ChemSpider 2D Image | Dicrotophos | C8H16NO5P

Dicrotophos

  • Molecular FormulaC8H16NO5P
  • Average mass237.190 Da
  • Monoisotopic mass237.076614 Da
  • ChemSpider ID4522051

  • Double-bond stereo - Double-bond stereo

More details:

Featured data source
The Merck Index Online

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

(2E)-4-(Dimethylamino)-4-oxo-2-buten-2-yl dimethyl phosphate [ACD/IUPAC Name]
(2E)-4-(Dimethylamino)-4-oxo-2-buten-2-yl-dimethylphosphat [German] [ACD/IUPAC Name]
(2E)-4-(Dimethylamino)-4-oxobut-2-en-2-yl dimethyl phosphate
(2E)-4-(Dimethylamino)-4-oxobut-2-en-2-yl-dimethylphosphat
(E)-3-(Dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl phosphate (9CI)
141-66-2 [RN]
1880084 [Beilstein]
205-494-3 [EINECS]
B541I65WBL
Bidirl
More...

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

ENT 24482 [DBID]
45305_RIEDEL [DBID]
AI3-24482 [DBID]
BRN 1880084 [DBID]
C 709 [DBID]
Caswell No. 376 [DBID]
Ciba 709 [DBID]
ENT 24,482 [DBID]
EPA Pesticide Chemical Code 035201 [DBID]
HSDB 1637 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Appearance:

      Yellow-brown liquid with a mild, ester odor. [insecticide] NIOSH TC3850000

    • Toxicity:

      Organic Compound; Pesticide; Amine; Organophosphate; Amide; Ester; Insecticide; Synthetic Compound Toxin, Toxin-Target Database T3D3826

    • First-Aid:

      Eye: Irrigate immediately Skin: Water wash immediately Breathing: Respiratory support Swallow: Medical attention immediately NIOSH TC3850000

    • Exposure Routes:

      inhalation, skin absorption, ingestion, skin and/or eye contact NIOSH TC3850000

    • Symptoms:

      Headache, nausea, dizziness, anxiety, restlessness, muscle twitching, lassitude (weakness, exhaustion), tremor, incoordination, vomiting, abdominal cramps, diarrhea; salivation, sweating, lacrimation (discharge of tears), rhinitis; anorexia, malaise (vague feeling of discomfort) NIOSH TC3850000

    • Target Organs:

      central nervous system, blood cholinesterase NIOSH TC3850000

    • Incompatibility:

      Metals [Note: Corrosive to cast iron, mild steel, brass & stainless steel.] NIOSH TC3850000

    • Personal Protection:

      Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated Remove: When wet or contaminated Change: Daily Provide: Quick drench NIOSH TC3850000

    • Exposure Limits:

      NIOSH REL : TWA 0.25 mg/m 3 [skin] OSHA PEL ?: none NIOSH TC3850000
  • Gas Chromatography

    • Retention Index (Normal Alkane):

