Napropamide

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  • Identifiers

    CAS number
    15299-99-7

    Molecular formula
    C17H21NO2

    SMILES
    CCN(CC)C(=O)C(C)OC1=CC=CC2=CC=CC=C21

    Safety labels

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Fruity 44.89%
    Floral 34.14%
    Sweet 32.98%
    Woody 32.56%
    Grape 30.79%
    Grapefruit 28.41%
    Fresh 27.54%
    Citrus 26.05%
    Mint 25.81%
    Berry 24.78%

     

    Flavor
    Bitter 43.6%
    Fruity 35.6%
    Odorless 24.21%
    Mild 22.12%
    Bland 21.41%
    Sweet-like 19.59%
    Heather 19.58%
    Genet 19.32%
    Broom 19.32%
    Green pepper 19.2%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.19 (neutral)

    Molecular weight
    271.35 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    399°C

    Melting point expt.

    • 75 °C
    • Melting point: 74.8-75.5 °C when pure (technical is 68-70 °C)

    Flash point

    • 177.28 ˚C est.

    Solubility expt.

    • /Solubility/ in acetone, ethanol >1000, xylene 505, kerosene 62, hexane 15 (all in g/l, 20 °C); miscible with acetone, ethanol, methyl isobutyl ketone.
    • Acetone: >100; ethanol: >100; n-hexane: 1.5; 4-methylpentan-2- one: soluble; kerossene: 6.2; xylene: 50.5 g/100 ml @ 20 °C
    • In water, 73 mg/l @ 20 °C

  • Synonyms

    • Napropamide
    • 15299-99-7
    • Napropamid
    • Devrinol
    • Racemic devrinol
    • Waylay
    • N,N-Diethyl-2-(1-naphthyloxy)propionamide
    • Propionamide, N,N-diethyl-2-(1-naphthyloxy)-
    • N,N-Diethyl-2-(1-naphthalenyloxy)propionamide
    • DTXSID5024211
    • 2-(1-Naphthoxy)-N,N-diethylpropionamide
    • Propanamide, N,N-diethyl-2-(1-naphthalenyloxy)-
    • 2-(alpha-Naphthoxy)-N,N-diethylpropionamide
    • R 7465
    • R-7465
    • N,N-DIETHYL-2-(1-NAPHTHALENYLOXY)PROPANAMIDE
    • B56M9401K6
    • DTXCID504211
    • RefChem:832052
    • CHEBI:82025
    • 239-333-3
    • N,N-Diethyl-2-(1-naphthyloxy)propanamide
    • N,N-Diethyl-2-(naphthalen-1-yloxy)propanamide
    • Napropamide [ISO]
    • N,N-Diethyl-2-(1-Naphthyloxy)propanamde
    • N,N-diethyl-2-naphthalen-1-yloxypropanamide
    • MFCD00055354
    • Napropamide 10 microg/mL in Cyclohexane
    • Napropamide 100 microg/mL in Cyclohexane
    • 2-(.alpha.-Naphthoxy)-N,N-Diethylpropionamide
    • Caswell No. 590A
    • Napropamide [ISO:PROP]
    • CAS-15299-99-7
    • HSDB 6710
    • EINECS 239-333-3
    • EPA Pesticide Chemical Code 103001
    • BRN 2217870
    • Napromide
    • UNII-B56M9401K6
    • Napropamide (Standard)
    • 2-(alpha-Naphthoxy)-N,N-diaethyl-propionsaeureamid [German]
    • DEVRINOL [HSDB]
    • NAPROPAMIDE [MI]
    • Propanamide, N,N-diethyl-2-(1-naphthalenyloxy)-, (R)-
    • SCHEMBL54956
    • 2-(alpha-Naphthoxy)-N,N-diaethyl-propionsaeureamid
    • orb3029187
    • CHEMBL1877460
    • DEVRINOL, (+/-)-
    • SCHEMBL29350504
    • CHEBI:83771
    • HY-B1972R
    • WXZVAROIGSFCFJ-UHFFFAOYSA-
    • HY-B1972
    • MSK22338
    • Tox21_201824
    • Tox21_300655
    • AKOS004109919
    • CS-5198
    • NCGC00163768-01
    • NCGC00163768-02
    • NCGC00163768-03
    • NCGC00163768-04
    • NCGC00163768-05
    • NCGC00254563-01
    • NCGC00259373-01
    • AS-12500
    • SY276679
    • DB-043170
    • N,N-Diethyl-2-(1-naphthyloxy)propanamide #
    • NS00000068
    • Napropamid, PESTANAL(R), analytical standard
    • C18868
    • D94768
    • N,N-Diethyl-2-(1-naphthyloxy)propanamide, 97%
    • 299N997
    • A809371
    • N,N-Diethyl-2-[(naphthalen-1-yl)oxy]propanamide
    • Q27157194
    • N,N-diethyl-2-(1-naphthyloxy)propanamide;N,N-Diethyl-2-(1-Naphthyloxy)propanamde
    • InChI=1/C17H21NO2/c1-4-18(5-2)17(19)13(3)20-16-12-8-10-14-9-6-7-11-15(14)16/h6-13H,4-5H2,1-3H3
    • 15299-99-7

