Chemistry of the pheromones of mealybug and scale insects.

This article comprehensively reviews the syntheses of all known sex pheromones of scales and mealybugs, describes how they were identified, and how the synthetic pheromones are used in insect management.

• Publication year

  2015

• Venue

  Natural product reports (Print)

• Publication date

  2015-06-26

• Fields of study

  Biology, Medicine, Chemistry, Environmental Science

• Identifiers
  DOI 10.1039/c4np00143ePMID 25793226
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Deployment of mating disruption dispensers before and after first seasonal male flights for the control of Aonidiella aurantii in citrus

  2015cited by this paper
• Identification of the Major Sex Pheromone Component of the Scale Insect, Aulacaspis murrayae Takahashi

  2014cited by this paper
• Syntheses and determination of absolute configurations and biological activities of the enantiomers of the longtailed mealybug pheromone.

  2013cited by this paper
• A convenient route for synthesis of 2-isopropyliden-5-methyl-4-hexen-1-yl butyrate, the sex pheromone of Planococcus kraunhiae (Hemiptera: Pseudococcidae), by use of β,γ to α,β double-bond migration in an unsaturated aldehyde

  2013cited by this paper
• Pest management with natural products

  2013cited by this paper
• Intramolecular carbolithiation as a route to a sterically congested cyclopentene: synthesis of the longtailed mealybug pheromone.

  2013cited by this paper
• Efficacy of pheromone mating disruption for vine mealybug control

  2013cited by this paper
• Synthesis of a Sex Pheromone of the Longtailed Mealybug, Pseudococcus longispinus

  2013cited by this paper
• Mating disruption for the control of Aonidiella aurantii Maskell (Hemiptera: Diaspididae) may contribute to increased effectiveness of natural enemies.

  2012cited by this paper
• Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: application to the synthesis of the Californian red scale beetle pheromone.

  2012cited by this paper
• A new class of mealybug pheromones: a hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi

  2012cited by this paper
• Identification of the sex pheromone of the mealybug Dysmicoccus grassii Leonardi.

  2012cited by this paper
• Developing Detection and Monitoring Strategies for Planococcus minor (Hemiptera: Pseudococcidae)

  2012cited by this paper
• Identification of the Sex Pheromone of the Invasive Scale Acutaspis albopicta (Hemiptera: Diaspididae), Arriving in California on Shipments of Avocados from Mexico

  2012cited by this paper
• Reproductive Biology of Three Cosmopolitan Mealybug (Hemiptera: Pseudococcidae) Species, Pseudococcus longispinus, Pseudococcus viburni, and Planococcus ficus

  2011cited by this paper
• Pheromone-Baited Traps for Assessment of Seasonal Activity and Population Densities of Mealybug Species (Hemiptera: Pseudococcidae) in Nurseries Producing Ornamental Plants

  2011cited by this paper
• Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor

  2011cited by this paper
• Chirality and Bioactivity of the Sex Pheromone of Madeira Mealybug (Hemiptera: Pseudococcidae)

  2011cited by this paper
• The Absolute Configuration of the Sex Pheromone of the Citrophilous Mealybug, Pseudococcus calceolariae

  2011cited by this paper
• Mating disruption field trials to control the vine mealybug Planococcus ficus

  2011cited by this paper
• Improved Synthesis of the Pheromoneof the Longtailed Mealybug

  2010cited by this paper
• Mating disruption of California red scale, Aonidiella aurantii Maskell (Homoptera: Diaspididae), using biodegradable mesoporous pheromone dispensers.

  2010cited by this paper
• Enantiospecific synthesis of sex pheromone of the obscure mealybug from pantolactone via tandem conjugate addition/cyclization

  2010cited by this paper
• Pheromone Synthesis. Part 139. Enzymatic Preparation of (2S,3R)-4- Acetoxy-2,3-epoxybutan-1-ol and Its Conversion to the Epoxy Pheromones of the Gypsy Moth and the Ruby Tiger Moth.

