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2,3,5,6-テトラクロロニトロベンゼン

1,2,4,5-Tetrachloro-3-nitrobenzene

HCID 8330
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
117-18-0
標準SMILES
O=[N+]([O-])c1c(Cl)c(Cl)cc(Cl)c1Cl
InChIKey
XQTLDIFVVHJORV-UHFFFAOYSA-N
分子式
C6HCl4NO2
平均分子量
260.9 g/mol
単同位体質量
258.876139

概要

2,3,5,6-tetrachloronitrobenzene appears as pale yellow crystals. (NTP, 1992)

名称と識別子

優先名称
1,2,4,5-Tetrachloro-3-nitrobenzene
IUPAC
1,2,4,5-tetrachloro-3-nitrobenzene
現地名
2,3,5,6-テトラクロロニトロベンゼン
英語名
Tecnazene
分子式
C6HCl4NO2
分子量
260.89

名称と別名

TECNAZENE117-18-01,2,4,5-Tetrachloro-3-nitrobenzene2,3,5,6-TetrachloronitrobenzeneMyfusanTecnazenArenaTCNBTurbostoreAltritanEasytecHickstor
名称をさらに表示
2,3,5,6-テトラクロロニトロベンゼンホロサンDB-905フミット1-ニトロ-2,3,5,6-テトラクロロベンゼン2,3,5,6-テトラクロロ-1-ニトロベンゼン3-ニトロ-1,2,4,5-テトラクロロベンゼンフサレックステクナゼン1,2,4,5-テトラクロロ-3-ニトロベンゼンテクナゼン標準品テクナゼン2,3,5,6-テトラクロロニトロベンゼン2,3,5,6-テトラクロロニトロベンゼン STANDARD2,3,5,6-テトラクロロニトロベンゼン Standard, 100 µg/mL in MeOH2,3,5,6-テトラクロロニトロベンゼン Standard, 100 µg/mL in Toluene2,3,5,6-テトラクロロニトロベンゼン標準品Technazene2,3,5,6-tcnbTetrachloronitrobenzeneHystor
FumiteHystoreHytecChipman 3,142TeknazenFumite TechalinNew HystoreFusarex G

物性

構造計算による物性

XLogP
3.9
極性表面積
45.8 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
13
形式電荷
0
複雑度
195

実験および物理化学的性質

SpringerMaterials PropertiesFusion temperature
Pesticides · 4 件

Fungicides, Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fungicides

Pesticide (Tecnazene) -> USDA PDB

LogP · 3 件

log Kow = 4.38

4.38

3.89

OdorODORLESS
Density · 2 件

1.744 (NTP, 1992) - Denser than water; will sink

1.744 at 25 °C/4 °C

Color/FormColorless crystals
Solubility · 6 件

less than 0.1 mg/mL at 68 °F (NTP, 1992)

READILY SOL IN CARBON DISULFIDE

Soluble in ethanol, benzene, and chloroform

In ethanol about 40 mg/L (25 °C)

/Tecnazene/ is readily soluble in ... ketones, and aromatic and chlorinated hydrocarbon compounds. It is practically insoluble in water (0.44 mg/l at 20 °C) ...

In water, 2.09 mg/L at 25 °C

CorrosivityNon corrosive at room temp
Boiling Point · 2 件

安全と法規制

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

GHS分類

GHS Classification · 6 件

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information00/725/EC
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. When heated to decomposition it emits toxic fumes. (NTP, 1992)
Hazards Summary · 1 件

May cause irritation; [CAMEO] May cause irritation; May cause skin sensitization; With the exception of one report of dermal sensitization in agricultural workers, tecnazene does not seem to present a problem occupationally. [INCHEM] May cause skin sensitization; [eChemPortal: ESIS] An irritant; May cause skin sensitization; [MSDSonline]

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Special ReportsWHO; Environ Health Criteria 42: Tecnazene (1984)
FIFRA Requirements · 1 件

