5-Aminopyrazole Carbamate Derivatives for Ectoparasite Control
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Solution Overview
Problem
Current pesticides face challenges in terms of efficacy, toxicity, resistance, and environmental impact, necessitating the development of novel compounds with improved activity, lower dosages, and safer profiles for use in domestic animals and the environment.
Innovation Solution
The development of 5-aminopyrazole carbamate derivatives with ketone-oxime groups, which are designed to be effective as systemic ectoparasiticides with reduced toxicity and environmental impact, offering improved activity and longer-lasting protection against ectoparasites.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If conventional pesticides are used to control ectoparasites, then pesticidal activity is achieved, but toxicity to users and environmental harm increase
Solution Approach 1:
The patent modifies the chemical structure of pyrazole compounds by introducing specific substituents (halogen atoms at positions 2 and 6, trifluoromethyl group at position 4, and various R1-R7 groups) to optimize the balance between pesticidal activity and reduced toxicity. The compounds of formula (I) with specific parameter combinations achieve enhanced efficacy while lowering harmful effects compared to conventional pesticides
Solution Approach 2:
The invention creates composite molecular structures combining pyrazole core with carbamate, oxime, and various substituent groups to form new chemical entities that exhibit synergistic properties. The combination of multiple functional groups in single molecules (e.g., compounds with both carbamate and oxime groups) provides improved activity profile with reduced toxicity
2Reliability
If higher dosages of pesticides are applied to ensure efficacy, then pesticidal activity is improved, but toxicity and environmental impact worsen
Solution Approach 1:
The optimized chemical structure of compounds (I) with specific substituent patterns enables achieving high pesticidal activity at lower dosages. The molecular parameters (substituent types, positions, and configurations) are tuned to maximize bioactivity while minimizing the amount of active substance required, thereby reducing toxicity and environmental burden
3Speed
If short-acting pesticides are used, then rapid action is achieved, but duration of protection is insufficient
Solution Approach 1:
The compounds of formula (I) are designed to provide continuous protective action against ectoparasites over extended periods. The molecular structure enables sustained biological activity through mechanisms such as systemic absorption and prolonged release, ensuring continuous protection rather than transient effects, thereby eliminating the need for frequent reapplication
4Reliability
If pesticides are applied topically, then direct contact with parasites is achieved, but contamination of humans and environment occurs
Solution Approach 1:
The patent employs oral administration as an intermediary approach, where compounds (I) are given to animals through feed or water, allowing systemic distribution throughout the body. This intermediary route enables the active substance to reach parasites through the animal's system rather than direct external application, thereby preventing environmental contamination while maintaining efficacy
Data Source
AI summary
Disclosed are compounds of formula (I) or pesticidally acceptable salts thereof wherein, for example, W is ═CR8— or ═C(NR9R10)—, R8 is halogen, R9 and R10 are independently of one another hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, aralkyl or heterocyclylalkyl, R1 is cyano, methyl, trifluoromethyl or —CS—NH2, R2 is C1-C6-alkyl, C1-C6-haloalkyl, R3 is hydrogen, alkyl or cycloalkyl, R4 and R5 are alkenyl, alkynyl or cycloalkyl, R6 is haloalkyl, haloalkoxy, halogen or —SF5, R7 is halogen or alkyl, and n is 0, 1 or 2. These compounds can be used for controlling pests, especially by treatment of domestic animals.