Thiophene Carboxamide Derivatives for Low-Dose Pathogen Control

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Solution Overview

Problem

Existing microbicidal compounds for crop protection face challenges in spectrum of action, safety profile, selectivity, application rate, residue formation, and resistance development, particularly against pathogens like Xanthomonas campestris pv. campestris.

Innovation Solution

Development of substituted thiophene carboxamide derivatives with specific structural features, including various substituents, which are effective against phytopathogenic microorganisms, including Xanthomonas campestris pv. campestris, and can be used in compositions for agricultural applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing microbicidal compounds are used for crop protection, then basic protection is provided, but efficacy against Xanthomonas campestris pv. campestris is insufficient at low doses

Engineering Contradiction:
Improveefficacy against phytopathogenic microorganismsVSAvoidapplication rate
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of microbicidal compounds through specific substitutions on the thiophene ring (R1, R2, R3 positions) and amide group (R6, R7, R8 positions). These structural parameter changes result in compounds with enhanced biological activity, allowing effective control of Xanthomonas campestris pv. campestris at lower application rates compared to existing compounds.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining a thiophene core with specific substituent groups (halogens, alkyls, alkoxy groups, amino groups) and amide functionalities. This composite approach generates molecules with optimized properties that simultaneously improve efficacy against target pathogens and reduce required application rates.

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing microbicidal compounds are applied to control fungal and bacterial diseases, then some disease control is achieved, but resistance development occurs

Engineering Contradiction:
Improvedisease control effectivenessVSAvoidresistance development
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent introduces structural parameter changes with multiple substitution patterns on the thiophene ring and varied amide group configurations. This diversity in molecular structure creates compounds with novel modes of action, making it more difficult for pathogens to develop resistance compared to existing compounds with limited structural variation.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If existing microbicidal compounds are used, then basic protection is provided, but safety profile and selectivity require improvement

Engineering Contradiction:
Improveprotection effectivenessVSAvoidsafety profile and selectivity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by introducing specific substituent groups at particular positions on the thiophene ring (R1, R2, R3) and amide group (R6, R7, R8). These localized structural modifications enhance the compound's ability to selectively target phytopathogenic microorganisms while minimizing impact on non-target organisms, thereby improving safety profile and selectivity.

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS12492196B2Thienyloxazolones and analogues
Publication Date: 2025.12.09 BAYER AG
  • US12492196B2 patent drawing
  • US12492196B2 patent drawing
  • US12492196B2 patent drawing

AI summary

The present disclosure relates to substituted thiophene carboxamides derivatives, their use for controlling phytopathogenic microorganisms and compositions comprising thereof.