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Details

Stereochemistry ACHIRAL
Molecular Formula C16H17N3O5S
Molecular Weight 363.388
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOPRAMEZONE

SMILES

CN1N=CC(C(=O)C2=C(C)C(C3=NOCC3)=C(C=C2)S(C)(=O)=O)=C1O

InChI

InChIKey=IYMLUHWAJFXAQP-UHFFFAOYSA-N
InChI=1S/C16H17N3O5S/c1-9-10(15(20)11-8-17-19(2)16(11)21)4-5-13(25(3,22)23)14(9)12-6-7-24-18-12/h4-5,8,21H,6-7H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C16H17N3O5S
Molecular Weight 363.388
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Topramezone is a pyrazolone herbicide developed by BASF, which is also an HPPD inhibitor, being effective for the control of weeds, which are resistant to glyphosate, triazines, ALS inhibitors and the ACCase inhibitors. Topramezone has a good control efficacy for corn grassy weed and broad-leaf grass worldwide. Topramezone was registered for the first time in Canada in 2006 for application to post-emergence weed removal in cornfield, followed by releases to Latin America, North America, Japan and Germany. In 2009, BASF brought to the Chinese market its Topramezone with the trade name Arietta®. Topramezone is moderately toxic to birds, honey bees, earthworms, fish and aquatic invertebrates. Topramezone strongly inhibited 4-HPPD activity in vitro, with I(50) values of 15 and 23 nM for the enzyme isolated from S. faberi and recombinant enzyme of Arabidopsis thaliana L. respectively.

Approval Year

PubMed

PubMed

TitleDatePubMed
Evaluation of the toxicity of herbicide topramezone to Chlorella vulgaris: Oxidative stress, cell morphology and photosynthetic activity.
2017-09
Cytochrome P450 Inhibitors Reduce Creeping Bentgrass (Agrostis stolonifera) Tolerance to Topramezone.
2015
On the mechanism of action and selectivity of the corn herbicide topramezone: a new inhibitor of 4-hydroxyphenylpyruvate dioxygenase.
2007-05
Patents

Sample Use Guides

Mammals - Acute oral LD50 (mg/kg) > 2000
Route of Administration: Oral
Topramezone strongly inhibited 4-HPPD activity in vitro, with I(50) values of 15 and 23 nM for the enzyme isolated from S. faberi and recombinant enzyme of Arabidopsis thaliana L. respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:06:24 GMT 2025
Edited
by admin
on Mon Mar 31 19:06:24 GMT 2025
Record UNII
W4934JAQ65
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOPRAMEZONE
HSDB   ISO  
Common Name English
ARIETTA
Preferred Name English
IMPACT
Brand Name English
BAS-670H
Code English
TOPRAMEZONE [HSDB]
Common Name English
METHANONE, (3-(4,5-DIHYDRO-3-ISOXAZOLYL)-2-METHYL-4-(METHYLSULFONYL)PHENYL)(5-HYDROXY-1-METHYL-1H-PYRAZOL-4-YL)-
Systematic Name English
CLIO
Brand Name English
TOPRAMEZONE [ISO]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 123009
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0034722
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
ALANWOOD
topramezone
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
PUBCHEM
11302979
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
CAS
210631-68-8
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
DRUG BANK
DB14826
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
HSDB
7500
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY
FDA UNII
W4934JAQ65
Created by admin on Mon Mar 31 19:06:24 GMT 2025 , Edited by admin on Mon Mar 31 19:06:24 GMT 2025
PRIMARY