メチラム

Zineb

HCID 5284484CAS 12122-67-7

基本情報

標準SMILES
S=C([S-])NCCNC(=S)[S-].[Zn+2]
InChIKey
AMHNZOICSMBGDH-UHFFFAOYSA-L
分子式
C4H6N2S4Zn
平均分子量
275.8 g/mol

概要

Metiram can cause cancer and developmental toxicity according to The Environmental Protection Agency (EPA).

名称と識別子

優先名称
Zineb
IUPAC
zinc N-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate
現地名
メチラム
英語名
METIRAM
分子式
C12H12N6S16Zn
分子量
818.69388

名称と別名

ZINEB12122-67-7TritoftorolParzateDTXSID5021465Zinc Ethylenebis(dithiocarbamate)X1FSB1OZPTENT-14874Zinc ethylenebisdithiocarbamatezinc ethane-1,2-diyldicarbamodithioatezinc ethane-1,2-diylbis(dithiocarbamate)Cynkotox
名称をさらに表示
メチラムメチラム標準品CS_N-13086-250MG_メチラム(試薬グレード)amarexPOLYRAMFMC9102METIRAMTHIUMETMetriamnia9102polymatMethiramMetriraM
NovozirCHEBI:52498CinebNSC-49513ClortocaffaroAaphytoraAphytoraAsporum

データベース識別子

CAS
12122-67-7、9006-42-2
PubChem CID
5284484
DTXSID
DTXSID5021465
ChEMBL
CHEMBL1411246
ChEBI
CHEBI:52498
UNII
X1FSB1OZPT
EC Number
235-180-1

物性

構造計算による物性

極性表面積
90.2 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
3
重原子数
11

実験および物理化学的性質

Chemical ClassesMutagens
Pesticides · 4 件

Pesticide -> EPA IRIS

Fungicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Dithiocarbamates (Pesticide)

LogPlog Kow = 1.30
OdorPractically odorless
DensityApprox 1.74 at 20 °C
Color/Form · 4 件

Powder or crystals from chloroform + alcohol

Light-tan solid

WHITE POWDER OR CRYSTALS

Pale yellow powder

物理化学的性質

融点
156 ℃ · 156℃ (approx, Decomposition)
貯蔵温度
0 · 0-6°C
溶解性
DMSO(微加熱)
外見
個体
色
オフホワイト
EPAの化学物質情報
Metiram (9006-42-2)

化学的性質

化学的特性Light yellow solid or powder at room temperature. Characteristic dithiocarbamate odor.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

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

P261, P271, P272, P280, P302+P352, P304+P340, P319, P321, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P271, P272, P280, P302+P352, P304+P340, P319, P321, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 3 件

01/245/EC

Zineb: HSNO Approval: HSR003171 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Zinc, [[1,2-ethanediylbis(carbamodithioato)](2-)]-: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 件

Flash point data for this chemical are not available, but it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible.
Health HazardsSYMPTOMS: Symptoms associated with exposure to this compound include irritation of the skin, eyes and mucous membranes as well as anemia.

安全と保護具

Fire Fighting · 2 件

Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

First Aid · 1 件

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.

Safe Storage · 1 件

Separated from food and feedstuffs, strong bases, amines, amides, acids and strong oxidizers. Store only in original container. Provision to contain effluent from fire extinguishing. Cool. Dry. Keep in the dark. Keep in a well-ventilated room.

Fire Fighting ProceduresWater spray, foam, powder, carbon dioxide ... Keep drums, etc., cool by spraying with water.
Storage ConditionsStore in well-aired, fresh (less than 30 °C), dry area away from dwellings, animal shelters and stored food.

毒性情報

TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (L49)
Target OrgansEndocrine
Health EffectsChronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (L49)
Ecotoxicity Values · 5 件

LD50; Species: Anas platyrhynchos (Mallard duck, male, 11-12 months old) oral >2000 mg/kg /sample purity 95%/

LD50; Species: Phasianus colchicus (Pheasant, female, 3-4 months old) oral >2000 mg/kg /sample purity 95%/

LC50; Species: Coturnix japonica (Japanese quail) oral >5000 ppm (diluent: corn oil) /Technical grade, 85% ai/

EC50; Species: Chlorella pyrenoidosa (Green algae, 10+8 cells/100 mL); Conditions: freshwater, static, 20 °C; Concentration: 1800 ug/L for 96 hr; Effect: growth, general /95% purity/

For more Ecotoxicity Values (Complete) data for Zineb (16 total), please visit the HSDB record page.

