Azinphos-methyl

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  • Identifiers

    CAS number
    86-50-0

    Molecular formula
    C10H12N3O3PS2

    SMILES
    COP(=S)(OC)SCN1C(=O)C2=CC=CC=C2N=N1

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 41.83%
    Sulfurous 41.48%
    Roasted 39.83%
    Meaty 37.41%
    Cooked 32.79%
    Savory 32.74%
    Onion 22.79%
    Grape 20.56%
    Burnt 20.48%
    Cheesy 19.95%

     

    Flavor
    Bitter 59.06%
    Roasted 28.06%
    Odorless 26.11%
    Cooked 24.85%
    Bland 21.95%
    Taco 21.66%
    Scallion 21.64%
    Roasted peanuts 20.84%
    Mild 20.43%
    Bread crust 20.21%

     

    Odor impact est.
    Low

    Odor threshold

    • Detection: 0.0002 mg/kg water

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    4.33 (weak acid)

    Molecular weight
    317.3 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra fast

    Melting point expt.

    • 163 to 165 °F (EPA, 1998)
    • 73-74 °C
    • Cream to yellow-brown granular solid, MP: 67-70 °C /Technical/
    • 163 °F

    Boiling point

    • Decomposes (NTP, 1992)
    • Decomposes

    Flash point

    • 212.96 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 66 °F (NTP, 1992)
    • Soluble in methanol, ethanol, and propylene glycol, xylene, other organic solvents.
    • In dichloroethane, acetone, acetonitrile, ethyl acetate, and dimethyl sulfoxide, the solubility is >250 g/L at 20 °C; n-heptane, 1.2 g/L at 20 °C; xylene, 170 g/L at 20 °C
    • In toluene, dichloromethane, >20 g/L
    • Readily soluble in most organic solvents (toluene, chloroform, acetonitrile, benzene, carbon tetrachloride, and chlorobenzene), slightly soluble in 1-propanol.
    • In water, 20.9 mg/L at 20 °C
    • Solubility in water: none
    • 0.003%

  • Synonyms

    • Azinphos-methyl
    • Azinphosmethyl
    • azinphos methyl
    • 86-50-0
    • Guthion
    • Azinphos
    • Methylazinphos
    • Methylgusathion
    • Metiltriazotion
    • Crysthyon
    • Carfene
    • Cotneon
    • Cotnion
    • Cotnion methyl
    • Gusathion M
    • Gusathion Methyl
    • Crysthion 2L
    • Gusathion 25
    • Gusathion-20
    • Azinphos-metile
    • METHYL GUTHION
    • Azinfos-Methyl
    • Bayer 9027
    • Bayer 17147
    • NCI-C00066
    • BAY 9027
    • BAY 17147
    • ENT 23,233
    • 3-(dimethoxyphosphinothioylsulfanylmethyl)-1,2,3-benzotriazin-4-one
    • O,O-Dimethyl S-(3,4-dihydro-4-keto-1,2,3-benzotriazinyl-3-methyl) dithiophosphate
    • Phosphorodithioic acid, O,O-dimethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) ester
    • R 1582
    • Benzotriazinedithiophosphoric acid dimethoxy ester
    • Phosphorodithioic acid, O,O-dimethyl ester, S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one
    • O,O-Dimethyl-S-(benzaziminomethyl) dithiophosphate
    • Dimethyldithiophosphoric acid N-methylbenzazimide ester
    • N-Methylbenzazimide, dimethyldithiophosphoric acid ester
    • CHEBI:2953
    • DTXSID3020122
    • O,O-Dimethyl S-(4-oxobenzotriazino-3-methyl)phosphorodithioate
    • 265842EWUV
    • O,O-Dimethyl S-(4-oxo-1,2,3-benzotriazino(3)-methyl) thiothionophosphate
    • O,O-Dimethyl S-(4-oxo-3H-1,2,3-benzotriazine-3-methyl)phosphorodithioate
    • O,O-Dimethyl-S-(1,2,3-benzotriazinyl-4-keto)methyl phosphorodithioate
    • o,o-Dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] dithiophosphate
    • O,O-Dimethyl S-4-oxo-1,2,3-benzotriazin-3(4H)-ylmethyl phosphorodithioate
    • 1,2,3-Benzotriazin-4(3H)-one, 3-(mercaptomethyl)-, O,O-dimethyl phosphorodithioate
    • 3-(Mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one O,O-dimethyl phosphorodithioate S-ester
    • Metazintox
    • O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat
    • O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithioate
    • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiofosfaat
    • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiophosphat
    • O,O-Dimetil-S-((4-oxo-3H-1,2,3-benzotriazin-3-il)-metil)-ditiofosfato
    • Phosphorodithioic acid, O,O-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] ester
    • Phosphorodithioic acid, O,O-dimethylS-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] ester
    • DTXCID10122
    • Caswell No. 374
    • Methyltriazotin
    • Gothnion
    • Azinfos-methyl [Dutch]
    • Azinophos-methyl
    • Methyl gusathion
    • Azinphos-metile [Italian]
    • 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one, O,O-dimethyl phosphorodithioate
    • CAS-86-50-0
    • CCRIS 63
    • Azinphos-methyl [BSI:ISO]
    • EPA Shaughnessy #058001
    • HSDB 1171
    • Azinphos-methyl [ISO]
    • EINECS 201-676-1
    • EPA Pesticide Chemical Code 058001
    • BRN 0280476
    • Azinugec
    • UNII-265842EWUV
    • AI3-23233
    • O,O-DIMETHYL S-((4-OXO-1,2,3-BENZOTRIAZIN-3(4H)-YL)METHYL) PHOSPHORODITHIOATE
    • Benzotriazine derivative of a methyl dithiophosphate
    • Spectrum_001769
    • SpecPlus_000352
    • 3-Dimethoxyphosphinothioylthiomethyl-1,2,3-benzotriazin-4(3H)-one
    • Spectrum2_001846
    • Spectrum3_000806
    • Spectrum4_000646
    • Spectrum5_001925
    • O,O-Dimethyl-S-(4-oxobenzotriazin-3-methyl)-dithiophosphat [German]
    • O,O-Dimethyl S-(4-oxo-1,2,3-benzotriazino(3)-methyl)thiothionophosphate
    • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiofosfaat [Dutch]
    • O,O-Dimethyl-S-((4-oxo-3H-1,2,3-benzotriazin-3-yl)-methyl)-dithiophosphat [German]
    • O,O-Dimetil-S-((4-oxo-3H-1,2,3-benzotriazin-3-il)-metil)-ditiofosfato [Italian]
    • S-(3,4-Dihydro-4-oxo-benzo(alpha)(1,2,3)triazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
    • S-3,4-Dihydro-4-oxobenzo(d)(1,2,3)triazin-3-ylmethyl O,O-dimethyl phosphorodithioate
    • SCHEMBL27791
    • AZINPHOS-METHYL [MI]
    • BSPBio_002271
    • KBioGR_000991
    • KBioSS_002250
    • SPECTRUM330013
    • MLS002695975
    • DivK1c_006448
    • SPBio_001632
    • AZINPHOS-METHYL [HSDB]
    • CHEMBL530115
    • CJJOSEISRRTUQB-UHFFFAOYSA-
    • KBio1_001392
    • KBio2_002249
    • KBio2_004817
    • KBio2_007385
    • KBio3_001771
    • HMS3089C06
    • EX-A2861
    • Tox21_201965
    • Tox21_300929
    • CCG-39384
    • AKOS015902796
    • O,O-Dimethyl phosphorodithioate S-ester with 3-(mercaptomethyl)-1,2,3-benzotriazin-4(3H)-one
    • S-(3,4-Dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl) O,O-dimethyl phosphorodithioate
    • NCGC00091883-01
    • NCGC00091883-02
    • NCGC00091883-03
    • NCGC00091883-04
    • NCGC00091883-05
    • NCGC00091883-06
    • NCGC00091883-07
    • NCGC00091883-08
    • NCGC00178729-01
    • NCGC00254831-01

