2-methyl-4,6-dinitrophenol

Structural formula
General
Surname	2-methyl-4,6-dinitrophenol
other names	4,6-Dinitro- o -cresol (DNOC)
Molecular formula	C 7 H 6 N 2 O 5
Brief description	yellow crystals
External identifiers / databases
EC number	208-601-1
ECHA InfoCard	100,007,821
PubChem	10800
Wikidata	Q209437
properties
Molar mass	198.13 g mol −1
Physical state	firmly
density	1.58 g cm −3
Melting point	87.5 ° C
boiling point	312 ° C
Vapor pressure	16 m Pa (25 ° C)
pK s value	4.31
solubility	poorly soluble in water: 0.198 g l −1 (20 ° C); 6.94 g l −1 (pH 7 and 20 ° C);
safety instructions
H and P phrases	H: 300-310-330-315-317-318-341-410
	EUH: 044
	P: 260-264-273-280-284-301 + 310
MAK	Switzerland: 0.2 mg m −3 (measured as inhalable dust )
Toxicological data	7 mg kg −1 ( LD 50 , rat , oral ) ; 1000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-methyl-4,6-dinitrophenol , and 4,6-dinitro- o -cresol ( DNOC ), is a doubly nitrated ortho - cresol . It was launched by Bayer in 1892 as the first synthetic insecticide . In 1925 it was also introduced as a herbicide .

properties

2-Methyl-4,6-dinitrophenol forms yellow crystals with a triclinic crystal structure , which are explosive in dry form and melt at 88.2–89.9 ° C. It is highly toxic and can be absorbed through the skin. In animal experiments, 2-methyl-4,6-dinitrophenol shows mutagenic effects. It forms water-soluble salts with alkali metals .

use

2-Methyl-4,6-dinitrophenol is a non-systemic insecticide and acaricide with a contact and pest-poison effect against biting and sucking pests, especially for combating the nun ( Lymantria monacha ) in the forest, as a winter spray ( yellow carbolineum , yellow oil ) against wintering stages of animals Pests used in fruit and wine growing and as an ovicide against spider mites . It is also used as a contact herbicide with a corrosive effect on annual weeds in cereals and maize, and to kill weeds in potato cultivation. Biochemically, like 2,4-dinitrophenol, it acts as a decoupler for oxidative phosphorylation .

It is used as a sodium or ammonium salt with an admixture of at least 10% water.

An alleged use of 2-methyl-4,6-dinitrophenol during the Vietnam War as a defoliant "Agent Yellow" is occasionally mentioned in German-language literature. There is no evidence of this in the English-language specialist press.

Admission

2-Methyl-4,6-dinitrophenol has no longer been approved throughout Europe since 1991.

Trade names

Antinonnin, the first synthetic insecticide, patented by Bayer in 1894 and marketed.
Dinitrol , Etzel : DNOC for use as a herbicide
Selinon (ammonium salt), Dinitrokarbolineum , Dinitrosol-carbolic : DNOC as a winter spraying for orchards

Individual evidence

↑ ^a ^b ^c ^d Entry on DNOC. In: Römpp Online . Georg Thieme Verlag, accessed on May 21, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on DNOC in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b ^c Environmental Health Criteria (EHC) for DINITRO-ortho-CRESOL , accessed on November 19, 2014.
↑ ^a ^b ^c Entry on 2-methyl-4,6-dinitrophenol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Entry on 2-methyl-4,6-dinitro-phenol 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 .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on November 2, 2015.
↑ Wayland J. Hayes Jr: Handbook of Pesticide Toxicology . Classes of Pesticides. Elsevier, 1991, ISBN 978-1-4832-8863-5 ( limited preview in Google Book Search).
↑ Max Daunderer : Clinical Toxicology. Poison information, poison detection, poisoning therapy . ecomed, Landsberg / Lech 1995 to Dec. 2006, ISBN 3-609-70000-9 .
↑ Jeanne Mager Stellman, Steven D. Stellman, Richard Christian, Tracy Weber, Carrie Tomasallo: The extent and patterns of usage of Agent Orange and other herbicides in Vietnam . In: Nature . tape 422 , no. 6933 , March 17, 2003, p. 681-687 , doi : 10.1038 / nature01537 .
^ Pesticides go off with a bang
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.
↑ Blacklisted, therefore with reservation: chemie.de/lexikon/Insektizid.html
↑ Franz Schinner, Renate Sonnleitner: Soil ecology: microbiology and soil enzymes Volume III: Plant protection products, agricultural additives and organic environmental chemicals . Springer-Verlag, 2013, ISBN 978-3-642-59221-8 ( limited preview in Google book search).

[Römpp-1] Entry on DNOC. In: Römpp Online . Georg Thieme Verlag, accessed on May 21, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on DNOC in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[inchem-3] Environmental Health Criteria (EHC) for DINITRO-ortho-CRESOL , accessed on November 19, 2014.

[ChemIDplus-4] Entry on 2-methyl-4,6-dinitrophenol in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[CLP_100.007.821-5] Entry on 2-methyl-4,6-dinitro-phenol 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 .

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values , accessed on November 2, 2015.

[7] Wayland J. Hayes Jr: Handbook of Pesticide Toxicology . Classes of Pesticides. Elsevier, 1991, ISBN 978-1-4832-8863-5 ( limited preview in Google Book Search).

[8] Max Daunderer : Clinical Toxicology. Poison information, poison detection, poisoning therapy . ecomed, Landsberg / Lech 1995 to Dec. 2006, ISBN 3-609-70000-9 .

[Stellman-9] Jeanne Mager Stellman, Steven D. Stellman, Richard Christian, Tracy Weber, Carrie Tomasallo: The extent and patterns of usage of Agent Orange and other herbicides in Vietnam . In: Nature . tape 422 , no. 6933 , March 17, 2003, p. 681-687 , doi : 10.1038 / nature01537 .

[10] Pesticides go off with a bang

[11] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.

[12] Blacklisted, therefore with reservation: chemie.de/lexikon/Insektizid.html

[13] Franz Schinner, Renate Sonnleitner: Soil ecology: microbiology and soil enzymes Volume III: Plant protection products, agricultural additives and organic environmental chemicals . Springer-Verlag, 2013, ISBN 978-3-642-59221-8 ( limited preview in Google book search).