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Insecticide

Spinosad

Chemical Name:  
IUPAC: mixture of 50–95% (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyloxy)-13-(4-dimethylamino-2,3,4,6-tetradeoxy-β-D-erythropyranosyloxy)-9-ethyl-2,3,3a,5a,5b,6,7,9,10,11,12,13,14,15,16a,16b-hexadecahydro-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecine-7,15-dione and 50–5% (2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-2-(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyloxy)-13-(4-dimethylamino-2,3,4,6-tetradeoxy-β-D-erythropyranosyloxy)-9-ethyl-2,3,3a,5a,5b,6,7,9,10,11,12,13,14,15,16a,16b-hexadecahydro-4,14-dimethyl-1H-as-indaceno[3,2-d]oxacyclododecine-7,15-dione

  CAS:(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-13-[[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione
mixture with
(2S,3aR,5aS,5bS,9S,13S,14R,16aS,16bS)-2-[(6-deoxy-2,3,4-tri-O-methyl-α-L-mannopyranosyl)oxy]-13-[[(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl]oxy]-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-4,14-dimethyl-1H-as-indaceno[3,2-d]oxacyclododecin-7,15-dione
Formula:   Spinosyn AC41H65NO10Spinosyn DC42H67NO10

Molecular Weight:  Spinosyn A: 731.98
                     Spinosyn D: 745.99

CAS No.: 131929-60-7 (Spinosyn A, used by WHO Acute list)
168316-95-8 (Used in WHO Acute Hazard list)

Structure:
          Structural formula of spinosad
Description:
Appearance: Light grey-white powder
Vapour Pressure: Spinosyn A: 3.0×10-5
              Spinosyn D: 2.0×10-5
Melting Point: Spinosyn A: 84 to 99.5°C(98.3% purity)
            Spinosyn D: 161.5 to 170°C(98% purity)

Solubility:                     Spinosyn A          Spinosyn D
         Water, mg/l at 20°C     89                  0.50
         PH 5, mg/l at 20°C     290                 29
         PH 7, mg/l at 20°C     235                 0.33
         PH 9, mg/l at 20°C     16                  0.053
  Solvent solubility:
Spinosyn A          Spinosyn D
         dichloromethane, g/l at 20°C   525               448
methanol, g/l at 20°C          190               2.5
acetone, g/l at 20°C            168               10
acetonitrile, g/l at 20°C         134               2.6
amyl acetate, g/l at 20°C        37                23
hexane, g/l at 20°C             4.5               0.74
1-octanol, g/l at 20°C           9.3               1.3
toluene, g/l at 20°C             457              152
isopropyl alcohol, g/l at 20°C    40                1.3
ethyl acetate, g/l at 20°C       194                19  
n-heptane, g/l at 20°C          12.4               0.3  
xylene g/l at 20°C            >250              64

Hydrolysis at 25°C, sterile buffer, dark       Spinosyn A          Spinosyn D

PH 5               not observed in          not observed in
30-day test             30-day test
PH 7               not observed in          not observed in
30-day test              30-day test
PH 9    half life    approx. 100-300 days      approx. 100-300 days

Spinosyn A          Spinosyn D
Photolysis - half-life for degradation in      22.3 h              19.7 h
dilute aqueous sterile buffer at pH       
7, June-July, Indiana USA, 39.9°N.
 
Dissociation constant (determined by
capillary electrophoresis) pKa (20°C)        8.10              7.87  
Equivalent Ka                  7.94×10-9         1.35×10-8

Technical material: 
Content: ≥97% (Spinosyn A≥70%Spinosyn D≤30%)

 

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