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Details

Stereochemistry RACEMIC
Molecular Formula C12H18ClNO2S
Molecular Weight 275.795
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHENAMID

SMILES

COCC(C)N(C(=O)CCl)C1=C(C)SC=C1C

InChI

InChIKey=JLYFCTQDENRSOL-UHFFFAOYSA-N
InChI=1S/C12H18ClNO2S/c1-8-7-17-10(3)12(8)14(11(15)5-13)9(2)6-16-4/h7,9H,5-6H2,1-4H3

HIDE SMILES / InChI

Molecular Formula C12H18ClNO2S
Molecular Weight 275.795
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Dimethenamid is a widely used herbicidal compound. It was originally developed by Sandoz Agro and previously marketed as a racemic mixture. It is now known that only the S-isomer exhibits herbicidal activity. The S-isomer is known by the common name dimethenamid-P. Human and animal toxicity are considered low enough for commercial use as a herbicide.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Analytical method for the determination of metolachlor, acetochlor, alachlor, dimethenamid, and their corresponding ethanesulfonic and oxanillic acid degradates in water using SPE and LC/ESI-MS/MS.
2002 Aug 1
Effect of selected sugar beet herbicides on germination of various Chenopodium album populations.
2007
Impact of environmental chemicals on key transcription regulators and correlation to toxicity end points within EPA's ToxCast program.
2010 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: referenced study was conducted in rat
Acute toxicity studies conducted in rats determined LD50's for Racemic dimethenamid as 371 mg/kg bw and 427 mg/kg bw for male and female rats respectively. Acute Toxicity of dimethenamid-P was determined in rats with a male LD50 of 429 mg/kg bw and female LD50 of 531 mg/kg bw.
Route of Administration: Oral
Germ cell mutagenicity and genotoxicity were evaluated using bacterial and mammalian cell mutagenicity tests, chromosome damage tests, and unscheduled DNA synthesis tests. These studies conclude that neither dimethenamid nor dimethenamid-P possesses genotoxic potential.
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:59:12 GMT 2023
Edited
by admin
on Sat Dec 16 07:59:12 GMT 2023
Record UNII
8504Z6C4XZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHENAMID
ISO   MI  
Common Name English
GUARDSMAN
Common Name English
SAN-582H
Code English
ACETAMIDE, 2-CHLORO-N-(2,4-DIMETHYL-3-THIENYL)-N-(2-METHOXY-1-METHYLETHYL)
Systematic Name English
DIMETHENAMID [MI]
Common Name English
DIMETHENAMID [ISO]
Common Name English
FRONTIER
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 129051
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
Code System Code Type Description
MERCK INDEX
m4506
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY Merck Index
FDA UNII
8504Z6C4XZ
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY
CAS
87674-68-8
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY
ALANWOOD
dimethenamid
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY
WIKIPEDIA
Dimethenamid
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID4032376
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY
PUBCHEM
91744
Created by admin on Sat Dec 16 07:59:12 GMT 2023 , Edited by admin on Sat Dec 16 07:59:12 GMT 2023
PRIMARY