Bicyclic Diamide Derivatives for Resistant Pest Control

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Solution Overview

Problem

The increasing resistance of insects to diamide insecticides poses a significant threat to crop cultivation, as diamide-resistant pests become less susceptible to existing bisamide compounds, requiring alternative insecticides that do not exhibit cross-resistance with the diamide class.

Innovation Solution

The use of certain bicyclic diamide derivatives, specifically compounds of formula I, which are applied to insects or plants to control diamide-resistant pests by targeting the ryanodine receptor and reducing damage, while offering improved control over resistant species like Plutella xylostella and Spodoptera frugiperda.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If diamide insecticides are used to control pests, then pest control efficacy is improved, but resistance development in pest populations increases

Engineering Contradiction:

Improvepest control efficacyVSAvoidresistance development

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent introduces chemically modified diamide compounds with altered molecular structures (formula I derivatives) that maintain insecticidal activity against ryanodine receptors while overcoming resistance mechanisms. The structural modifications include varying substituents at specific positions of the diamide core structure, changing physical-chemical parameters to evade metabolic resistance while preserving target site binding affinity.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention employs composite molecular structures combining the diamide pharmacophore with diverse heterocyclic and aromatic substituents. These composite structures create multiple interaction points with the ryanodine receptor, reducing the impact of single-point mutations that cause resistance in simpler diamide structures.

Inventive Principle:

Principle #40Composite materials

2Reliability

If higher doses of diamide insecticides are applied to overcome resistance, then pest control effectiveness is maintained, but harmful effects on non-target organisms increase

Engineering Contradiction:

Improvepest control effectivenessVSAvoidharmful effects on non-target organisms

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces specific substituent patterns at localized positions of the diamide molecule (e.g., R1, R3, R4 groups in formula I) that enhance selectivity for insect ryanodine receptors. These local structural modifications improve binding affinity for insect targets while reducing off-target effects on mammals and beneficial organisms, allowing effective pest control at lower application rates.

Inventive Principle:

Principle #3Local quality

3Adaptability or versatility

If existing diamide compounds are used, then cross-resistance is avoided initially, but resistance mechanisms develop over time reducing susceptibility

Engineering Contradiction:

Improvecross-resistance avoidanceVSAvoidsusceptibility control

Core Design Contradiction:

Adaptability or versatilityVSReliability

Solution Approach 1:

The patent segments the diamide molecule into distinct functional regions: the core diamide pharmacophore that binds the ryanodine receptor, and variable substituent regions (aromatic rings, heterocyclic groups, alkyl chains) that modulate metabolic stability and receptor affinity. This segmentation allows optimization of each region independently to overcome specific resistance mechanisms while maintaining overall insecticidal activity.

Inventive Principle:

Principle #1Segmentation

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 effectively reduce pest damage on plants by targeting diamide-resistant insects, providing improved control compared to secondary amide analogs, with enhanced efficacy even at lower application rates, thus mitigating the resistance issues faced with existing diamide insecticides.

Implementation Method 1

Diamide insecticides target the ryanodine receptor in insects and lead to a depletion of the intracellular calcium reservoirs

Methodology Applied

Scientific EffectRyanodine receptor binding:

Data Source

PatentUS20240251795A1Method for controlling diamide resistant pests & compounds therefor

Publication Date: 2024.08.01 SYNGENTA CROP PROTECITON AG

AI summary

A method for combating and controlling diamide-resistant insects to (i) reduce damage on a plant, which comprises applying to the insect, to a locus of the insect, or to a plant susceptible to attack by the insect an, effective amount of a compound of formula I; or (ii) protect plant propagation material, which comprises treating the propagation material or the site, where the propagation material is planted, with an effective amount of a compound of formula I; wherein the compound of formula I is (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.