Quinclorac
- Iupac Name：3,7-dichloroquinoline-8-carboxylic acid
- CAS No.: 84087-01-4
- Molecular Weight：242.05800
- Modify Date.: 2022-11-25 02:20
- Introduction: Quinclorac 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.
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1. Names and Identifiers
- 1.1 Name
- Quinclorac
- 1.2 Synonyms
3,7-dichloro-8-quinoline carboxylic acid 3,7-Dichloro-8-quinolinecarboxylic acid 3,7-dichloro-quinoline-8-carboxylic acid 3,7-dichloroquinoline-8-carboxylic acid 8-Quinolinecarboxylic acid, 3,7-dichloro- BAS 514 BAS-514-H dichloroquinolinicacid Drive EINECS 402-780-1 FACET facet 75 df Facet LA FACET(R) FAS-NOX MFCD00072495 Parmount QUEEN QUINCHLORAC T66 BNJ DG IG JVQ
- 1.3 CAS No.
- 84087-01-4
- 1.4 CID
- 91739
- 1.5 EINECS(EC#)
- 617-530-9; 402-780-1
- 1.6 Molecular Formula
- C10H5Cl2NO2 (isomer)
- 1.7 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)
- 1.8 InChkey
- FFSSWMQPCJRCRV-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC(=C(C2=NC=C(C=C21)Cl)C(=O)O)Cl
- 1.10 Isomers Smiles
- C1=CC(=C(C2=NC=C(C=C21)Cl)C(=O)O)Cl
2. Properties
- 2.1 Density
- 1.506g/cm3
- 2.1 Melting point
- 274ºC
- 2.1 Boiling point
- 407.4ºC at 760 mmHg
- 2.1 Refractive index
- 1.685
- 2.1 Flash Point
- 100°C
- 2.1 Precise Quality
- 240.97000
- 2.1 PSA
- 50.19000
- 2.1 logP
- 3.23980
- 2.1 Solubility
- (mg/m1)
- 2.2 Appearance
- Colourtess crystals.
- 2.3 Color/Form
- White/yellow solid|Colorless crystalline solid
- 2.4 Odor
- Odorless
- 2.5 pKa
- -3.26±0.10(Predicted)
- 2.6 Water Solubility
- In water, 0.065 mg/kg (pH 7, 20 °C)
- 2.7 Stability
- Stable under recommended storage conditions.
- 2.8 StorageTemp
- Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A quinolinemonocarboxylic acid that is quinoline-8-carboxylic acid in which the hydrogens at positions 3 and 7 have been replaced by chlorines.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.
- 3.2 Usage
- Quinclorac 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.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xi
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R43
- 4.1 Safety Statements
- S2; S24; S37
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 3.2
- 4.1 Hazard Declaration
- H317
- 4.1 RIDADR
- 1993
- 4.1 Caution Statement
- P280
- 4.1 WGK Germany
- 2
- 4.1 RTECS
- VB1984000
- 4.1 Safety
-
Safty information about Quinclorac (CAS NO.84087-01-4) is:
Moderately toxic by ingestion and skin contact routes. Low toxicity by inhalation route. When heated to decomposition it emits toxic vapors of NOx and Cl?.
Hazard Codes:?
Xi
Risk Statements: 43?
R43:May cause sensitization by skin contact.
Safety Statements: 2-24-37?
S2:Keep out of the reach of children.?
S24:Avoid contact with skin.?
S37:Wear suitable gloves.
RTECS: VB1984000
- 4.2 Specification
-
?Quinclorac , its cas register number is 84087-01-4. It also can be called 3,7-Dichloro-8-quinolinecarboxylic acid ; Quinclorac [ISO] ; 3,7-Dichloroquinoline-8-carboxylic acid ; BAS 514 00H ; EPA Pesticide Chemical Code 128974 ; Facet ; Quinclorac tech ; 8-Quinolinecarboxylic acid, 3,7-dichloro- .It is a?synthetic auxin.
- 4.3 Toxicity
- Organic Compound; Organochloride; Pesticide; Ester; Herbicide; Household Toxin; Synthetic Compound
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin sensitization, Category 1
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H317 May cause an allergic skin reaction |
| Precautionary statement(s) | |
| Prevention | P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
84087-01-4Total: 1 Synthesis Route
8. Other Information
- 8.0 Henrys Law Constant
- Henry's Law constant = 7.61X10-12 atm-cu m/mol at 25 °C (est)
- 8.1 Dissociation Constants
- pKa = 4.34
- 8.2 Collision Cross Section
- 139.54 ?2 [M+H]+ [CCS Type: TW]
- 8.3 Disposal Methods
- SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
- 8.4 Personal Protective Equipment
- Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
- 8.5 Fire Fighting Procedures
- Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
- 8.6 Cleanup Methods
- ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
- 8.7 Preventive Measures
- ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
- 8.8 Pollution Sources
- Quinclorac's production may result in its release to the environment through various waste streams; its use as a herbicide to control weeds on agricultural crops, and turf in residential and commercial areas(1) will result in its direct release to the environment(SRC).
