Recent Highlights in the Discovery and Optimization of Crop Protection Products

1st Edition - March 24, 2021
Imprint: Academic Press
Editors: Peter Maienfisch, Ir. Sven Mangelinckx
Language: English
Paperback ISBN:
9 7 8 - 0 - 1 2 - 8 2 1 0 3 5 - 2
eBook ISBN:
9 7 8 - 0 - 1 2 - 8 2 1 0 3 6 - 9

Recent Highlights in the Discovery and Optimization of Crop Protection Products highlights the most prominent, recent results in the search for safe and effective new crop prot… Read more

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Recent Highlights in the Discovery and Optimization of Crop Protection Products highlights the most prominent, recent results in the search for safe and effective new crop protection products. With a focus on the design, synthesis, optimization and/or structure-activity relationships of new chemistries targeting insect, disease, weed, nematode, vector and animal parasite control, the book also includes recent developments in crop enhancement chemistries and new approaches to crop protection products. The inclusion of information on testing tools, green chemistry approaches, and the latest discovery tools, like modeling, structure-based design, and testing tools makes this volume complete.

Based on key presentations given at the 14th International IUPAC conference on Crop Protection, May 19-24, 2019 in Ghent, Belgium, this book includes the many exciting new discoveries and findings reported. It is designed to inspire additional research and advancement in the field.

