Propynyl-phenyl cyclic dione herbicides for selective weed control
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Solution Overview
Problem
Current herbicidal compounds are ineffective in selectively controlling grassy monocotyledonous weeds in crops, particularly post-emergence, and lack optimal plant growth inhibition properties.
Innovation Solution
Development of novel cyclic dione compounds, specifically pyran-3,5-dione, thiopyran-3,5-dione, cyclohexane-1,3-dione, and cycloheptane-1,3-dione derivatives substituted with a phenyl group containing prop-1-ynyl or chloroethynyl at the 4-position and certain alkyl or alkoxy groups at the 2-position, which exhibit enhanced herbicidal activity and plant growth inhibition.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If conventional herbicidal compounds are used, then general herbicidal activity is achieved, but selective control of grassy monocotyledonous weeds is ineffective
Solution Approach 1:
The patent introduces specific local substitutions at defined positions on the phenyl ring (prop-1-ynyl or chloroethynyl at 4-position, specific alkyl or alkoxy at 2-position) to create localized chemical properties that confer selective toxicity to grassy monocotyledonous weeds while sparing other plants
Solution Approach 2:
The patent systematically varies chemical parameters including the type of substituent (alkyl vs alkoxy), the cyclic dione structure (pyran, thiopyran, cyclohexane, cycloheptane), and the alkyne substitution pattern to optimize selectivity and activity against target weeds
2Reliability
If existing herbicidal compounds are applied post-emergence, then some weed control is achieved, but effectiveness against grassy monocotyledonous weeds is insufficient
Solution Approach 1:
The compounds are designed to deliver a concentrated herbicidal effect specifically on grassy monocotyledonous weeds through partial action mechanisms, achieving sufficient control efficiency without requiring excessive application rates that would harm crop plants
3Reliability
If novel cyclic dione compounds with specific substitutions are developed, then herbicidal activity is enhanced, but compound complexity increases
Solution Approach 1:
The herbicidal compound is segmented into distinct functional modules: a core cyclic dione structure (pyran-3,5-dione, thiopyran-3,5-dione, cyclohexane-1,3-dione, or cycloheptane-1,3-dione), a phenyl substituent with specific positioning, and defined substituent groups at specific positions, allowing systematic optimization of each module's contribution to activity
Data Source
AI summary
The present invention relates to a compound of formula (I) wherein: R1 is C1-C3alkoxy, C1-C2alkoxy-C1-C3alkoxy, C1-C2fluoroalkoxy, ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl; R2 is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl, ethynyl, C1-C3alkoxy, C1-C3fluoroalkyl, C1-C2fluoroalkoxy, C1-C2alkoxy-C1-C3alkoxy-, or C1fluoroalkoxy-C1-C3alkoxy-; provided that when R1 is ethyl, n-propyl, n-butyl, cyclopropyl or ethynyl, then R2 is hydrogen, ethyl, n-propyl, cyclopropyl, vinyl or ethynyl; and Y is O, S, S(O), S(O)2, N(C1-C2alkyl), N(C1-C2alkoxy), C(O), CR8R9 or —CR10R11CR12R13—; and G, R3, R4, R5 and R6 are as defined herein; wherein the compound of formula (I) is optionally present as an agrochemically acceptable salt thereof. These compounds are suitable for use as herbicides. The invention therefore also relates to a method of controlling weeds, especially grassy monocotyledonous weeds, in crops of useful plants, comprising applying a compound of formula (I), or a herbicidal composition comprising such a compound, to the plants or to the locus thereof.