Topramezone

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  • Identifiers

    CAS number
    210631-68-8

    Molecular formula
    C16H17N3O5S

    SMILES
    CC1=C(C=CC(=C1C2=NOCC2)S(=O)(=O)C)C(=O)C3=CNN(C3=O)C

    Safety labels

  • Odor profile

    Fragrance
    Odorless 65.3%
    Roasted 33.37%
    Cooked 25.56%
    Burnt 25.13%
    Popcorn 22.69%
    Savory 20.77%
    Nutty 20.25%
    Bitter 19.19%
    Meaty 18.94%
    Caramellic 17.11%

     

    Flavor
    Bitter 91.95%
    Odorless 28.64%
    Taco 19.54%
    Bread crust 19.5%
    Bland 19.42%
    Nitrile 19.32%
    Very strong 18.49%
    Roasted peanuts 18.47%
    Cedarleaf 18.24%
    Indole 18.18%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    5.51 (weak acid)

    Molecular weight
    363.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Very slow

    Boiling point est.
    767°C

    Flash point

    • 287.43 ˚C est.

  • Synonyms

    • Topramezone
    • 210631-68-8
    • Topramezone [ISO]
    • W4934JAQ65
    • UNII-W4934JAQ65
    • 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)-
    • DTXSID0034722
    • HSDB 7500
    • Topramezone 10 microg/mL in Acetonitrile
    • [3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
    • Clio
    • (3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl)(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
    • (3-(4,5-dihydro-isoxazol-3-yl)-4-methanesulfonyl-2-methylphenyl)(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
    • Armezon
    • METHANONE, (3-(4,5-DIHYDRO-3-ISOXAZOLYL)-2-METHYL-4-(METHYLSULFONYL)PHENYL)(5-HYDROXY-1-METHYL-1H-PYRAZOL-4-YL)-
    • ARIETTA
    • TOPRAMEZONE [HSDB]
    • SCHEMBL116121
    • BAS-670H
    • orb1983004
    • orb3025017
    • CHEMBL2272076
    • CHEMBL3145388
    • DTXCID8014722
    • SCHEMBL12155098
    • SCHEMBL29414011
    • SCHEMBL29566850
    • BPPVUXSMLBXYGG-UHFFFAOYSA-N
    • CHEBI:131999
    • MSK22584
    • Tox21_302441
    • MFCD09953760
    • DB14826
    • NCGC00255588-01
    • FT172758
    • HY-144900
    • CAS-210631-68-8
    • CS-0541809
    • NS00021846
    • Topramezone, PESTANAL(R), analytical standard
    • Q1168918
    • (3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl)(5-hydroxy-1-methyl-1H-pyrazol-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)methanone
    • 1-Methyl-4-(3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl)-5-hydroxypyrazole
    • 4-[3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methylsulfonyl-benzoyl]-2-methyl-1H-pyrazol-3-one
    • 4-[3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl]-5-hydroxy-1-methylpyrazole
    • 5-hydroxy-1-methylpyrazol-4-yl 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)phenyl ketone
    • 210631-68-8