Cover image
Title page
Table of Contents
Copyright
List of Contributors
About the editors
Preface
Chapter 1. Recent innovation in crop protection research
Abstract
Introduction
Recent innovation in insecticide research
Recent innovation in disease control research
Recent innovation in virus, vector, animal parasite, and nematode control research
Recent innovation in herbicide research
Recent innovation in crop enhancement research
Recent innovation in green crop protection research
Conclusion
Acknowledgments
References
Chapter 2. Status and potential of bioprotection products for crop protection
Abstract
Defining biopesticides
Market factors for biopesticides (bioprotection)
Chemical versus biopesticide development
Investment in biopesticides
Biopesticide discovery and development process
Comparison of chemical versus biopesticide development business models
Barriers to adoption of biopesticides
What is the future for biopesticides?
Conclusion
Biopesticide resources
References
Chapter 3. Research and development of green pesticides in China
Abstract
Green pesticides
Basic research of pesticides in China
Pesticides registered in China
Future trend
Acknowledgment
References
Chapter 4. Agrochemical disease control: The story so far
Abstract
Introduction and historical perspective
Sterol biosynthesis inhibitors
Respiration inhibitors
Oomycetes-selective fungicides
Resistance development
Conclusion
Acknowledgments
References
Chapter 5. Plant defense priming in the field: a review
Abstract
A note on terminology
Known priming agents: an overview
Field trials with priming agents
Priming in woody perennials
Priming in herbaceous horticultural crops
Priming in row crops
Priming for postharvest disease management
Priming in the field: more variation, less efficacy?
On the longevity of priming
Direct and indirect fitness costs of priming
Perspectives: integrating priming into integrated pest management
General conclusion
References
Chapter 6. Reaching beyond crop protection: Synergism between agricultural development and malaria eradication
Abstract
Introduction: Eradication of malaria for health and economic development
The problem: Burden of malaria, the rocky road to elimination, and staring over the brink
Solutions: Steering away from the brink and getting back on track
Implementing solutions: The right approach, techniques that work, funding for effectiveness, and creative partnership
Conclusion: Agriculture can synergize malaria eradication
References
Chapter 7. Discovery and optimization of a novel insecticide, broflanilide
Abstract
Introduction
Discovery and optimization of meta-diamide
Modes of action of meta-diamide insecticides
Insecticidal activities of meta-diamides against dieldrin- and fipronil-resistant pests
Efficacy of broflanilide on 1,2-diamide-resistant diamondback moth, Plutella xylostella
Conclusion
References
Chapter 8. Studies on a novel insecticide, fluxametamide
Abstract
Introduction
Discovery and optimization
Synthesis of fluxametamide
Conclusion
References
Further reading
Chapter 9. The discovery of isocycloseram: A novel isoxazoline insecticide
Abstract
Introduction
Exploring the structure–activity relationships
Isocycloseram: The discovery journey to a modern agrochemical compound
Concluding remarks
Disclaimer
Acknowledgments
References
Chapter 10. Cyclaniliprole: A novel diamide insecticide
Abstract
Introduction
Discovery of cyclaniliprole
Structure–activity relationships
Synthesis of cyclaniliprole
Insecticidal activity
Activity against a ryanodine receptor modulator–resistant agricultural pest
Conclusion
References
Chapter 11. Optimization of mesoionic pyrido[1,2-a]pyrimidinone insecticides and discovery of 3-biaryl analogs controlling Lepidoptera species
Abstract
Introduction
Chemistry
Biology
Conclusion
References
Chapter 12. Chemistry and biology connected: the development of Inscalis
Abstract
Introduction
From a natural product to an insecticide
Product overview
Route to technical grade active ingredient, Inscalis
Summary
Acknowledgments
References
Chapter 13. Spiropidion discovery: Broad spectrum control of sucking insects and mites for multicrop utility
Abstract
Introduction
Lead generation
Optimization phase and discovery of spiropidion
Characterization and key features
Mode of action
Mode of biological activity
Biological performance
Conclusion
Acknowledgments
References
Chapter 14. Discovery of oxazosulfyl: A novel broad-spectrum insecticide
Abstract
Introduction
Discovery of oxazosulfyl: Background
Lead optimization
Biological activity of oxazosulfyl
Synthesis of oxazosulfyl
Properties of oxazosulfyl
Conclusion
Acknowledgments
References
Chapter 15. Synthesis and biological activity of a novel insecticide, benzpyrimoxan
Abstract
Introduction
Discovery of lead compound
Optimization of structures
Synthesis of benzpyrimoxan
Conclusion
Acknowledgments
References
Chapter 16. Discovery and optimization of silicon-containing complex II acaricides
Abstract
Introduction
Bioisosteric replacement of a tert-butyl-phenyl group by a trimethylsilyl-phenyl group
Discovery and biological activities of Sila-Cyflumetofen
Physicochemical properties and binding modes of Sila-Cyflumetofen
Optimization of Sila-Cyflumetofen
Conclusion
Acknowledgment
References
Chapter 17. Cycloclavine: A natural product with insecticidal potential
Abstract
Introduction
Mode of action
Biosynthesis and fermentation
Chemical synthesis
Conclusion
References
Chapter 18. Photoresponsive pesticidal agents
Abstract
Introduction
Photosensitizer as pesticides
Photo-controlled release of pesticides
Photothermal conversion reagents
Photochromic pesticides
Conclusion
References
Chapter 19. Discovery and optimization of novel mosquitocidal compounds for the control of anopheline vectors of malaria
Abstract
Introduction
Optimization of strobilurins for adult mosquito control
Biokinetic optimization
Summary
Acknowledgments
References
Chapter 20. Antiparasitic dinitrile compounds for fly control in cattle
Abstract
Dinitriles as emerging insecticide class: Initial crop protection activities at BASF
Structure–activity relationship in the benzyl–phenyl series
Mode of action studies
Antiparasitic dinitriles for fly control in cattle: First-generation lead compounds
Second-generation lead compounds
Summary
Acknowledgments
References
Chapter 21. Design, structural derivation, and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives
Abstract
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing 2-cyanoimino thiazolidine-4-one
Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing spirocyclic indoline-2-one moieties
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing thiourea and acylthiourea moieties
Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol
Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing piperazine as linker
Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives containing hydrazone as linker
Synthesis and nematicidal evaluation of 1,2,3-benzotriazin-4-one derivatives by modification of the 1,2,3-benzotriazin-4-one ring
The relationship between structure and activity of 1,2,3-benzotriazin-4-one derivatives
The synthesis and derivation route of 1,2,3-benzotriazin-4-one derivatives
Further consideration about 1,2,3-benzotriazin-4-one molecular design and derivation
Acknowledgment
References
Chapter 22. ADEPIDYN—the first N-methoxy-substituted carboxamide among the succinate dehydrogenase inhibitors
Abstract
Introduction
Discovery of ADEPIDYN
Synthesis of ADEPIDYN
Physicochemical and biokinetic properties of ADEPIDYN
Biological activity of ADEPIDYN
Conclusion
Acknowledgment
References
Chapter 23. Isoflucypram—the next-generation succinate dehydrogenase inhibitor fungicide
Abstract
Introduction
The discovery of isoflucypram
Affinity data and proposed binding mode for N-cyclopropyl-N-benzyl-carboxamides
Selection process
Physico-chemical properties and biological efficacy of isoflucypram
Summary
References
Chapter 24. Discovery and biological profile of inpyrfluxam: A new broad-spectrum succinate dehydrogenase inhibitor fungicide
Abstract
Introduction
Discovery of inpyrfluxam
Biological profile of inpyrfluxam
Application to other crops
Summary
Acknowledgments
References
Chapter 25. Isofetamid: Discovery and optimization of a novel fungicide
Abstract
Introduction
Background
Derivative synthesis and biological activity
Synthesis of isofetamid
Toxicological properties
Fungicidal activity
Conclusion
References
Chapter 26. Discovery of the trifluoromethyloxadiazoles—a new class of fungicides with a novel mode-of-action
Abstract
Introduction
Fungal histone deacetylases
Trifluoromethyloxadiazoles
Antifungal profile and structure–activity relationship of trifluoromethyloxadiazoles
Trifluoromethyl ketones
Hydroxyisoxazolines
Insights into binding mode of trifluoromethyloxadiazoles
Conclusion
References
Chapter 27. The discovery of metyltetraprole: Reconstruction of the quinone outside inhibitor extended pharmacophore to overcome QoI-resistant strains
Abstract
The discovery project concept
Discovery of metyltetraprole
Biological aspects
Conclusion
Acknowledgments
References
Chapter 28. The discovery of florylpicoxamid, a new picolinamide for disease control
Abstract
Introduction
Deconstruction of the natural product
Building the molecule
Mode of action and biological attributes
Summary
Acknowledgments
References
Chapter 29. Discovery and validation of pesticide novel target: take pyruvate kinase as an example
Abstract
Introduction
Synthesis and activity of the novel triazolothiadiazole fungicide candidate
Discovery of the target of 5o by label-free methods
Validate pyruvate kinase as a target of 5o
Conclusion
Acknowledgments
References
Chapter 30. Discovery and mode of action of cyclopyrimorate: A new paddy rice herbicide
Abstract
Introduction
Discovery of the lead compound
Optimization of the lead compound
Mode of action of cyclopyrimorate
Conclusion
Acknowledgment
References
Chapter 31. Toward a mechanistic understanding of IGPD: A potential herbicide target
Abstract
Discovery of imidazoleglycerol-phosphate dehydratase as a potential herbicide target
Structure–activity relationships of imidazoleglycerol-phosphate dehydratase inhibitors
Structural determination of imidazoleglycerol-phosphate dehydratase
Summary
Acknowledgments
References
Chapter 32. Isoxazolopyridines—a novel chemical cluster and a new (?) mode of action for dicot weed control
Abstract
Preface
Hit identification and initial activity
Hit-to-lead optimization
Greenhouse-based structure–activity relation
Mode-of-action studies
In planta biokinetics
Status quo and conclusion
References
Chapter 33. Quinazoline-2,4-dione: A promising scaffold for herbicide discovery
Abstract
Introduction
A brief overview on the medicinal and agrochemical perspectives of quinazoline-2,4-dione
Discovery process of novel 4-hydroxyphenylpyruvate dioxygenase inhibitor containing quinazoline-2,4-dione
Optimization, structure–activity relationship and crop safety
Discovery of a selective herbicide Benquitrione for sorghum in this series
The synthetic process study of Benquitrione
Conclusion
Acknowledgments
References
Chapter 34. Tirexor®—design of a new resistance breaking protoporphyrinogen IX oxidase inhibitor
Abstract
Background
Rational and design of Tirexor
Activity on protoporphyrinogen IX oxidase target enzymes
Weed spectrum and e-fate properties
Activity of Tirexor on herbicide-resistant weeds
Potential use in crops tolerant to Tirexor
Summary
References
Chapter 35. Rinskor active herbicide—A new environment-friendly tool for weed management in rice and aquatic environments
Abstract
Introduction
Discovery strategy to aim for a low risk and highly selective molecule
Biology activity—selectivity and application
Safety profile
Conclusion
Acknowledgment
References
Chapter 36. Discovery of a novel uracil herbicide by using intermediate derivatization approach
Abstract
Introduction
Discovery of novel uracil derivatives containing an isoxazoline moiety and evaluation of herbicidal activity
Synthesis/chemistry
Summary
References
Chapter 37. Herbicidal activity and application of 1-(furan-2-yl)methylphosphonates as pyruvate dehydrogenase complex inhibitor against broadleaf weeds
Abstract
Introduction
Derivatization of clacyfos
General synthesis access to 1-heterocyclylmethylphosphonates II, III, and IV
Herbicidal activity
Inhibition against pyruvate dehydrogenase complex and selectivity
Structure–activity relationships
Biological performance
Summary
Acknowledgments
References
Chapter 38. Pesticide activities evaluation of β-carboline, dihydro-β-carboline, tetrahydro-β-carboline alkaloids, and their derivatives
Abstract
Introduction
β-Carboline derivatives as anti–tobacco mosaic virus agents
Synthesis and activity of novel tetrahydro-β-carboline-3-carboxylic acid derivatives
Synthesis and activity of tryptophan derivatives
Synthesis and activity of novel spirooxindole derivatives
Synthesis and activity of hydantoin and urea derivatives
Conclusion and perspectives
Acknowledgment
References
Chapter 39. Marine natural products and plant virus control
Abstract
Introduction
Marine natural products and derivatives with antiplant virus activities
Conclusion
Acknowledgment
References
Chapter 40. Design, synthesis, and biological evaluation of strigolactone derivatives for crop enhancement applications
Abstract
Introduction
Strigolactone family
Synthesis of strigolactones
Biological activity of natural strigolactones and synthetic analogues
References
Chapter 41. Discovery and optimization of novel plant activators through structure-based virtual screening
Abstract
Introduction
SHApe-FeaTure Similarity
Conclusion
Abbreviations
Acknowledgments
References
Index

