Dinoseb
-
Dinoseb
structure -
-
CAS No:
88-85-7
-
Formula:
C10H12N2O5
-
Chemical Name:
Dinoseb
-
Synonyms:
Phenol,2-(1-methylpropyl)-4,6-dinitro-;Phenol,2-sec-butyl-4,6-dinitro-;2-(1-Methylpropyl)-4,6-dinitrophenol;BNP 30;DN 289;Butaphene;2-sec-Butyl-4,6-dinitrophenol;Chemox P.E.;4,6-Dinitro-2-(1-methyl-n-propyl)phenol;Dinoseb;DNOSBP;DNSBP;Dow General;4,6-Dinitro-2-sec-butylphenol;4,6-Dinitro-o-sec-butylphenol;BNP 20;Dibutox;DNBP;Liro DNBP;2,4-Dinitro-6-sec-butylphenol;DBNF;WSX 8365;2,4-Dinitro-6-(1-methylpropyl)phenol;Dytop;Laseb;Aatox;Hivertox;Ladob;Desicoil;6-sec-Butyl-2,4-dinitrophenol;Butaphen;Premerge;Blaartox;4,6-Dinitro-2-(2-butyl)phenol;Dibutox 20CE;NSC 202753;Super Kabrol;39403-80-0;152212-20-9
- Categories:
-
CAS No:
Description
solid
Dinoseb appears as orange-brown viscous liquid or orange-brown solid. Orange crystals when pure. Has a pungent odor. Used as a plant growth regulator; insecticide and herbicide. (EPA, 1998)|Liquid; OtherSolid|Solid|ORANGE CRYSTALS WITH PUNGENT ODOUR.
Dinoseb appears as orange-brown viscous liquid or orange-brown solid. Orange crystals when pure. Has a pungent odor. Used as a plant growth regulator; insecticide and herbicide. (EPA, 1998)|2-(butan-2-yl)-4,6-dinitrophenol is a dinitrophenol that is 2,4-dinitrophenol substituted by a butan-2-yl group at position 2.
Dinoseb Basic Attributes
240.21
240.21
201-861-7
0149
202753
2779|2902
DTXSID3020207
Yellow crystals|Orange solid
2908999090
Characteristics
112
3.69
Dinoseb appears as orange-brown viscous liquid or orange-brown solid. Orange crystals when pure. Has a pungent odor. Used as a plant growth regulator; insecticide and herbicide. (EPA, 1998)
1.2647 g/cm3 @ Temp: 45 °C
38-42 °C
332 °C
>100 °C
1.589
H2O: 0.0052 g/100 mL;Solubility in water, g/100ml at 20°C: 0.005 (very poor)
2-8°C
Vapour pressure, Pa at 20°C: 0.007
Relative vapour density (air = 1): 8.3
Oral-Rat LD50: 25 mg/kg; Oral-Mouse LD50: 16 mg/kg
Combustion produces toxic nitrogen oxides and chloride gases
PUNGENT ODOR
AN ACIDIC PHENOL
PKA 4.62
FORMS SALTS, SOME OF WHICH ARE WATER SOLUBLE, WITH INORGANIC & ORGANIC BASES|Technical: red-brown liquid|Highly water soluble as alkali salts.|The absorption maximum of dinoseb in water is 375 nm.
No rapid reaction with air. No rapid reaction with water.
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Explosive
DINOSEB is a powerful oxidizing agent. (NTP, 1992). It is dangerously explosive. When not water wet it is a high explosive. Dry, the material is easily ignited and it will burn very vigorously. On decomposition, nitro compounds such as this emit toxic fumes. Appear to be stable in acid solution, but are susceptible to decomposition by ultraviolet radiation in alkaline solution. [EPA, 1998].
CORROSIVE TO MILD STEEL IN THE PRESENCE OF WATER|Formulations are noncorrosive to equipment if cleaned after use.
Safety Information
II
6.1(a)
UN 2810
3
24/25-44-50/53-61-62-36-63-43-36/37/38-23/24/25-45-67-40-41-38
45-53-60-61-36/37-24/25-23-26-36/37/39
SJ9800000
T;N,N,T,Xn
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable. Strong oxidizing agent. Incompatible with reducing agents, combustible material.
