Pyrazolyl Acrylonitrile Compounds for Insecticidal Activity

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Solution Overview

Problem

Current insecticides and acaricides face resistance issues over time, and there is a need for cost-effective and environmentally friendly compounds with improved insecticidal and acaricidal activity to address growing agricultural and environmental demands.

Innovation Solution

Development of novel pyrazolyl acrylonitrile compounds with specific structural modifications, including various substituents and stereoisomers, which exhibit high insecticidal and acaricidal activity against a range of pests, and their formulation into compositions for agricultural and public health use.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing insecticides and acaricides are used continuously, then pest control is maintained, but pest resistance develops over time

Engineering Contradiction:
Improveinsecticidal activityVSAvoidpest resistance
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent modifies the chemical structure of pyrazolyl acrylonitrile compounds by changing parameters such as substituting R1 with various functional groups (carboxyl, carbonyl, alkoxy carbonyl, cycloalkyl carbonyl), changing R2 from H to methyl or other groups, and modifying R3 substituents. These structural parameter changes create novel compounds with improved insecticidal activity and reduced pest resistance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite molecular structures by combining the pyrazolyl acrylonitrile core with various substituent groups (carboxyl, carbonyl, alkoxy carbonyl, cycloalkyl carbonyl, and different R2 and R3 groups). This composite approach generates diverse compounds with enhanced biological activity and reduced resistance.

Inventive Principle:
Principle #40Composite materials

2Reliability

If new compounds are developed to overcome resistance, then insecticidal activity is improved, but development cost and complexity increase

Engineering Contradiction:
Improveinsecticidal activityVSAvoidcompound structure complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent segments the molecular structure into distinct components: the pyrazolyl acrylonitrile core and various substituent groups (R1, R2, R3). This segmentation allows systematic modification of individual parts to optimize insecticidal activity while controlling overall structural complexity.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent applies local quality by modifying specific positions in the molecular structure (R1, R2, R3 groups) with different functional groups to achieve optimal biological activity. Each substituent position is optimized independently to balance activity and complexity.

Inventive Principle:
Principle #3Local quality

3Reliability

If conventional compounds are used, then current control is maintained, but environmental friendliness and cost-effectiveness are reduced

Engineering Contradiction:
Improveacaricidal activityVSAvoidenvironmental impact
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes chemical parameters by introducing environmentally friendly substituent groups (carboxyl, carbonyl, alkoxy carbonyl, cycloalkyl carbonyl) that may improve biodegradability and reduce environmental harm while maintaining acaricidal activity.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP2426110B1Pyrazolyl acrylonitrile compounds and uses thereof
Publication Date: 2013.10.16 SINOCHEM CORP
  • EP2426110B1 patent drawingFigure 1~2
  • EP2426110B1 patent drawingFigure 3~4
  • EP2426110B1 patent drawingFigure 5~6

AI summary

A kind of pyrazolyl acrylniitrile compounds represented by the structures of formula I or stereoisomers thereof are disclosed in the present invention. Where in: R1 is selected from the group of substituents consisting of H, C1-C4 alkoxy C1-C2 alkyl, C3-C5 alkenyloxy C1-C2 alkyl, C3-C5 alknyloxy C1-C2 alkyl, C1-C4 alkylthio C1-C2 alkyl, C1-C5 alkyl carbonyl, C3-C8 cycloalkyl carbonyl, C1-C5 alkoxy carbonyl or C1-C5 alkylthio carbonyl; R2 is Cl or methyl; R3 is H, methyl, CN, NO2 or halogen. Or its stereoisomers. The Formula I compounds have high insecticidal activities or acaricidal activities, so they can be used as insecticide or acaricide.