  2010cited by this paper
• Chrysanthemyl 2-acetoxy-3-methylbutanoate : the sex pheromone of the citrophilous mealybug Pseudococcus calceolariae

  2010cited by this paper
• Synthesis and bioassay of racemic and chiral trans-alpha-necrodyl isobutyrate, the sex pheromone of the grape mealybug Pseudococcus maritimus.

  2010cited by this paper
• Sex pheromone of the longtailed mealybug: a new class of monoterpene structure.

  2009cited by this paper
• The first account of the mating disruption technique for the control of California red scale, Aonidiella aurantii Maskell (Homoptera: Diaspididae) using new biodegradable dispensers.

  2009cited by this paper
• The Meyer-Schuster rearrangement for the synthesis of alpha,beta-unsaturated carbonyl compounds.

  2009cited by this paper
• Synthesis of the pheromone of the longtailed mealybug, a sterically congested, irregular monoterpenoid.

  2009cited by this paper
• Identification and Synthesis of the Sex Pheromone of the Madeira Mealybug, Phenacoccus Madeirensis Green

  2009cited by this paper
• Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling.

  2008cited by this paper
• Identification of a sex pheromone component of the Japanese mealybug, Planococcus kraunhiae (Kuwana)

  2008cited by this paper
• Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor

  2008cited by this paper
• Enantioselective synthesis of a mealybug pheromone with an irregular monoterpenoid skeleton.

  2008cited by this paper
• Determination of the absolute configuration of the sex pheromone of the obscure mealybug by vibrational circular dichroism analysis.

  2008cited by this paper
• Identification and Synthesis of the Sex Pheromone of the Passionvine Mealybug, Planococcus minor (Maskell)

  2007cited by this paper
• Synthetic Approach towards the Sex Pheromone of the Female Oleander Scale Aspidiotus Nerii

  2007cited by this paper
• DEVELOPMENT OF TRAPPING METHODS WITH A SYNTHETIC SEX PHEROMONE OF THE PINK HIBISCUS MEALYBUG, MACONELLICOCCUS HIRSUTUS (HEMIPTERA: PSEUDOCOCCIDAE)

  2007cited by this paper
• trans-α-Necrodyl isobutyrate, the sex pheromone of the grape mealybug, Pseudococcus maritimus

  2007cited by this paper
• Synthesis of the sex pheromone of the obscure mealybug, the first example of a new class of monoterpenoids

  2007cited by this paper
• A convenient resolution of racemic lavandulol through lipase-catalyzed acylation with succinic anhydride: simple preparation of enantiomerically pure (R)-lavandulol

  2006cited by this paper
• Pheromone-Based Mating Disruption of Planococcus ficus (Hemiptera: Pseudococcidae) in California Vineyards

  2006cited by this paper
• Novel synthesis of Planococcus citri pheromone

  2006cited by this paper
• Olfactory discrimination among sex pheromone stereoisomers: chirality recognition by pink hibiscus mealybug males.

  2006cited by this paper
• Pheromone-based mating disruption of Planococcus ficus (Hemiptera: Pseudococcidae) in California vineyards.

  2006cited by this paper
• New controls investigated for vine mealybug

  2006cited by this paper
• Total synthesis of (±)-herbertenediol

  2006cited by this paper
• Enantioselective synthesis of the female sex pheromone of the pink hibiscus Mealybug, Maconellicoccus hirsutus.

  2005cited by this paper
• Sex Pheromone of the Female Pink Hibiscus Mealybug, Maconellicoccus hirsutus (Green) (Homoptera: Pseudococcidae): Biological Activity Evaluation

  2005cited by this paper
• (2,3,4,4-Tetramethylcyclopentyl)Methyl Acetate, a Sex Pheromone from the Obscure Mealybug: First Example of a New Structural Class of Monoterpenes

  2005cited by this paper
• Enzymatic transesterification of racemic lavandulol: preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate

  2004cited by this paper
• Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.

  2004cited by this paper
• Synthesis of the female sex pheromone of the citrus mealybug, Planococcus citri.

  2004cited by this paper
• Sex pheromone of the citrus mealybug Planococcus citri: synthesis and optimization of trap parameters.

