Cyano and Double-Bond Pyrethroid Compounds for Higher Vapor Pressure
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Solution Overview
Problem
Existing pyrethroid insecticides face issues with resistance from mosquitoes and poor vapor pressure, limiting their effectiveness in mosquito-repellent incense applications.
Innovation Solution
A pyrethroid compound with a cyano group and a double bond, synthesized through specific chemical reactions, enhancing vapor pressure and efficacy against household pests like mosquitoes and flies.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If pyrethroid compounds with nitrogen-containing structures are used, then contact-killing effect is improved, but vapor pressure decreases making it difficult to volatize for mosquito-repellent incense
Solution Approach 1:
The invention extracts the nitrogen-containing structure from the pyrethroid compound to improve vapor pressure. By removing the nitrogen atom from the cyclopropane ring structure, the compound can more easily volatilize for mosquito-repellent incense applications while maintaining insecticidal activity through the retained cyano group and double bond structures.
Solution Approach 2:
The invention changes the chemical structure parameters by replacing the nitrogen-containing structure with a carbon-based structure containing a cyano group and double bond. This structural parameter change increases vapor pressure while maintaining the desired biological activity against insects.
2Object-affected harmful factors
If existing pyrethroid products are used, then insecticidal activity is achieved, but mosquitoes develop resistance reducing effectiveness
Solution Approach 1:
The invention creates a composite molecular structure combining a cyclopropane ring with a cyano group and double bond in a specific configuration. This composite structure provides novel insecticidal activity that overcomes resistance developed to conventional pyrethroids, while the fluorinated benzyl group enhances stability and biological activity.
3Temperature
If pyrethroid compounds are simplified structurally, then vapor pressure increases for incense application, but insecticidal activity may be reduced
Solution Approach 1:
The invention applies local quality by strategically placing functional groups (cyano group, double bond, fluorinated benzyl group) at specific positions on the cyclopropane ring. This localized arrangement ensures that vapor pressure is improved through structural simplification while insecticidal activity is maintained through the preserved spatial configuration of key functional groups.
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 compound demonstrates improved mosquito-repellent efficacy in incense and aerosol formulations, with reduced toxicity to mammals and effective control of pests, including German cockroaches.
Implementation Method 1
its nitrogen-containing structure leads to a lower vapor pressure, making it difficult to volatize through heating to achieve contact-killing effect
Data Source
AI summary
Disclosed are a pyrethroid compound containing a cyano group and a double bond, a synthesis method therefor and an application thereof. In the synthesis method, t-butyl 3-formyl-2,2-dimethyl-cyclopropanoate and cyanomethyl phosphonate are used as raw materials, undergo Witting-Horner reaction, undergo column chromatography to obtain t-butyl (Z)-3-(2-cyanovinyl)-2,2-dimethyl-cyclopropanoate ester, undergo deprotection to obtain (Z)-3-(2-cyanovinyl)-2,2-dimethyl-cyclopropanoic acid, undergo acyl chlorination reaction to produce (Z)-3-(2-cyanovinyl)-2,2-dimethyl-cyclopropanoyl chloride, and are esterified with corresponding alcohol to obtain the pyrethroid compound. The compound can be used as an insecticide against pests such as mosquitoes, flies, German cockroaches and the like.