- 8.9 Environmental Fate
- TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that quinclorac is expected to have moderate mobility in soil(SRC). The pKa of quinclorac is 4.34(3), indicating that this compound will exist partialy in the anion form in the environment and anions generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the neutral species from moist soil surfaces is not expected(4) based upon an estimated Henry's Law constant of 7.6X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Quinclorac is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Quinclorac is stable to hydrolysis in sterile water however the compound undergoes rapid photolysis in non-sterile rice paddy, natural river waters and solutions containing activated sludge with half-lives of 5-10 days reported(5). Quincloarac is resistent to biodegradation in soil under aerobic and anaerobic conditions(5), indicating that biodegradation is not an important environmental fate process in soil(SRC).|FIELD STUDY: Quinclorac applied to experimental rice fields in Tianjin and Jilin Provinces, China in 1993 and 1994, exhibited rapid dissipation from water, with half-lives of 0.8 and 2 days, respectively. The half-life from rice leaves was <1 day; sediment half-life was reported as 6 days. The compound was not detected in associated soils. Levels in rice at pre-harvest interval of 95-105 days was <0.005 mg/kg(1). A field half-life range of 18-176 days has also been reported(2).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 470(SRC), determined from a structure estimation method(2), indicates that quinclorac is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.34(3) indicates quinclorac will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). Volatilization of the neutral species from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 7.6X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Quinclorac was reported to be stable under both UV light and sunlight under aqueous conditions(4) the compound undergoes rapid photolysis in non-sterile rice paddy, natural river waters and solutions containing activated sludge with half-lives of 5-10 days reported. According to a classification scheme(5), a BCF of <1(6) suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation of <10% was reported in 28 days in an aquatic ready biodegradability test(7), indicating that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), quinclorac, which has an estimated vapor pressure of 4.0X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase quinclorac is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase quinclorac may be removed from the air by wet and dry deposition(SRC). Quinclorac contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
- 8.10 Abiotic Degradation
- The rate constant for the vapor-phase reaction of quinclorac with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Quinclorac contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC) The compound is reported to be stable to hydrolysis and photolysis in sterile water(3). Quinclorac was reported to be stable under both UV light and sunlight under aqueous conditions(4). However, the compound undergoes rapid photolysis in non-sterile rice paddy, natural river waters and solutions containing activated sludge with half-lives of 5-10 days reported(3). A half-life of 141 days was reported for photolysis on soil surfaces(3).
- 8.11 Bioconcentration
- A log BCF of -0.38722 (BCF <1) was reported in fish for quinclorac(SRC), using bluegill (Lepomis macrochirus) which were exposed over a 4-week period in the OPPTS 850.1730 test(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
- 8.12 Mobility
- Using a structure estimation method based on molecular connectivity indices(1), the Koc of quinclorac can be estimated to be 470(SRC). According to a classification scheme(2), this estimated Koc value suggests that quinclorac is expected to have moderate mobility in soil. The pKa of quinclorac is 4.34(3), indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).|A sorption coefficient Kd of <1 indicates that leaching is a probable route of dissipation in the soil environment. Some leaching was observed, as quinclorac was detected below the 12 inch soil depth in the several of the terrestrial field dissipation studies. Detections of residues of quinclorac and its degradates in the soil down to 42-48 inches were reported in terrestrial field studies performed in KS, CA, MO, and NJ(1). Soil column leaching experiments were conducted using 3 of 5 major soil zones found in Alberta, Canada, and 10 g of quinclorac-spiked soils, equivalent to 120 g/ha. Quinclorac was reported to leach very rapidly (84 to 97% by 0.67 rain year) in brown Skiff loam (pH 6.0; 2.1% OM) and dark brown Lethridge loam (pH 7.6; 2.7% OM). Intermediate leaching (69-76% by 3.0 rain-year) was reported using black Lacombe sandy loam (pH 5.6; 5.9% OM)(2).
