Synthesis and Biological Activity of Some New 6‐perfluoropropanyl Quinoline Derivatives

Abstract

A series of new quinoline derivatives containing perfluoropropanyl moiety were designed and synthesized. Their structures were confirmed by 1 H NMR, MS, and elemental analysis. The bioassay results showed that some of them exhibited good control efficacy against Pyricularia oryae. Also, some of the title compounds exhibited good insecticidal activity against Aphis craccivora Koch, Plutella xylostella, Mythimna Separate, and Tetranychus cinnabarinus.

Synthesis and Insecticidal Activity of New Quinoline Derivatives Containing Perfluoropropanyl Moiety

“…The synthetic route was shown in Scheme . Generally, 2‐methyl‐4‐(perfluoropropan‐2‐yl)aniline was prepared from 2‐methyl aniline and 1,1,1,2,3,3,3‐heptafluoro‐2‐iodopropane reagent as starting materials according to our previous work . The mechanism of the key intermediate 2‐methyl‐4‐(perfluoropropan‐2‐yl)aniline was shown in Scheme .…”

“…The synthetic route was shown in Scheme 2. Generally, 2-methyl-4-(perfluoropropan-2-yl)aniline was prepared from 2-methyl aniline and 1,1,1,2,3,3,3-heptafluoro-2iodopropane reagent as starting materials according to our previous work [9][10][11][12][13]. The mechanism [37] [43], microwave method [44], Pfitzinger method [45], and one pot method [46].…”

“…In our previous work [9][10][11][12][13], we found that the perfluoropropanyl group on the quinoline ring can increase the fungicidal activity, so in line with our continued efforts to synthesize novel lead compounds for drug discover , the fungicide tebufloquin was selected as a lead compound, the t-Bu group was replaced by perfluoropropanyl group, the methyl group was replaced by chlorine atom, the fluorine atom was replaced by methyl group, and the ether group was replaced by ester carbonate. Our original strategy is depicted in Scheme 1.…”

Synthesis and Fungicidal Activities of 2,3‐Dimethyl‐4‐(1‐acyloxy)alkoxy‐6‐tert‐butyl‐8‐fluoroquinolines

“…Heterocyclic agrochemicals containing nitrogen has better activity, including insecticidal [4,5], antimicrobial [6], antiviral [7], fungicidal [8][9][10][11], and herbicidal [12]. Quinolines are one of the most important compounds in nitrogen-containing heterocycles and exhibited appreciable fungicidal activity [13][14][15]. For example, Quioxyfen is an effective antipowdery mildew agent.…”

“…1) is an active intermediate and possess excellent activity (93%) against rice blast at 3 mg/L [23]. In our previous work [13][14][15], a series of quinoline compounds were designed and synthesized; the bioassay results indicated that the quinoline compounds containing fluorine atom showed better fungicidal activity than other halo atom. Hence, a series of 2,3-dimethyl-4-(1-alkyl acetoxy)-6-tert-butyl-8-fluoroquinolines were designed, and their fungicidal activities were evaluated.…”