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Investigation of Natural and Synthetic Cyanohydrins, Insecticidal Properties, and Their Metabolism Dong-Sik Park Iowa State University

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Investigation of Natural and Synthetic Cyanohydrins, Insecticidal Properties, and Their Metabolism Dong-Sik Park Iowa State University Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 2002 Investigation of natural and synthetic cyanohydrins, insecticidal properties, and their metabolism Dong-Sik Park Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Entomology Commons, and the Toxicology Commons Recommended Citation Park, Dong-Sik, "Investigation of natural and synthetic cyanohydrins, insecticidal properties, and their metabolism " (2002). Retrospective Theses and Dissertations. 538. https://lib.dr.iastate.edu/rtd/538 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. ProQuest Information and Learning 300 North Zeeb Road, Ann Arbor, Ml 48106-1346 USA 800-521-0600 Investigation of natural and synthetic cyanohydrins, insecticidal properties, and their metabolism by Dong-Sik Park A dissertation submitted to the graduate faculty in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Major: Toxicology Program of Study Committee: Joel R. Coats, Major Professor Jon J. Tollefson Gary D. Osweiler Gary J. Atchsion Russell A. Jurenka Iowa State University Ames, Iowa 2002 Copyright © Dong-Sik Park, 2002. All rights reserved. UMI Number: 3073473 UMI UMI Microform 3073473 Copyright 2003 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. B0X1346 Ann Arbor, Ml 48106-1346 ii Graduate College Iowa State University This is to certify that the doctoral dissertation of Dong-Sik Park has met the dissertation requirements of Iowa State University Signature was redacted for privacy. Major Professor Signature was redacted for privacy. For the Major Program iii TABLE OF CONTENTS LIST OF TABLES v LIST OF FIGURES vi ABSTRACT vii ACKNOWLEDGMENTS ix CHAPTER I. CYANOGENIC GLYCOSIDES: ALTERNATIVE INSECTICIDES? I Introduction 1 Distribution and Characteristics of Cyanogenic Glycosides 2 Role of Cyanogenic Glycosides 4 Mode of Action 5 Alternative Insecticides? 5 Acknowledgments 7 References 7 Dissertation Objectives 16 Dissertation Organization 16 CHAPTER 2. FUMIGATION TOXICITY OF VOLATILE NATURAL AND SYNTHETIC CYANOHYDRINS TO STORED-PRODUCT PESTS AND ACTIVITY AS A SOIL FUMIGANT 18 Abstract 18 Introduction 18 Materials and Methods 20 Chemicals 20 Insect Bioassay 20 Soil Fumigation Activity 21 Results and Discussion 24 Insect Fumigation 24 Antimicrobial Activity 25 Inhibition of Weed Seed Germination 25 Acknowledgments 27 References 27 CHAPTER 3. A QSAR EVALUATION OF CYANOHYDRINS' FUMIGATION TOXICITY TO HOUSE FLY {MUSCA DOMESTICA) AND LESSER GRAIN BORER (RHYZOPERTHA DOMINICA) 40 Abstract 40 Introduction 40 Materials and Methods 42 Chemicals 42 Fumigation Toxicity Testing on Two Species 43 iv QSAR Calculations 43 Results and Discussion 44 Conclusions 46 Acknowledgments 46 Literature Cited 46 CHAPTER 4. MODE OF ACTION OF CYANOHYDRINS IN INSECTS 56 Introduction 56 Materials and Methods 57 Chemicals 57 Fumigation Toxicity of Hydrogen Cyanide to House Fly and Lesser Grain Borer 57 Determination of Cyanohydrins in the Headspace of the Chamber and in the C HP-ace-exposed House Fly 58 Concentration of Cyanide Ion in Musca domestica and Rhyzopertha dominion 59 Results 60 Fumigation Toxicity of Hydrogen Cyanide to House Fly and Lesser Grain Borer 60 Cyanohydrins in the Headspace of the Chamber and in the CHP-ace- exposed House Fly 60 Concentration of Cyanide Ion in Musca domesticci and Rhyzopertha dominica 61 Discussion 61 Acknowledgments 63 References 63 CHAPTER 5. GENERAL CONCLUSIONS 70 V LIST OF TABLES CHAPTER 1. CYANOGENIC GLYCOSIDES: ALTERNATIVE INSECTICIDES? Table 1. Fumigation LC# values ~l) of volatile natural and synthetic cyanohydrins. 3 Table 2. The R2 of three parameters to house fly and lesser grain borer. 14 Table 3. Molecular descriptors for cyanohydrins and derivatives. 15 CHAPTER 2. FUMIGATION TOXICITY OF VOLATILE NATURAL AND SYNTHETIC CYANOHYDRINS TO STORED-PRODUCT PESTS AND ACTIVITY AS A SOIL FUMIGANT Table 1. Fumigation LC50 values (ngml "') of volatile natural and synthetic cyanohydrins. 31 Table 2. Fumigation LC50 values (fig-ml "') of cyanohydrins and derivatives. 32 Table 3. Total bacterial count in soil two days following application of CHP-ace. 33 Table 4. Total fungal count in soil two days following application of CHP-ace. 34 Table 5. Number of germinated weed seeds three days after application of CHP-ace. 35 Table 6. Number of germinated weed seeds 24 days after application of CHP-ace. 36 Table 7. Number of germinated weed seeds 10 days after application of chloropicrin. 37 Table 8. Number of germinated weed seeds 10 days after application of 1,3-dichloropropene. 38 Table 9. Severity and number of days microbial activity was depressed by treatment of soil with fumigant. 39 CHAPTER 3. A QSAR EVALUATION OF CYANOHYDRINS' FUMIGATION TOXICITY TO HOUSE FLY {MUSCA DOMESTICA) AND LESSER GRAIN BORER 0RHYZOPERTHA DOMINICA) Table 1. Toxicity and molecular descriptors for 11 cyanohydrins and derivatives and three commercial fumigants. 53 Table 2. The R2 (and cross validation) of three parameters to house fly and lesser grain borer. 54 Table 3. Cross-correlation among the three parameters. 55 CHAPTER 4. MODE OF ACTION OF CYANOHYDRINS IN INSECTS Table 1. Fumigation LC50 values (fig-ml"1) of natural and synthetic cyanohydrins, HCN and commercial fumigants. 67 Table 2. Percentage of cyanohydrin or derivative in the headspace of fumigation chamber. 68 Table 3. Concentration of cyanide ion in insects as |ig CNVg insect body (ppm). 69 vi LIST OF FIGURES CHAPTER 1. CYANOGENIC GLYCOSIDES: ALTERNATIVE INSECTICIDES? Figure 1. Three major cyanogens in plants (I: amygdalin, 2: dhurrin, 3: linamarin). 3 Figure 2. The structure of cyanogenic glycosides, and their metabolism to release hydrogen cyanide (HCN); (1) p-glycosidase, (2) hydroxynitrile lyase. 4 Figure 3. Volatile natural and synthetic cyanohydrins and derivatives. 12 CHAPTER 2. FUMIGATION TOXICITY OF VOLATILE NATURAL AND SYNTHETIC CYANOHYDRINS TO STORED-PRODUCT PESTS AND ACTIVITY AS A SOIL FUMIGANT Figure I. Structures of cyanohydrins and derivatives tested in this study. 30 CHAPTER 3. A QSAR EVALUATION OF CYANOHYDRINS' FUMIGATION TOXICITY TO HOUSE FLY (MUSCA DOMESTIC A) AND LESSER GRAIN BORER (RHYZOPERTHA DOMINICA) Figure 1. Structures of volatile natural and synthetic cyanohydrins and derivatives tested in insect fumigations. 49 Figure 2. Relationships between three parameters and the toxicity of volatile cyanohydrins to the house fly. For the Molar Refractivity figure, three data points are superimposed. 50 Figure 3. Relationships between three parameters and the toxicity of cyanohydrins to the lesser grain borer. For the Polarizability figure, two data points are superimposed. 51 Figure 4. The correlation between the toxicities of volatile cyanohydrins to the house fly and lesser grain borer, using their 24-hr fumigation LC50 values (nmol/ml). 52 CHAPTER 4. MODE OF ACTION OF CYANOHYDRINS IN INSECTS Figure 1. Structures of cyanohydrins and derivatives tested in this study. 64 Figure 2. The standard curve for CHP-ace from a gas chromatograph with a nitrogen-phosphorus detector. 65 Figure 3. Standard calibration curve for cyanide ion with a spectrophotometer. 66 vii ABSTRACT Many of the commercial fumigants, methyl bromide, chloropicrin, dichlorovos, have environmental problems, and some of them will be phased out. New alternative fumigants need to be developed for safety, biodegradability and selectivity. This research investigated fumigation toxicities of natural and synthetic cyanohydrins against stored-product pests and house fly. Using fumigation toxicity of cyanohydrins to the house fly and the lesser grain borer, quantitative structure-activity relationships (QSAR) were determined. For evaluating what components kill the insects, mode of action of cyanohydrins in insects were also conducted. Most natural and synthetic cyanohydrins were as effective as or more effective than commercial fumigants against stored-product pests and the house fly. Log P, polarizability and molar refractivity, which are classical parameters for explaining toxicity, were
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