topramezone

Modify Date: 2024-01-02 21:18:51

topramezone Structure
topramezone structure
Common Name topramezone
CAS Number 210631-68-8 Molecular Weight 363.388
Density 1.5±0.1 g/cm3 Boiling Point 590.5±60.0 °C at 760 mmHg
Molecular Formula C16H17N3O5S Melting Point N/A
MSDS Chinese USA Flash Point 310.9±32.9 °C
Symbol GHS08 GHS09
GHS08, GHS09
Signal Word Danger

 Use of topramezone


Topramezone is a potent 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitor. Topramezone is a herbicide, used for the post-emergence control of broadleaf and grass weeds in corn[1].

 Names

Name topramezone
Synonym More Synonyms

 topramezone Biological Activity

Description Topramezone is a potent 4-hydroxyphenylpyruvate dioxygenase (4-HPPD) inhibitor. Topramezone is a herbicide, used for the post-emergence control of broadleaf and grass weeds in corn[1].
In Vitro Topramezone (5, 10, 20, 30, 45 mg/L; 24-96 h) inhibits algal (C. vulgaris) growth by triggering oxidative stress, damaging cell morphology and photosynthetic activity during the exposure[1]. Topramezone (20 mg/L; 24, 48, 72 and 96 h) disrupts the photosynthetic system, by decreasing the content of photosynthetic pigments, and induces ROS (oxidative stress) with an increase of MDA in a time-dependent manner[1]. Topramezone (20 mg/L; 96 h) compromises the integrity of the cells, damages chloroplasts and membranes in algal cells and triggers apoptosis[1]. Topramezone (0.1 nM-0.1 mM; 30 min) exhibits selectivity and inhibits 4-HPPD (recombinant enzyme protein) activity in vitro, with IC50s of 15 nM (Setaria faberi), 23 nM (Arabidopsis thaliana), and 180 nM (Corn)[2]. topramezone (foliar-applied; containing [14C]topramezone of 0.29 µg; 24 and 48 h) is metabolized faster in corn than in the weeds[2].
References

[1]. Zhao F, et al. Evaluation of the toxicity of herbicide topramezone to Chlorella vulgaris: Oxidative stress, cell morphology and photosynthetic activity. Ecotoxicol Environ Saf. 2017 Sep. 143:129-135.

[2]. Grossmann K, et al. On the mechanism of action and selectivity of the corn herbicide topramezone: a new inhibitor of 4-hydroxyphenylpyruvate dioxygenase. Pest Manag Sci. 2007 May. 63(5):429-39.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 590.5±60.0 °C at 760 mmHg
Molecular Formula C16H17N3O5S
Molecular Weight 363.388
Flash Point 310.9±32.9 °C
Exact Mass 363.088898
PSA 119.23000
LogP 0.96
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.670

 Safety Information

Symbol GHS08 GHS09
GHS08, GHS09
Signal Word Danger
Hazard Statements H360-H410
Precautionary Statements P201-P273-P308 + P313-P501
Personal Protective Equipment Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes T,N
Risk Phrases 61-50/53
Safety Phrases 53-45-60-61
RIDADR UN3077 9/PG 3

 Synonyms

4-[2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl ]-1-methyl-5-hydroxy-1H-pyrazole
4-[3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-5-hydroxy-1-methylpyrazole
4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1H-pyrazol-3-one
Methanone, [3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)-
[3-(4,5-Dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
11322047
T5NO EUTJ ER B1 FSW1 CV- DTNNJ A1 EQ
1-methyl-4-(3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methyl-sulfonylbenzoyl)-5-hydroxypyrazole
[3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
[3-(4,5-dihydro-1,2-oxazol-3-yl)-4-(methanesulfonyl)-2-methylphenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
benzuocaotong
[3-(4,5-Dihydro-1,2-oxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
4-[3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methylsulfonyl-benzoyl]-1-methyl-5-hydroxy-1H-pyrazole
topramezone
[3-(4,5-dihydro-1,2-oxazol-3-yl)-4-mesyl-o-tolyl](5-hydroxy-1-methyl-1H-pyrazole-4-yl)methanone
[3-(4,5-dihydro-1,2-oxazol-3-yl)-4-mesyl-o-tolyl](5-hydroxy-1-methylpyrazol-4-yl)methanone
[3-(4,5-Dihydro-1,2-oxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanon
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