Spinosad
Spinosyn A
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Spinosyn D
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Identifiers | |
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3D model (
JSmol ) |
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ChEBI |
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ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.103.254 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C41H65NO10 (A) C42H67NO10 (D) | |
Molar mass | 731.968 g·mol−1 (A) 745.995 g·mol−1 (D) |
Pharmacology | |
QP53BX03 (WHO )
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by mouth
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Legal status | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Clinical data | |
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ECHA InfoCard | 100.103.254 |
Spinosad is an
Spinosad is a novel mode-of-action insecticide derived from a family of natural products obtained by fermentation of S. spinosa. Spinosyns occur in over 20 natural forms, and over 200 synthetic forms (spinosoids) have been produced in the lab.[7] Spinosad contains a mix of two spinosoids, spinosyn A, the major component, and spinosyn D (the minor component), in a roughly 17:3 ratio.[4]
Mode of action
Spinosad is highly active, by both contact and ingestion, in numerous insect species.[8] Its overall protective effect varies with insect species and life stage. It affects certain species only in the adult stage, but can affect other species at more than one life stage. The species subject to very high rates of mortality as larvae, but not as adults, may gradually be controlled through sustained larval mortality.[8] The mode of action of spinosoid insecticides is by a neural mechanism.[9] The spinosyns and spinosoids have a novel mode of action, primarily targeting binding sites on nicotinic acetylcholine receptors (nAChRs) of the insect nervous system that are distinct from those at which other insecticides have their activity. Spinosoid binding leads to disruption of acetylcholine neurotransmission.[5] Spinosad also has secondary effects as a γ-amino-butyric acid (GABA) neurotransmitter agonist.[5] It kills insects by hyperexcitation of the insect nervous system.[5] Spinosad has proven not to cause cross-resistance to any other known insecticide.[10]
Uses
Spinosad has been used around the world for the control of a variety of insect pests, including
Spinosad is sold under the brand names, Comfortis, Trifexis, and Natroba.[12][13] Trifexis also includes milbemycin oxime. Comfortis and Trifexis brands treat adult fleas on pets; the latter also prevents heartworm disease. Natroba is sold for treatment of human head lice. Spinosad is also commonly used to kill thrips.[14][15][16]
Comfortis and Trifexis were withdrawn in the European Union.[17][18]
Spinosyn A
Spinosyn A does not appear to interact directly with known insecticidal-relevant target sites, but rather acts via a novel mechanism.
Resistance
Spinosad resistance has been found in
Safety and ecotoxicology
Spinosad has high efficacy, a broad insect pest spectrum, low mammalian toxicity, and a good environmental profile, a unique feature of the insecticide compared to others currently used for the protection of grain products.[8] It is regarded as natural product-based, and approved for use in organic agriculture by numerous national and international certifications.[11] Spinosad residues are highly stable on grains stored in bins, with protection ranging from 6 months to 2 years.[8][clarification needed] Ecotoxicology parameters have been reported for spinosad, and are:[26]
- in rat (Rattus norvegicus (Bergenhout, 1769)), acute oral: LD50>5000 mg/kg (nontoxic)
- in rat (R. norvegicus), acute dermal: LD50 >2000 mg/kg (nontoxic)
- in California quail (Callipepla californica(Shaw, 1798)), oral toxicity: LD50 >2000 mg/kg (nontoxic)
- in duck (Anas platyrhynchos domestica(Linnaeus, 1758)), dietary toxicity: LC50 >5000 mg/kg (nontoxic)
- in rainbow trout (Oncorhynchus mykiss (Walbaum, 1792)), LC50-96h = 30.0 mg/L (slightly toxic)
- in honeybee (Apis mellifera(Linnaeus, 1758)), LD50 = 0.0025 mg/bee (highly toxic if directly sprayed on and of dried residues).
Chronic exposure studies failed to induce tumor formation in rats and mice; mice given up to 51 mg/kg/day for 18 months resulted in no tumor formation.[27] Similarly, administration of 25 mg/kg/day to rats for 24 months did not result in tumor formation.[28]
References
- ^ "Natroba- spinosad suspension". DailyMed. U.S. National Library of Medicine. 28 April 2021. Retrieved 1 July 2023.
- ^ "Spinosad suspension". DailyMed. U.S. National Library of Medicine. 31 May 2023. Retrieved 1 July 2023.
- ^ "Comfortis- spinosad tablet, chewable". DailyMed. U.S. National Library of Medicine. 1 July 2021. Retrieved 1 July 2023.
- ^ .
- ^ PMID 17980490.
- PMID 11455648.
- ^ .
- ^ .
- ^ .
- ^ PMID 11695182.
- ^ . Retrieved 17 November 2011.
- ^ "Spinosad international brands". Drugs.com. 3 January 2020. Retrieved 30 January 2020.
- ^ "Spinosad US brands". Drugs.com. 3 January 2020. Retrieved 30 January 2020.
- ^ "Spinosad - brand name list from". Drugs.com. Retrieved 20 October 2012.
- ^ Bethke JA, Dreistadt SH, Varela LG, Phillips PA, O'Donnell CA (May 2014). Thripsm (PDF). University of California Statewide Integrated Pest Management Program. UCANR Publication. (Report). Integrated Pest Management for Home Gardeners and Landscape Professionals.
- ^ Merchant M. "Safer Flea Control | Insects in the City". Texas A&M AgriLife Extension Service. Retrieved 20 October 2012.
- ^ "Comfortis EPAR". European Medicines Agency. 26 June 2023. Retrieved 3 July 2023.
- ^ "Trifexis EPAR". European Medicines Agency. 5 November 2020. Retrieved 3 July 2023.
- S2CID 26611971.
- ^ PMID 23109262.
- PMID 15307676.
- S2CID 182038998.
- S2CID 25560262.)
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: CS1 maint: DOI inactive as of January 2024 (link - PMID 17665366.
- ^ See for continued updates: Mota-Sanchez D, Wise JC, et al. (Insecticide Resistance Action Committee). "Arthropod Pesticide Resistance Database". Michigan State University.
- ^ Brunner JF. "Codling Moth and Leafroller Control Using Chemicals" (PDF). Tree Fruit Research and Extension Center. Washington State University. Archived from the original (PDF) on 3 August 2003. Retrieved 20 October 2012.
- PMID 11812932.
- PMID 11812933.
Further reading
- Mayes MA, Thompson GD, Husband B, Miles MM (2003). "Spinosad toxicity to pollinators and associated risk". Reviews of Environmental Contamination and Toxicology. 179: 37–71. PMID 15366583.