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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Mammals - Acute oral LD50 (mg/kg) > 2000
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
W4934JAQ65
Record Status Validated (UNII)
Record Version