Dinobuton

Structural formula
	Structural formula without stereochemistry : ; 1: 1 mixture of enantiomers
General
Surname	Dinobuton
other names	(2- sec -Butyl-4,6-dinitrophenyl) isopropyl carbonate ( IUPAC ) ; 1-methylethyl-2- (1-methylpropyl) -4,6-dinitrophenyl carbonate;
Molecular formula	C 14 H 18 N 2 O 7
Brief description	yellow solid
External identifiers / databases
EC number	213-546-1
ECHA InfoCard	100.012.315
PubChem	13783
ChemSpider	13186
Wikidata	Q1226658
properties
Molar mass	326.31 g mol −1
Physical state	firmly
density	0.9 g cm −3 (bulk density)
Melting point	56-57 ° C
solubility	practically insoluble in water (1 mg l −1 at 20 ° C); soluble in most organic solvents;
safety instructions
H and P phrases	H: 301-410
	P: 273-301 + 310 + 330
Toxicological data	59 mg kg −1 ( LD 50 , rat , oral ) ; 3200 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 0.08 mg kg −1 4h −1 ( LC 50 , rat , inh. ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dinobutone is a 1: 1 mixture of two isomeric chemical compounds from the group of dinitrophenol derivatives.

Extraction and presentation

Dinobutone can be obtained by a two-step reaction of 2-sec-butylphenol with nitric acid and reaction of the intermediate product with isopropyl chloroformate .

properties

Dinobutone is a yellow solid that is practically insoluble in water. In plants and animals it is metabolized to dinoseb .

use

Dinobutone is used as an acaricide and fungicide against common spider mites and powdery mildew . In EU countries such as Germany, Austria and Switzerland, no pesticides containing this active ingredient are approved.

Trade names

Design, Acrex

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on dinobutone in the GESTIS substance database of the IFA , accessed on January 15, 2020(JavaScript required) .
↑ Entry on Dinobutone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.
↑ Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( page 554 in the Google book search).
↑ Entry on Dinobuton 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 .
↑ ^a ^b Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 882 in the Google book search).
^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 1192 in Google book search).
↑ Directorate-General for Health and Food Safety of the European Commission: Entry on dinobutone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.

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

[PPDB-2] Entry on Dinobutone in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 1, 2013.

[ullmann-3] Ullmann's Agrochemicals, Volume 1 . Viley, 2007, ISBN 978-3-527-31604-5 ( page 554 in the Google book search).

[CLP_100.012.315-4] Entry on Dinobuton 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 .

[unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 ( page 882 in the Google book search).

[Roberts-6] Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 ( page 1192 in Google book search).

[PSM-7] Directorate-General for Health and Food Safety of the European Commission: Entry on dinobutone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.