Cinnoline Derivatives for Selective Weed Control

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Solution Overview

Problem

Current herbicidal agents lack effective selectivity and efficacy in controlling weeds without harming useful crops, and there is a need for compounds with improved herbicidal activity and selectivity.

Innovation Solution

Development of cinnoline derivatives with specific structural features, such as Formula (I), which are used in agrochemical compositions to control weeds by applying them to a locus, providing a herbicidally effective amount to selectively target and control unwanted plants while being tolerant to certain crop plants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If current herbicidal agents are used, then weed control is achieved, but selectivity and efficacy are insufficient causing harm to useful crops

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

Solution Approach 1:

The patent introduces specific local structural features at defined positions on the cinnoline core (R2 at position 5, R3 at position 3, R1 at position 1) to create differential interaction with weed versus crop plant targets. This local differentiation of molecular properties enables selective herbicidal action where the compound exerts strong effect on weeds while being tolerated by useful crops.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent systematically varies multiple molecular parameters including substituent types (halogen, alkyl, alkoxy, cyano), substituent positions, and molecular size to optimize the balance between herbicidal activity and crop safety. By changing these chemical parameters, the compound achieves enhanced efficacy against weeds while maintaining tolerance in useful plants.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If herbicidal activity is increased, then weed control effectiveness improves, but selectivity between weeds and crops deteriorates

Engineering Contradiction:
Improveweed control effectivenessVSAvoidselectivity between weeds and crops
Core Design Contradiction:
ProductivityVSAdaptability or versatility

Solution Approach 1:

The patent employs local quality by introducing specific functional groups at strategic positions on the cinnoline ring system. The R2 group (S(O)nC1-C6alkyl or similar) at position 5 and the R3 group at position 3 create localized chemical characteristics that enhance binding affinity to weed plant targets while being recognized as non-threatening by crop plant defense mechanisms, thus achieving both high productivity and adaptability.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates a composite molecular structure combining the cinnoline core with diverse substituent groups (R1, R2, R3, R4, R5, R6) that work synergistically. This composite structure integrates multiple functional elements that collectively provide both potent herbicidal activity and crop selectivity, with each substituent contributing specific properties that enhance overall performance.

Inventive Principle:
Principle #40Composite materials

Data Source

PatentUS20230250066A1Herbicidal cinnoline derivatives
Publication Date: 2023.08.10 SYNGENTA CROP PROTECITON AG
  • US20230250066A1 patent drawing
  • US20230250066A1 patent drawing
  • US20230250066A1 patent drawing

AI summary

Compounds of the formula (I), wherein the substituents are as defined in claim 1. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.