ChemSpider 2D Image | fenamiphos | C13H22NO3PS

fenamiphos

  • Molecular FormulaC13H22NO3PS
  • Average mass303.357 Da
  • Monoisotopic mass303.105804 Da
  • ChemSpider ID28827

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

1Y1&MPO&O2&OR C1 DS1 [WLN]
22224-92-6 [RN]
244-848-1 [EINECS]
Ethyl 3-methyl-4-(methylsulfanyl)phenyl isopropylphosphoramidate [ACD/IUPAC Name]
Ethyl 3-methyl-4-(methylsulfanyl)phenyl propan-2-ylphosphoramidate
Ethyl-3-methyl-4-(methylsulfanyl)phenyl-isopropylphosphoramidat [German] [ACD/IUPAC Name]
fenamiphos [BSI] [ISO]
Isopropylphosphoramidate d'éthyle et de 3-méthyl-4-(méthylsulfanyl)phényle [French] [ACD/IUPAC Name]
phénamiphos [French] [ISO]
Phosphoramidic acid, N-(1-methylethyl)-, ethyl 3-methyl-4-(methylthio)phenyl ester [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

45483_RIEDEL [DBID]
AI3-27572 [DBID]
B 68138 [DBID]
BAY 68138 [DBID]
Bayer 68138 [DBID]
BRN 4752893 [DBID]
Caswell No. 453A [DBID]
CCRIS 4694 [DBID]
ENT 27572 [DBID]
EPA Pesticide Chemical Code 100601 [DBID]
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      Off-white to tan, waxy solid. [insecticide] [Note: Found commercially as a granular ingredient (5-15%) or in an emulsifiable concentrate (400 g/l).] NIOSH TB3675000
    • First-Aid:

      Eye: Irrigate immediately Skin: Soap flush immediately Breathing: Respiratory support Swallow: Medical attention immediately NIOSH TB3675000
    • Exposure Routes:

      inhalation, skin absorption, ingestion, skin and/or eye contact NIOSH TB3675000
    • Symptoms:

      Nausea, vomiting, abdominal cramps, diarrhea, salivation; headache, dizziness, lassitude (weakness, exhaustion); rhinorrhea (discharge of thin mucus), chest tightness; blurred vision, miosis; cardiac irregularities; muscle fasciculation; dyspnea (breathing difficulty) NIOSH TB3675000
    • Target Organs:

      respiratory system, central nervous system, cardiovascular system, blood cholinesterase NIOSH TB3675000
    • Incompatibility:

      None reported [Note: May hydrolyze under alkaline conditions.] NIOSH TB3675000
    • Personal Protection:

      Skin: Prevent skin contact Eyes: Prevent eye contact Wash skin: When contaminated/Daily Remove: When wet or contaminated Change: Daily Provide: Quick drench NIOSH TB3675000
    • Exposure Limits:

      NIOSH REL : TWA 0.1 mg/m 3 [skin] OSHA PEL ?: none NIOSH TB3675000
  • Gas Chromatography
    • Retention Index (Normal Alkane):

      2110.1 (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: 22224926; 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
      2117.7 (Program type: Complex; Column... (show more) class: Standard non-polar; Column diameter: 0.247 mm; Column length: 15 m; Column type: Capillary; Description: 1 min at 90 C; 90-150 C at 20 deg/min; 150-250 C at 5 deg/min; hold at 250 C for elution of last component; CAS no: 22224926; Active phase: SE-30; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Ripley, B.D.; Braun, H.E., Retention time data for organochlorine, organophosphorus, and organonitrogen pesticides on SE-30 capillary column and application of capillary gas chromatography to pesticide residue analysis, J. Ass. Offic. Anal. Chem, 66(5), 1983, 1084-1095.) NIST Spectra nist ri
      2152 (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 0C(1 min) ^ 25 0C/min -> 125 0C ^ 10 0C/min -> 300 0C (10 min); CAS no: 22224926; Active phase: 5 % Phenyl methyl siloxane; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Department of Food Safety, Ministry of Health; Welfare, Analytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods, 2006.) NIST Spectra nist ri
      2154 (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 0C(1 min) ^ 25 0C/min -> 125 0C ^ 10 0C/min -> 300 0C (10 min); CAS no: 22224926; Active phase: 5 % Phenyl methyl siloxane; Carrier gas: Helium; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Department of Food Safety, Ministry of Health; Welfare, Analytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods, 2006., Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 70 C (3.5 min) ^ 50 C/min -> 150 C ^ 5 C/min -> 180 C (5 min) ^ 4 C/min -> 205 C (5 min) ^ 4 C/min -> 300 C (5 min); CAS no: 22224926; Active phase: DB-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Martinez Vidal, J.L.; Arrebola, F.J.; Mateu-Sanchez, M., Application of gas chromatography-tandem mass spectrometry to the analysis of pesticides in fruits and vegetables, J. Chromatogr. A, 959, 2002, 203-213.) NIST Spectra nist ri
      2142.9 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 80C(1min) => 10C/min =>160C (5min) => 3C/min =>240C =>25C/min =>280C(10min); CAS no: 22224926; Active phase: DB-5MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Chu, X.-G.; Hu, X.-Z.; Yao, H.-Y., Determination of 266 pesticide residues in apple juice by matrix solid-phase dispersion and gas chromatography-mass selective detection, J. Chromatogr. A, 1063, 2005, 201-210.) NIST Spectra nist ri
      2122.2 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 80C(2min) =>15C/min =>190C(4min) => 10C/min => 290C(6min); CAS no: 22224926; Active phase: CP-Sil 8CB-MS; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Goncalves, C.; Alpendurada, M.F., Solid-phase micro-extraction-gas chromatography-(tandem) mass spectrometry as a tool for pesticide residue analysis in water samples at high sensitivity and selectivity with confirmation capabilities, J. Chromatogr. A, 1026, 2004, 239-250.) NIST Spectra nist ri
      2153.6 (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: 22224926; 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
      2123.1 (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: 15 K/min; Start T: 57 C; End T: 290 C; End time: 15 min; Start time: 1.5 min; CAS no: 22224926; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.2 um; Data type: Normal alkane RI; Authors: Haib, J.; Hofer, I.; Renaud, J.-M., Analysis of multiple pesticide residues in tobacco using pressurized liquid extraction, automated solid-phase extraction clean-up and gas chromatography-tandem mass spectrometry, J. Chromatogr. A, 1020, 2003, 173-187.) NIST Spectra nist ri
      2152.5 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 45 0C (2.66 min) ^ 40 0C/min -> 170 0C ^ 4 0C/min -> 220 0C ^ 20 0C/min -> 280 0C (15.72 min); CAS no: 22224926; Active phase: HP-5; Carrier gas: He; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Frenzel, T.; Sochor, H.; Speer, K.; Uihlein, M., Rapid multimethod for verification and determination of toxic pesticides in whole blood by means of capillary GC-MS, J. Anal. Toxicol., 24, 2000, 365-371.) NIST Spectra nist ri
      2145.3 (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: 22224926; 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
      2159.3 (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: 22224926; 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
      2150.3 (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: 150 C; End T: 275 C; End time: 3 min; Start time: 5 min; CAS no: 22224926; 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
      2144.7 (Program type: Complex; Column... (show more) class: Semi-standard non-polar; Column diameter: 0.25 mm; Column length: 30 m; Column type: Capillary; Description: 40 0C 92 min) ^ 40 0C/min -> 60 0C ^ 4 0C/min -> 310 0C (10 min); CAS no: 22224926; Active phase: SPB-5; Phase thickness: 0.25 um; Data type: Normal alkane RI; Authors: Draper, W.M., Optimizing nitrogen-phosphorus detector gas chromatography for pesticide analysis, J. Agric. Food Chem., 43, 1995, 2077-2082.) NIST Spectra nist ri
      2137.9 (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: 22224926; 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
      2122.4 (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: 22224926; 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