  • Applications

    Napropamide (CAS 15299-99-7) is used as a soil-applied pre-emergence herbicide to control annual grasses and some broadleaf weeds in agriculture, particularly in vegetables and row crops; it is commonly formulated into emulsifiable concentrates or suspension formulations for field and greenhouse use. In commercial horticulture, including protected-culture operations, it helps suppress weed emergence before crop sowing or transplanting. As an active ingredient in herbicide products, Napropamide is incorporated into formulation programs for weed management across crop systems, often as part of integrated weed-management strategies. Its use is governed by local regulations and formulation limits, and effectiveness depends on soil type and crop schedule.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 129.82
    methanol 195.06
    isopropanol 85.45
    water 2.8
    ethyl acetate 515.05
    n-propanol 127.96
    acetone 568.07
    n-butanol 135.72
    acetonitrile 609.16
    DMF 624.47
    toluene 253.66
    isobutanol 105.85
    1,4-dioxane 636.78
    methyl acetate 471.65
    THF 543.0
    2-butanone 425.15
    n-pentanol 121.79
    sec-butanol 98.71
    n-hexane 56.07
    ethylene glycol 31.4
    NMP 545.38
    cyclohexane 109.32
    DMSO 486.4
    n-butyl acetate 395.23
    n-octanol 49.99
    chloroform 2587.14
    n-propyl acetate 376.59
    acetic acid 459.54
    dichloromethane 3670.92
    cyclohexanone 699.83
    propylene glycol 21.84
    isopropyl acetate 274.8
    DMAc 562.61
    2-ethoxyethanol 225.12
    isopentanol 135.84
    n-heptane 24.93
    ethyl formate 330.17
    1,2-dichloroethane 2309.31
    n-hexanol 103.41
    2-methoxyethanol 270.25
    isobutyl acetate 222.71
    tetrachloromethane 365.11
    n-pentyl acetate 230.66
    transcutol 584.81
    n-heptanol 61.62
    ethylbenzene 166.49
    MIBK 207.99
    2-propoxyethanol 228.3
    tert-butanol 112.76
    MTBE 216.35
    2-butoxyethanol 146.3
    propionic acid 242.94
    o-xylene 177.86
    formic acid 155.67
    diethyl ether 435.46
    m-xylene 161.35
    p-xylene 221.57
    chlorobenzene 658.69
    dimethyl carbonate 291.06
    n-octane 14.07
    formamide 345.23
    cyclopentanone 650.03
    2-pentanone 352.51
    anisole 303.12
    cyclopentyl methyl ether 321.33
    gamma-butyrolactone 856.1
    1-methoxy-2-propanol 156.42
    pyridine 664.99
    3-pentanone 413.38
    furfural 750.3
    n-dodecane 9.76
    diethylene glycol 168.6
    diisopropyl ether 107.24
    tert-amyl alcohol 119.5
    acetylacetone 511.85
    n-hexadecane 11.62
    acetophenone 297.52
    methyl propionate 395.03
    isopentyl acetate 318.7
    trichloroethylene 3194.08
    n-nonanol 51.52
    cyclohexanol 173.21
    benzyl alcohol 190.44
    2-ethylhexanol 91.56
    isooctanol 59.81
    dipropyl ether 170.11
    1,2-dichlorobenzene 666.62
    ethyl lactate 121.87
    propylene carbonate 490.0
    n-methylformamide 359.3
    2-pentanol 91.15
    n-pentane 38.53
    1-propoxy-2-propanol 145.46