- 8.13 Volatilization
- A pKa of 4.34(1) indicates quinclorac will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). The Henry's Law constant for the neutral species of quinclorac is estimated as 7.6X10-12 atm-cu m/mole(SRC) developed using a fragment constant estimation method(2). This Henry's Law constant indicates that quinclorac is expected to be essentially nonvolatile from water and moist soil surfaces(2). Quinclorac is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.0X10-8 mm Hg(SRC), determined from a fragment constant method(2).
- 8.14 Human Exposure
- Occupational exposure to quinclorac may occur through inhalation of dust and dermal contact with this compound at workplaces where quinclorac is produced or used. Use data indicate that the general population may be exposed to quinclorac via dermal contact with consumer products containing quinclorac. (SRC)
- 8.15 Mesh
- Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)
- 8.16 Absorption
- The extent of oral absorption was high (> 90%), based on urinary and biliary data, with most of the biliary component reabsorbed and excreted in urine. The biliary component increased disproportionately with increasing dose from 15 to 600 mg/kg bw. Absorption of radiolabel was rapid, with maximal blood concentrations achieved between 0.25 and 1 hour for single doses of 600 mg/kg bw and below. Quinclorac was widely distributed in the body, with highest concentrations present in the blood, plasma and kidneys. Tissue levels were generally higher (< 2-fold) in females than in males. The labelled material was rapidly excreted, primarily via urine (50-90% in 24 hours). Initial plasma half-lives were calculated to be approximately 3-4 hours. Clearance from the blood was slower following repeated dosing with 600 mg/kg bw and with single doses of 1200 mg/kg bw, resulting in non-proportionate increases in the area under the concentration-time curve (AUC). The excretion pattern and tissue distribution of radioactivity were similar across administered dose levels and when the administration of radiolabelled quinclorac was preceded by 7 or 14 days of administration of the labelled or unlabelled material.|The metabolism of quinclorac ((2,3,4-(14)C)3,7-dichloro-8-quinolinecarboxylic acid) following oral administration was studied extensively in male and female CD rat. The compound was rapidly absorbed and eliminated in the urine following administration of single oral doses of (14)C quinclorac at 15 or 600 mg/kg and at 15 mg/kg after the animals were dosed with unlabeled quinclorac at 15 mg/kg/day for 14 days. Elimination in the urine 5 days after dosing accounted for 91 to 98% of the dose with only 1 to 4% eliminated in the feces. No radioactivity was detected in expired air. Biliary excretion was significant (11.5 to 14.5% of the dose) in animals receiving 600 mg/kg. However, most of this radioactivity was reabsorbed from the intestines and eliminated in the urine. Most of the radioactivity in the bile is associated with the glucuronide conjugate of quinclorac. The conjugate is apparently hydrolyzed in the intestines and reabsorbed. Almost all the radioactivity in the urine is unchanged quinclorac. Radioactive tissue residue levels 5 days after dosing were dose-dependent. Results from these and other (whole-body autoradiography and time-course) studies indicate that quinclorac may accumulate in the adrenal glands, bone marrow, thyroid, squamous epithelium of the non-fundic stomach, and ovaries.|In 7-day time-course studies (oral gavage at 15 mg/kg/day or dietary at about 1,000 mg/kg/day) maximum (14)C residue levels were detected 30 minutes after the final dose; thereafter, residue levels decreased with time. Mean (14)C residues in plasma were also detected at 30 minutes in animals receiving single oral doses of 15, 100, or 600 mg/kg or 15 mg/kg/day for 7 days. Elimination was biphasic with half-lives of 3 to 4 hours for the rapid phase at the low doses and a half-life of about 13 hours at 600 mg/kg. Peak plasma levels of radioactivity in animals receiving higher doses (1200 mg/kg or 600 mg/kg/day for 7 days) were noted for 7 to 48 hours postdosing: saturation kinetics were also noted at these higher doses.
- 8.17 Metabolism
- Samples ... extracted and analyzed for the presence of metabolites using techniques including thin-layer chromatography and mass spectroscopy. Absorbed quinclorac was metabolized to only a limited extent, with unchanged parent compound representing approximately 80% of the excreted radiolabel. The major biotransformation product was quinclorac-glucuronide conjugate, representing approximately 5% of the administered dose. The pattern of metabolism was similar across sexes, dose levels and administration of repeated doses. A number of metabolites each representing less than 5% of the administered dose were not identified. The metabolism of quinclorac is so limited that a metabolic pathway is considered unnecessary.
- 8.18 Biological Half Life
- In 7-day time-course studies (oral gavage at 15 mg/kg/day or dietary at about 1,000 mg/kg/day) maximum (14)C residue levels were detected 30 minutes after the final dose; thereafter, residue levels decreased with time. ... Elimination was biphasic with half-lives of 3 to 4 hours for the rapid phase at the low doses and a half-life of about 13 hours at 600 mg/kg. ...
