Bicyclic Sulfonimidamide Compounds for Insecticidal Activity

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Solution Overview

Problem

Current pesticidal compounds lack efficacy in controlling animal pests, particularly insects and arthropods, due to limitations in their chemical structures and stability, which affects their agricultural and horticultural applications.

Innovation Solution

Development of novel bicyclic sulfonimidamide and sulfoximine compounds with specific structural variations that enhance pesticidal activity, including variations in alkyl, halogen, and heteroaryl groups, allowing for effective control of pests by forming agrochemically acceptable salts and stereoisomers.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional pesticidal compounds are used, then agricultural applications are maintained, but pesticidal activity and control efficacy are insufficient

Engineering Contradiction:

Improvepesticidal activityVSAvoidpest control efficacy

Core Design Contradiction:

ReliabilityVSProductivity

Solution Approach 1:

The patent applies parameter changes by systematically varying chemical parameters (substituents R1-R6, heteroaryl groups, bicyclic core structures) to optimize pesticidal activity. The compounds modify molecular weight, lipophilicity, and binding affinity parameters to achieve enhanced insecticidal and arthropodicidal efficacy while maintaining stability.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining bicyclic heteroaromatic cores with various functional groups (sulfonimidamide, sulfoximine) and substituent groups. This composite approach integrates multiple functional characteristics to achieve both stability and high pesticidal activity against diverse pest species.

Inventive Principle:

Principle #40Composite materials

2Ease of manufacture

If chemical structure is simplified, then manufacturing is easier, but stability and pesticidal activity are reduced

Engineering Contradiction:

Improvesynthesis accessibilityVSAvoidchemical stability

Core Design Contradiction:

Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent employs segmentation by dividing the molecular structure into distinct functional modules: the bicyclic heteroaromatic core, the sulfonimidamide or sulfoximine group, and various substituent groups (R1-R6). This modular design allows independent optimization of each segment for stability while maintaining overall synthesizability through standardized coupling reactions.

Inventive Principle:

Principle #1Segmentation

3Adaptability or versatility

If diverse substituent groups are introduced, then pesticidal versatility is improved, but structural complexity increases

Engineering Contradiction:

Improvepest spectrum controlVSAvoidmolecular structure complexity

Core Design Contradiction:

Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent implements universality by designing a core bicyclic heteroaromatic scaffold that can accommodate multiple types of substituent groups (R1-R6). This universal core structure provides consistent pesticidal activity across diverse substituents, enabling single-compound compounds to effective control multiple pest types including insects and arthropods while managing structural complexity through systematic variation rather than completely different molecular architectures.

Inventive Principle:

Principle #6Universality (Multi-functionality)

Data Source

PatentUS20240327397A1Pesticidally Active Fused Bicyclic Heteroaromatic Compounds

Publication Date: 2024.10.03 SYNGENTA CROP PROTECITON AG

AI summary

Compounds of formula I wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides.