insectpheromones-210621093758.pptx of insect

Insect pheraomones what are way of attractant of insect

1. INSECT PHEROMONES Dr. Basavarajaiah S. M. Assistant Professor and Coordinator PG Department of Chemistry Vijaya College, Bengaluru-560004. [email protected]

2. Contents Communication in Insects. Classification of Semiochemicals. Introduction to Insect Pheromones. Uses of Insect Pheromones . Synthesis of Insect Pheromones. Use of pheromones in insect pest management.

3. COMMUNICATION IN INSECTS Insects communicate both with organisms of the same species (intraspecific communication) and directly or indirectly with organisms of other species (interspecific communication) for many reasons: Reproduction. Identify  . To warn other organisms . To localize sources of recourses.   As an  alert signal   or defend territory .

4. Tactile communication: “The touch” Chemical communication: “smell and taste” Visual communication: “The sight” Auditory communication: “the hearing”  or Acoustic communication Insects use almost all senses to communicate. Along this section, we’ll analyze one by one all communication systems that insects developed through the “five sense”, just like some of the flashiest examples.

5. Tactile communication: “The touch” “Tandem running”: Follow the leader Example; Ants Dancing bees Example; Honey bee Chemical communication: “smell and taste” In this type of communication, the emitter scatters chemical substances at the environment which are detected by other organisms .  Pheromones (for finding a mate), Allelochemicals (as alarm signals, as a defensive system…)

6. Visual communication: “The sight” Visual communication in insects takes place by two main systems:  Body color patterns and Light signals ( Bioluminescence ). Auditory communication: “the hearing” Insects emit a wide variety of sounds in different frequencies, amplitude and periodicity, and each species has a very well defined pattern. In fact, only by registering and analyzing insect’s sounds we can identify the species that has emitted them.

7. SEMIOCHEMICALS A semiochemical, from the Greek semeion , meaning "signal", is a chemical substance or mixture released by an organism that affects the behaviors of other individuals. Semiochemical communication can be divided into two broad classes: communication between individuals of the same species (intraspecific) or communication between different species (interspecific).

8. INTRODUCTION TO INSECT PHEROMONES A pheromone  is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to impact the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Primer pheromones trigger a change of developmental events (in which they differ from all the other pheromones, which trigger a change in behavior). Releaser pheromones are pheromones that cause an alteration in the behavior of the recipient. 

9. Aggregation Aggregation pheromones function in mate selection, overcoming host resistance by mass attack, and defense against predators. A group of individuals at one location is referred to as an aggregation, whether consisting of one sex or both sexes. Male-produced sex attractants have been called aggregation pheromones, because they usually result in the arrival of both sexes at a calling site and increase the density of conspecifics surrounding the pheromone source.

10. Trail Pheromone Social insects commonly use trail pheromones. For example, ants mark their paths with pheromones consisting of volatile hydrocarbons. Certain ants lay down an initial trail of pheromones as they return to the nest with food. This trail attracts other ants and serves as a guide.   As long as the food source remains available, visiting ants will continuously renew the pheromone trail. The pheromone requires continuous renewal because it evaporates quickly.

11. Sex Pheromones Sex pheromones indicate the availability of the female for breeding. Male animals may also emit pheromones that convey information about their species and genotype. Territorial Pheromones Laid down in the environment, territorial pheromones mark the boundaries and identity of an organism's territory. In cats and dogs, these hormones are present in the urine, which they deposit on landmarks serving to mark the perimeter of the claimed territory.

12. Epideictic Pheromones Epideictic pheromones are different from territory pheromones, when it comes to insects.  Fabre observed and noted how "females who lay their eggs in these fruits deposit these mysterious substances in the vicinity of their clutch to signal to other females of the same species they should clutch elsewhere." It may be helpful to note that the word epideictic, having to do with display or show (from the Greek ' deixis '), has a different but related meaning in rhetoric, the human art of persuasion by means of words.