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 1,2,4,5-Tetrachloro-3-nitrobenzene is found on List B. Case No: 2630; Pesticide type: Fungicide, antimicrobial; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case 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): 1,2,4,5-Tetrachloro-3-nitrobenzene; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

The metabolic fate of [U-14C]-2,3,5,6-tetrachloronitrobenzene (tecnazene) has been determined in the male and female rat following a single dose of 1 mg/kg and in surgically prepared, bile-duct-cannulated rats following a single oral dose of 135 mg/kg. Radioactivity in the female rat was excreted mainly in urine (82%). The male rat, however, excreted approximately equal amounts of radioactivity in urine and feces (the latter via bile). The principal metabolic pathway was conjugation with glutathione (GSH) and concomitant nitro-displacement. The GSH-conjugate and related metabolites were excreted in the bile and ultimately in the urine as the mercapturic acid conjugate. The cysteine conjugate underwent beta-lyase-mediated metabolism to yield a thiol that underwent subsequent methylation to the thioanisole followed by S-oxidation. 4. A novel tetrachloromethyldisulphide metabolite was also formed.

Some redn of nitro group took place in gut after admin of 2,3,5,6-tetrachloro- nitrobenzene to rabbits. Very small amt of tetrachloroaniline, mercapturic acid, free 4-amino-2,3,5,6-tetrachlorophenol, a sulfate, and a glucuronide were excreted in urine.

Yields S-(2,3,5,6-tetrachlorophenyl)glutathione in rat. /From table/

Mercapturic acid conjugate was excreted at a rate of 11% within 48 hr of the administration of 1-3 g of tecnazene to rabbits. Other metabolites excreted included an ether glucuronide (12%), 2,3,5,6-tetrachloroaniline (10%), unconjugated 4-amino-2,3,5,6-tetrachlorophenol (2%) and an etheral sulfate (1%).

For more Metabolism/Metabolites (Complete) data for TECNAZENE (7 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 3 件

The absorption, distribution, metabolism and excretion of [14C]tecnazene has been studied in the rat. Earlier metabolism studies with unlabelled tecnazene were also carried out on the rat, rabbit, guinea pig and pigeon. Tecnazene is extensively metabolized in all species. In animals the nitro group is reduced, yielding 2,3,5,6-tetrachloroaniline and 4-amino-2,3,5,6- tetrachlorophenol. These metabolites are excreted in the urine as such or, in the case of the phenol, after the formation of ethereal glucuronide or sulfate conjugates. The nitro group can be replaced by glutathione, leading to the formation of another major metabolite, S-(2,3,5,6-tetrachlorophenyl)-Nacetylcysteine, which is also excreted in the urine.

... the disposition of [14C]tecnazene and its metabolites was followed in male and female rats dosed at 1 mg/kg bw. After 24 hours the highest tissue concentrations of 14C were in the kidneys, liver and nasal passages of both sexes. After seven days 14C residues were low but generally slightly higher in males where the highest concentrations were found in the abdominal fat (0.032 mg/kg, expressed as tecnazene), kidneys (0.016 mg/kg), lungs (0.016), blood (0.014) and heart (0.013 mg/kg). In females, the highest concentration was 0.011 mg/kg in the abdominal fat, blood and ovaries. After seven days the total proportion of the dose present in the tissues was 0.13% and 0.05% in male and female rats respectively. The concentrations of 14C in the tissues appeared to decrease as a function of time on the evidence of autoradiograms at 24 and 48 hours and liquid scintillation counting at 7 days.

関連反応

2 件
反応記録を作成
HRID 203475 の反応式
HRID 203475反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 359602 の反応式
HRID 359602反応物としてuspto-grants-1991_03

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
117-18-0、28804-67-3
PubChem CID
8330
DTXSID
DTXSID0026098
ChEMBL
CHEMBL1420059
ChEBI
CHEBI:82044
UNII
02X6KNJ5EE
EC Number
204-178-2
Nikkaji
J2.001J

579 °F at 760 mmHg (NTP, 1992)

304 °C (with decomp)

Decomposition · 2 件

In solution, decomposes slowly when exposed to UV radiation.

