Acyl Morpholine Solvent Systems for Pesticide Solubility

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Solution Overview

Problem

Current solvent systems for agricultural actives, such as N-methyl pyrrolidone, pose issues due to reproductive toxicity and limited solubility for certain biocides like Imidacloprid, leading to precipitation problems during dilution in aqueous media.

Innovation Solution

A solvent system comprising N-formyl morpholine and propylene carbonate, with a weight ratio of 70:30 to 90:10, is used to create a formulation that maintains high solubility and minimizes precipitation when mixed with an aqueous medium.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If N-methyl pyrrolidone (NMP) is used as a solvent for agricultural actives, then high solubility of the active is achieved, but the formulation becomes harmful due to reproductive toxicity

Engineering Contradiction:
Improvesolubility of agricultural activeVSAvoidreproductive toxicity
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent replaces the toxic NMP solvent with alternative solvents (water, alcohols, esters, ketones, carboxylic acids) that are less harmful and can be used in formulations. This substitution eliminates the reproductive toxicity issue while maintaining the solubility function, effectively replacing a harmful substance with safer alternatives that achieve the same technical purpose.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent changes the chemical parameters of the solvent system by transitioning from NMP to a combination of alternative solvents with different chemical properties. This parameter change includes using solvents with varying polarities, molecular weights, and solubility characteristics to achieve high solubility of agricultural actives without the toxic effects of NMP.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If dialkylamides containing hydroxysubstituted acyl radical are used as solvents, then reproductive toxicity is reduced, but solubility of certain biocides like Imidacloprid becomes insufficient leading to precipitation

Engineering Contradiction:
Improvereproductive toxicityVSAvoidsolubility of biocides
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent employs composite solvent systems combining multiple solvents (water, alcohols, esters, ketones, carboxylic acids) in specific ratios to achieve synergistic effects. This composite approach allows the formulation to maintain high solubility for biocides like Imidacloprid while avoiding the precipitation issues that occur with single-component solvents such as dialkylamides. The combination of solvents with complementary properties resolves the solubility deficiency.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent develops a universal solvent system that can effectively dissolve multiple different types of agricultural actives (biocides, plant growth regulators, etc.) using a combination of solvent types. This multi-functional solvent system replaces the need for specialized solvents for each active ingredient, providing broad compatibility and high solubility across different chemical classes without causing precipitation.

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

3Ease of operation

If soluble liquid concentrate is diluted in aqueous medium, then the formulation becomes ready-to-use, but precipitation of the agricultural active occurs due to high local concentration

Engineering Contradiction:
Improvedilution and ready-to-use formulationVSAvoidprecipitation during dilution
Core Design Contradiction:
Ease of operationVSStability of the object's composition

Solution Approach 1:

The patent performs preliminary action by pre-mixing the agricultural active with the optimized solvent system at the concentration stage before dilution. This preliminary dissolution in the specific solvent combination ensures complete solubility and prevents precipitation during subsequent dilution with water. The pre-formed stable solution maintains homogeneity even when diluted to ready-to-use concentrations.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses the optimized solvent system as an intermediary medium between the concentrated agricultural active and the final aqueous formulation. This intermediary solvent system facilitates smooth transition during dilution by maintaining solubility throughout the concentration gradient, preventing the formation of precipitates that would otherwise occur during direct dilution of water-insoluble actives.

Inventive Principle:
Principle #24Intermediary (Mediator)

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

This solvent system effectively dissolves pesticides and plant growth regulators, reducing precipitation and ensuring a clear, homogeneous formulation, even at high concentrations, thus addressing the limitations of existing systems.

Implementation Method 1

A solvent system comprising N-formyl morpholine and propylene carbonate, with a weight ratio of 70:30 to 90:10, is used to create a formulation that maintains high solubility

Methodology Applied
Scientific EffectSolvation: Solvation

Implementation Method 2

minimizes precipitation when mixed with an aqueous medium

Methodology Applied
Scientific EffectMiscibility:

Data Source

PatentEP2575446B1Agricultural formulations with acyl morpholines and polar aprotic co-solvents
Publication Date: 2016.04.20 AKZO NOBEL CHEMICALS INTERNATIONAL BV
  • EP2575446B1 patent drawing
  • EP2575446B1 patent drawing
  • EP2575446B1 patent drawing

AI summary

The present invention provides a formulation comprising a pesticide and/or a plant growth regulator; an acyl morpholine of the formula (I) where R is H, CH3 or C2H5; and a polar aprotic co-solvent different from an acyl morpholine of formula (I). The formulation can be used in treatment of plants, and is especially well suited for use as a soluble liquid formulation.