Dinoseb

• 6 - (1- methylpropyl ) -2,4 -dinitrophenol
• 4,6- Dinitro -o -sec- butylphenol
• Gebutox
• Butyl Yellow
• DNBP
• Hivertox
• (RS ) -2 - (1- methylpropyl ) -4,6 -dinitrophenol (IUPAC)
• ( ±) -2 - (1- methylpropyl ) -4,6 -dinitrophenol

• C10H12N2O5 ( dinoseb )
• C10H11N2NaO5 ( dinoseb - sodium salt)
• C10H15N3O5 ( dinoseb ammonium salt)
• C12H14N2O6 ( dinoseb acetate esters )

• 88-85-7 ( dinoseb )
• 35040-03-0 ( dinoseb - sodium salt)
• 6365-83-9 ( dinoseb ammonium salt)
• 2813-95-8 ( dinoseb acetate esters )

Yellow flammable solid with slight odor

• 240.22 g · mol -1 ( dinoseb )
• 257.24 g · mol ( dinoseb ammonium salt)
• 282.25 g · mol ( dinoseb acetate esters )

Fixed ( dinoseb )

1.27 g · cm -3

• 38-42 ° C ( dinoseb )
• 26-27 ° C ( acetic acid ester dinoseb )

332 ° C

0.01 Pa ( 20 ° C)

4.62 ( dinoseb )

• In most organic solvents, soluble ( dinoseb )
• Soluble in aromatics ( dinoseb acetate esters )

Risk

27-50 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Dinoseb is a chemical compound selected from the group of substituted phenols ( in more detail the dinitrophenols ).

History

The basic chemical form of the compound in the form of dinitro -ortho -cresol was discovered in Germany and patented in 1892 as an insecticide. By 1925, this was used as a herbicide and soon discovered its fungicidal properties. Dow Chemical in 1948 changed the basic structure of 2,4- dinitrophenol or the dinitrocresol (2- methyl -4 ,6-dinitrophenol ) slightly and produced as dinoseb, which was marketed in 1948. On 13 January 1984 the Danish container ship Dana Optima lost on the journey from North Shields ( GB) to Esbjerg (DK) in heavy seas eighty 200 -liter barrels of dinoseb in the North Sea, of which after four months 72 through an extensive search operation partially damaged were recovered. 1986 dinoseb in America was banned by the EPA.

Stereoisomerism

Dinoseb contains the alkyl side chain of a chiral center, it is chiral. Consequently, there are two stereoisomers, (R) -2 - (1- methylpropyl ) -4,6 -dinitrophenol and the mirror image (S) -2 - (1- methylpropyl ) -4,6 -dinitrophenol. The pesticide active ingredient is used as a racemate [ 1:1 mixture of (R ) -form and the ( S)-form ].

Production and representation

Dinoseb is prepared from phenol by the sulfonation of 4 - phenolsulfonic acid, followed by alkylation with 2-butene or isobutanol in the presence of sulfuric acid and then is finally reacted by nitration to the dinitro derivative.

Use

Dinoseb is used as a pesticide. It is also used in the form of its salts and esters ( diethanolamine dinoseb CAS: 53404-43-6, CAS :8048 amine dinoseb -12-2, ammonium dinoseb CAS :6365 -83 -9). A derivative is often used dinoseb (yellow crystals, mp 26-27 ° C, boiling point 170 ° C, CAS: 2813-95-8 ), which also serves as a raw material for the herbicides Premilan and Herbasol. After the plant protection application regulation is a complete ban on the use of dinoseb, its acetate and salts. In Germany, Austria and Switzerland no dinoseb - containing pesticides is approved.

It also serves as a polymerization inhibitor for styrene.

Effect

Dinoseb acts like other dinitrophenols as a decoupler, which ensures that the energy of the terminal oxidation in metabolism can not take place. Normally constructed H gradient can not be produced.

Safety

Dinoseb is classified as toxic to reproduction.

Related compounds

• Binapacryl