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== Uses ==
== Uses ==
Dinoseb is a herbicide that was once widely used for weed-control when producing crops like soybeans, vegetables, fruits and nuts, or citrus. In the present, dinoseb is banned in the EU and USA due to its high toxicity. However, dinoseb is still used in China for example; evidenced by the fact that it is found in rain- and drinking water. Nowadays there are other, safer herbicides that can be used.<ref name=":1">{{Cite journal|last=Heusinkveld|first=Harm J.|last2=van Vliet|first2=Arie C.|last3=Nijssen|first3=Peter C. G.|last4=Westerink|first4=Remco H. S.|date=2016-06-11|title=In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides|url=https://www.ncbi.nlm.nih.gov/pubmed/27106277|journal=Toxicology Letters|volume=252|pages=62–69|doi=10.1016/j.toxlet.2016.04.014|issn=1879-3169|pmid=27106277}}</ref> Dinoseb was also used as an insecticide to protect grapes. On the internet, dinoseb and other dinitrophenols are bought as weight-loss pills. It is very dangerous however, and many people have died of accidental overdose.<ref>{{Cite journal|last=Zaharia|first=M.|last2=Tudorachi|first2=L.|last3=Pintilie|first3=O.|last4=Drochioi|first4=C.|last5=Gradinaru|first5=R.|last6=Murariu|first6=M.|year=2016|title=Banned dinitrophenols still trigger both legal and forensic issues|url=https://www.researchgate.net/publication/299373270_Banned_dinitrophenols_still_trigger_both_legal_and_forensic_issues|journal=Environmental Forensics|volume=17(1)|pages=120-130|via=}}</ref>
Dinoseb is a herbicide that was once widely used for weed-control when producing crops like soybeans, vegetables, fruits and nuts, or citrus. In the present, dinoseb is banned in the EU and USA due to its high toxicity. However, dinoseb is still used in China for example; evidenced by the fact that it is found in rain- and drinking water. Nowadays there are other, safer herbicides that can be used.<ref name=":1">{{Cite journal|last=Heusinkveld|first=Harm J.|last2=van Vliet|first2=Arie C.|last3=Nijssen|first3=Peter C. G.|last4=Westerink|first4=Remco H. S.|date=2016-06-11|title=In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides|url=https://www.ncbi.nlm.nih.gov/pubmed/27106277|journal=Toxicology Letters|volume=252|pages=62–69|doi=10.1016/j.toxlet.2016.04.014|issn=1879-3169|pmid=27106277}}</ref> Dinoseb was also used as an insecticide to protect grapes. On the internet, dinoseb and other dinitrophenols are bought as weight-loss pills. It is very dangerous however, and many people have died of accidental overdose.<ref name=":2">{{Cite journal|last=Zaharia|first=M.|last2=Tudorachi|first2=L.|last3=Pintilie|first3=O.|last4=Drochioi|first4=C.|last5=Gradinaru|first5=R.|last6=Murariu|first6=M.|year=2016|title=Banned dinitrophenols still trigger both legal and forensic issues|url=https://www.researchgate.net/publication/299373270_Banned_dinitrophenols_still_trigger_both_legal_and_forensic_issues|journal=Environmental Forensics|volume=17(1)|pages=120-130|via=}}</ref>


== Toxicity ==
== Toxicity ==
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Dinoseb can cross biological membranes like the blood-brain barrier and the placental barrier. This explains why dinoseb is particularly dangerous for pregnant women. If the compound can pass the placental barrier, the unborn child will be exposed to dinoseb via the blood of the mother.<ref name=":1" />
Dinoseb can cross biological membranes like the blood-brain barrier and the placental barrier. This explains why dinoseb is particularly dangerous for pregnant women. If the compound can pass the placental barrier, the unborn child will be exposed to dinoseb via the blood of the mother.<ref name=":1" />

Oral LD50 values of Dinoseb range from 14 to 114 mg/kg in rats, mice rabbits and guinea pigs.<ref name=":2" />


==See also==
==See also==

Revision as of 13:54, 13 March 2017

Dinoseb
Names
Preferred IUPAC name
2-(Butan-2-yl)-4,6-dinitrophenol
Other names
2-(sec-Butyl)-4,6-dinitrophenol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.692 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3 checkY
    Key: OWZPCEFYPSAJFR-UHFFFAOYSA-N checkY
  • InChI=1/C10H12N2O5/c1-3-6(2)8-4-7(11(14)15)5-9(10(8)13)12(16)17/h4-6,13H,3H2,1-2H3
    Key: OWZPCEFYPSAJFR-UHFFFAOYAU
  • [O-][N+](=O)c1cc(cc(c1O)C(CC)C)[N+]([O-])=O
Properties
C10H12N2O5
Molar mass 240.21 g/mol
Density 1.35 g/cm3
Melting point 38-42 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Dinoseb is an herbicide in the dinitrophenol family. The IUPAC name is 2-(butan-2-yl)-4,6-dinitrophenol and its molecular formula is C10H12N2O5. Naturally, dinoseb occurs as orange crystals which cannot dissolve in water easily. Dinoseb is banned as a herbicide in the EU and USA because of its toxicity.

