化工社化工社 化学情報印刷レポート · 研究参考用
ジチオりん酸O,O-ジメチルS-(N-メチルカルバモイルメチル)
ホスチオン · ジチオりん酸O,O-ジメチルS-[2-(メチルアミノ)-2-オキソエチル] · ペルフェクチオン · ホスチオンMM · ホスファミド · フェルケチオン · ジメトアート · シゴン
識別子と物理属性
| CAS No. | 60-51-5 |
|---|---|
| 分子式 | C5H12NO3PS2 |
| 平均分子量 | 229.3 g/mol |
| 単同位体質量 | 228.99962187 g/mol |
| SMILES | CNC(=O)CSP(=S)(OC)OC |
| InChIKey | MCWXGJITAZMZEV-UHFFFAOYSA-N |
| PubChem CID | 3082 |
| ChEMBL | CHEMBL1569524 |
| ChEBI | CHEBI:34714 |
| EC No. | 200-480-3 |
| DTXSID | DTXSID7020479 |
| 現地名 | ジチオりん酸O,O-ジメチルS-(N-メチルカルバモイルメチル) |
化学・物理的性質
| XLogP | 0.8 |
|---|---|
| 極性表面積 | 105 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 5 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 191 |
| 物質分類 | Teratogens |
| SpringerMaterials Properties | 31P nuclear magnetic resonance spectrum |
| 農薬 | PesticidesPesticide -> EPA IRISAcaricides, InsecticidesActive substance -> EU Pesticides database: Not approvedPesticides -> Organophosphate InsecticidesEnvironmental transformation -> Pesticides (parent, predecessor) |
| LogP（分配係数） | log Kow = 0.780.5/0.8 |
| 臭い | CAMPHOR-LIKE ODORMercaptan odor |
| 密度 | 1.277 at 149 °F (EPA, 1998) - Denser than waterwill sink1.277 at 65 °C1.3 g/cm³1.277 @ 65°C1.281 |
| Color/Form | White crystalline solidColorless crystals (Tech., white solid pellets) |
| 溶解度 | 1 to 10 mg/mL at 75 °F (NTP, 1992)Readily soluble in most organic solvents, e.g. alcohols, ketones, benzene, toluene, chloroform, dichloromethane >300 g/kg at 20 °Ccarbon tetrachloride, saturated hydrocarbons, n-octanol >50 g/kg at 20 °CMore than 5000 mg/L water at 20 plus or minus 1.5 °CIn water, 2.5X10+4 m/L at 25 °CSOL IN CYCLOHEXANONELOW SOLUBILITY IN XYLENE, HEXANESolubility in water, g/100ml at 21 °C: 2.5Chloroform: Slightly Soluble,DMSO: Slightly Solubleやや溶ける。 2.5g/100mL |
| Corrosivity | Slightly corrosive to iron |
| 引火点 | 124 °F (EPA, 1998)107 °C (closed cup)107 °C c.c. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 沸点 | 243 °F at 0.1 mmHg (NTP, 1992)107 °C at 0.05 mm Hgat 0.01kPa: 117 °C243 °F at 0.1 mmHg107°C (0.05 torr) |
| 融点 | 52-52.5°C |
| 蒸気圧 | 2.5 x 10-4 Pa (25 °C) |
| 屈折率 | nD65 1.5334 |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 14.40±0.46(Predicted) |
| 色 | White to off-white |
| 由来生物 | mouse |
| Merck | 13,3246 |
| BRN | 1785339 |
| ヘンリー定数 | 4.1×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| 主な用途 | 農業環境 |
| InChI | 1S/C5H12NO3PS2/c1-6-5(7)4-12-10(11,8-2)9-3/h4H2,1-3H3,(H,6,7) |
| InChIKey | MCWXGJITAZMZEV-UHFFFAOYSA-N |
| SMILES | CNC(CSP(OC)(OC)=S)=O |
| LogP（分配係数） | 0.780 |
| CAS データベース | 60-51-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Dimethoate(60-51-5) |
| EPAの化学物質情報 | Dimethoate (60-51-5) |
化学的特性
Dimethoate is a gray-white crystalline solid at room temperature. It is sparingly soluble in water, soluble in methanol and cyclohexane, but very soluble in chloroform, benzene. It has been classifi ed by the US EPA under GUP. Dimethoate is used extensively for the control of crop pests, such as mites, aphids, thrips, plant-hoppers, white-fl ies, and a wide range of other insects that damage, crops, fruits, vegetables, and ornamental plants. Dimethoate is also used for the control of cattle grubs that infect livestock. Thermal decomposition of dimethoate is highly hazardous owing to the release of fumes of dimethylsulfi de, methyl mercaptane, carbon monoxide, carbon dioxide, phosphorus pentoxide, and nitrogenoxides.