  2004cited by this paper
• Monitoring Planococcus ficus in South African vineyards with sex pheromone-baited traps

  2004cited by this paper
• Chiral synthesis of maconelliol: a novel cyclobutanoid terpene alcohol from pink hibiscus mealybug, Maconellicoccus hirsutus

  2004cited by this paper
• Identification of the sex pheromone of the yellow scale

  2004cited by this paper
• Synthesis of the Sex Pheromone of the Citrus Mealybug, Pseudococcus cryptus

  2003cited by this paper
• Sex Pheromone of the Vine Mealybug, Planococcus ficus in Israel: Occurrence of a Second Component in a Mass-Reared Population

  2003cited by this paper
• ‘Me2CuLi·TMSCl in CH2Cl2’. The most powerful methylating agent for sterically congested α,β-enoates

  2003cited by this paper
• Identification of a Sex Pheromone Component of Pseudococcus cryptus

  2003cited by this paper
• Development and Optimization of Methods for Using Sex Pheromone for Monitoring the Mealybug Planococcus ficus (Homoptera: Pseudococcidae) in California Vineyards

  2002cited by this paper
• Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus

  2001cited by this paper
• Studies on the alkylation of 3-methyl-3-buten-1-ol dianion: an efficient synthesis of 3-methylene-1-alkanols including a San Jose scale sex pheromone.

  2001cited by this paper
• Studies on the alkylation of 3-methyl-3-buten-1-ol dianion: an efficient synthesis of 3-methylene-1-alkanols including a San Jose scale sex pheromone.

  2001cited by this paper
• Enzyme-assisted enantioselective synthesis of natural (-)-beta-necrodol and its enantiomer.

  2001cited by this paper
• Enzyme-catalyzed synthesis and absolute configuration of (1S,2R,5S)- and (1R,2S,5R)-2-(1-hydroxyethyl)-1-(methoxymethyloxyethyl)cyclobutane-1-carbonitrile, key intermediates for the preparation of chiral cyclobutane-containing pheromones

  2000cited by this paper
• Pheromones of non-lepidopteran insects associated with agricultural plants . Edited by J. Hardie and A.K. Minks. (Wallingford: CABI Publishing, 1999). 480 pp. Hard cover £75.00 (US$140.00). ISBN 0 85199 345 1.

  2000cited by this paper
• Sex pheromone of yellow scale, Aonidiella citrina (Homoptera: Diaspididae): Evaluation as an IPM tactic

  2000cited by this paper
• Pheromonal and Kairomonal Activities Can Be Separated: Synthesis and Bioactivity Studies of Pine Bast Scale Sex Pheromones and Their Analogues

  2000cited by this paper
• SYNTHESES OF CYCLOBUTANE DERIVATIVES : TOTAL SYNTHESIS OF (+) AND (-) ENANTIOMERS OF THE OLEANDER SCALE ASPIDIOTUS NERII SEX PHEROMONE

  1999cited by this paper
• FIRST TOTAL SYNTHESIS OF THE SEX PHEROMONE OF THE OLEANDER SCALE ASPIDIOTUS NERII : AN UNUSUAL SESQUITERPENIC FUNCTIONALIZED CYCLOBUTANE

  1999cited by this paper
• Pheromones of Non-Lepidopteran Insects Associated with Agricultural Plants

  1999cited by this paper
• Sex pheromone of the oleander scale, Aspidiotus nerii: structural characterization and absolute configuration of an unusual functionalized cyclobutane.

  1998cited by this paper
• Concise Synthesis of a Racemic and Diastereomeric Mixture of the Sex Pheromones of Matsucoccus Pine Scales

  1997cited by this paper
• Diastereoselective Protonation of Chiral Enolates with Chelating Proton Donors under Reagent Control: Scope, Mechanism, and Applications†

  1997cited by this paper
• Enzymatic synthesis of (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale.

