Ether Compounds with Nitrogen Heterocycles for Dual Insecticidal and Fungicidal Activity

Resolve Bottlenecks,
Find Innovative Solutions
Generate Solutions

Solution Overview

Problem

Current insecticides and fungicides often damage crops and have adverse effects on mammals and other living organisms, and there is a lack of compounds with fungicidal activity among dihalopropene compounds, necessitating the development of novel ether compounds with nitrogen-containing 5-member heterocycles for effective crop protection.

Innovation Solution

Development of ether compounds with a specific nitrogen-containing 5-member heterocycle structure, which exhibit both insecticidal and fungicidal activity at low doses, capable of controlling a wide range of pests and diseases in agriculture and other fields without harming beneficial organisms.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional insecticides and fungicides are used to control pests and diseases, then insecticidal and fungicidal activity is achieved, but crop damage and harmful effects on mammals and beneficial organisms occur

Engineering Contradiction:
Improveinsecticidal and fungicidal activityVSAvoidcrop damage and toxicity to mammals and beneficial organisms
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical structure by introducing specific substituent patterns (halo groups at positions 3 and 4, various R1-R8 groups) on the pyridine ring and heterocyclic moieties to optimize the balance between biological activity and safety profile. This structural parameter optimization enables effective pest and disease control while reducing phytotoxicity and mammalian toxicity.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention combines multiple functional groups (pyridine ring, heterocyclic structures including triazole, oxadiazole, thiadiazole, furan, or pyrrole rings, ether linkages) into a composite molecular structure that achieves both insecticidal and fungicidal activities simultaneously, while the specific substitution patterns reduce harmful effects on non-target organisms.

Inventive Principle:
Principle #40Composite materials

2Reliability

If dihalopropene compounds are used for insect control, then insecticidal activity is achieved, but fungicidal activity is not demonstrated and novel compounds are still needed

Engineering Contradiction:
Improveinsecticidal activityVSAvoidfungicidal activity and broad-spectrum effectiveness
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent designs compounds with dual insecticidal and fungicidal activities by incorporating specific heterocyclic structures (triazole, oxadiazole, thiadiazole, furan, or pyrrole rings) combined with pyridine cores. This multi-functional molecular design allows a single compound to effectively control both insect pests and fungal diseases, expanding the versatility beyond single-mode dihalopropene compounds.

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

3Productivity

If existing insecticides are used to protect crops, then pest control is achieved, but phytotoxicity and deleterious effects on living organisms occur

Engineering Contradiction:
Improvecrop protection effectivenessVSAvoidphytotoxicity and adverse effects on living organisms
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent applies local quality by introducing specific substituent patterns at defined positions on the molecular structure. Halogen atoms are placed at positions 3 and 4 of the pyridine ring, while various R groups (alkyl, alkoxy, haloalkyl, aryl, heteroaryl) are positioned at R1-R8 locations to create localized functional zones that enhance target specificity and reduce off-target effects on crops and beneficial organisms.

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS8222280B2Ether compounds with nitrogen-containing 5-member heterocycle and uses thereof
Publication Date: 2012.07.17 SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
  • US8222280B2 patent drawing
  • US8222280B2 patent drawing
  • US8222280B2 patent drawing

AI summary

The invention relates to ether compounds with nitrogen-containing 5-member heterocycle, represented by formula (I):The groups are as defined as specification.The compounds of the present invention have broad-spectrum insecticidal activities, and they are very effective to lepidopterous pests, including Ostrinia nubilalis, sugarcane borer, summer fruit tortrix moth, Grapholitha inopinata, Lymantria dispar, Cnaphalocrocis medialis, Pyrausta nubilalis, Heliothis assulta, Grapholitha molesta, Plutella xylostella, Laphygma exigua, Prodenialitura and the like, especially more effective to Plutella xylostella and Laphygma exigua, and can have very good effects at very low doses. And the compounds of present invention have high activities to homopteran pests such as aphid. At the same time, some compounds of present invention have very good fungicidal activities, and can be used for preventing wheat powdery mildew, cucumber downy mildew, vegetable grey mould and the like.