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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://sitem.herts.ac.uk/aeru/iupac/Reports/686.htm
Mammals - Acute oral LD50 (mg/kg) > 2000
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17340675
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
Edited
Mon Mar 31 19:06:24 GMT 2025
by
admin
on
Mon Mar 31 19:06:24 GMT 2025
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| Record UNII |
W4934JAQ65
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
123009
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DTXSID0034722
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topramezone
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11302979
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210631-68-8
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DB14826
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7500
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W4934JAQ65
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