Diazene Oxide Carboxylates for Mite Control

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Solution Overview

Problem

Current pesticidal compounds are not effective in controlling mites and other acarids, and there is a need for novel diazene oxide carboxylate compounds with improved miticidal activity.

Innovation Solution

Development of diazene oxide carboxylate compounds with specific structural formulas, including branched or straight-chain alkyl, haloalkyl, or cycloalkyl groups, and their use in compositions with suitable carriers for application as acaricides, insecticides, and nematicides, prepared by reacting substituted compounds with oxidizing agents like meta-chloroperbenzoic acid.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional pesticidal compounds are used, then general pest control is achieved, but miticidal activity is insufficient

Engineering Contradiction:
Improvemiticidal activityVSAvoidspectral control
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of diazene oxide carboxylates through varying substituents (R1, R2, R3, R4, R5, R6) at different positions on the aromatic ring. This structural parameter modification enables the compounds to achieve both high miticidal activity and broad spectral control against various pests including mites, insects, and nematodes

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite pesticidal compounds by combining the diazene oxide carboxylate core structure with multiple different substituent groups. These composite molecular structures provide both the specificity needed for miticidal activity and the versatility for broad-spectrum pest control

Inventive Principle:
Principle #40Composite materials

2Reliability

If novel diazene oxide carboxylate compounds are developed, then miticidal efficacy is improved, but compound complexity increases

Engineering Contradiction:
Improveacaricidal efficacyVSAvoidmolecular structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent systematically varies substituent parameters (types, positions, and combinations of R1-R6 groups) to optimize acaricidal efficacy. By making controlled parameter changes to the molecular structure, the patent achieves high efficacy against mites while managing structural complexity through a systematic approach to substitution patterns

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 diazene oxide carboxylate compounds demonstrate high efficacy as acaricides, achieving 100% control of mite adults and eggs/larvae, providing a novel solution for mitigating mite infestations on plants.

Implementation Method 1

prepared by reacting substituted compounds with oxidizing agents like meta-chloroperbenzoic acid

Methodology Applied
Scientific EffectOxidation: Oxidation

Data Source

PatentEP2146955B1Pesticidal diazene oxide carboxylates
Publication Date: 2010.12.29 CHEMTURA CORP
  • EP2146955B1 patent drawing
  • EP2146955B1 patent drawing
  • EP2146955B1 patent drawing

AI summary

Pesticidal compounds having the structural formula (I) wherein: R2 is C1-C6 branched or straight chain alkyl; C1-C4 branched or straight-chain haloalkyl; or C3-C6 cycloalkyl; m is 0, 1, or 2; X is selected from the group consisting of: C1-C6 branched or straight-chain alkoxy; halogen; Ci-Cc, branched or straight-chain alkyl; or Ci-G, branched or straight-chain alkylthio; n is 0 or 1; A is 0; CH2; or NR', wherein R' is (C1-C6 alkyl )carbonyl; Y is phenyl; benzyl; thia/.olyl; thienyl; pyridyl; or tetrahydrofuranyl, the aromatic ring of each substituent being optionally substituted with one or more of halogen, C1-C6 branched or straight-chain alkyl, or C1-C6 branched or straight-chain haloalkyl; use of the compounds as pesticides and pesticidal compositions comprising the compounds.