Avermectin Derivatives Substituted at 4'- and 4''-Positions
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Solution Overview
Problem
Current macrolide compounds for pest control, particularly against insects and Acarina, have unsatisfactory biological properties, necessitating the development of new compounds with improved pesticidal properties.
Innovation Solution
Development of derivatives of Avermectin compounds, specifically mixtures of Avermectin B1a and B1b with varying substituents and monosaccharides, which can form salts and tautomers, offering enhanced pesticidal activity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If current macrolide compounds are used for pest control, then pest control function is provided, but biological properties are unsatisfactory
Solution Approach 1:
The patent applies parameter changes by systematically modifying the chemical structure of macrolide compounds through substitution at the 4'- and 4''-positions with various groups (R1, R2, R3, R4, R5). These structural parameter changes result in compounds with improved biological properties and enhanced pesticidal activity against insects and Acarina while maintaining acceptable safety profiles
Solution Approach 2:
The invention creates composite molecular structures by combining the avermectin core with additional substituent groups at specific positions. These composite structures (formula I compounds) integrate multiple functional elements that work together to achieve both high pesticidal efficacy and improved biological properties including selectivity and reduced toxicity
2Adaptability or versatility
If broad-spectrum pesticidal activity is achieved, then control of resistant pest stages is improved, but selectivity among organisms may be reduced
Solution Approach 1:
The patent applies local quality by introducing specific substituent groups at particular positions (4'- and 4''-positions) of the macrolide molecule. These localized structural modifications create compounds that maintain broad-spectrum activity against insects and Acarina while exhibiting selective toxicity - being effective against pests but showing excellent tolerance by warm-blooded animals, fish, and plants
Data Source
AI summary
Described is a compound of the formula (I) wherein the bond between carbon atoms 22 and 23 is a single or double bond; m is 0 or 1; R1, is C1-C12alkyl, C3-C8cycloalkyl or C2-C12alkenyl; and either (A) R2 is —N(R3)R4, and (1) X is 0, wherein R3 is, for instance, hydrogen, unsubstituted or mono- to pentasubstituted C1-C12alkyl, and R4 is, for instance, mono- to pentasubstituted C1-C12alkyl, unsubstituted or mono- to pentasubstituted C3-C12cycloalkyl; or (2) X is S, wherein R3 is, for instance, hydrogen, unsubstituted or mono- to pentasubstituted C1-C12alkyl, and R4 is, for instance, hydrogen, unsubstituted or mono- to pentasubstituted C1-C12alkyl; or (3) X is 0 or S, wherein R3 and R4 together are, for instance, a three- to seven membered alkylene or a four- to seven-membered alkenylene bridge; or (B) R2 is OR5, X is 0 or S, wherein R5 is, for instance, C1-C12alkyl, mono- to pentasubstituted C1-C12alkyl; or, if appropriate, an E/Z isomer, E/Z isomer mixture and/or tautomer thereof, in each case in free form or in salt form; such a compound demonstrates pesticidal activity.