Substituted Bicyclic Compounds for Resistant Invertebrate Pest Control

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Solution Overview

Problem

There is a need for new compounds with high pesticidal activity and a broad spectrum of activity against invertebrate pests, such as insects, arachnids, and nematodes, due to the development of resistance to existing agents and the difficulty in controlling these pests effectively.

Innovation Solution

Substituted bicyclic compounds of formula I, including their stereoisomers, salts, tautomers, and N-oxides, are developed, which exhibit high pesticidal activity and a broad activity spectrum against invertebrate pests.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing pesticidal agents are used, then initial pest control effectiveness is achieved, but pest resistance develops over time reducing efficacy

Engineering Contradiction:
Improvepesticidal activityVSAvoidlong-term effectiveness
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of pesticidal compounds through specific substitution patterns on the bicyclic core (varying R1-R6, Ar, and heteroatom configurations). This creates novel molecular parameters that differ from existing pesticides, enabling the compounds to interact with pest targets in new ways that bypass developed resistance mechanisms while maintaining high pesticidal activity.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If existing pesticidal agents are used, then some pest species are controlled, but broad spectrum activity against diverse invertebrate pests is insufficient

Engineering Contradiction:
Improveactivity spectrumVSAvoidcontrol effectiveness
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent achieves universality through the design of a versatile bicyclic core structure (compounds of formula I) that can be systematically modified with various substituents to target multiple pest types. The core structure provides a platform for multi-functionality, allowing single compounds or combinations to effectively control diverse invertebrate pests including insects, arachnids, and nematodes through different modes of action.

Inventive Principle:
Principle #6Universality (Multi-functionality)

3Reliability

If new pesticidal compounds are developed, then activity against resistant pests improves, but complexity of compound structure increases

Engineering Contradiction:
Improveefficacy against resistant pestsVSAvoidmolecular complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the pesticidal compound into a standardized bicyclic core structure (the invariant framework) and variable substituent groups (R1-R6, Ar). This segmentation allows the core to provide consistent baseline activity while substituents are optimized for specific pest targets, reducing overall molecular complexity compared to entirely novel structures while maintaining efficacy against resistant pests.

Inventive Principle:
Principle #1Segmentation

Data Source

PatentEP3601231B1Pesticidal compounds
Publication Date: 2023.05.10 BASF SE
  • EP3601231B1 patent drawing
  • EP3601231B1 patent drawing
  • EP3601231B1 patent drawing

AI summary

The present invention relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined according to the description, (I). The compounds of formula (I), as well as the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof, are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.