安全性と法規制
| GHS 分類 | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)H302 (97.3%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Hazard Traits - Developmental ToxicityEnvironmental toxNeurotoxicityCommission Regulation No 844/2012Dimethoate is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)07/25/EC, Reg. (EU) 2018/917, Reg. (EU) 2019/1090, Reg. (EU) 2019/707, Reg. (EU) No 540/2011Dimethoate: 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 - Phosphorodithioic acid, O,O-dimethyl S-[2-(methylamino)-2-oxoethyl] ester: Environment tier I assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | As with other organophosphorus pesticides, container may explode in heat of fire. The temperature of storage should not exceed 70-80F. Keep away from sources of heat, flames, or spark-generating equipment. Unstable in alkaline solution. Hydrolyzed by aqueous alkali. Stable in aqueous solutions. The compound is stable for 2 years under environmental conditions if stored in undamaged, original containers. (EPA, 1998)Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | Very toxicthe probable oral lethal dose in humans is between 50-500 mg/kg, or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. Dimethoate is a cholinesterase inhibitor, meaning it affects the central nervous system. Death is due to respiratory arrest arising from failure of respiratory center, paralysis of respiratory muscles, intense bronchoconstriction or all three. (EPA, 1998) |
| 有害性の概要 | An erythema-multiforme-like contact dermatitis has been reported[Kanerva, p. 1783] A cholinesterase inhibitor that can be absorbed through skinMay have adverse effects on human reproduction, based on animal studies[ICSC] Has the highest reported incidence of poisonings (none life-threatening) of the organophosphates used in residential applicationsNo evidence of delayed neurotoxicity in hens[Reference #2] Delayed neuropathy has been very rarely reported in humans, and seems to result from severe poisoningNot likely to cause delayed neuropathy under normal levels of exposureMay cause an intermediate syndrome that can be life threateningSymptoms developing 1-4 days following exposure include weakness of proximal limb muscles and neck flexors and respiratory distressFour cases have been reported and involved ingestion of large amounts[EFSA] 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 Omethoate. |
| 反応性グループ | Amides and Imides |
| EC 分類 | Symbol: XnR: 21/22S: (2)-36/37 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | US Dept of AgricultureThe Biologic and Economic Assessment of Dimethoate. A Report of the Dimethoate Assessment Team to the Rebuttable Presumption Against Registration of Dimethoate. Tech Bull USDA 1663: 322 pp. (1981). A review with 425 references on the uses of dimethoate. Benefit analyses are discussed and other alternatives are /presented/.DHEW/NCIBioassay of Dimethoate for Possible Carcinogenicity (1977) Technical Rpt Series No. 4 DHEW Pub No. (NIH) 77-804WHOEnviron Health Criteria Number 90: Dimethoate (1989).FAO/WHOJMPR Pesticide residues in food, Dimethoate (addendum) (2003). Available from: http://www.inchem.org/documents/jmpr/jmpmono/v92pr09.htm as of January 8, 2007. This report discusses background information used to develop an ADI for dimethoate.USEPA/Office of Pesticide ProgramsInterim Reregistration Eligibility Decision (IRED) for Dimethoate. EPA issues an IRED for a pesticide that is undergoing reregistration, requires a reregistration eligibility decision, and also needs a cumulative assessment under FQPA. The IRED, issued after EPA completes the individual pesticide\'s aggregate risk assessment, may include taking risk reduction measures -- for example, reducing risks to workers or eliminating uses that the registrant no longer wishes to maintain -- to gain the benefits of these changes before the final RED can be issued following the Agency\'s consideration of cumulative risks.[Available from, as of February 28, 2007: http://www.epa.gov/pesticides/reregistration/status.htm] |
