Owing to the changing needs of agriculture, the exploration of new pest control agents remains as critical as ever. The analogues 3a–3v of the natural product cerbinal were synthesized from genipin by an efficient and practical method under additive-free conditions. The antiviral and insecticidal effects of cerbinal and these cyclopenta[c]pyridines (3a–3v) were evaluated systematically. Most of the synthesized compounds exhibited higher anti-TMV activities than the lead compound cerbinal. Compound 3s (2-(4-methoxyphenyl)) had the most promising inhibitory activities against TMV (inactivation effect 49.0 ± 0.8%, curative effect 41.2 ± 4.3%, and protection effect 51.5 ± 2.7% at 500 μg/mL). Among the synthesized compounds, only 3v (2-(2-chloro-4-(trifluoromethoxy)phenyl)) reached the activity level of cerbinal against Plutella xylostella. This suggested that the cyclopenta[c]pyridines obtained by modifications of cerbinal at position 2 are very significant for the anti-TMV activity, and yet were exceptionally less active for the insecticidal activities.

中文翻译：

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天然产物Cerbinal及其类似物环戊[ c ]吡啶：合成和发现作为新型害虫防治剂。

由于农业需求的变化，对新型害虫防治剂的探索仍然像从前一样至关重要。天然产物ceralinal的类似物3a – 3v是由genipin在无添加剂条件下通过一种有效且实用的方法合成的。系统地评估了cerbinal和这些环戊[ c ]吡啶（3a - 3v）的抗病毒和杀虫效果。大多数合成的化合物显示出比先导化合物cerbinal更高的抗TMV活性。复合3s（2-（4-甲氧基苯基））在500μg/ mL时对TMV具有最有希望的抑制活性（灭活作用49.0±0.8％，治愈作用41.2±4.3％和保护作用51.5±2.7％）。在合成的化合物中，只有3v（2-（2-氯-4-（三氟甲氧基）苯基）达到了宫颈对小菜蛾的活性水平。这表明通过修饰2位上的宫颈而获得的环戊并[ c ]吡啶对于抗TMV活性非常重要，而对杀虫活性却异常低。