Benzamide Herbicide Compounds with Enhanced Selectivity

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Solution Overview

Problem

Current benzamide compounds used as herbicides often exhibit insufficient herbicidal activity at low application rates and unsatisfactory selectivity, leading to compatibility issues with crop plants and higher toxicity to humans and animals.

Innovation Solution

Development of specific benzamide compounds of formula I, their N-oxides, and agriculturally suitable salts, which offer strong herbicidal activity, low toxicity, and high compatibility with crop plants, with a broad spectrum of activity against unwanted vegetation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional benzamide compounds are used as herbicides, then herbicidal activity is achieved, but the activity is insufficient at low application rates and selectivity is unsatisfactory

Engineering Contradiction:
Improveherbicidal activityVSAvoidtoxicity to humans and animals
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent applies parameter changes by systematically modifying the chemical structure of benzamide compounds through varying substituents at different positions (R1, R2, R3, R4, R5, R6 groups) to optimize herbicidal activity while reducing toxicity. This involves changing molecular weight, lipophilicity, and electronic properties to achieve better selectivity and efficacy at lower application rates.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates composite molecular structures by combining the benzamide core with various heterocyclic groups (oxadiazole, triazole, tetrazole) and different substituent patterns. These composite structures achieve synergistic effects that enhance herbicidal activity while improving safety profiles through reduced non-selective toxicity.

Inventive Principle:
Principle #40Composite materials

2Reliability

If conventional benzamide compounds are used as herbicides, then herbicidal activity is achieved, but selectivity is unsatisfactory resulting in low compatibility with crop plants

Engineering Contradiction:
Improveherbicidal activityVSAvoidcompatibility with crop plants
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies local quality by introducing specific substituent patterns at particular positions on the benzamide molecule (e.g., electron-withdrawing groups at R2, specific heterocycles at R5) that create localized chemical properties enhancing selectivity. These local modifications allow the compound to differentiate between target weed enzymes and crop plant enzymes, improving compatibility with crops while maintaining herbicidal efficacy.

Inventive Principle:
Principle #3Local quality

3Reliability

If application rate is increased to improve herbicidal activity, then control effectiveness improves, but toxicity to humans and animals increases

Engineering Contradiction:
Improveherbicidal activityVSAvoidtoxicity
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent enables achieving high herbicidal activity at low application rates through parameter changes in molecular structure. The optimized compounds have enhanced binding affinity to target enzymes (ACCase or ALS) due to improved molecular recognition, allowing effective weed control at lower doses and thereby reducing toxicity risks to humans and animals.

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP3390372B1Benzamide compounds and their use as herbicides
Publication Date: 2020.06.03 BASF SE
  • EP3390372B1 patent drawing
  • EP3390372B1 patent drawing
  • EP3390372B1 patent drawing

AI summary

The invention relates to a compound of formula (I), an N-oxide or an agriculturally suitable salt thereof, wherein the variables are as defined in the specification, and their use as herbicides.