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Quinclorac

Names
Preferred IUPAC name 3,7-Dichloroquinoline-8-carboxylic acid
Other names Quinchlorac
Identifiers
CAS Number	84087-01-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81974
ChemSpider	82837
ECHA InfoCard	100.100.457
KEGG	C18806
PubChem CID	91739
UNII	3J06V625EE
CompTox Dashboard (EPA)	DTXSID6032641
InChI 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
SMILES O=C(O)c1c(Cl)ccc2cc(Cl)cnc12
Properties
Chemical formula	C10H5Cl2NO2
Molar mass	242.06 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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

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

Quinclorac is a synthetic auxin. Heap considers it to also have a cellulose herbicide action, although some studies show quinclorac to have no cellulose action.

Regulation and registration

Quinclorac is not approved to use in the European Union due to toxicity concerns.

Resistance

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

Further reading

• Alonso-Simón, Ana; García-Angulo, Penélope; Mélida, Hugo; Encina, Antonio; Álvarez, Jesús M.; Acebes, José L. (2011). "The use of FTIR spectroscopy to monitor modifications in plant cell wall architecture caused by cellulose biosynthesis inhibitors". Mini Review. Plant Signaling & Behavior. 6 (8): 1104–1110. Bibcode:2011PlSiB...6.1104A. doi:10.4161/psb.6.8.15793. PMC 3260703. PMID 21791979.

References

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.

External links

• Quinclorac in the Pesticide Properties DataBase (PPDB)

• Auxinic herbicides
• Quinolines
• Chloroarenes
• Carboxylic acids