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(1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata

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Abstract

Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid–related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography–mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(−)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid–related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.

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Acknowledgments

NMR spectrometry analyses were carried out with the support of the Advanced Analysis Center at the National Agriculture and Food Research Organization. We acknowledge a grant-in-aid for scientific research from the Japan Society for the Promotion of Science (no. 16 K08103) to JT.

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  1. National Agriculture and Food Research Organization, 3-1-3 Kannondai, Tsukuba, Ibaraki, 305-8604, Japan

    Jun Tabata & Ryoko T. Ichiki

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  1. Jun Tabata
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  2. Ryoko T. Ichiki
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Correspondence to Jun Tabata.

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Tabata, J., Ichiki, R.T. (1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata . J Chem Ecol 43, 745–752 (2017). https://doi.org/10.1007/s10886-017-0879-z

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  • DOI: https://doi.org/10.1007/s10886-017-0879-z

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