Fenamiphos

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  • Identifiers

    CAS number
    22224-92-6

    Molecular formula
    C13H22NO3PS

    SMILES
    CCOP(=O)(NC(C)C)OC1=CC(=C(C=C1)SC)C

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Meaty 48.42%
    Roasted 41.92%
    Savory 34.65%
    Odorless 32.26%
    Sulfurous 30.27%
    Cooked 28.55%
    Grape 28.03%
    Grapefruit 26.89%
    Citrus 22.69%
    Floral 20.0%

     

    Flavor
    Odorless 31.99%
    Mild 29.95%
    Fruity 26.32%
    Sulfury 25.82%
    Bland 24.89%
    Roasted 24.18%
    Sulfurous 20.92%
    Bitter 20.89%
    Meaty 20.59%
    Scallion 20.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.2

    pKa est.
    6.6 (neutral)

    Molecular weight
    303.36 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 121 °F (EPA, 1998)
    • 49 °C
    • Off-white to tan waxy solid with a melting point of 49 °C and a vapor pressure of 4.7X10-5 mm Hg at 20 °C /Technical grade/
    • 49.2 °C
    • 121 °F

    Boiling point

    • Decomposes (NTP, 1992)
    • decomposes

    Flash point

    • 180.41 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 69 °F (NTP, 1992)
    • In water, 400 mg/L at 20 °C
    • In water, 329 mg/L at 20 °C
    • In dichloromethane, isopropanol, toluene > 200; hexane 10-20 (all in g/L, 20 °C)
    • Soluble in organic solvents
    • 0.329 mg/mL at 20 °C
    • Solubility in water, g/100ml: 0.03
    • 0.03%

