4,6-Dinitro-2-sec-butylphenol

4,6-Dinitro-2-sec-butylphenol Basic information
Product Name:4,6-Dinitro-2-sec-butylphenol
Synonyms:DINOSEB 100MG NEAT;unicropdnbp;Vertac dinitro weed killer;Vertac general weed killer;Vertac selective weed killer;vertacdinitroweedkiller;vertacgeneralweedkiller;vertacselectiveweedkiller
CAS:88-85-7
MF:C10H12N2O5
MW:240.21
EINECS:201-861-7
Product Categories:DinitrophenolMethod Specific;Alpha sort;D;DAlphabetic;DID - DINPesticides&Metabolites;Herbicides;Oeko-Tex Standard 100;Pesticides;Pesticides&Metabolites
Mol File:88-85-7.mol
4,6-Dinitro-2-sec-butylphenol Structure
4,6-Dinitro-2-sec-butylphenol Chemical Properties
Melting point 55.5°C
Boiling point 382.92°C (rough estimate)
density 1.29
vapor pressure 0.01Pa at 25℃
refractive index 1.6620 (estimate)
Fp >100 °C
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
form neat
pka4.62(at 25℃)
Specific Gravity1
Water Solubility 0.0052 g/100 mL
Merck 13,3317
Stability:Stable. Strong oxidizing agent. Incompatible with reducing agents, combustible material.
LogP1.26 at 22℃
CAS DataBase Reference88-85-7(CAS DataBase Reference)
NIST Chemistry Reference2-Sec-butyl-4,6-dinitrophenol(88-85-7)
EPA Substance Registry SystemDinoseb (88-85-7)
Safety Information
Hazard Codes T;N,N,T,Xn
Risk Statements 24/25-44-50/53-61-62-36-63-43-36/37/38-23/24/25-45-67-40-41-38
Safety Statements 45-53-60-61-36/37-24/25-23-26-36/37/39
RIDADR UN 2810
WGK Germany 3
RTECS SJ9800000
HazardClass 6.1(a)
PackingGroup II
Hazardous Substances Data88-85-7(Hazardous Substances Data)
ToxicityLD50 in adult male, female rats (mg/kg): 27, 28 orally (Gaines, Linder)
MSDS Information
4,6-Dinitro-2-sec-butylphenol Usage And Synthesis
DescriptionDinoseb, also known as dinitrophenol, can adversely affect the energy generating reaction in a cell. No cell will live very long under the influence of high concentrations of dinitrophenol. It makes the body burn enough energy to result in weight loss. During the 1930s, physicians unwittingly prescribed certain types of dinitrophenol as diet pills.
Dow Chemical changed the basic structure of dinitrophenol slightly to produce dinoseb, which was marketed in 1948. Dinoseb was widely used as a contact herbicide against broadleaf weeds.
Dinoseb causes toxicity the same way in plants, animals, and fungi because all cells contain very similar biochemical pathways for creating energy from the breakdown of sugars. Furthermore, photosynthesis in plants relies on an energy transfer system that is also inhibited by dinitrophenol.
Given the high toxicity, EPA concluded that the doses causing the birth defects and the endocrine-disrupting effects were close to worker exposure levels. Thus, under an emergency order issued in 1986, EPA suspended dinoseb’s registration. In August 1990, the EPA banned the burying of dinoseb-contaminated soils in EPA-approved landfills, making incineration the only EPA-approved disposal method for dinoseb-contaminated soil. Incineration is expensive and incomplete, leaving a noncombustible residue as a further hazardous waste and some combustion products that could remain toxic. Therefore, an ex situ soil bioremediation process was developed by the Sabre Processing company. This process is known as the SABRE process; it uses an anaerobic consortium and supplemental carbon source at the field scale to successfully remediate contaminated soils.
Chemical Propertiessolid
UsesThe amine, ammonium salt or acetate ester is used as a contact herbicide for postemergence weed control in cereals, cotton, peas, beans, potatoes, pumpkins, soybeans and strawberries.
UsesDinoseb is used as an herbicide andinsecticide.
UsesDinoseb is used as an herbicide, corn yield enhancer, insecticide, and miticide. It is used as a herbicide in soybeans, a variety of vegetables, fruits, nuts, citrus trees, and with other field crops for control of grasses and broadleaf weeds. It is used as an insecticide in grapes.
DefinitionChEBI: 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.
General DescriptionOrange-brown viscous liquid or orange-brown solid. Orange crystals when pure. Has a pungent odor. Used as a plant growth regulator; insecticide and herbicide.
Reactivity Profile4,6-Dinitro-2-sec-butylphenol is a powerful oxidizing agent. . 4,6-Dinitro-2-sec-butylphenol is dangerously explosive. When not water wet 4,6-Dinitro-2-sec-butylphenol is a high explosive. Dry, the material is easily ignited and 4,6-Dinitro-2-sec-butylphenol 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].
Health HazardExtremely toxic: Probable oral lethal dose is 5-50 mg/kg; between 7 drops and 1 teaspoonful for 70 kg person (150 lb.).
Health HazardDinoseb is a highly toxic compound. Theoral LD50 values in small laboratory animals were between 10 and 25 mg/kg. Acutetoxicity tests on daphnids and fathead minnows showed high toxicity. The LC50 values in both these species are 0.24 and0.17 mg/L, respectively (Gersich and Mayes1986). Pregnant white rabbits treated withdinoseb exhibited maternal toxicity above thedose level of 1 mg/kg/day. At highly toxicdose levels, adverse effects were observedin developing fetuses (Johnson et al. 1988).Oral administration of dinoseb producedtumors in lung and liver in mice.