P201-P280-P301 + P310 + P330-P305 + P351 + P338 + P310-P308 + P313
H300-H311-H315-H317-H318-H360-H410
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P020, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|Dinoseb is a good candidate for liquid injection incineration, with a temp range of 650 to 1,600 °C and a residence time of 0.1 to 2.0 seconds. Also, a good candidate for rotary kiln incineration, with a temp range of 820 to 1,600 °C with a residence time of seconds. Also, a good candidate for fluidized bed incineration, with a temp range of 450 to 980 °C and a residence time of seconds.|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/|Incineration is suggested at 1000 °C (2.0 sec minimum) with adequate scrubbing equipment for the removal of NO(x). Recommendable method: Incineration. Not recommendable method: Hydrolysis. Peer-review: Alkaline and acid hydrolysis not recommendable due to toxicity of the reaction products. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
REISH DJ ET AL; J WATER POLLUT CONTROL FED 50 (6): 1424-69 (1978). ACUTE TOXICOLOGICAL EFFECTS OF DINOSEB ARE DISCUSSED & BIOACCUMULATION & ENVIRONMENTAL RESIDUES OF VARIOUS PESTICIDES ARE REVIEWED.|LAFORNARA JP; J WATER POLLUT CONTROL FED 50 (4): 617-27 (1978). SEVERAL CASE HISTORIES OF ACTUAL EPA FIELD OPERATIONS IN RESPONSE TO TOXIC CHEM SPILLS ARE DISCUSSED. SOME OF THESE INCL SPILLS OF DINITROBUTYLPHENOL (DINOSEB).|BOVEY RW; CH09: 301-56 (1980). CURRENT RESEARCH ON THE FATE & PERSISTENCE OF DINOSEB IN THE ENVIRONMENT IS REVIEWED.|USEPA; Drinking Water Criteria Document: Dinoseb (1990) NTIS/PB90-215385.|USEPA; Health Advisories for 50 Pesticides (1988) NTIS/PB88-113543. These documents summarize the health effects of 50 pesticides including: ... dinoseb ... . Topics discussed include: general information and properties, pharmacokinetics, health effects in humans and animals, quantification of toxicological effects, other criteria guidance and standards, analytical methods, and treatment technologies.
This is a dinitrophenol herbicide. (Non-Specific -- Dinitrophenol, Flammable Solid). It is dangerously explosive. When not water wet it is a high explosive. Dry, the material is easily ignited and it will burn very vigorously. On decomposition, nitro compounds such as this emit toxic fumes. Appear to be stable in acid solution, but are susceptible to decomposition by ultraviolet radiation in alkaline solution. (EPA, 1998)|Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion on confinement and exposure to high temperatures.
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P264, P270, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P308+P313, P312, P321, P322, P330, P337+P313, P361, P363, P391, P405, and P501|H300 (17.14%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P262, P264, P270, P271, P272, P273, P280, P281, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 245 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P262, P264, P270, P271, P280, P281, P301+P310, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, and P501
This is a dinitrophenol herbicide. (Non-Specific -- Dinitrophenol, Flammable Solid) Wear self-contained breathing apparatus and full protective clothing. If fire becomes uncontrollable, evacuate for a radius of 5000 feet. This material is a dinitrophenol herbicide. (Non-Specific -- Dinitrophenol, Flammable Solid) Extinguish by flooding with water. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. (EPA, 1998)|Use water spray, foam, powder, carbon dioxide. Combat fire from a sheltered position.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
This is a dinitrophenol herbicide. (Non-Specific -- Dinitrophenol, Flammable Solid) Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water. Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Keep spilled material wet. Do not attempt to sweep up dry material. (EPA, 1998)
For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)
Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning, or by dissolving them in water, or other solvent in the factory environment.
Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Staining of skin & minor irritation by very small amt. ... Mild to moderate irritation ... /of eyes/. Inhalation /of/ dusts may be irritating ...
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Separated from bases and food and feedstuffs. Cool. Keep in a well-ventilated room. Well closed. Store in an area without drain or sewer access.
A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
The substance is irritating to the eyes. The substance may cause effects on the central nervous system. Exposure at high levels could cause death.
The substance may have effects on the hematopoetic system. May cause reproductive toxicity in humans.
NO open flames.
AVOID ALL CONTACT! AVOID EXPOSURE OF ADOLESCENTS AND CHILDREN! IN ALL CASES CONSULT A DOCTOR!
Use ventilation (not if powder), local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
P020; An acute hazardous waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate.
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 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. 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. Dinoseb is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100/10,000 lbs.
P020; As stipulated in 40 CFR 261.33, when dinoseb, 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)).