- 8.19 Antidote
- /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
- 8.20 Human Toxicity Excerpts
- /GENOTOXICITY/ Human lymphocytes (whole blood) were treated with Reg. No. 150 732 (Quinclorac) (technical grade) (purity: 96.5%) at concentrations ranging from 125 to 1500 ug/mL (non activation) or 250 to 2500 ug/mL (activation) at 37 °C for 24 hours (non activation) or 2 hours, followed by an additional 22 hours of incubation (activation), following 48 hours in culture with phytohemaglutinin. The cells were cultured in the presence of Colcemid (1.33 ug/mL) the last 2 to 3 hours of the incubation period. There were duplicate cultures for each treatment level. An Aroclor 1254-derived rat liver S9 fraction was used to metabolize the test material. A treatment-related increase in the incidence of chromosomal aberrations was noted for the non-activated cultures (p<0.01). The highest treatment level examined in the activated samples demonstrated an increase in the incidence of aberrant chromosomes with gaps (p<0.05). However, there was a treatment-related reduction in the mitotic index indicative of increasing cytotoxicity. The chromosomal aberrations may have been a secondary consequence of the cytotoxicity. Possible adverse effect indicated: increased incidence of chromosomal aberrations.|/GENOTOXICITY/ Human lymphocytes were treated with Reg. No. 150 732 (Quinclorac) (technical grade) (purity: 96.5%) or Reg. No. 150 732 (batch no. CH 384 121) (purity: >98%) at a concentration of 1000 ug/mL under conditions of non activation at 37 °C for 24 hours following 48 hours of stimulation with phytohemagglutinin (PHA). The cells were cultured in the presence of Colcemid (1.33 ug/mL) the last 2 to 3 hours of the incubation period. There were duplicate cultures for each treatment level. A treatment-related increase in the incidence ofchromosomal aberrations was noted for both test materials (p<0.01). Possible adverse effect indicated: increased incidence of chromosomal aberrations.|/GENOTOXICITY/ In vitro mammalian chromosome aberration assay, human lymphocytes: Positive for chromosomal aberrations but only at cytotoxic concentrations (2000 ug/mL with S9 and 1000 ug/mL without S9). /From table/|/GENOTOXICITY/ Test: Chromosomal aberrations; Target: Human lymphocytes; Concentration or dose tested: 250, 500 and 1,000 ug/mL (+/-S9); Purity (%): 96.5; Results: Positive +/-S9. /From table/
- 8.21 Mesh Entry Terms
- 3,7-dichloro-8-quinolinecarboxylic acid
- 8.22 Formulations
- The National Pesticide Information Retrieval System (NPIRS) identifies 24 companies with active labels for products containing the chemical quinclorac. To view the complete list of companies, product names and percent quinclorac in formulated products click the following url and enter the CAS Registry number in the Active Ingredient field.|Quinclorac Technical (Adama Celsius Property B.V.): Active ingredient: quinclorac 98.0%.|Advan P=Q (Advan, LLC): Active ingredient: prodiamine 32.5% and quinclorac 32.5%.|Quinclorac 4L Turf (Albaugh, LLC): Active ingredient: quinclorac 40.0%.|For more Formulations/Preparations (Complete) data for Quinclorac (29 total), please visit the HSDB record page.
- 8.23 Manufacturing Info
- Registration Notes: Outside USA: Accord: Canada. Fas-Nox, Silis in Argentina.
- 8.24 Use Classification
- Agrochemicals -> Herbicides
- 8.25 BRN
- 7761858
- 8.26 Uses
- Quinclorac 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.
- 8.27 Definition
- ChEBI: 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.
- 8.28 Pharmacology
- The 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).
- 8.29 Metabolism
- Quinclorac 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.
- 8.30 Toxicity evaluation
- Quinclorac 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).
9. Computational chemical data
- Molecular Weight: 242.05800g/mol
- Molecular Formula: C10H5Cl2NO2
- Compound Is Canonicalized: True
- XLogP3-AA: 3
- Exact Mass: 240.9697338
- Monoisotopic Mass: 240.9697338
- Complexity: 262
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 50.2
- Heavy Atom Count: 15
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYByMAAGAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAACx8AAAHgIACAAADArBniQ8yPIIEgCoAzT3TACCgCA1BSAI2CEoTtgIJvrBl5HEcYhmwAHI3UeYyOCOBAACAAIDAAAIAAQABAYAAAAAAAAAAA==
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11. Realated Product Infomation
skype
3YRS