  • Applications

    Azinphos-methyl is primarily used as an organophosphate insecticide in agriculture. It is applied as foliar sprays or soil treatments to control a range of chewing and sucking pests on fruit and nut crops (such as apples, pears, peaches, almonds, and walnuts) and on certain vegetables, and formulations commonly include emulsifiable concentrates or wettable powders used within integrated pest management programs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.15
    methanol 1.85
    isopropanol 0.64
    water 0.03
    ethyl acetate 4.2
    n-propanol 1.0
    acetone 4.86
    n-butanol 0.73
    acetonitrile 3.66
    DMF 49.59
    toluene 0.46
    isobutanol 0.65
    1,4-dioxane 6.87
    methyl acetate 6.45
    THF 13.83
    2-butanone 6.28
    n-pentanol 0.65
    sec-butanol 0.89
    n-hexane 0.02
    ethylene glycol 1.66
    NMP 64.78
    cyclohexane 0.07
    DMSO 35.16
    n-butyl acetate 3.0
    n-octanol 0.31
    chloroform 6.47
    n-propyl acetate 2.83
    acetic acid 8.39
    dichloromethane 9.36
    cyclohexanone 9.3
    propylene glycol 1.15
    isopropyl acetate 2.62
    DMAc 50.38
    2-ethoxyethanol 7.01
    isopentanol 0.7
    n-heptane 0.07
    ethyl formate 4.65
    1,2-dichloroethane 5.56
    n-hexanol 0.69
    2-methoxyethanol 12.14
    isobutyl acetate 1.25
    tetrachloromethane 0.45
    n-pentyl acetate 2.28
    transcutol 17.22
    n-heptanol 0.64
    ethylbenzene 0.29
    MIBK 2.02
    2-propoxyethanol 6.93
    tert-butanol 0.9
    MTBE 1.03
    2-butoxyethanol 3.95
    propionic acid 3.81
    o-xylene 0.61
    formic acid 9.33
    diethyl ether 1.42
    m-xylene 0.39
    p-xylene 0.43
    chlorobenzene 1.55
    dimethyl carbonate 6.79
    n-octane 0.03
    formamide 22.46
    cyclopentanone 17.26
    2-pentanone 3.56
    anisole 2.59
    cyclopentyl methyl ether 3.24
    gamma-butyrolactone 28.29
    1-methoxy-2-propanol 6.53
    pyridine 7.23
    3-pentanone 3.76
    furfural 37.13
    n-dodecane 0.03
    diethylene glycol 8.77
    diisopropyl ether 0.38
    tert-amyl alcohol 1.19
    acetylacetone 9.7
    n-hexadecane 0.03
    acetophenone 5.37
    methyl propionate 5.76
    isopentyl acetate 2.59
    trichloroethylene 16.2
    n-nonanol 0.41
    cyclohexanol 1.03
    benzyl alcohol 2.57
    2-ethylhexanol 0.67
    isooctanol 0.57
    dipropyl ether 1.43
    1,2-dichlorobenzene 2.77
    ethyl lactate 3.85
    propylene carbonate 12.02
    n-methylformamide 15.99
    2-pentanol 0.51
    n-pentane 0.03
    1-propoxy-2-propanol 4.71
    1-methoxy-2-propyl acetate 7.96
    2-(2-methoxypropoxy) propanol 6.55
    mesitylene 0.3
    ε-caprolactone 9.79
    p-cymene 0.65
    epichlorohydrin 26.47
    1,1,1-trichloroethane 2.35
    2-aminoethanol 2.15
    morpholine-4-carbaldehyde 49.47
    sulfolane 46.27
    2,2,4-trimethylpentane 0.04
    2-methyltetrahydrofuran 5.99
    n-hexyl acetate 1.68
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 6.13
    sec-butyl acetate 1.69
    tert-butyl acetate 3.14
    decalin 0.05
    glycerin 4.97
    diglyme 19.41
    acrylic acid 6.87
    isopropyl myristate 0.85
    n-butyric acid 3.37
    acetyl acetate 4.37
    di(2-ethylhexyl) phthalate 1.91
    ethyl propionate 2.98
    nitromethane 36.61
    1,2-diethoxyethane 4.3
    benzonitrile 3.58
    trioctyl phosphate 0.98
    1-bromopropane 1.13
    gamma-valerolactone 37.46
    n-decanol 0.33
    triethyl phosphate 3.4
    4-methyl-2-pentanol 0.4
    propionitrile 2.58
    vinylene carbonate 11.93
    1,1,2-trichlorotrifluoroethane 25.35
    DMS 5.36
    cumene 0.3
    2-octanol 0.37
    2-hexanone 2.52
    octyl acetate 1.16
    limonene 0.88
    1,2-dimethoxyethane 14.31
    ethyl orthosilicate 2.69
    tributyl phosphate 1.39
    diacetone alcohol 5.48
    N,N-dimethylaniline 2.37
    acrylonitrile 6.24
    aniline 1.86
    1,3-propanediol 2.41
    bromobenzene 1.25
    dibromomethane 3.17
    1,1,2,2-tetrachloroethane 10.47
    2-methyl-cyclohexyl acetate 3.37
    tetrabutyl urea 2.5
    diisobutyl methanol 0.57
    2-phenylethanol 2.72
    styrene 0.4
    dioctyl adipate 2.25
    dimethyl sulfate 22.81
    ethyl butyrate 3.72
    methyl lactate 7.49
    butyl lactate 3.0
    diethyl carbonate 3.64
    propanediol butyl ether 2.49
    triethyl orthoformate 3.77
    p-tert-butyltoluene 0.62
    methyl 4-tert-butylbenzoate 5.56
    morpholine 9.87
    tert-butylamine 0.37
    n-dodecanol 0.27
    dimethoxymethane 14.08
    ethylene carbonate 7.46
    cyrene 14.28
    2-ethoxyethyl acetate 6.48
    2-ethylhexyl acetate 1.98
    1,2,4-trichlorobenzene 4.83
    4-methylpyridine 5.14
    dibutyl ether 0.64
    2,6-dimethyl-4-heptanol 0.57
    DEF 10.01
    dimethyl isosorbide 19.54
    tetrachloroethylene 5.47
    eugenol 6.61
    triacetin 6.19
    span 80 3.83
    1,4-butanediol 1.14
    1,1-dichloroethane 2.18
    2-methyl-1-pentanol 0.72
    methyl formate 13.95
    2-methyl-1-butanol 0.75
    n-decane 0.04
    butyronitrile 1.75
    3,7-dimethyl-1-octanol 0.48
    1-chlorooctane 0.22
    1-chlorotetradecane 0.12
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.04
    cyclooctane 0.03
    cyclopentanol 1.78
    tetrahydropyran 2.65
    tert-amyl methyl ether 1.35
    2,5,8-trioxanonane 14.14
    1-hexene 0.13
    2-isopropoxyethanol 3.77
    2,2,2-trifluoroethanol 8.37
    methyl butyrate 4.14

    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