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Allelochemicals from Soybean Affecting Pseudoplusia Includens (Walker) Biology and Pheromone from Chilo Plejadellus Zinken Mediating C

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Allelochemicals from Soybean Affecting Pseudoplusia Includens (Walker) Biology and Pheromone from Chilo Plejadellus Zinken Mediating C Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1985 Allelochemicals From Soybean Affecting Pseudoplusia Includens (Walker) Biology and Pheromone From Chilo Plejadellus Zinken Mediating C. Plejadellus Sexual Behavior (Looper). Porfirio Caballero Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Caballero, Porfirio, "Allelochemicals From Soybean Affecting Pseudoplusia Includens (Walker) Biology and Pheromone From Chilo Plejadellus Zinken Mediating C. Plejadellus Sexual Behavior (Looper)." (1985). LSU Historical Dissertations and Theses. 4118. https://digitalcommons.lsu.edu/gradschool_disstheses/4118 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This reproduction was made from a copy of a manuscript sent to us for publication and microfilming. While the most advanced technology has been used to pho­ tograph and reproduce this manuscript, the quality of the reproduction is heavily dependent upon the quality of the material submitted. Pages in any manuscript may have indistinct print. In all cases the best available copy has been filmed. The following explanation of techniques is provided to help clarify notations which may appear on this reproduction. 1. Manuscripts may not always be complete. When it is not possible to obtain missing pages, a note appears to indicate this. 2. When copyrighted materials are removed from the manuscript, a note ap­ pears to indicate this. 3. Oversize materials (maps, drawings, and charts) are photographed by sec­ tioning the original, beginning at the upper left hand comer and continu­ ing from left to right in equal sections with small overlaps. Each oversize page is also filmed as one exposure and is available, for an additional charge, as a standard 35mm slide or in black and white paper format. * 4. Most photographs reproduce acceptably on positive microfilm or micro­ fiche but lack clarity on xerographic copies made from the microfilm. For an additional charge, all photographs are available in black and white standard 35mm slide format.* *For more information about black and white slides or enlarged paper reproductions, please contact the Dissertations Customer Services Department. ’ University Mkrofilms M , International 8610628 Caballero, Porfirio ALLELOCHEMICALS FROM SOYBEAN AFFECTING PSEUDOPLUSIA INCLUDENS (WALKER) BIOLOGY AND PHEROMONE FROM CHILO PLEJADELLUS ZINKEN MEDIATING C. PLEJADELLUS SEXUAL BEHAVIOR The Louisiana State University and Agricultural and Mechanical Col. Ph.D. 1985 University Microfilms International300 N. Zeeb Road, Ann Arbor, Ml 48106 PLEASE NOTE: In all cases this material has been filmed in the best possible way from the available copy. Problems encountered with this document have been identifieda checkhere with mark V . 1. Glossy photographs or pages______ 2. Colored illustrations, paper or _______print 3. Photographs with dark background_____ 4. Illustrations are poor c o_______ p y 5. Pages with black marks, not original ______copy 6. Print shows through as there is text on both sides_______ of page 7. Indistinct, broken or small print on several pages 8. Print exceeds margin requirements______ 9. Tightly bound copy with print lost_______ in spine 10. Computer printout pages with indistinct_______ print 11. P ag e(s)____________ lacking when material received, and not available from school or author. 12. P ag e(s)____________ seem to be missing in numbering only as text follows. 13. Two pages numbered . Text follows. 14. Curling and wrinkled pa g e s _______ 15. Dissertation contains pages with print at a slant, filmed as received___________ 16. O t h e r __________________________________________________________ University Microfilms International ALLELOCHEMICALS FROM SOYBEAN AFFECTING PSEUDOPLUS1A 1NCLUDENS (WALKER) BIOLOGY AND PHEROMONE FROM CHILD PLEJADELLUS ZINKEN MEDIATING C. PLEJADELLUS SEXUAL BEHAVIOR A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in The Department of Chemistry by Porfirio Caballero B.S. , Universidad Autonoma de Nuevo Leon, 1978 M.S., Universidad Autonoma de Nuevo Leon, 1980 December, 1985 AKNOWLEDGEMENTS The author would like to express his most grateful appreciation to Dr. Charles M. Smith and Dr. Nikolaus H. Fischer for their friendship and encouragement during the course of this research; to his wife Ana and son Ulises for their patience and understanding; to Dr. F. K. Cartledge, Dr. E. Dunnigan, Dr. D. K. Carpenter and Dr. N. S. Bhacca for their advices and comments on this dissertation; to Mrs. Helga Fischer, the Fischer Fytochemical Farm, Dr. Alberto Pantoja, Mr. Miles Duthile, Mrs. Maurine Riley and Miss. Colwell Cook for making this an enjoyable time; to Dr. J. F. Robinson, Dr. N. P. Tugwel, Dr. M. 0. Way, Mr. George Trahan and Mr. Bobby Michott for their help in the realization of the C. plejadellus pheromone project; to Mr. Christian B. Boussert and Mr. Guerrini Vincent for their help in the construction of the glass equipment used in this research; to Mr. Don Patterson, Mr. Herbert Land and Mr. Marcus Nauman for their help on the use of the analytical instrumentation; and to Dr. Frank Fronczek for the determination of the crystal structure of afrormosin. Finally, He would like to express his appreciation to Louisiana State University, USDA and CONACYT for the financial support and to the Charles E. Coates Memorial fund of the LSU foundation (donated by Dr. George H. Coates) for financial provision in the production of this dissertation. ii TABLE OF CONTENTS. ACKNOWLEDGMENTS..................................... ii TABLE OF CONTENTS. ............................... iii LIST OF TABLES. ............................... iv LIST OF FIGURES..................................... vi ABSTRACT............................................... viii INTRODUCTION......................................... 1 CHAPTER 1. Allelochemicals from Soybean Affecting Pseudoplusi a Lncludens Biology............ 10 Introduction............................. 11 Materials and Methods.................... 16 Results.................................. 20 Discussion............................. 24 References............................... 28 CHAPTER 2.Pheromone from Chilo plejadellus Zinken Mediating C. plejadellus Sexual Behavior . 39 Introduction.............................. 40 Materials and Methods................... 44 Results.................................... 48 Discussion................................ 51 References................................ 54 BIBLIOGRAPHY......................................... '74 VITA................................................. 77 iii List of Tables. Chapter 1. Table 1. Feeding of sixth instar P. includens on cellulose nitrate discs treated with soybean PI227687 leaf extracts and extract fractions.. 34 Table 2. Development and survival of P. includens larvae on artificial diet supplemented with fractions of methanol and dichloromethane leaf extracts from soybean PI227687.......... 35 Chapter 2. Table 1. Stem borers classified in the Chilo genus.. 58 Table 2. Attraction of male C. plejadellus moths attracted to traps baited with (Z)-13-octadecenal. Crowley, La. 1985........ 59 Table 3. Attraction of male C. plejadellus moths attracted to traps baited with (Z)-13-octadecenal. LaKE Providence, La. 1985. .60 Table 4. Attraction of male C. plejadellus moths attracted to traps baited with (Z)-13-octadecenal. Mer Rouge, La. 1985. 61 Table 5. Total number of moths C. plejadellus attracted to traps baited with 3 mg of (Z)-13 octadecenal and a light trap. Crowley, LA. 1985.................. 62 Table 6. Attraction of male C. plejadellus to traps baited with 3 mg of (Z)-13-octadecenal iv on Crowley, Lake Providence, and Mer Rouge Louisiana. 1985. ......... .......... 63 Table 7. Attractionof male C. plajadel lus moths to traps baited with 3 mg of (Z)-13-octadecenal on Arkansas and Texas. 1985................... 64 Table 8. Attraction of male C. plejadsllus moths at various sites in North Louisiana. 1985. 65 v List of Figures. Chapter 1. Figure 1. Extraction procedure for extracting soybean PI227687 resistant to soybean looper Pseudoplusia includens ................ 36 Figure 2. X-Ray structure of Afrormosin (3) ......... 37 Figure 3. Examples of isoflavonoids and their prenylated derivatives.......................... 38 Chapter 2. Figure 1. Distribution of pheromone traps with (Z)-1 3-octadecenal. Louisiana. 1985.......... 66 Figure 2. Distribution of pheromone traps with (Z)-13-octadecenal. Arkansas. 1985........... 67 Figure 3. Distribution of traps for concentration ratio studies in Crowley, LA. 1985........... 68 Figure 4. Distribution of pheromone traps for monitoring C. plejadellus populations...........69 at Crowley, La. 1985 Figure 5. Gas chromatogram profile from C. plejadellus female abdominal tip extracts..................................... 70 Figure 6. Mass spectrum of (Z)-13-octadecenal isolated from C. plejadellus female abdominal tip extracts.......................... 71 vi Figure 7. Comparison of C. plejadellus catches
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