Amide Solvents Prevent Agrochemical Crystallization

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Solution Overview

Problem

Existing organic solvents fail to completely prevent crystallization of water-insoluble agricultural active ingredients during dilution, especially at low temperatures, leading to clogged spraying nozzles and uneven distribution in agricultural applications.

Innovation Solution

The use of specific amides, such as N-methyl-N-(2-propylheptyl)-formamide and N-methyl-N-(2-propylheptyl)-acetamide, as solvents for water-insoluble organic agrochemical active ingredients, which significantly reduce the crystallization tendency and maintain solubility even at low temperatures.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If conventional organic solvents are used to dissolve water-insoluble agricultural active ingredients, then the agricultural actives can be dissolved at high concentrations, but crystallization occurs upon dilution especially at low temperatures

Engineering Contradiction:
Improveconcentration of agricultural activeVSAvoidcrystallization tendency
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the amide solvent - specifically using N-methyl-N-substituted amides with particular alkyl groups (such as N-methyl-N-(2-propylheptyl)amide) that have optimized solvating properties. This structural parameter change enables the solvent to maintain high agricultural active concentration while preventing crystallization upon dilution, even at low temperatures, thereby resolving the contradiction between concentration and stability.

Inventive Principle:
Principle #35Parameter changes

2Ease of operation

If emulsifiable concentrates are diluted with water for field application, then the formulation becomes suitable for spraying, but the agricultural actives crystallize and clog spraying nozzles

Engineering Contradiction:
ImprovesprayabilityVSAvoidnozzle clogging
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent uses the N-methyl-N-substituted amide as an intermediary substance that mediates between the water-insoluble agricultural active and the aqueous spray medium. This amide solvent acts as a bridge, maintaining the agricultural active in dissolved state during dilution and preventing crystallization that would otherwise clog nozzles, thus ensuring reliable spray operation while maintaining ease of application.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If long-chain dialkyl amides are used as solvents to prevent crystallization, then crystallization is inhibited to some degree, but crystallization still occurs at low temperatures

Engineering Contradiction:
Improvecrystallization inhibitionVSAvoidlow temperature performance
Core Design Contradiction:
Stability of the object's compositionVSTemperature

Solution Approach 1:

The patent applies local quality by specifically designing the amide molecule with particular local structural features - the N-methyl-N-substituted structure with specific alkyl groups (such as 2-propylheptyl) that provide enhanced solvating capability at the molecular level. This localized structural optimization enables the solvent to maintain effectiveness at low temperatures where conventional long-chain dialkyl amides fail, preventing crystallization across a broader temperature range.

Inventive Principle:
Principle #3Local quality

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

These amides effectively dissolve high concentrations of water-insoluble agrochemicals, preventing crystallization at temperatures below room temperature, allowing for stable emulsions and efficient application even in cold conditions, reducing the need for large storage and handling of concentrated formulations.

Implementation Method 1

certain amides as further defined herein can advantageously be used as solvents for water-insoluble organic agrochemically active ingredients

Methodology Applied
Scientific EffectSolvation: Solvation

Data Source

PatentEP2519498B1Amides, use of amides as solvents for organic compounds, compositions and emulsions containing amides, and method for treating a plant
Publication Date: 2014.08.13 AKZO NOBEL CHEMICALS INTERNATIONAL BV
  • EP2519498B1 patent drawing
  • EP2519498B1 patent drawing
  • EP2519498B1 patent drawing

AI summary

The present invention relates in general to the use of amides of the following general formula (I) wherein R1 is a linear or branched hydrocarbyl group containing 9 to 14 carbon atoms; R2 is selected from the group consisting of methyl, ethyl and benzyl; and R3 is selected from the group consisting of hydrogen, methyl and ethyl, as solvents for organic agriculturally active ingredients, compositions comprising organic agriculturally active ingredients and such amides, methods for treating a plant utilizing such compositions, as well as some of the amides as such and methods for their production.