  • Synonyms

    • FENAMIPHOS
    • Phenamiphos
    • 22224-92-6
    • Nemacur
    • Methaphenamiphos
    • Nemacur P
    • Fenamiphos [BSI:ISO]
    • BAY 68138
    • BAY sra 3886
    • Caswell No. 453A
    • N-[ethoxy-(3-methyl-4-methylsulfanylphenoxy)phosphoryl]propan-2-amine
    • Bayer 68138
    • Fenamiphos 90%
    • Ethyl 4-(methylthio)-m-tolyl isopropylphosphoramidate
    • Fenamiphos [ISO]
    • Phenamiphos [ISO-French]
    • CCRIS 4694
    • HSDB 6452
    • UNII-H4NO3L2HBE
    • H4NO3L2HBE
    • SRA 3886
    • Ethyl 3-methyl-4-(methylthio)phenyl (1-methylethyl)phosphoramidate
    • EINECS 244-848-1
    • ENT 27572
    • Phenamifos sulfoxide
    • EPA Pesticide Chemical Code 100601
    • NSC 195106
    • BRN 4752893
    • DTXSID3024102
    • Isopropylamino-O-ethyl-(4-methylmercapto-3-methylphenyl)phosphate
    • CHEBI:38680
    • AI3-27572
    • Fenamiphos 90per cent
    • FENAMIPHOS [MI]
    • Phosphoramidic acid, (1-methylethyl)-, ethyl 3-methyl-4-(methylthio)phenyl ester
    • Ethyl 3-methyl-4-(methylthio)phenyl isopropylphosphoramidate
    • FENAMIPHOS [HSDB]
    • Phosphoramidic acid, isopropyl-, ethyl 4-(methylthio)-m-tolyl ester
    • DTXCID404102
    • NEMACUR (BAYER CROPSCI.)
    • Isopropylphosphoramidic Acid Ethyl 4-(Methylthio)-m-tolyl Ester
    • 1-(Methylethyl)-ethyl 3-methyl-4-(methylthio)phenyl phosphoramidate
    • Phosphoramidic acid, isopropyl-, 4-(methylthio)-m-tolyl ethyl ester
    • B 68138
    • SRA-3886
    • BAY-68138
    • ethyl 4-(methylthio)m-tolyl isopropylphosphoroamidate
    • Ethyl-4-(methylthio)-m-tolyl isopropylphosphoramidate
    • NSC-195106
    • m-Cresol, 4-(methylthio)-, ethyl isopropylphosphoramidate
    • NCGC00091830-04
    • ethyl 3-methyl-4-(methylthio)phenyl isopropylamidophosphate
    • Phenamiphos (ISO-French)
    • N-(1-Methylethyl)phosphoramidic Acid Ethyl 3-Methyl-4-(methylthio)phenyl Ester
    • O-Aethyl-O-(3-methyl-4-methylthiophenyl)-isopropylamido-phosphorsaeureester
    • Phosphoramidic acid, (1-methylethyl)-, ethyl (3-methyl-4-(methylthio)phenyl) ester
    • B-68138
    • Ethyl 4-methylthio-m-tolyl isopropylphosphoramidate, 8CI
    • (RS)-(ETHYL 4-METHYLTHIO-M-TOLYL ISOPROPYLPHOSPHORAMIDATE)
    • ethyl 3-methyl-4-(methylsulfanyl)phenyl (1-methylethyl)amidophosphate
    • ethyl 3-methyl-4-(methylsulfanyl)phenyl N-(propan-2-yl)phosphoramidate
    • Ethyl 3-methyl-4-(methylthio)phenyl 1-methylethylphosphoramidate, 9CI
    • {ethoxy[3-methyl-4-(methylsulfanyl)phenoxy]phosphoryl}(propan-2-yl)amine
    • (ethoxy(3-methyl-4-(methylsulfanyl)phenoxy)phosphoryl)(propan-2-yl)amine
    • Caswell No 453A
    • Fenamiphos (ACGIH)
    • O-Aethyl-O-(3-methyl-4-methylthiophenyl)-isopropylamido-phosphorsaeureester [German]
    • SCHEMBL76010
    • MLS002454436
    • CHEMBL1313005
    • HMS3041D09
    • MSK20061
    • Tox21_400081
    • AKOS015888416
    • Fenamiphos 10 microg/mL in Cyclohexane
    • USEPA/OPP Pesticide Code: 100601
    • NCGC00091830-01
    • NCGC00091830-02
    • NCGC00091830-03
    • NCGC00091830-05
    • AC-12688
    • Fenamiphos 100 microg/mL in Acetonitrile
    • SMR000777957
    • CAS-22224-92-6
    • DB-045846
    • NS00000134
    • Fenamiphos, PESTANAL(R), analytical standard
    • C18659
    • Q32693
    • Ethyl 4(methylthio)mtolyl isopropylphosphoramidate
    • Ethyl 3methyl4(methylthio)phenyl isopropylphosphoramidate
    • Ethyl 3-methyl-4-(methylthio)phenyl isopropylphoshoramidate
    • IsopropylaminoOethyl(4methylmercapto3methylphenyl)phosphate
    • 1(Methylethyl)ethyl 3methyl4(methylthio)phenyl phosphoramidate
    • Ethyl 3methyl4(methylthio)phenyl (1methylethyl)phosphoramidate
    • Isopropylphosphoramidic acid ethyl 4-(methylthio)-m-tolylester
    • Phosphoramidic acid, isopropyl, ethyl 4(methylthio)mtolyl ester
    • Ethyl 3-methyl-4-(methylsulfanyl)phenyl isopropylamidophosphate #
    • ethyl-3-methyl-4-(methylthio)phenyl(1-methylethyl)phosphoramidate
    • OAethylO(3methyl4methylthiophenyl)isopropylamidophosphorsaeureester
    • Phosphoramidic acid, isopropyl-4-(methylthio)-m-tolyl ethyl ester
    • 1-(METHYLETHYL)-ETHYL-3-METHYL-4-(METHYLTHIO)PHENYLPHOSPHORAMIDATE
    • ETHYL 3-METHYL-4-(METHYLTHIO)PHENYL-(1-METHYLETHYL)PHOSPHORAMIDATE
    • ISOPROPYLAMINO-O-ETHYL-(4-METHYLMERCAPTO-3-METHYLPHENYL) PHOSPHATE
    • ISOPROPYLPHOSPHORAMIDIC ACID, 4-(METHYLTHIO)-M-TOLYL ETHYL ESTER
    • (1-METHYLETHYL)-PHOSPHORAMIDIC ACID, ETHYL(3-METHYL-4-(METHYLTHIO)PHENYL)ESTER
    • (1-Methylethyl)phosphoramidic acid ethyl 3-methyl-4-(methylthio)phenyl ester
    • PHOSPHORAMIDIC ACID,(1-METHYLETHYL)-, ETHYL(3-METHYL-4-(METHYLTHIO)PHENYL) ESTER
    • 244-848-1

  • Applications

    Fenamiphos (CAS 22224-92-6) is an organophosphate insecticide and nematicide used primarily in agriculture to control plant-parasitic nematodes and other soil-dwelling pests. It is applied as a soil treatment in formulations such as emulsifiable concentrates or granules for pre-plant or early-season applications in crops including vegetables, fruits, and ornamentals, in greenhouses and field settings, and is often integrated into pest management programs to suppress nematode populations in the root zone. Because of its toxicity and environmental considerations, use is typically crop- and region-specific and regulated under local pesticide laws, with formulation guidelines designed to optimize root-zone delivery while minimizing non-target exposure.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1355.4
    methanol 1843.18
    isopropanol 729.52
    water 14.26
    ethyl acetate 350.28
    n-propanol 890.03
    acetone 832.88
    n-butanol 690.93
    acetonitrile 453.58
    DMF 2449.51
    toluene 188.54
    isobutanol 462.98
    1,4-dioxane 1170.2
    methyl acetate 407.05
    THF 1755.68
    2-butanone 542.7
    n-pentanol 467.76
    sec-butanol 551.87
    n-hexane 11.8
    ethylene glycol 373.92
    NMP 1928.69
    cyclohexane 43.41
    DMSO 1996.08
    n-butyl acetate 277.35
    n-octanol 155.01
    chloroform 1779.28
    n-propyl acetate 243.53
    acetic acid 1348.81
    dichloromethane 1613.45
    cyclohexanone 1294.4
    propylene glycol 660.11
    isopropyl acetate 210.56
    DMAc 1241.88
    2-ethoxyethanol 606.01
    isopentanol 352.04
    n-heptane 9.87
    ethyl formate 412.49
    1,2-dichloroethane 986.71
    n-hexanol 360.29
    2-methoxyethanol 1381.73
    isobutyl acetate 158.57
    tetrachloromethane 99.96
    n-pentyl acetate 269.68
    transcutol 635.92
    n-heptanol 178.3
    ethylbenzene 62.95
    MIBK 216.49
    2-propoxyethanol 617.54
    tert-butanol 491.72
    MTBE 204.36
    2-butoxyethanol 317.44
    propionic acid 633.38
    o-xylene 84.96
    formic acid 728.58
    diethyl ether 280.94
    m-xylene 92.21
    p-xylene 92.42
    chlorobenzene 408.21
    dimethyl carbonate 200.28
    n-octane 6.37
    formamide 968.71
    cyclopentanone 1363.34
    2-pentanone 407.56
    anisole 165.6
    cyclopentyl methyl ether 460.44
    gamma-butyrolactone 1500.13
    1-methoxy-2-propanol 791.68
    pyridine 1047.37
    3-pentanone 264.85
    furfural 1133.36
    n-dodecane 6.99
    diethylene glycol 521.36
    diisopropyl ether 50.96
    tert-amyl alcohol 369.05
    acetylacetone 443.06
    n-hexadecane 8.15
    acetophenone 224.63
    methyl propionate 338.34
    isopentyl acetate 236.53
    trichloroethylene 1625.18
    n-nonanol 133.47
    cyclohexanol 606.09
    benzyl alcohol 308.5
    2-ethylhexanol 145.46
    isooctanol 131.33
    dipropyl ether 108.16
    1,2-dichlorobenzene 288.37
    ethyl lactate 161.86
    propylene carbonate 713.29
    n-methylformamide 1167.08
    2-pentanol 309.17
    n-pentane 18.06
    1-propoxy-2-propanol 353.62
