1. Prof. Dr. Jocelyn Miller
jocelyn.millar@ucr.edu
A BRIEF SCIENTIFIC
ACCOUNT of
Presented By:
Jawwad Hassan Mirza
Student ID# 435108485
Ph. D. Scholar (2nd Semester)
College of Food and Agriculture Sciences
King Saud University, Riyadh, KSA

2. INTRODUCTION
• Organic Chemist
– Insect semiochemistry
– Chemical ecology
• Study of natural chemicals that mediate interactions between
organisms
• Sex or aggregation pheromones (chemical signals) and cues from hosts or
habitats
– locate and recognize their preferred feeding and egg-laying sites.
• Synthesize newly discovered pheromone and kairomone structures
• Biological control of exotic pests of eucalyptus, vibrational signaling in
true bugs and other insects
OBJECTIVES
 To gain insight into the role of chemical and other types of signals as
mediators of insect behavior
 To develop practical applications for pheromones, kairomones, and other
behavior-modifying chemicals

3. • Degrees
– BSc Chemistry 1978 Simon Fraser University, B.C. Canada
– PhD Organic Chemistry 1983 Simon Fraser University, B.C. Canada
• Awards
– 2008 - Entomological Society of America, National Award for Excellence in Integrated Pest
Management.
– 2008 - Entomological Society of America, Pacific Branch, Award for Excellence in Integrated Pest
Management
– 2006 - Entomological Society of America Team IPM Award
– 2006 - C.W. Woodworth Award, Pacific Branch of the Entomological Society of America
– 2005-6 - President, International Society of Chemical Ecology
– 2005 - Entomological Society of America, Pacific Branch, ESA Foundation Team Award in IPM
– 2003 - Fellow, American Association for the Advancement of Science
– 2001 - Entomological Society of America, Pacific Branch, Recognition Award in Entomology
– 2001 - Entomological Society of America, Syngenta Crop Protection Recognition Award
– 1996 - Japanese Government Research Award For Foreign Specialist
• Publications
– About 240 mostly on identification, synthesis of Pheromones and their use in IPM Program
• Edited Books
– K. Nakamuta and J.G. Millar (eds.) Chemical Ecology of Wood-boring Insects. Forestry and Forest
Products Research Institute, Tsukuba, Japan. 98 pp.
– Cardé, R.T. and J.G. Millar. 2004. Advances in Insect Chemical Ecology. Cambridge University Press.
– Haynes, K.F. and J.G. Millar. 1998. Methods in Chemical Ecology. Volume 2: Bioassay Methods.
Kluwer, NY.
– Millar, J.G. and K.F. Haynes. 1998. Methods in Chemical Ecology. Volume 1: Chemical Methods.
Kluwer, NY.

4. RESEARCH INTERESTS
AGGREGATION & SEX PHEROMONES
1. IDENTIFICATION OF PHEROMONES
2. SYNTHESIS OF PHEROMONES
3. USE IN IPM PROGRAM
TARGET INSECT
FAMILILES:
• HEMIPTERA
• LEPIDOPTERA
• COLEOPTERA
• DIPTERA

5. 1.1: IDENTIFICATION OF THE SEX PHEROMONE OF A PROTECTED SPECIES, THE
SPANISH MOON MOTH GRAELLSIA ISABELLAE (LEPIDOPTERA: SATURNIIDAE).
• Sex attractant pheromones are highly sensitive and selective tools
• Only one reported case of pheromones
being used to monitor protected species
• Analyses of SPME wipe samples and
solvent extracts of dissected pheromone glands by GC-EAD
• Identification as the single component
(4E,6E,11Z)-hexadecatrienal.
• Lures loaded with this compound attracted male moths from populations of this
species at a number of widely separated field sites
• The utility of pheromones in sampling for potentially endangered insect species.
Jocelyn G. Millar1,*, J. Steven McElfresh1, Carmen Romero1, Marta Vila2, Neus Mari-Mena2, and Carlos Lopez-Vaamonde. 2010. Identification of
the Sex Pheromone of a Protected Species, the Spanish Moon Moth Graellsia isabellae (Lepidoptera: Saturniidae). J. Chem. Ecology 36, 923-932.

