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SPINOSAD

Product NameSPINOSAD
CAS168316-95-8
MFC41H65NO10
MW731.96
EINECS605-513-9
MOL File168316-95-8.mol

Chemical Properties

Melting point	110℃
storage temp.	0-6°C
solubility	Ethanol: 1 mg/ml
form	Solid
color	White to off-white
Henry's Law Constant	5.3×10⁶ mol/(m³Pa) at 25℃, Maniere et al. (2011)
InChIKey	RQOIAWYOVOXMST-UHFFFAOYSA-N
SMILES	N(C1C(OC(CC1)OC2CCCC(OC(=O)CC3C4C(C5C(CC4)CC(C5)OC6C(C(C(C(C6)C)OC)OC)OC)CC3C(=O)C2C)CC)C)(C)C
EPA Substance Registry System	Spinosad (168316-95-8)

Safety Information

Hazard Codes	N
Risk Statements	50/53
Safety Statements	61
RIDADR	UN3077 9/PG 3
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1
Toxicity	LD50 in rats, mallard ducks, quail (mg/kg): >3600, >2000, >2000 orally (Crouse)

Usage And Synthesis

Description

Spinosad is a naturally-occurring insecticide found in the the soil bacterium S. spinosa. It is a mixture of the macrocyclic lactones spinosyn A and spinosyn D , which act as agonists of insect nicotinic acetylcholinesterase receptors (nAChRs). Oral administration of spinosad induces toxicity in fruit flies including C. capitata, B. curcurbitae, and B. dorsalis (LC₅₀s = 2.8-4.2, 4.3-5.5, and 3.1-3.3 μg/ml, respectively) but has low toxicity in vertebrates. It also inhibits canine P-glycoprotein (P-gp; IC₅₀ = 0.2 μg/ml). Formulations containing spinosad have been used in the agricultural and veterinary control of insects.

Uses

Insecticide.

Definition

Isolated from Saccharopolyspora spinosa (Actinomycetes).

Hazard

A poison by inhalation. Moderately toxic by ingestion.

in vivo

Spinosad is a natural mixture of the pediculicidal tetracyclic macrolides spinosyn A and spinosyn D. Spinosad 0.9% mainly interferes with nicotinic acetylcholine receptors in insects, thereby producing neuronal excitation that results in paralysis of lice from neuromuscular fatigue after extended periods of hyperexcitation. Spinosad 0.9% kills both permethrin-susceptible and permethrin-resistant populations of lice. It is also ovicidal, killing both eggs (nits) and lice^[5].
Spinosad causes in vivo oxidative effects in the brain of Oreochromis niloticus. Spinosad causes elevations in the contents of tGSH, GSH, GSSG, Hsp70, and reductions in the ratio of GSH/GSSG and GPx activity and an induction in the GR (glutathione reducta) activity. Spinosad has oxidative effects in the brain tissue by altering the parameters in GSH-related antioxidant system and Hsp70^[6].

References

[1] WESLEY J. MAGUIRE*. Comprehensive Determination of Unregulated Pesticide Residues in Oregon Cannabis Flower by Liquid Chromatography Paired with Triple Quadrupole Mass Spectrometry and Gas Chromatography Paired with Triple Quadrupole Mass Spectrometry[J]. Journal of Agricultural and Food Chemistry, 2019, 67 46: 12670-12674. DOI: 10.1021/acs.jafc.9b01559
[2] D. T. VO. Insect nicotinic acetylcholine receptor agonists as flea adulticides in small animals[J]. Journal of veterinary pharmacology and therapeutics, 2010, 33 4: 315-322. DOI: 10.1111/j.1365-2885.2010.01160.x
[3] JOHN D STARK Neil M Roger Vargas. Toxicity of spinosad in protein bait to three economically important tephritid fruit fly species (Diptera: Tephritidae) and their parasitoids (Hymenoptera: Braconidae).[J]. Journal of Economic Entomology, 2004, 97 3: 911-915. DOI: 10.1603/0022-0493(2004)097[0911:tosipb]2.0.co;2
[4] T S AMARAL. Short-term effects of a spinosyn’s family insecticide on energy metabolism and liver morphology in frugivorous bats Artibeus lituratus (Olfers, 1818).[J]. Brazilian Journal of Biology, 2012, 72 2: 299-304. DOI: 10.1590/s1519-69842012000200010
[5] SCHRICKX J A. Spinosad is a potent inhibitor of canine P-glycoprotein[J]. Veterinary journal, 2014, 200 1: Pages 195-196. DOI: 10.1016/j.tvjl.2014.01.012

SPINOSAD

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