When heated to decomp ... emits very toxic fumes of hydrogen chloride and nitrogen oxides.

Melting Point · 3 件

210 to 212 °F (NTP, 1992)

99.5 °C

99 °C

Vapor Pressure0.0018 [mmHg]

物理化学的性質

融点
98 · 98-101 °C(lit.)
沸点
304 °C · 304 °C(lit.)
比重(密度)
1.744 g/cm3 · 1.744 g/cm3 (25 ºC)
屈折率
1.62 · 1.6200 (estimate)
貯蔵温度
0 · 0-6°C
溶解性
Chloroform (Slightly), Methanol (Slightly)
外見
結晶性
色
White to Light yellow to Light orange
水溶解度
2.087 mg/L · 2.087mg/L(20℃)
BRN
1973805 · 1973805
Henry's Law Constant
4.3 · 4.3×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途
洗浄剤化粧品環境フレーバーそして香料食品および飲料パーソナルケア医薬品
InChI
1S/C6HCl4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H
InChIKey
XQTLDIFVVHJORV-UHFFFAOYSA-N
SMILES
[O-][N+](=O)c1c(Cl)c(Cl)cc(Cl)c1Cl
EPAの化学物質情報
Tecnazene (117-18-0)

化学的性質

化学的特性beige fine crystalline powder

Reactivity ProfileThis compound will behave as a weak oxidizer, and will react with strong reducing agents including hydrides, sulfides and nitrides.
Air and Water ReactionsInsoluble in water.
Toxic Combustion ProductsToxic oxides of nitrogen are produced during combustion. /Nitrochlorobenzene, para, solid/
Hazard Classes and Categories · 3 件

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute Tox. 4 *

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
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.

Fire Fighting Procedures · 1 件

If material on fire, or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn, or burns with difficulty. Use water in flooding quantities as fog. Use foam, carbon dioxide, or dry chemical. Wear self-contained breathing apparatus when fighting fires involving this material. /Nitrochlorobenzene, para, solid/

Storage ConditionsStore in a refrigerator, or in a cool, dry place.
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 3 件

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

Incineration: 1500 °F, 0.5 sec for primary combustion; 2200 °F, 1.0 sec for secondary combustion. The formation of elemental chlorine can be prevented through injection of steam or methane into the combustion process. Nitrogen oxides may be abated through the use of thermal or catalytic devices. /Nitrochlorobenzene/

Trial burn summary: 95% nitrochlorobenzene and 5% dinitrochlorobenzene, liquid injection, afterburner at 1307-1332 °C (2385-2430 °F), residence time 2.3 sec, destruction efficiency of 99.4-99.87% for total organics and > 99.99 - > 99.999 for constituents, hydrochloric acid scrubber efficiency of 99.8%. /Nitrochlorobenzene/

Preventive Measures · 2 件

If material not on fire, and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Nitrochlorobenzene, para, solid/

Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Nitrochlorobenzene, para, solid/

Personal Protective Equipment (PPE) · 3 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Wear protective gloves when handling the concentrate.

Wear full protective clothing. /Nitrochlorobenzene, para, solid/

Other Standards Regulations and Guidelines · 1 件

This review report has been established as a result of the re-evaluation of tecnazene, made in the context of the work programme for review of existing active substances provided for in Article 8(2) of Directive 91/414/EEC concerning the placing of plant protection products on the market, with a view to the possible inclusion of this substance in Annex I to the Directive. ... Based on the information available in the framework of this evaluation and the proposed conditions of use it was concluded from the evaluation that plant protection products containing tecnazene have not been demonstrated to fulfill the safety requirements laid down in Article 5(1)(a) and (b) of Directive 91/414/EEC. This conclusion has been reached primarily because the evaluation has identified concerns with regard to the safety of this active substance, in particular with regard to mammalian toxicology and effects on non-target organisms. In view of the fact that Hickson and Welch Ltd, the sole remaining notifier of the substance, formally withdrew its support for tecnazene within the EU Peer Review Programme and, therefore, no engagements are made to produce the necessary supplementary data, an inclusion of this active substance in Annex I of Directive 91/414/EEC cannot be envisaged.

