Novel Spinosyn Compounds with Improved Water Solubility
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Solution Overview
Problem
Current spinosyn compounds face challenges with poor water solubility, which complicates formulation development and may have negative environmental impacts, and there is a need for novel members of the spinosyn family with improved solubility and insecticidal activity to address resistance in target pests and concerns about aquatic life.
Innovation Solution
Development of novel spinosyn compounds with improved solubility and insecticidal activity, specifically designed to enhance formulation development and efficacy in agricultural applications, including specific structural modifications such as variations in the general formula (I) that provide better UV stability and enhanced biological activity.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Quantity of substance
If conventional spinosyn compounds are used, then insecticidal activity is achieved, but water solubility remains poor
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure of spinosyn compounds through semi-synthetic derivatization. Specifically, modifications are made at the C-8 hydroxyl group and C-21 side chain positions to alter solubility parameters while preserving the core macrolide structure responsible for insecticidal activity. This allows improvement of water solubility without complete loss of biological efficacy.
Solution Approach 2:
The patent creates composite structures by combining the spinosyn macrolide core with various sugar moieties and side chain modifications. These composite molecular structures integrate hydrophilic and hydrophobic regions, enabling improved water solubility while maintaining the lipophilic interactions necessary for binding to nicotinic acetylcholine receptors in pests.
2Quantity of substance
If surfactants and organic solvents are added to improve solubility, then water solubility increases, but environmental impact and formulation complexity increase
Solution Approach 1:
The patent extracts and eliminates the need for harmful auxiliary substances by incorporating solubility-enhancing features directly into the spinosyn molecular structure. Through semi-synthetic modification, the active compound itself becomes more water-soluble, removing the requirement for separate surfactants and organic solvents that would otherwise be needed to achieve adequate solubility.
Solution Approach 2:
The modified spinosyn compounds perform self-service by inherently providing their own solubility enhancement through structural modifications. The molecules contain built-in hydrophilic groups and modified side chains that enable them to dissolve in water without requiring external surfactants or solvents, thereby reducing environmental impact and formulation complexity.
3Quantity of substance
If quaternary ammonium salts are prepared to improve solubility, then water solubility increases, but biological activity changes towards anti-protozoan and anti-viral activities
Solution Approach 1:
The patent applies local quality by making targeted modifications at specific positions of the spinosyn molecule rather than comprehensive structural changes. The semi-synthetic derivatization focuses on the C-8 hydroxyl group and C-21 side chain, locally altering properties to improve solubility while preserving the essential pharmacophore regions that confer insecticidal specificity and avoid transformation into compounds with anti-protozoan or anti-viral activities.
4Ease of manufacture
If novel spinosyn derivatives are developed to improve solubility, then formulation development is simplified, but manufacturing complexity may increase
Solution Approach 1:
The patent applies preliminary action by pre-modifying the spinosyn structure during the compound development phase to incorporate solubility-enhancing features. This preliminary structural optimization is performed before formulation development, so that subsequent formulation work can proceed with compounds that already possess improved solubility characteristics, thereby simplifying downstream formulation processes despite the additional initial synthetic steps.
Data Source
AI summary
The present invention generally relates to the field of pesticides. More specifically, the present invention relates to novel spinosyn compounds having advantageous properties, processes for their preparation, and their use as pesticides.