C5-Substituted 1,4-Cineole Herbicides for Crop-Selective Weed Control

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Solution Overview

Problem

There is a need for a selective herbicide that can effectively kill weeds without causing phytotoxicity to crops and minimize environmental pollution and economic costs, as existing 1,4-cineole derivatives lack a substituent at the C5 position of the 1,4-cineole ring.

Innovation Solution

A 1,4-cineole derivative represented by specific general formulas with various substituents, including alkyl, haloalkyl, alkenyl, cycloalkyl, and heterocyclic groups, exhibits excellent herbicidal activity, and a synthetic intermediate is used to produce these derivatives.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing 1,4-cineole derivatives are used, then herbicidal activity is achieved, but selectivity against crops is insufficient causing phytotoxicity

Engineering Contradiction:

Improveherbicidal activityVSAvoidphytotoxicity to crops

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent introduces a substituent at the specific C5 position of the 1,4-cineole ring structure. This local structural modification at a specific position enhances herbicidal selectivity by improving the compound's ability to differentiate between weed and crop biological targets, thereby reducing phytotoxicity to crops while maintaining herbicidal activity.

Inventive Principle:

Principle #3Local quality

Solution Approach 2:

The patent modifies the chemical structure parameters of 1,4-cineole derivatives by introducing specific substituents (such as alkyl, haloalkyl, alkenyl, cycloalkyl, or heterocyclic groups) at the C5 position. This structural parameter change optimizes the compound's interaction with biological targets, achieving both high herbicidal activity and improved crop safety.

Inventive Principle:

Principle #35Parameter changes

2Reliability

If higher dosage of herbicide is applied, then herbicidal effect is enhanced, but environmental pollution and economic costs increase

Engineering Contradiction:

Improveherbicidal effectVSAvoidenvironmental pollution and economic costs

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent optimizes the herbicidal efficiency by modifying the molecular structure of 1,4-cineole derivatives. The introduced substituent at C5 position enhances the compound's biological activity, allowing effective weed control at lower dosages. This reduces both environmental pollution from chemical application and economic costs associated with herbicide purchase and application.

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentEP4707280A11,4-cineole derivative and intermediate thereof, herbicide containing said derivative as active ingredient, method for using herbicide, and method for preparing agrochemical composition

Publication Date: 2026.03.11 HOKKO CHEM IND CO LTD

AI summary

The present invention provides a 1,4-cineole derivative represented by the following general formula (1), (1'), (2), (2'), (3) or (3') which exhibit an excellent herbicidal activity, an intermediate thereof, and a herbicide containing the derivative as an active ingredient. In the general formulae (1), (1'), (2), (2'), (3) and (3'), R1 to R3, X and W each represent a predetermined substituent as described in the specification: