Thiophanate-Methyl

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  • Identifiers

    CAS number
    23564-05-8

    Molecular formula
    C12H14N4O4S2

    SMILES
    COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 56.55%
    Savory 37.59%
    Meaty 35.53%
    Sulfurous 30.66%
    Cooked 29.05%
    Roasted 24.39%
    Cheesy 24.06%
    Grape 21.98%
    Fruity 21.27%
    Cooling 19.11%

     

    Flavor
    Odorless 49.15%
    Bitter 41.11%
    Mild 32.09%
    Very mild 26.36%
    Fruity 26.08%
    Bland 24.87%
    Yeast 22.1%
    Cooked 19.77%
    Orange flower 19.74%
    Nitrile 19.24%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    9.82 (weak base)

    Molecular weight
    342.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    707°C

    Melting point expt.

    • 342 °F (Decomposes) (NTP, 1992)
    • 172 °C (decomposes)
    • MP: 181.5 - 182.5 °C
    • 342 °F

    Flash point

    • 231.67 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • Sparingly soluble in most organic solvents at 25 °C (2.9 g/100 mL acetone; 7.8X10-1 g/100 mL methanol; 8.4X10-1 g/100 mL ethyl acetate; 7.3X10-2 g/100 mL dichloromethane; 1.8X10-2 g/100 mL n-octanol; 1.1X10-2 g/100 mL xylene; and 4.7X10-5 g/100 mL n-hexane)
    • In acetone 58.1, cyclohexanone 43, methanol 29.2, acetonitrile 24.4, ethyl acetate 11.9 (all in g/kg, 23 °C). Slightly soluble in hexane.
    • Thiophanate methyl is slightly soluble in most organic solvents... .
    • Soluble in acetone, methanol, chloroform and acetonitrile.
    • For more Solubility (Complete) data for THIOPHANATE METHYL (6 total), please visit the HSDB record page.

  • Synonyms

    • Thiophanate-methyl
    • 23564-05-8
    • Methylthiofanate
    • THIOPHANATE METHYL
    • Thiophanate M
    • Methyl topsin
    • Methylthiophanate
    • Mildothane
    • Neotopsin
    • Methyl thiophanate
    • Fungo
    • Cercobin methyl
    • Topsin Methyl
    • Caligran
    • Metoben
    • Enovit methyl
    • Enovit M
    • Topsin M
    • Cycosin
    • Easout
    • Thiopan
    • Enovit Super
    • Cercobin M
    • Topsin NF-44
    • Sipcaplant
    • Sipcasan
    • Sipcavit
    • Rilon
    • Trevin
    • Topsin wp methyl
    • Pelt 14
    • Tiofanate metile
    • Fungo 50
    • NF 44
    • o-Bis(3-methoxycarbonyl-2-thioureido)benzene
    • 1,2-Bis(methoxycarbonylthioureido)benzene
    • Fungitox
    • Topsin turf and ornamentals
    • Topsin NF 44
    • Enovit-methyl
    • BAS 32500F
    • PELT-44
    • Dimethyl 4,4'-o-phenylenebis(3-thioallophanate)
    • TD 1771
    • PEI 190
    • CERCOBIN-M
    • Sigma
    • F 6385
    • 1,2-Di-(3-methoxycarbonyl-2-thioureido)benzene
    • 1,2-Bis(3-(methoxycarbonyl)-2-thioureido)benzene
    • DTXSID1024338
    • SPOT KLEEN
    • K4N81R84L8
    • NSC-170811
    • 1,2-Bis[3-(methoxycarbonyl)-2-thioureido]benzene
    • DTXCID104338
    • Allophanic acid, 4,4'-o-phenylenebis(3-thio-, dimethyl ester
    • CHEBI:35014
    • Dimethyl ((1,2-phenylene)bis-(iminocarbonothioyl))bis(carbamate)
    • Carbamic acid, (1,2-phenylenebis(iminocarbonothioyl))bis-, dimethyl ester
    • Carbamic acid, [1,2-phenylenebis(iminocarbonothioyl)]bis-, dimethyl ester
    • dimethyl 4,4'-(o-phenylene)bis(3-thioallophanate)
    • Allophanic acid, 4,4'-o-phenylenebis[3-thio-, dimethyl ester
    • RefChem:897871
    • methyl N-((2-((((methoxycarbonyl)amino)methanethioyl)amino)phenyl)carbamothioyl)carbamate
    • 245-740-7
    • Labilite
    • Ditek
    • methyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate
    • DIMETHYL 4,4-o-PHENYLENE-BIS (3-THIOPHANATE)
    • Pelt 44
    • MFCD00055294
    • Topsin-M
    • dimethyl (1,2-phenylenedicarbamothioyl)biscarbamate
    • Dimethyl (1,2-phenylenebis(iminocarbonothioyl))biscarbamate
    • Caswell No. 375A
    • Tiofanate metile [Italian]
    • NSC 170811
    • CAS-23564-05-8
    • CCRIS 6101
    • HSDB 6937
    • EINECS 245-740-7
    • Thiophanate-methyl [ANSI:BSI:ISO]
    • Thiophanate-methyl [ISO]
    • RCRA waste no. U409
    • EPA Pesticide Chemical Code 102001
    • BRN 0937942
    • dimethyl [1,2-phenylenebis(iminocarbonothioyl)]biscarbamate
    • Frumidor
    • UNII-K4N81R84L8
    • AI3-27905
    • Methyl thiophamate
    • NF-44
    • Labilite (Salt/Mix)
    • Spectrum_001761
    • SpecPlus_000748
    • Spectrum2_000646
    • Spectrum3_001211
    • Spectrum4_000096
    • Spectrum5_001330
    • SCHEMBL41622
    • BSPBio_002622
    • KBioGR_000392
    • KBioSS_002242
    • MLS002207244
    • BIDD:ER0424
    • DivK1c_006844
    • SPECTRUM1503974
    • Thiophanate-Methyl (Standard)
    • SPBio_000651
    • CHEMBL487187
    • orb1300324
    • SCHEMBL22261863
    • SCHEMBL29422247
    • HY-B0842R
    • KBio1_001788
    • KBio2_002241
    • KBio2_004809
    • KBio2_007377
    • KBio3_002122
    • THIOPHANATE-METHYL [HSDB]
    • Dimethyl ((1,2-phenylene)bis(iminocarbonothioyl))bis(carbamate)
    • HY-B0842
    • MSK20437
    • Tox21_201679
    • Tox21_300830
    • CCG-39648
    • 23564-05-8

  • Applications

    Thiophanate-Methyl (CAS 23564-05-8) is a systemic fungicide widely used in agriculture and horticulture to protect crops from a range of fungal diseases. It is commonly applied as a seed treatment, soil drench, or foliar spray to crops such as fruits, vegetables, and ornamentals, providing systemic protection against root and foliar pathogens; it is also used in turf management to suppress diseases in lawn grasses, and in greenhouse and nursery production to protect bedding and flowering crops. In some regions it is employed for post-harvest disease management on certain fruits and vegetables where permitted by regulation. Usage typically forms part of integrated disease management programs and is governed by label directions and local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.73
    methanol 1.09
    isopropanol 0.4
    water 0.01
    ethyl acetate 0.81
    n-propanol 0.53
    acetone 2.02
    n-butanol 0.37
    acetonitrile 0.74
    DMF 41.83
    toluene 0.03
    isobutanol 0.28
    1,4-dioxane 1.2
    methyl acetate 1.71
    THF 8.93
    2-butanone 2.85
    n-pentanol 0.26
    sec-butanol 0.53
    n-hexane 0.01
    ethylene glycol 0.46
    NMP 33.81
    cyclohexane 0.01
    DMSO 69.54
    n-butyl acetate 0.92
    n-octanol 0.23
    chloroform 1.75
    n-propyl acetate 0.77
    acetic acid 2.38
    dichloromethane 1.56
    cyclohexanone 2.26
    propylene glycol 0.91
    isopropyl acetate 0.43
    DMAc 79.87
    2-ethoxyethanol 3.55
    isopentanol 0.32
    n-heptane 0.01
    ethyl formate 1.58
    1,2-dichloroethane 0.78
    n-hexanol 0.19
    2-methoxyethanol 8.91
    isobutyl acetate 0.27
    tetrachloromethane 0.1
    n-pentyl acetate 0.54
    transcutol 6.0
    n-heptanol 0.24
    ethylbenzene 0.05
    MIBK 0.48
    2-propoxyethanol 3.98
    tert-butanol 0.44
    MTBE 0.34
    2-butoxyethanol 2.22
    propionic acid 1.33
    o-xylene 0.05
    formic acid 3.42
    diethyl ether 0.24
    m-xylene 0.03
    p-xylene 0.08
    chlorobenzene 0.11
    dimethyl carbonate 2.07
    n-octane 0.01
    formamide 8.45
    cyclopentanone 7.46
    2-pentanone 0.98
    anisole 0.52
    cyclopentyl methyl ether 0.54
    gamma-butyrolactone 9.42
    1-methoxy-2-propanol 5.47
    pyridine 1.82
    3-pentanone 0.96
    furfural 9.54
    n-dodecane 0.01
    diethylene glycol 3.8
    diisopropyl ether 0.04
    tert-amyl alcohol 0.65
    acetylacetone 1.85
    n-hexadecane 0.01
    acetophenone 1.18
    methyl propionate 1.87
    isopentyl acetate 0.8
    trichloroethylene 2.63
    n-nonanol 0.27
    cyclohexanol 0.24
    benzyl alcohol 0.66
    2-ethylhexanol 0.17
    isooctanol 0.2
    dipropyl ether 0.3
    1,2-dichlorobenzene 0.22
    ethyl lactate 1.63
    propylene carbonate 3.53
    n-methylformamide 8.14
    2-pentanol 0.19
    n-pentane 0.0
    1-propoxy-2-propanol 2.67
