Chlormequat

Chlormequat
Names
	IUPAC name 2-Chloro-N,N,N-trimethylethanaminium
	Other names Chlorocholine; Chlorcholine
Identifiers
CAS Number	7003-89-6 ; 999-81-5 (chloride salt) ;
3D model (JSmol)	Interactive image;
ChemSpider	13237;
PubChem CID	13837;
UNII	8SUZ1123XX ; PPL2215L82 (chloride salt) ;
CompTox Dashboard (EPA)	DTXSID4048064 ;
	InChI 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;
	SMILES ClCC[N+](C)(C)C;
Properties
Chemical formula	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).
	Infobox references

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 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.[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.[4] It is not approved for use on crops intended for animal or human consumption.[4]

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.[5] It also affects reproduction in mammals.[6]

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.[7]

References

Chlormequat chloride (ChemSpider)
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
Gowariker, Vasant; Kalyani Paranjape; Sudha Gowariker; V. N. Krishnamurthy (2013). The pesticide encyclopedia. Wallingford: CABI. p. 93. ISBN 978-1780640143.
Chlormequat Chloride Reregistration Eligibility Decision for Low Risk Pesticide
"Chlormequat". Food and Agricultural Organization of the United Nations.
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.
"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 requires |journal= (help)

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[1] Chlormequat chloride (ChemSpider)

[Ullmann-2] 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] Gowariker, Vasant; Kalyani Paranjape; Sudha Gowariker; V. N. Krishnamurthy (2013). The pesticide encyclopedia. Wallingford: CABI. p. 93. ISBN 978-1780640143.

[GPO-4] Chlormequat Chloride Reregistration Eligibility Decision for Low Risk Pesticide

[5] "Chlormequat". Food and Agricultural Organization of the United Nations.

[6] 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.

[gov-right-know-7] "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 requires |journal= (help)