| Identification | Back Directory | [Name]
SPINOSAD | [CAS]
131929-60-7 | [Synonyms]
a83543a
SPINOSAD
Hsdb 7006
Spinosyns
spinosyna
Spinosad A
lepicidina
Ccris 8937
Spinosyn A Solution
Spinosyn A Solution, 1000ppm
Lepicidin A, A 83543A, LY 232105
Spinosad A Solution in Methanol, 1000μg/mL
(2r-(2r*,3as*,5ar*,5bs*,9s*,13s*(2r*,5s*,6r*),14r*,16as*,16br*))-ethyl
)oxy)-13-((5-dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)oxy)-9-ethyl-14-m
1h-as-indaceno(3,2-d)oxacyclododecin-7,15-dione,2,3,3a,5a,5b,6,9,10,11,12,13,1
4,16a,16b-tetradecahydro-2-((6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl
2-d)oxacyclododecin-7,15-dione,2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-2-((6-deoxy-2,3,4-tri-o-methyl-alpha-l-mannopyranosyl)oxy)-13-((5-dimethylamino)tetrahydro-6-methyl-2h-pyran-2-yl)
2-{(6-Deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy}-13-{{5-(dimethylamino)tetr ahydro-6-methyl-2H-pyran-2-yl}oxy}-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-t etradecahydro-14-methyl-1H-as-Indaceno{3,2-d}oxacyclododecin-7,15-dione
(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
1H-as-Indaceno3,2-doxacyclododecin-7,15-dione, 2-(6-deoxy-2,3,4-tri-O-methyl-.alpha.-L-mannopyranosyl)oxy-13-(2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yloxy-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-, (2R,3a
1H-as-Indaceno[3,2-d]oxacyclododecin-7,15-dione, 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-, (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-
1H-As-indaceno(3,2-D)oxacyclododecin-7,15-dione, 2-((6-deoxy-2,3,4-tri-o-methyl-alpha-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-, (2R,3as,5ar,5bs,9S,13S,14R,16as,16br)-
1H-As-indaceno(3,2-D)oxacyclododecin-7,15-dione, 2,3,3A,5A,5B,6,9,10,11,12,13,14,16A,16B-tetradecahydro-2-((6-deoxy-2,3,4-tri-o-methyl-alpha-L-mannopyranosyl)oxy)- 13-((5-dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-, (2R-(2R*,3as*,5ar*,5bs*,9S*,13S*(2R*,5S*,6R*),14R*,16as*,16br*))- | [EINECS(EC#)]
620-162-1 | [Molecular Formula]
C41H65NO10 | [MDL Number]
MFCD01753923 | [MOL File]
131929-60-7.mol | [Molecular Weight]
731.96 |
| Chemical Properties | Back Directory | [Boiling point ]
801.5±65.0 °C(Predicted) | [density ]
1.16±0.1 g/cm3(Predicted) | [vapor pressure ]
Spinosyn A: 3.2 x 10-8 Pa
Spinosyn D: 2.1 x 10-8 Pa | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
solid | [pka]
Spinosyn A: 8.1 (base);
Spinosyn D: 7.8 (base) | [Water Solubility ]
Spinosyn A: 290 mg l-1 (pH 5);
Spinosyn D: 29 mg l-1 (pH 5) | [color ]
White to off-white | [InChIKey]
SRJQTHAZUNRMPR-XOBNMGJWNA-N | [EPA Substance Registry System]
1H-as-Indaceno[3, 2-d]oxacyclododecin-7,15- dione, 2-[(6-deoxy-2,3,4-tri-O-methyl-. alpha.-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-, (2R,3aS,5aR,5bS,9S,13S,14R, 16aS,16bR)-(131929-60-7) |
| Hazard Information | Back Directory | [Chemical Properties]
pale off-white crystalline solid with a slight stale earthy odor. Its vapor pressure is approximately 1.3×10-10 Pa. In aqueous solution at a pH of 7.74, it is relatively stable to metals and metal ions for 28 days. Its photodegradation half-life in soil is 9-10 days; its half-life in water is <1 day. It is relatively stable in aqueous solution within the pH range of 5-7; at pH 9, its half-life is >200 days. Spinosad is a mixture of more than ten components, the main ones being A and D. Spinosad A has a melting point of 84-99.5°C and a vapor pressure of 3.2×10-10 Pa. Its solubility in water is 290 mg/L (pH 5.0), 235 mg/L (pH 7.0), and 16 mg/L (pH 9.0). Its partition coefficients are 2.8, 4.0, and 5.2 at the corresponding pH values, respectively. Spinosad D has a melting point of 161.5-170°C, a vapor pressure of 2.1×10-10 Pa, and solubilities in water of 29 mg/L (pH=5.0), 0.332 mg/L (pH=7.0), and 0.053 mg/L (pH=90.0). The partition coefficients are 3.2, 4.5, and 5.2 at the corresponding pH values, respectively. | [Uses]
Spinosyn A is the major component of a complex of unusual, hydrophobic macrocyclic lactones isolated from Saccharopolyspora spinosa in 1991. The 12-membered macrocyclic lactone is fused to form a rare 12-5-6-5 tetracyclic ring system, with the macrocycle and the terminal cyclopentane bearing glycosides. Spinosyn A is a potent insecticide for crop pathogens and ectoparasite control on animals. The spinosyns have a unique mechanism of action involving disruption of nicotinic acetylcholine receptors. | [Definition]
ChEBI: A spinosyn in which the sugar amino and hydroxy groups are globally methylated. One of the two active ingredients of spinosad. | [Biological Activity]
spinosyn a is an insect nicotinic acetylcholinesterase receptors (nachrs) agonist and potent insecticide.the spinosyns are a family of macrolide natural products produced by the soil microorganism saccharopolyspora spinosa. spinosyn a is identified as a naturally-occurring macrocyclic lactone that is a potent insecticide. | [Veterinary Drugs and Treatments]
For the prevention and treatment of fleas for one month on dogs 14 weeks of age and older.
Spinosad is a group 5 nicotinic acetylcholine receptor agonist, that causes involuntary muscle contractions and tremors secondary
to motor neuron activation. Prolonged exposure causes paralysis and flea death. Flea death begins within 30 minutes of dosing and in 4
hours is complete. Spinosad does not interact with bindings sites of other insecticidal agents (GABA-ergic or nicotinic). | [in vitro]
the mixture of spinosyns a and d, a commercial insecticide tracertm (dowagrosciences), is useful against various crop pests such as tobacco budworm. it was found that the deoxy analogs of spinosyns a were more potent insecticides than their respective parent factor. moreover, the 2’-desmethoxy analogs of spinosyns a showed insecticidal potency against h. virescens greater than that of spinosyns a and d, suggesting that polarity was not well tolerated. furthermore, the activity of 3'-deoxy spinosyn j was about the same as spinosyn a, and the activity of 2'-deoxy spinosyn h was found to be slightly greater than that of spinosyn a [1]. | [Metabolic pathway]
Spinosad consists of two major components, namely
psinosyns A (ca 85%) and D (ca 15%). When either
14C-spinosyn A or -spinosyn D is applied in the soil
under aerobic conditions, the major degradation
product of spinosyn A is spinosyn B, resulting from demethylation on the forosamine sugar. Other
degradation products are hydroxylation products of
psinosyns A and B, probably on the aglycone portion
of the molecule. | [storage]
Store at -20°C | [Degradation]
Spinosad is relatively stable in water with no observed decomposition
between pH 5 and 7. Measured DT50 values at pH 9 were 200 and 259
days, respectively, for spinosyns A and D (Saunders and Bret, 1997).
Aqueous photolysis was very rapid with a DT50 of < 1 day in pH 7 buffered
water at 25 °C (DowElanco, 1996). Spinosad was rapidly dissipated
and degraded in an outdoor mesocosm study and on plant surfaces
(Saunders and Bret, 1997). | [Toxicity evaluation]
Acute oral LD50 for rats: 2,000-5,000 mg/kg | [References]
[1] l. c. creemer, h. a. kirst, j. w. paschal, et al. synthesis and insecticidal activity of spinosyn analogs functionally altered at the 2'-,3'- and 4'-positions of the rhamnose moiety. j.antibiot.(tokyo) 53(2), 171-178 (2000). |
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