| RCRA 要件 | P044As stipulated in 40 CFR 261.33, when dimethoate, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). |
| FIFRA 要件 | Tolerances are established for total residues of the insecticide dimethoate (O,O-dimethyl S-(N-methylcarbamoylmethyl) phosphorodithioate) including its oxygen analog (O,O-dimethyl S-(N- methylcarbamoylmethyl) phosphorothioate) in or on the following food commodities: [Table#3275]Tolerances with regional registration, as defined in §180.1(n), are established for total residues of dimethoate including its oxygen analog in or on the following food commodities: [Table#3276]EPA has completed its assessment of the cumulative risks from the organophosphate (OP) class of pesticides as required by the Food Quality Protection Act of 1996. In addition, the individual OPs have also been subject to review through the individual-chemical review process. The Agency's review of individual OPs has resulted in the issuance of Interim Reregistration Eligibility Decisions (IREDs) for 22 OPs /including dimethoate/, interim Tolerance Reassessment and Risk Management Decisions (TREDs) for 8 OPs, and a Reregistration Eligibility Decision (RED) for one OP, malathion. ... EPA has concluded, after completing its assessment of the cumulative risks associated with exposures to all of the OPs, that: (1) the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) 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.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. Dimethoate 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: 0088Pesticide type: insecticide (acaricide)Registration Standard Date: 04/11/83Case 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): DimethoateData Call-in (DCI) Date(s): 06/28/91, 10/13/95, 02/09/96AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. |
| 消火 | This material is an organophosphate insecticide. Procedures for organophosphorus pesticides are as follows. Dike fire control water for later disposal, do not scatter the material. Wear positive pressure breathing apparatus and protective clothing. Fight fire from maximum distance.Use water spray, powder, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Rest. Refer for medical attention . |
| 応急処置 | Note: Dimethoate is a cholinesterase inhibitor. |
| 安全保管 | Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room. |
| 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] |
| 消火手順 | Dry chemicals, carbon dioxide for small fires. Water spray or foam for larger fires.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, liquid, NOS/If material on fire or involved in fire: Use water in flooding quantities as fog. Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use "alcohol" foam, carbon dioxide or dry chemical. /Organophosphorus pesticides, solid, NOS/ |
| 保管条件 | The biological activity remains practically unvaried for 2 yr under environmental conditions, provided stored in unopened and undamaged original containers, in shaded, cool, well-aired places, inaccessible to animals & unauthorized persons. Recommended temp < 25 °C/77 °F. Crystals may form in formulations stored at < 32 °F/0 °C. Stable a minimum of 1 yr at < 25-30 °C/77-86 °F. Stack containers to permit air circulation at bottom & inside of piles. Do not contaminate food, feed products.Liquid formulations must be stored above 45 °F....Must be stored in its sealed original containers, in well-aired, fresh & dry storehouses or in shaded & possibly well-aired places. It is recommended that the product's temp...not exceed 25-30 °C, & keep...away from sources of heat, free flames or spark-generating equipment. Containers must be stacked in such a way as to permit free circulation of air...at bottom & inside of piles. Storage areas must be located at suitable distance from inhabited buildings, animal shelters, & food storesmoreover, they must be inaccessible to unauthorized persons, children, & domestic animals. /Dimethoate/ |