History

In 1892, Dinitro-ortho-cresol (2,4-dinitro-6-methylphenol) was discovered in Germany and first used as an insecticide. It was later also used as a herbicide and also fungicide characteristics were discovered. In 1945 the ortho-methyl group was replaced by a sec-butyl group producing dinoseb. This compound had a superior contact and stomach activity on insects and mites.[1] Dinoseb became commercially available in 1945 and was approved for use in the United States based on safety data from Industrial Bio-Test Laboratories.[2] On January 13, 1984 the Danish ship Dana Optima lost 80 drums of Dinoseb during their trip from North Shields (UK) to Esbjerg (DK). After four months 72 drums were found and recovered.[3] Dinoseb was withdrawn from the market in 1986 due to an increased threat of birth defects after female field workers were exposed to the chemical. It could also cause sterility in men who were exposed to the chemical.[4]

Synthesis

The first step in the synthesis of dinoseb is the synthesis of 2-(1-methylpropyl)phenol from 1-butene and phenol.[5] First, 1-butene is protonated so that a secondary carbocation is formed. This can only happen under acidic conditions. The formed carbocation can undergo electrophilic aromatic substitution with phenol. The product of this reaction is 2-(1-methylpropyl)phenol.

The second step in the synthesis of dinoseb is the nitration of 2-(1-methylpropyl)phenol. First, the nitronium ion is formed from nitric acid and sulfuric acid.[6]

2-(1-methylpropyl)phenol takes up the nitronium ion to form the arenium ion, which has three resonance structures. Water can cleave off the additional proton to form a neutral compound.[6]

The product of this reaction can undergo a second nitration to form dinoseb.

Uses

Dinoseb is a herbicide that was once widely used for weed-control when producing crops like soybeans, vegetables, fruits and nuts, or citrus. In the present, dinoseb is banned in the EU and USA due to its high toxicity. However, dinoseb is still used in China for example; evidenced by the fact that it is found in rain- and drinking water. Nowadays there are other, safer herbicides that can be used.[7] Dinoseb was also used as an insecticide to protect grapes. On the internet, dinoseb and other dinitrophenols are bought as weight-loss pills. It is very dangerous however, and many people have died of accidental overdose.[8]

Toxicity

Dinoseb is highly toxic when ingesting, inhaling or at skin contact. Symptoms include fatigue, sweating, headaches, nausea, stomach aches and fever.[9] It is also an irritant for the eyes. Skin contact causes burns and it turns yellow. For pregnant women this substance is especially dangerous as it can cause growth defects in unborn children.

Dinoseb interferes with the oxidative phosphorylation by acting as an uncoupler, which is the production of ATP in the mitochondria. This is done by making the inner membrane of the mitochondria more permeable to protons. The protons can return to the mitochondrial matrix more easily, which results in a lower difference in proton concentration on either side of the inner mitochondrial membrane. In other words: The proton gradient is lower, so the membrane potential will be lower. As the membrane potential is the driving force for the production of ATP, the cell is unable to produce energy.[10]

Exposure to dinoseb also induces ER-mediated calcium release, resulting in increased intracellular calcium levels. This is followed by activation of caspase, which is a protease involved in cell apoptosis. The surviving cells have an increase of alpha-synuclein levels which leads to dopaminergic neurodegeneration.[7]

Dinoseb can cross biological membranes like the blood-brain barrier and the placental barrier. This explains why dinoseb is particularly dangerous for pregnant women. If the compound can pass the placental barrier, the unborn child will be exposed to dinoseb via the blood of the mother.[7]

Oral LD50 values of Dinoseb range from 14 to 114 mg/kg in rats, mice rabbits and guinea pigs.[8]

See also

References

  1. ^ Topliss, John (2012-12-02). Quantitative Structure-Activity Relationships of Drugs. Elsevier. p. 427. ISBN 9780323146876.{{cite book}}: CS1 maint: date and year (link)
  2. ^ Meyer, Carl (1998-12-29). Expert Witnessing: Explaining and Understanding Science. CRC Press. p. 149. ISBN 9780849311970.{{cite book}}: CS1 maint: date and year (link)
  3. ^ Bockholts, P.; Heidebrink, I. (2012-12-06). 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 Science & Business Media. pp. 325–328. ISBN 9789400908871.{{cite book}}: CS1 maint: date and year (link)
  4. ^ Times, Philip Shabecoff, Special To The New York (1986-10-08). "EMERGENCY ORDER BANS MUCH-USED PESTICIDE". The New York Times. ISSN 0362-4331. Retrieved 2017-03-13.{{cite news}}: CS1 maint: multiple names: authors list (link)
  5. ^ Ashford, R.D. (1994). Ashford's Dictionary of Industrial Chemicals. London, England: Wavelength Publications Ltd. p. 159. ISBN 978-0-9522674-3-0.
  6. ^ a b "Chapter 21:Reactions of Aromatics". research.cm.utexas.edu. Retrieved 2017-03-13.
  7. ^ a b c Heusinkveld, Harm J.; van Vliet, Arie C.; Nijssen, Peter C. G.; Westerink, Remco H. S. (2016-06-11). "In vitro neurotoxic hazard characterisation of dinitrophenolic herbicides". Toxicology Letters. 252: 62–69. doi:10.1016/j.toxlet.2016.04.014. ISSN 1879-3169. PMID 27106277.
  8. ^ a b Zaharia, M.; Tudorachi, L.; Pintilie, O.; Drochioi, C.; Gradinaru, R.; Murariu, M. (2016). "Banned dinitrophenols still trigger both legal and forensic issues". Environmental Forensics. 17(1): 120–130.
  9. ^ "Dinoseb - Toxipedia". www.toxipedia.org. Retrieved 2017-03-13.
  10. ^ Palmeira, C.M.; Moreno, A.J.; Madeira, V.M.C. (1994). "Interactions of Herbicides 2,4-D and Dinoseb with Liver Mitochondrial Bioenergetics". Toxicology and Applied Pharmacology. 127(1): 50–57.
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