      1645.4 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column diameter: 0.2 mm; Column length: 12 m; Column type: Capillary; Heat rate: 18 K/min; Start T: 60 C; End T: 265 C; Start time: 1 min; CAS no: 141662; Active phase: HP-1; Carrier gas: He; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Liao, W.; Joe, T.; Cusick, W.G., Multiresidue screening method for fresh fruits and vegetables with gas chromatographic/mass spectrometric detection, J. Ass. Offic. Anal. Chem, 74(3), 1991, 554-565.) NIST Spectra nist ri
      1674.4 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column length: 1.1 m; Column type: Packed; Heat rate: 8.5 K/min; Start T: 50 C; End T: 300 C; CAS no: 141662; Active phase: OV-101; Carrier gas: N2; Substrate: Chromosorb W HP; Data type: Normal alkane RI; Authors: Saxton, W.L., Emergence temperature indices and relative retention times of pesticides and industrial chemicals determined by linear programmed temperature gas chromatography, J. Chromatogr., 393, 1987, 175-194.) NIST Spectra nist ri
      1639.8 (Program type: Ramp; Column cl... (show more) ass: Standard non-polar; Column type: Packed; Heat rate: 4 K/min; Start T: 200 C; End T: 290 C; CAS no: 141662; Active phase: SE-30; Data type: Normal alkane RI; Authors: Krijgsman, W.; van de Kamp, C.G., Analysis of organophosphorus pesticides by capillary gas chromatography with flame photometric detection, J. Chromatogr., 117, 1976, 201-205.) NIST Spectra nist ri
      1665.9 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 6 ft; Column type: Packed; CAS no: 141662; Active phase: DC-200; Carrier gas: He; Substrate: Chromosorb W HP (80-100 mesh); Data type: Normal alkane RI; Authors: Laski, R.R.; Watts, R.R., Gas chromatography of organonitrogen pesticides, using a nitrogen-specific detection system, J. Ass. Offic. Anal. Chem, 55(2), 1973, 328-332.) NIST Spectra nist ri
      1640.8 (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: 141662; 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
      1645.3 (Program type: Isothermal; Col... (show more) umn class: Standard non-polar; Column length: 3 ft; Column type: Packed; CAS no: 141662; Active phase: DC-200; Carrier gas: N2; Substrate: Gas Chrom Q; Data type: Normal alkane RI; Authors: Watts, R.R.; Storherr, R.W., Gas chromatography of organophosphorus pesticides: Retention times and response data on three columns, J. Ass. Offic. Anal. Chem, 52(3), 1969, 513-521.) NIST Spectra nist ri
      1639.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.2 mm; Column length: 25 m; Column type: Capillary; Description: 100C(1min) => 30C/min=> 150C(2min) => 3C/min=> 205C => 10C/min =>260C(29min); CAS no: 141662; Active phase: SE-54; Phase thickness: 0.33 um; Data type: Normal alkane RI; Authors: Stan, H.-J., Pesticide residue analysis in foodstuffs applying capillary gas chromatography with mass spectrometric detection State-of-the-art use of modified DFG-multimethod S19 and automated data evaluation, J. Chromatogr. A, 892, 2000, 347-377.) NIST Spectra nist ri
      1673.9 (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: 125 C; End T: 250 C; End time: 10 min; Start time: 10 min; CAS no: 141662; 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
      1661 (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: 141662; 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
      1650 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 60 0C (0.5 min) ^ 30 0C/min -> 160 0C ^ 5 0C/min -> 290 0C (5 min) (total run time 34.8 min); CAS no: 141662; Active phase: DB-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Holstege, D.M.; Scharberg, D.L.; Richardson, E.R.; Moller, G., Multiresidue screen for organophosphorus insecticides using gel permeation chromatography -- silica gel cleanup, J. Ass. Offic. Anal. Chem, 74(2), 1991, 394-399.) NIST Spectra nist ri

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

Density: 1.2±0.1 g/cm3
Boiling Point: 307.5±34.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.7 mmHg at 25°C
Enthalpy of Vaporization: 54.8±3.0 kJ/mol
Flash Point: 139.7±25.7 °C
Index of Refraction: 1.457
Molar Refractivity: 54.9±0.3 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 5
#Rule of 5 Violations: 0
ACD/LogP: -0.36
ACD/LogD (pH 5.5): -0.24
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 17.71
ACD/LogD (pH 7.4): -0.24
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 17.71
Polar Surface Area: 75 Å2
Polarizability: 21.8±0.5 10-24cm3
Surface Tension: 36.5±3.0 dyne/cm
Molar Volume: 201.6±3.0 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) =  -1.10
    Log Kow (Exper. database match) =  0.00
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  337.53  (Adapted Stein & Brown method)
    Melting Pt (deg C):  79.21  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00026  (Modified Grain method)
    MP  (exp database):  < 25 deg C
    VP  (exp database):  1.60E-04 mm Hg at 25 deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  2.782e+004
       log Kow used: 0.00 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  1e+006 mg/L (25 deg C)
        Exper. Ref:  SHIU,WY ET AL (1990)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L
    Wat Sol (Exper. database match) =  1000000.00
       Exper. Ref:  SHIU,WY ET AL (1990)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Esters (phosphate)
       Acrylamides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.20E-012  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 5.03E-11  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.917E-009 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.00  (exp database)
  Log Kaw used:  -8.687  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  8.687
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.1587
   Biowin2 (Non-Linear Model)     :   1.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7745  (weeks       )
   Biowin4 (Primary Survey Model) :   4.1763  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2961
   Biowin6 (MITI Non-Linear Model):   0.1016
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.3238
 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):  0.0213 Pa (0.00016 mm Hg)
  Log Koa (Koawin est  ): 8.687
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000141 
       Octanol/air (Koa) model:  0.000119 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.00505 
       Mackay model           :  0.0111 
       Octanol/air (Koa) model:  0.00946 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  52.2422 E-12 cm3/molecule-sec
      Half-Life =     0.205 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.457 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     1.137500 E-17 cm3/molecule-sec
      Half-Life =     1.007 Days (at 7E11 mol/cm3)
      Half-Life =     24.179 Hrs
   Fraction sorbed to airborne particulates (phi): 0.00809 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  366.2
      Log Koc:  2.564 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 0.00 (expkow database)

 Volatilization from Water:
    Henry LC:  5.03E-011 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River: 1.793E+007  hours   (7.469E+005 days)
    Half-Life from Model Lake : 1.956E+008  hours   (8.148E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.76  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       0.00118         4.08         1000       
   Water     38.5            360          1000       
   Soil      61.4            720          1000       
   Sediment  0.0711          3.24e+003    0          
     Persistence Time: 582 hr

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