Design, synthesis, and insecticidal activity of pyrimidinamine derivatives containing 2-pyridinyloxy moiety,Journal of Heterocyclic Chemistry

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Design, synthesis, and insecticidal activity of pyrimidinamine derivatives containing 2-pyridinyloxy moiety
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2023-03-25 , DOI: 10.1002/jhet.4651
Shilin Lan _{1,

2} , Ting Xiao _{1,

3} , Shaofei Guan _{1,

4} , Aiping Liu _{1,

2} , Chuyun Long ₁ , Fujun Zhong ₁ , Zhichang Huang ₁ , Xingping Liu ₁ , Zai Zhang ₁ , Weidong Liu _{1,

5}

Affiliation

Aphis fabae is a widespread pest that has more than 200 hosts in the world, belongs to hemiptera, for stinging suction mouthparts, harm buds, young leaves, and flower buds. Pyrimidine derivatives have the advantages of insecticidal, bactericidal, herbicidal, regulating plant growth and other biological activities, and have a unique mechanism of action. Pyrimidinamine derivatives, one of pyrimidine derivatives, were reported as early as 1955, and all the world's major pesticide companies (Syngenta, Dow Yinon, Bayer, DuPont, and BASF) have carried out research studies, which had lasted for nearly 60 years. For example, commercial pyrimidine products such as flupyrimethanil (fungicide) and pyrimethanil (insecticidal and acaricidal agents) show excellent biological activity. So pyrimidinamine derivatives are considered promising agricultural compounds. In this study, a series of pyrimidinamine derivatives were designed and synthesized using pyrimidifen as a template according to bioisosterism. 5-chloro-N-(1-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)-2-methylpropan-2-yl)- 6-ethylpyrimidin-4-amine, T23, had the best control effect on Aphis fabae with LC₅₀ values of 1.46 mg/L, versus commercial insecticides spirotetramat and imidacloprid (2.45 and 0.53 mg/L). The synthesis, characterization, and activity data of the compounds are presented in the text, and the structure–activity relationships are discussed.

中文翻译：

含2-吡啶氧基的嘧啶胺衍生物的设计、合成及杀虫活性

蚕豆蚜是一种分布广泛的害虫，全世界有200多种寄主，属半翅目，以刺吸式口器、危害芽、嫩叶、花蕾为害。嘧啶类衍生物具有杀虫、杀菌、除草、调节植物生长等多种生物活性，具有独特的作用机理。嘧啶衍生物之一的嘧啶胺衍生物早在1955年就被报道，世界各大农药公司（先正达、陶氏益能、拜耳、杜邦、巴斯夫）都进行了研究，历时近60年。例如，氟嘧啶（杀菌剂）和嘧霉胺（杀虫剂和杀螨剂）等商业嘧啶产品显示出优异的生物活性。因此，嘧啶胺衍生物被认为是有前途的农用化合物。本研究以嘧啶胺为模板，根据生物电子等排原理，设计合成了一系列嘧啶胺类衍生物。5-氯-N -(1-((3-chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)-2-methylpropa n -2-yl)- 6-ethylpyrimidin-4-amine, T23防治效果最好对蚕豆蚜的 LC ₅₀值为 1.46 mg/L，而商业杀虫剂螺虫乙酯和吡虫啉（2.45 和 0.53 mg/L）。文中介绍了化合物的合成、表征和活性数据，并讨论了构效关系。

更新日期：2023-03-25

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