  • Applications

    Topramezone (CAS 210631-68-8) is used as the active ingredient in selective herbicide products for weed control in agricultural crops and turf management. It functions as a post-emergence inhibitor of 4-hydroxyphenylpyruvate dioxygenase (HPPD), disrupting carotenoid biosynthesis and causing bleaching and growth inhibition in susceptible weeds. Real-world applications include post-emergence weed control in field crops, cereals, and turfgrass used in landscaping, golf courses, and professional maintenance, with formulations designed to optimize uptake and crop tolerance and subject to local regulatory requirements.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.39
    methanol 0.96
    isopropanol 0.18
    water 0.02
    ethyl acetate 1.48
    n-propanol 0.25
    acetone 3.69
    n-butanol 0.19
    acetonitrile 4.95
    DMF 25.76
    toluene 0.12
    isobutanol 0.18
    1,4-dioxane 3.58
    methyl acetate 2.95
    THF 5.54
    2-butanone 3.2
    n-pentanol 0.21
    sec-butanol 0.15
    n-hexane 0.0
    ethylene glycol 0.59
    NMP 34.67
    cyclohexane 0.01
    DMSO 26.14
    n-butyl acetate 1.6
    n-octanol 0.21
    chloroform 4.53
    n-propyl acetate 1.55
    acetic acid 3.38
    dichloromethane 5.84
    cyclohexanone 8.44
    propylene glycol 0.31
    isopropyl acetate 0.77
    DMAc 42.72
    2-ethoxyethanol 3.08
    isopentanol 0.24
    n-heptane 0.0
    ethyl formate 2.9
    1,2-dichloroethane 2.84
    n-hexanol 0.16
    2-methoxyethanol 6.11
    isobutyl acetate 0.8
    tetrachloromethane 0.16
    n-pentyl acetate 1.05
    transcutol 3.58
    n-heptanol 0.23
    ethylbenzene 0.12
    MIBK 0.98
    2-propoxyethanol 4.05
    tert-butanol 0.21
    MTBE 0.11
    2-butoxyethanol 2.41
    propionic acid 1.32
    o-xylene 0.12
    formic acid 5.46
    diethyl ether 0.14
    m-xylene 0.08
    p-xylene 0.28
    chlorobenzene 0.9
    dimethyl carbonate 3.32
    n-octane 0.0
    formamide 11.19
    cyclopentanone 12.25
    2-pentanone 1.49
    anisole 0.97
    cyclopentyl methyl ether 0.44
    gamma-butyrolactone 16.17
    1-methoxy-2-propanol 2.76
    pyridine 5.64
    3-pentanone 1.33
    furfural 20.87
    n-dodecane 0.01
    diethylene glycol 5.7
    diisopropyl ether 0.03
    tert-amyl alcohol 0.2
    acetylacetone 4.83
    n-hexadecane 0.01
    acetophenone 3.0
    methyl propionate 2.23
    isopentyl acetate 1.48
    trichloroethylene 9.58
    n-nonanol 0.27
    cyclohexanol 0.27
    benzyl alcohol 1.67
    2-ethylhexanol 0.16
    isooctanol 0.22
    dipropyl ether 0.17
    1,2-dichlorobenzene 1.23
    ethyl lactate 2.32
    propylene carbonate 6.47
    n-methylformamide 8.34
    2-pentanol 0.07
    n-pentane 0.0
    1-propoxy-2-propanol 2.04
    1-methoxy-2-propyl acetate 3.09
    2-(2-methoxypropoxy) propanol 4.03
    mesitylene 0.06
    ε-caprolactone 6.51
    p-cymene 0.14
    epichlorohydrin 13.38
    1,1,1-trichloroethane 1.05
    2-aminoethanol 0.67
    morpholine-4-carbaldehyde 24.6
    sulfolane 26.81
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 1.29
    n-hexyl acetate 1.02
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.23
    sec-butyl acetate 0.67
    tert-butyl acetate 0.77
    decalin 0.01
    glycerin 2.05
    diglyme 7.7
    acrylic acid 2.57
    isopropyl myristate 0.5
    n-butyric acid 1.49
    acetyl acetate 1.95
    di(2-ethylhexyl) phthalate 1.75
    ethyl propionate 1.46
    nitromethane 20.45
    1,2-diethoxyethane 1.01
    benzonitrile 4.01
    trioctyl phosphate 0.95
    1-bromopropane 0.33
    gamma-valerolactone 26.29
    n-decanol 0.2
    triethyl phosphate 1.53
    4-methyl-2-pentanol 0.08
    propionitrile 2.34
    vinylene carbonate 8.09
    1,1,2-trichlorotrifluoroethane 15.97
    DMS 2.67
    cumene 0.1
    2-octanol 0.13
    2-hexanone 1.71
    octyl acetate 0.77
    limonene 0.15
    1,2-dimethoxyethane 7.23
    ethyl orthosilicate 0.98
    tributyl phosphate 1.2
    diacetone alcohol 2.34
    N,N-dimethylaniline 0.69
    acrylonitrile 6.42
    aniline 0.62
    1,3-propanediol 1.18
    bromobenzene 0.66
    dibromomethane 1.83
    1,1,2,2-tetrachloroethane 4.84
    2-methyl-cyclohexyl acetate 1.71
    tetrabutyl urea 2.61
    diisobutyl methanol 0.11
    2-phenylethanol 1.64
    styrene 0.19
    dioctyl adipate 1.65
    dimethyl sulfate 9.34
    ethyl butyrate 1.5
    methyl lactate 3.75
    butyl lactate 1.86
    diethyl carbonate 1.6
    propanediol butyl ether 1.56
    triethyl orthoformate 1.17
    p-tert-butyltoluene 0.1
    methyl 4-tert-butylbenzoate 3.04
    morpholine 4.05
    tert-butylamine 0.06
    n-dodecanol 0.14
    dimethoxymethane 5.26
    ethylene carbonate 5.6
    cyrene 8.81
    2-ethoxyethyl acetate 2.5
    2-ethylhexyl acetate 1.11
    1,2,4-trichlorobenzene 2.09
    4-methylpyridine 3.48
    dibutyl ether 0.22
    2,6-dimethyl-4-heptanol 0.11
    DEF 4.36
    dimethyl isosorbide 8.98
    tetrachloroethylene 2.63
    eugenol 4.64
    triacetin 2.87
    span 80 2.29
    1,4-butanediol 0.64
    1,1-dichloroethane 0.98
    2-methyl-1-pentanol 0.26
    methyl formate 7.84
    2-methyl-1-butanol 0.2
    n-decane 0.01
    butyronitrile 1.55
    3,7-dimethyl-1-octanol 0.24
    1-chlorooctane 0.09
    1-chlorotetradecane 0.05
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.49
    tetrahydropyran 0.81
    tert-amyl methyl ether 0.13
    2,5,8-trioxanonane 6.84
    1-hexene 0.02
    2-isopropoxyethanol 1.56
    2,2,2-trifluoroethanol 3.51
    methyl butyrate 2.53

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction