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Biocidal Compounds from Mentha sp. Essential Oils and Their Structure-Activity Relationships.

Athanasios C Kimbaris1, Azucena González-Coloma2, Maria Fe Andrés2

  • 1Laboratory of Chemistry & Biochemistry, Department of Agricultural Development Democritus, University of Thrace, 193, Pantazidou str, 68200, N. Orestiada, Greece.

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Summary

Greek Mentha essential oils and their components show potent insecticidal, nematicidal, and phytotoxic activities. Structural modifications of the p-menthane skeleton, particularly epoxide presence, are key for developing natural crop protectants.

Keywords:
AntifeedantEpoxideNematicidalStructure-activity relationship (SAR)p-Menthane monoterpene

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Area of Science:

  • Agricultural Science
  • Organic Chemistry
  • Entomology

Background:

  • Essential oils from Greek Mentha species exhibit diverse chemical profiles.
  • Two populations of Mentha pulegium were characterized by piperitone and pulegone.
  • Mentha spicata essential oil contained piperitenone epoxide, piperitone epoxide, and carvone.

Purpose of the Study:

  • To evaluate the bioactivities of Mentha essential oils and their components against agricultural pests and plants.
  • To investigate structure-activity relationships of p-menthane derivatives, including novel epoxides.
  • To explore the potential of these compounds as natural crop protectants.

Main Methods:

  • Chemical characterization of essential oils from Mentha species.
  • Bioassays against insect pests (Leptinotarsa decemlineata, Spodoptera littoralis, Myzus persicae) and nematodes (Meloidogyne javanica).
  • Phytotoxicity tests on plant germination and growth (Lactuca sativa, Lolium perenne, Solanum lycopersicum).
  • Structure-activity relationship studies involving semi-synthetic derivatives.

Main Results:

  • Piperitenone and piperitone epoxide demonstrated antifeedant effects on Leptinotarsa decemlineata.
  • Piperitone epoxide and pulegone affected Spodoptera littoralis.
  • Piperitenone epoxide was the most potent nematicidal agent, followed by piperitone epoxide, piperitenone, and carvone.
  • Piperitenone epoxide significantly impacted germination and growth of Solanum lycopersicum and Lolium perenne.
  • Carvone epoxide also inhibited Lolium perenne root and leaf growth.

Conclusions:

  • The presence of a C(1) epoxide in p-menthane derivatives confers strong antifeedant, nematicidal, and phytotoxic properties.
  • Essential oils from Greek Mentha species and their derivatives show promise as natural crop protection agents.
  • Structural modifications of the p-menthane skeleton can lead to the development of new, effective agrochemicals.