| 清掃方法 | Use of granular, activated carbon in the adsorption of pesticides from wastewater is presented. Dimethoate was one of the compounds studied.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 commercial sorbents. /Organophosphorus pesticides, liquid and solid, NOS/Environmental considerations- water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses. /Organophosphorus pesticides, liquid and solid, NOS/Environmental considerations- air spill: Apply water spray or mist to knock down vapors. /Organophosphorus pesticides, liquid and solid, NOS/ |
| 非火災時の漏出対応 | Dimethoate is an organophosphate insecticide. Precautions for organophosphorus pesticides include the following. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled materialstop leak if you can do so without risk. Use water spray to reduce vapors. |
| 処分方法 | Do not contaminate water, food or feed by storage and disposal. PESTICIDE DISPOSAL: ... 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 nearest EPA Regional Office for guidance. CONTAINER DISPOSAL: Plastc: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or incineration, or if allowed by state and local authorities, by vurning. If burned, stay out of smoke. /Def-Fend E-267/Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P044, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Potential candidate for rotary kiln incineration with a temperature range of 820-1600 °C with residence times for liquids and gases, secondssolids, hours. Also, a potential candidate for fluidized bed incineration with a temperature range of 450 to 980 °C with residence times for liquids and gases, secondssolids longer. /From table/This compound should be susceptible to removal from wastewater by air stripping.For more Disposal Methods (Complete) data for DIMETHOATE (6 total), please visit the HSDB record page. |
| 漏出処分 | Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus. |
| Preventive Measures | Note to Physician: For all exposures administer atropine and 2-PAM as an antidote for acetylcholinesterase inhibition.Avoid eye, skin, clothing contact. Do not breathe dust. Use with adequate ventilation. ... Wash thoroughly after handling.If in eyes: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for further treatment advice. If on skin or clothing: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for further treatment advice. /De-Fend E-267/Users should: wash hands before eating, drinking, chewing gum, using tobacco, or using the toiletremove clothing immediately if pesticide gets inside, then wash thoroughly an put on clean clothingand remove personal protective equipment immediately after handling this productwash the outside of gloves before removingas soon as possible, wash thoroughly and change into clean clothing. /De-Fend E-267/For more Preventive Measures (Complete) data for DIMETHOATE (15 total), please visit the HSDB record page. |
| 体内負荷 | In a Russian study, dimethoate residues were detected in fish for 30 day after application at 1.5 kg/hectare. Residue accumulation occurred in the kidneys at levels as high as 159 mg/kg. |
| 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 | The effects of various classes of insecticides were studied on N-demethylation of dimethylnitrosamine (DMN) by mouse liver enzymes. Organochlorine insecticides increased the activities of dimethylnitrosamine demethylases I and II. Dimethoate, an organophosphorus cmpd, was the only insecticide tested to inhibit the N-demethylation of dimethylnitrosamine, with more pronounced effect on dimethylnitrosamine demethylase I.Organophosphates are usually found in the environment with other pesticides and with pollutants of industrial origin can cause combined exposure involving unknown interactions between the agents. In this study, female Wistar rats were given 1/25 LD50 of dimethoate by gavage, combined with the same LD50 fractions of propoxur and cypermethrin or with arsenic (6.66 mg/kg). The doses were given from day 5 to 15 of pregnancy, or that plus for the 4 weeks of lactation, or