ChemSpider 2D Image | Captafol | C10H9Cl4NO2S

Captafol

  • Molecular FormulaC10H9Cl4NO2S
  • Average mass349.061 Da
  • Monoisotopic mass346.910797 Da
  • ChemSpider ID16139

More details:

Featured data source
The Merck Index Online

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

1H-Isoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-[(1,1,2,2-tetrachloroethyl)thio]- [ACD/Index Name]
2-[(1,1,2,2-Tetrachlorethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindol-1,3(2H)-dion [German] [ACD/IUPAC Name]
2-[(1,1,2,2-Tetrachloroethyl)sulfanyl]-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione [ACD/IUPAC Name]
2-[(1,1,2,2-Tétrachloroéthyl)sulfanyl]-3a,4,7,7a-tétrahydro-1H-isoindole-1,3(2H)-dione [French] [ACD/IUPAC Name]
219-363-3 [EINECS]
2425-06-1 [RN]
3a,4,7,7a-Tetrahydro-2-((1,1,2,2-tetrachloroethyl)thio)-1H-isoindole-1,3(2H)-dione (9CI)
Captafol [BSI] [ISO]
GW4900000
MFCD00041816
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

24206-1 [DBID]
45365_RIEDEL [DBID]
BRN 1543712 [DBID]
Caswell No. 828 [DBID]
CCRIS 848 [DBID]
CS 5623 [DBID]
EPA Pesticide Chemical Code 081701 [DBID]
HSDB 340 [DBID]
Nalco 7046 [DBID]
Ortho 5865 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      White, crystalline solid with a slight, characteristic pungent odor. [fungicide] [Note: Available commercially as a wettable powder or in liquid form.] NIOSH GW4900000

    • Toxicity:

      Organic Compound; Organochloride; Pesticide; Amide; Food Toxin; Metabolite; Synthetic Compound; Fungicide Toxin, Toxin-Target Database T3D4482

    • First-Aid:

      Eye: Irrigate immediately Skin: Soap wash immediately Breathing: Respiratory support Swallow: Medical attention immediately NIOSH GW4900000

    • Exposure Routes:

      inhalation, skin absorption, ingestion, skin and/or eye contact NIOSH GW4900000

    • Symptoms:

      Irritation eyes, skin, respiratory system; dermatitis, skin sensitization; conjunctivitis; bronchitis, wheezing; diarrhea, vomiting; liver, kidney injury; high blood pressure; in animals: teratogenic effects; [potential occupational carcinogen] NIOSH GW4900000

    • Target Organs:

      Eyes, skin, respiratory system, central nervous system, liver, kidneys, cardiovascular system Cancer Site [in animals: tumors at many sites] NIOSH GW4900000

    • Incompatibility:

      Acids, acid vapors, strong oxidizers NIOSH GW4900000

    • Personal Protection:

      Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated/Daily Remove: When wet or contaminated Change: Daily Provide: Eyewash, Quick drench NIOSH GW4900000

    • Exposure Limits:

      NIOSH REL : Ca TWA 0.1 mg/m 3 [skin] See Appendix A OSHA PEL ?: none NIOSH GW4900000

    • Chemical Class:

      A dicarboximide that captan in which the trichloromethyl group is replaced by a 1,1,2,2-tetrachloroethyl group. A broad-spectrum fungicide used to control diseases in fruit and potatoes, it is no long er approved for use in the European Community. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:81938, CHEBI:81938
  • Gas Chromatography

    • Retention Index (Kovats):

      2381 (estimated with error: 89) NIST Spectra mainlib_60508, mainlib_125551, replib_59594, replib_60155, replib_318571

    • Retention Index (Normal Alkane):

