Synthesis, Fungicidal, and Insecticidal Activities of β-Methoxyacrylate-Containing N-Acetyl Pyrazoline Derivatives

Abstract

1-Acetyl-3,-5-diarylpyrazolines have received considerable interests from the fields of medicinal and agricultural chemistry due to their broad spectrum of biological activities. To discover new lead compounds exhibiting both fungicidal and insecticidal activities, a series of pyrazoline derivatives were designed and synthesized by introducing the beta-methoxyacrylate pharmacophore into the scaffold of 1-acetyl-3,5-diarylpyrazoline. The fungicidal activities against Pseudoperoniospora cubensis, Sphaerotheca fuliginea, Botrytis cinerea, and Rhizoctonia solani and the insecticidal activities against Aphis medicagini, Nilaparvata legen, Mythima separata, and Tetranychus cinnabarnus were screened. The most potent compound 13, 1-aceto-3-[m-[o-(E-1-methoxycarboxyl-2-methoxy)-1-yl]benzyloxy]phenyl-5-(benzo-[1,3]-dioxolyl)-4,5-dihydro- pyrazoline, was identified. Its fungicidal IC(50) values against P. cubensis and S. fuliginea are 26.6 and 57.6 microg mL(-1), respectively, while its insecticidal LC(50) value against M. separata is 26.6 microg mL(-1). These results indicated that compound 13 could be used as a lead for further developing new pyrazoline type products exhibiting both fungicidal and insecticidal activities.

Solvent-Free Synthesis and Spectral Correlation of ¹<i>N</i>-Acetyl-3-(4-β-Methacrylate)-5-(Substituted Phenyl)-4,5-Dihydro-¹<i>H</i>-Pyrazolines

“…This is due to the reasons stated earlier and it is associated with the resonance-conjugated structure as shown in Figure 2 In view of the inability of some of the σ constants to produce individually satisfactory correlation for C=O, CH 3(keto) , C=N, CH 2 , C α , C β , OCH 3 , C=O (ester) , and CH 3(ester) carbons, the authors think that, it is worthwhile to seek multiple correlation involving either σ I , σ R or F and R parameters [30]. The formulated multi-correlation equations are given in (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40). …”

Synthesis, Crystal Structure and Insecticidal Activity of the Optical Active Neonicotinoid Analogues

“…The bioassay was measured according to the standard test 24 with a slight modification. Insecticidal activities of the compounds (3a-3h) were tested against Nilaparvata legen (N. legen).…”

Synthesis of 1-phenyl-3-(4’-nitrophenyl)-5-(3’,4’-dimethoxy-6’-nitrophenyl)-2-pyrazoline and its antibacterial activity

“…Pyrazole and pyrazoline are important nitrogen containing 5-membered heterocyclic compound. Pyrazoline which is well known as pyrazole derivative or 4,5-dihydropyrazole is reported possess a broad spectrum of biological activities such as anticonvulsant [2], antimicrobial [1,3,8], antiamoebic [3], analgesic [1], anti-inflammmatory [1], antidepressant [4], anxiogenic [4], inhibitors of monoamine oxidase [4], fungisical [5], insecticidal [5], antitumor [6], and antinociceptive [7]. Therefore, the prevalence of pyrazole core in biologically active molecules has stimulated the need for elegant and efficient ways to make these heterocyclic lead.…”