| | 4,6-Dinitro-2-sec-butylphenol Basic information |
| | 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 | | pka | 4.62(at 25℃) | | Specific Gravity | 1 | | Water Solubility | 0.0052 g/100 mL | | Merck | 13,3317 | | Stability: | Stable. Strong oxidizing agent. Incompatible with reducing agents, combustible material. | | LogP | 1.26 at 22℃ | | CAS DataBase Reference | 88-85-7(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Sec-butyl-4,6-dinitrophenol(88-85-7) | | EPA Substance Registry System | Dinoseb (88-85-7) |
| | 4,6-Dinitro-2-sec-butylphenol Usage And Synthesis |
| Description | Dinoseb, 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 Properties | solid | | Uses | The 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. | | Uses | Dinoseb is used as an herbicide andinsecticide. | | Uses | Dinoseb 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. | | Definition | ChEBI: 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 Description | 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. | | Reactivity Profile | 4,6-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 Hazard | Extremely toxic: Probable oral lethal dose is 5-50 mg/kg; between 7 drops and 1 teaspoonful for 70 kg person (150 lb.). | | Health Hazard | Dinoseb 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 Hazard | This 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 Explosibility | Nonflammable | | Agricultural Uses | Plant 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 name | AATOX®; 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 Fate | Biological. 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 evaluation | Dinoseb 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 |
|