that plus 8 weeks for the male offspring after weaning. Control rats received distilled water. Electrophysiological recording was done when the male offspring reached 12 weeks of age. Spontaneous activity and evoked potentials from the somatosensory, visual and auditory cortexand conduction velocity and absolute and relative refractory periods of the tail nerve were measured. The general trend was a shift of the spontaneous cortical activity to higher frequencies and increase in the evoked potential latency. The results showed that combined exposure to several environmental toxicants could be more harmful than the effects of each substance alone ...Carbon disulfide pretreatment potentiated the anticholinesterase action of parathion and EPN, but suppressed that of dimethoate and diazinon. Carbon disulfide had no significant effect or a slightly suppressive effect on the other compounds. Some of these effects were contrasted with the repeated alteration of the toxicity following phenobarbital pretreatment. |
| 標的器官 | Nervous |
| 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 | LC50 Lepomis macrochirus (Bluegill, weight 0.3 g) 6.0 mg/L/96 hrtemp 24 °C. Static bioassay without aeration, pH 7.2-7.5, water hardness 40-50 mg/L as calcium carbonate and alkalinity of 30-35 mg/L. /Technical, 97.4%/LC50 Lepomis macrochirus (Bluegill) 28.0 mg/L/24 hr /Conditions of bioassay not given/LD50 Agelaius phoeniceus (Red-winged blackbird) oral 5.4 mg/kg /from table/LD50 Starlings oral 31.6 mg/kgFor more Ecotoxicity Values (Complete) data for DIMETHOATE (49 total), please visit the HSDB record page. |
| 環境中動態 | FORMOTHION & DIMETHOATE SHOULD BE CONSIDERED TOGETHER SINCE THEIR SIGNIFICANT RESIDUES APPEAR TO BE IDENTICAL @ HARVESTTHAT IS, EFFECT OF APPLYING DIMETHOATE & FORMOTHION WILL BE ADDITIVE.TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values which range from 5.2 to 50(2-6), indicate that dimethoate is expected to have very high mobility in soil(SRC). Volatilization of dimethoate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.87X10-6 mm Hg(15), and water solubility, 23,300 mg/L(15). Dimethoate soil half-life values of 2.2 days(16), 7 days(7-9), 11 days(10) and as much as 122 days(11) have been reported. After 6 days, average dimethoate losses due to evaporation from uncovered soil columns were 40.4, 32.3, 23.0, and 24.9% in sand, sandy clay loam, loam, and clay loam, respectivelydimethoate losses were directly proportional to water losses(12)this study indicates that dimethoate may be removed from terrestrial surfaces via evaporation(SRC). Dimethoate will be susceptible to hydrolysis in moist alkaline soils based on a reported base catalyzed rate constant of 756 1/m-hr at pH 9 which corresponds to a half-life of 3.7 days in water(13). Biodegradation may be an important fate process in soil(SRC) with 77% degradation reported in clay loam soil in 2 wks compared to 18 and 20% degradation in the same soil that had been autoclaved or irradiated(14).AQUATIC FATE: Based on a classification scheme(1), experimental Koc values which range range from 5.2 to 50(2-6), indicate that dimethoate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(7) based upon an estimated Henry's Law constant of 2.4X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 1.87X10-6 mm Hg(8), and water solubility, 23,300 mg/L(8). According to a classification scheme(9), BCFs of 1.1-2.4 and 2.7-6(10), suggests bioconcentration in aquatic organisms is low(SRC). Dimethoate hydrolyzes very slowly in sterile buffered solutions at pHs 5 and 7 with half-lives of 156 and 68 days respectively, but hydrolyzes rapidly to desmethyl dimethoate and dimethylthiophosphoric acid with a half-life of 4.4 days at pH 9(11). Photolysis and volatilization from water do not appear to be important removal process of dimethoate from water(SRC). Half-lives of 171, 173 and 219 days were given for river water, filtered river water and sea water, respectively, at 6 °C, and 43, 29 and 36 days, respectively, at 22 °C(12), suggesting that biodegradation may be a slow environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethoate, which has a vapor pressure of 1.87X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dimethoate 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 5 hrs(SRC), calculated from its rate constant of 7.