Dinoseb

Structural formula
	Basic structural formula (stereocenter is marked with an * )
General
Surname	Dinoseb
other names	( RS ) -2- (1-methylpropyl) -4,6-dinitrophenol ( IUPAC ) ; 6- (1-methylpropyl) -2,4-dinitrophenol; 4,6-dinitro- o - sec -butylphenol; Gebutox; Butyl yellow; Dibutox; DNBP; Hivertox; Ladob; (±) -2- (1-methylpropyl) -4,6-dinitrophenol;
Molecular formula	C 10 H 12 N 2 O 5 (dinoseb) ; C 10 H 11 N 2 NaO 5 (dinoseb sodium salt ) ; C 10 H 15 N 3 O 5 (dinoseb ammonium salt ) ; C 12 H 14 N 2 O 6 (dinoseb acetic acid ester) ;
Brief description	yellow flammable solid with a faint odor
External identifiers / databases
EC number	201-861-7
ECHA InfoCard	100.001.692
PubChem	6950
ChemSpider	6684
Wikidata	Q415111
properties
Molar mass	240.22 g mol −1 (dinoseb) ; 257.24 g mol −1 (dinoseb ammonium salt) ; 282.25 g mol −1 (dinoseb acetic acid ester) ;
Physical state	solid (Dinoseb)
density	1.27 g cm −3
Melting point	38-42 ° C (Dinoseb) ; 26–27 ° C (dinoseb acetic acid ester) ;
boiling point	332 ° C
Vapor pressure	0.09 Pa (50 ° C)
pK s value	4.62 (dinoseb)
solubility	practically insoluble in water (50 mg l −1 at 20 ° C); soluble in most organic solvents (Dinoseb) ; soluble in aromatics (dinoseb acetic acid ester) ;
safety instructions
H and P phrases	H: 300-311-315-317-318-360Df-410
	EUH: 044
	P: 201-280-301 + 330 + 331 + 310-302 + 352 + 312-305 + 351 + 338-308 + 313
Authorization procedure under REACH	of particular concern : toxic for reproduction ( CMR )
Toxicological data	27–50 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

history

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

Stereoisomerism

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

Dinoseb (2 stereoisomers)
( S ) configuration	( R ) configuration

Extraction and presentation

Dinoseb is produced from phenol by its sulfonation to 4-phenolsulfonic acid , subsequent alkylation with 2-butene or isobutanol in the presence of sulfuric acid and is then converted into the dinitro derivative by nitration .

use

Dinoseb was used as a plant protection product. It has also been used in the form of its salts and esters (Diethanolamine-Dinoseb CAS number: 53404-43-6, Amin-Dinoseb CAS number: 8048-12-2, Ammonium-Dinoseb CAS number: 6365-83-9) . A derivative that is often used is dinoseb acetate (yellow crystals, melting point 26-27 ° C, boiling point 170 ° C, CAS number: 2813-95-8), which is also used as the base for the herbicides Premilan and Herbasol . According to the Plant Protection Application Ordinance, there is a complete ban on the use of Dinoseb, its acetates and salts . A plant protection product containing dinoseb is not permitted in an EU country or in Switzerland.

It also acts as a polymerization inhibitor for styrene .

effect

Like other dinitrophenols, Dinoseb acts as a decoupler, which ensures that the energy production of the end oxidation in the metabolism cannot take place. The normally built up H ⁺ gradient cannot be generated.

safety instructions

Dinoseb is classified as toxic to reproduction.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Dinoseb in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .

↑ ^a ^b ^c ^d ^e The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 556-557, ISBN 978-0-911910-00-1 .

^ Rene P. Schwarzenbach, Philip M. Gschwend, Dieter M. Imboden; Environmental Organic Chemistry, ISBN 0-471-35750-2 .

↑ Entry on Dinoseb in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.

↑ ^a ^b entry to dinitrophenols at Vetpharm, accessed on 25 January 2018th

↑ Allan S. Felsot: Dinoseb - Banned But Not Forgotten, The Tale of an Unusually Hazardous Pesticide . In: Agricultural and Environmental News . 146, 1998.

^ PS Stamp: The Dinoseb Incident. In: Chemical Spills and Emergency Management at Sea: Proceedings of the First International Conference on "Chemical Spills and Emergency Management at Sea", Amsterdam, The Netherlands, November 15-18, 1988 . Springer, 1988, ISBN 0-792-30052-1 , pp. 325-345 ( limited preview in Google book search).

↑ ^a ^b ^c Toxicological assessment of 2- (1-methylpropyl) -4,6-dinitrophenol (Dinoseb) (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.

^ Directorate-General for Health and Food Safety of the European Commission: Entry on Dinoseb, its acetate and salts in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 17, 2016.

Web links

Maximum Residue Quantity Ordinance ( BGBl. 2005 I p. 105 ) (PDF; 89 kB)

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on Dinoseb in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .

[MERCK_Index-2] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; Pp. 556-557, ISBN 978-0-911910-00-1 .

[3] Rene P. Schwarzenbach, Philip M. Gschwend, Dieter M. Imboden; Environmental Organic Chemistry, ISBN 0-471-35750-2 .

[CLP_100.001.692-4] Entry on Dinoseb in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[SVHC-5] Entry in the SVHC list of the European Chemicals Agency , accessed on July 17, 2014.

[vetpharm-6] try to dinitrophenols at Vetpharm, accessed on 25 January 2018th

[7] Allan S. Felsot: Dinoseb - Banned But Not Forgotten, The Tale of an Unusually Hazardous Pesticide . In: Agricultural and Environmental News . 146, 1998.

[8] PS Stamp: The Dinoseb Incident. In: Chemical Spills and Emergency Management at Sea: Proceedings of the First International Conference on "Chemical Spills and Emergency Management at Sea", Amsterdam, The Netherlands, November 15-18, 1988 . Springer, 1988, ISBN 0-792-30052-1 , pp. 325-345 ( limited preview in Google book search).

[bgc-9] Toxicological assessment of 2- (1-methylpropyl) -4,6-dinitrophenol (Dinoseb) (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 22, 2012.