2-methyl-4,6-dinitrophenol
Structural formula | ||||||||||||||||
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General | ||||||||||||||||
Surname | 2-methyl-4,6-dinitrophenol | |||||||||||||||
other names |
4,6-Dinitro- o -cresol (DNOC) |
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Molecular formula | C 7 H 6 N 2 O 5 | |||||||||||||||
Brief description |
yellow crystals |
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External identifiers / databases | ||||||||||||||||
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properties | ||||||||||||||||
Molar mass | 198.13 g mol −1 | |||||||||||||||
Physical state |
firmly |
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density |
1.58 g cm −3 |
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Melting point |
87.5 ° C |
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boiling point |
312 ° C |
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Vapor pressure |
16 m Pa (25 ° C) |
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pK s value |
4.31 |
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solubility |
poorly soluble in water:
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safety instructions | ||||||||||||||||
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MAK |
Switzerland: 0.2 mg m −3 (measured as inhalable dust ) |
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Toxicological data | ||||||||||||||||
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).