Spinosad

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Spinosyn A
Spinosyn A.png
Identifiers
CAS number 168316-95-8
PubChem 183094
ChemSpider 16736513 YesY
ChEBI CHEBI:9230 YesY
ChEMBL CHEMBL1615373
ATCvet code QP53BX03
Properties
Molecular formula C41H65NO10
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
Spinosyn D
Spinosyn D.png
Identifiers
CAS number 131929-60-7
PubChem 443059
ChEBI CHEBI:9232 YesY
ATCvet code QP53BX03
Properties
Molecular formula C42H67NO10
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Spinosad insecticide is based on a compound found in the bacterial species Saccharopolyspora spinosa (S. spinosa). The genus of Saccharopolyspora was discovered in 1985 by Lacey and Goodfellow, who described isolates from crushed sugar cane which produce yellowish-pink aerial hyphae, with beadlike chains of spores enclosed in a characteristic hairy sheath.[1] This genus is defined as aerobic, gram-positive, non-acid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a non-operational sugar mill rum still in the Virgin Islands. The spinosyn family of chemical compounds has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose.[2] Spinosad is a relatively non-polar molecule that is not easily dissolved in water.[3] 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.[4] Spinosad insecticide contains a mix of two spinosoids, Spinosyn A, the major component, and Spinosyn D (the minor component), in an approximately 17:3 ratio.[1]

Mode of action[edit]

Spinosad is highly active, by both contact and ingestion, to numerous pests.[5] Spinosad’s overall protective effect varies with pest species and life stage. Spinosad affects certain insect pests only in the adult stage, but can affect other pests at more than one life stage. The pests that are subject to very high rates of mortality as larvae, but not as adults, may gradually be controlled through sustained larval mortality.[5] The mode of action of spinosoid insecticides is via a neural mechanism.[6] 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.[2] Spinosad also has secondary effects as a Ɣ-amino-butyric acid (GABA) neurotransmitter agonist.[2] Spinosad kills insects via hyperexcitation of the insect nervous system.[2] Spinosad so far has proven non cross-resistant to any other known insecticide.[7]

Use[edit]

Spinosad has been used around the world for the control of a variety of insect pests, including Lepidoptera, Diptera, Thysanoptera, Coleoptera, Orthoptera and Hymenoptera, and many others.[8] Spinosad was first registered as a pesticide in the United States for use on crops in 1997.[8] Its labeled use rate is set at 1 ppm (1 mg a.i./kg of grain) and its Maximum Residue Limit (MRL) or tolerance is set at 1.5 ppm. Spinosad’s widespread commercial launch was deferred, awaiting final MRL or tolerance approvals in a few remaining grain-importing countries. Spinosad is considered a natural product, and thus is approved for use in organic agriculture by numerous nations.[5] Two other uses for Spinosad are for pets and humans. Spinosad has recently been used in oral preparations to treat C. felis, the cat flea, in canines and felines; the optimal dose set for canines is reported to be 30 mg/kg.[2]

Trade names include Comfortis and Trifexis® (which also includes milbemycin oxime) (both brands treat adult fleas on pets; the latter also prevents heartworm disease), and Natroba (for human head lice.) It is commonly used to kill thrips and other pests on flowering marijuana plants a few weeks before harvest without harming the flowers or making them harmful if smoked.[9][10][11]

Spinosyn A[edit]

Spinosyn A does not appear to interact directly with known insecticidal-relevant target sites, but rather acts via a novel mechanism.[6] Spinosyn A resembles a GABA antagonist and is comparable to the effect of avermectin on insect neurons.[4] Spinosyn A is highly active against neonate larvae of the tobacco budworm, Heliothis virescens, and is slightly more biologically active than Spinosyn D. In general spinosyns possessing a methyl group at C6 (Spinosyn D-related analogs) tend to be more active and less affected by changes in the rest of the molecule.[7] Spinosyn A is slow to penetrate to the internal fluids of larvae; it is also poorly metabolized once it enters the insect.[7] The apparent lack of Spinosyn A metabolism may contribute to its high level of activity, and may compensate for the slow rate of penetration.[7]

Safety and ecotoxicology[edit]