6. 1.2: SEX PHEROMONE OF THE MIRID BUG PHYTOCORIS RELATIVUS
• Adult females 2:1 blend of hexyl acetate with (E)-2-octenyl butyrate
– Hexyl acetate from both sexes
– (E)-2-octenyl butyrate only by females.
• Adults anesthetized, cut in pieces and extract were analyzed
• Attraction of males increased with dose, with doses of 0.1 to 33 mg loaded on
grey rubber septa.
• Attractiveness of rubber septum lures decreased quickly
with age due to the volatility of the two pheromone components.
Millar, J.G., R.E. Rice, and Q. Wang. 1997. Sex Pheromone of the Mirid Bug Phytocoris relativus Knight. J. Chem. Ecology 23:1743-1754.
by GC and GC-MS

7. 1.3: IDENTIFICATION OF OVIPOSITION ATTRACTANTS FOR CULEX
QUINQUEFASCIATUS FROM FERMENTED BERMUDA GRASS INFUSIONS
• Compounds isolated and identified from a fermented Bermuda
glass infusion
• Fractionation by liquid chromatography
(Phenol) (4-methylphenol) (4-ethylphenol) (Indole) (3-methylindole)
• A blend of the 5 compounds strongly stimulated oviposition, as did
blends of any 4 of them.
• Only 3-methylindole consistently induced oviposition, in concentrations
spanning 5 orders of magnitude
Millar, J. G., J. D. Chaney, and M. S. Mulla. 1992. Identification of Oviposition Attractants for Culex quinquefasciatus from Fermented Bermuda
Grass Infusions. J. Amer. Mosq. Control Assoc. 8: 11-17.

8. 1.4: SEX PHEROMONE COMPONENTS OF THE GEOMETRID MOTHS LOBOPHORA
NIVIGERATAa AND EPIRRHOE SPERRYIb.
• b3Z,6Z,9Z-Nonadecatriene (3Z,6Z,9Z-19 : H)
female sex pheromone component
• 3Z,6Z,9Z-18:H and 6Z,9Z-19:H no apparent
biological activity.
• Extracts of sex pheromone glands from
female moths prepared by a 20-min pentane
extraction of the terminal three or four
abdominal segments.
• GC-EAD
• a3Z,6Z,9Z-21:Hfemale sex pheromone component
• Attraction of male moths synergized by the
addition of small amounts of 6Z,9Z-21:H to
lures.
Millar, J. G., M. Giblin, D. Barton and E. W. Underhill. 1992. Sex Pheromone Components of the Geometrid Moths Lobophora
nivigerata and Epirrhoe sperryi. J. Chem. Ecol. 18: 1057-1068.

9. 2.1: STEREOSPECIFIC SYNTHESIS OF THE SEX PHEROMONE OF THE
PASSIONVINE MEALYBUG, PLANOCOCCUS MINOR
• A short and completely stereospecific synthesis of
(E)-2-isopropyl-5-methyl-2,4-hexadienyl acetate, the
very recently identified sex pheromone of the
passionvine mealybug Planococcus minor, is
described.
• In the key step, CuI-catalyzed anti-addition of a
Grignard reagent to a propargyllic alcohol
intermediate gave the required trisubstituted alkene
with 100% regio- and stereospecificity.
• The stereochemical purity of the pheromone is
critically important because the (Z)-isomer is a
powerful behavioral antagonist.
Jocelyn G. Millar. 2008. Stereospecific synthesis of the sex pheromone of the passionvine mealybug, Planococcus minor. Tetrahedron Letters
49:315-317.