    1-methoxy-2-propyl acetate 2.27
    2-(2-methoxypropoxy) propanol 4.51
    mesitylene 0.02
    ε-caprolactone 2.63
    p-cymene 0.07
    epichlorohydrin 8.1
    1,1,1-trichloroethane 0.41
    2-aminoethanol 1.03
    morpholine-4-carbaldehyde 15.85
    sulfolane 27.4
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 1.59
    n-hexyl acetate 0.69
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 3.43
    sec-butyl acetate 0.36
    tert-butyl acetate 0.56
    decalin 0.01
    glycerin 3.37
    diglyme 8.91
    acrylic acid 1.96
    isopropyl myristate 0.31
    n-butyric acid 1.33
    acetyl acetate 0.56
    di(2-ethylhexyl) phthalate 0.8
    ethyl propionate 0.94
    nitromethane 10.39
    1,2-diethoxyethane 0.89
    benzonitrile 0.55
    trioctyl phosphate 0.48
    1-bromopropane 0.25
    gamma-valerolactone 12.09
    n-decanol 0.2
    triethyl phosphate 1.28
    4-methyl-2-pentanol 0.11
    propionitrile 0.64
    vinylene carbonate 2.84
    1,1,2-trichlorotrifluoroethane 11.83
    DMS 1.36
    cumene 0.04
    2-octanol 0.15
    2-hexanone 0.96
    octyl acetate 0.47
    limonene 0.1
    1,2-dimethoxyethane 8.87
    ethyl orthosilicate 0.93
    tributyl phosphate 0.74
    diacetone alcohol 2.09
    N,N-dimethylaniline 0.57
    acrylonitrile 1.51
    aniline 0.31
    1,3-propanediol 1.42
    bromobenzene 0.08
    dibromomethane 0.63
    1,1,2,2-tetrachloroethane 2.61
    2-methyl-cyclohexyl acetate 0.83
    tetrabutyl urea 1.45
    diisobutyl methanol 0.11
    2-phenylethanol 0.61
    styrene 0.06
    dioctyl adipate 0.96
    dimethyl sulfate 9.83
    ethyl butyrate 0.98
    methyl lactate 3.98
    butyl lactate 1.4
    diethyl carbonate 0.95
    propanediol butyl ether 1.87
    triethyl orthoformate 1.12
    p-tert-butyltoluene 0.06
    methyl 4-tert-butylbenzoate 2.19
    morpholine 3.27
    tert-butylamine 0.13
    n-dodecanol 0.14
    dimethoxymethane 7.33
    ethylene carbonate 1.7
    cyrene 5.51
    2-ethoxyethyl acetate 1.24
    2-ethylhexyl acetate 0.56
    1,2,4-trichlorobenzene 0.46
    4-methylpyridine 1.01
    dibutyl ether 0.28
    2,6-dimethyl-4-heptanol 0.11
    DEF 4.46
    dimethyl isosorbide 7.17
    tetrachloroethylene 1.1
    eugenol 2.66
    triacetin 1.8
    span 80 1.91
    1,4-butanediol 0.48
    1,1-dichloroethane 0.42
    2-methyl-1-pentanol 0.29
    methyl formate 5.04
    2-methyl-1-butanol 0.4
    n-decane 0.01
    butyronitrile 0.55
    3,7-dimethyl-1-octanol 0.22
    1-chlorooctane 0.07
    1-chlorotetradecane 0.03
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.01
    cyclooctane 0.0
    cyclopentanol 0.59
    tetrahydropyran 0.53
    tert-amyl methyl ether 0.45
    2,5,8-trioxanonane 6.62
    1-hexene 0.05
    2-isopropoxyethanol 1.55
    2,2,2-trifluoroethanol 2.02
    methyl butyrate 1.72

    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