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The Toxicology
and Biochemistry
of Insecticides
SECOND EDITION

Simon J. Yu
The Toxicology
and Biochemistry
of Insecticides
SECOND EDITION
The Toxicology
and Biochemistry
of Insecticides
SECOND EDITION

Simon J. Yu

Boca Raton London New York

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Taylor & Francis Group, an informa business
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 Contents
Preface to the Second Edition......................................................................................................... xiii
Preface to the First Edition............................................................................................................... xv
Author.............................................................................................................................................xvii

Chapter 1
Need for Pesticides and Their Pattern of Use..................................................................................... 1
1.1 Introduction.............................................................................................................................. 1
1.2 Need for Pesticides................................................................................................................... 1
1.2.1 Food Production.......................................................................................................... 1
1.2.2 World Health Status.................................................................................................... 3
1.3 Pattern of Use........................................................................................................................... 4
1.4 Pesticide Economics.................................................................................................................7
References........................................................................................................................................... 8

Chapter 2
Formulation of Pesticides....................................................................................................................9
2.1 Introduction.............................................................................................................................. 9
2.2 Types of Formulation...............................................................................................................9
2.2.1 Dusts...........................................................................................................................9
2.2.2 Wettable Powders...................................................................................................... 10
2.2.3 Emulsifiable Concentrates........................................................................................ 10
2.2.4 Suspendable Concentrates or Flowables................................................................... 10
2.2.5 Water-Soluble Powders............................................................................................. 10
2.2.6 Solutions.................................................................................................................... 11
2.2.7 Granules.................................................................................................................... 11
2.2.8 Water-Dispersible Granules...................................................................................... 11
2.2.9 Ultralow-Volume Formulations................................................................................ 11
2.2.10 Aerosols.................................................................................................................... 12
2.2.11 Controlled-Release Formulations............................................................................. 12
2.2.12 Baits.......................................................................................................................... 13
2.3 Nonpesticidal Ingredients of Formulations............................................................................ 14
2.3.1 Solvents..................................................................................................................... 14
2.3.2 Diluents..................................................................................................................... 15
2.3.3 Surfactants................................................................................................................ 15
2.4 Disposal of Pesticide Containers........................................................................................... 17
2.5 Pesticide Application Equipment........................................................................................... 18
References......................................................................................................................................... 18

Chapter 3
Pesticide Laws and Regulations........................................................................................................ 21
3.1 Introduction............................................................................................................................ 21
3.2 Federal Insecticide, Fungicide, and Rodenticide Act............................................................. 21
3.2.1 Registration of Pesticides.......................................................................................... 21
3.2.2 Classification of Pesticides and Certification of Applicators....................................25

v
vi Contents

3.2.3 Other Provisions of FIFRA......................................................................................25

3.2.3.1 Experimental Use Permits.........................................................................25
3.2.3.2 Review and Suspension.............................................................................25
3.2.3.3 Registration of Establishments..................................................................26
3.2.3.4 Unlawful Acts...........................................................................................26
3.2.3.5 Penalties....................................................................................................26
3.2.3.6 Rights to Data............................................................................................26
3.2.3.7 Special Review..........................................................................................26
3.2.4 Pesticide Categories..................................................................................................26
3.3 Federal Food, Drug, and Cosmetic Act................................................................................. 27
3.3.1 Tolerance................................................................................................................... 27
3.3.2 Basis for Tolerance.................................................................................................... 27
3.4 Food Quality Protection Act.................................................................................................. 27
3.5 State Laws..............................................................................................................................28
3.6 Enforcement........................................................................................................................... 29
References......................................................................................................................................... 29

Chapter 4
Classification of Insecticides............................................................................................................ 31
4.1 Introduction............................................................................................................................ 31
4.2 Classification of Insecticides.................................................................................................. 31
4.2.1 Chlorinated Hydrocarbon Insecticides..................................................................... 31
4.2.1.1 DDT Group............................................................................................... 31
4.2.1.2 Chlorinated Cyclic Compounds................................................................ 33
4.2.2 Organophosphates..................................................................................................... 35
4.2.2.1 Phosphates................................................................................................. 35
4.2.2.2 Phosphorothioates..................................................................................... 37
4.2.2.3 Phosphorodithioates.................................................................................. 39
4.2.2.4 Phosphorothiolates.................................................................................... 42
4.2.2.5 Phosphonates............................................................................................. 42
4.2.2.6 Phosphoramidates..................................................................................... 43
4.2.3 Carbamates...............................................................................................................44
4.2.4 Pyrethroids................................................................................................................ 50
4.2.5 Botanical Insecticides............................................................................................... 58
4.2.5.1 Nicotine..................................................................................................... 58
4.2.5.2 Rotenone.................................................................................................... 59
4.2.5.3 Azadirachtin.............................................................................................. 59
4.2.5.4 Sabadilla.................................................................................................... 59
4.2.5.5 Ryania........................................................................................................60
4.2.6 Insect Growth Regulators.........................................................................................60
4.2.6.1 Juvenoids (Juvenile Hormone Mimics).....................................................60
4.2.6.2 Benzoylphenylureas (Acylureas)............................................................... 62
4.2.6.3 Diacylhydrazines.......................................................................................66
4.2.6.4 Triazines....................................................................................................66
4.2.6.5 Thiadiazines.............................................................................................. 67
4.2.7 Neonicotinoids.......................................................................................................... 67
Contents vii

4.2.8 Formamidines........................................................................................................... 69
4.2.9 Microbial Insecticides............................................................................................... 70
4.2.9.1 Bacteria...................................................................................................... 70
4.2.9.2 Fungi.......................................................................................................... 77
4.2.9.3 Baculoviruses............................................................................................ 77
4.2.9.4 Protozoa..................................................................................................... 78
4.2.10 Fumigants................................................................................................................. 78
4.2.11 Inorganic Insecticides...............................................................................................80
4.2.12 Miscellaneous Insecticide Classes............................................................................80
4.2.12.1 Amidinohydrazones..................................................................................80
4.2.12.2 Phenylpyrazoles (Fiproles)........................................................................80
4.2.12.3 Pyrazoles................................................................................................... 81
4.2.12.4 Pyrroles..................................................................................................... 82
4.2.12.5 Oxadiazines............................................................................................... 82
4.2.12.6 Sulfonamides............................................................................................. 83
4.2.12.7 Pyridazinones............................................................................................ 83
4.2.12.8 Nereistoxin Analogs..................................................................................84
4.2.12.9 Pyridine Azomethines............................................................................... 85
4.2.12.10 Pyrimidinamines....................................................................................... 85
4.2.12.11 Trifluoromethylnicotinamides................................................................... 86
4.2.12.12 Diamides................................................................................................... 86
4.2.12.13 Dichloropropenyl Ethers........................................................................... 87
4.2.12.14 Tetronic Acids........................................................................................... 88
4.2.12.15 Tetramic Acids.......................................................................................... 88
4.2.12.16 Semicarbazones......................................................................................... 89
4.2.12.17 Quinazolinones......................................................................................... 89
4.2.12.18 Sulfoximines.............................................................................................90
4.2.12.19 Pesticidal Oils and Soaps..........................................................................90
4.2.13 Acaricides.................................................................................................................90
4.2.13.1 Organosulfurs............................................................................................90
4.2.13.2 Inorganics.................................................................................................. 91
4.2.13.3 Organotins................................................................................................. 91
4.2.13.4 Pyrazoles...................................................................................................92
4.2.13.5 Quinazolines.............................................................................................92
4.2.13.6 Methoxyacrylates...................................................................................... 93
4.2.13.7 Naphthoquinones....................................................................................... 93
4.2.13.8 Tetronic Acids...........................................................................................94
4.2.13.9 Tetrazines..................................................................................................94
4.2.13.10 Oxazoles.................................................................................................... 95
4.2.13.11 Carbazates................................................................................................. 95
4.2.13.12 Benzoylacetonitriles (Acylacetonitriles)................................................... 95
4.2.13.13 Trifluoromethanesulfonanilides................................................................96
4.2.13.14 Bridged Diphenyls.....................................................................................96
4.2.13.15 Thiazolidines.............................................................................................96
4.2.13.16 Quinoxalines.............................................................................................97
4.2.13.17 Pyrethroid Ethers......................................................................................97
4.2.13.18 Thiocarbamates.........................................................................................97
4.2.13.19 Monoterpenoids......................................................................................... 98
viii Contents

4.2.14 Insect Repellents....................................................................................................... 98

4.2.14.1 Synthetic Insect Repellents....................................................................... 98
4.2.14.2 Botanical Insect Repellents.......................................................................99
References....................................................................................................................................... 100

Chapter 5
Evaluation of Toxicity..................................................................................................................... 103
5.1 Introduction.......................................................................................................................... 103
5.2 Testing Procedures............................................................................................................... 103
5.3 Tests with Insects................................................................................................................. 104
5.3.1 Topical Application................................................................................................. 104
5.3.2 Injection Method..................................................................................................... 104
5.3.3 Dipping Method...................................................................................................... 105
5.3.4 Contact Method (Residual Exposure Method)....................................................... 105
5.3.5 Fumigation Method................................................................................................. 106
5.3.6 Feeding Method...................................................................................................... 106
5.4 Tests with Higher Animals.................................................................................................. 107
5.4.1 Acute Toxicity Tests................................................................................................ 107
5.4.2 Subacute Toxicity and Chronic Toxicity Tests........................................................ 107
5.5 Probit Analysis..................................................................................................................... 107
5.6 Source of Variability in Dose–Response Tests.................................................................... 111
5.6.1 Age.......................................................................................................................... 111
5.6.2 Sex........................................................................................................................... 112
5.6.3 Rearing Temperature.............................................................................................. 112
5.6.4 Food Supply............................................................................................................ 112
5.6.5 Population Density.................................................................................................. 113
5.6.6 Illumination............................................................................................................ 113
5.7 Use of LDP Lines................................................................................................................. 113
Appendix 5.A.................................................................................................................................. 116
References....................................................................................................................................... 120

Chapter 6
Uptake of Insecticides..................................................................................................................... 123
6.1 Introduction.......................................................................................................................... 123
6.2 Penetration of Insecticides through the Insect Cuticle........................................................ 123
6.2.1 Structure of Insect Cuticle...................................................................................... 123
6.2.2 Movement of Insecticides through the Cuticle....................................................... 123
6.2.3 Site of Entry............................................................................................................ 124
6.2.4 Factors Affecting Cuticular Penetration Rates....................................................... 126
6.2.4.1 Effect of Solvent...................................................................................... 126
6.2.4.2 Polarity of Insecticides............................................................................ 127
6.2.4.3 Cuticular Composition............................................................................ 128
6.2.5 Metabolism of Insecticides in the Cuticle............................................................... 128
6.3 Entry via the Mouth............................................................................................................. 128
6.4 Uptake via the Spiracles....................................................................................................... 129
References....................................................................................................................................... 130
Contents ix

Chapter 7
Mode of Action of Insecticides....................................................................................................... 133
7.1 Introduction.......................................................................................................................... 133
7.2 Insecticides Affecting Voltage-Gated Sodium Channels.................................................... 133
7.2.1 Background............................................................................................................. 133
7.2.2 Mode of Action of the DDT Group, Pyrethroids, Indoxacarb, Sabadilla,
and Metaflumizone................................................................................................. 137
7.3 Insecticides Affecting Ryanodine Receptors....................................................................... 139
7.4 Insecticides Inhibiting Acetylcholinesterase....................................................................... 141
7.4.1 Background............................................................................................................. 141
7.4.2 Mode of Action of Organophosphorus and Carbamate Insecticides...................... 143
7.5 Insecticides Interfering with Chloride Channels................................................................. 147
7.5.1 GABA-Gated Chloride Channels........................................................................... 147
7.5.2 Glutamate-Gated Chloride Channels..................................................................... 149
7.6 Insecticides That Bind to Nicotinic Acetylcholine Receptors............................................. 150
7.7 Insecticides Affecting Octopamine Receptors.................................................................... 153
7.8 Insecticides Interfering with Respiration............................................................................. 154
7.8.1 Inhibitors of the Mitochondrial Electron Transport System................................... 154
7.8.2 Inhibitors of Oxidative Phosphorylation................................................................. 155
7.9 Insecticides Disrupting Insect Midgut Membranes............................................................. 155
7.9.1 Bacillus thuringiensis............................................................................................. 155
7.9.2 Bacillus sphaericus................................................................................................. 157
7.10 Mode of Action of Baculovirus Insecticides........................................................................ 157
7.11 Insecticides Affecting Chitin Biosynthesis or Cuticle Sclerotization.................................. 157
7.12 Insecticides Acting as Juvenile Hormone Mimics............................................................... 160
7.13 Insecticides Acting as Ecdysone Agonists or Blocking Molting Hormone Activity........... 162
7.14 Insecticides Causing Protein Degradation and Necrotic Cell Death................................... 163
7.15 Insecticides Abrading or Disrupting Insect Cuticle............................................................. 163
7.16 Insecticides Acting as Selective Feeding Blockers.............................................................. 163
7.17 Insecticides Causing Suffocation......................................................................................... 164
7.18 Mode of Action of Acaricides.............................................................................................. 164
7.18.1 Acaricides Interfering with Respiration................................................................. 164
7.18.2 Acaricides Interfering with Growth and Development........................................... 165
7.18.3 Acaricides Acting as Neurotoxins.......................................................................... 166
7.19 Mode of Action of Insect Repellents.................................................................................... 166
References....................................................................................................................................... 167

Chapter 8
Principles of Pesticide Metabolism................................................................................................. 175
8.1 Introduction.......................................................................................................................... 175
8.2 Phase I Reactions................................................................................................................. 176
8.2.1 Oxidation................................................................................................................ 176
8.2.2 Hydrolysis............................................................................................................... 182
8.2.3 Reduction................................................................................................................ 184
8.3 Phase II Reactions................................................................................................................ 185
8.3.1 Glucose Conjugation............................................................................................... 186
8.3.2 Glucuronic Acid Conjugation................................................................................. 186
x Contents

8.3.3 Sulfate Conjugation................................................................................................. 187

8.3.4 Phosphate Conjugation............................................................................................ 187
8.3.5 Amino Acid Conjugation........................................................................................ 187
8.3.6 Glutathione Conjugation......................................................................................... 188
8.4 Metabolic Systems in Plants................................................................................................ 192
8.5 Metabolic Pathways of Selected Insecticides....................................................................... 192
8.5.1 Carbamates............................................................................................................. 193
8.5.2 Organophosphates................................................................................................... 195
8.5.3 Pyrethroids.............................................................................................................. 197
8.5.4 Chlorinated Hydrocarbons...................................................................................... 199
8.5.5 Benzoylphenylureas................................................................................................ 199
8.5.6 Juvenoids.................................................................................................................200
8.5.7 Neonicotinoids........................................................................................................200
8.5.8 Formamidines......................................................................................................... 203
8.5.9 Amidinohydrazones................................................................................................205
8.5.10 Phenylpyrazoles......................................................................................................205
8.5.11 Thiadiazines............................................................................................................205
8.5.12 Triazines..................................................................................................................205
8.5.13 Quinazolines...........................................................................................................207
8.5.14 Organotins...............................................................................................................207
8.5.15 Microbial Insecticides.............................................................................................208
8.5.16 Diacylhydrazines....................................................................................................209
8.5.17 Nereistoxin Analogs................................................................................................209
8.5.18 Thiocarbamates.......................................................................................................209
8.5.19 Organosulfurs......................................................................................................... 211
8.5.20 Pyrazoles................................................................................................................. 211
8.5.21 Phthalic Acid Diamides.......................................................................................... 211
8.5.22 Anthranilic Diamides............................................................................................. 212
8.5.23 Tetronic Acids......................................................................................................... 212
8.5.24 Dichloropropenyl Ethers......................................................................................... 215
References....................................................................................................................................... 216

Chapter 9
Species Differences and Other Phenomena Associated with the Metabolism
of Xenobiotics.......................................................................................................................221
9.1 Introduction.......................................................................................................................... 221
9.2 Species Differences in Detoxification Enzyme Activity..................................................... 221
9.2.1 Examples of Differences......................................................................................... 221
9.2.2 Evolution of Species Differences in Detoxification................................................ 227
9.3 Effect of Age and Sex on Enzyme Activity......................................................................... 228
9.4 Specificity of Detoxification Enzymes................................................................................. 231
9.5 Selective Toxicity................................................................................................................. 233
9.6 Synergism and Antagonism................................................................................................. 241
9.7 Enzyme Induction................................................................................................................ 245
9.7.1 Induction of Detoxification Enzymes..................................................................... 245
9.7.1.1 Cytochrome P450 Monooxygenases....................................................... 245
9.7.1.2 Glutathione S-Transferases...................................................................... 247
9.7.1.3 Esterases and Reductases........................................................................ 249
9.7.2 Enzyme Induction as Detoxification Mechanism................................................... 249
Contents xi

9.8 Insecticide Resistance.......................................................................................................... 251

References....................................................................................................................................... 251