13. Uses of Insect Pheromones In pest and Insect control management; Pheromones of certain pest insect species, such as the Japanese beetle, acrobat ant, and the gypsy moth, can be used to trap the respective insect for monitoring purposes, to control the population by creating confusion, to disrupt mating, and to prevent further egg laying. Avoidance of inbreeding; Mice can distinguish close relatives from more distantly related individuals on the basis of scent signals, which enables them to avoid mating with close relatives and minimizes deleterious inbreeding.

14. Humans; While humans are highly dependent upon visual cues, when in close proximity smells also play a role in sociosexual behaviors. Experiments have focused on three classes of putative human pheromones: axillary steroids, vaginal aliphatic acids, and stimulators of the vomeronasal organ. Axillary steroids; Several axillary steroids have been described as potential human pheromones: androstadienol ,   androstadienone ,  androstenol ,  androstenone , and  androsterone .

15. Synthesis of Insect Pheromones GRANDISOL Grandisol is a pheromone primarily important as the sex attractant of the cotton boll weevil ( Anthonomus grandis ), from which it gets its name.  It is also a pheromone for other related insects. The cotton boll weevil is an agricultural pest that can cause significant economic damage if not controlled. Grandisol is the major constituent of the mixture known as grandlure, which is used to protect cotton crops from the boll weevil.

16. Grandisol with the molecular formula C 10 H 18 O. It is a monoterpene containing a cyclobutane ring, an alcohol group, an  alkene  group and two  chiral  centers. Grandisol was first isolated, identified, and synthesized by J. Tumlinson  et al. at Mississippi State University in 1969.

17. Synthesis of Grandisol Method-I

18. Method-II Tetrahedron 63 (23 ), 4 June 2007, Pages 4968-4974

19. J Org Chem. 2010 Jan 1;75(1):226-8. doi : 10.1021/jo9020375. Method-III

20. (+)-FARANAL [3S,4R,6E,10Z,(+)]-3,4,7,11-Tetramethyl-6,10-tridecadienal The True Trail Pheromone of Pharaoh's Ant

21. Method-I

22. Method-II

23. BREVICOMIN Pheromone from Dendroitis brevicomis

24. Method-I

25. J. Braz. Chem. Soc. 13 (2) • 2002  Method-II

26. Method-III

27. (+)- DISPARLURE The gypsy moth ( Porthytria dispar ) is a serious pest of the forests. In 1976 B.A. Bierl et.al., (Science, 170,88 (1970)) isolated the sex pheromone (+)- Disparlure from extracts of 78,000 tips of the last two abdominal segments of female moths.

28. Chem. Ber., 109, 3375 (1976) Method-I

29. Angew. Chem., Int. Ed., 11, 60 (1972). Klunenberg et.al., Method-II

30. J. Am. Chem. Soc., 96, 7842 (1974) Method-III

31. Mori et.al.,Tetrahedron , 53, 833 (1979) Method-IV

32. Kossier B. E.. et.al., (J. Am. Chem. Soc., 103, 464 (1981) Method-V

33. 3,11-Dimethy1-nonacosanone Pheromone of German cockroaches. Tetrahedron, Volume 72, Issue 30, 28 July 2016, Pages 4593-4607

34. BOMBYKOL Bombykol or 10(E),12(Z)- Hexadecadienol . Has been identified as a sex pheromone of the silkworm  Bombyx mori . Discovered by Adolf Butenandt in 1959. It was the first pheromone to be characterized chemically. Can be used in pest control. It has been synthesized on a gram scale.

35. Dasardhi , P., P. Neelakantan , S.J. Rao , and U.T. Bhalerao . 1991. The oxidation of bombykol to bombykal . Synth . Comm. 21:183. Method-I

36. Starting from vernolic acid ( 1 ), first the epoxy group was ring-opened, resulting in a diol product ( 2 ). This diol could be selectively cleaved to the aldehyde ( 3 ) without affecting the carbon-carbon double bond and leaving hexenal ( 4 ) as a side-product, that in itself may find useful applications in the flavor industry. Protecting the carboxylic acid group and isomerization of the double bond yielded a reactive intermediary product [12-oxo-10(E)- dodecenoic acid ( 5 )] which contained a carboxylic ester and also an aldehyde functionality in conjugation with the carbon-carbon double bond. Subsequent Wittig olefination of ( 5 ) leads to the 10(E), 12(Z)-product ( 6 ), which is selectively reduced to bombykol ( 7 ).

