Pyrazole Herbicide Compounds for Selective Weed Control

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Solution Overview

Problem

Current crop protection agents for selective control of harmful plants in crops have limitations such as low herbicidal activity, narrow spectrum of control, low selectivity, toxicological concerns, and economic production challenges due to difficult precursor availability and chemical instability, as well as environmental dependency.

Innovation Solution

Development and use of herbicidal and plant growth regulator compounds of the formula (I), which include specific heteroaryl-4-[(hetero)arylcarbonyl]pyrazole compounds that can form salts with inorganic or organic acids, offering enhanced activity, selectivity, and stability across various environmental conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional herbicides are used for selective control of harmful plants, then some herbicidal activity is achieved, but the activity is insufficient against particular harmful plants and the spectrum of control is narrow

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

Solution Approach 1:

The patent modifies the chemical structure of pyrazole compounds by changing parameters such as substituting different heteroaryl groups at positions 1 and 4 of the pyrazole ring, varying the carbonyl group substitutions, and adjusting R groups to optimize both herbicidal activity against specific weeds and broad-spectrum control capability

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite herbicidal compounds combining pyrazole core structure with multiple heteroaryl substituents (such as pyridyl, pyrimidinyl, triazinyl groups) and carbonyl derivatives, resulting in a composite molecular structure that achieves both high activity against particular harmful plants and broad spectrum control

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional herbicides are applied for weed control, then some control effect is achieved, but selectivity in crops of useful plants is too low and toxicological profile is unfavorable

Engineering Contradiction:
Improveweed control effectVSAvoidselectivity and toxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces specific heteroaryl substituents (such as 3-pyridinyl, 2-pyrimidinyl, 4-triazinyl groups) at specific positions of the pyrazole ring, creating local chemical characteristics that enable selective interaction with weed plant targets while sparing crop plants, thereby improving selectivity

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The invention adjusts molecular parameters including the type of heteroatoms (N, O, S) in the heteroaryl groups, the position of substitution on the pyrazole ring, and the nature of carbonyl substituents to modify the compound's biological profile, achieving favorable toxicological characteristics while maintaining weed control efficacy

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If alternative active compounds are developed for broader weed control, then spectrum of control is improved, but chemical stability is insufficient and environmental dependency increases

Engineering Contradiction:
Improvespectrum of controlVSAvoidchemical stability
Core Design Contradiction:
Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

The patent creates chemically stable composite molecules by combining the pyrazole core with robust heteroaryl groups (pyridyl, pyrimidinyl, triazinyl) and carbonyl derivatives, forming a stable molecular framework that maintains structural integrity under various environmental conditions while providing broad weed control spectrum

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention designs pyrazole derivatives with multiple functional groups that can interact with various weed plant targets through different mechanisms, enabling the single compound to provide broad-spectrum control across diverse weed species while maintaining chemical stability

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

4Ease of manufacture

If economically viable herbicides are produced, then production cost is reduced, but precursor availability becomes difficult and manufacturing complexity increases

Engineering Contradiction:
Improveproduction economyVSAvoidmanufacturing complexity
Core Design Contradiction:
Ease of manufactureVSDevice complexity

Solution Approach 1:

The patent structures the pyrazole herbicidal compounds with modular segments including the pyrazole ring, heteroaryl substituents, and carbonyl groups, which can be synthesized separately and then assembled, simplifying the manufacturing process and improving production economy

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The invention employs common pyrazole synthesis pathways and universally applicable heteroaryl building blocks that can be used to produce multiple different herbicidal compounds through a single platform process, reducing manufacturing complexity and improving economic viability

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

Data Source

PatentUS8252723B2Substituted 1-(3-pyridinyl)pyrazol-4-ylacetic acids, processes for their preparation and their use as herbicides and plant growth regulators
Publication Date: 2012.08.28 BAYER CROPSCIENCE AG
  • US8252723B2 patent drawing
  • US8252723B2 patent drawing
  • US8252723B2 patent drawing

AI summary

The invention relates to the use of compounds of the formula (I) or salts thereofin whichR1, R2, R3, R4, R5, R6 and n are as defined in claim 1 as herbicides and plant growth regulators.The invention also relates to novel compounds of the formula (I) and salts thereof (see claim 5).