Chapter 10
Insecticide Resistance..................................................................................................................... 257
10.1 Introduction.......................................................................................................................... 257
10.2 Genetics of Resistance......................................................................................................... 258
10.2.1 Preadaptation.......................................................................................................... 258
10.2.2 Gene Frequency......................................................................................................260
10.2.3 Dominance and Number of Genes.......................................................................... 261
10.2.3.1 Monogenic Inheritance...........................................................................264
10.2.3.2 Polygenic Inheritance..............................................................................264
10.2.4 Reversion of Resistance..........................................................................................266
10.3 Mechanisms of Resistance................................................................................................... 268
10.3.1 Behavioral Resistance............................................................................................. 268
10.3.2 Physiological Resistance......................................................................................... 268
10.3.2.1 Reduced Penetration................................................................................ 269
10.3.2.2 Target Site Insensitivity........................................................................... 269
10.3.2.3 Increased Detoxification.......................................................................... 276
10.4 Interaction Phenomena......................................................................................................... 282
10.4.1 Cross-Resistance and Multiple Resistance............................................................. 282
10.4.2 Interaction of Resistance Factors............................................................................284
10.4.3 Fitness Costs of Insecticide Resistance.................................................................. 285
10.4.3.1 Resistance to Organophosphorus and Carbamate Insecticides............... 286
10.4.3.2 Resistance to Pyrethroid Insecticides..................................................... 286
10.4.3.3 Resistance to Microbial Insecticides....................................................... 286
10.4.3.4 Resistance to Chlorinated Hydrocarbon Insecticides............................. 287
10.4.3.5 Resistance to Insect Growth Regulators................................................. 288
10.4.3.6 Resistance to Neonicotinoid Insecticides................................................ 288
10.4.3.7 Resistance to Miscellaneous Insecticides and Multiple Resistance........ 288
10.4.3.8 Association between Fitness Disadvantage and Resistance
Mechanism.............................................................................................. 289
10.5 Rate of Development of Resistance..................................................................................... 291
10.5.1 Frequency of R Alleles........................................................................................... 292
10.5.2 Dominance of R Alleles.......................................................................................... 292
10.5.3 Generation Turnover............................................................................................... 292
10.5.4 Population Mobility................................................................................................ 293
10.5.5 Persistence of Pesticide Residues............................................................................ 294
10.5.6 Selection Pressure................................................................................................... 294
10.6 Pattern of Resistance Development...................................................................................... 295
10.7 Management of Resistance.................................................................................................. 295
10.7.1 Reducing Resistance Gene Frequency.................................................................... 296
10.7.2 Use of Insecticide Mixtures and Rotations............................................................. 296
10.7.3 Use of Insecticide Synergists.................................................................................. 298
10.7.4 Use of New Pesticides.............................................................................................300
10.7.5 Use of Resistant Predators and Parasites................................................................ 301
10.7.6 Field Monitoring.....................................................................................................302
10.7.7 Use of Transgenic Crops......................................................................................... 303
References.......................................................................................................................................304
xii Contents

Chapter 11
Pesticides in the Environment......................................................................................................... 323
11.1 Introduction.......................................................................................................................... 323
11.2 Persistence of Pesticides in Soil........................................................................................... 323
11.2.1 Adsorptive Forces................................................................................................... 323
11.2.1.1 Chemical Bonding................................................................................... 323
11.2.1.2 Physical Binding...................................................................................... 324
11.2.1.3 Hydrogen Bonding.................................................................................. 324
11.2.2 Factors Influencing Persistence of Pesticides in Soil.............................................. 324
11.2.2.1 Soil Type.................................................................................................. 325
11.2.2.2 Nature of the Pesticide............................................................................ 326
11.2.2.3 Soil Moisture........................................................................................... 326
11.2.2.4 Soil pH..................................................................................................... 326
11.2.2.5 Soil Temperature..................................................................................... 327
11.2.2.6 Microbial Degradation............................................................................ 327
11.3 Photodegradation of Pesticides............................................................................................ 331
11.3.1 Hydrolysis............................................................................................................... 335
11.3.2 Dechlorination........................................................................................................ 335
11.3.3 Oxidation................................................................................................................ 335
11.3.4 Isomerization (Intramolecular Rearrangement Process)........................................ 335
11.4 Pesticides and the Food Chain............................................................................................. 336
11.4.1 Lipid Solubility of Pesticides.................................................................................. 338
11.4.2 Metabolic Activity.................................................................................................. 339
11.4.3 Feeding Habits........................................................................................................ 339
11.4.4 Behavior and Ecological Niche............................................................................... 339
11.5 Sublethal Effects of Pesticides on Wildlife..........................................................................340
11.5.1 Eggshell Thinning in Birds.....................................................................................340
11.5.2 Endocrine Disruption in Wildlife........................................................................... 341
11.5.3 Biomarkers as Indicators of Pesticide Pollution..................................................... 342
References.......................................................................................................................................344
 Preface to the Second Edition
It has been six years since the first edition of this book was published. During this period, numer-
ous new discoveries have been made in the field of insecticide toxicology, which justify inclusion
in this book. Furthermore, many colleagues have used the first edition as a textbook for teaching
insecticide toxicology. They have also given me some valuable suggestions to improve the book. In
this new edition, I have retained the original format, but each chapter has been revised and updated,
some quite extensively. In response to the reviewer’s comments on the first edition, new references
are added to each chapter for further reading. The following are some of the new features.
In Chapter 1, the introductory chapter, because of the potentially adverse effects of insecticides,
some balance has been provided (i.e., the mention of human health hazards and ­environmental
insults). In Chapter 2, the procedures for disposing pesticide containers are described. In Chapter 3,
the new pollinator protective labeling for neonicotinoid insecticides is added. These label changes
include a “Pollinator Protection Box” following the Environmental Hazards section as well as the
new pollinator language in the Directions for Use section of each label.
In Chapter 4, several newly developed insecticides/acaricides (e.g., sulfoxaflor, cyenopyrafen,
and cyflumetofen) are described, including their classification and biological activity. In addition,
more microbial insecticides (bacteria, fungi, baculoviruses, and protozoa) are added in order to
be in line with current integrated pest management (IPM) approaches. Various insect repellents,
including synthetic chemicals and botanical products, are also presented.
In Chapter 7, the newly discovered modes of action of insecticides are described. For example,
avermectin and fipronil act as blockers of glutamate-gated chloride channels. Pymetrozine exerts
its repellent action by binding at nAChR sites. The diamide insecticides (chlorantraniliprole and
cyantraniliprole) and ryanodine activate the ryanodine receptor, but they bind at different allosteri-
cally coupled sites. The mode of action of baculoviral insecticides and insect repellents are also
described. Moreover, the known symptoms of insecticide poisoning in mammals are described.
In Chapter 8, the topic of metabolic pathways of insecticides has been expanded to include
new classes of insecticides: formamidines, amidinohydrazones, phenylpyrazoles, thiadiazines,
triazines, quinazolines, organotins, microbial insecticides, diacylhyrazines, nereistoxin ­analogs,
­thiocarbamates, organosulfurs, pyrazoles, diamides, tetronic acids, and dichloropropenyl ethers.
This knowledge is important for assessing residual hazards to humans as well as studying
­mechanisms of insecticide resistance in insects. Furthermore, the structure of ATP-binding cassette
transporter (also known as ABC transporter) and its role in xenobiotic metabolism are described.
In Chapter 9, the topic of insecticide selectivity has been expanded to include (1) the selectiv-
ity of pyrethroids, oxidizones, diamides, Bt, and diacylhydrazines, and (2) the toxicity of various
insecticide classes on arthropod natural enemies of agricultural pests. The latter is an important
consideration in IPM programs.
In Chapter 10, insecticide resistance has been updated and greatly expanded. These include (1) a
discussion on the mechanisms of the reversion of insecticide resistance in the absence of ­insecticide
pressure; (2) new mechanisms of insecticide resistance, such as mutations in the mitochondrial
­electron transport chain and chitin synthase, gene amplification of cytochrome P450 ­monooxygenases,
­chimeric P450s, and ABC transporter–mediated resistance; (3) the pattern of resistance development;
and (4) fitness costs of insecticide resistance in insects. Due to the problem of insecticide resistance
coupled with the slowdown in the development of new insecticides, insecticide resistance manage-
ment has become more important as a means to preserve existing insecticides.
In Chapter 11, the topic of microbial degradation has been expanded to include (1) bioremedia-
tion of pesticide pollution in the environment and (2) symbiont-mediated insecticide tolerance. Also
included are certain synthetic pyrethroid and organophosphorus insecticides, which have recently
been found to possess hormone agonist and antagonist activities.

xiii
xiv Preface to the Second Edition

I hope this new edition will be useful to students of entomology, plant medicine, pest manage-
ment, and other disciplines related to agriculture. I also hope that this book will be used as a text-
book for teaching insecticide toxicology to graduate students.
I wish to thank my editor, John Sulzycki, and project coordinator, Jill Jurgensen, at CRC Press,
Taylor & Francis Group, for their valuable assistance. Finally, I thank my wife, Rachel, for her con-
tinued support and patience during this revision.

Simon J. Yu
 Preface to the First Edition
There is a scarcity of textbooks in insect toxicology and most of these books are rather outdated.
I have written this book to address the need for a current text, and to provide the student of entomol-
ogy, crop protection, plant medicine, and other disciplines related to agriculture with the general
knowledge of insecticides. The book also brings together the most current knowledge on insecticide
action and use. The 11 chapters in this book are concerned with insecticide formulation, classifica-
tion, bioassay, mode of action, biotransformations in living organisms, resistance in insects, impact
on the environment, and the laws that regulate their use. Since we are dealing with chemical com-
pounds and their interaction with living organisms, my approach to most of these subjects is through
chemical and biochemical principles. With the advent of molecular biology, numerous new findings
have been reported in the areas of insecticide action and resistance mechanisms at the gene level.
Although these subjects are not covered in much detail, the discussions are thorough enough for the
serious reader to continue his or her study with more advanced literature.
Pesticides are an important component in pest management strategies for food production and
public health. Despite their importance, these chemicals are often blamed for environmental pol-
lution and nontarget toxicities. In fact, few other chemicals commonly used by our society are
more closely scrutinized. Moreover, insects can develop resistance with frequent applications of
pesticides. All of these issues have changed pest control from the simple task of the olden days into
the complex, publicly sensitive operation of today. People who develop and supervise modern pest
control methods must be highly trained in many areas of pesticide usage. Therefore, in order to use
pesticides safely and effectively, not only must we know which pesticides to use in specific condi-
tions, but we must also understand all biological, physiological, and environmental consequences.
I hope this book will provide students with sufficient background for the future use of pesticides
and that it will prove valuable to all who are interested in pesticides.
The format of this book is based primarily on the late Professor L.C. Terriere’s unpublished
teaching material entitled “The Biochemistry and Toxicology of Insecticides” (1982). We talked
about the possibility of coauthoring a new textbook in insecticide toxicology because of the clear
need for such material. Unfortunately, he passed away before it could materialize. I dedicate this
book to Professor Terriere in appreciation of his valuable contributions to insect toxicology and
biochemistry, and the many years of research association.
I thank Drs. S.M. Valles, E. McCord, Jr., M.E. Scharf, L.T. Ou, and three anonymous review-
ers for reviewing the manuscript and providing much helpful advice. I thank Susan Duser, Mike
Sanford, and Sam Nguyen, who made many excellent computer drawings and figures. Thanks also
to my editor, John Sulzycki, and project coordinator, Patricia Roberson, at Taylor & Francis Group,
LLC, for their valuable assistance. Finally, I thank my wife, Rachel, for her mental support, and my
sons, Robert and Edmund, for their help.

Simon J. Yu

xv
 Author
Simon J. Yu (Simon S.J. Yu), PhD, is professor emeritus at the University of Florida in Gainesville.
He earned his BS in entomology from National Taiwan University, Taiwan, and an MS and a PhD
in entomology from McGill University in Montreal, Canada, where he specialized in insect toxi-
cology. After completing postdoctoral studies at Cornell University and Oregon State University,
he served as assistant professor at Oregon State University from 1974 to 1979. He moved to the
University of Florida in 1980. He was promoted to associate professor in 1982 and professor in 1986.
He retired from the university in 2006, but remains an emeritus faculty. Dr. Yu’s research interests
include detoxification mechanisms, insecticide resistance, and enzyme induction in insects. His
research has been supported by the USDA, NSF, NIH, EPA, and various pesticide companies. He
has published more than one hundred scientific papers in various refereed journals and seven book
chapters pertaining to insect toxicology. He has also published a textbook entitled The Toxicology
and Biochemistry of Insecticides, 1st edition (2008) and 2nd edition (2014), CRC Press. He has
presented over 50 papers at scientific meetings. He served as the major professor for MS and PhD
students and supervisor for postdoctoral associates. He also taught a graduate course in insect toxi-
cology in the Entomology/Nematology Department. Since his retirement, he continues to teach
a course in insect toxicology, in distance education form, to off-campus graduate students.

xvii
 Chapter 1

Need for Pesticides and Their Pattern of Use

1.1 INTRODUCTION

Pesticides are chemical substances used for controlling pests. The Environmental Protection
Agency (EPA), which is the primary regulator of pesticides in the United States, defines a pesticide
more precisely: A pesticide is any substance or mixture of substances intended for preventing,
destroying, repelling, or mitigating any pest. Pesticides include insecticides, nematicides, rodenti-
cides, herbicides, and fungicides. They are the largest group of poisonous substances that are widely
broadcast today. There are approximately 1,200 active ingredients approved for use by the EPA from
which over 20,000 pesticides products are formulated and are being marketed in the United States.
The world population reached 7 billion in 2011 and is estimated to reach 8.04 billion by the year
2025. To properly feed and clothe these additional people, food crop yields need to be increased
and more natural fibers produced. It is projected that global food demand will double in the next
50 years. Agricultural experts believe that these food and fiber needs can be met, but to do so will
require the increased use of pesticides.
It should be mentioned that most pesticides, especially insecticides, are not highly selective.
They are generally toxic to various nontarget species, including humans. Thus, we must use these
chemicals carefully and scientifically in order to minimize their exposure to nontarget organisms.
Insecticide application is not always efficient. For example, it has been estimated that in an
aerial spray of insecticide, 45% of the insecticide reaches an infested crop and less than 4% of the
insecticide actually reaches the insect pest (Von Rumker et al., 1975). In this case, more than 50%
of the insecticide reaches off-target crop; such insecticide is wasted and will pollute the e­ nvironment.
Therefore, the use of pesticides must take into consideration a balance between benefits of pest
control and risks to human health and the environment.

1.2 NEED FOR PESTICIDES

1.2.1 Food Production

One of the major benefits of pesticides is the protection of crop yields. According to the National
Research Council (2000), removing pesticides from U.S. agriculture would cause crop production to
decline as much as 50%, depending on the crop species. Moreover, farm exports would decrease by
50%, and consumer expenditures for food would increase—and be accompanied by an increase in
inflation—as food prices increase. It was concluded that chemical insecticides should remain part of
a larger toolbox of diverse pest management tactics in the foreseeable future. More recently, Richard
(2010) found that in the United Kingdom, without the application of pesticides to control insects, dis-
ease, and weeds, crop yields would fall to half their current levels and food prices would rise by 40%.

1
2 THE Toxicology and Biochemistry of Insecticides

According to Ware and Whitacre (2004), about one-third of the world’s food crops are destroyed
by pests during growth, harvesting, and storage. Losses are even higher in developing countries.
For example, in Latin America, approximately 40% of crops are lost due to pests. Cocoa produc-
tion in Ghana has been tripled by the use of insecticides to control just one insect pest species.
Sugar production in Pakistan was increased one-third due to the use of insecticides. The Food
and Agriculture Organization has estimated that 50% of cotton production in developing countries
would be destroyed without the use of insecticides. In the United States alone, crop losses due to
pests are estimated to be 30% or $33 billion annually.
What would the losses be without pesticides? The need for controlling pests varies with the pest
situations and with the crop. There are some crops that could not be produced if insects and diseases
were not controlled. As shown in Table 1.1, wheat in the untreated sample was totally destroyed by
wheat mites. There are some others that would survive but would produce poor quality, and there
are still others where the control of pests provides only marginal benefits. There is no doubt that
pesticides increase the profits of farmers by reducing the need for hand labor, increasing yields,
assisting in the management of harvests, preventing losses in storage, and providing a more salable
product (Terriere, 1982). It has been estimated that the farmer received approximately $4 in return
for every dollar spent on pesticides (Pimentel et al., 1992).
A recent study shows that approximately 45 million acres of the United States (under 2% of the
total acreage) are treated with insecticides each year to control insect pests. For some crops, losses

Table 1.1  omparison of Losses Caused by Insects in Plots Treated by

C
Conventional Use of Insecticides and Untreated Plots
Calculated Losses (%)
Without Increased
Commodity With Treatment Treatment Yield (%)
Corn
Southwestern corn borer 9.9 34.3 24.4
Leafhopper on silage corn 38.3 76.6 38.4
Corn rootworm 5.0 15.7 10.7
Soybean
Mexican bean beetle 0.4 26.0 25.6
Stink bugs 8.5 15.0 6.5
Velvet bean caterpillar 2.4 16.6 14.2
Looper caterpillar 10.5 25.5 15.0
Wheat
Brown wheat mite 21.0 100.0 79.0
Cutworms 7.7 54.7 47.0
Wheat grubs 9.3 39.0 29.7
Cotton
Boll weevil 19.0 30.9 11.9
Bollworm 12.1 90.8 78.7
Pink bollworm 10.0 25.5 15.5
Thrips 16.7 57.0 40.3
Potato
Colorado potato beetle 1.0 46.6 45.6
European corn borer 1.5 54.3 52.8
Potato leafhopper 0.4 43.2 42.8
Source: From Ware, G.W. and Whitacre, D.M., The Pesticide Book, 6th edn, MeisterPro
Information Resources, Willoughby, OH, 2004, p. 12. With permission.
Need for Pesticides and Their Pattern of Use 3

would be higher than 40%. Many crops would not be economically feasible without the use of
insecticides, which costs $1.2 billion annually (Mossler et al., 2009). According to the CropLife
Foundation (2007), insecticides are a necessity in crop protection. In the United States, more than
144 billion pounds of crops would be lost annually without the insecticide protection.