  1996cited by this paper
• Molecular identification of six species of scale insects (Quadraspidiotus sp.) by RAPD‐PCR: assessing the field‐specificity of pheromone traps

  1995cited by this paper
• Pheromone synthesis, CLXXI. A new synthesis of (2E,4E,6R10R)‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one (matsuone), the primary component of the sex pheromone of three Matsucoccus pine bast scales

  1995cited by this paper
• Chirality of israeli pine bast scale,Matsucoccus josephi (homoptera: Matsucoccidae) sex pheromone

  1995cited by this paper
• Synthesis and the determination of the absolute configuration of matsuone, sex pheromone of female Matsucoccus pine scales

  1995cited by this paper
• Efficient Synthesis of the Aonidiella aurantii (Mask.) Sex Pheromone Component: (3S,6RS)-3-Methyl-6-(1-Methylethenyl)-9-decenyl Acetate

  1995cited by this paper
• Syntheses of the female sex pheromones of Matsucoccus pine scales using the [2,3]-wittig rearrangement of a bisallylic tertiary ether

  1995cited by this paper
• Field response of maritime pine scale,Matsucoccus feytaudi duc. (Homoptera: Margarodidae), to synthetic sex pheromone stereoisomers

  1994cited by this paper
• A New Synthesis of Solanone.

  1994cited by this paper
• Facile Preparation of Conjugated Dienes from Allylic Alcohols

  1994cited by this paper
• Pheromone Synthesis, CLXV. A New Synthesis of (3S,7R,8E,10E)‐3,7,9‐Trimethyl‐8,10‐dodecadien‐6‐one, the Major Component of the Sex Pheromone of the Maritime Pine Scale

  1994cited by this paper
• A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX2-TiCl4-Zn Systems by Addition of Lead

  1994cited by this paper
• Pheromone synthesis. Part 166. Synthesis of (2E,5R,6E,8E)-5,7-dimethyldeca-2,6,8-trien-4-one, the major component of the sex pheromone of the Israeli pine bast scale, and its antipode

  1994cited by this paper
• Substituent Effects and Complexation Phenomena in the Diastereoselective Protonation of Chiral Enolates

  1994cited by this paper
• Synthesis and field bioassay of the Israeli pine bast scale, Matsucoccus josephi, female sex pheromone

  1993cited by this paper
• [3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 12. synthesis of (−)-yellow scale pheromone☆

  1993cited by this paper
• Enantioselective synthesis of all four stereoisomers of (2E, 4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the sex pheromone of Matsucoccus pine bast scale

  1993cited by this paper
• Identification of the female sex pheromone of the Israeli pine bast scale Matsucoccus josephi.

  1993cited by this paper
• Vitamin‐B12‐Catalyzed C,C‐Bond Formation. Synthesis of a california red scale pheromone

  1993cited by this paper
• The synthesis of the isomeric components of San Jose scale pheromone — an illustration of a stereospecific synthesis of trisubstituted alkenes

  1993cited by this paper
• Pheromone synthesis, CLV. Synthesis of (2E,4E,6R,10R)-4,6,10,12-Tetramethyl-2,4-tridecadien-7-one (matsuone) – the Primary Component of the Sex Pheromone of Three Matsucoccus Pine Bast Scales – and its Antipode

  1993cited by this paper
• Pheromone Synthesis, CXLIX. Synthesis of (2E,4E,6R,10S)‐4,6,10‐Trimethyl‐2,4‐dodecadien‐7‐one – the Major Component of the Sex Pheromone of the Maritime Pine Scale (Matsucoccus feytaudi) – and its Three Stereoisomers

  1993cited by this paper
• [3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 9. total synthesis of (±)-yellow scale pheromone via 10-membered thiolcarbonate

  1993cited by this paper

• Identification of the Sex Pheromone of the Macadamia Felted Coccid, Acanthococcus Ironsidei (Hemiptera: Eriococcidae)

  2026cites this paper
• Comparative Antennal Transcriptome Analysis of Phenacoccus solenopsis and Expression Profiling of Candidate Odorant Receptor Genes

  2025cites this paper
• Efficient accumulation of new irregular monoterpene malonyl glucosides in Nicotiana benthamiana achieved by co-expression of isoprenyl diphosphate synthases and substrate-producing enzymes

  2025cites this paper
• Sex Pheromone of the Papaya Mealybug

  2025cites this paper
• Interactions of Opuntia ficus-indica with Dactylopius coccus and D. opuntiae (Hemiptera: Dactylopiidae) through the Study of Their Volatile Compounds

