Pyrazine Compounds for Broad-Spectrum Insect Control
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Solution Overview
Problem
There is a need for highly effective and versatile agents that can control a wide range of invertebrate pests, particularly difficult-to-control pests such as insects, with a broad activity spectrum.
Innovation Solution
The development of pyrazine compounds, including their stereoisomers, salts, and N-oxides, which are synthesized using palladium complexes and nucleophilic reagents in the presence of carbon monoxide, and can be further modified through condensation reactions and alkylations to enhance pesticidal activity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If existing pesticides are used to control invertebrate pests, then some pest control is achieved, but the activity spectrum is narrow and effectiveness against difficult-to-control insects is insufficient
Solution Approach 1:
The patent modifies the chemical structure of pyrazine compounds by changing parameters such as substituting hydrogen atoms at positions 3 and/or 5 with halogen atoms (fluorine, chlorine, bromine), cyano groups, or other functional groups. These structural parameter changes result in compounds with enhanced pesticidal activity and broader spectrum effectiveness against difficult-to-control insects while maintaining safety profiles.
2Reliability
If pyrazine compounds are synthesized using palladium complexes and nucleophilic reagents, then the desired pesticidal compounds are produced, but the synthesis process becomes more complex
Solution Approach 1:
The synthesis process is divided into discrete steps: (1) forming the pyrazine core structure using palladium-catalyzed coupling of halogenated pyridine derivatives with nucleophilic reagents, (2) introducing functional groups at positions 3 and/or 5 through subsequent reactions, and (3) optimizing the compound properties. This segmentation allows each step to be optimized independently while maintaining overall reliability of the pesticidal activity.
Solution Approach 2:
The patent employs palladium complexes as intermediary catalysts to facilitate the formation of the pyrazine core structure from halogenated pyridine derivatives and nucleophilic reagents. This intermediary approach enables the construction of complex pesticidal compounds through reliable, controllable reactions while managing synthesis complexity through established catalytic methodology.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
These compounds demonstrate good pesticidal activity against a variety of invertebrate pests, including difficult-to-control insects, offering a broad spectrum of control and versatility in application.
Implementation Method 1
The compounds of formula I can be prepared from the corresponding compounds II by a carbonylation reaction, using 0.01 to 0.2 equivalents of a palladium complex, such as palladium diacetate, bis(benzonitrile)dichloropalladium, bis(dibenzylideneacetone)palladium, or tris(dibenzylideneacetone)dipalladium, and 0.01 to 0.2 equivalents of a ligand, such as triphenylphosphine, 1,1-bis(diphenylphosphino)ferrocene, or 1,3-bis(diphenylphosphino)propane, as catalysts
Data Source
AI summary
The invention relates to compounds of formula II wherein the variables have the meanings as defined in the specification, to compositions com-prising them, to active compound combinations comprising them, and to their use for protecting growing plants and animals from attack or infestation by invertebrate pests, furthermore, to seed comprising such compounds.