Mesoionic Compound Pesticide Resistance
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Solution Overview
Problem
Existing mesoionic pyrimidinium compounds do not exhibit sufficient controlling effects against various harmful organisms and are prone to resistance, necessitating a novel active ingredient with a different chemical structure and action mechanism.
Innovation Solution
A modified mesoionic compound with a cyanoethyl group, represented by a specific formula, is developed, which includes various substituents such as phenyl and pyridyl groups with specific halogen and alkyl substitutions, offering enhanced controlling activity against harmful organisms.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional mesoionic pyrimidinium compounds are used as insecticides, then they provide basic insecticidal activity, but they do not exhibit sufficient controlling effect and harmful organisms easily acquire resistance
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure of conventional mesoionic pyrimidinium compounds through specific substitutions: introducing a cyanoethyl group at the 1-position, adding hydroxy and oxo groups at positions 2 and 4, and incorporating specific phenyl or pyridyl groups with halogen and alkyl substitutions. These structural parameter changes create novel compounds with improved controlling effects and reduced resistance acquisition by harmful organisms.
2Reliability
If the chemical structure of conventional mesoionic compounds is modified, then controlling activity against harmful organisms is improved, but structural complexity increases
Solution Approach 1:
The patent applies segmentation by dividing the molecular structure into distinct functional segments: a core pyrimidinium ring system, a cyanoethyl substituent at position 1, hydroxy and oxo groups at positions 2 and 4, and aromatic phenyl or pyridyl groups with specific substitutions. This segmented approach allows systematic optimization of each segment's contribution to biological activity while managing overall molecular complexity.
Solution Approach 2:
The patent applies local quality by introducing specific functional groups at predetermined positions on the molecular structure. Each position (1-position cyanoethyl, 2-position hydroxy, 4-position oxo, and substituted phenyl/pyridyl at position 3) has locally optimized properties that collectively enhance controlling activity. The local substitutions with halogen atoms and alkyl groups on the aromatic rings further refine the activity profile without requiring complete structural redesign.
Data Source
AI summary
The purpose of the present invention is to provide a mesoionic compound or a salt thereof that exhibits excellent control activity against various pests. Provided is a mesoionic compound represented by formula (1). (In the formula, Ra represents a hydrogen atom or a methyl group, R1 represents a phenyl group or pyridyl group which is optionally substituted with up to two substituents selected independently from R2, and R2 represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, a c-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, a t-butyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a methyloxy group, an ethyloxy group, an n-propyloxy group, an i-propyloxy group, a c-propyloxy group, an n-butyloxy group, an i-butyloxy group, a s-butyloxy group, a t-butyloxy group, an n-pentyloxy group, a trifluoromethyloxy group, a 2,2,2-trifluoroethyloxy group, a methylthio group, a methylsulfoxy group, a methylsulfonyl group, a vinyl group, an ethynyl group, etc.)