1.2.2 World Health Status

As shown in Table 1.2, many diseases can be transmitted to humans by insects, ticks, or
mites. It has been documented by the World Health Organization and in other reports that
the use of synthetic insecticides can markedly reduce the risk of insect-borne diseases, espe-
cially in the case of malaria (Nauren, 2007). According to Ware and Whitacre (2004), in 1955,
malaria infected more than 200 million persons throughout the world. The use of insecticides
has reduced the annual death rate from this disease from 6 million in 1939 to 2.5 million in
1965 to about 1 ­m illion in 1991. Because of the use of insecticides, similar progress has been
made in controlling other important tropical diseases including yellow fever, sleeping sickness,
and Chagas’ disease. Presently, we face the danger of contracting such diseases as encephali-
tis, typhus, relapsing fever, and sleeping s­ ickness. Furthermore, in recent years, probably the
increased movement of people (modern air transport) has brought a new insect-borne disease
to North America. The West Nile virus (WNV), first reported in New York State in 1999, has
spread over the Unites States. In 2002, there were 3900 human cases of WNV, which caused
247 deaths in the United States. The virus, believed to be spread by mosquitoes, also infests
domestic livestock and many other wildlife species.

Table 1.2  ome of the Most Common Diseases Known to Be

S
Transmitted to Humans by Insects, Ticks, or Mites
Disease Vector
African sleeping sickness Tsetse flies
Anthrax Horse flies
Bubonic plague A rat flea
Dengue fever Two mosquitoes
Dysenteries Several flies
Encephalitides Several mosquitoes
Endemic typhus Oriental rat flea
Epidemic typhus Human louse
Filariasis Several mosquitoes
Hemorrhagic fevers Several mites and ticks
Lyme disease Ixodes spp. ticks
Malaria Anopheles mosquitoes
Onchocerciasis Several black flies
Leishmaniasis Sandflies
Q fever Ticks
Relapsing fevers Several ticks
Rocky Mountain spotted fever Two ticks
St. Louis encephalitis Culex pipiens
Trypanosomiasis Several flies
West Nile virus Several mosquitoes
Yellow fever Several mosquitoes
Source: Adapted from Ware, G.W. and Whitacre, D.M., The Pesti­
cide Book, 6th edn, MeisterPro Information Resources,
Willoughby, OH, 2004. With permission.
4 THE Toxicology and Biochemistry of Insecticides

Among the household insect pests, cockroaches are associated with the incidence of bronchial
asthma, particularly, in children. Cockroach’s body parts, cast skin, egg shells, and fecal material
contain several major and minor allergens involved in triggering an asthma attack (Helm et al.,
1996; Yu and Huang, 2000). A majority of urban residents with asthma are sensitive to cockroach
allergens. The fact that the number of cockroaches seen in the infested housing is correlated with
the degree of cockroach sensitivity suggests that cockroach control could reduce the incidence of
asthma (National Research Council, 2000).
From this information, it is clear that efforts to control these diseases will continue and that
pesticides will constitute a major part of such efforts.

1.3 PATTERN OF USE

Pesticides are widely used in the world and on most major crops, although the percentage of
each crop treated throughout the world is low. As shown in Table 1.3, in the United States, pesticide
amount used was 1.1 billion pounds in 2007, which accounted for 22% of the world estimate of
5.2 billion pounds of pesticide use, 25% of world herbicide amount used, 10% of world insecti-
cide amount used, 14% of world fungicide amount used, and 26% of other pesticide amount used
(Grube et al., 2011). In 2007, the agricultural market consumed 80% of the conventional pesticides
(684 million pounds totally) sold in the United States (Table 1.4). Industry and government used
12%, while home and garden consumed only 8%. The industrial and commercial categories include
applications of pesticides used by pest control operators, turf and sod producers, floral and shrub
nurseries, railroads, highways, and industrial plant sites. Government use includes federal and state
pest suppression and eradication programs and municipal and state health protection efforts involv-
ing the control of disease vectors such as mosquitoes, flies, cockroaches, and rodents. This table
also shows that 11% of the pesticides are used as insecticides/miticides, 62% as herbicides/plant
growth regulators, and 8% as fungicides. Herbicides remained the most widely used pesticides in
the three market sectors: agriculture, industry/commercial/government, and home and garden.
Table 1.5 shows that in 1997, more insecticides were applied to control insects in cotton and corn
than other crops. Insecticide use on potatoes, other vegetables, apples, and citrus remained roughly
constant between 1980 and 1997 (National Research Council, 2000). From Table 1.6, it is seen that
in 1998, we heavily used organophosphorus insecticides for controlling termites, livestock pests, and
mosquitoes. Organophosphorus insecticides have been one of the most important classes of insecticides
used for protecting crops, livestock, and human health over the past 60 years. In the United States,
Table 1.3 World and U.S. Amount of Pesticide Active Ingredient Used in 2007
World Market U.S. Market
Million Million U.S. Percentage
Pesticide Type Pounds % Pounds % of World Market
Herbicidesa 2096 40 531 47 25
Insecticides 892 17 93 8 10
Fungicides 518 10 70 6 14
Othersb 1705 33 439 39 26
Total 5211 100 1133 100 22
Source: From Grube, A. et al., Pesticide Industry Sales and Usage. 2006 and 2007 Market
Estimates, Biological and Economic Analysis Division, Office of Pesticide Programs,
Office of Chemical Safety and Pollution Prevention, U.S. Environmental Protection
Agency, Washington, DC, 2011. http://www.epa.gov/opp00001/pestsales.
a Includes plant growth regulators.
b Includes nematicides, fumigants, and other miscellaneous conventional pesticides, and other

chemicals used as pesticides such as sulfur, petroleum oil, and sulfuric acid.
Need for Pesticides and Their Pattern of Use 5

Table 1.4 Volume of Conventional U.S. Pesticide Active Ingredient Used by Class and Sector in 2007
Million Pounds
Sector Herbicidesa Insecticidesb Fungicides Nematicidesc Otherd Total
Agriculture 442 65 44 108 25 684
Industry/commercial/government 46 14 19 24 4 107
Home and garden 43 14 7 1 1 66
Total 531 93 70 133 30 857
Source: From Grube, A. et al., Pesticide Industry Sales and Usage. 2006 and 2007 Market Estimates, Biological
and Economic Analysis Division, Office of Pesticide Programs, Office of Chemical Safety and Pollution
Prevention, U.S. Environmental Protection Agency, Washington, DC, 2011. http://www.epa.gov/opp00001/
pestsales.
a Includes plant growth regulators.
b Includes miticides.
c Includes fumigants.
d Includes rodenticides and other miscellaneous conventional pesticides.

Table 1.5 A
 creage and Amounts of Insecticides Applied to Major
U.S. Crops in 1997
Crop Acres (×1000) Pounds (×1000) Pounds per Acre
Cotton 13,808 19,300 1.398
Corn 80,277 17,500 0.218
Potatoes 1,362 3,300 2.423
Wheat 70,989 1,200 0.017
Soybeans 70,850 800 0.011
Other vegetables 3,526 5,300 1.503
Citrus 1,150 5,500 4.783
Apples 453 3,300 7.285
Source: Padgitt, M.D. et al., Production Practices for Major Crops in US
Agriculture, 1990–97, Statistical Bulletin No. 969, U.S. Department of
Agriculture, Economic Research Service, U.S. Printing Office,
Washington, DC, 2000.

Table 1.6  rganophosphorus Insecticide Usage in Nonagricultural

O
Sites in 1998 in the United States
Category Million Pounds
Termites 4
Livestock and pets 4
Mosquitoes 3
Residential and commercial indoor 3
Grain storage facilities 2
Turf and ornamental 1
Source: EPA, Staff Background Paper 5.1, Summary of Organophosphate
Pesticide Usage, TRAC, May 27, 98. http://epa.gov/oppfead1/trac/
sumry5-1.htm.

the top 10 organophosphorus insecticides used in 2007 were chlorpyrifos, malathion, acephate, naled,
dicrotophos, phosmet, phorate, diazinon, dimethoate, and azinphos-methyl (Grube et al., 2011).
However, as shown in Table 1.7, their use has declined gradually since 1980, 55% from 1997 to 2007,
and 61% from 1990 to 2007. In terms of world market value, between 1997 and 2010, there was a
marked decrease in organophosphates, methylcarbamates, and pyrethroids accompanied by a marked
increase in neonicotinoids and nonneuroactive insecticides (Figure 1.1) (Casida and Durkin, 2013).
6 THE Toxicology and Biochemistry of Insecticides

Table 1.7  mount of Organophosphorus Insecticide Active Ingredients Used

A
in the United States in All Market Sectors, 1990–2007 Estimates
All Insecticides Organophosphorus Insecticides
Year Million Pounds Million Pounds % of All Insecticides
1980 228 131 57
1985 161 114 71
1990 121 85 70
1991 114 82 72
1992 116 84 72
1993 115 79 69
1994 124 83 67
1995 125 80 64
1996 116 75 65
1997 112 73 65
1998 103 66 64
1999 126 91 72
2000 122 88 72
2001 105 73 70
2002 130 59 45
2003 115 46 40
2004 114 46 40
2005 104 40 39
2006 99 37 38
2007 93 33 35
Source: From Grube, A. et al., Pesticide Industry Sales and Usage. 2006 and 2007
Market Estimates, Biological and Economic Analysis Division, Office of
Pesticide Programs, Office of Chemical Safety and Pollution Prevention, U.S.
Environmental Protection Agency, Washington, DC, 2011. http://www.epa.gov/
opp00001/pestsales.

40
OP MC Neonic Pyr Other

30
Worldwide market (%)

20

10

0
Years (1997–2010)

Figure 1.1 Changes in the use of insecticides between 1997 and 2010 for organophosphates (OPs), meth-
ylcarbamates (MCs), neonicotinoids (Neonic), pyrethroids (Pyr), and other compounds. In each
class, the six bars represent data (from left to right) for 1997, 2000, 2002, 2005, 2008, and 2010.
(Adapted from Casida, J.E. and Durkin, K.A., Annu. Rev. Entomol., 58, 99, 2013.)
Need for Pesticides and Their Pattern of Use 7

1.4 PESTICIDE ECONOMICS

Table 1.8 shows that in the United States, pesticide expenditures were about $12.5 billion, which
accounted for 32% of the approximately $40 billion world market in 2007 (Grube et al., 2011).
As shown in Figure 1.2, the four chemical classes of insecticides of major importance (organophos-
phates, carbamates, synthetic pyrethroids, and neonicotinoids) account for about 62% of the current
global insecticide sales. Insect growth regulators such as juvenoids, ecdysone agonists (diacylhy-
drazines), and acylureas account for about 5% of the global market. The spinosyns, diamides, and
sodium channel blockers (indoxacarb, metaflumizone) account for about 12% of the total market.
Pesticides have become increasingly expensive to develop. The present cost of discovery and
development averages about $250 million per pesticide. On the average, a company must synthesize
and screen 140,000 compounds for each one registered and sold commercially. Nowadays, the time
period from discovery to initial sales ranges from 8 to 12 years (Sparks, 2013). Increased time and
costs have had a significant impact on the rate of introduction of new pesticides and on their unit
costs once they have been developed. One important reason for the slowdown in the development of
new pesticides is that increasing restrictive legislation by the Congress and corresponding regula-
tion by the EPA have increased both the costs and the time required for the process.

Table 1.8 World and U.S. Pesticide Expenditures at User Level by Pesticide Type, 2007 Estimates
World Market U.S. Market
Pesticide Type Millions ($) % Millions ($) % U.S. Percentage of World Market
Herbicides a 15,512 39 5,856 47 38
Insecticides 11,158 28 4,337 35 39
Fungicides 9,216 23 1,375 11 15
Othersb 3,557 9 886 7 25
Total 39,443 100 12,454 100 32
Source: From Grube, A. et al., Pesticide Industry Sales and Usage. 2006 and 2007 Market Estimates, Biological
and Economic Analysis Division, Office of Pesticide Programs, Office of Chemical Safety and Pollution
Prevention, U.S. Environmental Protection Agency, Washington, DC, 2011. http://www.epa.gov/opp00001/
pestsales.
a Includes plant growth regulators.
b Includes nematicides, fumigants, and other miscellaneous conventional pesticides, plus chemicals used as

pesticides (e.g., sulfur and petroleum oil).

Spinosyns—3% Diamides—7% Na channel blockers—2%

Acaricides—4%
Avermectins—6%
Misc.—6%
Fiproles—5%

IGRs—5% Organophosphates—13%

Carbamates—6%

Neonicotinoids—26%

Pyrethroids—17%

Figure 1.2 (See color insert.) Different chemical classes of insecticides and their global market share.
(Adapted from Sparks, T.C., Pestic. Biochem. Physiol., 107, 8, 2013.)
8 THE Toxicology and Biochemistry of Insecticides

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10, 2010.
Sparks, T.C., Insecticide discovery: An evaluation and analysis, Pestic. Biochem. Physiol. 107, 8, 2013.
Terriere, L.C., The Biochemistry and Toxicology of Insecticides, Oregon State University, Corvallis, OR, 1982.
Von Rumker, R., Kelso, G.K., Horay, F., and Lawrence, K.A., A study of the efficiency of the use of pesticides
in agriculture, EPA 540/9-75-025, U.S. Environmental Protection Agency, Washington, DC, 1975.
Ware, G.W. and Whitacre, D.M., The Pesticide Book, 6th ed., MeisterPro Information Resources, Willoughby,
OH, 2004.
Yu, S.J. and Huang, S.W., Purification and characterization of glutathione S-transferases from the German
cockroach, Blattella germanica (L.), Pestic. Biochem. Physiol. 67, 36, 2000.
 Chapter 2

Formulation of Pesticides

2.1 INTRODUCTION

With the exception of a few pesticides such as fumigants, pesticides are seldom used in their pure
form. The technical-grade chemicals need to first be formulated as mixtures prior to application.
Several thousand pesticides are registered for use by the Environmental Protection Agency (EPA)
and sold in interstate commerce. Therefore, it is important to understand the principles involved in
formulation since these influence the use and behavior of pesticides.
Pesticides are formulated by mixing active ingredients (AIs) with inert ingredients to make a
combination that is effective and safe to use. In formulating a pesticide, important factors that need
to be considered include the chemical and physical properties of the AI and the inert materials, the
type of application equipment, the nature of the target surfaces, and the marketing and transport
aspects of pesticide usage. We must know the properties of the toxicant, including melting point or
boiling point, rate of hydrolysis, specific gravity, solubility, vapor pressure, ultraviolet degradation,
and its inherent biological activity. We must also know the inert ingredient regarding its compat-
ibility with AI, compatibility with container, and the physical properties of the ultimate mixture.
Finally, the formulation itself must be evaluated to learn the homogeneity of the mixture, particle
size, storage stability, retention by the target, wetting, penetration and translocation in plants, resid-
ual nature on a target or in the soil, nature of deposit, efficacy, and hazard to user (Terriere, 1982).
The following references are useful for understanding pesticide formulations: Ware and Whitacre
(2004), Anderson (1977), Hassall (1990), and Foy and Pritchard (1996).

2.2 TYPES OF FORMULATION

The following 12 formulations are commonly used in agriculture, in the home and garden, as
well as those employed in structure and commercial pest control.

2.2.1 Dusts

Dusts usually contain two ingredients, an inert diluent and a toxicant. The latter accounts for
only 1%–10% of the mixture. For this reason, dusts are more costly per pound of toxicant due to
shipping costs. The inert ingredients of dusts must be relatively nonadsorptive to avoid inactivating
the pesticides, for example, talc, pyrophyllite, or clay. They must be finely ground for ease of appli-
cation and good coverage. Dusts have been the simplest formulations of pesticides to manufacture
and easiest to apply. However, dusts are least effective and the least economical of the pesticide
formulations because dusts tend to drift during application, resulting in a poor deposit to target
surfaces. For instance, an aerial application of a standard dust formulation of pesticide will result in

9
10 The Toxicology and Biochemistry of Insecticides

10%–40% of the chemical reaching the crop (Ware and Whitacre, 2004). Another disadvantage is
their inhalation hazard. From the standpoint of dermal toxicity to the user, however, dusts are usu-
ally safer than liquid formulation. A mixed blessing is the shorter residual life of pesticides applied
as dusts compared to those as suspensions or emulsions.
Dusts are also formulated as dust concentrates to reduce shipping costs. These concentrates may
contain 25%, 50%, or even 90% toxicant. They can be diluted with cheap local diluents by a simple
process of mixing or blending prior to application. Currently, dusts are not much used, because
of their drift potential and inhalation hazard and because of improvements in the other types of
formulations.

