Spinosad
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| Category | Agricultural |
| Catalog number | BBF-05897 |
| CAS | 168316-95-8 |
| Molecular Weight | 1477.94 |
| Molecular Formula | C42H67NO10.C41H65NO10 |
| Purity | ≥95% |
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Description
Spinosad is a broad-spectrum and naturally-occurring insecticide found in the the soil bacterium S. spinosa. Spinosad is a mixture of the macrocyclic lactones spinosyn A and spinosyn D , which act as agonists of insect nicotinic acetylcholinesterase receptors (nAChRs).
Specification
| Related CAS | 131929-60-7 (Spinosyn A) 131929-63-0 (Spinosyn D) |
| Synonyms | Spinosyn A and D (mixture); Blackhawk; Comfortis; Conserve; Entrust; Entrust WP; Extinosad; GF 120; GF 120 Fruit Fly Bait; GF 120 NF Naturalyte; GF 120 Naturalyte Fruit Fly Bait; GF 1587; Gardens Alive Bulls-Eye; Laser; Laser (insecticide); Naturalure; Naturalure Fruit Fly Bait; Naturalyte; PP 105; SpinTor; Spinoace; Spinosad 45SC; Spinosad NT; Spinosyn A-spinosyn D mixt.; Success; Success 4; Success Naturalyte; Tracer; Tracer Naturalyte; Tracer Naturalyte Insect Control |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2S,5R,7S,9S,10S,14R,15S,19S)-15-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-19-ethyl-4,14-dimethyl-7-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione;(1S,2R,5S,7R,9R,10S,14R,15S,19S)-15-[(2R,5S,6R)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-19-ethyl-14-methyl-7-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-20-oxatetracyclo[10.10.0.02,10.05,9]docosa-3,11-diene-13,21-dione |
| Canonical SMILES | CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C=CC3C2CC(=O)O1)OC5C(C(C(C(O5)C)OC)OC)OC)C)OC6CCC(C(O6)C)N(C)C.CCC1CCCC(C(C(=O)C2=CC3C4CC(CC4C(=CC3C2CC(=O)O1)C)OC5C(C(C(C(O5)C)OC)OC)OC)C)OC6CCC(C(O6)C)N(C)C |
| InChI | InChI=1S/C42H67NO10.C41H65NO10/c1-11-26-13-12-14-35(53-37-16-15-34(43(6)7)24(4)49-37)23(3)38(45)33-20-31-29(32(33)21-36(44)51-26)17-22(2)28-18-27(19-30(28)31)52-42-41(48-10)40(47-9)39(46-8)25(5)50-42;1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h17,20,23-32,34-35,37,39-42H,11-16,18-19,21H2,1-10H3;14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t23-,24-,25+,26+,27-,28+,29-,30-,31-,32+,34+,35+,37+,39+,40-,41-,42+;22-,23-,24+,25-,26+,27-,28-,29-,30-,31?,33+,34+,36+,38+,39-,40-,41+/m11/s1 |
| InChI Key | JFLRKDZMHNBDQS-UCQUSYKYSA-N |
Properties
| Appearance | Off-white to Pale Brown Solid |
| Antibiotic Activity Spectrum | Parasites |
| Melting Point | 124-128°C |
| Solubility | Soluble in Chloroform (Slightly, Sonicated), DMF (Slightly), DMSO (Slightly), Methanol (Slightly) |
Reference Reading
1. Pesticide Research and Development: General Discussion and Spinosad Case
Eddie H Chio, Qing X Li J Agric Food Chem. 2022 Jul 27;70(29):8913-8919. doi: 10.1021/acs.jafc.2c03821. Epub 2022 Jul 14.
On average, it has taken approximately 10 years and $250 million to discover and develop one pesticide out of approximately 100 000 compounds. A successful pesticide researcher nowadays needs to be knowledgeable and skillful in multiple disciplines. As a result of the high costs and unique requirements, only a handful of companies in the world can afford to continue pesticide research and development (R/D) in the $70 billion pesticide market. Pesticide R/D is a high-risk yet high-reward business. In this perspective, pesticide R/D is briefly discussed and a case study is used to illustrate how spinosad was discovered and became a successful product, despite the many challenges facing pesticide R/D.
2. Spinosad topical suspension (0.9%): a new topical treatment for scabies
Deepani D Fernando, Katja Fischer Expert Rev Anti Infect Ther. 2022 Sep;20(9):1149-1154. doi: 10.1080/14787210.2022.2099376. Epub 2022 Aug 9.
Introduction: Scabies is a highly contagious skin disease caused by the parasitic mite Sarcoptes scabiei. There is no vaccine and for the past 30 years, the first line treatments have been topical permethrin and oral ivermectin. These drugs target mainly the parasite nervous system, killing only the motile stages. As they lack ovicidal activities, repeat treatments are required to achieve complete cure. Incompliance to repeat treatments causing prolonged drug usage has contributed to emerging drug resistances. In addition, they are not appropriate for all patient categories, specifically for infants and young children or pregnant and breast feeding women. Consequently, new single-dose scabicides are urgently needed. Areas covered: In 2021, spinosad, a drug previously used to treat head lice, was approved by the US FDA as a topical scabies treatment. Here the pharmacology, clinical efficacy, and tolerability of this drug are discussed. Expert opinion: As the first single-dose scabicide, the formulated 0.9% topical Spinosad solution shows significant efficacy, little systemic absorption, and no serious adverse reactions, making it a promising treatment for classical scabies in patients older than four years.
3. The spinosyns, spinosad, spinetoram, and synthetic spinosyn mimics - discovery, exploration, and evolution of a natural product chemistry and the impact of computational tools
Thomas C Sparks, Gary D Crouse, Zoltan Benko, David Demeter, Natalie C Giampietro, William Lambert, Annette V Brown Pest Manag Sci. 2021 Aug;77(8):3637-3649. doi: 10.1002/ps.6073. Epub 2020 Sep 28.
Natural products (NPs) have long been a source of insecticidal crop protection products. Like many macrolide NPs, the spinosyns originated from a soil inhibiting microorganism (Saccharopolyspora spinosa). More than 20 years after initial registration, the spinosyns remain a unique class of NP-based insect control products that presently encompass two insecticidal active ingredients, spinosad, a naturally occurring mixture of spinosyns, and spinetoram, a semi-synthetic spinosyn product. The exploration and exploitation of the spinosyns has, unusually, been tied to an array of computational tools including artificial intelligence (AI)-based quantitative structure activity relationship (QSAR) and most recently computer-aided modeling and design (CAMD). The AI-based QSAR directly lead to the discovery of spinetoram, while the CAMD studies have recently resulted in the discovery and building of a series of synthetic spinosyn mimics. The most recent of these synthetic spinosyn mimics show promise as insecticides targeting lepidopteran insect pests as demonstrated by field studies wherein the efficacy has been shown to be comparable to spinosad and spinetoram. These and a range of other aspects related to the exploration of the spinosyns over the past 30 years are reviewed herein. © 2020 Society of Chemical Industry.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
