Substituted Pyrrolone Derivatives for Selective Weed Control

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Solution Overview

Problem

Current herbicidal pyrrolones lack alternative compounds with improved potency, spectrum of activity, and selectivity compared to existing herbicides.

Innovation Solution

Development of novel substituted pyrrolone derivatives with specific functional groups and structures that enhance herbicidal activity, including compounds of the formula (I) with varied substituents, which can be used in herbicidal compositions and methods for controlling weeds.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing herbicidal pyrrolones are used, then herbicidal activity is achieved, but potency and spectrum of activity are insufficient

Engineering Contradiction:
Improveherbicidal activityVSAvoidspectrum of activity
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by systematically varying substituents at multiple positions (R1-R6, R8-R10) on the pyrrolone core structure, including different halogens, alkyl groups, alkoxy groups, and heterocyclic rings, to optimize herbicidal activity and broaden spectrum of activity across different weed species

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining the pyrrolone core with various heterocyclic rings (isoxazole, triazole, pyrimidine) and diverse substituent groups, resulting in hybrid compounds that exhibit enhanced and broadened herbicidal activity compared to simpler analogs

Inventive Principle:
Principle #40Composite materials

2Reliability

If existing herbicidal pyrrolones are used, then herbicidal function is provided, but selectivity is insufficient

Engineering Contradiction:
Improveherbicidal functionVSAvoidselectivity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by introducing specific substituent patterns at particular positions on the pyrrolone ring system, such as halogen atoms at R1-R2 positions and specific heterocyclic groups at R3-R6 positions, to enhance selectivity for weed species while preserving herbicidal function and reducing impact on desirable crops

Inventive Principle:
Principle #3Local quality

3Reliability

If novel substituted pyrrolone derivatives are developed, then potency and spectrum of activity are improved, but compound complexity increases

Engineering Contradiction:
ImprovepotencyVSAvoidcompound complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent applies segmentation by dividing the herbicidal agent into a modular structure consisting of a pyrrolone core with distinct substituent regions (R1-R6, R8-R10), allowing systematic optimization of individual positions to enhance potency while maintaining a manageable structural framework for synthesis and characterization

Inventive Principle:
Principle #1Segmentation

Data Source

PatentUS9936701B2Herbicidal compounds
Publication Date: 2018.04.10 SYNGENTA CROP PROTECITON AG
  • US9936701B2 patent drawing
  • US9936701B2 patent drawing
  • US9936701B2 patent drawing

AI summary

The invention relates to pyrrolone compounds of the formula (I) wherein X, Rb, Rc, R1, R2 and R3 are as defined in the specification. Furthermore, the present invention relates to processes and intermediates for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control plant growth.