Synthesis and Insecticidal Activity of Novel meta-Diamide Compounds Containing Cyclopropyl Group

Abstract

To discover novel insecticide with improved activity, a series of meta-diamide compounds containing cyclopropyl moiety were synthesized on the principle of biologically active factor splicing. The structures of synthetic derivatives were characterized by 1 H NMR, 13 C NMR and HRMS. Preliminary bioassay data showed that some of the title compounds exhibited good insecticidal activities against Plutella xylostella and Chilo suppressalis. Among them, the mortality of N-(2-bromo-4-(perfluoropropan-2-yl)-6-(trifluoromethyl)phenyl)-3-(N-(cyclopropylmethyl)benzamido)-2-fluorobenzamide (6d) and 3-(N-(cyclopropylmethyl)benzamido)-N-(2,6-dibromo-4-(perfluoropropan-2-yl)phenyl)-2-fluorobenzamide (6e) was 100% against Plute-lla xylostella at 1 mg/L, and the mortality of compound 6d was 100% against Chilo suppressalis at 5 mg/L. Keywords synthesis; cyclopropyl; meta-diamide; inseticidal activity 21 世纪以来, 杀虫剂的发展进入高效、低毒、环境 友好时期. 双酰胺类杀虫剂因对鳞翅目害虫高效, 且与 其它常用杀虫药剂间无交互抗性, 同时对哺乳动物安 全, 因此被广泛使用 [1][2][3][4] . 双酰胺类杀虫剂的主要品种有 氟苯虫酰胺(Flubendiamide, 1)、氯虫苯甲酰胺(Chlorantraniliprole, 2)和溴氰虫酰胺(Cyantraniliprole, 3) [5][6][7][8] . 由 于氯虫苯甲酰胺等的大量推广使用, 其存在很大的抗性 风险, 多种害虫的田间种群已对其产生了抗药性 [9][10][11][12][13] .

Novel Meta-Diamide Compounds Containing Sulfide Derivatives Were Designed and Synthesized as Potential Pesticides

“…The reaction could not proceed when N,N-Dimethylformamide (DMF) was used as a solvent with 5, NaOH, FeSO 4 •7H 2 O and (CF 3 ) 2 FCI under one-pot reaction conditions [15] (Table 1, entries 1-4). However, employing a two-phase system consisting of ethyl acetate (EA) and water (H 2 O) as solvents, and tetrabutylammonium hydrogen sulfate (IPC-TBA-HS) as a phase transfer catalyst, with the equivalent ratio of compounds 5:Na 2 S 2 O 4 :NaHCO 3 :IPC-TBA-HS:(CF 3 ) 2 FCI being 1:1.1:1.1:0.3:2, the reaction system was successfully completed after heating and refluxing for about 12 h as monitored by thinlayer chromatography (TLC) [5] To circumvent the use of harsh conditions, such as the employment of strong bases at low temperatures (e.g., Lithium Diisopropylamide (LDA) or Sodium Hydride (NaH) at −70 °C) [16] or solvents with high boiling points [2], the study aimed to prepare target compounds A under milder conditions. A comprehensive review of the literature and an analysis of the reaction mechanism facilitated the exploitation of differences in the nucleophilicity and leaving abilities of halogen atoms for the synthesis of target compounds A.…”

“…Optimization of reaction conditions for the synthesis compound 6a. To circumvent the use of harsh conditions, such as the employment of strong bases at low temperatures (e.g., Lithium Diisopropylamide (LDA) or Sodium Hydride (NaH) at −70 • C) [16] or solvents with high boiling points [2], the study aimed to prepare target compounds A under milder conditions. A comprehensive review of the literature and an analysis of the reaction mechanism facilitated the exploitation of differences in the nucleophilicity and leaving abilities of halogen atoms for the synthesis of target compounds A.…”

Fluorinated or brominated meta‐diamides as the new scaffolds for the treatment of rice bacterial leaf blight

“…Many studies have focused on diverse substitutions on the benzene ring based on the meta‐diamides structure of meta‐diamides (Liu et al, 2021). Specifically, Liu et al introduced the heterocycles thiophene, thiazole, pyrazole, and ( E )‐prop‐1‐en‐1‐ylbenzene to replace the benzene ring and placed an n ‐butyl group on the N atom of amide (Figure 2; Huang et al, 2022; Luo, Ma, et al, 2020). Park et al used a pentafluorosulfanyl group (SF 5 ) to replace the heptafluoroisopropyl moiety (Figure 2; Kim et al, 2020).…”