SPINOSAD

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SPINOSAD

• John Diaz-Montano, jd325
• Entom 490 - spring 2008

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Outline

• History Discovery and Development
• Properties
• Uses
• Symptoms
• Modes of Action
• Metabolism
• Special Features/Concerns
• References

3
HISTORY Discovery Development

• Lilly research laboratories and Dow Chemical.
  Program to find new and natural products. Soil
  samples all over the world
• 1982
• Soil sample from a Caribbean Island
• 1984
• Microorganisms were isolated, purified and
  sorted
• Cultures were fermented Metabolites
• gt80 screens. One was positive in Aedes aegypti

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HISTORY Discovery Development

• 1985
• A83543. Refermentations confirmed results.
• Oral and contact activity. Southern armyworm
  (Spodoptera eridiana). High priority
• 1986
• New sp. identified as Saccharopolyspora spinosa
• 1988
• First samples and first field tests

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HISTORY Discovery Development

• 1989
• DowElanco formed. Efficacy and toxicology
  testing expanded
• 1991
• Chronic toxicology, environmental fate, global
  field trials
• 1994
• Submitted to EPA

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HISTORY Discovery Development

• 1997
• First registrations
• 1999
• Registration in 24 countries over 100 crops
• 2002
• Registration gt 40 countries
• USA Tracer, Conserve, SpinTor, Success
• World Laser, Credence, Success, Caribstar,
  Boomerang

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NOMENCLATURE
Saccharopolyspora spinosa
saccharo sugar loving polyspora. spinosa spiny
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NOMENCLATURE
Structure of spinosad (spinosyn A spinosyn D)
Spinosyn A R H Empirical formula
C41H65NO10 Spinosyn B R CH3 Empirical
formula C42H67NO10
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PROPERTIES

• Tracer (a.i. spinosad). Trademark of Dow
  AgrowSciences. 1st product in the Naturalyte
  class of insect control products.
• spinosad has the best features insecticides

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PROPERTIES
Physical and chemical properties of spinosad and
its constituents
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PROPERTIES
Degradation in water, pH 7
12
PROPERTIES
Photodegradation on soil surface
Dry soil, 67 did not degrade, half-life 9
days Wet soil, 12 did not degrade, half-life 10
days
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USES
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USES
Spectrum of activity (LC50 ppm) of spinosyn A
against Lepidopteran pests
Highly effective as a broad spectrum insecticide.
(0.04-0.09 lb a.i./A)
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USES

• Spinosad also control beetle larvae and adults.
  Potatoes Colorado potato beetle larvae
  (0.02-0.045 lb ai/A). Ornamentals elm leaf
  beetle larvae and adults at 12.5 ppm and imported
  willow leaf beetle adults
• Spinosad is not very systemic. It can penetrate
  the leaf surface and provide control of
  leafminers Lepidoptera (Phyllonorycter sp. in
  apples and citrus trees), and Diptera (Liriomyza
  sp. in tomatoes, peppers, celery, lettuce and
  ornamentals) at very low doses (0.067-0.09 lb
  ai/A)

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SYMPTOMS

• Flaccidity
• Lack of movement
• No feeding
• Tremors
• Caterpillars mandibles (continuous movement)

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SYMPTOMS
Cockroaches 4-8 h after abdominal injection 2 ?g
of spinosyn A
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MODES OF ACTION
Nicotinic AcetylCholine Receptors and GABA
receptor
How spinosa act on the nAChRs
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MODES OF ACTION
Effects of spinosad on nAChRs and GABA receptors
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METABOLISM

• Dermal exposures in rats for 24 and 120 h
  resulted in only 1 and 2 absorption. After 48 h
  60-80 was eliminated through urine and feces
• Metabolism of spinosyn A was measured in 10
  American cockroaches, P. americana. 1.9 mg of
  spinosyn A .48 h later the nerve cords were
  removed. 38.5 of the radioactivity in the nerve
  cord was spinosyn A

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Special Features/Concerns
Effects on non-target organisms

• Predators
• Beneficial predators found in cotton fields have
  been found to be tolerant to applications of
  spinosad
• Secondary effects on lady beetle and green
  lacewing larvae feeding on aphids treated with
  200 ppm no mortality was observed. While in a
  similar experiment with cypermethrin 100
  mortality

LC50 (24 h) of spinosad on predators
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Special Features/Concerns
Effects on non-target organisms

• Parasitoids
• Spinosad is toxic against bees, wasps, and ants.
  But, toxicity is much lower compared to synthetic
  insecticides
• LC50 for Encarsia formosa (whitefly parasitoid)
  was 29 ppm for spinosad SC while 1.9 ppm for
  cypermethrin
• The wasp parasitoid, Cotesia marginiventris pupae
  in contact with spinosad in doses of 0.045 and
  0.089 lb ai/A showed no reduction in the
  emergence of adult wasps

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Special Features/Concerns
Mammalian toxicity
Acute toxicology of spinosad

• Chronic toxicology oncogenicity, mutagenicity,
  teratology, and neurotoxicity. There was no
  evidence of any adverse health effects

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Special Features/Concerns
Environmental toxicity
Avian and aquatic toxicity
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REFERENCES
History Discovery and Development Sparks T.C,
G.D. Thompson, H.A. Kirst, M.B. Hertlein, J.S.
Mynderse, J.R. Turner and T.V. Worden. 1999.
Fermentation-derived insect control agents - The
Spinosyns. In Biopesticides Use and Delivery
(eds F.R. Hall J.J Menn), Humana Press, New
Jersey, pp. 171-188. Thompson, G.D., K.H.
Michel, R.C. Yao, J.S. Mynderse, C.T. Mosburg,
T.V. Worden, E.H. Chio, T.C. Sparks and S.H.
Hutchins. 1997. The discovery of
Saccharopolyspora spinosa and a new class of
insect control products. Down to Earth 52(1)
1-5. Thompson, G.D., R. Dutton, and T.C. Sparks.
2000. Spinosad a case study an example from a
natural products discovery programme. Pest Manag.
Sci. 56 696-702. Thompson, G.D., S.H. Hutchins,
and T.C. Sparks. 2002. Development of
spinosad?and attributes of?a new class of insect
control products. In E. B. Radcliffe and W. D.
Hutchison eds., Radcliffe's IPM World Textbook.
http//ipmworld.umn.edu, University of Minnesota,
St. Paul, MN. Nomenclature Kirst, H.A., K.H.
Michel, J.W. Martin, L.C. Creemer, E.H. Chio,
R.C.Yao, W.M. Nakatsukasa, L.D. Boeck, J.L.
Occolowitz, J.W. Paschal. J.B. Deeter, N.D.
Jones, and G.D. Thompson. 1991. A83543A-D, unique
fermentation-derived tetracyclic macrolides.
Tetrahedron Letter, 32(37) 4839-4842. Saunders,
D.G., and Bret B.L. 1997. Fate of spinosad in the
environment. Down to Earth 52(1)
14-20. Thompson, G.D., K.H. Michel, R.C. Yao,
J.S. Mynderse, C.T. Mosburg, T.V. Worden, E.H.
Chio, T.C. Sparks and S.H. Hutchins. 1997. The
discovery of Saccharopolyspora spinosa and a new
class of insect control products. Down to Earth
52(1) 1-5.
26
REFERENCES
Properties Bret, B.L., L.L. Larson, J.R.
Schoonover, T.C. Sparks and G.D. Thompson. 1997.
Biological properties of spinosad. Down to Earth
52(1) 6-13. Saunders, D.G., and Bret B.L. 1997.
Fate of spinosad in the environment. Down to
Earth 52(1) 14-20. Thompson, G.D., K.H. Michel,
R.C. Yao, J.S. Mynderse, C.T. Mosburg, T.V.
Worden, E.H. Chio, T.C. Sparks and S.H. Hutchins.
1997. The discovery of Saccharopolyspora spinosa
and a new class of insect control products. Down
to Earth 52(1) 1-5. Thompson, G.D., R. Dutton,
and T.C. Sparks. 2000. Spinosad a case study
an example from a natural products discovery
programme. Pest Manag. Sci. 56
696-702. Uses Bret, B.L., L.L. Larson, J.R.
Schoonover, T.C. Sparks and G.D. Thompson. 1997.
Biological properties of spinosad. Down to Earth
52(1) 6-13. Nolting, S.P., R.M. Huckaba, B.A.
Nead, L.G. Peterson, D.J. Porteous, and P.W.
Borth. 1997. Insect control in cotton with
tracer. Down to Earth 52(1) 21-27. Ruberson, J.
R., 1999. Handbook of Pest Management. Dekker,
New York. Symptoms Bret, B.L., L.L. Larson,
J.R. Schoonover, T.C. Sparks and G.D. Thompson.
1997. Biological properties of spinosad. Down to
Earth 52(1) 6-13. Salgado, V.L. 1998. Studies
on the mode of action of spinosad insect
symptoms and physiological correlates. Pesticide
Biochem. Physiol. 60 91-102.
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REFERENCES
Modes of Action Salgado, V.L, J.L. Sheets, G.B.
Watson, and A.L. Schmidt. 1998. Studies on the
mode of action of spinosad the internal
effective concentration and the concentration
dependence of neural excitation. Pesticide
Biochem. Physiol. 60 103-110. Salgado, V.L.
1997. The modes of action of spinosad and other
insect control products. Down to Earth 52(1)
35-43. Salgado, V.L. 1998. Studies on the mode of
action of spinosad insect symptoms and
physiological correlates. Pesticide Biochem.
Physiol. 60 91-102. Sparks T.C, G.D. Thompson,
H.A. Kirst, M.B. Hertlein, J.S. Mynderse, J.R.
Turner and T.V. Worden. 1999. Fermentation-derived
insect control agents - The Spinosyns. In
Biopesticides Use and Delivery (eds F.R. Hall
J.J Menn), Humana Press, New Jersey, pp.
171-188. Metabolism Salgado, V.L. 1998. Studies
on the mode of action of spinosad insect
symptoms and physiological correlates. Pesticide
Biochem. Physiol. 60 91-102. Salgado, V.L,
J.L. Sheets, G.B. Watson, and A.L. Schmidt. 1998.
Studies on the mode of action of spinosad the
internal effective concentration and the
concentration dependence of neural excitation.
Pesticide Biochem. Physiol. 60 103-110. Dow
AgroSciences. 1997. Spinosad Technical Bulletin.
Dow AgroSciences. 15 p. EPA. 1997. Spinosad
Pesticide Fact Sheet No. HJ 501C. EPA, Office of
Pesticides and Toxic Substances. Special
Features/Concerns Bret, B.L., L.L. Larson, J.R.
Schoonover, T.C. Sparks and G.D. Thompson. 1997.
Biological properties of spinosad. Down to Earth
52(1) 6-13. Peterson, L.G., J.R. Ruberson, R.K.
Sprenkel, J.R. Weeks, M.C. Donahoe, R.H. Smith,
J.S. Swart, D.J. Reid, and G.D. Thompson. 1997.
Tracer Naturalyte insect control and IPM. Down to
Earth 52(1) 28-34 Saunders, D.G., and Bret B.L.
1997. Fate of spinosad in the environment. Down
to Earth 52(1) 14-20. Schoonover, J. R. and
L.L. Larson. 1995. Laboratory activity of
spinosad on non-target beneficial arthropods.
Arthropod Management Tests. 20357.