    1-methoxy-2-propyl acetate 284.25
    2-(2-methoxypropoxy) propanol 211.41
    mesitylene 48.63
    ε-caprolactone 902.32
    p-cymene 48.93
    epichlorohydrin 1375.8
    1,1,1-trichloroethane 467.89
    2-aminoethanol 749.45
    morpholine-4-carbaldehyde 1421.05
    sulfolane 1735.69
    2,2,4-trimethylpentane 9.66
    2-methyltetrahydrofuran 866.28
    n-hexyl acetate 295.97
    isooctane 6.05
    2-(2-butoxyethoxy)ethanol 334.82
    sec-butyl acetate 134.72
    tert-butyl acetate 210.32
    decalin 12.87
    glycerin 769.98
    diglyme 520.84
    acrylic acid 625.17
    isopropyl myristate 90.06
    n-butyric acid 706.76
    acetyl acetate 244.81
    di(2-ethylhexyl) phthalate 137.13
    ethyl propionate 175.14
    nitromethane 1420.23
    1,2-diethoxyethane 228.15
    benzonitrile 366.91
    trioctyl phosphate 106.69
    1-bromopropane 376.32
    gamma-valerolactone 1936.76
    n-decanol 96.98
    triethyl phosphate 98.15
    4-methyl-2-pentanol 125.13
    propionitrile 372.19
    vinylene carbonate 676.49
    1,1,2-trichlorotrifluoroethane 1010.9
    DMS 221.48
    cumene 41.1
    2-octanol 132.31
    2-hexanone 269.65
    octyl acetate 144.34
    limonene 77.54
    1,2-dimethoxyethane 701.31
    ethyl orthosilicate 90.21
    tributyl phosphate 119.66
    diacetone alcohol 335.91
    N,N-dimethylaniline 119.14
    acrylonitrile 489.54
    aniline 376.34
    1,3-propanediol 833.61
    bromobenzene 374.9
    dibromomethane 956.09
    1,1,2,2-tetrachloroethane 1331.42
    2-methyl-cyclohexyl acetate 181.18
    tetrabutyl urea 159.52
    diisobutyl methanol 68.32
    2-phenylethanol 286.9
    styrene 90.41
    dioctyl adipate 145.28
    dimethyl sulfate 365.66
    ethyl butyrate 162.58
    methyl lactate 287.83
    butyl lactate 232.49
    diethyl carbonate 122.05
    propanediol butyl ether 355.43
    triethyl orthoformate 127.14
    p-tert-butyltoluene 49.2
    methyl 4-tert-butylbenzoate 214.93
    morpholine 1737.96
    tert-butylamine 220.47
    n-dodecanol 71.24
    dimethoxymethane 784.3
    ethylene carbonate 567.7
    cyrene 332.6
    2-ethoxyethyl acetate 322.93
    2-ethylhexyl acetate 192.12
    1,2,4-trichlorobenzene 387.34
    4-methylpyridine 819.43
    dibutyl ether 95.92
    2,6-dimethyl-4-heptanol 68.32
    DEF 579.97
    dimethyl isosorbide 394.03
    tetrachloroethylene 679.91
    eugenol 243.88
    triacetin 246.63
    span 80 280.34
    1,4-butanediol 364.83
    1,1-dichloroethane 695.9
    2-methyl-1-pentanol 273.68
    methyl formate 720.43
    2-methyl-1-butanol 368.83
    n-decane 10.8
    butyronitrile 425.24
    3,7-dimethyl-1-octanol 109.36
    1-chlorooctane 70.81
    1-chlorotetradecane 29.11
    n-nonane 9.39
    undecane 8.49
    tert-butylcyclohexane 9.56
    cyclooctane 8.77
    cyclopentanol 781.77
    tetrahydropyran 1023.6
    tert-amyl methyl ether 156.99
    2,5,8-trioxanonane 367.69
    1-hexene 71.82
    2-isopropoxyethanol 304.74
    2,2,2-trifluoroethanol 416.53
    methyl butyrate 272.34

    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