88-85-7

Usage

Uses

Used in Agricultural Industry:
4,6-Dinitro-2-sec-butylphenol is used as a contact herbicide for post-emergence weed control in cereals, cotton, peas, beans, potatoes, pumpkins, soybeans, and strawberries. It is also used as a plant growth regulator, corn yield enhancer, insecticide, and miticide.
Used in Various Crops:
4,6-Dinitro-2-sec-butylphenol is used as a herbicide in soybeans, a variety of vegetables, fruits, nuts, citrus trees, and other field crops for the control of grasses and broadleaf weeds. It is also used as an insecticide in grapes.
Chemical Properties:
4,6-Dinitro-2-sec-butylphenol is a solid with a pungent odor. It is produced in emulsifiable concentrates or as water-soluble ammonium or amine salts.
Regulatory Status:
Dinoseb was banned for use in the U.S. in 1986 due to potential risks of birth defects and other adverse health effects. It is also banned for use in EU countries and is a U.S. EPA restricted Use Pesticide (RUP). The EPA suspended its registration in 1986, and in August 1990, the EPA banned the burying of dinoseb-contaminated soils in EPA-approved landfills, making incineration the only EPA-approved disposal method. However, incineration is expensive and incomplete, leading to the development of an ex situ soil bioremediation process known as the SABRE process by the Sabre Processing company.

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

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.

InChI:InChI=1/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3

Upstream product

• 89-72-5 2-sec-butylphenol 
• 36383-18-3 (-)-(R)-2-sec-butylphenol 
• 159650-89-2 (+)-(S)-2-sec-butylphenol 

Downstream Products

• 19921-90-5 (+/-)-1-sec-butyl-2-chloro-3,5-dinitro-benzene 
• 29506-65-8 2-Butoxy-1-sec-butyl-3,5-dinitro-benzene 
• 26075-30-9 Cyclopentancarbonsaeure-2'-sec-butyl-4',6'-dinitrophenylester 
• 19325-34-9 DL-2,3-Dichlor-2-methyl-propionsaeure-(2,4-dinitro-6-sec.-butyl-phenyl)-ester 
• 29516-70-9 2-Benzyloxy-1-sec-butyl-3,5-dinitro-benzene 
• 29506-80-7 1-sec-Butyl-2-(2-chloro-benzyloxy)-3,5-dinitro-benzene 
• 29506-63-6 1-sec-Butyl-3,5-dinitro-2-propoxy-benzene 
• 29506-67-0 1-sec-Butyl-2-dodecyloxy-3,5-dinitro-benzene 
• 29506-61-4 2-Allyloxy-1-sec-butyl-3,5-dinitro-benzene 
• 29506-62-5 1-sec-Butyl-3,5-dinitro-2-prop-2-ynyloxy-benzene 
• 29506-68-1 1-sec-Butyl-2-(4-chloro-benzyloxy)-3,5-dinitro-benzene 
• 29506-69-2 1-sec-Butyl-2-(3-chloro-benzyloxy)-3,5-dinitro-benzene 
• 29506-84-1 1-sec-Butyl-2-(2,4-dichloro-benzyloxy)-3,5-dinitro-benzene 
• 29506-81-8 1-sec-Butyl-3,5-dinitro-2-(4-nitro-benzyloxy)-benzene 

Relevant academic research and scientific papers

Method for preparing 2,4-dinitro-6-sec-butylphenol through nitration by waste nitric acid

The invention discloses a method for preparing 2,4-dinitro-6-sec-butylphenol through nitration by waste nitric acid, and belongs to the technical field of organic synthesis. According to method, o-sec-butyl phenol is taken as an initial raw material, and excessive nitric acid is added to directly carry out a nitration reaction to generate 2,4-dinitro-6-sec-butylphenol. The excessive acid after thereaction is a dilute nitric acid water solution, the acid content is calibrated, and then a certain amount of concentrated nitric acid is added for directly synthesizing 2,4-dinitro-6-sec-butylphenolof a next kettle. By adopting the method disclosed by the invention, the 2, 4-dinitro-6-sec-butylphenol can be prepared in a pressure kettle, the dilute nitric acid is recycled, the operation is simple, energy is saved, and pollution of waste acid and wastewater is avoided. The process is simple, energy consumption is low, and the method is suitable for industrial scale production.

SULFONATED NITROPHENOLS AS POLYMERIZATION INHIBITORS

Disclosed herein is a method for inhibiting and retarding the premature polymerization and the polymer growth of ethylenically unsaturated monomers comprising adding to said monomers an effective amount of at least one inhibitor that is a sulfonated nitrophenol of the formula: (I) wherein: R1, R2, and R3 are independently selected from the group consisting of hydrogen, alkyl, NO2, and S03H, provided that at least one of R,, R2, and R3 is NO2 and at least one of R1, R2, and R3 is SO3H. In a preferred embodiment, at least one additional inhibitor selected from the group consisting of nitroxyl compounds, nitrosoanilines, nitrophenols, amines, and mixtures thereof is also added.