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase dimethoate may be removed from air via dry deposition(SRC), and one monitoring study(4) indicates that dimethoate is removed from the atmosphere via wet deposition. Products of oxidation and hydrolysis accounted for 1.5 and 11%, respectively, of the dimethoate deposited on an untreated glass surface left in a greenhouse for 7 days(5). Therefore, some oxidation and hydrolysis may account for the removal of dimethoate from air(SRC). Based on a lack of absorbance of wavelengths of light above 290 nm(6), dimethoate is not expected to be susceptible to direct photolysis by sunlight(SRC).When applied to plants, dimethoate was ... decomposed ... on surface ... by hydrolysis & oxidation. On the plant surface, dimethoate underwent non-enzymatic oxidation to the oxygen analog & hydrolysis to water sol deriv identified as dimethyl phosphoric & O,O-dimethyl phosphorothioic acids, desmethyl dimethoate ... |
| 食品調査値 | After applying 150 grams dimethoate/ha to lettuce, dimethoate was detected on the outer leaves at concns of 4.61, 1.36, 0.19, and 0.01 ppm, fresh weight, after 2, 4, 7, and 14 days, respectivelyit was detected on the inner leaves at a concn 0.01 ppm, fresh weight, after 7 days(1). After applying 300 grams dimethoate/ha to lettuce, dimethoate was detected on the outer leaves at concns of 8.44, 1.2, 0.32, and 0.06 ppm, fresh weight, after 2, 4, 7, and 14 days, respectivelyit was detected on the inner leaves at a concn of 0.04 ppm, fresh weight, after 7 days, respectively(1). Dimethoate was not detected above a detection limit of 0.01 ppm in the edible pulp of lemons and oranges 52-59 days postapplication at 1.4 kg/ha(2). Dimethoate was found on strawberries at 0.041 ppm 17 days after application of 38.1 ppm in 1986(3). Dimethoate was found on strawberries at 0.019 ppm 17 days after application of 36.186 ppm in 1987(3). One day after the application of 1.5 kg/ha of dimethoate on olives, olive concns were 1.6 mg/kg, olive oil concns were 0.33 mg/kg(4). Eight days after treatment olive oil concns were 0.22 mg/kg and 14 days after treatment olive concns were 0.17 mg/kg and dimethoate was not detected in olive oil(4). Olives in Portugal were treated with 60 g ai/ha on Feb 9, 1980 and July 10, 1980residues in olives were 5.3, 3.1, 1.5, 0.78, 0.41, 0.28 and 0.3 mg/kg 1, 7, 14, 21, 28, 35 and 41 days after the last treatment, respectively(5). No dimethoate was detected in olive oil processed from olives harvested on the same corresponding days(5). Dimethoate was found in laboratory pressed olive oil at 0.48, 0.33, 0.19 and 0.09 mg/kg 8, 20, 32 and 47 days, respectively, after treatment on Nov 16, 1988 with 60 g ai/ha, and at 0.06 mg/kg after 53 days in industrial pressing(5).Dimethoate was qualitatively identified in 1 large fruit sample during Fiscal Year 1976 (FY76), 16 small fruit samples during FY75-76, 33 leaf and stem vegetables, 196 vine and ear vegetable sample, and 46 bean samples during FY74-76, and 1 root vegetable sample during FY75(1). Dimethoate has been detected, by FDA's pesticide residue monitoring program, in American foods during fiscal years 1978-1992(2-6)however, the concns and the frequencies of occurrence were not reported(2-6). Dimethoate was qualitatively identified in 167 of 27,065 human food samples during FY88-89(7). In a US monitoring survey of 6970 produce samples (fruits and vegetables) collected between 1989 and 1991, dimethoate was detected in grapes, greens, lemons, and peppers(8). During October 1, 1981 and September 30, 1986, dimethoate was found in 319 U.S. agricultural commodities at a concn range of >0-0.05 ppm, 117 samples at 0.05-0.1 ppm, 