Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae.

Literature DB >> 21243408

The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae.

C Rikard Unelius¹, Ashraf M El-Sayed, Andrew Twidle, Barry Bunn, Tania Zaviezo, M Fernanda Flores, Vaughn Bell, Jan Bergmann.

Abstract

The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae, was determined to be (1R,3R)-[2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl]methyl (R)-2-acetoxy-3-methylbutanoate. NMR, derivatization reactions, chiral gas chromatography-mass spectrometry, and comparison with synthetic chiral reference compounds, were used to determine the absolute configuration of this compound. This activity of this compound was further confirmed by testing synthetic stereoisomers of the compound as lures in traps for adult male mealybugs. Traps baited with 1,000 μg of the pheromone compound caught 36 times more males than traps baited with virgin females. A mixture of stereoisomers of the pheromone compound can be used for field trapping without adverse effects on trap catch. A comparison with the structures of other sex pheromones of mealybugs is presented.

Entities: Chemical Species

Mesh：

Substances：

Year: 2011 PMID： 21243408 DOI： 10.1007/s10886-010-9904-1

Source DB: PubMed Journal: J Chem Ecol ISSN： 0098-0331 Impact factor: 2.626

10 in total

1. Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus.

Authors: Takashi Nakahata; Noriaki Itagaki; Tomonori Arai; Hajime Sugie; Shigefumi Kuwahara
Journal: Biosci Biotechnol Biochem Date: 2003-12 Impact factor: 2.043

2. Identification and synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor (Maskell).

Authors: Hsiao-Yung Ho; Chau-Chin Hung; Ta-Hsien Chuang; Wen-Lung Wang
Journal: J Chem Ecol Date: 2007-09-21 Impact factor: 2.626

3. Synthesis and bioassay of racemic and chiral trans-alpha-necrodyl isobutyrate, the sex pheromone of the grape mealybug Pseudococcus maritimus.

Authors: Yunfan Zou; Kent M Daane; Walt J Bentley; Jocelyn G Millar
Journal: J Agric Food Chem Date: 2010-04-28 Impact factor: 5.279

4. Nuclear magnetic resonance spectra of the natural pyrethrins and related compounds.

Authors: A F Bramwell; L Crombie; P Hemesley; G Pattenden; M Elliott; N F Janes
Journal: Tetrahedron Date: 1969-04 Impact factor: 2.457

5. Olfactory discrimination among sex pheromone stereoisomers: chirality recognition by pink hibiscus mealybug males.

Authors: Aijun Zhang; Shifa Wang; Justin Vitullo; Amy Roda; Catharine Mannion; J Christopher Bergh
Journal: Chem Senses Date: 2006-06-15 Impact factor: 3.160

6. (2,3,4,4-Tetramethylcyclopentyl)methyl acetate, a sex pheromone from the obscure mealybug: first example of a new structural class of monoterpenes.

Authors: Jocelyn G Millar; Sharon L Midland; J Steven McElfresh; Kent M Daane
Journal: J Chem Ecol Date: 2005-11-11 Impact factor: 2.626

7. Identification of a sex pheromone component of Pseudococcus cryptus.

Authors: Tomonori Arai; Hajime Sugie; Syuntaro Hiradate; Shigefumi Kuwahara; Noriaki Itagaki; Takashi Nakahata
Journal: J Chem Ecol Date: 2003-10 Impact factor: 2.626

8. Sex pheromone of the longtailed mealybug: a new class of monoterpene structure.

Authors: Jocelyn G Millar; Jardel A Moreira; J Steven McElfresh; Kent M Daane; Amy S Freund
Journal: Org Lett Date: 2009-06-18 Impact factor: 6.005

9. Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.

Authors: Aijun Zhang; Divina Amalin; Shyam Shirali; Miguel S Serrano; Rosa A Franqui; James E Oliver; Jerome A Klun; Jeffrey R Aldrich; Dale E Meyerdirk; Stephen L Lapointe
Journal: Proc Natl Acad Sci U S A Date: 2004-06-14 Impact factor: 11.205

10. Identification and synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus madeirensis Green.

Authors: Hsiao-Yung Ho; Yu-Ting Su; Chi-Hung Ko; Ming-Yu Tsai
Journal: J Chem Ecol Date: 2009-06-16 Impact factor: 2.626

10 in total

5 in total

The absolute configuration of the sex pheromone of the citrophilous mealybug, Pseudococcus calceolariae.

1. Synthesis of the sex pheromone of the citrus mealybug, Pseudococcus cryptus.

2. Identification and synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor (Maskell).

3. Synthesis and bioassay of racemic and chiral trans-alpha-necrodyl isobutyrate, the sex pheromone of the grape mealybug Pseudococcus maritimus.

4. Nuclear magnetic resonance spectra of the natural pyrethrins and related compounds.

5. Olfactory discrimination among sex pheromone stereoisomers: chirality recognition by pink hibiscus mealybug males.

6. (2,3,4,4-Tetramethylcyclopentyl)methyl acetate, a sex pheromone from the obscure mealybug: first example of a new structural class of monoterpenes.

7. Identification of a sex pheromone component of Pseudococcus cryptus.

8. Sex pheromone of the longtailed mealybug: a new class of monoterpene structure.

9. Sex pheromone of the pink hibiscus mealybug, Maconellicoccus hirsutus, contains an unusual cyclobutanoid monoterpene.

10. Identification and synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus madeirensis Green.

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

2. A new class of mealybug pheromones: a hemiterpene ester in the sex pheromone of Crisicoccus matsumotoi.

3. Mating Disruption of Pseudococcus calceolariae (Maskell) (Hemiptera, Pseudococcidae) in Fruit Crops.

4. Multiple Mating in the Citrophilous Mealybug Pseudococcus calceolariae: Implications for Mating Disruption.

5. Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology.