Innovations for safe and sustainable crop protection products

Safe and Sustainable Crop Protection......Page 2
 Safe and Sustainable Crop Protection......Page 4
  Library of Congress Cataloging-in-Publication Data......Page 5
Foreword......Page 6
Subject Index......Page 8
Preface......Page 10
The Microbiome of Fruit Flies as Novel Targets for Pest Management......Page 12
 Invasive Fruit Flies: Small Insects of Big Economic Importance......Page 13
 Current Status and Challenges of Fruit Fly Management......Page 20
 The Fruit Flies’ Microbiome: Who Are the Players?......Page 21
 Microbial Influence on Fruit Flies: Nutrition, Behavior, and Insecticide Resistance......Page 23
 Leveraging Microbiomes to Develop Novel Management Strategies for Fruit Flies: Lessons from Different Insects......Page 25
 Disruption of Microbiomes......Page 26
 Paratransgenesis......Page 28
 Attractants......Page 30
 Optimization of SITs Using Probiotics......Page 31
 References......Page 32
Modular Approach to Macrocyclic Picolinamides......Page 50
 Figure 1. Structure of UK-2A.......Page 51
  Figure 4. Macrocycle CAS-381 contains fewer esters and displays improved stability.......Page 52
 Maximizing Synthetic Accessibility......Page 53
 Synthesis of the Stereotriads......Page 54
  Figure 10. Addition of an alcohol stereotriad into a Boc-aziridine carboxylate under Lewis acidic conditions.......Page 55
 Modular Construction......Page 56
  Figure 14. Scaffold markush for macrocycle derivatives with variations at the X,Y, and Z positions.......Page 57
 References......Page 59
 Background......Page 62
 HRMS Analyzers......Page 63
 Orbitrap......Page 64
 Ionization Sources......Page 65
 Other MS Technologies Applicable for Small-Molecule Structure Elucidation......Page 66
 Typical Workflow for Impurity Identification......Page 67
 GC/MS Study of Impurities in a Commercial Chlorpyrifos Sample......Page 68
  Figure 4. The total ion chromatograms of (a) Chlorpyrifos and (b) Chlorpyrifos derivatized with BSTFA.......Page 69
  Scheme 2. Haloxyfop-P Methyl Ester......Page 70
  Figure 7. The positive ion ESI mass spectrum of Haloxyfop-P methyl ester showing [M + H]+, [M + Na]+, and [M + K]+.......Page 71
  Figure 9. The negative ion ESI mass spectrum of Haloxyfop-P methyl ester showing [M − H]-, [M + O − H]+, and [M + O2 − H]+.......Page 72
  Figure 11. The positive ion ESI MS/MS spectrum of [M + H]+ ions of Imp 1.......Page 73
 Conclusion......Page 74
 References......Page 75
 Introduction......Page 78
 Workflow for Development of Chiral Separation Methods......Page 79
  Figure 1. Progression of chiral separation method development. (1) Receive racemic and enantioenriched sample. (2) Identify mobile phase composition. (3) Perform chiral stationary phase screening. (4) Optimize separation on best stationary phase. (5) Run both samples using optimized separation conditions and optimized sample prep. (6) Document method.......Page 80
 Key Learnings......Page 81
  Figure 3. Mixture of four isomers to be separated, containing two pairs of enantiomers.......Page 82
  Figure 4. Progression of separation during method development using an OJ chiral stationary phase. (1) 15% IPA/hex at 40 °C. (2) 3% IPA/hex at 20 °C (first injection). (3) 1% IPA/hex at 20 °C. (4) 3% IPA/hex at 20 °C (second injection).......Page 83
  Figure 6. Racemic molecule that needs to be separated into its enantiomers.......Page 84
  Figure 8. Optimization of chiral separation conditions. (1) 2 mL/min, 5 μL injection of 1 mg/mL solution (0.005 mg), 214 nm. (2) 2 mL/min, 100 μL injection of 1 mg/mL solution (0.1 mg), 214 nm. (3) 2 mL/min, 100 μL injection of 10 mg/mL (1 mg), 214 nm. (4) 2 mL/min, 100 μL injection of 10 mg/mL (1 mg), 254 nm.......Page 85
  Figure 10. Modified instrumentation configuration to allow analytical-scale isolation.......Page 86
 Example 3: Application to Formulations......Page 87
