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| | QUINMERAC Basic information |
| | QUINMERAC Chemical Properties |
| Melting point | 244°C | | Boiling point | 416.0±40.0 °C(Predicted) | | density | 1.406±0.06 g/cm3(Predicted) | | storage temp. | Room Temperature, under inert atmosphere | | solubility | DMSO (Slightly), Methanol (Slightly, Sonicated) | | pka | -2.84±0.10(Predicted) | | color | Pale Yellow to Pale Beige | | Merck | 13,8158 | | BRN | 8392904 | | Henry's Law Constant | 1.0×1010 mol/(m3Pa) at 25℃, Maniere et al. (2011) | | Major Application | agriculture
environmental | | InChI | InChI=1S/C11H8ClNO2/c1-6-4-7-2-3-8(12)9(11(14)15)10(7)13-5-6/h2-5H,1H3,(H,14,15) | | InChIKey | ALZOLUNSQWINIR-UHFFFAOYSA-N | | SMILES | N1C2C(=CC=C(Cl)C=2C(O)=O)C=C(C)C=1 | | LogP | 0.780 | | EPA Substance Registry System | Quinmerac (90717-03-6) |
| Hazard Codes | T | | WGK Germany | 2 | | RTECS | VB1981800 | | HS Code | 29333990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 4 | | Toxicity | LD50 in rats (mg/kg): >5000 orally, >2000 dermally (Wuerzer) |
| | QUINMERAC Usage And Synthesis |
| Chemical Properties | Crystalline Solid | | Uses | Auxin-type herbicide. | | Uses | Herbicide. | | Definition | ChEBI: A quinolinemonocarboxylic acid that is quinoline-8-carboxylic acid carrying additional methyl and chloro substituents at positions 3 and 7 respectively. A residual herbicide used to control broad-leaved weeds on a range of crops including cereals, rape and
beet. | | Production Methods | Quinmerac is commercially produced through a multi-step synthesis starting with the Skraup reaction of 3-amino-4-chlorobenzoic acid with glycerol and sulfuric acid to form 8-chloroquinoline-3-carboxylic acid, followed by selective nucleophilic substitution of the 8-chloro group with methanethiol under basic conditions to yield 8-(methylthio)quinoline-3-carboxylic acid, which is then oxidised with hydrogen peroxide or peracid to the corresponding methylsulfonyl derivative, quinmerac. | | Mechanism of action | Selective. Absorbed by roots, synthetic auxin | | Environmental Fate | In the field, the DT50 of quinmerac
may range from 3 to 33 days. Losses due to volatilization
are negligible. Soil moisture conditions greatly influence
quinmerac persistence by moderating microbial degradation
and soil leaching. Quinmerac is only slightly adsorbed
to the soil. | | Metabolism | Chemical. Quinmerac is stable to heat, light, and in
aqueous solutions with pH values between 3 and 9.
Plant. The degradation and metabolic pathways of
quinmerac have not been extensively studied. In plants,
oxidation of the 3-methyl group to the alcohol and
hydroxylation at the 2-quinoline position are the major
metabolism reactions (56). These quinmerac metabolites
are subsequently conjugated to carbohydrates. The
quantity of quinmerac metabolized varies among species,
ranging from 5% to 80% (56).
Soil. In the soil, degradation of quinmerac was similar
to that observed in plants, resulting in the same
oxygenated and hydroxylated metabolites. | | Toxicity evaluation | Quinmerac is excreted in the urine
of mammals and appears to remain primarily unmodified.
The acute oral LD50 in rat is >5000 mg/kg. | | Pesticide Type | Herbicide |
| | QUINMERAC Preparation Products And Raw materials |
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