Dinitro-ortho-cresol explained

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. It is extremely toxic to humans and was previously used as a herbicide and insecticide.

Preparation

This compound is prepared by disulfonation of o-cresol. The resulting disulfonate is then treated with nitric acid to give DNOC. A variety of related derivatives are known including those where the methyl group is replaced by sec-butyl (dinoseb), tert-butyl (dinoterb), and 1-methylheptyl (dinocap). These are prepared by the direct nitration of the alkyphenols.[1]

Applications and safety

DNOC is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production,[2] [3] making it extremely toxic to humans.[4]

DNOC was one of the earliest pesticides developed, being used as an insecticide since the 1890s and a herbicide since the 1930s.[5] It was banned for use as a pesticide in the United States in 1991.[4]

Symptoms of dinitro-ortho-cresol poisoning, due to ingestion or other forms of exposure, include confusion, fever, headache, shortness of breath, and sweating.[6]

External links

Notes and References

  1. Encyclopedia: Gerald Booth. Nitro Compounds, Aromatic. Ullmann's Encyclopedia of Industrial Chemistry. 2007. Wiley-VCH. Weinheim. 10.1002/14356007.a17_411.
  2. Parker . V. H. . Barnes . J. M. . Denz . F. A. . Some Observations on the Toxic Properties of 3:5-Dinitro-Ortho-Cresol . 10.1136/oem.8.4.226 . 1951 . 226 . 8 . Occupational and Environmental Medicine . 4. 1037342 . 14878957.
  3. 14839311 . Harvey . DG . 1951 . 13–6 . 4722 . Bidstrup . 2 . PL . British Medical Journal . Bonnell . JA . Poisoning by dinitro-ortho-cresol; some observations on the effects of dinitro-ortho-cresol administered by mouth to human volunteers . 2069381 . 10.1136/bmj.2.4722.13.
  4. Web site: 4,6-DINITRO-o-CRESOL (DNOC) (including salts) . Environmental Protection Agency . 14 December 2023.
  5. Biegaǹska . Jolanta . Neutralization of 4,6-Dinitro- o -cresol Waste Pesticide by Means of Detonative Combustion . Environmental Science & Technology . 1 February 2005 . 39 . 4 . 1190–1196 . 10.1021/es035327p.
  6. Web site: Chemical poisoning -- Dinitrocresol Symptoms, Diagnosis, Treatments and Causes - RightDiagnosis.com. www.rightdiagnosis.com.

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