192 at 0.1-0.5 ppm, 29 at 0.5-1.0 ppm, 20 at 1.0-2.0 ppm, and 8 agricultural commodities at a concn > 2.0 ppm(9). This study does not distinguish between domestic and imported commodities or between surveillance and compliance samples(9). During October 1, 1981 and September 30, 1986, dimethoate was found in 145 U.S. domestic agricultural commodities conducted by surveillance sampling at a concn range of >0-0.05 ppm, 64 at 0.05-0.1 ppm, 105 at 0.1-0.5 ppm, 22 at 0.5-1.0 ppm, 17 at 1.0-2.0 ppm, and 5 domestic agricultural commodities at a concn > 2.0 ppm(10). During October 1, 1981 and September 30, 1986, dimethoate was found in 170 U.S. imported agricultural commodities conducted by surveillance sampling at a concn range of >0-0.05 ppm, 50 at 0.05-0.1 ppm, 77 at 0.1-0.5 ppm, 4 at 0.5-1.0 ppm, 3 at 1.0-2.0 ppm, and 3 imported agricultural commodities at a concn > 2.0 ppm(10). Dimethoate was not detected in green bean, peach, sweet potato, spinch, tomato or strawberry(11). Dimethoate was not detected in acorn squash, apple, peach, strawberry, pear, apricot, spinach, lettuce, carrot, grape, tomato, orange, potato or corn, it was detected in green beans, however after washing and cooking dimethoate was no longer detected(12). Dimethoate was found in domestic and imported pears and tomatoes from a 1989-1993 US Food and Drug Administration pesticide monitoring program(13).Dimethoate was identified between 1983 and 1984 in 1 of 47 composite samples of strawberries from Ontario, Canada at a concn of 0.04 mg/kg(1). During April 1, 1989 - December 3, 1991, dimethoate was detected in Canadian domestic commodities of fresh apples, fresh bean and fresh lettuce(2). In the same Canadian study(2), dimethoate was also detected in imported commodities of fresh beans, apples, broccoli, cucumber, grapes, lettuce, orange, pepper, and pear. Dimethoate was found in 1 imported canned spinach samples taken in a Canadian commodities study running from 1/1/1992-3/31/94 of 16,198 imported commodities and 5784 domestic commodities(3). Dimethoate was detected in 35 of 234 ready-to-eat foods items that represented about 5,000 food types sampled over 10 years by the US FDA from 1982-1991the average concentration in the 236 food types that tested positive was 0.0094 ug/g(4). Of 802 fruit and vegetables tested in Ontario, Canada from 1991-1995 3.3% were positive for dimethoate(5). Dimethoate was found in apple, bean, celery, cherry, leaf lettuce and head lettuce in domestic fruits and vegetables from Jan 1992-Mar 1994 in Canada(6). Dimethoate was not found in apple juice, beets, blueberry, cabbage, carrot, cucumber, grape juice, mushroom, onion, parsnipe, peach, pear, pepper, plum, potato, rutabagas, spinach, strawberry or tomato from the same study(6). Imported fruits and vegetables in this same Canadian study found dimethoate in apple, bean, broccoli, celery, frozen cherry, grape, head lettuce, lim, orange, pear, pepper, spinach and tangerine(6). Dimethoate was not detected in imported apricot, artichoke, avocado, banana, beet, brussels sprout, cabbage, cantaloupe, carrot, cauliflower, cherry, cucmber, eggplant, escarole, grapefruit, kiwi, leaf lettuce, lemon, mango, melon, mushroom, nectarine, onion, parsley, peach, pimiento, pineapple, plum, potato, radish, raspberry, rutabaga, sauerkraut, snow pea, squash, star fruit, strawberry, sweet potato, tomato, turnip, ugly fruit and yam from Jan 1992-Mar 1994 in Canada(6).In a 1995 monitoring program in Egypt dimethoate was not detected in cauliflower, carrot, courgette, onion, cantaloupe, guava or mango(1). Dimethoate was found in cabbage, cucumber, eggplant, green beans, green peas, lettuce, pepper, tomato, apple, grape, orange, peach and strawberry in the same 1995 monitoring program(1). In a 1996 monitoring program in Egypt dimethoate was not detected in cabbage, artichoke, board bean, cauliflower, okra, onion, squash, tomato, carrot, sweet potato, taro, banana, dates, fig or lemon lime(2). Dimethoate was found in grape