Butachlor (CHEM000929)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (35)XML
Record Information
Version1.0
Creation Date2009-06-18 21:54:33 UTC
Update Date2026-03-26 20:57:14 UTC
Accession NumberCHEM000929
Identification
Common NameButachlor
ClassSmall Molecule
DescriptionButachlor is a selective herbicide used worldwide in corn, soybean and other crop cultures. Elevated concentrations of these herbicides and their degradation products have been detected in surface and groundwater. (1)
Contaminant Sources
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Aromatic Hydrocarbon
  • Chloroacetanilide
  • Ether
  • Organic Compound
  • Organochloride
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2',6'-Diethyl-N-butoxymethyl-2-chloroacetanilideChEBI
2',6'-Diethyl-N-butoxymethyl-alpha-chloroacetanilideChEBI
2-Chloro-2',6'-diethyl-N-(butoxymethyl)acetanilideChEBI
N-(Butoxymethyl)-2-chloro-2',6'-diethylacetanilideChEBI
N-Butoxymethyl-alpha-chloro-2',6'-diethylacetanilideChEBI
2',6'-Diethyl-N-butoxymethyl-a-chloroacetanilideGenerator
2',6'-Diethyl-N-butoxymethyl-α-chloroacetanilideGenerator
N-Butoxymethyl-a-chloro-2',6'-diethylacetanilideGenerator
N-Butoxymethyl-α-chloro-2',6'-diethylacetanilideGenerator
MacheteMeSH
Chemical FormulaC17H26ClNO2
Average Molecular Mass311.847 g/mol
Monoisotopic Mass311.165 g/mol
CAS Registry Number23184-66-9
IUPAC NameN-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide
Traditional Namemachette
SMILESCCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC
InChI IdentifierInChI=1S/C17H26ClNO2/c1-4-7-11-21-13-19(16(20)12-18)17-14(5-2)9-8-10-15(17)6-3/h8-10H,4-7,11-13H2,1-3H3
InChI KeyHKPHPIREJKHECO-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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceLight yellow to purple liquid with a faint, sweet odor (7).
Experimental Properties
PropertyValue
Melting Point-2.8°C
Boiling PointNot Available
Solubility0.02 mg/mL at 20°C [TOMLIN,C (1997)]
Predicted Properties
PropertyValueSource
Water Solubility0.0072 g/LALOGPS
logP4.2ALOGPS
logP4.92ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.6ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity87.8 m³·mol⁻¹ChemAxon
Polarizability34.88 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-6490000000-def411cb42e6b815375eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4i-9600000000-b9b65db505e3c9f86f26Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0a4i-9400000000-dabc9f6c707148a3d27dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-4090000000-68603be0c7024c7bddfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4r-9240000000-94097fcaa538458feb79Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a5a-7900000000-e313e04f341d97ef8c85Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a4j-9600000000-967f9c42b1b2fa44a92cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0a4i-9600000000-53ec78318e7c9b9981b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-5189000000-23bfb58c2f30d4174236Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vr-5971000000-3ae9d00b53f048370df4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5a-9800000000-f018159acc09d94f2fd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-4049000000-15e46768f116f8578999Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-4891000000-3a8af632d777c5e08699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dj-5940000000-11eabdbd0a09f1c75b76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0290000000-39d8668a9094eb09df83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gr-0950000000-61957bab6f4c445d280eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2900000000-9d0ad0791ed4f5eb574dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-7aa96f89cfc5656d0e44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-022i-3592000000-ddefedceeb8b2c691136Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006t-0930000000-93f0a9aabe8357d9f47fSpectrum
MSMass Spectrum (Electron Ionization)splash10-004i-6920000000-40f0ed5d4785dab2b0c3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureDermal (4) ; eye contact (4) ; inhalation (4).
Mechanism of ToxicityBinds to nAChRs in nervous systems. Also causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (8, 5)
MetabolismIn varying degrees, butachlor absorbed from the gut and also by the lung and across the skin. Butachlor metabolism is complex due to extensive biliary excretion, intestinal microbial metabolism, and enterohepatic circulation of metabolites. Metabolism in rats follows three major pathways: initial conjugation with glutathione (via glutathione S-transferases) followed by mercapturic acid pathway metabolism; cytochrome P-450-mediated hydroxylation of the aromatic ring, its ethyl groups and the N- butoxymethylene group; and cleavage of the amide bonds via aryl amidase to form 2,6-diethyl aniline, which is further oxidized to 4-amino-3,5-diethylphenol. (10, 4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (6)
Uses/SourcesButachlor is commonly used herbicide. Elevated concentrations of this herbicide and their degradation products have been detected in surface and groundwater. (1)
Minimum Risk LevelNot Available
Health EffectsCoronary spasm, hypotension, and sinus tachycardia may occur following exposure. Aspiration of insecticide containing petroleum distillate may result in pneumonitis. Pancreatitis can result from ingestion. (9).
SymptomsCNS excitation, seizures, tremor, ataxia, agitation, nervousness, and amnesia may occur. Kelthane, perthane, methoxychlor, and hexachlorobenzene have little CNS toxicity; in significant overdose CNS depression may occur. Nausea, vomiting, and diarrhea may follow ingestion (9).
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. (9)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0249451
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-18941
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButachlor
Chemspider ID29376
ChEBI ID3230
PubChem Compound IDNot Available
Kegg Compound IDC10931
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20183093
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25097380
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25378033
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25528421
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25708297
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25763539
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26027538
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26368393
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26372161
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=26461443
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=26946506
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26971167
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=27071456
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=27182978
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=27419617
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=27480594
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=27514993
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27522569
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=27579872
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=27943158
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=27974272
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=27987462
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28045224
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=28190210
25.