Dinoseb was detected at a max concn of 44 ug/L in the agricultural drainage water from potatoe fields in Northwestern New Brunswick, Canada(1).
A monitoring survey was conducted from 1985 to 1987 to determine the levels of five pesticides in selected farm ditches leading three rivers in British Columbia, Canada. In 1985, dinoseb was only found once in ditch sediments (July 1985, 22.9 ug/kg). However, in 1987, dinoseb residues were found in ditch sediments at two sites (mean level 81.2 and 108.6 ug/kg). Elevated levels were detected during the wet season of the yr (Dec 1987 and Feb 1988 samples)(1).
Toxicity
most toxic
LD50 Rabbit percutaneous 80 to 200 mg/kg|LD50 Guinea pig acute dermal 100 to 200 mg/kg|LD50 Rat, adult male oral 27 mg/kg|LD50 Rat, adult female oral 28 mg/kg
MOST SEVERE POISONINGS FROM ABSORPTION OF THESE COMPOUNDS HAVE OCCURRED IN WORKERS WHO WERE CONCURRENTLY EXPOSED TO HOT ENVIRONMENTS. /NITROPHENOLIC COMPOUNDS/
Dinoseb is a contact herbicide used as the ammonium or amine salt for post-emergence weed control in cereals, undersown cereals, seedling lucerne and peas(1). Oil solutions of dinoseb are used for pre-emergence control of annual weeds in beans, peas and potatoes, for pre-harvest dessication of hops, leguminous seed crops, potatoes and for control of runners and suckers in strawberries and raspberries(1). Dinoseb is also used as a corn yield enhancer(2) and an insecticide and miticide(3). Therefore, direct release to the environment from these herbicidal applications has occurred(SRC).
TERRESTRIAL FATE: WATER-SOLUBLE SALTS OF DINOSEB ... LEACH READILY IN SOIL. HOWEVER, OIL-SOLUBLE OR WATER-MISCIBLE FORMULATIONS OF DINOSEB MOVED MUCH LESS THAN WATER-SOLUBLE FORMULATIONS.|TERRESTRIAL FATE: Dinoseb is expected to biodegrade in slowly soil. It should bind weakly to soil. Therefore, leaching in soil is possible and dinoseb has been detected in groundwater. However, it may bind more strongly to clay soils, specialy at acidic pH. Photolytic degrdration of dinoseb from soil surface may be important. Volatilization is not expected to be significant. In the absence of volatilization, the half-life of dinoseb in the vadose zone sandy loam soil was estimated to be about 100 days(1).|AQUATIC FATE: Dinoseb may photodegrade in surface water with a half-life of 14-16 days(1). Hydrolysis in water may not be important(1). Volatilization and adsorption to sediments are not expected to be significant. It is unlikely to undergo significant biodegradation in most natural waters(SRC).|ATMOSPHERIC FATE: Based on its vapor pressure of 8.5X10-2 mm Hg at 20 °C(1), dinoseb may exist entirely in the vapor phase in the atmosphere(2). The half-life for the reaction of vapor phase dinoseb with photochemically generated hydroxyl radicals in the atmosphere was estimated to be 4.1 days(3). Due to its water solubility of 52 mg/L at 25 °C(4), some of the atmospheric dinoseb may be removed by wet deposition.|RESULTANT AVERAGE PERSISTENCE OF PHYTOTOXICITY @ RECOMMENDED RATES: 2 TO 4 WK UNDER AVERAGE CONDITIONS OF USE.
The absorption maximum of dinoseb in water is 375 nm(1) and therefore, direct photolysis of dinoseb in water may be significant. The half-life of dinoseb in a sandly loam soil was 14 hrs when exposed to natural sunlight indicating that it is subject to photodegradation in soil(2). In water dinoseb had a half-life of 14-18 days when exposed to natural sunlight(2). Dinoseb is a weak acid (pKa = 4.62(3)) and ionization will occur in alkaline water. Dinoseb was stable to hydrolysis in water in the pH range of 5-9 at 25 °C over a period of 30 days(2). The hydrolysis half-life of dinoseb to soil was estimated to be 30 days(4). This indicates that hydrolysis in soil may be soil-catalyzed. Based on an estimation method(5) and a daily average concn of 5X10+5/cu cm for hydroxyl radicals(5), a half-life of 4.1 days was estimated fo the reaction of vapor phase dinoseb with photochemically produced generated hydroxyl radicals(SRC).
61.66|A bioconcentration factor (BCF) of 68 for dinoseb was estimated from its water solubility (50 mg/L)(1). A BCF of this magnitude suggests that dinoseb will not bioconcentrate significantly(SRC).
501.19 L/kg|The measured soil-sorption coefficient (Koc) of dinoseb is 124(1). A Koc of this magnitude suggests that dinoseb will be highly mobile in soil and may leach to groundwater. A much higher Koc value of 6607 wa obtained at a buffered pH of 3(2). It appears that soil sorption may be pH dependent and at low pH adsorption may be stronger. It has been shown, however, that p-nitrophenol adsorbs strongly to clays through an interaction between the nitro group and the water molecules or metallic cations in the clay(3). Dinoseb may similarly bind to clays at low pH. Experiments with soil thin layer chromatography showed that dinoseb was intermediate to very mobile in silt loam sand loam and silty loam soils(4).
SOME LOSSES ... UNDER SPECIFIC CONDITIONS OF SOIL ACIDITY, HIGH TEMP, & SURFACE SOIL MOISTURE.|The esimated Henry's Law constant of 5.04X10-4 atm cu m/mol(1) suggests that volatilization of dinoseb from water will be slow(2). Some loss of dinoseb may occur from moist soil surface by codistillation specially at high temperature and acidic soil conditions(3). The laboratory-measured evaporation half-life for dinoseb from a soil surface (soil characteristics and environmental conditions not specified) was 26 days(4).
GROUNDWATER: OVER 10 YR 1969-1978, WATERS OF WELLS IN ONTARIO, CANADA WERE ANALYZED BECAUSE OF CONTAMINATION FROM HERBICIDE SPILLAGE IN OR NEAR THE WELL, COMPLAINTS OF IMPAIRED WATER FLAVOR, OR INJURY TO SEEDLING PLANTS MOISTENED WITH WELL WATER. ONE OF THE 3 PARTICULARLY PERSISTENT CONTAMINANTS WAS DINOSEB.|GROUNDWATER: Detected in groundwater of Long Island, NY at concn range 1-5 ug/L(2). The concn of dinoseb in well water 182 days following a spill was 13 mg/L(3) and was over 3000 mg/L after 382 days of spill(3). Qualitatively detected in 11 groundwater samples in CA(4) and 2 groundwater samples in WI(5). It was also detected in groundwater samples in ME, MA and OR(6). In 3 states in US, its median concn in groundwater was 0.7 ug/L with a max concn of 36.7 ug/L(7).|SURFACE WATER: If was found at a concn of 1 ug/L in a Ohio surface water out of 89 surface waters collected from different locations(1). Dinoseb was consistently found in ditch water at farms in British Columbia, Canada at concn from not detected to 20 ug/L(2).
POTENTIAL EXPOSURE OF WORKERS TO DINOSEB SPRAYING CORN & PEA FIELDS WITH BOOM GROUND SPRAYERS: 0.12 MG/HR RESPIRATORY; 88.7 MG/HR DERMAL; TOTAL= 0.57% TOXIC DOSE/HR. /FROM TABLE/|DEATHS HAVE OCCURRED IN SPRAY OPERATORS & PLANNED MEASURES HAVE BEEN INTRODUCED TO PREVENT RISKS TO AGRICULTURAL WORKERS DURING APPLICATION ... .|Exposure of workers to dinoseb is likely during spraying and mixing operations. (SRC)
Drug Information
Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)|Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)|Chemicals used to destroy pests of any sort. The concept includes fungicides (FUNGICIDES, INDUSTRIAL); INSECTICIDES; RODENTICIDES; etc. (See all compounds classified as Pesticides.)
... RATS POISONED BY CONSUMPTION, INHALATION, OR SKIN EXPOSURE TO HERBICIDES DINITROISOPROPYL-(DNPP) AND DINITROBUTYLPHENOL (DNBP) ... LIVER, KIDNEY, SPLEEN AND BLOOD CONTAINED METABOLITES.|FOLIAR ABSORPTION CHARACTERISTICS: PRINCIPALLY DIRECT CONTACT EFFECT. ... NO TRUE TRANSLOCATION. NO RESIDUES HAVE BEEN TRACED TO FOLIAR OR ROOT UPTAKE.|DISPOSITION OF (14)C-DINOSEB WAS DETERMINED IN NONPREGNANT MICE EXPOSED TO TEMP OF 0, 24, & 32 °C. THE /TIME/ PERIOD OF ENVIRONMENTAL TEMP STUDIED (3-24 HR) HAD NO EFFECT ON THE RATE OF DISAPPEARANCE OF DINOSEB FROM PLASMA OR OTHER TISSUES EXAMINED.|AFTER ORAL OR IP ADMIN TO PREGNANT MICE DINOSEB WAS FOUND IN ALL MATERNAL TISSUES & WAS SHOWN TO CROSS THE PLACENTA. RATE OF ABSORPTION WAS 40 TIMES GREATER AFTER IP THAN ORAL ADMIN. DINOSEB WAS EXCRETED IN URINE & FECES, & METABOLITES WERE FOUND IN MATERNAL LIVER & KIDNEY & IN THE EMBRYO.|For more Absorption, Distribution and Excretion (Complete) data for DINOSEB (9 total), please visit the HSDB record page.
A METABOLITE, DINOSEB, WAS FOUND IN CONCN OF 0.34 MG/KG ON 15TH DAY OF EXPOSURE OF YOUNG CARP TO 0.01 MG/L DINOBUTON. FOLLOWING 15-DAY EXPOSURE TO 0.01 MG ACREX/L TO CARP IT DID NOT ACCUMULATE IN THE FISH, BUT A METABOLITE DINOSEB WAS DETECTED @ 0.34 MG/KG.|BIOTRANSFORMATION ... IN RATS & RABBITS YIELDED 2-(2-HYDROXY-1-METHYLPROPYL)-4,6-DINITROPHENOL; 2-METHYL-2-(2-HYDROXY-3,5-DINITROPHENYL)PROPIONIC ACID; 2-AMINO-6-(1-METHYLPROPYL)-4-NITROPHENOL & THE GLUCURONIDE AS URINARY METABOLITES.|PAPER ELECTROPHORESIS OF SERUM OF RATS POISONED BY CONSUMPTION, INHALATION, OR SKIN EXPOSURE TO ... DINOSEB SHOWED DNBP COMPLEXES. LIVER, KIDNEY, SPLEEN, & BLOOD CONTAIN METABOLITES. ALTHOUGH NOT IDENTIFIED, CHEM REACTIONS INDICATED THAT BOTH HERBICIDES WERE ENZYMATICALLY REDUCED IN LIVER TO PRIMARY AMINES. URINE OF RABBITS & RATS FED DNBP AND ITS ESTERS ... COLLECTED ... SIDE CHAIN OXIDN AND NITROGEN REDN WERE OBSERVED. ... /IN/ RABBITS, 5 METABOLITES WERE OBSERVED ... IN ADDITION TO UNCHANGED DNBP, 2-AMINO-4-NITRO-6-SEC-BUTYLPHENOL & ITS GLUCURONIDE, BETA-METHYL-BETA-(2-HYDROXY-3,5-DINITROPHENYL)PROPIONIC ACID & AN UNIDENTIFIED CMPD.|AFTER INCUBATION ... WITH RUMEN FLUID, 6-AMINO-2-BUTYL-4-NITROPHENOL (ABNP) WAS OBSERVED. WITH CONTINUED INCUBATION ... CONCN OF ABNP DIMINISHED & THAT OF 2-SEC-BUTYL-4,6-DIAMINOPHENOL (BDAP) INCREASED. WHEN ... ADMINISTERED TO COWS ... SAME METABOLITES ... OBSERVED AS ... IN VITRO.|For more Metabolism/Metabolites (Complete) data for DINOSEB (6 total), please visit the HSDB record page.
