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Home > Encyclopedia > 1,2,4,5-Tetrachloro-3-nitrobenzene

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

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

1,2,4,5-Tetrachloro-3-nitrobenzene 

structure
  • CAS No:

    117-18-0

  • Formula:

    C6HCl4NO2

  • Chemical Name:

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

  • Synonyms:

    Benzene,1,2,4,5-tetrachloro-3-nitro-;1,2,4,5-Tetrachloro-3-nitrobenzene;Chipman 3142;Folosan DB 905;Fusarex;TCNB;Tecnazene;2,3,5,6-Tetrachloronitrobenzene;2,3,5,6-Tetrachloro-1-nitrobenzene;Folosan;Tecnazen;Myfusan;Tetrachloronitrobenzene;Napotate;Nebulin;1-Nitro-2,3,5,6-tetrachlorobenzene;TCNB (pesticide);NSC 10235;1135443-71-8

  • Categories:

    Agrochemicals  >  Fungicides

Description

beige fine crystalline powderChEBI: A C-nitro compound that is nitrobenzene in which the four hydrogens located ortho- and para- to the nitro group have been replaced by chlorines.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.Pale yellow crystals.


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


2,3,5,6-tetrachloronitrobenzene appears as pale yellow crystals. (NTP, 1992)|Tecnazene is a C-nitro compound that is nitrobenzene in which the four hydrogens located ortho- and para- to the nitro group have been replaced by chlorines.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 use within the European Union. It has a role as an antifungal agrochemical. It is a C-nitro compound, a tetrachlorobenzene and an aromatic fungicide. It derives from a 1,2,4,5-tetrachlorobenzene.

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

260.89

260.89

204-178-2

02X6KNJ5EE

10235

DTXSID0026098

Colorless crystals

29049090

Characteristics

45.8

4.38

Crystalline

1.744 g/cm3 @ Temp: 25 °C

99-100 °C

304 °C

143.1±26.5 °C

1.6200 (estimate)

0.00209 mg/mL at 20 °C

0-6°C

0.0018 mm Hg at 15 deg C (est)

Oral-Rat LD50: 7500 mg/kg

Combustion produces toxic chloride and nitrogen oxide gases

ODORLESS

Henry's Law constant = 2.34X10-5 atm-cu m/mole at 25 °C (est)

Very stable to acids and bases. Stable to heat up to almost 300 °C. In solution, decomposes slowly when exposed to UV radiation.|Hydroxyl radical reaction rate constant = 7.20X10-15 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

This compound will behave as a weak oxidizer, and will react with strong reducing agents including hydrides, sulfides and nitrides.

Non corrosive at room temp

Safety Information

III

9

UN 3077 9/PG 3

3

22-43-50/53

24-37-60-61

DC0175000

Xn,N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Very stable to acids and bases. Stable to heat up to almost 300 deg C.

P273-P280-P501

H302-H317-H410

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/

WHO; Environ Health Criteria 42: Tecnazene (1984)

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

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 131 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

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/

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/

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/

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.

Toxicity

practically nontoxic

LD50 Rat ip 3500 mg/kg|LD50 Rat oral 250 mg/kg|LD50 Rat oral 7500 mg/kg bw

/OTHER TERRESTRIAL SPECIES/ Not toxic to bees.

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).

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).

/Tecnazene/ decomposes slowly in solution, when exposed to ultraviolet radiation.|The rate constant for the vapor-phase reaction of tecnazene with photochemically-produced hydroxyl radicals has been estimated as 7.2X10-15 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 6.1 years at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

1.70e+03|BCFs 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).

1.12e+04 L/kg|The 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.

Tecnazene is rapidly lost from sandy soil ... mainly because of its volatility.|The Henry's Law constant for tecnazene is estimated as 2.3X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that tecnazene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 10 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 8 days(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(3). 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(4). Tecnazene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.8X10-3 mm Hg(5).

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).

Occupational exposure and general population exposure should be low or non-existent since tecnazene is no longer produced or used in the US (Spring, 1998). In the past, tecnazene was applied directly to warehoused produce as a dispersible powder or in smoke formulations and exposure to this compound was primarily by dermal and inhalation in the storage facilities where it was applied. (SRC)|Exposure to the general population is expected to be mainly via residues in food.

Drug Information

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.|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.

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.

3.09 Days

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.

ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. When heated to decomposition it emits toxic fumes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/OTHER TOXICITY INFORMATION/ Occupational dermal sensitivity has been reported in agricultural workers.

2,3,5,6-tetrachloronitrobenzene

1,2,4,5-Tetrachloro-3-nitrobenzene Use and Manufacturing

Methods of Manufacturing

PRODUCED BY NITRATION OF 1,2,4,5-TETRACHLOROBENZENE ...

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).

/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/

MACRO: EXTRACT WITH ETHER, CHECK MP. MICRO: (A) REACTION WITH TETRAETHYLAMMONIUM HYDROXIDE IN ANHYDROUS ACETONE GIVES PURPLISH COLOR WITH ABSORPTION MAX AT 548 NM; COMPARE WITH STANDARDS.|MICRO: (B) ACETONE SOLN TREATED WITH ALCOHOLIC POTASSIUM HYDROXIDE & NITRITE PRODUCED USED TO PREPARE AN AZO-DYE. (C) POLAROGRAPHIC METHOD. (D) BY METHANOLYSIS TO NITRITE ION IN 0.1 N SODIUM METHOXIDE.|RESIDUES ARE EXTRACTED WITH ETHYL ACETATE. AN INTERNAL STD IS ADDED. THE EXTRACTS ARE DILUTED WITH N-HEXANE & ANALYZED BY AUTOMATED GAS LIQUID CHROMATOGRAPHY.|AQUEOUS CHROMOUS CHLORIDE WAS USED TO CARRY OUT THE REDUCTION OF THE NITROGEN DIOXIDE GROUP TO AMINE IN NITROGEN DIOXIDE-CONTAINING HERBICIDES. THE PRODUCTS WERE ANALYZED BY GAS LIQUID CHROMATOGRAPHY WITH ELECTROLYTIC CONDUCTIVITY DETECTION.|For more Analytic Laboratory Methods (Complete) data for TECNAZENE (8 total), please visit the HSDB record page.

A high-performance liquid chromatographic method was developed for the determination of tetrachloronitrobenzene, in flesh fortified at 0.16-53.5 ppm. Trichloronitrobenzene analyzed on a Bondapak C18 column with UV detection at 210 nm. The mobile phase was acetonitrile-methanol-water (35:35:30) at a flow rate of 1.0 ml/min. Retention time was extracted by blending for 5 min in acetone. Samples at 1 ppm were directly injected; samples < 1 ppm were partitioned into hexane followed by passage through an alumina column. Average recoveries varied from 85.6-96.8% with coefficients of variation ranging from 2.18-11.68%. A study conducted to test 23 pesticides for possible interferences with trichloronitrobenzene demonstrated that none of them co-chromatographed. The lower limit of detection was 0.08 ppm.

Agrochemicals -> Fungicides, Plant Growth Regulators

Computed Properties

Molecular Weight:260.9
XLogP3:3.9
Hydrogen Bond Acceptor Count:2
Exact Mass:260.873189
Monoisotopic Mass:258.876139
Topological Polar Surface Area:45.8
Heavy Atom Count:13
Complexity:195
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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