2.2.2 Wettable Powders

A wettable powder (WP) is the most widely used agricultural formulation. It consists of a
t­oxicant, inert diluents, and a wetting agent. The inert diluent is usually an adsorptive clay such as
attapulgite. The wetting agent may be a blend of two or more surfactants. The toxicant usually com-
prises from 25% to 75% of the mixture. WPs are first prepared by spraying the toxicant (if liquid)
onto the clay at a reasonable temperature. Another method is to mix the clay with a solution contain-
ing the toxicant (if solid) and then allowing the solvent to evaporate. WPs are sometimes prepared
by the direct grinding of a crystalline toxicant along with a diluent. The objective in any case is to
prepare a homogeneous mixture that can be ground to a fine powder.
As the name implies, WPs are designed to be mixed with water and applied as a spray. These are
relatively safe on foliage (no phytotoxicity), but the spray mix requires constant mixing.

2.2.3 Emulsifiable Concentrates

This type of formulation is also designed to be applied as a spray by mixing with water to form an
emulsion. The opaque emulsions are relatively stable requiring a minimum of agitation. An emulsifi-
able concentrate (EC) consists of a toxicant, a solvent for the toxicant, and an emulsifier (surfactant).
Both solvent and surfactant may be a mixture of two or more substances. The toxicant content of ECs
is expressed in terms of weight/volume rather than as weight/weight as with the WP. Thus, ECs may
contain 2–4 pounds of toxicant per gallon, approximately equivalent to 25%–50% by weight.
ECs are usually more easily absorbed by the skin than WPs and dusts and are thus more haz-
ardous if spilled on the applicator. Sensitive plants are more apt to be damaged by this formulation
than by WPs since the solvent may increase penetration into the plant. On the other hand, the lack
of masking by diluent probably increases the effectiveness of ECs over WPs (Terriere, 1982).

2.2.4 Suspendable Concentrates or Flowables

Some pesticides are so insoluble in the solvents used in ECs that they have to be formulated in
other ways. In this case, these pesticides can be formulated to become water-based mixtures that
can be handled and applied in the same manner as ECs. Basically, suspendable concentrate formula-
tions that contain 50%–90% of a toxicant are WPs of small particle size (1–5 μm) that they remain
in suspension for long periods. Suspendability and storage stability are improved by the inclusion of
surfactants and various additives. Oils can be added when penetration of plants is desired.

2.2.5 Water-Soluble Powders

As the name implies, this group of insecticides used in water-soluble formulations easily dis-
solves in water. In this formulation, the technical-grade material is a finely ground solid. It can be
added to the spray tank, where it dissolves quickly. Once dissolved, a soluble powder becomes an
Formulation of Pesticides 11

invisible solution that can be applied to approved surfaces without constant agitation. An example
of such formulation is Orthene® PCO Pellets.

2.2.6 Solutions

A solution formulation is the true solution containing a toxicant and solvent, which can be
used directly without further dilution. Solutions can be used for household insect sprays, roadside
weed eradication, and rangeland spraying, whenever phytotoxicity is not a problem. In these cases,
the toxicant can be dissolved in a low-cost solvent such as kerosene or fuel oil. Solutions do not
contain surfactants because the solvent wets the target readily.
Some pesticides are sufficiently soluble in water to permit their formulation in water. However,
this may not be done unless hydrolytic stability and toxicity hazard are favorable. Instead, such
compounds are dissolved in a water-miscible solvent to avoid hydrolysis and then mixed with water
prior to application.

2.2.7 Granules

A granular formulation is basically the same as a dust formulation. It contains a toxicant

(1%–10%) and an inert diluent. The major difference is in the particle size; granules range from
20 to 100 mesh, while dusts pass through 300 mesh screens.
Granular particles can be prepared in several ways. The toxicant may be added so as to impreg-
nate the granule and thus be completely released only when the granule breaks up. It may be
surface coated on the granule using a volatile solvent, which evaporates from the formulation.
The inert diluents can be clays or organic materials such as corncobs, pecan shells, tobacco stems,
and walnut shells.
Granules are mostly used for application to soil and water. They are useful in a variety of insect
control situations. Examples include application to the seedbed for seed protection, broadcasting
and tilling into the soil for soil insect control, application to growing crops for either foliar or soil
insect control, and application to ponds for mosquito control. They are easy to apply and are not as
likely to drift as dusts or spray. They have less tendency to adhere to foliage and can thus be applied
to soil surface through a canopy of leaves. Researchers often find that when different formulations
of a toxicant are compared, the granules perform better.

2.2.8 Water-Dispersible Granules

A water-dispersible granule (WG) formulation contains typically a toxicant (50%–95%, w/w),

dispersant, binder, and diluent. This formulation, also known as dry flowable, is intended for appli-
cation after disintegration and dispersion in water by conventional spraying equipment. WGs are
easier to use than WPs because they have low dust properties (due to larger particles) and exhibit
good flowability.

2.2.9 Ultralow-Volume Formulations

Ultralow-volume (ULV) formulations are usually the undiluted technical-grade material or, in
the case of solid, the original product dissolved in a minimum of solvent. They are applied without
further dilution in an extremely fine spray generated by special aerial or ground spray equipment.
ULV formulations are useful for the control of public health, agricultural, and forest pests. ULV
applications offer several advantages. The low volumes used—0.5 pt to 0.5 gal/acre, as compared
with 3–10 gal/acre for normal spray—allow for either the use of simplified, light weight equipment
or the very efficient use of equipment. This technique is useful in treating large areas. For example,
12 The Toxicology and Biochemistry of Insecticides

an airplane carrying 100 gal of ULV malathion could spray 400–800 acres of rangeland before
reloading. In orchard spraying, the spray tank may be as small as 5 gal instead of the commonly
used 500 gal tank. Another advantage of ULV is the greater effectiveness of the toxicant, possibly
because there are no inert ingredients or surfactants to mask the toxicant. This can result in reduced
rate of application (Terriere, 1982).

2.2.10 Aerosols

Aerosols are commonly used for controlling resident flying and crawling insects such as mos-
quitoes and cockroaches. In principle, the AI is dissolved in a volatile petroleum solvent, and the
resulting solution is atomized through a jet by means of a propellant. The propellant can be a gas
under pressure or a liquid that is gaseous at atmospheric pressure. Chlorofluorocarbon used to be
employed as a propellant, but has been replaced for environmental reasons with other volatile liquids,
such as butane and dimethyl ether or by nonflammable compressed carbon dioxide or nitrogen
(Ware and Whitacre, 2004).

2.2.11 Controlled-Release Formulations

Controlled-release (CR) formulations are a recent innovation in which the pesticide is incor-
porated into a carrier, generally a polymeric material (Scher, 1999). The rate of release of the pes-
ticide is determined by the properties of the polymer itself as well as environmental factors. There
are mainly two types of CR formulations: reservoir devices and monolithic devices. As shown in
Figure 2.1, in the reservoir device, the toxicant is enclosed in capsules of thin polymeric mate-
rial to become microcapsules (1–100 μm in diameter). In the monolithic device, the toxicant is
uniformly dissolved or dispersed within the polymer matrix to become microparticles (1–100 μm
in diameter) or strips. An example of this device is Hot Shot® No-Pest Strip in which dichlorvos
is the AI. This type of formulations is used widely in pet flea and tick collars in which tetra-
chlorvinphos, tetrachlorvinphos/S-methoprene, propoxur, propoxur/S-methoprene, etc., are used
as AIs currently.
Microcapsules are made by a two-step process mixing two chemical systems, the pesticide in
a solvent and the capsule material, so that a wall forms around pesticide droplets (Figure 2.2). The
size of the capsule can be controlled by mixing speed, by the chemical used, and by the conditions.
The capsule material used will determine the nature of the wall, such as porosity and decomposition
(Terriere, 1982).

Polymer
matrix

Agent

Agent

Membrane

Reservoir device Monolithic device

Figure 2.1 Reservoir and monolithic diffusion-controlled devices. (From Lewis, D.H. and Cowsar, D.R., Principles
of controlled release pesticides, in: Scher, H.B. ed., Controlled Release Pesticides, ACS Symposium
Series 53, American Chemical Society, Washington, DC, 1977, p. 1. With permission.)
Formulation of Pesticides 13

Figure 2.2 Electron micrograph of microcapsules on filter paper (1000×). (From Morgan, R.L. et al., Use of
selected surfactants to reduce dermal toxicity of insecticides, in: Cross, B. and Scher, H.B. eds.,
Pesticide Formulations: Innovations and Developments, ACS Symposium Series 371, American
Chemical Society, Washington, DC, 1988, p. 131. With permission.)

Three different mechanisms may be involved in controlling the release of biologically active
compounds: (1) release through a membrane by diffusion; (2) removal of a protective wall by an
enzyme, microorganisms, or chemical attack; and (3) release from chemical or physical bonds by
temperature or moisture as shown in the following figure:

Synthesis
— — — — — — — — — ->
Polymer + pesticide Polymeric pesticide
<— — — — — — — — — -
Environment

These formulations can reduce worker exposure by decreasing pesticide toxicity and can minimize
pesticide impact on the environment by reducing evaporation and leaching. Moreover, less insec-
ticide is needed to achieve biological efficacy because of the reduction in environmental losses
such as ultraviolet and soil degradation. There are also disadvantages, however, including expensive
technology, longer lasting residues, and toxicity to bees (the microcapsules are approximately the
same size as many pollen grains).

2.2.12 Baits

Baits can be very useful for achieving selective toxicity of insecticides against some species
of insects. Spot application, that is, the placing of the bait in selected places accessible only to the
target species, permits the use of insecticides in a safe manner with no environmental disruption.
Several bait formulations are currently available on the market. For example, Amdro® Fire Ant Bait
14 The Toxicology and Biochemistry of Insecticides

(containing hydramethylnon as toxicant) is an effective way to eliminate fire ants. Combat® Source
Kill containing hydramethylnon or fipronil as toxicant controls cockroaches. Combat® Roach Killing
Bait Strips contain fipronil as toxicant. Advion® Fire Ant Bait contains indoxacarb as toxicant. Harris
Famous Roach Tablets, which contain boric acid as toxicant, are used for cockroach control. Raid®
Ant Baits contain avermectin B1 as toxicant. Hot Shot® Liquid Ant Bait contains dinotefuran as
toxicant. In addition, a bait containing hexaflumuron or noviflumuron as toxicant is used in the
Sentricon® Termite Elimination System and diflubenzuron as toxicant in the XTerra® Termite Bait
System. Bait gels are common for household insect control. Examples are Maxforce Roach Bait
Gel, which contains hydramethylnon or fipronil as toxicant, and Maxforce FC Professional Insect
Control™ Ant Killer Bait Gel, which contains fipronil as toxicant. Advion® Cockroach Gel Bait con-
tains indoxacarb as toxicant. GF-120 NF Naturalyte® Fruit Fly Bait is an insecticide bait for control
of tropical fruit flies (Tephritidae). It contains a mixture of the insecticide spinosad, a microbially
hydrolyzed protein, sugars, adjuvants, and a series of conditioners (Mangan et al., 2006).
A bait formulation consists of a carrier, toxicant, and feeding stimulants (phagostimulants).
Carriers include laying mash, cracked corn, wheat bran, corncob grits, peanut hulls, and cottonseed
meal. Feeding stimulants include crude cottonseed oil, refined soybean oil, sucrose, coax, brewer’s
concentrate (brewery by-product), malt extract, glucose, maltose, honey, and wheat germ oil.
A malathion 4% bait formulated from crude cottonseed oil (5%) and sucrose (10%) on a laying
mash carrier was very effective in controlling mole crickets in the field (Kepner and Yu, 1987).
A microencapsulated bait called Slam®, which consists of cucurbitacins and 8% carbaryl, is also
available for controlling corn rootworm adults. Cucurbitacins that are found in all cucurbits are
feeding stimulants for corn rootworms.
It is important to know the concentration of insecticide on the label. For dry formulations such
as WPs, dusts, and granules, the insecticide concentration is expressed in the percentage of AI in the
formulation. For example, Diazinon® 50W means that 50% of diazinon is in the WP formulation. On
the other hand, for liquid formulations such as solutions and ECs, the concentration of i­nsecticide
is expressed in pounds of AI/gal of the formulation. For example, Diazinon® 4E means that 4 lb of
diazinon is in each gallon of the formulation.

2.3 NONPESTICIDAL INGREDIENTS OF FORMULATIONS

2.3.1 Solvents

Solvents are important ingredients of ECs and of solution formulations. When the formulation
is to be used on crops, it is critical that a solvent be nonphytotoxic. The solvent must have a high
level of solvent power if an EC is being formulated. Because most toxicants are insoluble in water,
the solvent must also be water insoluble. Otherwise, when the EC is added to water in the spray
tank, the solvent will mix with the water and leave the toxicant behind as a crystalline precipitate.
The carrying power of the solvent, that is, the amount of pesticide it will hold in solution, is impor-
tant in the storage stability of formulations. If near its saturation point at ordinary temperatures, it
may exceed this at low temperatures with the result that solvent and pesticide may separate, causing
crystal formation and phase separation (Terriere, 1982).
Heavy solvents (high specific gravity) are undesirable in most cases because it is hard to stabi-
lize the emulsion when the EC is mixed with water. If the specific gravity of the solvent is near that
of water, the setting tendency of the emulsion is decreased. The terms top creaming and bottom
creaming are used to describe emulsions in which the insecticide-containing solvent has risen to
the top or settled to the bottom of the emulsion. Other considerations in the choice of solvents for
pesticide formulations include flammability, purity, odor, color, skin irritability (in animal dips and
sprays), and cost (Terriere, 1982).
Formulation of Pesticides 15

2.3.2 Diluents

Diluents, sometimes known as inerts or carriers, play an important role in the behavior of the
formulated product. Diluents have been prepared from agricultural wastes such as walnut shells,
pecan shells, tobacco stems, and corncobs; from minerals such as kaolinite, attapulgite, and talc;
and from fossilized deposits such as diatom beds. The exact diluent used in a given preparation
depends on cost, properties, and availability. Dusts require low sorptive inerts to minimize the
toxicant–diluent interaction. For WPs, inerts must be high in sorptive power because they carry a
large amount of toxicant especially when the toxicant is a liquid. Otherwise, the formulated product
would be likely to cake badly in storage. It is required that a diluent must be truly inert. However,
formulators often find that an inert diluent contains hot spots or alkalinity to inactivate part of the
toxicant. In this case, urea can be used as a deactivator to counteract the undesirable effects in some
dust and wettable formulations (Terriere, 1982).

2.3.3 Surfactants

Surfactants, also known as surface-active agents, are chemicals that will orient at an interface.
They serve as coupling agents, joining two phases, liquid–liquid, liquid–solid, or liquid–air. When
the phases being coupled are liquid–air, the surfactant may cause foaming and will be called a
foaming agent. If the interfaces are liquid–solid, the surfactant may result in the wetting of the solid
and will be called a wetting agent. In liquid–liquid interfaces, such as oils and water, the surfactant
would be an emulsifier (emulsifying agent) because it allows oils and water to mix as an emulsion.
There are more than 3000 commercial surfactants. They are grouped according to the type of action
as follows: wetting agents, stabilizing agents (emulsifiers, dispersants), spreaders, penetrants, cosol-
vents (coupling agents), hygroscopic agents, or stickers (deposit builders) (Terriere, 1982).
Surfactants are divided into three main groups, based on their ionization in water; these are
anionic surfactants, cationic surfactants, and nonionic surfactants. If on ionization one end of the
molecule becomes a negative ion, the surfactant is known as an anionic surfactant as shown in
Figure 2.3.

Sodium laurate
O

ONa

In water
O

O– + Na+

Nonpolar tail Polar head

(carboxyl group)

Tail Head

Figure 2.3 Ionization of sodium laurate in water.

16 The Toxicology and Biochemistry of Insecticides

Conversely, when a positive ion is formed, it is called a cationic surfactant. The following exam-
ples illustrate the structure and the ionization of surfactants:

1. Anionic surfactants:
Sodium lauryl sulfate [CH3(CH2)11OSO2O − + Na+]
2. Cationic surfactants (quaternary ammonium compounds):
Lauryl trimethylammonium chloride [CH3(CH2)11 N(CH3 )3+ + Cl−]
3. Nonionic surfactants (polyethylene oxide derivatives):
Triton X-100 [4-(C8H17)C6H4(OCH2CH2)nOH] (n = 9–10)

It can be seen that in each of the three types of surfactants, there is a chemical grouping that would
be considered nonpolar in nature. This is usually a long-chain fatty acid (saturated hydrocarbon).
The polar end of the molecule may be the sodium salt of an acid, the chloride salt of a quaternary
nitrogen, or the free hydroxy group of a glycol ether.
As mentioned in the preceding text, when an anionic surfactant dissolves in water, it will ionize
and disperse readily in water to form a micelle in which the negatively charged carboxylate groups
orient in the water phase and form hydrogen bonds with water molecules, and the nonpolar insol-
uble hydrocarbon chains, which do not hydrogen-bond with water, are hidden within (Figure 2.4).
On adding oil drops (from ECs) or solid particles (from WPs) in water, these particles will go to the
center of micelles (Figures 2.5 and 2.6). Anionic surfactant micelles have a net negative charge and
Forms hydrogen bond
with water molecule
–
H+
Na+
O–

H+
Na+ Mutual electrostatic
repulsion

Na+
Attractive forces
Na+ (van der Waals interactions)
Na+

Figure 2.4 Sodium laurate micelle.

