Diamide Derivatives for Controlling Resistant Insects

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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 compounds, requiring alternative insecticides that do not exhibit cross-resistance with the diamide class.

Innovation Solution

The use of certain diamide derivatives, specifically compounds of formula I, which are applied to insects or plants to control diamide-resistant insects, offering improved control over these resistant pests by targeting specific biochemical mechanisms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If diamide insecticides are used to control pests, then initial pest control effectiveness is high, but pest resistance develops over time reducing control efficacy

Engineering Contradiction:
Improvepest control effectivenessVSAvoidduration of resistance-free control
Core Design Contradiction:
ReliabilityVSDuration of action of moving object

Solution Approach 1:

The patent modifies the chemical structure of diamide compounds by changing parameters such as substituting hydrogen atoms with halogen atoms (chlorine, fluorine, bromine) at specific positions on the aromatic ring, and varying the alkyl chain length and substitution patterns. These parameter changes create novel diamide derivatives that maintain high affinity for the ryanodine receptor while overcoming resistance mechanisms developed against conventional diamides.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention combines the core diamide structural motif with various composite substituent groups including halogenated aromatic rings, alkoxy chains, and cyanophenyl groups. This creates composite molecular structures that integrate multiple functional elements to achieve both high insecticidal activity and resistance-breaking capability against diamide-resistant pest populations.

Inventive Principle:
Principle #40Composite materials

2Reliability

If higher doses of diamide insecticides are applied to overcome resistance, then pest control effectiveness may be maintained, but environmental and safety risks increase

Engineering Contradiction:
Improvepest control effectivenessVSAvoidenvironmental and safety risks
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

By optimizing the molecular parameters of diamide derivatives, the patent achieves compounds with enhanced binding affinity and selectivity for the pest ryanodine receptor. This allows effective pest control at lower application doses, thereby reducing environmental load and safety risks associated with high-dose insecticide applications.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If alternative insecticides without cross-resistance are sought, then control of diamide-resistant pests is improved, but availability and suitability of alternatives is limited

Engineering Contradiction:
Improvecontrol of diamide-resistant pestsVSAvoidavailability of alternative insecticides
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent develops a series of diamide derivatives that universally target the ryanodine receptor pathway, which is conserved across multiple pest species including Lepidoptera, Coleoptera, and Diptera. This multi-functional approach provides a versatile solution applicable to various diamide-resistant pest populations while maintaining the proven mode of action of diamides.

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

Solution Approach 2:

By systematically varying structural parameters within the diamide class, the invention generates multiple compounds with different physicochemical properties and resistance-breaking profiles, expanding the availability of suitable alternatives for controlling diamide-resistant pests across different crop and pest scenarios.

Inventive Principle:
Principle #35Parameter changes

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 damage caused by diamide-resistant insects on plants, providing improved control compared to secondary amide analogs, with enhanced efficacy in controlling resistant strains, particularly those with target site resistance.

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: Chemical Bonding

Data Source

PatentUS20240308988A1Method For Controlling Diamide Resistant Pests and Compounds Therefor
Publication Date: 2024.09.19 SYNGENTA CROP PROTECITON AG
  • US20240308988A1 patent drawing
  • US20240308988A1 patent drawing
  • US20240308988A1 patent drawing

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 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.