Spinosad has high efficacy, a broad insect pest spectrum, low mammalian toxicity, and a good environmental profile. This is a unique feature of an insecticide, compared to others that are currently used for the protection of grain products.[5] Spinosad is considered a natural product and approved for use in organic agriculture by numerous national and international certifications.[8] Spinosad residues are highly stable on grains stored in bins, with protection ranging from 6 months to 2 years.[5] Ecotoxicology parameters for Spinosad are for Rat (Rattus norvegicus Bergenhout, 1769)-acute oral: LD50>5000 mg/kg (non-toxic), Rat (Rattus norvegicus Bergenhout, 1769)-acute dermal: LD50>2000 mg/kg (non-toxic), California Quail (Callipepla californica Shaw, 1798)-oral toxicity: LD50>2000 mg/kg (non-toxic), Duck (Anas platyrhynchos domestica Linnaeus, 1758)-dietary toxicity: LC50>5000 mg/kg (non-toxic), Rainbow Trout (Oncorhynchus mykiss Walbaum, 1792): LC50-96h=30,0 mg/l (slightly toxic), Honeybee (Apis mellifera Linnaeus, 1758): LD50=0,0025 mg/bee (highly toxic, if directly sprayed on bees, but dried residues show little toxicity).[12]

However, most tests ignore the cytotoxic (toxicity within the cell) aspects[citation needed]. One unblinded study, run on groups of 10 rats per dose level, which was run using direct oral doses of the commercially prepared insectide and not with pure spinosad, found some biological effects at higher doses, and confirmed that spinosad had much less negative effects than malathion.[13]

Regardless of the above findings, 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. http://toxsci.oxfordjournals.org/content/65/2/276.full . Similarly, rats given 25 mg/kg/day for 24 months did not experience tumors. http://toxsci.oxfordjournals.org/content/65/2/288.full

References[edit]

  1. ^ a b Mertz, Frederick; Raymond C. Yao (Jan 1990). "Saccharopolyspora spinosa sp. nov. Isolated from soil Collected in a Sugar Mill Rum Still". International Journal of Systematic Bacteriology 40 (1): 34–39. 
  2. ^ a b c d e Qiao, Meihua; Daniel E. Snyder, Jeffery Meyer, Alan G. Zimmerman, Meihau Qiao, Sonya J. Gissendanner, Larry R. Cruthers, Robyn L. Slone, Davide R. Young (12 September 2007). "Preliminary Studies on the effectiveness of the novel pulicide, spinosad, for the treatment and control of fleas on dogs". Veterinary Parasitology: 345–351. Retrieved 3 May 2012. 
  3. ^ Crouse, Gary; Thomas C Sparks, Joseph Schoonover, James Gifford, James Dripps, Tim Brue, Larry L Larson, Joseph Garlich, Chris Hatton, Rober L Hill, Thomas V Worden and Jacek G Martynow (27 September 2000). "Recent advances in the chemistry of spinosyns". Pest Manag Sci: 177–185. 
  4. ^ a b Watson, Gerald (31 May 2001). "Actions of Insecticidal Spinosyns on gama-Aminobutyric Acid Responses for Small-Diameter Cockroach Neurons". Pesticide Biochemistry and Physiology 71: 20–28. 
  5. ^ a b c d e Hertlein, Mark; Gary D. Thompson, Bhadriraju Subramanyam, Christos G. Athanassiou (12 January 2011). "Spinosad: A new natural product for stored grain protection". stored products 47: 131–146. Retrieved 3 May 2012. 
  6. ^ a b Orr, Nailah; Andrew J. Shaffner, Kimberly Richey, Gary D. Crouse (30 April 2009). "Novel mode of action of spinosad: Receptor binding studies demonstrating lack of interaction with known insecticidal target sites". Pesticide Biochemistry and Physiology 95: 1–5. 
  7. ^ a b c d Sparks, Thomas; Gary D crouse, Gregory Durst (30 March 2001). "Natural products as insecticides: the biology, biochemistry and quantitative structure-activity relationships of spinosyns and spinosoids". pest manag sci 57. 
  8. ^ a b c Sparks, Thomas; James E. Dripps, Gerald B Watson, Doris Paroonagian (6 November 2012). "Resistance and cross-resistance to the spinosyns- A review and analysis". Pesticide Biochemistry and Physiology: 1–10. Retrieved 17 November 2011. 
  9. ^ "Spinosad - brand name list from". Drugs.com. Retrieved 2012-10-20. 
  10. ^ "UC Davis School of Vet Med:". Vetmed.ucdavis.edu. Retrieved 2012-10-20. 
  11. ^ "Safer Flea Control | Insects in the City". Citybugs.tamu.edu. Retrieved 2012-10-20. 
  12. ^ "Codling Moth and Leafroller Control Using Chemicals" (PDF). Entomology.tfrec.wsu.edu. Retrieved 2012-10-20. 
  13. ^ "Cytogenetic and Hormonal Alteration in Rats Exposed to Recommended "Safe Doses" of Spinosad and Malathion Insecticides" (PDF). Fspublishers.org. Retrieved 2014-01-08.