Spinosyns
Title: Spinosyns
CAS Registry Number: 131929-60-7
Literature References: Class of fermentation derived 12 membered macrocyclic lactones in a unique tetracyclic ring. At least 20 spinosyns have been isolated from Saccharopolyspora spinosa; variations in the two sugars account for most of the structural and insecticidal activity differences. Isolation and biological activity: L. D. Boeck et al., EP 375316 (1990 to Lilly); eidem, US 5496931 (1996 to DowElanco); and structure determn: H. A. Kirst et al., Tetrahedron Lett. 32, 4839 (1991). Soil degradation: K. A. Hale, D. E. Portwood, J. Environ. Sci. Health B31, 477 (1996). HPLC determn in vegetables: L.-T. Yeh et al., J. Agric. Food Chem. 45, 1746 (1997); in soil and water: S. D. West, ibid. 3107. Uptake and metabolism in larvae: T. C. Sparks et al., Proc. Beltwide Cotton Conf. 2, 1259 (1997). Mode of action study: V. L. Salgado et al., Pestic. Biochem. Physiol. 60, 103 (1998). Review of physical and biological properties: C. V. DeAmicis et al., ACS Symp. Ser. 658, 144-154 (1997). Review: G. D. Crouse, T. C. Sparks, Rev. Toxicol. 2, 133-146 (1998).
 
Derivative Type: Spinosyn A
CAS Name: (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-[(6-Deoxy-2,3,4-tri-O-methyl-a-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
Additional Names: lepicidin A
Manufacturers' Codes: A-83543A; LY-232105
Molecular Formula: C41H65NO10
Molecular Weight: 731.96
Percent Composition: C 67.28%, H 8.95%, N 1.91%, O 21.86%
Literature References: Total synthesis: L. A. Paquette et al., J. Am. Chem. Soc. 120, 2553 (1998).
Properties: White, odorless crystalline solid, mp 118°. pKa 8.1. uv max (methanol): 243 nm (e 11000). [a]27436 -262.7° (methanol). Vapor pressure: 2.4 ´ 10-10. Soly in water (ppm): 290 (pH 5), 235 (pH 7), 16 (pH 9), distilled 20. Soly (w/v%): methanol 19, acetone 17, dichloromethane >50, hexane 0.45%. LD50 in rats (mg/kg): 3783-5000 orally (Crouse).
Melting point: mp 118°
pKa: pKa 8.1
Optical Rotation: [a]27436 -262.7° (methanol)
Absorption maximum: uv max (methanol): 243 nm (e 11000)
Toxicity data: LD50 in rats (mg/kg): 3783-5000 orally (Crouse)
 
Derivative Type: Spinosyn D
CAS Registry Number: 131929-63-0
Manufacturers' Codes: A-83543D
Molecular Formula: C42H67NO10
Molecular Weight: 745.98
Percent Composition: C 67.62%, H 9.05%, N 1.88%, O 21.45%
Properties: Odorless, white crystalline solid. mp 169°. pKa 7.8. uv max (methanol): 243 nm (e 11000). [a]27436 -297.5° (methanol). Vapor pressure: 2.0 ´ 10-10. Soly in water (ppm): 28 (pH 5), 0.329 (pH 7), 0.04 (pH 9), distilled 1.3. Soly (w/v%): methanol 0.25, acetone 1.0, dichloromethane 45, hexane 0.07%.
Melting point: mp 169°
pKa: pKa 7.8
Optical Rotation: [a]27436 -297.5° (methanol)
Absorption maximum: uv max (methanol): 243 nm (e 11000)
 
Derivative Type: Spinosad
CAS Registry Number: 168316-95-8
Manufacturers' Codes: XDE-105; DE-105
Trademarks: Conserve (Dow AgroSci.); Justice (Dow AgroSci.); Naturalyte (Dow AgroSci.); SpinTor (Dow AgroSci.); Success (Dow AgroSci.); Tracer (Dow AgroSci.)
Literature References: Mixture of spinosyns A and D. Effect on beneficial insects: D. Murray, R. Lloyd, Australian Cottongrower 18, 62 (1997).
Properties: Light grey to white crystals (tech). LD50 in rats, mallard ducks, quail (mg/kg): >3600, >2000, >2000 orally (Crouse).
Toxicity data: LD50 in rats, mallard ducks, quail (mg/kg): >3600, >2000, >2000 orally (Crouse)
 
Use: Insecticide.

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