BASIC MECHANISM OF TOXICITY IS STIMULATION OF OXIDATIVE METABOLISM IN CELL MITOCHONDRIA, BY INTERFERENCE WITH NORMAL COUPLING OF CARBOHYDRATE OXIDN TO PHOSPHORYLATION (ADP TO ATP). INCR OXIDATIVE METABOLISM LEADS TO PYREXIA, TACHYCARDIA, & DEHYDRATION, & ULTIMATELY DEPLETES CARBOHYDRATE & FAT STORES. /NITROPHENOLIC COMPOUNDS/|... UNCOUPLER OF OXIDATIVE PHOSPHORYLATION & INCR THE OXIDATIVE METABOLISM & HEAT PRODUCTION OF THE BODY.|The effects of plant herbicides on reaction centers from the photosynthetic bacterium, Rhodopseudomonas sphaeroides, were investigated. A variety of triazine herbicides were good inhibitors of electron transfer reactions involving primary and secondary quinone. Other types of herbicides, including dinoseb, ... were relatively ineffective.|Administration of 2,4-dinitrophenol alkyl derivatives to rats, ie, 4,6-dinitro-o-cresol (DNOC) and dinoseb (60 and 40 mg/kg, respectively) affected the electron transport system and inhibited energy metabolism and the detoxication system of the liver. An ESR study showed lowering of cytochrome p450 of the liver throughout the observation period, changes in the cytochrome c oxidase, lowering of iron-sulfur-containing proteins (54% in 6 hr), and a decrease in the free radical level as compared to the original levels. The metalloprotein and free radicals, observed 30 min after dinoseb, showed a tendency to normalization.|Dinoseb is believed to enhance metabolic activity by uncoupling oxidative phosphorylation and disrupting adenosine triphosphate synthesis ... culminating, in extreme cases, in hyperthermia. In ruminants, dinoseb, an organo-nitro compound, is reduced to an amine, which may then cause the oxidation of hemoglobin to methemoglobin. ...
THE TRIETHANOLAMINE SALT OF DINOSEB CONTAINED OVER 200 MG/KG N-NITROSODIETHANOLAMINE. /SRP: A HIGHLY TOXIC CONTAMINANT/
Extremely toxic: Probable oral lethal dose is 5-50 mg/kg; between 7 drops and 1 teaspoonful for 70 kg person (150 lb.). (EPA, 1998)|Teratogens
Warning: Effects may be delayed from several hours to 2 days. Caution is advised. Toxicity of dinoseb is enhanced by high ambient temperature and physical activity. Signs and Symptoms of Acute Dinoseb Exposure: Early manifestations of dinoseb exposure include fever, sweating, headache, and confusion. Elevations of blood pressure, pulse, and respiratory rate are common. Severe exposure may result in restlessness, seizures, and coma. Other signs and symptoms include dyspnea (shortness of breath), pulmonary edema, nausea, vomiting, and abdominal pain. Liver injury with associated jaundice, kidney failure, and cardiac arrhythmias may be noted. Muscle weakness may be pronounced. Dermal exposure results in yellow staining of the skin and may produce burns. Emergency Life-Support Procedures: Acute exposure to dinoseb may require decontamination and life support for the victims. Emergency personnel should wear protective clothing appropriate to the type and degree of contamination. Air-purifying or supplied-air respiratory equipment should also be worn, as necessary. Rescue vehicles should carry supplies such as plastic sheeting and disposable plastic bags to assist in preventing spread of contamination. Inhalation Exposure: 1. Move victims to fresh air. Emergency personnel should avoid self-exposure to dinoseb. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 4. Transport to a health care facility. Dermal/Eye Exposure: 1. Remove victims from exposure. Emergency personnel should avoid self- exposure to dinoseb. 2. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 3. Remove contaminated clothing as soon as possible. 4. If eye exposure has occurred, eyes must be flushed with lukewarm water for at least 15 minutes. 5. Vigorously wash exposed skin areas with soap and water. Yellowish coloration usually accompanies dermal exposure; the discoloration does not have to be fully removed to prevent further absorption. 6. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 7. Transport to a health care facility. Ingestion Exposure: 1. Evaluate vital signs including pulse and respiratory rate, and note any trauma. If no pulse is detected, provide CPR. If not breathing, provide artificial respiration. If breathing is labored, administer oxygen or other respiratory support. 