Fire HazardThis is a dinitrophenol herbicide. (Non-Specific -- Dinitrophenol, Flammable Solid). 4,6-Dinitro-2-sec-butylphenol is dangerously explosive. When not water wet 4,6-Dinitro-2-sec-butylphenol is a high explosive. Dry, the material is easily ignited and 4,6-Dinitro-2-sec-butylphenol 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.
Flammability and ExplosibilityNonflammable
Agricultural UsesPlant growth regulator, Herbicide: Dinoseb is a phenolic herbicide used in soybeans, vegetables, fruits and nuts, citrus, and other field crops for the selective control of grass and broadleaf weeds (e.g., in corn). It is also used as an insecticide in grapes, and as a seed crop drying agent. It is produced in emuslifiable concentrates or as water-soluble ammonium or amine salts. It is no longer available in the U.S. Formerly widely used in the UK for the fumigation of potatoes; however, dinoseb acetate and dinoseb amine were banned from use in 1988. Dinoseb’s primary use is as a contact herbicide for post-emergence weed control in cereals, undersown cereals, seedling lucerne and peas. Dinoseb is also used as a corn yield enhancer and an insecticide and miticide. Banned for use in EU countries (includes salts and acetate). A U.S. EPA restricted Use Pesticide (RUP). The use of dinoseb was canceled in the U.S. in 1986 based on the potential risk of birth defects and other adverse health effects for applicators and other persons having substantial dinoseb exposure. There are 20 global suppliers.
Trade nameAATOX®; AI3-01122®; ARETIT®; BASANITE®; BNP 20®; BNP 30®; BUTAPHENE®; CALDON®; CASWELL No. 392DD®; CHEMOX®[C]; CHEMOX GENERAL®[C]; CHEMOX P. E. ®[C]; CHEMSECT DNBP®; DESICOIL®; DIBUTOX®; DINITRALL®; DINITRO®; DN 289®; DOW GENERAL®[C]; DOW GENERAL WEED KILLER®[C]; DOW SELECTIVE WEED KILLER®[C]; DYNAMYTE®[C]; DYTOP®; ELGETOL 318®; FANICIDE®; GEBUTOX®; HEL-FIRE®[C]; HIVERTOX®; HOE 26150®; IVOSIT®; KILOSEB®; KNOWX-WEED®; KNOX-WEED®; LADOB®; LASEB®; LIRO DNBP®; NITROPONE C®; PERSEVTOX®; PHENOTAN®; PREMERGE®; SINOX GENERAL®[C]; SPARIC®; SPURGE®; SUBITEX®; UNICROP DNBP®; VERTAC DINITRO WEED KILLER®[C]; VERTAC GENERAL WEED KILLER®[C]; VERTAC SELECTIVE WEED KILLER®[C]
Environmental FateBiological. When 14C-labeled dinoseb (5 ppm) was incubated in soil at 25°C for 60 days, 36.0% of the applied amount degraded to 14CO2 (Doyle et al., 1978). Thom and Agg (1975) reported that dinoseb is unlikely to be degraded in conventional sewage treatment processes.
Groundwater. According to the U.S. EPA (1986) dinoseb has a high potential to leach to groundwater.
Plant. When dinoseb on bean leaves was exposed to sunlight, photodegradation resulted in the formation of persistent, polar compounds. The compounds could not be identified by TLC (Matsuo and Casida, 1970).
Chemical/Physical. Reacts with organic and inorganic bases forming water-soluble salts (Worthing and Hance, 1991).
Emits toxic fumes of chlorine when heated to decomposition (Sax and Lewis, 1987).
Toxicity evaluationDinoseb does not ordinarily persist in the soil, but in storage areas or locations where it has been spilled, it persists as a soil and groundwater contaminant. Additionally, release of dinoseb may result primarily from its use as an herbicide on a variety of weeds. Release of dinoseb to soil is expected to result in biodegradation, and dinoseb only weakly adsorbs to soils and therefore leaches to groundwater. However, it may bind more strongly to clay soils, especially at acidic pH. Photolytic degradation 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 sandy loam soil was estimated to be about 100 days. Dinoseb may photodegrade in surface water with a half-life of 14–18 days. Hydrolysis in water may not be important. It is unlikely to undergo significant biodegradation in most natural waters. Volatilization from water is expected to be slow and bioconcentration is expected to be insignificant. Based on its vapor pressure of 8.5 × 10-2mmHg at 20 ℃, dinoseb may exist entirely in the vapor phase in the atmosphere. The half-life for the reaction of vapor phase dinoseb with photochemically generated hydroxyl radicals in the atmosphere was estimated to be 14.1 days. Wet deposition may remove some of the compound from air.
4,6-Dinitro-2-sec-butylphenol Preparation Products And Raw materials
Raw materials2-sec-Butylphenol
Methylparaben Methyl PICRIC ACID Propyl gallate Cyhalofop-butyl 4-tert-Butylphenol Acetonitrile BUTRALIN Phenol Red Polymerization inhibitor ANTHRALIN Buprofezin Basic Violet 1 tert-Butanol Methyl acrylate Propyl butyrate 2,6-DINITROPHENOL 2-Butoxyethanol

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