    1-methoxy-2-propyl acetate 281.63
    2-(2-methoxypropoxy) propanol 137.86
    mesitylene 108.27
    ε-caprolactone 565.58
    p-cymene 89.58
    epichlorohydrin 1168.63
    1,1,1-trichloroethane 1234.38
    2-aminoethanol 62.95
    morpholine-4-carbaldehyde 537.95
    sulfolane 815.41
    2,2,4-trimethylpentane 24.91
    2-methyltetrahydrofuran 427.27
    n-hexyl acetate 231.68
    isooctane 15.23
    2-(2-butoxyethoxy)ethanol 166.13
    sec-butyl acetate 225.28
    tert-butyl acetate 263.01
    decalin 50.96
    glycerin 50.89
    diglyme 485.5
    acrylic acid 276.88
    isopropyl myristate 84.98
    n-butyric acid 334.0
    acetyl acetate 453.18
    di(2-ethylhexyl) phthalate 88.27
    ethyl propionate 345.16
    nitromethane 1022.14
    1,2-diethoxyethane 365.57
    benzonitrile 338.58
    trioctyl phosphate 57.32
    1-bromopropane 726.44
    gamma-valerolactone 750.75
    n-decanol 39.38
    triethyl phosphate 158.97
    4-methyl-2-pentanol 62.85
    propionitrile 368.81
    vinylene carbonate 577.76
    1,1,2-trichlorotrifluoroethane 542.61
    DMS 351.97
    cumene 108.37
    2-octanol 47.57
    2-hexanone 273.16
    octyl acetate 109.9
    limonene 116.49
    1,2-dimethoxyethane 549.58
    ethyl orthosilicate 144.0
    tributyl phosphate 90.55
    diacetone alcohol 171.87
    N,N-dimethylaniline 191.99
    acrylonitrile 498.93
    aniline 262.75
    1,3-propanediol 109.16
    bromobenzene 807.26
    dibromomethane 2069.46
    1,1,2,2-tetrachloroethane 2065.89
    2-methyl-cyclohexyl acetate 206.71
    tetrabutyl urea 114.83
    diisobutyl methanol 57.89
    2-phenylethanol 170.51
    styrene 238.4
    dioctyl adipate 133.78
    dimethyl sulfate 375.99
    ethyl butyrate 294.11
    methyl lactate 126.72
    butyl lactate 132.19
    diethyl carbonate 243.87
    propanediol butyl ether 76.64
    triethyl orthoformate 190.64
    p-tert-butyltoluene 76.92
    methyl 4-tert-butylbenzoate 189.17
    morpholine 506.91
    tert-butylamine 90.43
    n-dodecanol 32.88
    dimethoxymethane 467.14
    ethylene carbonate 494.51
    cyrene 168.33
    2-ethoxyethyl acetate 337.63
    2-ethylhexyl acetate 274.71
    1,2,4-trichlorobenzene 652.05
    4-methylpyridine 541.72
    dibutyl ether 139.01
    2,6-dimethyl-4-heptanol 57.89
    DEF 466.75
    dimethyl isosorbide 308.52
    tetrachloroethylene 1594.87
    eugenol 179.34
    triacetin 237.26
    span 80 100.97
    1,4-butanediol 63.35
    1,1-dichloroethane 1219.27
    2-methyl-1-pentanol 127.48
    methyl formate 361.49
    2-methyl-1-butanol 131.93
    n-decane 15.56
    butyronitrile 329.57
    3,7-dimethyl-1-octanol 61.11
    1-chlorooctane 75.52
    1-chlorotetradecane 32.85
    n-nonane 14.62
    undecane 11.9
    tert-butylcyclohexane 37.2
    cyclooctane 32.69
    cyclopentanol 150.26
    tetrahydropyran 509.91
    tert-amyl methyl ether 181.94
    2,5,8-trioxanonane 279.43
    1-hexene 146.98
    2-isopropoxyethanol 156.4
    2,2,2-trifluoroethanol 257.71
    methyl butyrate 437.27

    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