Oil droplet

Emulsion

Figure 2.5 A micelle with an oil drop.

Formulation of Pesticides 17

Solid particle

Suspension

Figure 2.6 A micelle with a solid particle.

remain suspended because of mutual electrostatic repulsion. Cationic surfactants act in a similar
manner as anionic surfactants except that the suspended particles are surrounded by a sphere of
positive charges. In the case of nonionic surfactants, hydrophilic groups orient in the water phase
and lipophilic groups orient in the oil or solid phase.
Ionic surfactants may cause complications with water during application. For example, in hard
water, there is an excess of Ca2+, Mg2+, Fe2+, SO 4 −−, and other inorganic ions. These will react with
the anionic or cationic ions of the surfactant to form insoluble salts, which precipitate, removing
the surfactant from the spray solution. This will result in reducing the surface-active properties
of the surfactant. For this reason, pesticide formulators often use both ionic and nonionic surfac-
tants in their formulations. Because the latter agents do not ionize, they are not as likely to react with
the constituents of hard water.
As we know, the surface tension of water is high. When droplets of water fall on waxy surfaces,
they tend to form small spheres. If a surfactant is added to water, surfactant molecules will displace
some water molecules from the surface, which lower the surface tension (Figure 2.7). As a result,
the droplets can spread over the waxy surface and lose their spherical shape. Therefore, in addition
to acting as surface-active agents in spray solutions, surfactants also lower the surface tension of
water, thus increasing the area of contact.
Work is underway to use nanotechnology to develop new pesticide formulations called nanopes-
ticides (e.g., nano emulsions and nanocapsules), which will increase the efficacy and reduce the
environmental impact of pesticides (Kah and Hofmann, 2014).

2.4 DISPOSAL OF PESTICIDE CONTAINERS

Pesticides are toxic chemicals. Improper disposal of pesticides or their containers leads to envi-
ronmental contamination and may face both civil and criminal penalties. The following procedures
are appropriate for disposing of pesticide containers (Nesheim and Fishel, 2011).
Empty drums, bottles, or cans must be triple-rinsed before disposing of them as follows:

1. Empty all pesticide into the spray tank.

2. Fill the container about one-fourth full with water and rinse thoroughly.
3. Add the rinsate from the container to spray tank and drain the container in a vertical position for 30 s.
4. Repeat rinsing two more times.
(Triple rinsing also can be replaced with pressure rinsing. This is done using a special pressure rinsing
device that is inserted into the container for rinsing the inside of the container.)
18 The Toxicology and Biochemistry of Insecticides

Point contact of droplet with surface

H2O

Water molecules ( ), close packed; Waxy surface

forces of cohesion high

(a)

Surfactant molecules
Large area
of contact

Surfactant molecules ( ), displace some H2O

water molecules from surface; forces of
adhesion low Waxy surface

The area of contact increases when

lower forces of adhesion replace the
(b) high forces of cohesion

Figure 2.7 Effect of surfactant on surface tension. (a) Because of high forces of cohesion, there is little contact
between droplet and surface in the absence of surfactants. (b) The area of contact increases when
lower forces of adhesion replace the high forces of cohesion. (From Hassall, K.A., The Biochemistry
and Uses of Pesticides, 2nd edn, VCH Publishers, Inc., New York, 1990, p. 55. With permission.)

5. Puncture the top and bottom of the container to prevent its reuse.
6. Dispose of the empty container in a sanitary landfill.
Empty bags (dry formulations) should be shaken clean, opened both ends of the container to prevent
its reuse, and then disposed of in a sanitary landfill.

2.5 PESTICIDE APPLICATION EQUIPMENT

Many types of equipment are available for applying pesticides. These include hand-operated
sprayers, motorized sprayers, boomless sprayers, boom sprayers, airblast sprayers, granular applica-
tors, and aerial applicators (fixed-wing aircraft or helicopters). Good results can be obtained when
suitable equipment is selected for application. When selecting equipment, one needs to consider
several factors including the size and type of area to be treated, the type of pest, the pesticide for-
mulation, the required application accuracy, and cost of the equipment. Because of the scope of this
book, readers interested in pesticide application equipment are referred to the following ­publications:
Matthews (2000) and the website http://www.agf.gov.bc.ca/pesticides/f_2.htm.

REFERENCES

Anderson, W.P., Weed Science: Principles, West Publishing Co., St. Paul, MN, 1977, Chap. 7.
Foy, C.L. and Pritchard, D.W., Pesticide Formulation and Adjuvant Technology, Foy, C.L. and Pritchard, D.W.,
Eds., CRC Press, Boca Raton, FL, 1996.
Hassall, K.A., The Biochemistry and Uses of Pesticides, 2nd ed., VCH Publishers, New York, 1990.
Kah, M. and Hofmann, T., Nanopesticide research: Current trends and future priorities, Environ Int. 63, 224, 2014.
Formulation of Pesticides 19

Kepner, R.L. and Yu, S.J., Development of a toxic bait for control of mole crickets (Orthoptera: Gryllotalpidae),
J. Econ. Entomol. 80, 659, 1987.
Lewis, D.H. and Cowsar, D.R., Principles of controlled release pesticides, in Controlled Release Pesticides,
Scher, H.B. Ed., ACS Symposium Series 53, American Chemical Society, Washington, DC, 1977, p. 1.
Mangan, R.L., Moreno, D.S., and Thompson G.D., Bait dilution, spinosad concentration, and efficacy of
GF-120 based fruit fly sprays, Crop Protect. 25, 125, 2006.
Matthews, G.A., Pesticide Application Methods, 3rd edn., Blackwell Science, Inc., Oxford, U.K., 2000.
Morgan, R.L., Rodson, M., and Scher, H.R., Use of selected surfactants to reduce dermal toxicity of insecti-
cides, in Pesticide Formulations: Innovations and Developments, Cross, B. and Scher, H.B., Eds., ACS
Symposium Series 371, American Chemical Society, Washington, DC, 1988, p. 131.
Nesheim, O.N. and Fishel, F.M., Proper disposal of pesticide waste, University of Florida IFAS Extension,
Publication #P1-18, 2011.
Scher, H.B., Controlled Release Delivery System for Pesticides, Scher, H.B. Ed., Marcel Dekker, New York,
1999.
Terriere, L.C., The Biochemistry and Toxicology of Insecticides, Oregon State University, Corvallis, OR, 1982.
Ware, G.W. and Whitacre, D.W., The Pesticide Book, 6th edn., MeisterPro Information Resources, Willoughby,
OH, 2004.
 Chapter 3

Pesticide Laws and Regulations

3.1 INTRODUCTION

The use and sale of pesticides is strictly regulated by both federal and state laws to protect
p­ ublic health and the environment. No one can use pesticides without encountering these laws either
directly or indirectly, and all professional workers should be familiar with them. In this chapter, we
will summarize the major provisions of the current laws. There are three important federal pesticide
laws in the United States (Anonymous, 1997; Ware and Whitacre, 2004). Pesticides are regulated
by three federal agencies, namely, the Environmental Protection Agency (EPA), the Food and Drug
Administration (FDA), and the U.S. Department of Agriculture (USDA).
The first law was the Pure Food Law of 1906. It has been amended several times since then and
is now known as the Federal Food, Drug, and Cosmetic Act (FFDCA). Its main purpose is to main-
tain the purity of our food supply. This was the first federal effort toward protecting the consumer
from pesticide-contaminated foods, by providing tolerances for pesticide residues.
The Federal Insecticide Law was enacted in 1910. This law was replaced by a stronger law,
known as the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), in 1947. This law has
been amended several times since then. It deals with interstate commerce of pesticides, particularly
regarding the accuracy of the information on the label.
The third pesticide law is the Food Quality Protection Act (FQPA) of 1996. This law amends
the FIFRA and the FFDCA by providing a comprehensive and protective regulatory scheme for
pesticides.

3.2 FEDERAL INSECTICIDE, FUNGICIDE, AND RODENTICIDE ACT

FIFRA is the most important of the federal pesticide laws. Originally enacted in 1947, this
law was amended in 1972 to become the Federal Environmental Pesticide Control Act, commonly
referred to as FIFRA Amended. It has been amended several times since then, most recently in
1996. FIFRA is enforced by the EPA.

3.2.1 Registration of Pesticides

No person in any state may distribute or sell to any person any pesticide that is not registered
with the EPA. Each applicant seeking the registration must file a petition describing the product and
the research that has been done on it to prove its efficacy as a pesticide and to provide information
on its safety. A copy of the label, that is, the instruction to the user, must also be included in the
petition (see e.g., Figures 3.1 and 3.2).

21
22 The Toxicology and Biochemistry of Insecticides

Figure 3.1 EPA format for unclassified pesticide label. See Figure 3.2 for explanations. (From U.S. EPA
Label Review Manual, 2nd edn, 1996.)

The information provided must include all the facts known about the pesticide except, possibly,
the identity of inert ingredients in the formulation. These facts include the chemistry, biochemis-
try, and toxicology of the pesticide; data gathered in the evaluation of performance; data gathered
in the evaluation of safety with laboratory animals and certain wildlife species; behavior of the
pesticide in soil, air, and water; information on rates of use and the number of treatments; and
pest species controlled. The petition must also include information on pesticide residues in foods,
analytical methods for their detection, methods for their removal, and the requests for a tolerance
(Terriere, 1982; EPA, 2014).
A team of experts at EPA study the data provided and evaluate the claims made by the
­petitioner. They consider the requested uses (crops, livestock, and so forth) and the rates and
number of applications, the classification of the pesticide (restricted or general use), and the tol­
erance requested. Notice of the petition and of its consideration by the EPA is also published in the
Federal Register. Once the EPA experts are satisfied that the pesticide and intended uses comply
with the law, an approval is granted, and the product is registered. This registration is valid for
15 years unless unexpected, and adverse effects are detected in which case the EPA can revoke
the registration.
In order to minimize the exposure of bees and other pollinators from neonicotinoid insecti-
cides, in 2013, the EPA required label changes (Bradbury, 2013). Any products containing clothiani-
din, dinotefuran, imidacloprid, or thiamethoxam for outdoor foliar use regardless of formulation
Pesticide Laws and Regulations 23

8
Crop:
Precautionary Statements
8A
Hazards to Humans Restricted Use
(& Domestic Animals)
Danger Pesticide 9A

For Retail Sale to and Application Only By

Certified Applicators or Persons Under Their 9B
Direct Supervision Crop:
8B Environmental Hazards

Product Name 1

8C Physical or Chemical
Hazards
Active Ingredient %
Inert Ingredients % 6A
Directions for Use Total: 100.00%
It is a Violation of Federal Law to Use
Crop:
9C this Product in a Manner Inconsis- 7
tent with its Labeling. This Product Contains Lbs of Per Gallon 6B
Re-entry Statement
10A (If Applicable) Keep Out of Reach of Children 7A

Danger–Poison 7B Crop:
10B Category of Applicator
7C

Storage and Statement of Practical Treatment 7D

10C
Disposal If Swallowed Crop:
Storage If Inhaled
If on Skin
If in Eyes
Disposal
See Side Panel for Additional Precautionary Statements 7E

Mfg. by Warranty Statement

2
10D Crop: Town, State
5 Establishment No.
EPA Registration No. 4
Net Contents 3

Figure 3.2 EPA format for restricted use pesticide label. 1, Product name; 2, Company name; 3, Net
­contents; 4, EPA pesticide registration number; 5, EPA formulator manufacturer establishment
number; 6A, ingredients statement; 6B, pounds/gallon statement (if liquid); 7, Front-panel pre-
cautionary statements; 7A, Child hazard warning, “Keep Out of Reach of Children”; 7B, s­ ignal
word, Danger, Warning, or Caution; 7C, Skull and crossbones and word Poison in red; 7D,
Statements of practical treatment; 7E, Referral statement; 8, Side- or back-panel precautionary
statements; 8A, Hazards to humans and domestic animals; 8B, Environmental hazards; 8C,
Physical or chemical hazards; 9A, “Restricted Use Pesticide” block; 9B, Statement of pesticide
classification; 9C, Misuse statement; 10A, Reentry statement; 10B, Category of applicator; 10C,
“Storage and Disposal” block; 10D, Directions for use. (From U.S. EPA Label Review Manual,
2nd edn, 1996.)

or concentration must include a Pollinator Protection Box (Figure 3.3) on the label following the
Environmental Hazards section. The bee icon in the box must not be altered. In addition, new pol-
linator language must be added to the Directions for Use section of each label for three different
uses as described as follows:

1. For crops under contracted pollination services:

Do not apply this product while bees are foraging. Do not apply this product until flowering is com-
plete and all petals have fallen unless the following condition has been met:
• If an application must be made when managed bees are at the treatment site, the beekeeper
providing the pollination service must be notified no less than 48 h prior to the time of the
planned application so that the bees can be removed, covered, or otherwise protected prior
to spraying.
24 The Toxicology and Biochemistry of Insecticides

Figure 3.3 Pollinator Protection Box. (From Bradbury, S., Letter to registrants of nitroguanidine neonicotinoid
products, U.S. EPA Office of Chemical Safety and Pollution Prevention, Washington, DC, 2013.)
Pesticide Laws and Regulations 25

2. For food crops and commercially grown ornamentals not under contract for pollination services but
are attractive to pollinators:
Do not apply this product while bees are foraging. Do not apply this product until flowering is
­complete and all petals have fallen unless one of the following conditions is met:
• The application is made to the target site after sunset.
• The application is made to the target site when temperatures are below 55°F.
• The application is made in accordance with a government-initiated public health response.
• The application is made in accordance with an active state-administered apiary registry pro-
gram where beekeepers are notified no less than 48 h prior to the time of the planned application
so that the bees can be removed, covered, or otherwise protected prior to spraying.
• The application is made due to an imminent threat of significant crop loss, and a documented
determination consistent with an integrated pest management (IPM) plan or predetermined
economic threshold is met. Every effort should be made to notify beekeepers no less than 48 h
prior to the time of the planned application so that the bees can be removed, covered, or other-
wise protected prior to spraying.
3. Nonagricultural products:
Do not apply (insert name of product) while bees are foraging. Do not apply (insert name of product)
to plants that are flowering. Only apply after all flower petals have fallen off.

3.2.2 Classification of Pesticides and Certification of Applicators

Pesticides are classified under the terms of FIFRA as either general-use or restricted-use pesti-
cides. General-use pesticides can be used by the general public with low risk of harm to the user or
the environment as long as the applicator carefully follows the label directions. A pesticide will be
placed in the restricted-use category if it has unusual toxicity to man or other beneficial animals or if
it is known to cause unreasonable adverse effects on the environment. People who use restricted-use
pesticides must be certified as competent to do so. To be certified, pesticide applicators must pass
written examinations to show that they know how to use and handle pesticides. Under FIFRA, there
are two types of pesticide applicators, private and commercial, for using restricted-use pesticides.
A private applicator is a person who uses or supervises the use of any restricted-use pesticide for
purposes of producing any agricultural commodity on land owned or rented by him or his employer,
or on another person’s property if the work is done without compensation. Some examples are
farmers, ranchers, floriculturists, and orchardists.
A commercial applicator is a person who uses or supervises the use of restricted pesticides for
purposes other than a private applicator. Some examples are governmental workers, licensed pest
control personnel, agricultural pilots, power company employers, and highway department workers.

3.2.3 Other Provisions of FIFRA

3.2.3.1 Experimental Use Permits

New pesticides (not previously registered) can be tested in the field without registration under
experimental use permits. This is essential if we are to continue to develop new products.

3.2.3.2 Review and Suspension

As mentioned earlier, registrations are for 15 years. However, the administrator of the EPA can can-
cel a registration or change the classification of the pesticide if he or she becomes aware of new data or
other developments that would warrant such action. Because of the provisions, pesticide manufacturers
must provide the EPA with any new adverse information. The use of many pesticides, including such
insecticides as aldrin, chlordane, DDT, dieldrin, and heptachlor, has been cancelled or suspended.
26 The Toxicology and Biochemistry of Insecticides

3.2.3.3 Registration of Establishments

This permits the EPA to obtain information on production and sales of pesticides. Such informa-
tion must be kept confidential.

3.2.3.4 Unlawful Acts

It is unlawful for any person to deal with pesticides that are not registered or are adulterated,
misbranded, or sold in unlabeled packages. It is also unlawful to use any pesticide in a manner
inconsistent with its label.

3.2.3.5 Penalties

Civil penalties are as much as $5000 for registrants, commercial applicators, or dealers who
violate the act and a $1000 fine for private applicators who do so. Criminal penalties are as much as
$25,000 fine and 1 year in prison for registrants, commercial applicators, or dealers who violate the
act and a $1,000 fine and 30 days in prison for private applicators doing so.

3.2.3.6 Rights to Data

A registrant can use research data exclusively for 10 years unless another company agrees to pay
the registrant reasonable compensation for this use. This is intended to protect the inventors of new
pesticides and to promote innovation.

3.2.3.7 Special Review

Special review (formally called Rebuttable Presumption Against Registration) refers to the pro-
cess established by the EPA for public participation in disputes over risks and benefits of pesticides
before the formal cancellation is made. The EPA can challenge the continued registration of a
­pesticide if the pesticide may have unreasonable adverse effects to humans or the environment.
Once a decision has been made to place the suspected pesticide on the special review list, it is the
responsibility of the pesticide manufacturer or an agricultural group to counter the adverse evidence.
This might be done by proving that such evidence was in error or showing that in the continued use
of the pesticide, the benefits outweigh the risks that have been indicated by the adverse evidence.