      2337.9 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 50C(1min) =>20C/min =>120C => 5C/min => 300C(10min); CAS no: 2425061; Active phase: DB-1; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Shimadzu Corporation, Analysis of 124 pesticides with capillary GC-FTD and GC-ECD, 2003.) NIST Spectra nist ri
      2341.3 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 2 m; Column type: Packed; CAS no: 2425061; Active phase: OV-101; Carrier gas: N2; Substrate: GAs Chrom Q (80-100 mesh); Data type: Normal alkane RI; Authors: Omura, M.; Hashimoto, K.; Ohta, K.; Iio, T.; Ueda, S.; Ando, K.; Fujiu, Y.; Hiraide, H., Effective application of the relative retention time diagram for gas chromatographic analysis of pesticides, J. Agric. Food Chem., 39(12), 1991, 2200-2205.) NIST Spectra nist ri
      2323 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.2 mm; Column length: 25 m; Column type: Capillary; Description: 80 0C (0.5 min) ^ 25 0C/min -> 185 0C ^ 5 0C/min -> 225 0C (3 min); CAS no: 2425061; Active phase: Methyl Silicone; Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Szeto, S.Y.; Price, P.M., Persistence of pesticide residues in mineral and organic soils in the Fraser Valley of British Columbia, J. Agric. Food Chem., 39(9), 1991, 1679-1684.) NIST Spectra nist ri
      2337.4 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 2.4 m; Column type: Packed; Heat rate: 10 K/min; Start T: 150 C; End T: 300 C; CAS no: 2425061; Active phase: OV-101; Substrate: Gas Chrom Q; Data type: Normal alkane RI; Authors: Bowman, M.C.; Beroza, M., GLC Retention Times of Pesticides and Metabolites Containing Phosphorus and Sulfur on Four Thermally Stable Columns, J. Ass. Offic. Anal. Chem, 53(3), 1970, 499-508.) NIST Spectra nist ri
      2386.1 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 70C(2min) =>25C/min =>150C=>3C/min => 200C=> 8C/min =>280C(10min); CAS no: 2425061; Active phase: HP-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Wong, J.W.; Webster, M.G.; Bezabeh, D.Z.; Hengel, M.J.; Ngim, K.K.; Krynitsky, A.J.; Ebeler, S.E., Multiresidue determination of pesticides in malt beverages by capillary gas chromatography with mass spectrometry and selected ion monitoring, J. Agric. Food Chem., 52, 2004, 6361-6372.) NIST Spectra nist ri
      2384.7 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 50C(1min) =>20C/min =>120C => 5C/min => 300C(10min); CAS no: 2425061; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Shimadzu Corporation, Analysis of 124 pesticides with capillary GC-FTD and GC-ECD, 2003.) NIST Spectra nist ri
      2383.7 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 50 C (1.13 min) ^ 30 C/min -> 150 C ^ 3 C/min -> 205 C ^ 10 C/min -> 250 C (20 min); CAS no: 2425061; Active phase: HP-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Cook, J.; Engel, M.; Wylie, P.; Quimby, B., Multiresidue screening of pesticides in foods using retention time locking, GC-AED, database search, and GC/MS identification, J. AOAC Int., 82(2), 1999, 313-326.) NIST Spectra nist ri
      2355.9 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Heat rate: 6 K/min; Start T: 60 C; End T: 260 C; End time: 12 min; CAS no: 2425061; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Mogadati, P.; Louis, J.B.; Rosen, J.D., Multiresidue determination of pesticides in high-organic-content soils by solid-phase extraction and gas chromatography/mass spectrometry, J. AOAC Int., 82(3), 1999, 705-715.) NIST Spectra nist ri
      2382.3 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Heat rate: 4 K/min; Start T: 100 C; End T: 275 C; End time: 2 min; Start time: 5 min; CAS no: 2425061; Active phase: RTX-5; Carrier gas: He; Phase thickness: 0.5 um; Data type: Normal alkane RI; Authors: Restek, Restek International, 1999 Product Guide, 1(1), 1999, 578-591, In original 578-591.) NIST Spectra nist ri
      2381.4 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 15 m; Column type: Capillary; Description: 190 0C (14 min) ^ 20 0C/min -> 230 0C (7 min) ^ 20 0C/min -> 250 0C (5 min); CAS no: 2425061; Active phase: SPB-5; Carrier gas: He; Phase thickness: 1.5 um; Data type: Normal alkane RI; Authors: Sannino, A.; Bandini, M.; Bolzoni, L., Multiresidue determination of 19 fungicides in processed fruits and vegetables by capillary gas chromatography after gel permeation chromatography, J. AOAC Int., 82(5), 1999, 1229-1238.) NIST Spectra nist ri
      2380 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.2 mm; Column length: 25 m; Column type: Capillary; Description: 85 0C (1 min) ^ 40 0C/min -> 150 0C (2 min) ^ 10 0C/min -> 280 0C (20 min); CAS no: 2425061; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Holland, P.T.; McNaughton, D.E.; Malcolm, C.P., Multiresidue analysis of pesticides in wines by solid-phase extraction, J. AOAC Int., 77(1), 1994, 79-86.) NIST Spectra nist ri
      2372.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 57 0C (1 min) ^ 15 0C/min -> 130 0C (1 min) ^ 2.3 0C/min -> 270 0C (20 min); CAS no: 2425061; Active phase: DB-5; Data type: Normal alkane RI; Authors: Bernal, J.L.; del Nozal, M.J.; Atienza, J.; Jimenez, J.J., Multidetermination of PCBs and pesticides by use of a dual GC column-dual detector system, Chromatographia, 33(1/2), 1992, 67-76.) NIST Spectra nist ri
      2367.3 (Program type: Ramp; Column cl... (show more) ass: Semi-standard non-polar; Column diameter: 0.53 mm; Column length: 30 m; Column type: Capillary; Heat rate: 2.8 K/min; Start T: 140 C; End T: 270 C; End time: 1 min; Start time: 2 min; CAS no: 2425061; Active phase: DB-5; Carrier gas: He; Phase thickness: 1.5 um; Data type: Normal alkane RI; Authors: Lopez-Avila, V.; Benedicto, J.; Baldin, E.; Beckert, W.F., Analysis of classes of compounds of environmental concern: III. Organochlorine pesticides, J. Hi. Res. Chromatogr., 15, 1992, 319-328.) NIST Spectra nist ri

