Fluroxypyr Meptyl Ester Formulation Using N-Alkanoyl Morpholine

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Solution Overview

Problem

High-strength formulations of fluroxypyr meptyl ester herbicides face stability issues at low temperatures and high concentrations, particularly with aromatic hydrocarbon solvents, which are also environmentally less favorable.

Innovation Solution

A high-strength emulsifiable concentrate of fluroxypyr meptyl ester is formulated using N-alkanoyl morpholine as a solvent, maintaining stability and preventing crystallization at temperatures as low as 0°C, with a composition of 340-600 g/L fluroxypyr meptyl ester, 100-200 g/L surfactant, and 300-560 g/L N-alkanoyl morpholine.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If aromatic hydrocarbon solvents are used in fluroxypyr meptyl ester formulations, then high concentration can be achieved, but low-temperature stability deteriorates and environmental profile worsens

Engineering Contradiction:
Improveconcentration of fluroxypyr meptyl esterVSAvoidlow-temperature stability
Core Design Contradiction:
Quantity of substanceVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameter of the solvent from aromatic hydrocarbon to N-alkanoyl morpholine, which fundamentally alters the formulation's low-temperature behavior. This parameter change enables high concentration (340-600 g/L fluroxypyr meptyl ester) while maintaining liquid stability at low temperatures, resolving the contradiction between concentration and low-temperature stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite solvent system using N-alkanoyl morpholine (with specific R groups of C5-C11 alkyl) combined with surfactants. This composite material approach provides synergistic effects where the morpholine solvent maintains low-temperature fluidity while the surfactant system stabilizes the high-concentration emulsifiable concentrate, preventing crystallization and maintaining homogeneity.

Inventive Principle:
Principle #40Composite materials

2Quantity of substance

If aromatic hydrocarbon solvents are used in fluroxypyr meptyl ester formulations, then high concentration can be achieved, but environmental profile deteriorates

Engineering Contradiction:
Improveconcentration of fluroxypyr meptyl esterVSAvoidenvironmental profile
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameter from aromatic hydrocarbons (which have poor environmental profiles due to toxicity and persistence) to N-alkanoyl morpholines (which have better environmental characteristics). This substitution maintains the ability to achieve high active ingredient concentration (340-600 g/L) while significantly improving the environmental safety profile of the formulation.

Inventive Principle:
Principle #35Parameter changes

3Quantity of substance

If higher concentration formulations are prepared using chlorinated solvents or 1-methyl-2-pyrrolidinone, then concentration can be increased, but environmental profile deteriorates

Engineering Contradiction:
Improveconcentration of fluroxypyr meptyl esterVSAvoidenvironmental profile
Core Design Contradiction:
Quantity of substanceVSObject-affected harmful factors

Solution Approach 1:

The patent changes the solvent parameter from environmentally problematic options (chlorinated solvents or 1-methyl-2-pyrrolidinone) to N-alkanoyl morpholines with specific structural characteristics (R = C5-C11 alkyl). This parameter change enables achieving high concentration formulations (340-600 g/L fluroxypyr meptyl ester) while providing a superior environmental profile, as morpholines are generally more environmentally benign than chlorinated solvents or pyrrolidinone.

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 formulation remains a clear, stable liquid at low temperatures, reducing packaging and environmental concerns, and is biologically equivalent to petroleum hydrocarbon solvent-based formulations, allowing for standard container use and extended storage stability.

Implementation Method 1

a low-temperature stable, high-strength emulsifiable concentrate of fluroxypyr meptyl ester can be prepared by using an N-alkanoyl morpholine solvent... the formulation remains a clear solution at temperatures below 10 °C, more preferably at temperatures 0°C

Methodology Applied
Scientific EffectCrystallization prevention: Crystallisation

Implementation Method 2

The present invention provides a high-strength herbicidal formulation comprising a mixture of a fluroxypyr meptyl ester, a surfactant or mixture of surfactants and an N-alkanoyl morpholine as a solvent... from 100 g/L to 200 g/L of surfactant

Methodology Applied
Scientific EffectSurfactant action: Surfactant

Data Source

PatentEP2154964B1High-strength, low-temperature stable herbicidal formulations of fluroxypyr meptyl ester
Publication Date: 2011.04.20 DOW AGROSCIENCES LLC
  • EP2154964B1 patent drawing
  • EP2154964B1 patent drawing
  • EP2154964B1 patent drawing

AI summary

This invention relates to a high-strength herbicidal formulation containing high concentrations of fluroxypyr meptyl ester in an N-alkanoyl morpholine solvent which exhibits significantly greater low temperature stability at high concentrations.