| Identification | Back Directory | [Name]
SPINOSAD | [CAS]
168316-95-8 | [Synonyms]
SPINOS
Spinosad [iso]
Tracer naturalyte
Spinosad Standard
SPINOSAD USP/EP/BP
SpinosadSolution,1000mg/L,1ml
Spinosad @100 μg/mL in Acetonitrile
Spinosad@1000 μg/mL in Acetonitrile
Spinosad Solution in Methanol, 100μg/mL
Mixture of Spinosyn A and Spinosyn D
Spinosad(MixofIsomers)Solution,10mg/L,10ml
Spinosad (Mixture of Spinosyn A and Spinosyn D)
48%SC Spinosad Insecticide 168316-95-8 Vegetable Garden Insecticides
168316-95-8 arochemical Biological Pesticides Spinosad Insecticide 48%SC | [EINECS(EC#)]
605-513-9 | [Molecular Formula]
C41H65NO10 | [MDL Number]
MFCD01753923 | [MOL File]
168316-95-8.mol | [Molecular Weight]
731.96 |
| Chemical Properties | Back Directory | [Definition]
Isolated from Saccharopolyspora
spinosa (Actinomycetes).
| [Melting point ]
110℃ | [storage temp. ]
0-6°C | [solubility ]
Ethanol: 1 mg/ml | [form ]
neat | [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) |
| Questions And Answer | Back Directory | [Preparation]
Similar to other macrocyclic lactones, SPINOSAD is synthesized from acetic acid and propionic acid units via a polyene synthesis pathway. However, its synthesis process has unique features: 1) The formation of the three intramolecular C-C bonds (C3-C14, C4-C12, and C7-C11) and the closure of the ring are clearly achieved through a 4+2 cycloaddition reaction and an aldol condensation or a Michel condensation reaction; L-rhamnose and D-fructosamine are attached to the hydroxyl groups at positions 9 and 17, respectively, after lactonization to form glycosidic aglycones, followed by methylation of the 2,3,4-hydroxyl groups of rhamnose. From the synthetic pathway of SPINOSAD, the formation of most of its minor components can be considered as the result of different degrees of oxygen methylation of rhamnose, different degrees of nitrogen methylation of fructosamine, and the exchange of acetic acid and propionic acid units during the assembly of long-chain fatty acid intermediates. |
| Hazard Information | Back Directory | [Uses]
Insecticide. | [Hazard]
A poison by inhalation. Moderately toxic
by ingestion.
| [Description]
Spinosad is a naturally-occurring insecticide found in the the soil bacterium S. spinosa.1 It is a mixture of the macrocyclic lactones spinosyn A (Item No. 16528) and spinosyn D (Item No. 19158), 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.2,3,4 It also inhibits canine P-glycoprotein (P-gp; IC50 = 0.2 μg/ml).5 Formulations containing spinosad have been used in the agricultural and veterinary control of insects. | [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 |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS09 | [Signal word ]
Warning | [Hazard statements ]
H410 | [Precautionary statements ]
P273-P391-P501 | [Hazard Codes ]
N | [Risk Statements ]
50/53 | [Safety Statements ]
61 | [RIDADR ]
UN3077 9/PG 3 | [WGK Germany ]
3 | [REACH Registrations]
Inactive | [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) |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
|