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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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N-Hetaryl-[2(1H)-pyridinyliden]cyanamides: A New Class of Systemic Insecticides
Peter Jeschke1, Peter Lösel2, Elke Hellwege2
1Research & Development, Pest Control Chemistry, Bayer AG, Crop Science, Building 6550, Alfred-Nobel-Straße 50, D-40789 Monheim am Rhein, Germany.
Journal of Agricultural and Food Chemistry
|June 24, 2022
Summary
New N-hetaryl-[2(1H)-pyridinylidene]cyanamides show excellent aphicidal activity and a favorable risk profile for pollinators. These novel insecticides offer broad-spectrum control and potential for structural optimization.
Area of Science:
- Agricultural Chemistry
- Insecticide Development
- Organic Chemistry
Background:
- Inspired by existing insecticides like Shell and flupyrimin, this study explores novel chemical structures.
- Focuses on "shortened structures" by omitting the methylene link, creating N-hetaryl-[2(1H)-pyridinylidene]cyanamides.
Purpose of the Study:
- To synthesize and evaluate the insecticidal activity of the new N-hetaryl-[2(1H)-pyridinylidene]cyanamide chemical class.
- To assess their potential as xylem systemic insecticides with improved safety profiles.
Main Methods:
- Scaffold hopping and structure simplification for designing new compounds.
- Synthesis of N-hetaryl-[2(1H)-pyridinylidene]cyanamides on a technical scale.
- Molecular modeling studies (Fukui functions, dipole moments, electrostatic potentials) to understand binding and guide optimization.
Main Results:
- The compounds act as full nicotinic acetylcholine receptor (nAChR) agonists with low orthosteric binding affinity.
- Demonstrated excellent aphicidal activity in vegetables and cotton via various application methods, especially seed dressing.
- Showed good plant compatibility and a better risk profile for bee pollinators compared to existing nAChR modulators.
- Field trials indicated potential against cereal grain aphids, corn rootworm, and wireworm.
Conclusions:
- N-hetaryl-[2(1H)-pyridinylidene]cyanamides represent a promising new class of insecticides.
- Their physicochemical properties and biological activity support their use in crop protection, particularly as seed treatments.
- Further structural optimization holds potential for developing novel bicyclic insecticides with enhanced efficacy and safety.
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