Spiro Derivatives in the Discovery of New Pesticides: A Research Review

Abstract

Spiro compounds are biologically active organic compounds with unique structures, found in a wide variety of natural products and drugs. They do not readily lead to drug resistance due to their unique mechanisms of action and have, therefore, attracted considerable attention regarding pesticide development. Analyzing structure−activity relationships (SARs) and summarizing the characteristics of spiro compounds with high activity are crucial steps in the design and development of new pesticides. This review mainly summarizes spiro compounds with insecticidal, bactericidal, fungicidal, herbicidal, antiviral, and plant growth regulating functions to provide insight for the creation of new spiro compound pesticides.

Design, Synthesis, Biological Activity Evaluation and Action Mechanism of Myricetin Derivatives Containing Thiazolebisamide

“…Detailed 1 H, 13 C, 19 F NMR and HRMS characterization data of the objective compounds A1-A23 are included in the support information. Taking A4 as an example, in 1 H-NMR, there is a set of single peaks at δ 12.65 ppm, which is the peak of hydrogen on NH directly connected to the carbonyl and thiazole rings.…”

“…The hydrogen on the carbon atom of the benzene ring attached to the amide bond has a set of multiple peaks at δ 7.32 -7.18 ppm; a single peak is at δ 4.83 ppm, which is the peak of hydrogen on the methylene group attached to the oxygen and carbonyl groups; hydrogens on the five methoxy groups on the main structure are located at δ 3.92 -3.74 ppm; the hydrogen on the methyl group of benzene ring is at δ 2.24 ppm. There are 33 carbon peaks in the 13 C NMR spectrum of A4, which are equal to the number of C atoms in the A4 structure, of which 60.68-56.62 ppm is the carbon peak of methoxy on the main structure; δ 18.41 ppm is the carbon peak of methyl on benzene ring. The HRMS spectrum of the target compounds showed the absorption signals of [M + H] + ions consistent with their molecular weights.…”

Substrate‐Controlled Product Divergence in Iron(III)‐Catalyzed Reactions of Propargylic Alcohols: Easy Access to Spiro‐indenyl 1,4‐Benzoxazines and 2‐(2,2‐Diarylvinyl)quinoxalines

“…), and are therefore considered as privileged scaffolds in medicinal chemistry [1c] . Besides, they find various applications in agrochemicals, [1d] material sciences [1e,f] and functional materials [1g] as well. Among them, spiro‐benzoxazines are considered as a very important sub‐class due to their broad spectrum of biological effects (e. g., compounds I [2a] – II , [2b] Figure 1) which make them more attractive synthetic targets than simple 1,4‐benzoxazines, a common source of a diverse array of bioactive compounds [3a,b] including drugs [3c,d] .…”

Highly Diastereoselective Multicomponent Synthesis of Spirocyclopropyl Oxindoles Enabled by Rare-Earth Metal Salts

“…Finally, we wanted to investigate a possible application for our reaction by choosing propachlor 23 as a surrogate of the 2-bromoacetophenone (Scheme ). Propachlor is a well-known herbicide, and today, much effort is being spent to develop new herbicides, in particular new spiro pesticide derivatives . Therefore, the new spirocyclopropyl derivative 24 may represent a novel substrate with herbicidal properties.…”

“…Propachlor is a well-known herbicide, 30 and today, much effort is being spent to develop new herbicides, 31 in particular new spiro pesticide derivatives. 32 Therefore, the new spirocyclopropyl derivative 24 may represent a novel substrate with herbicidal properties.…”