Peter Maienfisch

Peter Maienfisch is founder and owner of CreInSol MCB, honorary professor at the East China University of Science and Technology, Shanghai, China and lecturer at the University of Basel, Switzerland. Previously he held various management positions in crop protection research and development at Ciba, Novartis and Syngenta, most recently as Research Portfolio Manager Insect Control & Seedcare at Syngenta Crop Protection AG in Switzerland (until April 2020). His track record of innovation and successful introduction of new technologies includes the authorship of more than 200 scientific papers and patents, the invention of Thiamethoxam (Actara®, Cruiser®), one of the leading insecticides worldwide, and major contributions to the discovery of several new active ingredients currently in worldwide development, such as spiropidion, isocycloseram, cyclobutrifluram and a malaria vector control agent. His scientific contributions also led to numerous invitations as speaker and/or co-organizer of many international congresses, including IUPAC Crop Protection congresses.

Affiliations and expertise

Founder and owner--CreInSol MCB Honorary professor--East China University of Science and Technology Lecturer--University of Basel, Switzerland

Ir. Sven Mangelinckx

Sven Mangelinckx is co-director of the SynBioC Research Group, Ghent University, Belgium. SynBioC is broadly active in the synthesis of medicinal and crop protection compounds, isolation of natural products, modification of bioresources, green chemistry, microreactor technology and chemical biology. He obtained a PhD in chemistry in 2006 at Ghent University. Afterwards, he was a postdoctoral fellow of the Scientific Research Fund of Flanders with a research stay at the RWTH Aachen, Germany and received the Thieme Chemistry Journal Award in 2013. Since 2013, he is professor at the Department of Green Chemistry and Technology, (co-)author of 100 scientific papers, >100 conference abstracts, and (co-)promoter of 16 PhD students. He has been acting as organic chemistry section editor of Molecules, co-chairman of Bioheterocycles 2019 and national chairman of the scientific committee of topic 3 ‘Discovery and Optimization of Crop Protection Products’ of the 14th International IUPAC Congress on Crop Protection.

Affiliations and expertise

Co-Director--SynBioC Research Group Ghent University, Belgium

Life Sciences

Physical Sciences & Engineering

Social Sciences & Humanities

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