:Quinclorac
{{short description|Chemical compound}}
{{Chembox
| ImageFile = Quinclorac.svg
| ImageSize = 200px
| PIN = 3,7-Dichloroquinoline-8-carboxylic acid
| OtherNames = Quinchlorac
|Section1={{Chembox Identifiers
| CASNo = 84087-01-4
| CASNo_Ref = {{cascite|correct|}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3J06V625EE
| PubChem = 91739
| ChemSpiderID = 82837
| ChEBI = 81974
| KEGG = C18806
| SMILES = O=C(O)c1c(Cl)ccc2cc(Cl)cnc12
| 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)
| InChIKey = FFSSWMQPCJRCRV-UHFFFAOYAE
| StdInChI = 1S/C10H5Cl2NO2/c11-6-3-5-1-2-7(12)8(10(14)15)9(5)13-4-6/h1-4H,(H,14,15)
| StdInChIKey = FFSSWMQPCJRCRV-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=10 | H=5 | Cl=2 | N=1 | O=2
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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}}
Quinclorac is an organic compound with the formula {{chem2|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.{{cite book | doi = 10.1002/14356007.o28_o01 | chapter = Weed Control, 2. Individual Herbicides | title = Ullmann's Encyclopedia of Industrial Chemistry | date = 2011 | last1 = Müller | first1 = Franz | last2 = Applebyki | first2 = Arnold P. | isbn = 9783527303854 }} It is found in some household herbicides for lawn use. Most{{citation-needed|date=July 2023}} lawn maintenance companies use the product for the control of annual grass weeds like crabgrass.
Quinclorac is a synthetic auxin.{{cite journal | last = Grossmann | first = Klaus | year = 1998 | title = Quinclorac belongs to a new class of highly selective auxin herbicides | journal = Weed Science| volume = 46 | issue = 6 | pages = 707–716| doi = 10.1017/S004317450008975X | s2cid = 89297943 }}{{cite journal | last1=Grossmann | first1=Klaus | last2=Kwiatkowski | first2=Jacek | title=The Mechanism of Quinclorac Selectivity in Grasses | journal=Pesticide Biochemistry and Physiology | volume=66 | issue=2 | year=2000 | issn=0048-3575 | doi=10.1006/pest.1999.2461 | pages=83–91 | s2cid=84092985}}
Heap considers it to also have a cellulose herbicide action,{{cite web |first=Ian|title=List of Herbicide Resistant Weeds by Herbicide Mode of Action (L/26)|last=Heap|url=http://www.weedscience.org/summary/MOA.aspx?MOAID=19 | website=International Survey of Herbicide Resistant Weeds | publisher=Herbicide Resistance Action Committee | language=en | access-date=2021-03-14}} although some studies show quinclorac to have no cellulose action.{{cite journal | last1=Tresch | first1=Stefan | last2=Grossmann | first2=Klaus | title=Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots | journal=Pesticide Biochemistry and Physiology| volume=75 | issue=3 | year=2003 | issn=0048-3575 | doi=10.1016/s0048-3575(03)00013-0 | pages=73–78 | s2cid=84212641}}{{cite journal | last1=Tresch | first1=Stefan | last2=Grossmann | first2=Klaus | title=Erratum to "Quinclorac does not inhibit cellulose (cell wall) biosynthesis in sensitive barnyard grass and maize roots" | journal=Pesticide Biochemistry and Physiology | volume=76 | issue=2 | year=2003 | issn=0048-3575 | doi=10.1016/s0048-3575(03)00064-6 | pages=70–71 | s2cid=84794877| doi-access=free }}
Regulation and registration
Quinclorac is not approved to use in the European Union due to toxicity concerns.{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Quinclorac | title=Quinclorac }}{{cite web | url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/577.htm | title=Quinclorac (Ref: BAS 514H) }}
Resistance
Resistance to quinclorac is of concern in soybean cultivation. In rice, Graminaceous resistance is produced by the cytochrome enzyme CYP81A6.{{Cite journal|publisher=Elsevier BV|journal=Journal of Biological Chemistry|doi=10.1074/jbc.rev120.013572|title=Mechanisms of Evolved Herbicide Resistance |year=2020 |doi-access=free |last1=Gaines |first1=Todd A. |last2=Duke |first2=Stephen O. |last3=Morran |first3=Sarah |last4=Rigon |first4=Carlos A.G. |last5=Tranel |first5=Patrick J. |last6=Küpper |first6=Anita |last7=Dayan |first7=Franck E. |volume=295 |issue=30 |pages=10307–10330 |pmid=32430396 |pmc=7383398 }}
Further reading
- {{Cite journal|department=Mini Review|doi=10.4161/psb.6.8.15793|title=The use of FTIR spectroscopy to monitor modifications in plant cell wall architecture caused by cellulose biosynthesis inhibitors|year=2011 |last1=Alonso-Simón |first1=Ana |last2=García-Angulo |first2=Penélope |last3=Mélida |first3=Hugo |last4=Encina |first4=Antonio |last5=Álvarez |first5=Jesús M. |last6=Acebes |first6=José L. |journal=Plant Signaling & Behavior |volume=6 |issue=8 |pages=1104–1110 |pmid=21791979 |pmc=3260703 |bibcode=2011PlSiB...6.1104A }}
References
External links
- {{PPDB|577}}
{{herbicides}}