Environmental Fate · 5 件

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 308-1158(2) indicate that zineb is expected to have low to moderate mobility in soil(SRC). Volatilization of zineb from moist soil surfaces is not expected to be an important fate process since zineb is a zinc salt(SRC). Zineb is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of <7.5X10-8 mm Hg(3). Zineb field half-lives range from 23-43 days(4). Dithiocarbamate fungicides undergo rapid decomposition in the presence of moisture(5-6); therefore, zineb decomposition in and on wet soil may be an important fate process(SRC).

TERRESTRIAL FATE: Zineb is hydrolyzable and does not persist long in soil(1). Its persistence in soil is less than that in water so zineb's degradation in soil is probably catalyzed by soil components. Loss in soil, while rapid, was not complete at the end of 45 days(1). Within four months after a field planted with forage was sprayed with zineb, 99.7% of the fungicide was no longer present at effective levels(1). In the laboratory, zineb lost its efficacy in 16 days at 30 or 40 °C and in the field its bioactive half-life was 16 days(2). Since the fungitoxicity of zineb increases for four days before it declines(2), degradative products are probably the active fungicides and the half-life of the zineb is less than what would be inferred from its bioactivity(SRC). In an experiment in a microagricultural chamber containing 19 day old tomato plants, zineb was applied as a spray at day 56 and day 86, the latter spray containing radiolabeled fungicide(3). The experiment was terminated on day 156 and the half-life of the zineb was 23 days. It was primarily confined to the top 1 cm of soil(3). 36% of the zineb was removed through volatilization of low molecular weight degradation products(3).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 308-1159(2) indicate that zineb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected since zineb is a zinc salt(SRC). According to a classification scheme(3), an estimated BCF of 3(SRC), from its log Kow of 1.3(4) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Surface water mixed with sediment produced 70% cumulative radio-labeled carbon dioxide after 50 days incubation(6), suggesting that biodegradation may be an important fate process in water(SRC). Hydrolysis half-lives for zineb in relation to pH are 9 mins at pH 3.8, 6.5 hrs at pH 5.7, 96 hrs at pH 7.0, and 405 hrs at pH 8.0(6). Zineb is unstable in aqueous solutions, producing ethylenethiourea, 5,6-dihydro-3H-imidaz-1,2,4-dithiazole-3-thione, ethylenediamine, ethylenediisothiocyanate, sulfur, carbon disulfide, and hydrogen sulfide(7). Zineb is unstable to moisture on prolonged storage(7). When zineb was spilled into the Rhine River during a warehouse fire, it hydrolyzed very quickly(8). The mass of zinc resulting from the fire was unimportant(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), zineb, which has a vapor pressure of <7.5X10-8 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Zineb will be lost by gravitational settling(3). Zineb contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

ATMOSPHERIC FATE: In the atmosphere zineb will exist primarily as dust or an aerosol and be lost by gravitational settling. In an experiment in a microagricultural chamber containing 19 day old tomato plants, in which zineb was applied as a spray, the half-life of zineb in air, as determined by measuring (14)C-zineb and the ethylenediamine derivative, was 11 and 14 days, respectively(1).

Food Survey Values · 2 件

Zineb residues of 0.57 and 0.77 ppm were found in grapes sprayed 5 times and harvested 20 days after the last spraying(1). Similarly, another study reported residues of 1.02-2.05 ppm in grapes sprayed 11-13 times and harvested <20 days after the last spraying(1). A Food and Drug Administration study of pesticide residues in ready-to-eat foods in 1968-1972 indicates that zineb is an infrequent contaminant with concentrations of 0.7-1.4 ppm being reported in onions and 3.0 ppm in celery(3). Of the 1522 samples of leaf and stem vegetables analyzed for zineb in FY1970-1976 in the FDA Total Diet Program, zineb was found in 10% of samples, of which 8% exceeded 0.04 ppm and 2.7% exceeded 2.00 ppm(5). The average zineb concn was 0.461 ppm(5). No zineb residues were reported in tested composite samples of cherries, peaches and strawberries delivered to farmer's wholesale markets in Leamington and Toronto, Ontario between 1980-1984(2). Samples of canned pears and baby food contained no zineb, although the latter contained ETU(4). Zineb was detected in crops from Cuba; 3.6-7.2 ug/kg in tomato, below detection limit in onion and pepper, and not detected in cucumber and citrus(6).