Density: 1.1±0.1 g/cm3
Boiling Point: 375.6±52.0 °C at 760 mmHg
Vapour Pressure: 0.0±0.8 mmHg at 25°C
Enthalpy of Vaporization: 62.3±3.0 kJ/mol
Flash Point: 181.0±30.7 °C
Index of Refraction: 1.524
Molar Refractivity: 81.0±0.4 cm3
#H bond acceptors: 4
#H bond donors: 1
#Freely Rotating Bonds: 7
#Rule of 5 Violations: 0
ACD/LogP: 3.68
ACD/LogD (pH 5.5): 3.22
ACD/BCF (pH 5.5): 165.37
ACD/KOC (pH 5.5): 1347.64
ACD/LogD (pH 7.4): 3.22
ACD/BCF (pH 7.4): 165.37
ACD/KOC (pH 7.4): 1347.65
Polar Surface Area: 83 Å2
Polarizability: 32.1±0.5 10-24cm3
Surface Tension: 41.3±5.0 dyne/cm
Molar Volume: 264.7±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) =  3.29
    Log Kow (Exper. database match) =  3.23
       Exper. Ref:  Hansch,C et al. (1995)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  390.08  (Adapted Stein & Brown method)
    Melting Pt (deg C):  84.78  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  8.72E-006  (Modified Grain method)
    MP  (exp database):  49 deg C
    VP  (exp database):  1.00E-06 mm Hg at 25 deg C
    Subcooled liquid VP: 1.73E-006 mm Hg (25 deg C, exp database VP )

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  20.47
       log Kow used: 3.23 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  329 mg/L (20 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  194.9 mg/L
    Wat Sol (Exper. database match) =  329.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   9.66E-011  atm-m3/mole
   Group Method:   Incomplete
   Exper Database: 1.21E-09  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.700E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.23  (exp database)
  Log Kaw used:  -7.306  (exp database)
      Log Koa (KOAWIN v1.10 estimate):  10.536
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6578
   Biowin2 (Non-Linear Model)     :   0.3270
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4539  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.3415  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1238
   Biowin6 (MITI Non-Linear Model):   0.0057
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.2801
 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):  0.000231 Pa (1.73E-006 mm Hg)
  Log Koa (Koawin est  ): 10.536
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.013 
       Octanol/air (Koa) model:  0.00843 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.32 
       Mackay model           :  0.51 
       Octanol/air (Koa) model:  0.403 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  77.7064 E-12 cm3/molecule-sec
      Half-Life =     0.138 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.652 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.415 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  225.1
      Log Koc:  2.352 

 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 = 1.787 (BCF = 61.25)
       log Kow used: 3.23 (expkow database)

 Volatilization from Water:
    Henry LC:  1.21E-009 atm-m3/mole  (Henry experimental database)
    Half-Life from Model River: 8.428E+005  hours   (3.512E+004 days)
    Half-Life from Model Lake : 9.194E+006  hours   (3.831E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               8.20  percent
    Total biodegradation:        0.14  percent
    Total sludge adsorption:     8.05  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       0.00877         3.3          1000       
   Water     12.5            900          1000       
   Soil      87              1.8e+003     1000       
   Sediment  0.482           8.1e+003     0          
     Persistence Time: 1.73e+003 hr




                    

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