37. PLOS ONE, 2012, 7(9): e44190. Method-II Method-III

38. MULTISTRIATIN Multistriatin is a pheromone of the elm bark beetle. It is a volatile compound released by a virgin female beetle when she has found a good source of food, such as an elm tree. Males beetles, which carry the fungus which causes Dutch elm disease, are attracted to the pheromone. Hence multistriatin could be used to trap beetles and so prevent the spread of the disease. Note: Only the natural stereoisomer, α-multistriatin, attracts the elm bark beetles.

39. Method-I

40. Method-II Method-III

41. USE OF PHEROMONES IN INSECT PEST MANAGEMENT Currently, pheromones and other semio-chemicals are being used to monitor and control pests in millions of hectares of land. Highly relevant for IPM programmes of tephritid fruit flies is the use of parapheromones. These are chemical compounds of anthropogenic origin, not known to exist in nature but are structurally related to natural pheromone components, that in some way affect physiologically or behaviorally the insect pheromone communication system, eliciting a similar response to that of a true pheromone.

42. Commercial Pheromones Stored Product Moth „ Warehouse Beetle „ Cigarette Beetle „ Drugstore Beetle Red and Confused Flour Beetles „ Lesser Grain Bore

43. Uses of Pheromones Detection „ Monitoring „ Mass Trapping „ Mating Disruption Attracticide „or Attract-and-Kill Pathogen Dispersion

44. Monitoring Monitoring is an effective way to determine the population trends of insects and plays a critical role in pest management programmes. Pheromone-based behavioral manipulation has been developed as a monitoring tool for many pests. It involves the use of a synthetically-derived pheromone formulated into a dispenser and trap to selectively attract and intercept the target insect. The advantages of using pheromones for monitoring pests include lower costs, specificity, ease of use, and high sensitivity.

45. Mating Disruption During mate location, sex pheromones are commonly used as long-range cues to orient insect species toward potential mates. Synthetic blends of sex pheromones can be used to permeate the environment and disrupt the orientation of males to females, thereby inhibiting the mating process. Mating disruption in moths works mainly through competitive attraction compared to the non-competitive mechanisms (camouflage, desensitization, and sensory imbalance).

46. Mass Trapping This strategy involves the use of attractive semiochemicals (synthetic aggregation and sex pheromones, host volatiles, etc.) involved in the mate finding and/or foraging behaviors of the target pest with the purpose of bringing them to killing devices. Insects are removed from the population using small amounts of insecticides, adhesives, water, or other physical structures. Competitiveness of traps with wild calling females, pest density, biology and ecology of the target pest, operational costs, and mated female immigration risk are the important considerations in devising a mass trapping pest management programme.

47. Attract-and-Kill The attract-and-kill method is one type of behavioral manipulation method that combines a long-distance olfactory stimulus to attract a particular pest in combination with some type of killing agent. This approach is similar to mass trapping but does not require the physical entrapment of the target pests. Both mass trapping and attract-and-kill approaches work best when pest density is relatively low.

48. Pheromone Lures Fiber „ Plastic Tube „ Rubber Septa „ Controlled Release Membrane „ Beads „ Oil Solutions „ Gels

49. Trap Types Funnel Traps „ Grain Probe Traps „ Pitfall Traps „ Sticky Traps „ Box Traps „ Wing Traps „ Delta Traps „ Diamond Traps „ Discreet Trap

50. Additional Attractants Food odors enhance the response to pheromones for some insects. „ Flower odors increase response to pheromones in some insects. „ These attractants may need to be added to trap for it to be effective. Pheromone Trapping Principles Active Space „ Additional Attractants „ Temperature Effects Trap Placement Trap Density