Zineb was detected in 0.057% of 13,980 food sampled for pesticides in fiscal year 1988(1). Out of 710 domestic and 949 imported pears sampled for various pesticides from 1991-1992, zineb was not found as a residue(2). Ethylene bis-dithiocarbamate (EBDCs) fungicides, which includes zineb, were found to be the most prevalent residue found on fruits and vegetables analyzed in Switzerland in 1989-90(3). Out of 461 salads analyzed in Geneva, 23 samples had levels of EBDCs exceeding tolerance values(3). In 1989, 18,798 food samples were analyzed by the FDA for pesticide residues(4). Of these, only 1278 samples were analyzed for EBDCs in which zineb was detected (percent positive and concentrations not specified)(4). Vegetables analyzed included peppers, leafy vegetables, cantaloupe, squash and peas(4). In 1990, the same study was conducted by the FDA but with 1472 samples being analyzed for EBDCs(5). Once again, zineb was detected (percent positive and concentrations not specified)(5).

法規制情報

FDA RequirementsZineb is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1 件

U114; As stipulated in 40 CFR 261.33, when ethylenebisdithiocarbamic acid, salts & esters, 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 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). /Ethylenebisdithiocarbamic acid, salts and esters/

FIFRA Requirements · 2 件

Pesticide chemicals that cause related pharmacological effects will be regarded as having an additive deleterious action. Where residues from two or more chemicals in the same class are present in or on a raw agricultural commodity the tolerance for the total of such residues shall be the same as that having the lowest numerical tolerance in this class. Zineb is a member of the class of dithiocarbamates.

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 continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Zineb is found on List B. Case No: 2750; Pesticide type: insecticide, fungicide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Zineb; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

CERCLA Reportable Quantities · 1 件

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 5000 lb or 2270 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). /Ethylenebisdithiocarbamic acid, salts and esters/

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Zinc and compounds/
State Drinking Water Guidelines · 3 件

(FL) FLORIDA 350 ug/L

(AZ) ARIZONA 350 ug/L

(ME) MAINE 350 ug/L

安全データ

rtecs
TR6250000
ridadr
UN 1282 3 / PGII
有毒物質データの
9006-42-2(Hazardous Substances Data)

化学と産業

薬理情報

Metabolism/Metabolites · 6 件

ETU and DIDT /(5,6-dihydro-3 H-imidazo(2,1-C)-1,2,4-dithiazole-3-thione)/ were the major metabolites found in the urine of rats treated with zineb, and carbon disulfide was detected in the expired air.

The metabolism of the fungicide zineb, (zinc ethylenebisdithiocarbamate), has been studied in the rat and the marmoset. In both species a relatively large proportion (21-22%) of the original zineb administered was detectable in the excreta as ethylenethiourea (ETU) ... A further proportion (2-5%) was determined to be ethyleneurea which is a metabolite of ETU. Results of comparative experiments in marmosets revealed that ETU was photolabile in the presence of excreta, thus showing the importance of conducting the studies in the dark.

Zineb ... Is metabolized in rats to carbon disulfide, which is expired, and to ethylenethiourea ... and ethylenebis(isothiocyanate)sulfide (ebis) ... which are excreted in urine.

Ethylenethiourea is the major metabolite in plants. Ethylenethiuram monosulfide and presumably ethylenethiuram disulfide and sulfur are also formed.

For more Metabolism/Metabolites (Complete) data for Zineb (9 total), please visit the HSDB record page.

Zinc can enter the body through the lungs, skin, and gastrointestinal tract. Intestinal absorption of zinc is controlled by zinc carrier protein CRIP. Zinc also binds to metallothioneins, which help prevent absorption of excess zinc. Zinc is widely distributed and found in all tissues and tissues fluids, concentrating in the liver, gastrointestinal tract, kidney, skin, lung, brain, heart, and pancreas. In the bloodstream zinc is found bound to carbonic anhydrase in erythrocytes, as well as bound to albumin, _2-macroglobulin, and amino acids in the the plasma. Albumin and amino acid bound zinc can diffuse across tissue membranes. Zinc is excreted in the urine and faeces. (L49)

MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Absorption, Distribution and Excretion · 5 件

... Approx 70-75% of ingested zineb passed through the gastrointestinal tract of rats and appeared in the feces within 24-72 hr.

... Only 11 to 17% of an oral dose of zineb is absorbed from the gastrointestinal tract of the rat. Some additional material may be absorbed following breakdown in the intestine. At different dietary levels 68.5 to 74.9% of the ingested material was recovered unchanged in the feces.

In short-term static bioaccumulation experiments with (14)C-labeled zinc ethylenebisidithiocarbamate (zineb) and zinc dimethyldithiocarbamate (ziram) both compounds were rapidly disseminated through the tissues. Whole body elimination was rapid with 45% and 25% of the initial radioactivity from ziram, and zineb, respectively, being retained by the end of the 16 day depuration period. Pigmented tissues appeared to be major distribution sites as well. This may be related to the affinity of the compounds and/or their degradation products to melanin or to complexion with phenoloxidase, a copper containing enzyme involved in melanin synthesis. Autoradiography also revealed a high labeling of thyroid follicles. The results show that dithiocarbamates are selectively localized in various tissues, reported to be the target organs for their toxic actions.

