Chlormequat

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Chlormequat
Chlormequat structure.svg
Chlormequat.png
Names
Preferred IUPAC name
2-Chloro-N,N,N-trimethylethan-1-aminium
Other names
Chlorocholine; Chlorcholine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C5H13ClN/c1-7(2,3)5-4-6/h4-5H2,1-3H3/q+1
    Key: JUZXDNPBRPUIOR-UHFFFAOYSA-N
  • InChI=1/C5H13ClN/c1-7(2,3)5-4-6/h4-5H2,1-3H3/q+1
    Key: JUZXDNPBRPUIOR-UHFFFAOYAN
  • ClCC[N+](C)(C)C
Properties
C5H13ClN
Molar mass 122.62 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chlormequat is an organic compound with the formula ClCH
2CH
2N(CH
3)+
3 that is used as a plant growth regulator. It is typically sold as the chloride salt, chlormequat chloride[1] (C5H13Cl2N), a colorless hygroscopic crystalline substance that is soluble in water and ethanol.[2] It is an alkylating agent and a quaternary ammonium salt. Chlormequat is one of the onium-type growth regulators.[3]

Chlormequat has been called the "most important inhibitor of gibberellin biosynthesis."[2] As such, it inhibits cell elongation, resulting in thicker stalks, which are sturdier, facilitating harvesting of cereal crops.[4] It can also be used as an adjuvant for herbicides by retarding their oxidative disposal by plants. This is due to cytochrome P450-inhibition.[3]

Regulation and toxicity

In the United States, chlormequat is classified as a low risk plant growth regulator and it is registered for use on ornamental plants grown in greenhouses, nurseries, and shadehouses.[5] It is not approved for use on crops intended for animal or human consumption.[5]

The LD50 (rat, oral) is low, approximately 670 mg/kg.[2]

Exposure to high levels of chlormequat has been linked to developmental toxicity in animal models.[6] It also affects reproduction in mammals.[7]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[8]

References

  1. ^ Chlormequat chloride (ChemSpider)
  2. ^ a b c Wilhelm Rademacher, Lutz Brahm "Plant Growth Regulators" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2010. doi:10.1002/14356007.a20_415.pub2
  3. ^ a b Rademacher, Wilhelm (2000). "Growth Retardants: Effects on Gibberellin Biosynthesis and Other Metabolic Pathways". Annual Review of Plant Physiology and Plant Molecular Biology. Annual Reviews. 51 (1): 501–531. doi:10.1146/annurev.arplant.51.1.501. ISSN 1040-2519. PMID 15012200.
  4. ^ Gowariker, Vasant; Kalyani Paranjape; Sudha Gowariker; V. N. Krishnamurthy (2013). The pesticide encyclopedia. Wallingford: CABI. p. 93. ISBN 978-1780640143.
  5. ^ a b Chlormequat Chloride Reregistration Eligibility Decision for Low Risk Pesticide
  6. ^ "Chlormequat". Food and Agricultural Organization of the United Nations.
  7. ^ Sørensen, MT; Danielsen, V (February 2006). "Effects of the plant growth regulator, chlormequat, on mammalian fertility". International Journal of Andrology. 29 (1): 129–33. doi:10.1111/j.1365-2605.2005.00629.x. PMID 16466532.
  8. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)

External links

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