Oxopyrazine Derivative Herbicide Structure for Crop Safety

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Solution Overview

Problem

Current 1,3-cyclohexanedione derivatives used as herbicides require high doses for effective weed control and can cause damage to useful plants, necessitating the development of a compound with enhanced herbicidal activity at lower doses and improved safety for crops.

Innovation Solution

A cyclohexanedione compound with a pyrazine ring substituted with an oxo or thioxo group, specifically an oxopyrazine derivative, which acts as a herbicide, effectively controlling weeds in various fields and showing high safety for useful plants and crops at lower doses.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If high doses of current 1,3-cyclohexanedione derivatives are used for weed control, then herbicidal activity is achieved, but damage to useful plants occurs

Engineering Contradiction:
Improveherbicidal activityVSAvoiddamage to useful plants
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of 1,3-cyclohexanedione derivatives through specific substitutions: introducing a pyrazine ring with oxo or thioxo groups at the 2-position, and adding specific substituents (R1-R13) with defined chemical properties. These structural parameter changes result in compounds that maintain herbicidal activity while reducing phytotoxicity, allowing effective weed control at lower doses without damaging useful plants

Inventive Principle:
Principle #35Parameter changes

2Reliability

If high doses of herbicides are applied for effective weed control, then weed control efficacy is improved, but the dosage requirement increases

Engineering Contradiction:
Improveweed control efficacyVSAvoiddosage
Core Design Contradiction:
ReliabilityVSQuantity of substance

Solution Approach 1:

The patent achieves improved weed control efficacy at reduced dosages through parameter changes in the molecular structure. The specific chemical modifications (pyrazine ring with oxo/thioxo groups, defined substituents R1-R13) enhance the herbicidal activity per unit mass, allowing effective weed control with lower quantities of the active compound compared to conventional 1,3-cyclohexanedione derivatives

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentUS8648075B2Substituted pyrido[2,3-b]pyrazines and an agrochemical composition thereof
Publication Date: 2014.02.11 KUMIAI CHEM IND CO LTD
  • US8648075B2 patent drawing
  • US8648075B2 patent drawing
  • US8648075B2 patent drawing

AI summary

The present invention is to provide an oxopyrazine derivative having an excellent herbicidal activity and besides exhibiting high safety for useful crops and the like, or a salt thereof, and a herbicide containing the same.The present invention relates to an oxopyrazine derivative represented by formula [I]:wherein X1 represents an oxygen atom or a sulfur atom; X2 represents CH or N(O)m; m represents an integer of 0 or 1; R1 represents a hydrogen atom, a C1-C12 alkyl group and the like; R2 represents a halogen atom, a cyano group and the like; R3 is a hydroxyl group, a halogen atom and the like; A1 represents C(R4R5); A2 represents C(R6R7) or C═O; A3 represents C(R8R9); R4 to R9 represent a hydrogen atom or an alkyl group,or a salt thereof, and a herbicide containing these compounds.