3.2.4 Pesticide Categories

Regulations for the enforcement of FIFRA include a classification of pesticides according to their
toxicity. This is necessary because of the requirement that pesticides that are highly toxic to humans must
display a special warning. Thus, pesticides are divided into four categories based on the LD50 to rats, as
shown in Table 3.1. Some examples of labels showing these statements are seen in Figures 3.1 and 3.2.
Table 3.1 Pesticide Categories and Their Label Markings
Category of Toxicity Oral LD50 (mg/kg) Label Markingsa
I (Highly toxic) ≤50 “DANGER POISON”; skull and crossbones;
“Keep out of reach of children”
II (Moderately toxic) >50–500 “Warning”; “Keep out of reach of children”
III (Slightly toxic) >500–5000 “Caution”; “Keep out of reach of children”
IV (Relatively nontoxic) >5000 “Caution”; “Keep out of reach of children”
a The signal words “DANGER POISON” and the skull and crossbones symbol are all in red.
Pesticide Laws and Regulations 27

3.3 FEDERAL FOOD, DRUG, AND COSMETIC ACT

The FFDCA deals mainly with pesticide tolerance. Pesticide tolerances are set by the EPA and
enforced by the FDA or, in the case of meat, milk, poultry, and eggs, by USDA agencies.

3.3.1 Tolerance

A pesticide tolerance is the maximum amount of a pesticide residue that can be present on food. The
tolerance is expressed in ppm, or parts of the pesticide per million parts of food by weight. A chemical
generally regarded as safe need not be given a tolerance or the chemical may be exempted from the
requirement for a tolerance. This might occur, for example, when the chemical is used on nonbearing
fruit trees. For toxic chemicals, unified standards need to be set for raw and processed foods.

3.3.2 Basis for Tolerance

The process of setting a tolerance level on food first requires the determination of a no-­observable-
effect level (NOEL). A NOEL is the daily dosage of a pesticide that, when administered over a long
period of time, produces no observable symptoms or pathological effects in experimental animals.
A fraction of that dose, usually 1/100, is then set as an acceptable daily intake (ADI) for humans. An
ADI is expressed in mg pesticide (in the diet)/kg body weight/day. The reason for using a 100-fold
margin of safety is explained in the following text.
A major problem in establishing a tolerance is how to extrapolate from toxicity data for experi-
mental animals to the probable safety level of the pesticide in humans. This is handled by assuming
that humans are 10 times as sensitive to the pesticide as the rat and that their range to such substance
could vary by a factor of 10. Thus, a 100-fold margin of safety is introduced (10 × 10 = 100). This
means that the NOEL is divided by 100, and the resulting figure is used as the upper limit for the
amount allowed in human food. In the case of infants and children, a 1000-fold margin of safety is
used. Therefore, the tolerance on each food is set sufficiently low so that daily consumption of the
particular food will not exceed the ADI for the pesticide.

3.4 FOOD QUALITY PROTECTION ACT

The FQPA represents amendments to FIFRA as well as FFDCA. These amendments funda-
mentally change the way EPA regulates pesticides. The requirements included a new safety stan-
dard for assuring a reasonable certainty of no harm that must be applied to all pesticides used on
foods. Readers interested in the FQPA should check the website at http://www.epa.gov/pesticides/
regulating/laws/fqpa. This website provides background information on the provisions of FQPA and
discusses some of the specific issues raised by the FQPA, as well as the status of implementation of
this important new law. The following are some important changes (FQPA, 1996):

1. A unified safety standard for raw and processed foods: This amends the Delaney clause in the
FFDCA. Under the Delaney clause, a chemical that causes cancer in experimental animals (regard-
less of dose) shall not be allowed in processed food. Under the FQPA, pesticide residues shown to
cause cancer in humans or animals are allowed on food if the EPA determines that the tolerance is
safe, meaning that there is a reasonable certainty that no harm will result from exposure to the pes-
ticide. This amendment is necessary mainly because of improved analytical capabilities. Under the
Delaney clause, a carcinogen pesticide would be given a zero tolerance in processed food. However,
zero tolerance caused many problems. As the analytical sensitivity increased, concentrations that
were zero by old methods became measurable. A unified safety standard eliminates long-standing
problems posed by multiple standards for pesticides in raw and processed foods.
28 The Toxicology and Biochemistry of Insecticides

2. A 1000-fold safety factor for infants and children: As children grow rapidly, their brains and organs
are forming and they eat more for their size than do adults. Therefore, the addition of a 10-fold safety
factor is needed to assure the health of infants and children.
3. Reevaluation of tolerances: The EPA establishes a tolerance reassessment program and lays out a
schedule to reevaluate all tolerances that were in place as of August 1996, within 10 years.
4. The EPA must estimate aggregate exposures to pesticides from food, drinking water, and nonfood
(home, lawn, garden, etc.) uses when doing risk assessments.
5. The EPA must consider cumulative effects from other pesticides sharing a common mode of toxicity
when reassessing food use tolerances. It is possible for our food to contain more than one pesticide
with the same mode of action, for example, anticholinesterases. The regulations deal with this prob-
lem by first classifying pesticides according to their chemical grouping (when mode of action is not
known) or their mode of action if known. Provisions are made for decreasing the tolerances in those
cases where the food product contains two or more pesticides in the same grouping. Therefore, if
two pesticides, A and B, each with tolerances of 10 ppm are present in the same commodity, these
tolerances will be reduced to 5 ppm.
6. Screening chemicals for estrogenic (endocrine) effects: The endocrine system is composed of sev-
eral glands that are located in different areas of the body. These glands release hormones into
the bloodstream. The hormones travel to different locations in the body and act on specific target
organs. If the endocrine system is disrupted, those organs will not receive the correct amount of
hormones and might not function properly.
It has been suggested that certain pesticides at low levels in the environment disrupt the endo-
crine system. An environmental endocrine disruptor is defined as an exogenous agent that interferes
with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the
body that are responsible for the maintenance of homeostasis, reproduction, development, or behav-
ior (EPA, 1997). The FQPA requires that the EPA initiates the development of a screen process for
screening and testing pesticide chemicals for potential endocrine disruption.
7. The EPA must periodically review every pesticide registered every 15 years.
8. Conventional pesticides that possess at least one or more of the following characteristics are called
reduced risk pesticides: (a) low risk to human health, (b) low toxicity to nontarget organisms,
(c) low potential for groundwater contamination, and (d) compatibility with IPM practices. The fol-
lowing are reduced risk pesticides: acequinocyl, acetamiprid, bifenazate, buprofezin, chlorantranilip-
role, clofentezine, clothianidin, λ-cyhalothrin, diflubenzuron, dinotefuran, etofenprox, etoxazole,
fenpyroximate, flonicamid, hexaflumuron, indoxacarb, methoxyfenozide, milbemectin, novaluron,
noviflumuron, pyriproxyfen, pymetrozine, spinetoram, spinosad, spiromesifen, spirotetramat, tebufe-
nozide, thiamethoxam, and tolfenpyrad.

3.5 STATE LAWS

The three laws described previously apply only to interstate commerce. Regarding the situation
within a state where it would be possible for pesticides to be made and used, all of the states have
their own pesticide laws, usually modeled after the federal laws. Therefore, the coverage is complete
for all pesticides and all foods. However, individual state laws may vary. For example, the laws and
regulations in California are often more strict than the federal guidelines.
Under FIFRA, the states have been given responsibility for training and certification of pesti-
cide applicators. Moreover, under Section 24(c) of FIFRA, a state can register a pesticide for special
local needs, provided the intended use is not different from a use approved by the EPA, the EPA
sees no imminent health hazard in the use, and a tolerance for the pesticide has been established by
the EPA on the crop.
Pesticide Laws and Regulations 29

3.6 ENFORCEMENT

The three laws are enforced from regional laboratories where samples of formulated pesticides
and raw and processed foods that have been collected are analyzed. Pesticide formulations are ana-
lyzed to see if they are properly labeled, that is, they contain the pesticide claimed in the amount
claimed on the label. These analyses will also indicate whether other pesticides, that is, adulterants,
are present. Through complaints, accidents, and investigations of suspected violations, the govern-
ment also receives the attention of any violation of FIFRA (Terriere, 1982).

REFERENCES

Anonymous (1997), The Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) and Federal Food, Drug,
and Cosmetic Act (FFDCA) As Amended by the Food Quality Protection Act (FQPA) of August 3, 1996,
U.S. Environmental Protection Agency, Publication No. 730L97001, 1997.
Bradbury, S., Letter to registrants of nitroguanidine neonicotinoid products, U.S. Environmental Protection
Agency, Washington, DC, August 15, 2013.
EPA (U.S. Environmental Protection Agency), Special Report on Environmental Endocrine Disruption: An
Effects Assessment and Analysis, EPA/630/R-96/012. EPA, Office of Research and Development,
Washington, DC, 1997.
EPA, Label Review Manual, 2nd edn., EPA 737-B-96-001, EPA, Office of Prevention, Pesticide and Toxic
Substances (7505C), Washington, DC, 1996.
EPA, Pesticide Registration Manual, 2014. http://www2.epa.gov/pesticide-registration/pesticide-registration
manual, accessed Jul 30, 2014.
FQPA (Food Quality Protection Act). Public Law 104-170, August 3, 1996.
Terriere, L.C., The Biochemistry and Toxicology of Insecticides, Oregon State University, Corvallis, OR, 1982.
Ware, G.W. and Whitacre, D.W., The Pesticide Book, 6th edn., MeisterPro Information Resources, Willoughby,
OH, 2004.
Exploring the Variety of Random
Documents with Different Content
perceived nothing of the sort, but thanked Absalon for his good
promise and said that he would surely send him the flower.

Abbot Hans had his way. And the following Christmas Eve he did not
sit at home with his monks in Övid Cloister, but was on his way to
Göinge forest. One of Robber Mother's wild youngsters ran ahead of
him, and close behind him was the lay brother who had talked with
Robber Mother in the herb garden.
Abbot Hans had been longing to make this journey, and he was very
happy now that it had come to pass. But it was a different matter
with the lay brother who accompanied him. Abbot Hans was very
dear to him, and he would not willingly have allowed another to
attend him and watch over him; but he didn't believe that he should
see any Christmas Eve garden. He thought the whole thing a snare
which Robber Mother had, with great cunning, laid for Abbot Hans,
that he might fall into her husband's clutches.
While Abbot Hans was riding toward the forest, he saw that
everywhere they were preparing to celebrate Christmas. In every
peasant settlement fires were lighted in the bath-house to warm it
for the afternoon bathing. Great hunks of meat and bread were
being carried from the larders into the cabins, and from the barns
came the men with big sheaves of straw to be strewn over the
floors.
As he rode by the little country churches, he observed that each
parson, with his sexton, was busily engaged in decorating his
church; and when he came to the road which leads to Bösjo Cloister,
he observed that all the poor of the parish were coming with armfuls
of bread and long candles, which they had received at the cloister
gate.
When Abbot Hans saw all these Christmas preparations, his haste
increased. He was thinking of the festivities that awaited him, which
were greater than any the others would be privileged to enjoy.
But the lay brother whined and fretted when he saw how they were
preparing to celebrate Christmas in every humble cottage. He grew
more and more anxious, and begged and implored Abbot Hans to
turn back and not to throw himself deliberately into the robber's
hands.
Abbot Hans went straight ahead, paying no heed to his
lamentations. He left the plain behind him and came up into
desolate and wild forest regions. Here the road was bad, almost like
a stony and burr-strewn path, with neither bridge nor plank to help
them over brooklet and rivulet. The farther they rode, the colder it
grew, and after a while they came upon snow-covered ground.
It turned out to be a long and hazardous ride through the forest.
They climbed steep and slippery side paths, crawled over swamp
and marsh, and pushed through windfall and bramble. Just as
daylight was waning, the robber boy guided them across a forest
meadow, skirted by tall, naked leaf trees and green fir trees. Back of
the meadow loomed a mountain wall, and in this wall they saw a
door of thick boards. Now Abbot Hans understood that they had
arrived, and dismounted. The child opened the heavy door for him,
and he looked into a poor mountain grotto, with bare stone walls.
Robber Mother was seated before a log fire that burned in the
middle of the floor. Alongside the walls were beds of virgin pine and
moss, and on one of these beds lay Robber Father asleep.
"Come in, you out there!" shouted Robber Mother without rising,
"and fetch the horses in with you, so they won't be destroyed by the
night cold."
Abbot Hans walked boldly into the cave, and the lay brother
followed. Here were wretchedness and poverty! and nothing was
done to celebrate Christmas. Robber Mother had neither brewed nor
baked; she had neither washed nor scoured. The youngsters were
lying on the floor around a kettle, eating; but no better food was
provided for them than a watery gruel.
Robber Mother spoke in a tone as haughty and dictatorial as any
well-to-do peasant woman. "Sit down by the fire and warm yourself,
Abbot Hans," said she; "and if you have food with you, eat, for the
food which we in the forest prepare you wouldn't care to taste. And
if you are tired after the long journey, you can lie down on one of
these beds to sleep. You needn't be afraid of oversleeping, for I'm
sitting here by the fire keeping watch. I shall awaken you in time to
see that which you have come up here to see."
Abbot Hans obeyed Robber Mother and brought forth his food sack;
but he was so fatigued after the journey he was hardly able to eat,
and as soon as he could stretch himself on the bed, he fell asleep.
The lay brother was also assigned a bed to rest upon, but he didn't
dare sleep, as he thought he had better keep his eye on Robber
Father to prevent his getting up and capturing Abbot Hans. But
gradually fatigue got the better of him, too, and he dropped into a
doze.
When he woke up, he saw that Abbot Hans had left his bed and was
sitting by the fire talking with Robber Mother. The outlawed robber
sat also by the fire. He was a tall, raw-boned man with a dull,
sluggish appearance. His back was turned to Abbot Hans, as though
he would have it appear that he was not listening to the
conversation.
Abbot Hans was telling Robber Mother all about the Christmas
preparations he had seen on the journey, reminding her of Christmas
feasts and games which she must have known in her youth, when
she lived at peace with mankind. "I'm sorry for your children, who
can never run on the village street in holiday dress or tumble in the
Christmas straw," said he.
At first Robber Mother answered in short, gruff sentences, but by
degrees she became more subdued and listened more intently.
Suddenly Robber Father turned toward Abbot Hans and shook his
clenched fist in his face. "You miserable monk! did you come here to
coax from me my wife and children? Don't you know that I am an
outlaw and may not leave the forest?"
Abbot Hans looked him fearlessly in the eyes. "It is my purpose to
get a letter of ransom for you from Archbishop Absalon," said he. He
had hardly finished speaking when the robber and his wife burst out
laughing. They knew well enough the kind of mercy a forest robber
could expect from Bishop Absalon!
"Oh, if I get a letter of ransom from Absalon," said Robber Father,
"then I'll promise you that never again will I steal so much as a
goose."
The lay brother was annoyed with the robber folk for daring to laugh
at Abbot Hans, but on his own account he was well pleased. He had
seldom seen the Abbot sitting more peaceful and meek with his
monks at Övid than he now sat with this wild robber folk.
Suddenly Robber Mother rose. "You sit here and talk, Abbot Hans,"
she said, "so that we are forgetting to look at the forest. Now I can
hear, even in this cave, how the Christmas bells are ringing."
The words were barely uttered when they all sprang up and rushed
out. But in the forest it was still dark night and bleak winter. The
only thing they marked was a distant clang borne on a light south
wind.
"How can this bell ringing ever awaken the dead forest?" thought
Abbot Hans. For now, as he stood out in the winter darkness, he
thought it far more impossible that a summer garden could spring
up here than it had seemed to him before.
When the bells had been ringing a few moments, a sudden
illumination penetrated the forest; the next moment it was dark
again, and then the light came back. It pushed its way forward
between the stark trees, like a shimmering mist. This much it
effected: The darkness merged into a faint daybreak. Then Abbot
Hans saw that the snow had vanished from the ground, as if some
one had removed a carpet, and the earth began to take on a green
covering. Then the ferns shot up their fronds, rolled like a bishop's
staff. The heather that grew on the stony hills and the bog-myrtle
rooted in the ground moss dressed themselves quickly in new
bloom. The moss-tufts thickened and raised themselves, and the
spring blossoms shot upward their swelling buds, which already had
a touch of color.
Abbot Hans' heart beat fast as he marked the first signs of the
forest's awakening. "Old man that I am, shall I behold such a
miracle?" thought he, and the tears wanted to spring to his eyes.
Again it grew so hazy that he feared the darkness would once more
cover the earth; but almost immediately there came a new wave of
light. It brought with it the splash of rivulet and the rush of cataract.
Then the leaves of the trees burst into bloom, as if a swarm of green
butterflies came flying and clustered on the branches. It was not
only trees and plants that awoke, but crossbeaks hopped from
branch to branch, and the woodpeckers hammered on the limbs
until the splinters fairly flew around them. A flock of starlings from
up country lighted in a fir top to rest. They were paradise starlings.
The tips of each tiny feather shone in brilliant reds, and, as the birds
moved, they glittered like so many jewels.
Again, all was dark for an instant, but soon there came a new light
wave. A fresh, warm south wind blew and scattered over the forest
meadow all the little seeds that had been brought here from
southern lands by birds and ships and winds, and which could not
thrive elsewhere because of this country's cruel cold. These took
root and sprang up the instant they touched the ground.
When the next warm wind came along, the blueberries and lignon
ripened. Cranes and wild geese shrieked in the air, the bullfinches
built nests, and the baby squirrels began playing on the branches of
the trees.
Everything came so fast now that Abbot Hans could not stop to
reflect on how immeasurably great was the miracle that was taking
place. He had time only to use his eyes and ears. The next light
wave that came rushing in brought with it the scent of newly
ploughed acres, and far off in the distance the milkmaids were heard
coaxing the cows—and the tinkle of the sheep's bells. Pine and
spruce trees were so thickly clothed with red cones that they shone
like crimson mantles. The juniper berries changed color every
second, and forest flowers covered the ground till it was all red,
blue, and yellow.
Abbot Hans bent down to the earth and broke off a wild strawberry
blossom, and, as he straightened up, the berry ripened in his hand.
The mother fox came out of her lair with a big litter of black-legged
young. She went up to Robber Mother and scratched at her skirt,
and Robber Mother bent down to her and praised her young. The
horned owl, who had just begun his night chase, was astonished at
the light and went back to his ravine to perch for the night. The
male cuckoo crowed, and his mate stole up to the nests of the little
birds with her egg in her mouth.
Robber Mother's youngsters let out perfect shrieks of delight. They
stuffed themselves with wild strawberries that hung on the bushes,
large as pine cones. One of them played with a litter of young hares;
another ran a race with some young crows, which had hopped from
their nest before they were really ready; a third caught up an adder
from the ground and wound it around his neck and arm.
Robber Father was standing out on a marsh eating raspberries.
When he glanced up, a big black bear stood beside him. Robber
Father broke off an osier twig and struck the bear on the nose.
"Keep to your own ground, you!" he said; "this is my turf." Then the
huge bear turned around and lumbered off in another direction.
New waves of warmth and light kept coming, and now they brought
with them seeds from the star-flower. Golden pollen from rye fields
fairly flew in the air. Then came butterflies, so big that they looked
like flying lilies. The bee-hive in a hollow oak was already so full of
honey that it dripped down on the trunk of the tree. Then all the
flowers whose seeds had been brought from foreign lands began to
blossom. The loveliest roses climbed up the mountain wall in a race
with the blackberry vines, and from the forest meadow sprang
flowers as large as human faces.
Abbot Hans thought of the flower he was to pluck for Bishop
Absalon; but each new flower that appeared was more beautiful
than the others, and he wanted to choose the most beautiful of all.
Wave upon wave kept coming until the air was so filled with light
that it glittered. All the life and beauty and joy of summer smiled on
Abbot Hans. He felt that earth could bring no greater happiness than
that which welled up about him, and he said to himself, "I do not
know what new beauties the next wave that comes can bring with
it."
But the light kept streaming in, and now it seemed to Abbot Hans
that it carried with it something from an infinite distance. He felt a
celestial atmosphere enfolding him, and tremblingly he began to
anticipate, now that earth's joys had come, the glories of heaven
were approaching.
Then Abbot Hans marked how all grew still; the birds hushed their
songs, the flowers ceased growing, and the young foxes played no
more. The glory now nearing was such that the heart wanted to stop
beating; the eyes wept without one's knowing it; the soul longed to
soar away into the Eternal. From far in the distance faint harp tones
were heard, and celestial song, like a soft murmur, reached him.
Abbot Hans clasped his hands and dropped to his knees. His face
was radiant with bliss. Never had he dreamed that even in this life it
should be granted him to taste the joys of heaven, and to hear
angels sing Christmas carols!
But beside Abbot Hans stood the lay brother who had accompanied
him. In his mind there were dark thoughts. "This cannot be a true
miracle," he thought, "since it is revealed to malefactors. This does
not come from God, but has its origin in witchcraft and is sent hither
by Satan. It is the Evil One's power that is tempting us and
compelling us to see that which has no real existence."
From afar were heard the sound of angel harps and the tones of a
Miserere. But the lay brother thought it was the evil spirits of hell
coming closer. "They would enchant and seduce us," sighed he, "and
we shall be sold into perdition."
The angel throng was so near now that Abbot Hans saw their bright
forms through the forest branches. The lay brother saw them, too;
but back of all this wondrous beauty he saw only some dread evil.
For him it was the devil who performed these wonders on the
anniversary of our Saviour's birth. It was done simply for the
purpose of more effectually deluding poor human beings.
All the while the birds had been circling around the head of Abbot
Hans, and they let him take them in his hands. But all the animals
were afraid of the lay brother; no bird perched on his shoulder, no
snake played at his feet. Then there came a little forest dove. When
she marked that the angels were nearing, she plucked up courage
and flew down on the lay brother's shoulder and laid her head
against his cheek.
Then it appeared to him as if sorcery were come right upon him, to
tempt and corrupt him. He struck with his hand at the forest dove
and cried in such a loud voice that it rang throughout the forest, "Go
thou back to hell, whence thou art come!"
Just then the angels were so near that Abbot Hans felt the feathery
touch of their great wings, and he bowed down to earth in reverent
greeting.
But when the lay brother's words sounded, their song was hushed
and the holy guests turned in flight. At the same time the light and
the mild warmth vanished in unspeakable terror for the darkness
and cold in a human heart. Darkness sank over the earth, like a
coverlet; frost came, all the growths shrivelled up; the animals and
birds hastened away; the rushing of streams was hushed; the leaves
dropped from the trees, rustling like rain.
Abbot Hans felt how his heart, which had but lately swelled with
bliss, was now contracting with insufferable agony. "I can never
outlive this," thought he, "that the angels from heaven had been so
close to me and were driven away; that they wanted to sing
Christmas carols for me and were driven to flight."
Then he remembered the flower he had promised Bishop Absalon,
and at the last moment he fumbled among the leaves and moss to
try and find a blossom. But he sensed how the ground under his
fingers froze and how the white snow came gliding over the ground.
Then his heart caused him even greater anguish. He could not rise,
but fell prostrate on the ground and lay there.
When the robber folk and the lay brother had groped their way back
to the cave, they missed Abbot Hans. They took brands with them
and went out to search for him. They found him dead upon the
coverlet of snow.
Then the lay brother began weeping and lamenting, for he
understood that it was he who had killed Abbot Hans because he
had dashed from him the cup of happiness which he had been
thirsting to drain to its last drop.