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.6±0.1 g/cm3
Boiling Point: 365.7±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 61.2±3.0 kJ/mol
Flash Point: 175.0±30.7 °C
Index of Refraction: 1.629
Molar Refractivity: 75.6±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 3
#Rule of 5 Violations: 0
ACD/LogP: 2.40
ACD/LogD (pH 5.5): 3.12
ACD/BCF (pH 5.5): 138.79
ACD/KOC (pH 5.5): 1188.77
ACD/LogD (pH 7.4): 3.12
ACD/BCF (pH 7.4): 138.79
ACD/KOC (pH 7.4): 1188.77
Polar Surface Area: 63 Å2
Polarizability: 30.0±0.5 10-24cm3
Surface Tension: 60.8±5.0 dyne/cm
Molar Volume: 212.8±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.42
    Log Kow (Exper. database match) =  3.80
       Exper. Ref:  Tomlin,C (1997)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  473.28  (Adapted Stein & Brown method)
    Melting Pt (deg C):  200.12  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  5.33E-009  (Modified Grain method)
    MP  (exp database):  160-161 deg C
    VP  (exp database):  1.50E-08 mm Hg at 0 deg C
    Subcooled liquid VP: 1.29E-007 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  3.569
       log Kow used: 3.80 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1.4 mg/L (22 deg C)
        Exper. Ref:  WORTHING,CR & WALKER,SB (1987)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  124.26 mg/L
    Wat Sol (Exper. database match) =  1.40
       Exper. Ref:  WORTHING,CR & WALKER,SB (1987)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Imides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.15E-009  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  6.859E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.80  (exp database)
  Log Kaw used:  -7.056  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.856
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.0481
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.5230  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.7882  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.2283
   Biowin6 (MITI Non-Linear Model):   0.0001
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.0308
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  1.72E-005 Pa (1.29E-007 mm Hg)
  Log Koa (Koawin est  ): 10.856
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.174 
       Octanol/air (Koa) model:  0.0176 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.863 
       Mackay model           :  0.933 
       Octanol/air (Koa) model:  0.585 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  87.6892 E-12 cm3/molecule-sec
      Half-Life =     0.122 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.464 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    20.000000 E-17 cm3/molecule-sec
      Half-Life =     0.057 Days (at 7E11 mol/cm3)
      Half-Life =      1.375 Hrs
   Fraction sorbed to airborne particulates (phi): 0.898 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2736
      Log Koc:  3.437 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.226 (BCF = 168.3)
       log Kow used: 3.80 (expkow database)

 Volatilization from Water:
    Henry LC:  2.15E-009 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 5.088E+005  hours   (2.12E+004 days)
    Half-Life from Model Lake :  5.55E+006  hours   (2.313E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              21.84  percent
    Total biodegradation:        0.25  percent
    Total sludge adsorption:    21.58  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00593         0.936        1000       
   Water     5.8             4.32e+003    1000       
   Soil      92.7            8.64e+003    1000       
   Sediment  1.45            3.89e+004    0          
     Persistence Time: 5.35e+003 hr

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