2. Obtain authorization and/or further instructions from the local hospital for administration of an antidote or performance of other invasive procedures. 3. Vomiting may be induced with syrup of Ipecac. If elapsed time since ingestion of dinoseb is unknown or suspected to be greater than 30 minutes, do not induce vomiting and proceed to Step 4.Ipecac should not be administered to children under 6 months of age.Warning: Ingestion of dinoseb may result in sudden onset of seizures or loss of consciousness. Syrup of Ipecac should be administered only if victims are alert, have an active gag-reflex, and show no signs of impending seizure or coma. If ANY uncertainty exists, proceed to Step 4.The following dosages of Ipecac are recommended: children up to 1 year old, 10 mL (1/3 oz); children 1 to 12 years old, 15 mL (1/2 oz); adults, 30 mL (1 oz). Ambulate (walk) the victims and give large quantities of water. If vomiting has not occurred after 15 minutes, Ipecac may be readministered. Continue to ambulate, and give water to the victims. If vomiting has not occurred within 15 minutes after second administration of Ipecac, administer activated charcoal. 4. Activated charcoal may be administered if victims are conscious and alert. Use 15 to 30 g (1/2 to 1 oz) for children, 50 to 100 g (1-3/4 to 3-1/2 oz) for adults, with 125 to 250 mL (1/2 to 1 cup) of water. 5. Promote excretion by administering a saline cathartic or sorbitol to conscious and alert victims. Children require 15 to 30 g (1/2 to 1 oz) of cathartic; 50 to 100 g (1-3/4 to 3-1/2 oz) is recommended for adults. 6. Transport to a health care facility. (EPA, 1998)
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
In a poisoned person, the result is an almost immediate incr in oxygen consumption, body temp, breathing rate, and heart rate. Because circulation and resp do not accelerate in proportion to the metabolic demand, anoxia and acidosis develop. ... It is a milder corrosive to skin and mucous membrane than phenol, but concentrated soln have produced corrosion of the oropharyngeal, esophageal and gastric mucous membranes; Dinoseb exerts direct actions on the cerebrum and lower brain centers consisting of stimulation followed by depression; It may produce a necrotizing tubular injury of the kidneys. If the acute phase of poisoning is survived, the patient usually tolerates successfully the later complications, which may include renal insufficiency and a toxic hepatitis. The fulminating type of poisoning is characterized by sudden onset, severe symptoms, and prompt death (within 24 hours). Death is due to resp or circulatory collapse, especially the former. Many factors undoubtedly contribute to this collapse, notably hyperpyrexia, ... dehydration, muscle rigor (due to heat and/or lactic acid), and occasionally pulmonary edema. ... In subacute poisoning due to repeated daily exposures, some individuals complain of lassitude, headache, and malaise, while others experience a disarming sense of well-being, energy, and drive. /Dinitrophenol/|YELLOW STAINING OF SKIN & HAIR SIGNIFY CONTACT WITH NITROPHENOLIC CHEMICAL. STAINING OF SCLERAE & URINE INDICATE ABSORPTION OF POTENTIALLY TOXIC AMT. PROFUSE SWEATING, HEADACHE, THIRST, MALAISE, & LASSITUDE ARE COMMON EARLY SYMPTOMS OF POISONING. WARM, FLUSHED SKIN, TACHYCARDIA, & FEVER CHARACTERIZE A SERIOUS DEGREE OF POISONING. APPREHENSION, RESTLESSNESS, ANXIETY, MANIC BEHAVIOR, OR UNCONSCIOUSNESS REFLECT SEVERE CEREBRAL INJURY. ... CYANOSIS, TACHYPNEA & DYSPNEA OCCUR AS CONSEQUENCE OF EXTREME STIMULATION OF METABOLISM, PYREXIA, & TISSUE ANOXIA. WEIGHT LOSS OCCURS IN PERSONS CHRONICALLY POISONED AT LOW DOSAGES. /NITROPHENOLIC COMPOUNDS/|... TOXIC TO LIVER, KIDNEY, & NERVOUS SYSTEM. ... LIVER PARENCHYMA & RENAL TUBULES SHOW DEGENERATIVE CHANGES. ALBUMINURIA, PYURIA, HEMATURIA, & INCR BUN ARE OFTEN PROMINENT SIGNS OF RENAL INJURY. ... DEATH IN NITROPHENOL POISONING IS FOLLOWED PROMPTLY BY INTENSE RIGOR MORTIS. /NITROPHENOLIC COMPOUNDS/|MOST SEVERE POISONINGS FROM ABSORPTION OF THESE COMPOUNDS HAVE OCCURRED IN WORKERS WHO WERE CONCURRENTLY EXPOSED TO HOT ENVIRONMENTS. /NITROPHENOLIC COMPOUNDS/
2,4-dinitro-6-sec-butylphenol
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Sweating. Headache. Laboured breathing. Nausea. Vomiting. Fever. Convulsions. Unconsciousness. Cyanosis
EASILY ABSORBED! Redness. Further see Inhalation.
Redness. Pain.