When Abbot Hans had been carried down to Övid, those who took
charge of the dead saw that he held his right hand locked tight
around something which he must have grasped at the moment of
death. When they finally got his hand open, they found that the
thing which he had held in such an iron grip was a pair of white root
bulbs, which he had torn from among the moss and leaves.
When the lay brother who had accompanied Abbot Hans saw the
bulbs, he took them and planted them in Abbot Hans' herb garden.
He guarded them the whole year to see if any flower would spring
from them. But in vain he waited through the spring, the summer,
and the autumn. Finally, when winter had set in and all the leaves
and the flowers were dead, he ceased caring for them.
But when Christmas Eve came again, he was so strongly reminded
of Abbot Hans that he wandered out into the garden to think of him.
And look! as he came to the spot where he had planted the bare
root bulbs, he saw that from them had sprung flourishing green
stalks, which bore beautiful flowers with silver white leaves.
He called out all the monks at Övid, and when they saw that this
plant bloomed on Christmas Eve, when all the other growths were as
if dead, they understood that this flower had in truth been plucked
by Abbot Hans from the Christmas garden in Göinge forest. Then the
lay brother asked the monks if he might take a few blossoms to
Bishop Absalon.
And when he appeared before Bishop Absalon, he gave him the
flowers and said: "Abbot Hans sends you these. They are the flowers
he promised to pick for you from the garden in Göinge forest."
When Bishop Absalon beheld the flowers, which had sprung from
the earth in darkest winter, and heard the words, he turned as pale
as if he had met a ghost. He sat in silence a moment; thereupon he
said, "Abbot Hans has faithfully kept his word and I shall also keep
mine." And he ordered that a letter of ransom be drawn up for the
wild robber who was outlawed and had been forced to live in the
forest ever since his youth.
He handed the letter to the lay brother, who departed at once for
the Robbers' Cave. When he stepped in there on Christmas Day, the
robber came toward him with axe uplifted. "I'd like to hack you
monks into bits, as many as you are!" said he. "It must be your fault
that Göinge forest did not last night dress itself in Christmas bloom."
"The fault is mine alone," said the lay brother, "and I will gladly die
for it; but first I must deliver a message from Abbot Hans." And he
drew forth the Bishop's letter and told the man that he was free.
"Hereafter you and your children shall play in the Christmas straw
and celebrate your Christmas among people, just as Abbot Hans
wished to have it," said he.
Then Robber Father stood there pale and speechless, but Robber
Mother said in his name, "Abbot Hans has indeed kept his word, and
Robber Father will keep his."
When the robber and his wife left the cave, the lay brother moved in
and lived all alone in the forest, in constant meditation and prayer
that his hard-heartedness might be forgiven him.
But Göinge forest never again celebrated the hour of our Saviour's
birth; and of all its glory, there lives to-day only the plant which
Abbot Hans had plucked. It has been named Christmas Rose. And
each year at Christmastide she sends forth from the earth her green
stalks and white blossoms, as if she never could forget that she had
once grown in the great Christmas garden at Göinge forest.
 A Story from Jerusalem
In the old and time-honored mosque, El Aksa, in Jerusalem, there is
a long, winding path leading from the main entrance up to a very
deep and wide window-niche. In this niche a very old and much
worn rug is spread; and upon this rug, day in and day out, sits old
Mesullam, who is a fortune-teller and dream-interpreter, and who for
a paltry penny serves the visitors to the mosque by prying into their
future destinies.
It happened one afternoon, several years ago, that Mesullam, who
sat as usual in his window, was so ill-natured that he wouldn't even
return the greetings of the passers-by. No one thought, however, of
feeling offended at his rudeness, because every one knew that he
was grieving over a humiliation which had been put upon him that
day.
At that time a mighty monarch from the Occident was visiting
Jerusalem, and in the forenoon the distinguished stranger with his
retinue had wandered through El Aksa. Before his arrival the
superintendent of the mosque had commanded the servants to
scour and dust all the nooks and corners of the old building, at the
same time giving orders that Mesullam should move out of his
accustomed place. He had found that it would be simply impossible
to let him remain there during the visit of the distinguished guest. It
was not only that his rug was very ragged, or that he had piled up
around him a lot of dirty sacks in which he kept his belongings, but
Mesullam himself was anything but an ornament to the mosque! He
was, in reality, an inconceivably ugly old negro. His lips were
enormous, his chin protruded aggressively, his brow was exceedingly
low, and his nose was almost like a snout; and in addition to these,
Mesullam had a coarse and wrinkled skin and a clumsy, thick-set
body, which was carelessly draped in a dirty white shawl. So one
can't wonder that he was forbidden to show himself in the mosque
while the honored guest was there!
Poor Mesullam, who knew well enough that, despite his ugliness, he
was a very wise man, experienced a bitter disappointment in that he
was not to see the royal traveller. He had hoped that he might give
him some proofs of the great accomplishments which he possessed
in occult things and in this way add to his own glory and renown.
Since this hope had miscarried, he sat hour after hour in a queer
position, and mourned, with his long arms stretched upward and his
head thrown far back, as though he were calling upon heaven for
justice.
When it drew on toward evening, Mesullam was wakened from his
state of all-absorbing grief by a cheery voice calling him. It was a
Syrian who, accompanied by another traveller, had come up to the
soothsayer. He told him that the stranger whom he was conducting
wished for a proof of Oriental wisdom, and that he had spoken to
him of Mesullam's ability to interpret dreams.
Mesullam answered not a word to this, but maintained his former
attitude rigidly. When the guide asked him again if he would not
listen to the dreams the stranger wished to relate to him and
interpret them, his arms dropped and he crossed them on his breast.
Assuming the attitude of a wronged man, he answered that this
evening his soul was so filled with his own troubles that he couldn't
judge anything clearly which concerned another.
But the stranger, who had a buoyant and commanding personality,
didn't seem to mind his objections. As there was no chair handy, he
kicked aside the rug and seated himself in the window-niche. Then
he began, in a clear and vibrant voice, to narrate a few dreams,
which later were translated for the soothsayer by the guide.
"Tell him," said the traveller, "that a few years ago I was at Cairo, in
Egypt. Since he is a learned man, naturally he knows there is a
mosque there, called El Azhar, which is the most celebrated
institution of learning in the Orient. I went there one day to visit it,
and found that the whole colossal structure—all its rooms and
arcades, all its entrances and halls were filled with students. There
were old men who had devoted their entire lives to the quest for
knowledge, and children who were just learning to form their letters.
There were giantesque negroes from the heart of Africa; lithe,
handsome youths from India and Arabia; far-travelled strangers from
Barbary, from Georgia, from every land where the natives embrace
the doctrines of the Koran. Close to the pillars—I was told that in El
Azhar there were as many teachers as there were pillars—the
instructors were squatted on their rugs, while their students, who
were arranged in a circle around them, eagerly followed their
lectures, which were accompanied by swaying movements of their
bodies. And tell him that, although El Azhar is in no way comparable
to the great Occidental seats of learning, I was nevertheless
astonished at what I saw there. I remarked to myself: 'Ah, this is
Islam's great stronghold and defence! From here Mohammed's
young champions go out. Here, at El Azhar, the potions of wisdom
that keep the Koran's doctrines healthy and vigorous are blended.'"
All of this the traveller said almost in one breath. Now he made a
pause, so that the guide would have an opportunity to interpret for
the soothsayer. Then he continued:
"Now tell him that El Azhar made such a powerful impression upon
me that on the following night I saw it again in a dream. I saw the
white marble structure and the many students dressed in white
mantles and white turbans—as is the custom at El Azhar. I wandered
through halls and courts and was again astonished at what a
splendid fortress and wall of protection this was for
Mohammedanism. Finally—in the dream—I came to the minaret
upon which the prayer-crier stands to inform the faithful that the
hour of prayer has struck. And I saw the stairway which winds up to
the minaret, and I saw a prayer-crier walking up the steps. He wore
a black mantle and a white turban, like the others, and as he went
up the stairs I could not at first see his face, but when he had made
a few turns on the spiral stairway, he happened to turn his face
toward me, and then I saw that it was Christ."
The speaker made a short pause, and his chest was expanded for a
deep inhalation. "I shall never forget, although it was only a dream,"
he exclaimed, "what an impression it made upon me to see Christ
walking up the steps to the minaret in El Azhar! To me it seemed so
glorious and significant that he had come to this stronghold of Islam
to call out the hours of prayer that I leaped up in the dream and
awaked."
Here the traveller made another pause to let the guide interpret for
the soothsayer. But this appeared to be well-nigh useless labor.
Mesullam sat all the while, with his hands on his sides, rocking back
and forth, and with his eyes half closed. He seemed to want to say:
"Inasmuch as I cannot escape these importunate people, at least I
will let them see that I don't care to listen to what they have to say.
I'll try and rock myself to sleep. It will be the best way to show them
how little I care about them."
The guide intimated to the traveller that all their trouble would be in
vain and they wouldn't hear a sensible word from Mesullam while he
was in this mood. But the European stranger seemed to be
entranced by Mesullam's indescribable ugliness and extraordinary
behavior. He looked at him with the pleasure of a child when it is
watching a wild animal in a menagerie, and he desired to continue
the interview.
"Tell him that I wouldn't have troubled him to interpret this dream,"
he said, "had it not, in a certain sense, come to me again. Let him
know that two weeks ago I visited the Sophia Mosque at
Constantinople, and that I, after wandering through this magnificent
building, stepped up on a minaret in order to get a better view of
the auditorium. Tell him, also, that they allowed me to come into the
mosque during a service, when it was filled with people. Upon each
of the innumerable prayer rugs which covered the whole floor of the
main hall, a man was standing and saying his prayers. All who took
part in the service simultaneously made the same movements. All
fell upon their knees and threw themselves on their faces and raised
themselves, at the same time whispering their prayers very low; but
from the almost imperceptible movements of so many lips came a
mysterious murmur, which rose toward the high arches and died
away, time and again. Then there came melodious responses from
remote passages and galleries. It was so strange altogether that one
wondered if it was not the Spirit of God that poured into the old
sanctuary."
The traveller made another pause. He observed Mesullam carefully,
while the guide interpreted his speech. It actually appeared as if he
had tried to win the negro's approbation with his eloquence. And it
seemed, too, as though he would succeed, for Mesullam's half-
closed eyes flashed once, like a coal that is beginning to take fire.
But the soothsayer, stubborn as a child that will not let itself be
amused, dropped his head on his breast and began an even more
impatient rocking of his body.
"Tell him," resumed the stranger, "tell him that I have never seen
people pray with such fervor! To me it seemed as if it was the
sublime beauty of this marvellous structure which created this
atmosphere of ecstasy. Verily this is still an Islam bulwark! This is
the home of devoutness! From this great mosque emanate the faith
and enthusiasm which make Islam a mighty power."
Here he paused again, noting carefully Mesullam's play of features
during its interpretation. Not a trace of interest was discernible in
them. But the stranger was evidently a man who liked to hear
himself talk. His own words intoxicated him; he would have become
ill-natured had he not been allowed to proceed.
"Well," said he, when it was his turn again to speak, "I cannot rightly
explain what happened to me. Possibly the faint odor from the
hundreds of oil lamps, together with the low murmurings of the
devotees, lulled me into a kind of stupefaction. I could not help but
close my eyes as I stood leaning against a pillar. Soon sleep, or
rather insensibility, overcame me. Probably it did not last more than
a minute, but during this interval I was entirely removed from reality.
While in this trance I could see the whole Sophia Mosque before me,
with all the praying people; but now I saw what I had not hitherto
observed. Up in the dome were scaffoldings, and on these stood a
number of workmen with paint pots and brushes.
"Tell him, if he does not already know it," continued the narrator,
"that Sophia Mosque was once a Christian church, and that its
arches and dome are covered with sacred Christian mosaics,
although the Turks have painted out all these pictures with plain
yellow paint. And it appeared to me as if the yellow paint in the
dome had peeled off in a couple of places and that the painters had
clambered up on the scaffolding to touch up the picture. But, look!
when one of them raised his brush to fill in the color, another large
piece scaled off, and suddenly one saw from behind it a beautiful
painting of the Christ emerge. Again the painter raised his arm to
paint out the picture, but the arm, which appeared to be numb and
powerless, dropped down before this beautiful face; at the same
time the paint dropped from the entire dome and arch, and Christ
was visible there in all his glory, among angels and heavenly hosts.
Then the painter cried out, and all the worshippers down on the
floor of the mosque raised their heads. And when they saw the
heavenly hosts surrounding the Saviour, they sent up a cry of joy,
and when I witnessed this joy, I was seized with such strong
emotion that I waked instantly. Then everything was like itself. The
mosaics were hidden under the yellow paint and the devotees
continued all the while to invoke Allah."
When the interpreter had translated this, Mesullam opened one eye
and regarded the stranger. He saw a man who he thought resembled
all other Occidentals that wandered through the mosque. "I don't
believe the pale-faced stranger has seen any visions," thought he.
"He has not the dark eyes that can see what is behind the veil of
mystery. I think, rather, that he came here to make sport of me. I
must beware lest on this accursed day I be overtaken by another
humiliation."
The stranger spoke anon: "You know, O Dream Interpreter!" turning
now direct to Mesullam, as if he thought that he could understand
him, despite his foreign tongue—"you know that a distinguished
foreigner is visiting Jerusalem at present, and on his account they
have talked of opening the walled-up gate in Jerusalem's ring-wall—
the one they call 'the Golden' and which is believed to be the gate
through which Jesus rode into Jerusalem on Palm Sunday. They have
actually been thinking of doing the distinguished traveller the honor
of letting him ride into the city through a gate which has been walled
up for centuries; but they were held back by an old prophecy which
foretells that when this gate is opened the Occidentals will march in
through it to take possession of Jerusalem.
"And now you shall hear what happened to me last night. The
weather was superb; it was glorious moonlight, and I had gone out
alone to take a quiet promenade around the Holy City. I walked
outside the ring-wall on the narrow path that extends all round the
wall, and my thoughts were borne so far back into distant ages that
I scarcely remembered where I was. All of a sudden I began to feel
tired. I wondered if I should not soon come to a gate in the wall,
through which I might get into the city and thus return to my
quarters by a shorter road. Well, just as I was thinking of this, I saw
a man open a large gate in the wall directly in front of me. He
opened it wide and beckoned to me that I might pass in through it. I
was absorbed in my dreams and hardly knew how far I had been
walking. I was somewhat surprised that there was a gate here, but I
thought no more about the matter and walked through it. As soon as
