Bis-amide Insecticides with Arylperfluoroalkyl Substitutions

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Solution Overview

Problem

Current insecticides lack improved efficacy, selectivity, reduced toxicity, and resistance against a broader range of pests, with a need for more efficient delivery and biodegradability.

Innovation Solution

Development of bis-amide derivatives substituted with an arylperfluoroalkyl group and a 4-pyridyl or 1-oxidopyridin-1-ium-4-yl group, which exhibit enhanced insecticidal properties, including greater efficacy at lower application rates and improved selectivity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional insecticides are used, then pest control is achieved, but efficacy is insufficient and resistance develops

Engineering Contradiction:
Improveinsecticidal efficacyVSAvoidpest resistance
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of amide derivatives through specific substitutions (arylperfluoroalkyl groups at positions 3 or 5, and 4-pyridyl or 1-oxidopyridin-1-ium-4-yl groups at positions 2 or 6). These structural parameter changes result in compounds with enhanced insecticidal activity and improved ability to overcome pest resistance compared to conventional insecticides.

Inventive Principle:
Principle #35Parameter changes

2Reliability

If insecticide application rate is increased, then pest control efficacy is improved, but toxicity increases and environmental harm worsens

Engineering Contradiction:
Improvepest control efficacyVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent achieves higher efficacy at lower application rates through specific molecular parameter changes. The bis-amide derivatives with arylperfluoroalkyl and pyridyl substitutions demonstrate improved insecticidal potency, allowing reduced dosages while maintaining or enhancing pest control effectiveness, thereby reducing toxicity and environmental harm.

Inventive Principle:
Principle #35Parameter changes

3Duration of action of stationary object

If insecticide persistence is increased, then protection duration is extended, but biodegradability decreases and environmental accumulation increases

Engineering Contradiction:
Improveprotection durationVSAvoidbiodegradability
Core Design Contradiction:
Duration of action of stationary objectVSLoss of substance

Solution Approach 1:

The patent optimizes the balance between persistence and biodegradability through controlled parameter changes in the molecular structure. The specific substitution pattern (arylperfluoroalkyl at 3 or 5 position, pyridyl/oxidopyridin-1-ium at 2 or 6 position) provides adequate protection duration while maintaining improved biodegradability compared to conventional persistent insecticides.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2981523B1Insecticidal compounds
Publication Date: 2021.05.19 SYNGENTA PARTICIPATIONS AG
  • EP2981523B1 patent drawing
  • EP2981523B1 patent drawing
  • EP2981523B1 patent drawing

AI summary

The present invention relates to novel triazole derivatives of formula (I) having insecticidal activity, to processes and intermediates for preparing them, to insecticidal, acaricidal, nematicidal or molluscicidal compositions comprising them and to methods of using them to combat and control insect, acarine, nematode or mollusc pests wherein R1, R2, G1, G2, Q1 and Q2 are as defined in claim 1; or salts thereof.