毒性情報

Ecotoxicity Values · 5 件

LC50; Species: Asellus aquaticus (Aquatic sowbug, length 7-12 mm); Conditions: freshwater, flow through, 13.0-16.5 °C, pH 7.1-7.3, hardness 50 mg/L CaCO3 (30-78 mg/L), dissolved oxygen 8.8-10.2 mg/L; Concentration: 554 ug/L for 96 hr (95% confidence interval: 342-974 ug/L)

LC50; Species: Gammarus pulex (Scud, length 4-9 mm); Conditions: freshwater, flow through, 13.0-16.5 °C, pH 7.1-7.3, hardness 50 mg/L CaCO3 (30-78 mg/L), dissolved oxygen 8.8-10.2 mg/L; Concentration: 270 ug/L for 96 hr

LC50; Species: Anguilla anguilla (Common eel, length 95-142 mm); Conditions: freshwater, flow through, 13.0-16.5 °C, pH 7.1-7.3, hardness 50 mg/L CaCO3 (30-78 mg/L), dissolved oxygen 8.8-10.2 mg/L; Concentration: 835 ug/L for 14 days (95% confidence interval: 666-1133 ug/L)

LC50; Species: Anguilla anguilla (Common eel, length 95-142 mm); Conditions: freshwater, flow through, hardness 50 mg/L CaCO3 (30-78 mg/L); Concentration: 1400 ug/L for 96 hr

For more Ecotoxicity Values (Complete) data for TECNAZENE (8 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5750(SRC), determined from a log Kow of 4.38(2) and a regression-derived equation(3), indicates that tecnazene is expected to be immobile in soil(SRC). Volatilization of tecnazene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Evaporation of tecnazene from a wet sterilized Yolo fine sandy loam soil after 60, 120, 180, 240, and 300 days was 49.5%, 73.7%, 80%, 85%, and 90.5%, respectively(5). Tecnazene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.8X10-3 mm Hg(6). A first order rate constant of 7.2/day, which corresponds to a half-life of 0.1 day, was reported for a biodegradation screening study utilizing an anaerobic sewage sludge inoculum(7); therefore, tecnazene may biodegrade rapidly in soil under anaerobic conditions. Tecnazene biodegradation was also observed in Yolo fine sandy loam soil(5). After 60, 120, 180, 240, and 300 days incubation at 25 °C, biodegradation values of 8%, 21%, 23%, 26%, and 24% were obtained, respectively, after correction for losses due to volatilization(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5750(SRC), determined from a log Kow of 4.38(2) and a regression-derived equation(3), indicates that tecnazene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.3X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 hours and 8 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 33 months if adsorption is considered(5). According to a classification scheme(6), BCFs of 1362(7), 1600(8) and 2200(8) show bioconcentration in aquatic organisms is very high(SRC). Tecnazene's biodegradation in soil of 90.5% in 300 days(9) suggests that biodegradation in water will be slow(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tecnazene, which has a vapor pressure of 1.8X10-3 mm Hg at 15 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase tecnazene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 6.1 years(SRC), calculated from its rate constant of 7.2X10-15 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Food Survey Values · 4 件

Residues in peanut butter samples: avg: 1.1 ppb; range: 0.42-4.3 ppb (N= 11)

Washing, peeling, and cooking reduced levels of tecnazene in potatoes. Potatoes that had been treated with 3% tecnazene at a rate of 4.5 g/kg were found to contain 3 mg/kg, after 4-5 months storage. Washing reduced the levels of tecnazene to below 1 mg/kg. Another 50% loss of tecnazene occured when the peeled potatoes were boiled. Market basket surveys in the USA of about 300 potato samples revealed that 14 samples had detectable residues of tecnazene (ie, 0.0001 mg/kg or more). Trace levels (0.01 mg/kg or less) of tecnazene were found in 15 out of 3,500 samples of USA foodstuffs. Analyses of vegetable products in Belgium and Sweden for tecnazene revealed that most of the lettuce, chicory, mushrooms, carrots, sweet peppers, corn, etc, had levels between 0.001 and 0.01 mg/kg fresh weight.

Composite samples collected for the Food and Drug Administration (FDA) Adult Total Diet Study (10/79-9/80) yielded a tecnazene concn of 0.01 ppm in potato samples(1). Composite samples collected for the FDA Adult Total Diet Study (10/80-3/82) yielded a trace of tecnazene in oil and fat samples, a tecnazene concn of 0.005 ppm in garden fruit samples, and a tecnazene concn range of a trace to 0.099 ppm in potato samples(2). Composite samples collected for the FDA Infant and Toddler Total Diet Study (10/79-9/80) yielded a tecnazene concn of 0.007 ppm in potato samples(3). Composite samples collected for the FDA Infant and Toddler Total Diet Study (10/80-3/82) yielded a tecnazene concn range of 0.004 to 0.048 ppm in potato samples and a trace of tecnazene in oil and fat samples(4). Tecnazene was qualitatively identified in 2% of all food samples tested during the Food and Drug Administration pesticide residue monitoring of various food samples for the test periods of 1978-1982(5) and 1983-1986(6).

Results from the Danish national pesticide monitoring program of 1995-1996 found tecnazene in green onions; commodities that had no tecnazene detected were grapefruit, lemon, mandarin/clementine, orange, apple, pear, quince, apricot, cherry, peach, nectarine, plum, grape, strawberry, blackberry, Boysen berry, elderberry, raspberry, rowan berry, bilberry, red current, black current, gooseberry, banana, fig, kiwi, pomegranate, beet root, carrot, celeriac, horseradish, parsnip, parsley root, radish, garlic, onion, tomato, pepper, eggplant, cucumber, melon, squash, sweet corn, broccoli, cauliflower, Brussel sprout, (white, red, spring, Oxheart, Chinese) cabbage, kale, lettuce, spinach, chive, dill, marjoram, oregano, parsley, rosemary, thyme, bean, pea, celery, leek, rhubarb, mushroom, sunflower seed, potato(1). A ten-year study of ready-to-eat foods in the US, 1982-1991, found tecnazene 76 times in 22 foods, with an average concn of 5.7 ng/g, the foods were; vegetable with turkey or chicken baby food, boiled mature lima bean, cucumber, cooked frankfurter, plain granola, brown gravy, creamy peanut butter, peanuts, pecans, blueberry or plain muffin, raw sweet green pepper, potato chips, baked potato, boiled potato, french fries, scalloped potato, instant chocolate pudding, dried raisins, winter squash, beef and vegetable stew, baked sweet potato, mixed canned vegetables(2).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Average Daily Intake · 1 件

