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Spinosad

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Spinosyns

Spinosyn A

Spinosyn D
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.103.254 Edit this at Wikidata
  • 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 checkY
    Key: JFLRKDZMHNBDQS-SGSTVUCESA-N checkY
  • (A): InChI=1/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
    Key: JFLRKDZMHNBDQS-SGSTVUCEBI
Properties
C41H65NO10 (A)
C42H67NO10 (D)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus of Saccharopolyspora was discovered in 1985 in isolates from crushed sugar cane which produce yellowish-pink aerial hyphae, with bead-like 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. Spinosad is a mixture of chemical compounds in the spinosyn family that 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 relatively non-polar and 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 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

Spinosad is highly active, by both contact and ingestion, to numerous insect species.[5] Spinosad’s overall protective effect varies with insect species and life stage. Spinosad affects certain species only in the adult stage, but can affect other species at more than one life stage. The species 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

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.[9][10][11]

Spinosyn A

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

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 that are currently used for the protection of grain products.[5] Spinosad is regarded as natural products-based, 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][clarification needed][vague]

Ecotoxicology parameters have been reported for Spinosad, and are as follows:[12]

  • in Rat (Rattus norvegicus Bergenhout, 1769), acute oral: LD50>5000 mg/kg (non-toxic),
  • in Rat (Rattus norvegicus Bergenhout, 1769), acute dermal: LD50>2000 mg/kg (non-toxic),
  • in California Quail (Callipepla californica Shaw, 1798), oral toxicity: LD50>2000 mg/kg (non-toxic),
  • in Duck (Anas platyrhynchos domestica Linnaeus, 1758), dietary toxicity: LC50>5000 mg/kg (non-toxic),
  • in Rainbow Trout (Oncorhynchus mykiss Walbaum, 1792), LC50-96h=30.0 mg/l (slightly toxic), and
  • in Honeybee (Apis mellifera Linnaeus, 1758), LD50=0.0025 mg/bee (highly toxic if directly sprayed on, little toxicity of dried residues).

An unblinded study performed on groups of 10 rats per dose level run using direct oral doses of commercially prepared insectide found some effects at higher doses, but confirmed that spinosad had much less negative effects than malathion.[13][better source needed] 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.[14] Similarly, administration of 25 mg/kg/day to rats for 24 months did not result in tumor formation. [15]

References

  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. doi:10.1099/00207713-40-1-34. {{cite journal}}: |access-date= requires |url= (help); Check date values in: |year= / |date= mismatch (help)
  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. doi:10.1016/j.vetpar.2007.09.011.
  3. ^ Crouse, Gary (27 September 2000). "Recent advances in the chemistry of spinosyns". Pest Manag Sci: 177–185. {{cite journal}}: |access-date= requires |url= (help); Check date values in: |year= / |date= mismatch (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  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. doi:10.1006/pest.2001.2559. {{cite journal}}: |access-date= requires |url= (help)
  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. doi:10.1016/j.jspr.2011.01.004. 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. doi:10.1016/j.pestbp.2009.04.009.
  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. {{cite journal}}: |access-date= requires |url= (help)
  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. ^ S.A. Mansour, A.H. Mossa & T.M. Heikal, 2008, Cytogenetic and hormonal alteration in rats exposed to recommended “safe doses” of spinosad and malathion insecticides. Int. J. Agri. Biol. 10: 9–14, see [1], accessed 3 June 2014.
  14. ^ "Spinosad Insecticide: Subchronic and Chronic Toxicity and Lack of Carcinogenicity in CD-1 Mice". Toxsci.oxfordjournals.org. Retrieved 2015-03-08.
  15. ^ "Spinosad Insecticide: Subchronic and Chronic Toxicity and Lack of Carcinogenicity in Fischer 344 Rats". Toxsci.oxfordjournals.org. Retrieved 2015-03-08.
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