Urinary and fecal excretion of ethylene thiourea, a metabolite of ethylene-bis-dithiocarbamic /acid/ fungicides, was monitored in rats for 16 days after they were administered a single oral dose of zineb. After 48 hr, 86% of the excreted ethylene thiourea was in the urine, 14% in the feces. Urinary excretion peaked at 24 hr after ingestion, at which time 52% of the total urinary ethylene thiourea had been excreted. Low levels of ethylene thiourea excretion continued in urine for the length of the study, by which time 5.1% of the zineb /oral dose/ was excreted as urinary ethylene thiourea. Fecal excretion of ethylene thiourea was complete after 3 days.

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

用途と製造

Uses · 6 件

A fungicide that was used on fruits and vegetables; [EXTOXNET] Also formerly used as fungicide for paints, fabrics, leather, paper, plastics, surfaces already painted and those to be painted, and wood surfaces; [HSDB]

All registrations were voluntarily canceled by the manufacturer; [EXTOXNET]

Pulp and Paper Processing [Category: Industry]

For zineb (USEPA/OPP Pesticide Code: 014506) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

/Formerly used in US/ as fungicide on fruits, vegetables, field crops and a large number of ornamental plants and for treatment of many seeds. In paints and on fabrics, leather, linen, painted surfaces, surfaces to be painted and paper, plastics and wood surfaces

Impurities · 2 件

Many commercial samples of ... Zineb ... have been shown to contain ethylenethiourea.

After storage of Zineb in darkness, ethylenethiourea, ethylenethiuram mono- and disulfide, trace of sulfur, and one unidentified compound were observed.

Consumption Patterns · 2 件

Approx 55% as a fungicide for apples; approx 17% as a fungicide for home and garden, lawn, and turf; approx 14% as a fungicide for deciduous fruit; and approx 14% as a fungicide for vegetables (1975)

239 tons are used annually

Methods of Manufacturing · 3 件

Reaction of ethylene diamine and carbon disulfide in the presence of alkali, followed by addition of zinc sulfate to precipitate Zineb

Zineb is produced by mixing ethylenebis(dithiocarbamate) with an aqueous zinc sulfate solution, or by reaction of Nabam with a solution of zinc salts.

Reaction of sodium ethylenebisdithiocarbamate with zinc sulfate or other zinc salts. In practical application as a fungicide these reactants are mixed in the presence of lime; the zineb is not formed until after reaction of the carbon dioxide of the air with the film of the other chemicals on the leaf or fruit.

Formulations/Preparations · 5 件

Grades: commercial dusts & wettable powders usually contain 65% active material.

Dithane Z78 and Parzate Xineb are wettable powders containing 75% Zineb and used generally at 1 1/2 to 2 lb/100 USA gal.

Mancozeb (Dithane M45) is ... a combination of maneb and zineb.

Wettable powder (700 or 750 g ai/kg); dust (Dithane dust). Mixtures include: 'Cupro-phynebe' (Bayer), 'Super Mixy', wettable powder (150 g zineb + 375 g copper (as copper oxychloride)/kg); 'Turbair Dicamate' (zineb + mancozeb).

For more Formulations/Preparations (Complete) data for Zineb (7 total), please visit the HSDB record page.

General Manufacturing Information · 5 件

/Zineb was introduced/ ... by Rohm & Haas Co (& EI du Pont de Nemours & Co who no longer manufacture or market it) (USP 2,457,674; 3,050,439) ...

Generally non-phytotoxic except to zinc-sensitive plants.

In practical application as a fungicide these reactants are mixed in the presence of lime; the zineb is not formed until after reaction of the carbon dioxide of the air with the film of the other chemicals on the leaf or fruit.

Zineb also results from combining nabam (or diammonium or potassium ammonium analogs) with zinc sulfate in the spray tank.

All registrations of zineb were previously voluntarily cancelled by the registrant.

応用分野 · 3 件

用途メチラム試験用標準品。

使用Metriram is a polymeric dithiocarbamic fungicide used in agriculture. Metiram is present as a mixture rather than a complex and is not assigned an ISO name. Metiram is used commonly in the protection of grapevines, apples, tomatoes, potatoes as well as other crops.

一般的な説明Yellow powder. Non corrosive. Insoluble in water. Used as an fungicide.

サプライヤー43 社

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]

関連反応

5 件

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