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Related Experiment Video

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Development of Metarhizium anisopliae as a Mycoinsecticide: From Isolation to Field Performance
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Pro-insecticidal approach towards increasing in planta activity.

Lawrence C Creemer1, Natalie C Giampietro1, William Lambert1

  • 1Dow AgroSciences, Discovery Research, Indianapolis, IN, USA.

Pest Management Science
|July 15, 2016
PubMed
Summary

Clonidine analogs show insecticidal promise, but a prodrug strategy failed to improve translaminar movement in plants. Metabolism and vacuole trapping likely hindered pesticide availability to target insects.

Keywords:
adrenergicgreen peach aphidmetabolismprodrugtranslaminarvacuole trappingwhitefly

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Area of Science:

  • Agricultural Science
  • Entomology
  • Medicinal Chemistry

Background:

  • Investigated adrenergic mode of action for novel insecticide development.
  • Tested clonidine-related analogs against Myzus persicae and Bemisia tabaci.
  • Explored prodrug approach to overcome vacuole-trapping mechanism limiting clonidine analog translation.

Purpose of the Study:

  • To assess the insecticidal potential of clonidine analogs.
  • To develop and evaluate a prodrug strategy to enhance pesticide translocation in plants.
  • To understand the metabolic fate and translocation barriers of clonidine-based insecticides.

Main Methods:

  • Synthesized a prodrug of a known open-chain clonidine analog.
  • Assessed insecticidal activity against M. persicae and B. tabaci, and translocation in cotton.
  • Conducted metabolic studies to identify metabolites and understand in planta degradation pathways.

Main Results:

  • Clonidine and its analogs demonstrated insecticidal activity against key agricultural pests.
  • The developed prodrug exhibited reduced pKa, increased lipophilicity, and activity against target insects but failed to translocate effectively in cotton.
  • Metabolic studies revealed rapid conversion of the prodrug to the parent compound and subsequently to a vacuole-trapped oxazoline analog.

Conclusions:

  • Adrenergic compounds like clonidine analogs hold potential as insecticides.
  • The prodrug approach was unsuccessful in overcoming the vacuole-trapping barrier and improving translaminar movement.
  • Faster metabolism and vacuole trapping than translaminar flow likely reduced pesticide bioavailability, limiting efficacy in planta.