Propachlor (CHEM000932)

Record Information
Version1.0
Creation Date2009-06-18 21:54:34 UTC
Update Date2026-08-18 10:04:19 UTC
Accession NumberCHEM000932
Identification
Common NamePropachlor
ClassSmall Molecule
Description
Propachlor is widely used as a selective herbicide worldwide in corn, soybean and other crop cultures. Elevated concentrations of these herbicides and their degradation products have been detected in surface and groundwater. Propachlor is a pre-emergence herbicide, effective against annual grasses and certain broad-leaved weeds. It is a compound of the family of chloroacetanilides. (1, 3)
Contaminant Sources
  • Clean Air Act Chemicals
  • EPA Endocrine Screening
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Aromatic Hydrocarbon
  • Chloroacetanilide
  • Food Toxin
  • Household Toxin
  • Lachrymator
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Chloro-N-(1-methylethyl)-N-phenylacetamideChEBI
2-Chloro-N-isopropylacetanilideChEBI
alpha-Chloro-N-isopropylacetanilidChEBI
alpha-Chloro-N-isopropylacetanilideChEBI
Bexton 4lChEBI
Chloressigsaeure-N-isopropylanilidChEBI
Kartex aChEBI
N-Isopropyl-2-chloroacetanilideChEBI
N-Isopropyl-alpha-chloroacetanilideChEBI
NitacidChEBI
NiticidChEBI
PropachloreChEBI
Ramrod 65ChEBI
a-Chloro-N-isopropylacetanilidGenerator
Α-chloro-N-isopropylacetanilidGenerator
a-Chloro-N-isopropylacetanilideGenerator
Α-chloro-N-isopropylacetanilideGenerator
N-Isopropyl-a-chloroacetanilideGenerator
N-Isopropyl-α-chloroacetanilideGenerator
RamrodMeSH
Chemical FormulaC11H14ClNO
Average Molecular Mass211.688 g/mol
Monoisotopic Mass211.076 g/mol
CAS Registry Number1918-16-7
IUPAC Name2-chloro-N-phenyl-N-(propan-2-yl)acetamide
Traditional Namepropachlor
SMILESCC(C)N(C(=O)CCl)C1=CC=CC=C1
InChI IdentifierInChI=1S/C11H14ClNO/c1-9(2)13(11(14)8-12)10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3
InChI KeyMFOUDYKPLGXPGO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Tertiary carboxylic acid amide
  • Chloroacetamide
  • Carboxamide group
  • Carboxylic acid derivative
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceTan colored solid (3).
Experimental Properties
PropertyValue
Melting Point77°C
Boiling PointNot Available
Solubility0.58 mg/mL at 25°C [TOMLIN,C (2003)]
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP2.15ALOGPS
logP2.39ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)16.77ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.96 m³·mol⁻¹ChemAxon
Polarizability22.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3) ; dermal (3).
Mechanism of ToxicityPropachlor poisoning causes an induction of microsomal hepatic UDPGT activity, which produces increased clearance of thyroid hormone, T4. Decreased levels of T4 would result in increased levels of thyroid stimulating hormone (TSH). Increased levels of TSH would result in the hyperplastic and eventually tumorigenic response of the thyroid. Propachlor metabolites also bind to nAChRs in the nervous system and cause endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (6, 2, 10)
MetabolismPropachlor can be absorbed in mammals through the respiratory and gastrointestinal tracts as well as through the skin. It does not accumulate in the body, since it is rapidly metabolized through the mercapturic acid pathway (MAP). Cysteine conjugates are formed by glutathione conjugation and this conjugate has been proposed as an intermediate in the metabolic formation of mercapturic acid conjugation. It has been shown that a cysteine conjugate of propachlor is the source of sulfur in methylsulfonyl- containing metabolites, but that the carbon in the methylsulfonyl group does not come from the cysteine moiety. Propachlor is conjugated firstly with glutathione and the reaction is mediated by glutathione transferases. The glutathione conjugation provides a means for inactivation of reactive electrophiles. Glutathione conjugates have the required physico-chemical properties for biliary excretion and will generally be present, together with their catabolites cysteinyl-glycine, cysteine and N-acetylcysteine-mercapturic acid, in relatively high concentrations in the bile. After excretion with the bile, they are metabolized in the intestine where the C-S lyase present cleaves the cysteine conjugate, allowing further metabolism of sulfur to a methylsulfonyl-containing moiety. Eleven urinary metabolites, six of which are 2-methylsulfonylacetanalides have been isolated. The major fecal metabolite is identified as the cysteine conjugate. (3, 4, 5)
Toxicity ValuesLD50: 950-2176 mg/kg (Oral, Rat) (3) LC50: 3580 mg/m3 (Inhalation, Rat) (4) LD50: 380 mg/kg (Dermal, Rabbit) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesPropachlor is used on a variety of food plants, including onions, field corn, hybrid seed, silage corn, sweet corn, grain sorghum, green peas, soybeans, flax, pumpkin, and strawberries. (3)
Minimum Risk LevelNot Available
Health EffectsEye exposure may cause corneal damage. Erythematopapular contact eczema can follow exposure to propachlor. (3, 4)
SymptomsIrritation and/or severe burns of the skin, eye, esophagus or gastrointestinal tract, and the respiratory tract, depending on the route of exposure. (7)
TreatmentConsider gastric lavage, as well was dilution with milk or water after ingestion. Administer charcoal as a slurry following ingestion; however, activated charcoal should not be given to patients ingesting strong acidic or basic caustic chemicals. In case of inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. Administer symptomatic treatment as necessary. (7)
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropachlor
Chemspider IDNot Available
ChEBI ID19503
PubChem Compound ID4931
Kegg Compound IDC18759
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22953837
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=7272464