Herbicidal Complex Stabilization via Amine Buffer Mediation

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Solution Overview

Problem

Fenoxaprop ester herbicides degrade rapidly when mixed with certain other herbicides, such as pyrasulfotole and bromoxynil, leading to a reduction in the shelf life of herbicidal compositions, which is undesirable for agricultural applications.

Innovation Solution

A novel chemical complex is developed, comprising an acid-sensitive herbicide like fenoxaprop p-ethyl, a weak acid herbicide like pyrasulfotole, an ester herbicide like bromoxynil, an optional safener like mefenpyr diethyl, and a cation donating agent, stabilized by a buffer system capable of forming complexes and hydrogen bonding, such as triethanolamine, to prevent degradation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If fenoxaprop ester herbicide is mixed with weak acid herbicides (pyrasulfotole, bromoxynil), then the herbicidal composition can control a wider variety of weeds, but the fenoxaprop ester degrades more rapidly reducing shelf life

Engineering Contradiction:
Improveweed control rangeVSAvoidshelf life
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

A buffer system comprising an amine-containing compound capable of forming a complex acts as an intermediary between the fenoxaprop ester herbicide and weak acid herbicides. The buffer prevents direct harmful interactions while allowing both herbicides to function, thereby maintaining shelf life despite mixing with multiple herbicide types for broader weed control.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The buffer system changes the pH parameter of the herbicidal composition by accepting protons from weak acid herbicides. This pH modulation prevents acid-catalyzed degradation of fenoxaprop ester while maintaining conditions suitable for herbicidal activity, thus preserving shelf life during extended storage.

Inventive Principle:
Principle #35Parameter changes

2Duration of action of moving object

If fenoxaprop ester herbicide is mixed with weak acid herbicides, then pre- and post-emergent control can be achieved, but acid-catalyzed hydrolysis and transesterification increase degradation rate

Engineering Contradiction:
Improveoperative control timeVSAvoidchemical stability
Core Design Contradiction:
Duration of action of moving objectVSStability of the object's composition

Solution Approach 1:

The amine-containing buffer serves as a mediator that intercepts protons from weak acid herbicides before they can catalyze hydrolysis or transesterification of fenoxaprop ester. This allows the herbicidal mixture to maintain chemical stability while providing extended operative control from pre- to post-emergent stages.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The buffer system performs preliminary anti-action by neutralizing weak acids before they can initiate degradation reactions. By preemptively accepting protons, the buffer prevents acid-catalyzed hydrolysis and transesterification, thereby maintaining chemical stability throughout the extended operative period.

Inventive Principle:
Principle #9Preliminary anti-action

3Reliability

If buffer system is added to stabilize fenoxaprop ester, then shelf life is extended, but composition complexity increases

Engineering Contradiction:
Improveshelf lifeVSAvoidcomposition complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The amine-containing buffer compound performs multiple functions simultaneously: it acts as a pH buffer to neutralize weak acids, forms complexes to stabilize fenoxaprop ester, and may serve as a solubility enhancer. This multi-functionality extends shelf life while minimizing the need for additional separate stabilizing agents, thus limiting composition complexity.

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

4Reliability

If amine-containing buffer capable of hydrogen bonding is used, then stabilization is enhanced, but manufacturing cost and synthesis complexity increase

Engineering Contradiction:
Improvestabilization effectivenessVSAvoidmanufacturing simplicity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The invention changes the chemical parameter of the buffer by selecting compounds with specific pKa values and hydrogen-bonding capabilities. This parameter optimization enhances stabilization effectiveness through stronger complex formation and hydrogen bonding, while the selected compounds remain commercially available and manufacturable through standard chemical processes.

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

The complex stabilizes the herbicidal composition, preventing acid-catalyzed hydrolysis and transesterification, thereby extending the shelf life and maintaining the effectiveness of the herbicides, even in the presence of acidic conditions.

Implementation Method 1

a buffer system capable of forming complexes and hydrogen bonding, such as triethanolamine

Methodology Applied
Scientific EffectHydrogen bonding:

Implementation Method 2

an amine-containing compound capable of forming a complex

Methodology Applied
Scientific EffectComplex formation:

Implementation Method 3

preventing acid-catalyzed hydrolysis

Methodology Applied
Scientific EffectHydrolysis prevention: Hydrolysis

Implementation Method 4

preventing acid-catalyzed hydrolysis and transesterification

Methodology Applied
Scientific EffectTransesterification prevention:

Data Source

PatentUS8642508B2Complex for use in stabilizing herbicidal compositions and methods for synthesizing and using
Publication Date: 2014.02.04 BAYER CROPSCIENCE AG
  • US8642508B2 patent drawing
  • US8642508B2 patent drawing
  • US8642508B2 patent drawing

AI summary

The present invention is directed to the discovery, isolation, identification and methods of synthesis of a novel chemical complex that can be used to stabilize mixtures of different chemical compounds, and in particular mixtures of different herbicidal compounds.