The Average Daily Intake of tecnazene in 8 population groups for the periods 1982-1984, 1984-1986, 1986-1991, 1992 and 3 population groups for 1988 was determined according to the FDA's monitoring program for chemical contaminants in the U.S. food supply (Total Diet Study or Market Basket Study)(1-5). For the monitoring period of 1982-1984, the AVDI in 6-11 month old infants, 2 year old toddlers, 14-16 year old females, 14-16 year old males, 25-30 year old females, 25-30 year old males, 60-65 year old females, and 60-65 year old males, was 6.7, 17.8, 6.8, 7.0, 6.3, 7.1, 6.1, and 6.7 ng/kg-body weight/day, respectively(1). For the monitoring period of 1984-1986, the AVDI in 6-11 month old infants, 2 year old toddlers, 14-16 year old females, 14-16 year old males, 25-30 year old females, 25-30 year old males, 60-65 year old females, and 60-65 year old males, was 5.1, 15.4, 6.2, 5.3, 6.9, 6.5, 6.8, and 6.8 ng/kg-body weight/day, respectively(2). For the monitoring period of 1988, the AVDI in 6-11 month old infants, 14-16 year old males, and 60-65 year old females, was 0.3, 0.2, and 0.2 ng/kg-body weight/day, respectively(3). For the monitoring period of 1986-1991, the AVDI in 6-11 month old infants, 2 year old toddlers, 14-16 year old females, 14-16 year old males, 25-30 year old females, 25-30 year old males, 60-65 year old females, and 60-65 year old males, was 0.1, 0.2, 0.1, 0.1, 0.1, 0.1, 0.1, and 0.1 ng/kg-body weight/day, respectively(4). For the monitoring period of 1992, the AVDI in 6-11 month old infants, 2 year old toddlers, 14-16 year old females, 14-16 year old males, 25-30 year old females, 25-30 year old males, 60-65 year old females, and 60-65 year old males, was 0.1, 0.2, 0.1, 0.1, 0.1, 0.1, 0.1, and 0.1 ng/kg-body weight/day, respectively(5).

Ecotoxicity Excerpts/OTHER TERRESTRIAL SPECIES/ Not toxic to bees.
Soil Adsorption/MobilityThe Koc of tecnazene is estimated as 5750(SRC), using a log Kow of 4.38(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that tecnazene is expected to be immobile in soil.
Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ Occupational dermal sensitivity has been reported in agricultural workers.
Artificial Pollution Sources · 2 件

TETRACHLORONITROBENZENE, AN IMPURITY OF PENTACHLORONITROBENZENE, 0.06% HAS BEEN FOUND IN TERRACLOR.

Tecnazene's production may result in its release to the environment through various waste streams; its former use in the US as fungicide and growth regulator(1) will have resulted in its direct release to the environment(SRC). As a technical impurity of pentachloronitrobenzene (PCNB), tecnazene may be released to the environment during PCNB production and use(2).

Environmental Biodegradation · 2 件

AEROBIC: Tecnazene biodegradation was observed in Yolo fine sandy loam soil(1). After 60, 120, 180, 240, and 300 days incubation at 25 °C, biodegradation values of 8%, 21%, 23%, 26%, and 24% were obtained, respectively, after correction for losses due to volatilization(1).

ANAEROBIC: A first order rate constant of 7.2/day, which corresponds to a half-life of 0.1 day, was reported for a biodegradation screening study utilizing an anaerobic sewage sludge inoculum(1). The major product for anaerobic biodegradation of tecnazene is 2,3,5,6-tetrachloroaniline(1). The redox potential of the anaerobic system was important in determining how the degradation of tecnazene proceeds(1). It was reported that tecnazene biodegradation did not proceed if the redox potential decreased below -0.38 volts relative to an SCE electrode(1).

Sediment/Soil Concentrations · 1 件

SOIL: Soil from a cabbage field which had been annually treated with pentachloronitrobenzene at 60 kg/ha for a few years was collected 3 months after the final application and analyzed for pentachloronitrobenzene and related compounds. Pentachloronitrobenzene, pentachloroaniline, 2,3,4,5-tetrachloroaniline, methyl pentachlorophenyl sulfide, sulfoxide, sulfone, 2,3,5,5-tetrachloronitrobenzene (tecnazene), pentachloroanisole, hexachlorobenzene, pentachlorobenzene, 1,2,3,4-tetrachlorobenzene, and 1,2,3,5-tetrachlorobenzene were detected at 10.1, 8.05, 0.7, 0.52, 9.35, 1.04, 0.67, 0.009, 1.55, 1.22, 0.009, and 0.011 ppm, respectively.

Environmental BioconcentrationBCFs of 1362(1), 1600(2) and 2200(2) were measured in Lake Ontario rainbow trout. According to a classification scheme(3), these BCF values show bioconcentration in aquatic organisms is very high(SRC).

法規制情報

FIFRA Requirements · 1 件

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. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. 1,2,4,5-Tetrachloro-3-nitrobenzene is found on List B. Case No: 2630; Pesticide type: Fungicide, antimicrobial; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case 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): 1,2,4,5-Tetrachloro-3-nitrobenzene; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled."

安全データ

wgk
3
rtecs
DC0175000
ridadr
UN 3077 9/PG 3
毒性
LD50 oral in rat: 7500mg/kg
hs_code
29049090
risk_code
22-43-50/53
hazard_code
Xn,N
safety_code
24-37-60-61
hazard_class
9
packing_group
III
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Sens. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
117-18-0(Hazardous Substances Data)

Rabbits receiving a single oral dose of 0.1-3.0 g/animal eliminated 60-78% in the feces within 3 days, while the urine accounted for 35-38% (primarily as conjugated products). At 0.01 g/animal, 22-30% was recovered in the feces.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

Used as fungicide and plant growth regulator; to prevent rotting and sprouting of stored potatoes; No longer registered with the EPA for use in the US, cancelled; Registered in the UK for post harvest use on potatoes for long term storage; [HSDB] Used as a fungicide in smoke generators for greenhouses; [INCHEM] Banned for use as pesticide for plant protection and pesticide including biocides in the EU; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

For tecnazene (USEPA/OPP Pesticide Code: 55201) there are 0 label matches. /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 products ... "cancelled."

Plant growth regulator. /Former, US/

Fungicide and growth regulator

Impurities · 2 件

The technical grade material is more than 99% pure and contains less than 1% hexachlorobenzene.

TETRACHLORONITROBENZENE, AN IMPURITY OF PENTACHLORONITROBENZENE, 0.06% HAS BEEN FOUND IN TERRACLOR.

Methods of ManufacturingPRODUCED BY NITRATION OF 1,2,4,5-TETRACHLOROBENZENE ...
Formulations/Preparations · 3 件

Mixed formulations: (technazene +) lindane; thiabendazole; carbendazim.

The technical grade material is more than 99% pure ...

Arena, Fusarex, dustable powder (60 g ai/kg); Arena, Fusarex G, granules (100 g/kg); Tubostore, granules (50 g/kg). Fumite Techalin, smoke generator (tecnazene + gamma-HCH); Fusarex T, suspension concentrate (flowable) (300 g tecnazene + 100 g thiabendazole/l); Storite SS (tecnazene + thiabendazole).

General Manufacturing Information · 1 件

/As of 1994/ The only use of tecnazene now supported /in the UK/ by the manufacturer is the post-harvest application of granular or dust formulations to potatoes. Tecnazene is applied to potatoes for the control of sprouting and the prevention of weight loss in store. It also controls dry rot (Fusarium spp.) and reduces levels of skin spot (Polyscaytalum pustulans), gangrene (Phoma exigua spp.) and silver scurf (Helminthosporium solani). Tecnazene is only applied to potatoes, post-harvest, intended for long-term storage (4-6 months). This use is registered in the UK and tecnazene is currently marketed in a range of granular and dust formulations by various UK-based companies. /Former use in UK/

応用分野

用途残留農薬試験用標準品。

一般的な説明Pale yellow crystals.

調製方法

純化方法Crystallise it from aqueous EtOH or H2O. [Beilstein 5 III 617, 5 IV 728.]

上流・下流製品情報

上流原料

Benzene, 1,2,5-trichloro-3,4-dinitro-Benzenamine, 2,5-dichloro-3-nitro-2,5-dichloro-1,3-dinitrobenzene2,4,5-トリクロロアニリンクロラニル1,2,4,5-テトラクロロベンゼン

下流製品

2,3,5,6-テトラクロロフェノール

サプライヤー1 社

DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
補足説明 · 1 件

定義ChEBI: A C-nitro compound that is nitrobenzene in which the four hydrogens located ortho- and para- to the nitro group have been replaced by chlorines. A fungicide used to control dry rot, it is no longer approved for se within the European Union.