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Quinclorac

Quinclorac
Names
Preferred IUPAC name
3,7-Dichloroquinoline-8-carboxylic acid
Other names
Quinchlorac
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.100.457 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H5Cl2NO2/c11-6-3-5-1-2-7(12)8(10(14)15)9(5)13-4-6/h1-4H,(H,14,15)
    Key: FFSSWMQPCJRCRV-UHFFFAOYSA-N
  • InChI=1/C10H5Cl2NO2/c11-6-3-5-1-2-7(12)8(10(14)15)9(5)13-4-6/h1-4H,(H,14,15)
    Key: FFSSWMQPCJRCRV-UHFFFAOYAE
  • O=C(O)c1c(Cl)ccc2cc(Cl)cnc12
Properties
C10H5Cl2NO2
Molar mass 242.06 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Quinclorac is an organic compound with the formula C9NH4Cl2CO2H. A colorless solid, it is soluble in hydrocarbons and alcohols. The compound is the carboxylic acid of 3,7-dichloroquinoline.

Applications

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Quinclorac is an herbicide used primarily to control crabgrass.[1] It is found in some household herbicides for lawn use. Most[citation needed] lawn maintenance companies use the product for the control of annual grass weeds like crabgrass.

Quinclorac is a synthetic auxin.[2][3] Heap considers it to also have a cellulose herbicide action,[4] although some studies show quinclorac to have no cellulose action.[5]

Regulation and registration

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Quinclorac is not approved to use in the European Union due to toxicity concerns.[6][7]

Resistance

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Resistance to quinclorac is of concern in soybean cultivation. In rice, Graminaceous resistance is produced by the cytochrome enzyme CYP81A6.[8]

Further reading

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References

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  1. ^ Müller, Franz; Applebyki, Arnold P. (2011). "Weed Control, 2. Individual Herbicides". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o28_o01. ISBN 9783527303854.
  2. ^ Grossmann, Klaus (1998). "Quinclorac belongs to a new class of highly selective auxin herbicides". Weed Science. 46 (6): 707–716. doi:10.1017/S004317450008975X. S2CID 89297943.
  3. ^ Grossmann, Klaus; Kwiatkowski, Jacek (2000). "The Mechanism of Quinclorac Selectivity in Grasses". Pesticide Biochemistry and Physiology. 66 (2): 83–91. doi:10.1006/pest.1999.2461. ISSN 0048-3575. S2CID 84092985.
  4. ^ Heap, Ian. "List of Herbicide Resistant Weeds by Herbicide Mode of Action (L/26)". International Survey of Herbicide Resistant Weeds. Herbicide Resistance Action Committee. Retrieved 2021-03-14.
  5. ^ Tresch, Stefan; Grossmann, Klaus (2003). "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots". Pesticide Biochemistry and Physiology. 75 (3): 73–78. doi:10.1016/s0048-3575(03)00013-0. ISSN 0048-3575. S2CID 84212641.Tresch, Stefan; Grossmann, Klaus (2003). "Erratum to "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots"". Pesticide Biochemistry and Physiology. 76 (2): 70–71. doi:10.1016/s0048-3575(03)00064-6. ISSN 0048-3575. S2CID 84794877.
  6. ^ "Quinclorac".
  7. ^ "Quinclorac (Ref: BAS 514H)".
  8. ^ Gaines, Todd A.; Duke, Stephen O.; Morran, Sarah; Rigon, Carlos A.G.; Tranel, Patrick J.; Küpper, Anita; Dayan, Franck E. (2020). "Mechanisms of Evolved Herbicide Resistance". Journal of Biological Chemistry. 295 (30). Elsevier BV: 10307–10330. doi:10.1074/jbc.rev120.013572. PMC 7383398. PMID 32430396.
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