11. 2.2: SYNTHESIS OF THE SEX PHEROMONE OF THE OBSCURE MEALYBUG, THE FIRST
EXAMPLE OF A NEW CLASS OF MONOTERPENOIDS
• A diastereoselective synthesis of (1R*,2R*,3S*)-1-
acetoxymethyl-2,3,4,4-tetramethylcyclopentane, the
sex pheromone
• of the obscure mealybug Pseudococcus viburni, is
described. Key steps included the polyphosphoric
acid-catalyzed cyclization of
• isobutyl methacrylate to form the core five-
membered ring, and diastereoselective quenching of
an enolate intermediate to give
• the thermodynamically less favored cis orientation of
vicinal methyl groups in a cyclopentanone
intermediate.
Jocelyn G. Millar and Sharon L. Midland. Synthesis of the sex pheromone of the obscure mealybug, the first example of a new class of
monoterpenoids. Tetrahedron Letters 48:6377-6379. Published online Aug 11-07, http://dx.doi.org/10.1016/j.tetlet.2007.06.169

13. 2.3: (9Z)-9,13-TETRADECADIEN-11-YNAL, THE SEX PHEROMONE OF THE AVOCADO
SEED MOTH,STENOMA CATENIFER
• The highly unsaturated aldehyde (9Z)-9,13-
tetradecadien-11-ynal and the corresponding alcohol
were
• identified as possible sex pheromone components of
the avocado seed moth, Stenoma catenifer. The
aldehyde
• as a single component attracted more male moths
than caged virgin female moths, and addition of
• the analogous alcohol and/or acetate decreased
attraction. A stereospecific synthesis of the
pheromone is
• described.
Jocelyn G. Millar, Mark Hoddle, J. Steven McElfresh, Yunfan Zou, and Christina Hoddle. 2008. (9Z)-9,13-Tetradecadien-11-ynal, the sex
pheromone of the avocado seed moth,Stenoma catenifer. Tetrahedron Lett. 49: 4820-4823. Published online June 13-08

15. 2.4: METHYL (2E,4Z,6Z)-DECA-2,4,6-TRIENOATE, A THERMALLY UNSTABLE, SEX-
SPECIFIC COMPOUND FROM THE STINK BUG THYANTA PALLIDOVIRENS
• Sexuallymaturernaletinkbuga,
Thyuntupallidovirwrs,rekasea rnsle-
specificblendof
• volatiks,
includingseveralseaquiterpenehydrowbo33s,and
the highlyconjugatedestermethyl
• (2E,4Z,6Z)4eca-2,4,6-trienoate 1.
Thelattereompormdwassynthesize andfoundto
rearrange
• underGCconditionsvia a
1,7aigmatropicrearrangemen
Millar, J.G. 1997. Methyl (2E,4Z,6Z)-deca-2,4,6-trienoate, a Thermally Unstable, Sex-Specific Compound from the Stink Bug Thyanta pallidovirens.
Tetrahedron Letters 38:7971-7972.

17. 3.1: FIELD TRIALS OF AGGREGATION PHEROMONES FOR THE STINK
BUGS CHLOROCHROA UHLERI AND CHLOROCHROA
SAYI(HETEROPTERA: PENTATOMIDAE).
• Cylindrical Screen Traps baited male-produced pheromone,
methyl (E)-6-2,3-dihydrofarnesoate
• Host Plant odor volatiles + pheromones = no significant
• Combining the pheromone of two sympatric stink bug species decreased trap
captures
– Chlorochroa sayi, Euschistus conspersus
• With C. sayi, all three of the male-specific pheromone compounds required for
optimal attraction.
• With C. uhleri, adults of both sexes attracted to pheromone lures in
approximately equal numbers.
• Lures loaded with high amount of methyl (E)-6-2,3-dihydrofarnesoate to obtain
the best trap catch
• The pheromone components of C. uhleri or E. conspersus not interfered with the
attractiveness of the C. sayi pheromone in lures containing a blend of all three
pheromones.
Jocelyn G. Millar, Heather M. McBrien, and J. Steven McElfresh. 2010. Field Trials of Aggregation Pheromones for the Stink Bugs Chlorochroa
uhleri and Chlorochroa sayi(Heteroptera: Pentatomidae). Journal of Economic Entomology 103:1603-1612.

