1,2,4-Triazine Carboxamides for Selective Weed Control

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Solution Overview

Problem

Existing herbicides, such as 1,2,4-triazine-3,5-dione-6-carbonylcyclohexanediones and 1,2,4-triazine-3,5-dione-6-carbonylpyrazoles, often lack sufficient herbicidal activity and compatibility with crop plants, necessitating the development of more effective compounds for selective weed control.

Innovation Solution

The use of 1,2,4-triazine-3,5-dione-6-carboxamides, specifically those with varied substituents, which exhibit enhanced herbicidal activity and selective control of weeds without harming crops, are developed, including their salts and stereoisomers, which can be applied pre-sowing, pre-emergence, or post-emergence.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If existing herbicides (1,2,4-triazine-3,5-dione-6-carbonylcyclohexanediones and 1,2,4-triazine-3,5-dione-6-carbonylpyrazoles) are used, then herbicidal activity is achieved, but the activity is insufficient and compatibility with crop plants is poor

Engineering Contradiction:
Improveherbicidal activityVSAvoidphytotoxicity to crops
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of the herbicide compound from carbonylcyclohexanedione or carbonylpyrazole groups to carboxamide groups. This structural parameter change results in compounds with enhanced herbicidal activity and improved selectivity, reducing phytotoxicity to crop plants while maintaining effectiveness against weeds.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent employs local quality by introducing specific substituent patterns at defined positions (R1, R2, R3, R4) on the 1,2,4-triazine ring system. By carefully selecting substituents at these local positions, the compound achieves differentiated behavior: high activity against target weeds while being safe for specific crop plants, thus resolving the contradiction between herbicidal power and crop compatibility.

Inventive Principle:
Principle #3Local quality

2Productivity

If broad-spectrum herbicidal activity is achieved, then control of difficult-to-control perennial weeds is improved, but selectivity with respect to crop plants may be compromised

Engineering Contradiction:
Improveweed control effectivenessVSAvoidselectivity for crop safety
Core Design Contradiction:
ProductivityVSAdaptability or versatility

Solution Approach 1:

The patent achieves both broad-spectrum weed control and crop selectivity through parameter changes in the molecular structure. The carboxamide functional group at position 6 of the 1,2,4-triazine ring, combined with specific substituent patterns, creates a compound that is effective against diverse weed species including perennials while maintaining safety for crop plants through selective metabolic pathways.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent utilizes composite material principles by combining the 1,2,4-triazine core structure with carboxamide functional groups and various substituent combinations. This composite molecular architecture integrates multiple functional elements that work together to provide both broad herbicidal spectrum and crop selectivity, resolving the contradiction between productivity and adaptability.

Inventive Principle:
Principle #40Composite materials

Data Source

PatentEP2903981B11,2,4-triazin-3,5-dion-6-carboxamide derivatives and their use as herbicides
Publication Date: 2016.05.11 BAYER CROPSCIENCE AG
  • EP2903981B1 patent drawing
  • EP2903981B1 patent drawing
  • EP2903981B1 patent drawing

AI summary

The invention describes 1,2,4-triazine-3,5-dione-6-carboxamides of general formula (I) as herbicides. In this formula (I) R1 and R2 represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q represents a tetrazolyl, triazolyl or oxadiazolyl radical. Z and Y each represent oxygen or sulphur.