leaf, melokhia, lettuce, watercress, spinach, cantaloupe, cucumber, eggplant, green bean, green pea, pepper, apple, apricot, grape, guava, mango, orange, peach, pear, plum, pomegranate and strawberry in the same 1996 monitoring program(2). Dimethoate was found in potato and citrus taken from local Egyptian markets Mar 1991-Jan 1992(3). Dimethoate was not detected in cumin, anise, ginger or caraway but was found in cinnamon (6 ug/kg) in Ismailia, Egypt(4). Dimethoate was found in unprocessed orange, tomato, cucumber, apple and grape from retail markets in Alexandria City, Egypt 1997-1998, but was only found in processed grape(5).For more Food Survey Values (Complete) data for DIMETHOATE (6 total), please visit the HSDB record page. |
| 有害作用 | Other Poison - Organophosphate |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.Oral (L1188)inhalation (L1188)dermal (L1188) |
| Milk Concentrations | Dimethoate was applied dermally to lactating cow. Thin-layer chromatography indicated the presence, in addition to dimethoate, of dimethoxon, dimethoate acid and desmethyl dimethoate in the bloodand of dimethoxon, dimethylthio (or dithio) phosphate and possibily desmethyl dimethoate in the milk.When a combination of dimethoate and omethoate (dimethoxon) was given to cows in dosages of 1 and 0.1 mg/kg body weight, respectively, for 14 days, only residues of the metabolite omethoate were observed in the milk (0.004-0.125 mg/kg). Three days after the application, neither compound could be detected. When dosages of 0.5 mg dimethoate/kg and 0.05 mg omethoate/kg were given for 14 days or when corn silage containing 1-7 mg dimethoate/kg (resulting in dosages of 0.06-0.36 mg/kg body weight) was given for 28 or 42 days, no residues were detected in the milk ... .Dimethoate was found in 1 of 96 samples taken from 4 brands of Mexican commercial pasteurized milk over a 12 month period(1). Dimethoate was not found in 6 milk products from a 10 year US Food and Drug study from 1982-1991(2). Dimethoate was not found in 14 milk samples tested in Rome, Italy(3). Dimethoate was found in 1 of 7 composite samples over a 3 month period in Monofia and Kalubia provinces in Egypt(4). |
| 毒性の概要 | Dimethoate 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 10 lb or 4.54 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).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Dimethoate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 micronsor is handled in solution or in molten formor meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . |
| 州飲料水ガイドライン | (AZ) ARIZONA 1.2 ug/l(CA) CALIFORNIA 1 ug/l(FL) FLORIDA 5 ug/l(WI) WISCONSIN 2 ug/l |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | TE1750000 |
| 輸送番号（UN） | UN 2783 |
| 毒性 | LD50 orally in rats: 250 mg/kg (Schafer) |
| PRTR法 | 第1種指定化学物質 |
| 税関コード | 29309090 |
| 危険文句（R） | 21/22-63-43-36/37/38-23/24/25-45-36-20/21/22-11-67-40 |
| 化審法 | 一般化学物質 |
| 安衛法 | 57,57-2 |
| 消防法 | 危-4-1-S-II |
| 危険表示 | Xn,T,F |
| 安全措置（S） | 2-36/37-24/25-23-53-26-16 |
| 危険等級 | 6.1(b)Acute Tox. 3 DermalAcute Tox. 3 OralAquatic Chronic 2 |
| 包装等級 | III |
| 毒劇物取締法 | III |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 60-51-5(Hazardous Substances Data) |
用途
用途
有机磷类殺虫
説明
Dimethoate is colorless crystalline substance, mp 49 C, bp 117 C/0.1 mm Hg, vp 0.25 mPa (25 C). The solubility in water is 23.8 g/L at 20 C and pH 7. It is readily soluble in polar organic solvents. Log Kow = 0.7. Dimethoate is relatively stable in aqueous media at pH 2–7 and hydrolyzed in alkaline media; DT50 (20 C) at pH 9 is 12 d.
使用
Dimethoate is used to control of a wide range of insect and mite pests in many crops. It is also used to control flies in animal houses.
一般的な説明
A white crystalline solid, with a camphor-like odor, white to grayish crystals for technical product. Dimethoate is a contact and systemic organophosphate insecticide effective against a broad range of insects and mites when applied on a wide range of crops. Dimethoate has not been produced in the U.S. since 1982.