4-acylaminopiperidin-N-oxyle

4-Acylaminopiperidine N-oxides Ia where A1 is hydrogen or an organic radical and B1 is a radical IIa STR1 where R1 -R4 are each C1 -C4 -alkyl and R1 and R2, on the one hand, and R3 and R4, on the other hand, may furthermore be bonded to form a 5-membered or 6-membered ring, R5 is H or C1 14 C4 -alkyl and R6 is H or C1 -C18 -alkyl, are used for stabilizing organic materials against the harmful effect of free radicals, particularly in the distillation of monomers which undergo free radical polymerization, especially styrene.

Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide

The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides

5,6-Dihydro-1,2,4,6-thiatriazin-5-one-1,1-dioxides of the formula STR1 where R1 is hydrogen, a metal atom or an unsubstituted or substituted ammonium radical, R2 is a saturated or unsaturated straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical or 3 to 7 carbon atoms, a branched saturated or unsaturated aliphatic radical of 3 to 10 carbon atoms, a halogen-, alkoxy- or alkylmercapto-substituted aliphatic radical of 2 to 10 carbon atoms tetrahydrofuryl substituted methyl, a cycloalkoxy-substituted aliphatic radical of 4 to 10 carbon atoms, unsubstituted or halogen-substituted benzyl or phenyl, halophenyl, or alkylphenyl of a total of up to 10 carbon atoms, R3 is hydrogen, a straight-chain aliphatic radical of up to 10 carbon atoms, a cycloaliphatic radical of 3 to 7 carbon atoms, a branched aliphatic radical of 3 to 10 carbon atoms, haloalkyl, or alkoxyalkyl of 2 to 10 carbon atoms and X is oxygen and may also be sulfur if R2 is unsubstituted or halogen-substituted benzyl, processes for their preparation, and herbicides containing the above compounds.

Certain ethers of certain di and trihalo-1-hydroxy-2-(fluoroalkyl)1H-imidazo(4,5-b)pyridine derivatives

Ethers of di and trihalo-1-hydroxy-2-(1,1-difluoroalkyl)-1H-imidazo(4,5-b)pyridine compounds, useful as herbicides and rodenticides.

Alkyl 4-[o-(substituted methyleneamino)-phenyl]-3-thioallophanate miticides and fungicides

Various alkyl 4-[o-(substituted methyleneamino)phenyl]3-thioallophanates are useful as fungicides and mite ovicides. The compounds are prepared by reacting alkyl 4-(o-aminophenyl)-3-thioallophanates with aldehydes or trialkyl orthoformates. Some of the compounds are prepared by further reacting the reaction product of an alkyl 4-(o-aminophenyl)-3-thioallophanate and a trialkyl orthoformate with a primary or secondary amine. Exemplary species are methyl 4-[o-(o-fluorobenzylideneamino)phenyl]-3-thioallophanate, methyl 4-[o-(4-methylbenzylideneamino)phenyl]-3-thioallophanate and methyl 4-[o-(2-furfurylideneamino)phenyl]-3-thioallophanate.

Alkyl 4-[o-(substituted methyleneamino)phenyl]-3-thioallophanates

Various alkyl 4-[o-(substituted methyleneamino)phenyl] 3-thioallophanates are useful as fungicides and mite ovicides. The compounds are prepared by reacting alkyl 4-(o-aminophenyl)-3-thioallophanates with aldehydes or trialkyl orthoformates. Some of the compounds are prepared by further reacting the reaction product of an alkyl 4-(o-aminophenyl)-3-thioallophanate and a trialkyl orthoformate with a primary or secondary amine. Exemplary species are methyl 4-[o-(o-fluorobenzylideneamino)phenyl]-3-thioallophanate, methyl 4-[o-(4-methylbenzylideneamino)phenyl]-3-thioallophanate and methyl 4-[o-(2-furfurylideneamino)phenyl]-3-thioallophanate.

Esters of 1-hydroxy-1H-imidazo-(4,5-b)-pyridines as herbicides

Ethers and esters of 1-hydroxy-2-(1,1-difluoroalkyl)-1H-imidazo(4,5-b)pyridine compounds, useful as herbicides.

1H-imidazo(4,5,-b)-pyridine derivatives

Ethers and esters of 1-hydroxy-2-(1,1-difluoroalkyl)-1H-imidazo(4,5-b)pyridine compounds, useful as herbicides.