18. 3.2: PENTATOMID BUG PHEROMONES IN IPM: POSSIBLE
APPLICATIONS AND LIMITATIONS
• Male-produced pheromone components have been identified from several
species of
• agriculturally important stink bugs
• T. pallidovirens = thermally unstable ester, methyl (2E,4Z,6Z)-decatrienoate
– Pheromone attracted only females, as well as a specialist predator, the sphecid wasp Astata
occidentalis.
• A. hilare = two isomers, (4S)-cis- and (4S)-trans-(Z)-bisabolene epoxides(19:1)
– Both compounds were required for attraction of females.
• Male C. sayi = methyl geranate (methyl citronellate and methyl
dihydrofarnesoate)
– Only methyl geranate appeared to be required for attraction.
• Males of C. uhleri and C. ligata = methyl dihydrofarnesoateas (other minors)
– Only methyl dihydrofarnesoate appeared to be required for attraction of females.
• Relatively low numbers of bugs caught = inefficient trap designs.
• Phytophagous stink bugs communicate over shorter distances
– Substrate-borne vibrational signals, critically important in attracting bugs right up to pheromone
sources.
Millar, J.G., H. L. McBrien, H.-Y. Ho, R. E. Rice, E. Cullen, F. G. Zalom, and A. Cokl. Pentatomid Bug Pheromones in IPM: Possible Applications and
Limitations. 2002. Bulletin of the International Organization of Biological Control, Pheromone Working Group. Vol. 25:1-11. Published on the

19. 3.3: DEVELOPMENT AND OPTIMIZATION OF METHODS FOR USING SEX
PHEROMONE FOR MONITORING VINE MEALYBUG IN CALIFORNIA VINEYARDS
• Lavandulyl senecioate (synthetic)
– As attractive to male mealybugs as the insect-produced (S)-
enantiomer
• Lavandulol, found in extracts from virgin females
– antagonized attraction of males at higher doses.
• Rubber septum lures (10-1,000 gm doses)
– Were equally attractive
• Lures remained attractive for at least 12 wks under field
conditions.
• Delta traps were more effective than double-sided sticky cards
– minimized captures of nontarget insects.
• Pheromone-baited traps had an effective range of at least 50 m.
• Comparison of visual sampling methods and sampling of males
with pheromone-baited traps
– significantly correlated
Millar, J.G., K. M. Daane, J. S. McElfresh, J. Moreira, R. Malakar-Kuenen, M. Guillen, and W. J. Bentley. 2002. Development and Optimization of
Methods for Using Sex Pheromone for Monitoring Vine Mealybug in California Vineyards. J. Economic Entomol. 95: 706-714.

20. 3.4: TECHNOLOGICAL PROBLEMS ASSOCIATED WITH USE OF INSECT PHEROMONES
IN INSECT MANAGEMENT
• Sex pheromone components were identified for many of the major lepidopteran pests of
concern to agriculture a number of years ago. However, despite intensive efforts,
implementation of large-scale, effective, and reliable insect control strategies based on
pheromones remains elusive for many pest species. For example, pheromone-based
mating disruption of codling moth still suffers from problems which have prevented the
widespread adoption of mating disruption for control of this world-wide pest, in spite of
continuous research efforts spanning 20 years. During this time, our knowledge and
understanding of possible causes of unsatisfactory performance of pheromones in insect
pest management has increased substantially. It is now commonly acknowledged that site
characteristics such as the slope of a site and edge effects associated with adjacent
cropping systems can contribute to the failure of mating disruption. However, field
researchers have focused less attention on technological factors such as pheromone
dispenser performance, pheromone purity, and pheromone degradation under field
conditions. Both field researchers and growers are usually dependent on commercial
outlets for supplies of both pheromone and dispensers, but the pressure on commercial
suppliers to market product may result in products being released before adequate
efficacy tests under field conditions have been conducted. In this paper, we will
summarize results from several studies which examined pheromone dispenser
characteristics, pheromone purity, and pheromone degradation under field conditions.
The results will be discussed in terms of the performance of several pheromone products
in different agricultural systems.
Jocelyn G. Millar, J. Steven McElfresh, and Richard E. Rice. 1997. Technological problems associated with use of insect pheromones in insect
management. IOBC wprs Bulletin 20: 19-25.

21. THANK YOU FOR LISTENING
YOU HAVE BEEN A GREAT AUDIENCE
ANY QUESTIONS?