<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1091</id>
  <title>T3D1087</title>
  <common-name>Butachlor</common-name>
  <description>Butachlor 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. (A252) </description>
  <cas>23184-66-9</cas>
  <pubchem-id>31677</pubchem-id>
  <chemical-formula>C17H26ClNO2</chemical-formula>
  <weight>311.165210</weight>
  <appearance>Light yellow to purple liquid with a faint, sweet odor (L915).</appearance>
  <melting-point>-2.8°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>0.02 mg/mL at 20°C [TOMLIN,C (1997)]</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Dermal  (A572) ;  eye contact  (A572) ; inhalation (A572).</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Binds to nAChRs in nervous systems. Also causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (T10, A590)</mechanism-of-toxicity>
  <metabolism>In 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. (T80, A572)
</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity (not listed by IARC). (L135)</carcinogenicity>
  <use-source>Butachlor is commonly used herbicide. Elevated concentrations of this herbicide and their degradation products have been detected in surface and groundwater. (A252)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Coronary spasm, hypotension, and sinus tachycardia may occur following exposure. Aspiration of insecticide containing petroleum
distillate may result in pneumonitis. Pancreatitis can result from ingestion. (T36). </health-effects>
  <symptoms>CNS 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 (T36).</symptoms>
  <treatment>Consider 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. (T36)</treatment>
  <created-at type="dateTime">2009-06-18T21:54:33Z</created-at>
  <updated-at type="dateTime">2026-03-26T20:57:14Z</updated-at>
  <interacting-proteins>Binds to nAChRs in nervous systems. B tachlor is initially conjugated with GSH to form BGSC by the enzyme glutathione S-transferase in the liver (T10, A272).</interacting-proteins>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C10931</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>C054409</ctd-id>
  <stitch-id>Butachlor</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id>7726</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins>Glutathione S-transferase P (P09211) 
Glutathione S-transferase Mu 1 (P09488) 
Glutathione S-transferase A1 (P08263) 
Glutathione S-transferase theta-2 (P30712) 
Glutathione S-transferase Mu 4 (Q03013) 
Glutathione S-transferase theta-1 (P30711) 
Glutathione S-transferase A4 (O15217) 
Glutathione S-transferase A2 (P09210) 
Glutathione S-transferase A3 (Q16772) 
Glutathione S-transferase Mu 3 (P21266) 
Glutathione S-transferase omega-1 (P78417) 
Glutathione S-transferase kappa 1 (Q9Y2Q3)
Glutathione S-transferase Mu 2 (P28161) 
Glutathione S-transferase omega-2 (Q9H4Y5)
Glutathione S-transferase A5 (Q7RTV2) 
Glutathione S-transferase Mu 5 (P46439) 
Glutathione S-transferase theta-4 (A8MPT4)
Maleylacetoacetate isomerase (O43708) 
Microsomal glutathione S-transferase 1 (P10620) 
Microsomal glutathione S-transferase 2 (Q99735) 
Microsomal glutathione S-transferase 3 (O14880)
Cytochrome P450 2B6 (P20813)
Cytochrome P450 3A4 (P08684)
(A269, T80, A572)</metabolizing-proteins>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC</moldb-smiles>
  <moldb-formula>C17H26ClNO2</moldb-formula>
  <moldb-inchi>InChI=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</moldb-inchi>
  <moldb-inchikey>HKPHPIREJKHECO-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">311.847</moldb-average-mass>
  <moldb-mono-mass type="decimal">311.165206788</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL1399036</chembl-id>
  <chemspider-id>29376</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM000929</chemdb-id>
  <dsstox-id>DTXSID3034402</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00003366</susdat-id>
  <iupac>N-(butoxymethyl)-2-chloro-N-(2,6-diethylphenyl)acetamide</iupac>
</compound>
