Oxime Ether Acetate Herbicide with Phenylpyridine Moiety
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Solution Overview
Problem
Current oxime ether acetate compounds, a type of strobilurin fungicide, have limited herbicidal activity, and there is a need for effective weed control agents that can operate at low doses with minimal toxicity.
Innovation Solution
Development of oxime ether acetate compounds containing a phenylpyridine moiety, specifically formulated to inhibit weed growth with a preparation method involving palladium catalysts and alkaline substances, which can be used as herbicides in various agricultural settings.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional oxime ether acetate compounds are used for weed control, then fungicidal activity is achieved, but herbicidal activity is limited
Solution Approach 1:
The patent modifies the chemical structure of conventional oxime ether acetate compounds by introducing phenylpyridine moieties with various substituents (R and R' groups including F, Cl, Br, CF3, NO2, OCH3, etc.). This structural parameter change transforms the compounds from having primarily fungicidal activity to exhibiting significant herbicidal activity against broadleaf weeds at low doses, while maintaining safety for crops like corn and barley.
2Reliability
If higher doses of herbicides are applied to improve weed control effectiveness, then herbicidal activity increases, but crop safety decreases
Solution Approach 1:
The patent introduces specific substituent groups (R and R') at particular positions on the phenylpyridine moiety, creating localized structural features that confer selective herbicidal activity. The substituents include electron-withdrawing groups (F, Cl, Br, CF3, NO2) and electron-donating groups (OCH3, OH, CH3), which modify the compound's interaction with weed enzymes versus crop enzymes, achieving high herbicidal activity against broadleaf weeds while maintaining safety for crops like corn and barley.
3Adaptability or versatility
If conventional strobilurin structures are used, then broad-spectrum fungicidal activity is achieved, but selective herbicidal activity is not obtained
Solution Approach 1:
The patent segments the strobilurin molecule by introducing a distinct phenylpyridine moiety as a separate functional segment with specific substituents. This segmentation allows the compound to maintain the core strobilurin structure for broad-spectrum activity while the phenylpyridine segment provides selective herbicidal properties, achieving both broad-spectrum fungicidal activity and selective herbicidal activity against broadleaf weeds.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The oxime ether acetate compounds with phenylpyridine moieties demonstrate significant herbicidal activity against broadleaf weeds at low doses, particularly effective in controlling mustard, small quinoa, and Abutilon, while showing safety for crops like corn and barley.
Implementation Method 1
Mixing a compound of formula (IV), a compound of formula (V), an alkaline substance A, a palladium catalyst and a solvent A; subjecting the mixture to a reaction at the temperature ranging from −10° C. to the reflux temperature for 0.5-20 hours to obtain a reaction solution A
Data Source
AI summary
The present invention discloses an oxime ether acetate compound containing a phenylpyridine moiety of formula (I), whose preparation method is as follows: (1) mixing a compound of formula (IV), a compound of formula (V), an alkaline substance A, a palladium catalyst and a solvent A; subjecting the mixture to a reaction at the temperature ranging from −10° C. to the reflux temperature for 0.5-20 hours to obtain a reaction solution A; post-treating the solution A to obtain a compound of formula (II); (2) mixing the compound of formula (II), an alkaline substance B, a phase transfer catalyst and a solvent B; subjecting the mixture to a reaction at the temperature ranging from −10° C. to the reflux temperature for 0.1-2 hours; then adding a compound of formula (III), continuing to react at the temperature ranging from −10° C. to the reflux temperature for 0.5-20 hours to obtain a reaction solution B; and post-treating the solution B to obtain the compound of formula (I). The oxime ether acetate compound containing a phenylpyridine moiety of formula (I) can be used for weeding in crops.