273.0 microg/mL). In the interaction assessment, three methods all demonstrated an antagonistic action of diazinon and BPA and an addition action of propoxur and BPA. ... |
| 標的器官 | Neurological (Nervous System)Eyes, respiratory system, central nervous system, cardiovascular system, blood cholinesterase |
| 健康影響 | 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. |
| 生態毒性値 | LD50Species: Anas platyrhynchos (Mallard duck) male, age 3-4 months oral 3.54 mg/kg (95% confidence limits: 2.37-5.27 mg/kg)Species: Anas platyrhynchos (Mallard ducklings) acute oral 3.5 mg/kgLC50Species: Coturnix (Quail) oral 167 ppm (99% active ingredient)Species: Coturnix (Quail) oral 101 ppm (48% active ingredient)For more Ecotoxicity Values (Complete) data for DIAZINON (100 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), a range of experimental Koc values of 191-1,842(2,3), indicates that diazinon is expected to have moderate-to-low mobility in soil(SRC). Volatilization of diazinon from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.17X10-7 atm-cu m/mole(4). Diazinon is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.0X10-5 mm Hg(5). Biodegradation is expected to be a major fate process in soils(SRC). Half-lives of <1, 2, and 5 weeks have been reported in non-sterile soils as compared to half-lives of 6, 6.5, and 12.5 weeks in sterile soils(6,7)at 7.5 and 20 °C, dissipation was approximately 65-95% in non-sterile soil and only 20-25% in sterile soil over 120 days(8). Overall persistence in soils has been reported to be 3 to 14 weeks(9). Field dissipation half-lives are reported to range from 2.8 to 48 days with an average of 7 days(3). Laboratory studies in top soil and subsoil at 20 and 7.5 °C have reported soil half-lives of 7 to 25 days(10)disappearance of diazinon was a combined effect of biotic and abiotic hydrolysis with hydrolysis rates depending on pH (especially important in acidic organic soil)(11). Hydrolysis of diazinon was reported to be more rapid in soils than in water11% of diazinon applied to Poygan sand was degraded per day(11). Diazinon absorbs light at wavelengths >290 nm(12), and therefore is susceptible to direct photolysis(SRC). The percent photolysis (difference between samples exposed to light closely approximating that of sunlight and covered samples) in 24 hrs was reported to be 51% on moist soil surfaces and 44% on dry soil surfaces at 45 °C, and 36% in pH 7.0 buffer solutions at 25 °C(13). The photolysis rate constant of diazinon on soil at 25 °C is reported to be 0.151 per day(3) which corresponds to a half-life of 4.6 days(SRC). Soil degradation of diazinon involves oxidation to the phosphate (diazoxon)(5) and hydrolysis to 2-isopropyl-6-methyl-pyrimidinol(14).TERRESTRIAL FATE: ... Diazinon is relatively nonpersistent in soil. Most diazinon applied is lost from soil through chemical and biologic degradation within about 2 months of application. ... about 46% of diazinon added to neutral aqueous solution remained after 2 wks.TERRESTRIAL FATE: Degraded in soil to 10% in 3 weeksAQUATIC FATE: Based on a classification scheme(1), a range of Koc values of 191-1,842(2,3), indicates that diazinon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 1.17X10-7 atm-cu m/mole(5). According to a classification scheme(6), a range of BCFs from 3-200(7-11), suggests the potential for bioconcentration in aquatic organisms is low-to-moderate(SRC). Hydrolysis may be a significant fate process(SRC) with reported half-lives of 31 days (pH 5), 185 days (pH 7.4), and 136 days (pH 9) at 20 °C(12), 2-3 weeks in distilled water at pH 6 at room temperature(13), and 12 days (pH 5), 139 days (pH 7) and 77 days (pH 9) at 25 °C(3). Major products of hydrolysis were 2-isopropyl-4-methyl-6-hydroxypyrimidine and diethyl thiophosphoric acid or diethyl phosphoric acid(12). Photolysis is an important degradation process(SRC)36% of diazinon photolyzed in a pH 7 buffer solution exposed to light with wavelengths >290 nm in a period of 24 hrs(14). The photolysis rate constant in water at 25 °C is reported to be 0.136 per day(3) which corresponds to a half-life of 5.1 days(SRC). Diazinon disappeared more quickly from unsterilized natural water (12 weeks) than from unsterilized distilled or sterilized natural water (>16 weeks), suggesting that degradation is both biological and chemical in nature in natural waters(15). Using water samples from two nursery recycling ponds as inoculum at 22 °C, half-lives ranged from 34.4 to 76.6 days in non-sterile water and 69.5 to 134.4 days sterile water(16).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diazinon, which has a vapor pressure of 9.0X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase diazinon 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 1.8 hrs(SRC), calculated from its experimental rate constant of 2X10-10 cu cm/molecule-sec(3). Particulate-phase diazinon may be removed from the air by wet and dry deposition(SRC). Diazinon absorbs light in the environmental spectrum(4) and has the potential for direct photolysis in the atmosphere(SRC). The detection of diazinon in lake waters in Canada (arctic, sub-arctic and remote locations) at long distances (hundreds of kilometers) from known source areas indicates diazinon can undergo long range atmospheric transport(5). |
| 食品調査値 | As part of US Market basket surveys for Fiscal Year 1999(1), the mean level of diazinon residues found in food (in ppm) was reported as follows: beef steak, pan-cooked (0.0009)pork chop, pan-cooked (0.0008)lamb chop, pan-cooked (0.0055)hamburger, fast-food (0.0005)lasagna with meat (0.003)chicken potpie, frozen (0.0005)chicken nuggets, fast-food (0.001)chicken, fried fast-food (0.002)beef stroganoff (0.0018)tuna noodle casserole (0.0026)turkey, frozen meal (0.0007)cheeseburger, fast-food (0.0009)fish sandwich, fast-food (0.0013)frankfurter, fast-food (0.0007)egg/cheese/ham, fast-food (0.0005)taco or tostada, carry-out (0.0008)pepperoni pizza, carry-out (0.0023)beef chow mein, carry-out (0.0023)brown gravy, homemade (0.002)split peas with veg, ham (0.0002)(1).As part of US Market basket surveys for Fiscal Year 1999(1), the mean level of diazinon residues found in food (in ppm) was reported as follows: green peas, boiled (0.002)corn, boiled (0.0007)apple, red, raw (0.0012)peach, raw (0.003)pear, raw (0.001)strawberries, raw (0.0035)plums, raw (0.002)grapefruit (0.006)sweet cherries, raw (0.003)raisins, dried (0.0004)spinach, boiled (0.0013)collards, boiled (0.001)coleslaw with dressing (0.001)broccoli, boiled (0.0015)celery, raw (0.0339)cauliflower, boiled (0.01)green beans, boiled (0.001)green pepper, raw (0.026)winter squash, baked (0.0007)applesauce, strained/junior (0.003)pumpkin pie (0.001)peas, mature, dry, boiled (0.014)mixed nuts without peanuts (0.001)apricot, raw (0.0017)French fries, fast-food (0.0017)carrot, fresh, boiled (0.01)Brussel sprouts, boiled (0.0044)mushrooms, raw (0.0056)green peppers, stuffed (0.002)mushroom soup, canned (0.002)(1).As part of US Market basket surveys for Fiscal Year 1999(1), the mean level of diazinon residues found in food (in ppm) was reported as follows: popcorn, popped in oil (0.008)white bread (0.0025)white roll (0.002)cornbread, homemade(0.0007)biscuit, baked (0.0016)whole wheat bread (0.003)rye bread (0.003)blueberry muffin (0.004)saltine crackers (0.005)pancake from mix (0.003)egg noodles, boiled (0.001)fruit-flavored cereal (0.001)shredded wheat cereal(0.001)granola cereal (0.0011)sweet roll or Danish (0.003)chocolate chip cookies (0.004)cracked wheat bread (0.0025)bagel, plain (0.001)English muffin, toasted (0.009)graham crackers (0.001)butter-type crackers (0.006)cheese pizza, carry-out (0.0017)chocolate snack cake (0.0025)cake doughnuts with icing (0.003)brownies, commercial (0.0022)sugar cookies, commercial (0.004)teething biscuits (0.001)(1)..As part of the USFDA Total Diet Study in 1991, the maximum concentration of diazinon residues in domestic and imported apples was 0.02 and 0.8 ppm, respectively(1). Diazinon was detected in 6 of 153 produce samples (fruits and vegetables) collected in Santa Monica CA between Sept 2002 and Oct 2004 (quantification values or detection limits not reported). Diazinon concentrations of 2.1 to 5.5 ug/kg were detected in commercial fruit juices (apple, grape, orange and pineapple) collected from supermarkets in Madrid Spain(3). |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contactOral (L162)inhalation (L162)dermal (L162) |
| Milk Concentrations | As part of the US Market basket surveys for 1969-76, the mean level of diazinon found in milk was measured as follows(1): fluid milk, domestic (0.2% of 4638 samples, <0.0001 ppm). As part of the USFDA Total Diet Study during fiscal years 1985-91, the maximum concentration of diazinon residue in milk was 0.17 ppm(1).Two lactating goats were orally treated with (pyrimidine-14C)-diazinon (specific activity 9.7 uCi/mg) in gelatin capsules for four consecutive days at a dose level of 4.5 mg/kg per day, corresponding to a dietary exposure of 100 mg/kg of feed. During the observation period, an average 64.1% of the administered radioactivity was excreted with urine, 10.4% with the feces and 0.31% with the milk. A plateau of radioactivity in the milk was reached after 3 days of dosing at a mean level of 0.46 mg/kg diazinon equivalent. |
| 毒性の概要 | IDENTIFICATION: Diazinon is a clear colorless liquid with a faint ester-like odor. Diazinon is soluble in most organic solvents. It is stable in neutral media, but is slowly hydrolyzed in alkaline media and more rapidly in acid media. Diazinon is a contact organophosphorus insecticide with a wide range of insecticidal activity. It is also available in mixed formulations with other insecticides. Another major use is as a drug in veterinary medicine. HUMAN EXPOSURE: Environmental levels of diazinon are generally low. The routes of exposure for the general population are inhalational and dietary. Exposure through water is negligible. Occupational exposure is primarily dermal. Several cases of accidental or suicidal poisoning by diazinon hae been reported, some of which were fatal. In some of these the cholinergic syndrome may have been more severe than expected because of the presence of highly toxic impurities such as TEPP. In certain cases, acute reversible pancreatitis was associated with a severe cholinergic syndrome. Reported cases of poisoning after occupational exposure have always been associated with the presence of impurities. ANIMAL STUDIES: The acute oral, dermal and inhalational toxicity is low. Short-term and long-term studies in mice, rats, rabbits, dogs and monkeys have shown that the only effect of concern is dose-related inhibition of acetyl cholinesterase activity. Diazinon is slightly irritant to rabbit skin but not to the eye. Diazinon is not a dermal sensitizer. Reproductive and developmental studies have revealed no evidence of embryotoxic or teratogenic potential. There was no effect on reproductive performance at dose levels that were not toxic to