Quinclorac

Quinclorac Basic information
Product Name:Quinclorac
Synonyms:dichloroquinolinicacid;facet 75 df;FACET(R);FAS-NOX;BAS-514-H;QUEEN;QUINCHLORAC;QUINCLORAC
CAS:84087-01-4
MF:C10H5Cl2NO2
MW:242.06
EINECS:402-780-1
Product Categories:HERBICIDE
Mol File:84087-01-4.mol
Quinclorac Structure
Quinclorac Chemical Properties
Melting point 274°C
Boiling point 405.4±40.0 °C(Predicted)
density 1.7500
refractive index 1.6100 (estimate)
Fp 100 °C
storage temp. Sealed in dry,Room Temperature
solubility DMSO (Slightly), Methanol (Slightly)
pka-3.26±0.10(Predicted)
form neat
color Pale Yellow
BRN 7761858
InChIKeyFFSSWMQPCJRCRV-UHFFFAOYSA-N
EPA Substance Registry SystemQuinclorac (84087-01-4)
Safety Information
Hazard Codes Xi
Risk Statements 43
Safety Statements 2-24-37
WGK Germany 2
RTECS VB1984000
HS Code 29334900
Hazardous Substances Data84087-01-4(Hazardous Substances Data)
MSDS Information
ProviderLanguage
3,7-Dichloro-8-quinolinecarboxylic acid English
Quinclorac Usage And Synthesis
UsesQuinclorac is a disubstituted quinolinecarboxylic acid that is part of a new class of highly selective auxin herbicides. Quinclorac is used in rice to control dicotyledonous and monocotyledonous weeds , particularly barnyardgrass (Echinochloa crus-galli). Quinclorac is also used for weed control in turfgrasses.
UsesQuinclorac is a disubstituted quinolinecarboxylic acid that is part of a new class of highly selective auxin herbicides. Quinclorac is used in rice to control dicotyledonous and monocotyledonous weeds, particularly barnyardgrass (Echinochloa crus-galli). Quinclorac is also used for weed control in turfgrasses.
DefinitionChEBI: A quinolinemonocarboxylic acid that is quinoline-8-carboxylic acid in which the hydrogens at positions 3 and 7 have been replaced by chlorines. It is used (particularly as its dimethylamine salt, known as quinclorac-dimethylammonium) as a (rather persisten ) herbicide for the post-emergence control of weeds in rice, grass and turf. It is not approved for use within the European Union.
PharmacologyThe mechanism of action of quinclorac is controversial. Koo et al. (27) reported that quinclorac inhibited the incorporation of glucose into the cell wall of maize root cells. The synthesis of cellulose as well as some hemicellulose was inhibited at concentrations that inhibited whole plant growth, leading to the conclusion that quinclorac inhibits cell expansion by inhibiting glucose incorporation into the cell wall (27). These authors found that quinclorac inhibited root elongation in sensitive grasses at concentrations that inhibited cell wall biosynthesis. Cell wall biosynthesis in tolerant grasses was much less affected by quinclorac compared with sensitive grasses (28). Grossmann, on the other hand, believes that quinclorac acts as an auxinic herbicide in grasses as well as broadleaf plants, and that its herbicidal effects are due to production of cyanide (which is a byproduct of ethylene biosynthesis) and induction of the plant hormone abscisic acid (29). In this scenario, inhibition of cell wall biosynthesis would be considered a side effect, and not the primary cause of herbicidal injury. Differences in tolerance to quinclorac in this case are solely due to differences in ethylene induction, in that tolerant plants do not respond to quinclorac by synthesizing ethylene (29,30).
MetabolismQuinclorac has been under development by BASF since 1982, and it has been marketed since 1984, as the herbicide Facet. Synthesis data are not currently available. Absorption and uptake of quinclorac is rapid, with 85% uptake in crabgrass within the first 30 minutes. Although uptake of quinclorac is rapid, translocation is generally poor, especially in sensitive plants. Tolerant species, such as Kentucky bluegrass, tend to transport more of the chemical away from the area of uptake. This may, in part, explain how tolerant plants are less affected by quinclorac. Quinclorac is metabolized very slowly in both sensitive and tolerant grass species. In leafy spurge, themajor metabolite found 7 days after foliar application of quinclorac was a pentosylglucose ester.
In susceptible grasses, early symptoms of quinclorac activity include rapid chlorosis starting at the elongation zone of newly expanding leaves. This is followed by more widespread chlorosis and, eventually, necrosis. On the other hand, quinclorac seems to affect susceptible broadleaf plants as an auxinic herbicide. Symptoms in broadleaf plants begin with induction of ethylene biosynthesis and epinastic bending of shoots and leaves. This is followed by growth inhibition, chlorosis, wilting, and, finally, necrosis.
Toxicity evaluationQuinclorac is nonflammable and noncorrosive, and it is stable in storage for at least 2 years. Quinclorac is classified as general use, with an oral LD50 > 2.61 g/kg in rats (31).
Quinclorac Preparation Products And Raw materials
Isoquinoline Ethyl 2-(Chlorosulfonyl)acetate Quinclorac 7-CHLOROQUINOLINE 8-Quinolinecarbaldehyde Folic acid Ethoxyquin 2-Chloroquinoline 2,3-Dichloroquinoxaline QUINCLORAC-METHYL ESTER 4,7-Dichloroquinoline Permethric acid chloroquinoline Clopyralid Quinolinic acid CARBOXYLIC ACID 8-Hydroxyquinoline 2,4-Dichloroquinazoline

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