Dinoseb Use and Manufacturing
PRODUCED BY NITRATION OF 2-SEC-BUTYLPHENOL, OBTAINED BY THE REACTION OF BUT-2-ENE WITH PHENOL & SEPARATION OF THE 4-ALKYL ISOMER.|BY SULFONATION OF PHENOL TO BLOCK p-POSITION, FOLLOWED BY BUTYLATION & REMOVAL OF SULFONIC GROUP.|REACTION OF O-SEC-BUTYLPHENOL WITH SULFURIC ACID & NITRIC ACID
Used as styrene polymerization inhibitor and pesticide intermediate
Process regulators
1,000,000 - 10,000,000 lb|(1978) 3.86X10+9 G (CONSUMPTION-INCL IMPORTS)|(1982) 2.81X10+9 G (CONSUMPTION-INCL IMPORTS)
HERBICIDE FOR SOYBEANS, 32%; VEGETABLES, 23%; DECIDUOUS FRUITS & NUTS, 11%; PEANUTS, 8%; CITRUS, 3%; GRAIN CROPS, 2%; OTHER FIELD CROPS, 6%; INDUSTRIAL/COMMERCIAL USES, 15%. (1982)|Soybeans, 40%; cotton, 15%; potatoes, 16%; peanuts, 9%; alfalfa, 4%; snap beans, 2%; peas, 2%; grapes, 2%; & almonds, 1% (1986; major use sites by volume)
EMULSIFIABLE CONCENTRATE, AQUEOUS SOLUTION & OIL SOLUTION.|The cmpd is usually marketed as soluble sodium, ammonium or alkanolamine salts; the acetylated phenol (dinoseb acetate) & the methacrylate ester (dinoseb methacrylate, also known as binapacryl ...) are also available.
All other basic organic chemical manufacturing|Phenol, 2-(1-methylpropyl)-4,6-dinitro-: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies Dinoseb (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide. The international trade of ... Dinoseb and Dinoseb salts ... is regulated by the Rotterdam convention on Prior Informed Consent (see http://www.pic.int/), which entered force on 24 February 2004. According to the PIC Convention, export of /Dinoseb and Dinoseb salts/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).|... DEVELOPED BY THE DOW CHEMICAL CO UNDER THE CODE NUMBER 'DN289', TRADE MARK 'PREMERGE' & THE PROTECTION OF US PATENT 2,192,197
BY A COLUMN CHROMATOGRAPHIC ... SEPARATION & COLORIMETRY ... RESIDUES ARE DETERMINED BY GLC OF THE METHYL ETHER AFTER CHROMATOGRAPHIC CLEAN-UP & TREATMENT WITH DIAZOMETHANE.|A GAS CHROMATOGRAPHY WITH ELECTRON CAPTURE DETECTION METHOD IS DESCRIBED FOR DETERMINATION OF RESIDUES OF DINOSEB IN CROPS & SOIL AT LEVELS RANGING FROM 0.05 TO 100 PPM. THE METHOD PROVIDES A SENSITIVE MEANS OF QUANTIFYING RESIDUES OF DINOSEB TO 20 PG.|DETERMINATION OF DINOSEB IN WATER BY HIGH PRESSURE LIQUID CHROMATOGRAPHY IS DESCRIBED. DETECTION LIMIT IS 0.6 UG/L.|A COULSON ELECTROLYTIC CONDUCTIVITY DETECTOR WAS USED TO DETECT DINOSEB IN FOODS.|For more Analytic Laboratory Methods (Complete) data for DINOSEB (11 total), please visit the HSDB record page.
GAS CHROMATOGRAPHIC METHODS FOR DETERMINING THE HERBICIDE DNBP IN BLOOD, URINE, FECES & TISSUES OF RATS & IN AGRIC FEED ARE DISCUSSED. AVG RECOVERY WAS 85%.
Health Hazards -> Teratogens|Pharmaceuticals|HERBICIDES
Computed Properties
Molecular Weight:240.21
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:240.07462149
Monoisotopic Mass:240.07462149
Topological Polar Surface Area:112
Heavy Atom Count:17
Complexity:298
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Learn More Other Chemicals
-
Dinoseb ammonium salt
6365-83-9
-
Dinoseb acetate
2813-95-8
-
1-phenyl-3-(1H-1,2,4-triazol-5-yl)urea
55424-82-3
-
Bromopyruvic acid Formula
1113-59-3
-
2-Amino-5-chlorophenol Formula
28443-50-7
-
N-[2-(2,4,6-Trichlorophenoxy)ethyl]-1-propanamine Formula
67747-01-7
-
2-(4-chlorophenyl)-2-methylpropanol Structure
80854-14-4
-
1,6-Hexanediol Structure
629-11-8
-
What is 4-Morpholinamine
4319-49-7
-
What is S-Octyl carbonochloridothioate
13889-96-8