the parent animals. Mutagenicity studies with various end-points in vivo and in vitro gave no evidence of a mutagenic potential. There is no evidence of carinogenicity in rats or mice. In the dog and guinea-pig, diazinon has been reported to cause acute pancreatitisthis is considered to be a species-specific effect. Diazinon may be absorbed from the gastrointestinal tract, through the intact skin and following inhalation. Diazinon is oxidized by microsomal enzymes to cholinesterase inhibiting metabolites such as diazoxon, hydroxydiazoxon and hydroxydiazinon.Diazinon 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. |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| 清浄水法要件 | Diazinon is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance. |
| 州飲料水ガイドライン | (AZ) ARIZONA 0.63 ug/l(CA) CALIFORNIA 6 ug/l(FL) FLORIDA 6.3 ug/l |
| 連邦飲料水ガイドライン | EPA 1 ug/L |
| 職業暴露区分（OEB） | D |
| 職業暴露限界（OEL） | TWA: 0.1 mg/m3 [skin] |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TF3325000 |
| 輸送番号（UN） | UN 2783/2810 |
| 毒性 | LD50 in male, female rats (mg/kg): 250, 285 orally (Gaines) |
| PRTR法 | 第1種指定化学物質 |
| 税関コード | 29335990 |
| 危険文句（R） | 22-50/53-36-20/21/22-11-51/53 |
| 化審法 | 一般化学物質 |
| 安衛法 | 57,57-2 |
| 消防法 | 危-4-3-III |
| 危険表示 | XnN,N,Xn,F |
| 安全措置（S） | 24/25-60-61-36-26-16-36/37 |
| 危険等級 | 6.1(b)Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Flam. Liq. 2 |
| 包装等級 | III |
| 毒劇物取締法 | III |
| 環境リスク評価 | ダイアジノン(333-41-5) |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 333-41-5(Hazardous Substances Data) |
用途
解説
ダイアジノン，有機リン殺虫剤の一種。スイスのガイギー社が1952年に開発した有機リン酸エステル系殺虫剤の一種。各種の衛生・農業害虫に対し使用。一般名，商品名ともダイアジノンである。ニカメイチュウ，ウンカ，ヨコバイなどのイネ害虫をはじめ広範囲の害虫に対して殺虫力を示し，哺乳類に対する急性毒性は，50％致死量LD50＝250mg/kg(ラット(雄)，経口)とかなり低い。沸点 83～84℃の無色液体。水に難溶，有機溶媒によく溶ける。果樹，蔬菜の各種害虫，はえ，蚊，ごきぶりなどの衛生害虫の防除に用いられる。接触毒，食毒のほかガス毒として作用。茎葉散布，土壌施用剤，水面施用剤，燻煙剤など用途が広い。
用途
農薬(殺虫剤) (NITE CHRIP)
説明
Diazinon is a non-systemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon functions as the inhibitor of acetylcholinesterase (AChE), which breaks down the neurotransmitter acetylcholine (ACh) into [choline] and an acetate group. The inhibition of the AChE causes an abnormal accumulation of ACh in the synaptic cleft. However, recent studies have shown that diazinon and other kinds of organophosphate can cause neural toxicity through causing oxidative stress in the neural cells.
使用
Diazinon is used to control a wide range of sucking and chewing insects and mites in a very wide range of crops and is also used as a veterinary ectoparasiticide.
一般的な説明
Diazinon is available in the form of a colourless or dark brown liquid. It is sparingly soluble in water but very soluble in petroleum ether, alcohol, and benzene. Diazinon is used for the control of a variety of agriculture and household pests. These include pests in soil, on ornamental plants, fruit, vegetable, and crops and household pests like flies, fleas, and cockroaches. Diazinon undergoes decomposition on heating above 120°C and produces toxic fumes such as nitrogen oxides, phosphorus oxides, and sulphur oxides. It reacts with strong acids and alkalis with possible formation of highly toxic tetra ethyl thiopyrophosphates. Diazinon is classified as a RUP. Depending on the type of formulation, diazinon is classified as toxicity class II, meaning moderately toxic, or toxicity class III, meaning slightly toxic.
使用用途
ダイアジノンは、害虫の防除を目的に使用されています。使用方法や使用時期のバリエーションが多く、栽培体系や害虫の特徴に合わせて使用できることが特徴です。 特に効果を感じられる害虫は、ケラやネキリムシ類、コガネムシ類の幼虫など土の中に潜んでいる害虫です。 ダイアジノンを土壌に散布し、鍬やトラクターなどで耕うんし土と混ぜます。土壌でガス化するため、直接害虫と接触した部分だけではなく、広範囲に害虫に対しての殺虫力を示します。 また、他の有機リン酸エステル系殺虫剤などによって薬害を生じやすい農作物においても、薬害が発生しにくいです。そのため、イチゴやニンジン、ダイコン、トウモロコシ、トマト、ウリ類など多くの農作物において防虫、殺虫剤として使用されます。