  2024cites this paper
• Differential pheromone profile as a contributor to premating isolation between two sympatric sibling fruit fly species

  2024cites this paper
• Transcriptome-informed identification and characterization of Planococcus citri cis- and trans-isoprenyl diphosphate synthase genes

  2024cites this paper
• Identification and characterisation of Planococcus citri cis- and trans-isoprenyl diphosphate synthase genes, supported by short- and long-read transcriptome data

  2023influential citation
• Assessment of tobacco (Nicotiana tabacum) and N. benthamiana as biofactories of irregular monoterpenes for sustainable crop protection

  2023cites this paper
• Can Pheromones Contribute to Phylogenetic Hypotheses? A Case Study of Chrysomelidae

  2023cites this paper
• Assessment of tobacco and N. benthamiana as biofactories of irregular monoterpenes for sustainable crop protection

  2023cites this paper
• Recent advances in the synthesis of insect pheromones: an overview from 2013 to 2022.

  2023cites this paper
• Sex Pheromone of the Azalea Mealybug With a Non-Terpene Structure

  2022cites this paper
• Genetic Basis Underlying Structural Shift of Monoterpenoid Pheromones in Mealybugs

  2022cites this paper
• The mass spectrometric fragmentation mechanisms of catenulane and isocatenulane diterpenes.

  2021cites this paper
• Concise Stereoselective Synthesis of β-Hydroxy-γ-lactones: (4R,5R)-4-Hydroxy-γ-decalactone from the Japanese Orange Fly and Enantiomers of Arachnid Harvestmen Isolates.

  2021cites this paper
• Production of Volatile Moth Sex Pheromones in Transgenic Nicotiana benthamiana Plants

  2021cites this paper
• Engineering of a Plant Isoprenyl Diphosphate Synthase for Development of Irregular Coupling Activity

  2021cites this paper
• The Chemistry of Insect Pheromones

  2020cites this paper
• The characteristic smell emitted from two scale insects, Ceroplastes japonicus and Ceroplastes rubens

  2020cites this paper
• Sex Pheromones of Mealybugs: Implications for Evolution and Application

  2020cites this paper
• Sex pheromone of the aerial root mealybug, Pseudococcus baliteus: A unique monoterpenoid containing an α-hydroxyketone moiety

  2020cites this paper
• Sex pheromone of a coccoid insect with sexual and asexual lineages: fate of an ancestrally essential sexual signal in parthenogenetic females

  2017cites this paper
• Management of Grapevine Leafroll Disease and Associated Vectors in Vineyards

  2017cites this paper
• Vector Transmission of Grapevine Leafroll-Associated Viruses

  2017cites this paper
• Mass Spectrometry of Aliphatic Macrolides, Important Semiochemicals or Pheromones.

  2017cites this paper
• (1S,3R)-cis-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, Ferrisia virgata

  2017cites this paper
• Sex Pheromone of the Cotton Mealybug, Phenacoccus solenopsis, with an Unusual Cyclobutane Structure

  2016cites this paper
• Chemistry of the Pheromones of Mealybug and Scale Insects

  2016cites this paper
• Pheromone synthesis. Part 260: Synthesis of (±)-(anti-1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde, the racemate of the female-produced sex pheromone of the pineapple mealybug (Dysmicoccus brevipes), and its syn-isomer

  2016cites this paper
• Triple Iron/Copper/Iminium Activation for the Efficient Redox Neutral Catalytic Enantioselective Functionalization of Allylic Alcohols

  2016cites this paper
• Chemical Diversity of Scarab Beetle Pheromones and its Implication in Chemical Evolution

  2016cites this paper
• Catalytic enantioselective OFF ↔ ON activation processes initiated by hydrogen transfer: concepts and challenges.

  2016cites this paper
• Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard.

  2015cites this paper
• Chiral methyl-branched pheromones.

  2015cites this paper
• Sciences of Phytochemistry Advances in Terpenoid Biosynthesis: Chemical Diversity and Emerging Industrial Applications

  year unknowncites this paper