Malononitrile Pesticidal Compounds Modular Synthesis
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Solution Overview
Problem
Current insecticides, acaricides, and nematicides are insufficient in effectively controlling insects, acarids, and nematodes, leading to ongoing damage to crops both during growth and after harvest.
Innovation Solution
Development of new pesticidal compositions and compounds of formula I, which include a dicyanoalkane moiety and a chalcogenalkane side chain, obtained through specific synthetic processes, for use in controlling insects, acarids, and nematodes, and protecting plants from infestation.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If new compounds of formula I are developed, then pest control effectiveness is improved, but manufacturing complexity increases
Solution Approach 1:
The compound of formula I is segmented into distinct functional moieties: a dicyanoalkane portion (X-CH(R1)CH2-CN) and a chalcogenalkane side chain (R1 containing -X-Ra where X is O, S, or S(=O)n). This segmentation allows independent optimization of each fragment's properties and simplifies the synthesis route by enabling modular assembly from commercially available starting materials.
Solution Approach 2:
The patent employs intermediate compounds in the synthesis pathway, specifically using compounds of formula II and III as precursors that can be independently prepared and then combined. This intermediary approach allows for flexible route optimization and simplifies manufacturing by enabling parallel synthesis of fragments before final coupling.
2Ease of manufacture
If existing insecticides are used, then manufacturing simplicity is maintained, but pest control effectiveness deteriorates
Solution Approach 1:
The invention modifies key molecular parameters of existing pesticidal structures by introducing the specific dicyanoalkane-chalcogenalkane combination in formula I. The variables X (O, S, or S(=O)n), n (0, 1, or 2), and Ra (various alkyl groups) provide parameter space that can be optimized for enhanced biological activity while maintaining synthetic accessibility through systematic variation of these parameters.
Data Source
AI summary
Compounds of formula I wherein X is O or S(=O)n; n is 0,1 or 2; R1 is optionally substituted alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, halocycloalkyl, cycloalkenyl, halocycloalkenyl, phenyl, hetaryl, phenylalkyl, hetaryl alkyl, optionally fused to phenyl, hetaryl or heterocyclyl; A is -NRb