Pyridazine Chemistry in Crop Protection

Oxazole and Isoxazole Chemistry in Crop Protection

“…in different crops by interference with the regulation of osmosis [26]. Famoxadone (16), another oxazolidindione derivative, binds to the ubiquinol-oxidation center (Qo site) of cytochrome b, a part of the fungal cytochrome bc 1 complex (complex III of the respiratory chain) and is specialized on the devastating Oomycetes species Phytophthora infestans (causal agent of potato late blight) and Plasmopara viticola (causal agent of grape downy mildew) [27]. The same phytopathogens are also controlled by the oxazolidinone derivative oxadixyl (17) that belongs to the ribosomal RNA biosynthesis inhibiting phenylamide fungicides [28].…”

“…The isoxazolone derivative 34 [44], the isoxazole derivative 35 [45], and the benzoxazole derivative 36 [46] all belong to the fungicide family of strobilurins and inhibit, such as famoxadone (16), complex III in the fungal respiratory chain. The isoxazolone and isoxazole rings within 34 and 35 are part of their pharmacophore and therefore a cyclic version of the well-known oximinoacetamide strobilurin subclass, whereas the benzoxazole ring system of 36 represents the typical lipophilic side chain of strobilurin fungicides.…”

“…Also, the application of most of these heterocyclic scaffolds in medicinal chemistry has been reviewed recently, just to mention the broad pharmacological (e.g., anticancer, antimicrobial, antidiabetic, anti‐inflammatory, and anticonvulsant) activity of benzoxazoles or the specific significance of isoxazoles for neuropsychiatric therapeutics . The only heterocyclic scaffolds, for which so far extensive reviews exist regarding their significance in crop protection chemistry, are pyrazole , thiazole , isothiazole , pyridine , pyridazine , and pyrimidine . This review deals with the agrochemical aspects of oxazoles and isoxazoles as well as their bicyclic, partially saturated and fully saturated as well as oxygenated derivatives.…”

Design, synthesis, and bioactivities of novel pyridazinone derivatives containing 2‐phenylthiazole or oxazole skeletons

“…This pharmacophore is commonly found in herbicides in the market, although there are a few insecticide applications. [ 9–12 ] Some pyridazinone agrochemicals are represented in Figure 1. Among them, 2‐( tert ‐butyl)‐5‐((4‐( tert ‐butyl)benzyl)thio)‐4‐chloropyridazin‐3(2 H )‐one (NC‐129) developed by Nissan Chemical under the trade name “Pyridaben” in 1991 is the most important insecticide of this class.…”

“…More importantly, this ingredient is safe to a range of beneficial insects. [ 10,13,18 ] Although many insects, especially phytophagous mites, such as: Auphitetranychus viennensis zache , T urticae , and Panonychus citri have developed moderate or high levels resistance to pyridaben. [ 19–22 ] we believe pyridazinone worth more exploration given its high insecticidal activity and low toxicity.…”