I had passed through the deep archway, the gate closed with a
sharp clang. When I turned round, there was no opening visible,
only a walled-up gate—the one called the Golden. Before me lay the
temple place, the broad Haram plateau, in the centre of which
Omar's Mosque is enthroned. And you know that no gate in the ring-
wall leads thither but the Golden, which is not only closed but walled
up.
"You can understand that I thought I'd gone mad; that I dreamed I
had tried in vain to find some explanation of this. I looked around for
the man who had let me in. He had vanished and I could not find
him. But, on the other hand, I saw him all the plainer in memory—
the tall and slightly bent figure, the beautiful locks, the mild visage,
the parted beard. It was Christ, soothsayer, Christ once again.
"Tell me now, you who can look into the hidden, what mean my
dreams? What, more than all, can be the meaning of my having
really and truly passed through the Golden Gate? Even at this
moment I do not know how it happened, but I have done so. Tell
me, now, what these three things can mean!"
The interpreter translated this for Mesullam, but the soothsayer was
all the while in the same suspicious and crabbed mood. "I am certain
that this stranger wants to poke fun at me," he thought. "Perchance
he would provoke me to anger with all this talk about Christ?"
He would have concluded not to answer at all; but when the
interpreter insisted, he muttered a few words.
"What does he say?" asked the traveller eagerly.
"He says he has nothing to say to you but that dreams are dreams."
"Then tell him from me," retorted the stranger, somewhat
exasperated, "that this is not always true. It depends entirely upon
who dreams them."
Before these words had been interpreted to Mesullam, the European
had arisen and with quick and elastic step had walked toward the
long passage-way.
But Mesullam sat still and mused over his answer for five minutes.
Then he fell upon his face, utterly undone. "Allah, Allah! Twice on
the same day Fortune has passed by me without my having
captured her. What hath thy servant done to displease thee?"
 Why the Pope Lived to be so Old
It happened at Rome in the early nineties. Leo XIII was just then at
the height of his fame and greatness. All true Catholics rejoiced at
his successes and triumphs, which in truth were sublime. And, even
for those who could not grasp the great political events, it was plain
that the power of the Church was again coming to the front. Any
one at all could see that new cloisters were going up everywhere
and that throngs of pilgrims were beginning to pour into Italy, as in
olden times. In many, many places one saw the old, dilapidated
churches in process of restoration, damaged mosaics being put in
order, and the treasure-vaults of the churches being filled with
golden relic-boxes and jewelled exhibits.
Right in the midst of this progressive period the Roman people were
alarmed by the news that the Pope had been taken ill. He was said
to be in a very precarious condition; it was even rumored that he
was dying.
His condition was, too, in a great degree serious. The Pope's
physicians issued bulletins which inspired but little hope. It was
maintained that the Pope's great age—he was then eighty years old
—made it seem almost incredible that he could survive this attack.
Naturally, the Pope's illness caused great unrest. In all the churches
in Rome prayers were said for his recovery. The newspapers were
filled with communications regarding the progress of the illness. The
Cardinals were beginning to take steps and measures for the new
Papal election.
Everywhere they bemoaned the approaching demise of the brilliant
leader. They feared that the good fortune which had followed the
Church's standard under Leo XIII might not be faithful to it under
the leadership of his successor. There were many who had hoped
that this Pope would succeed in winning back Rome and the
Ecclesiastical States. Others, again, had dreamed that he would
bring back into the bosom of the Church some of the large
Protestant countries.
For each second that was passing, fear and anxiety grew apace. As
night came on, in many homes the inmates would not retire. The
churches were kept open until long past midnight, that the anxious
ones might have an opportunity to go in and pray.
Among these throngs of devotees there was certainly more than one
poor soul who cried out: "Dear Lord, take my life instead of his! Let
him, who has done so much for Thy glory, live, and extinguish
instead my life-flame, which burns to no one's use!"
But if the Angel of Death had taken one of these devotees at his
word and had suddenly stepped up to him, with sword raised, to
exact the fulfilment of his promise, one might wonder somewhat as
to how he would have behaved. No doubt he would have recalled
instantly such a rash proffer and begged for the grace of being
allowed to live out all the years of his allotted time.
At this time there lived an old woman in one of the dingy ramshackle
houses along the Tiber. She was one of those who have the kind of
spirit that thanks God every day for life. Every morning she used to
sit at the market-place and sell garden truck. And this was an
occupation that was very congenial to her. She thought nothing
could be livelier than a market of a morning. All tongues were
wagging—all were harking their commodities, and buyers crowded in
front of the stalls, selected and bargained, and many a good sally
passed between buyer and seller. Sometimes the old woman was
successful in making a good deal and in selling out her entire stock;
but even if she couldn't sell so much as a radish, she loved to be
standing amongst flowers and green things in the fresh morning air.
In the evening she had another and an even greater pleasure. Then
her son came home and visited with her. He was a priest, but he had
been assigned to a little church in one of the humble quarters. The
poor priests who served there had not much to live upon, and the
mother feared that her son was starving. But from this, also, she
derived much pleasure, for it gave her the opportunity of stuffing
him full of delicacies when he came to see her. He struggled against
it, as he was destined for a life of self-denial and strict discipline, but
his mother became so distressed when he said no that he always
had to give in. While he was eating she trotted around in the room
and chattered about all that she had seen in the morning during
market hours. These were all very worldly matters, and it would
occur to her sometimes that her son might be offended. Then she
would break off in the middle of a sentence and begin to talk of
spiritual and solemn things, but the priest couldn't help laughing.
"No, no, mother Concenza!" he said, "continue in your usual way.
The saints know you already, and they know what you are up to."
Then she, too, laughed and said: "You are quite right. It doesn't pay
to pretend before the good Lord."
When the Pope was taken ill, Signora Concenza must also have a
share in the general grief. Of her own accord it certainly never would
have occurred to her to feel troubled about his passing. But when
her son came home to her, she could neither persuade him to taste
of a morsel of food nor to give her a smile, although she was simply
bubbling over with stories and interpolations. Naturally she became
alarmed and asked what was wrong with him. "The Holy Father is
ill," answered the son.
At first she could scarcely believe that this was the cause of his
downheartedness. Of course it was a sorrow; but she knew, to be
sure, that if a Pope died, immediately there would come another.
She reminded her son of the fact that they had also mourned the
good Pio Nono. And, you see, the one who succeeded him was a still
greater Pope. Surely the Cardinals would choose for them a ruler
who was just as holy and wise as this one.
The priest then began telling her about the Pope. He didn't bother to
initiate her into his system of government, but he told her little
stories of his childhood and young manhood. And from the days of
his prelacy there were also things to relate—as, for instance, how he
had at one time hunted down robbers in southern Italy, how he had
made himself beloved by the poor and needy during the years when
he was a bishop in Perugia.
Her eyes filled with tears, and she cried out: "Ah, if he were not so
old! If he might only be allowed to live many more years, since he is
such a great and holy man!"
"Ah, if only he were not so old!" sighed the son.
But Signora Concenza had already brushed the tears from her eyes.
"You really must bear this calmly," said she. "Remember that his
years of life are simply run out. It is impossible to prevent death
from seizing him."
The priest was a dreamer. He loved the Church and had dreamed
that the great Pope would lead her on to important and decisive
victories. "I would give my life if I could purchase new life for him!"
said he.
"What are you saying?" cried his mother. "Do you really love him so
much? But, in any case, you must not express such dangerous
wishes. Instead, you should think of living a good long time. Who
knows what may happen? Why couldn't you, in your turn, become
Pope?"
A night and a day passed without any improvement in the Pope's
condition. When Signora Concenza met her son the following day, he
looked completely undone. She understood that he had passed the
whole day in prayer and fasting, and she began to feel deeply
grieved. "I verily believe that you mean to kill yourself for the sake
of that sick old man!" said she.
The son was hurt by again finding her without sympathy, and tried
to persuade her to sympathize a little with his grief. "You, truly, more
than any one else, ought to wish that the Pope might live," he said.
"If he may continue to rule, he will name my parish priest for bishop
before the year shall have passed and, in that event, my fortune is
made. He will then give me a good place in a cathedral. You shall
not see me going about any more in a worn-out cassock. I shall
have plenty of money, and I shall be able to help you and all your
poor neighbors."
"But if the Pope dies?" asked Signora Concenza breathlessly.
"If the Pope dies, then no one can know—If my parish priest doesn't
happen to be in favor with his successor, we must both remain
where we now are for many years to come."
Signora Concenza came close to her son and regarded him
anxiously. She looked at his brow, which was covered with wrinkles,
and at his hair that was just turning gray. He looked tired and worn.
It was actually imperative that he should have that place at the
cathedral right away. "To-night I shall go to church and pray for the
Pope," thought she. "It won't do for him to die."
After supper she bravely conquered her fatigue and went out on the
streets. Great crowds of people thronged there. Many were only
curious and had gone out because they wished to catch the news of
the death at first hand; but many were really distressed and
wandered from church to church to pray.
As soon as Signora Concenza had come out on the street, she met
one of her daughters, who was married to a lithographer. "Oh,
mother, but you do right to come out and pray for him!" exclaimed
the daughter. "You can't imagine what a misfortune it would be if he
were to die! My Fabiano was ready to take his own life when he
learned that the Pope was ill."
She related how her husband, the lithographer, had but just struck
off hundreds of thousands of the Pope's pictures. Now, if the Pope
were to die, he wouldn't be able to sell half of them—no, not even a
quarter of them. He would be ruined. Their entire fortune was at
stake.
She rushed on to gather some fresh news, wherewith she might
comfort her poor husband, who did not dare venture out, but sat at
home and brooded over his misfortune. Her mother stood still on the
street, mumbling to herself: "It won't do for him to die. It will never
do for him to die!"
She walked into the first church she came to. There she fell upon
her knees and prayed for the life of the Pope.
As she arose to leave, she happened to lift her eyes to a little votive
tablet which hung on the wall just above her head. The tablet was a
representation of Death raising a terrifying two-edged sword to mow
down a young girl, while her mother, who had cast herself in his
path, tries in vain to receive the blow in place of her child.
She stood long before the picture, musing. "Signor Death is a careful
arithmetician," she remarked. "One has never heard of his agreeing
to exchange an old person for a young one."
She remembered her son's words that he would be willing to die in
the Pope's stead, and a shudder passed through her whole body.
"Think, if Death were to take him at his word!"
"No, no, Signor Death!" she whispered. "You mustn't believe him.
You must understand that he didn't mean what he said. He wants to
live. He doesn't want to leave his old mother, who loves him."
For the first time the thought struck her that if any one should
sacrifice himself for the Pope, it were better that she did it—she,
who was already old and had lived her life.
When she left the church, she happened into the company of some
nuns of the saintliest and most devout appearance, who lived in the
northern part of the country. They had travelled down to Rome to
obtain a little help from the Pope's treasury. "We are actually in the
most dire need of aid," they told old Concenza. "Only think! our
convent was so old and dilapidated that it blew down during the
severe storm of last winter. We may not now present our case to
him. If he should die, we must return home with an unaccomplished
mission. Who can know if his successor will be the sort of man who
will trouble himself to succor poor nuns?"
It seemed as if all the people were thinking the same thoughts. It
was very easy to get into converse with any one. Each and all whom
Signora Concenza approached let her know that the Pope's death
would be for them a terrible misfortune.
The old woman repeated again and again to herself: "My son is
right. It will never do for the Pope to die."
A nurse was standing among a group of people, talking in a loud
voice. She was so affected that the tears streamed down her cheeks.
She related how five years ago she had been ordered away, to serve
at a leper hospital on an island at the other end of the globe.
Naturally, she had to obey orders; but she did so against her wishes.
She had felt a horrible dread of this mission. Before she left Rome,
she was received by the Pope, who had given her a special blessing
and had also promised her that if she came back alive she should
have another audience with him. And it was upon this that she had
lived during the five years she had been away—only on the hope
that she might see the Holy Father once more in this life! This had
helped her to go through all the horrors. And now, when she had
got home at last, she was met by the news that he lay upon his
death-bed! She could not even see him!
She was in extreme despair, and old Concenza was deeply moved.
"It would really be much too great a sorrow for every one if the
Pope were to die," thought she, as she wandered farther up the
street.
When she observed that many of the passers-by looked perfectly
exhausted from weeping, she thought with a sense of relief: "What a
joy it would be to see everybody's happiness if the Pope should
recover!" And she, like many others who have a buoyant disposition,
was apparently no more afraid of dying than of living; so she said to
herself: "If I only knew how it could be done, I would gladly give the
Holy Father the years that are left to me of life."
She said this somewhat in jest, but back of the words there was also
seriousness. She truly wished that she might realize something in
that way. "An old woman could not wish for a more beautiful death,"
thought she. "I would be helping both my son and my daughter,
and, besides, I should make great masses of people happy."
Just as this thought stirred within her, she raised the patched curtain
which hung before the entrance of a gloomy little church. It was one
of the very old churches—one of those which appear to be gradually
sinking into the earth because the city's foundation has, in the
intervening years, raised itself several metres all around them. This
church in its interior had preserved somewhat of its ancient gloom,
which must have come down through the dark ages during which it
had sprung into existence. Involuntarily a shudder passed through
one as one stepped in under its low arches, which rested upon
uncommonly thick pillars, and saw the crudely painted saints'
pictures that glimpsed down at one from walls and altars.
When Signora Concenza came into this old church, which was
thronged with worshippers, she was seized with a mysterious awe
and reverence. She felt that in this sanctuary there verily lived a
Deity. Beneath the massive arches hovered something infinitely
mighty and mysterious, something which inspired such a sense of
annihilating superiority that she felt nervous about remaining in
there. "Ah, this is no church where one goes to hear a mass or to
confessional," remarked Signora Concenza to herself. "Here one
comes when one is in great trouble, when one can be helped in no
other way than through a miracle."
She lingered down by the door and breathed in this strange air of
mystery and gloom. "I don't even know to whom this old church is
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