Synthesis and structure–activity relationships of chlordimeform imine analogues against Chilo suppressalis

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2026-04-03 Epub Date: 2026-03-26 DOI:10.1080/00397911.2026.2640565

Xiyan Tang (Investigation Software Validation) , Lijie Che (Formal analysis Investigation Methodology Validation Writing – original draft) , Yanmin Huang (Conceptualization Funding acquisition Methodology Project administration) , Jianguo Cui (Conceptualization Project administration Supervision) , Zhiping Liu (Conceptualization Investigation Supervision Writing – review & editing)

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Abstract

To address the high carcinogenicity of 4-chloro-2-methylaniline (a metabolite of traditional chlordimeform), thirty chlordimeform imine analogues were synthesized using chlordimeform as the lead compound, retaining the core amidine group (–N = CH–N(CH₃)₂) while modifying the benzene ring. The synthesized amidine structures were confirmed by ¹H/¹³C/¹⁹F NMR spectroscopy. Insecticidal activity against resistant Chilo suppressalis was evaluated via the soaked water-oat stem method. At a concentration of 50 μg/mL, compounds 4d, 4m, 9c, and 9d exhibited a corrected mortality rate of more than 38.67%, which was superior to chlordimeform (22.00%) but significantly lower than that of the commercial insecticide fipronil (88.00%). Preliminary SAR analysis: Retaining the benzene ring’s 2-methyl group and replacing the 4-chloro with fluorine, cyano, phenoxy, or benzyloxy enhanced the insecticidal activity; replacing benzene with heterocycles/fused heterocycles (except pyrazole-substituted 4m) reduced the insecticidal activity. This study provides theoretical insights and candidate compounds for novel amidine-based insecticides.

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氯甲胺磷亚胺类似物的合成及构效关系

针对传统氯仿代谢物4-氯-2-甲基苯胺致癌性高的问题，以氯仿为先导化合物，保留核心脒基（-N = CH-N (CH3)2），对苯环进行修饰，合成了30个氯仿亚胺类似物。经1H/13C/19F核磁共振确证了合成的酰胺类化合物的结构。采用水-燕麦茎浸渍法测定了其对抗性辣椒的杀虫活性。在50 μg/mL浓度下，化合物4d、4m、9c和9d的校正死亡率均大于38.67%，优于氯甲脒（22.00%），但显著低于氟虫腈（88.00%）。初步SAR分析：保留苯环的2-甲基，用氟、氰基、苯氧基或苯氧基取代4-氯，增强了杀虫活性；以杂环/融合杂环取代苯（吡唑取代的4m除外），杀虫活性降低。本研究为新型脒类杀虫剂提供了理论见解和候选化合物。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.