  Figure 15. Chiral separation developed for racemic material was used to analyze enantioenriched technical, which was then used to generate a formulation for field trials.......Page 88
  Figure 17. Analysis of enantioenriched technical and formulation after 2 weeks at room temperature.......Page 89
  Figure 20. Loss of enantiopurity observed upon addition of alkylamide solvent and dimethylamine to the formulation.......Page 90
 Acknowledgments......Page 91
 References......Page 92
 Introduction......Page 94
  Figure 1. Time difference of RP separation vs SFC separation of two chiral molecules.......Page 95
  Figure 2. RPLC conditions and chromatograms.......Page 96
  Figure 3. Conditions and representative chromatograms of proton donor evaluation.......Page 97
  Figure 4. Calibration curves of prothioconazole from 50 to 6500 ppb with water added through the modifier and makeup flow and without water.......Page 98
  Figure 5. RPLC and SFC ionization comparisons of prothioconazole.......Page 99
  Figure 6. RPLC and SFC ionization comparisons of prothioconazole-desthio.......Page 100
  Figure 7. Comparison of prothioconazole ionization efficiency using optimal mode and polarity in RPLC and SFC.......Page 101
  Figure 8. Comparison of prothioconazole-desthio ionization efficiency using optimal mode and polarity in RPLC and SFC.......Page 102
  Figure 10. SFC plot of S/N at different concentrations.......Page 103
 References......Page 104
 Introduction......Page 106
 Methodology......Page 107
 Results and Discussion......Page 108
  Figure 3. Kinetics model for oxime degradation.......Page 109
  Figure 5. Oxamyl degradation pathway.......Page 110
  Figure 6. Oxamyl degradation and optimized data fit in soil.......Page 111
  Figure 8. Optimized kinetics for conversion of cymoxanil to metabolites, NER, and CO2.......Page 112
  Figure 9. Soil degradation pathway for cyhalofop butyl.......Page 113
  Figure 10. Optimized kinetics for degradation of cyhalofop butyl.......Page 114
  Figure 12. Optimized kinetics degradation of famoxadone and its metabolite H3310 in soil.......Page 115
 References......Page 116
Creating Environmentally Resilient Agriculture Landscapes Using Precision Agriculture Technology: An Economic Perspective......Page 118
 Introduction......Page 119
 Incentive-Based Conservation......Page 120
 Precision Agriculture Technology......Page 121
 Precision Agriculture Application for Pesticide Mitigation......Page 122
  Figure 2. Profit surface (dollar per acre) for a production soybean field in Lowndes County, Mississippi. Net Rev: net revenue.......Page 123
  Figure 3. Total eligible area for CP-33, Filter Strips, on a grain farm in Tallahatchie, Mississippi. Reproduced with permission from reference 30. Copyright 2016 American Society of Agronomy, Crop Science Society of America, Soil Sciences Society of America.......Page 124
  Figure 4. Total eligible area for CP-21, Habitat Buffers for Upland Birds, on a grain farm in Tallahatchie, Mississippi. Reproduced with permission from reference 30. Copyright 2016 American Society of Agronomy, Crop Science Society of America, Soil Sciences Society of America.......Page 125
  Figure 6. Profit surface (dollar per acre) for a production soybean field with 120-foot CP-33, Habitat Buffers for Upland Birds, scenario in Lowndes County, Mississippi. Net Rev: net revenue.......Page 126
 Discussion......Page 127
 References......Page 128
 The Evolution, History, and Market Demand for Contract Research Organizations......Page 134
 The Regulatory Reality......Page 135
 Managing Data......Page 137
 The Role of the SD......Page 139
 The Challenge of Flexibility......Page 140
 The Challenge of New Technology......Page 141
 Conclusions......Page 142
 References......Page 143
 Qi Yao......Page 144
Indexes......Page 146
Author Index......Page 148
 I......Page 150
 N......Page 151
 P......Page 152