N-[4-氯-2-取代氨基甲酰基-6-甲基苯基]-1-芳基-5-氯-3-三氟甲基-1H-吡唑-4-甲酰胺的合成及生物活性

通过改变传统氯虫酰胺中吡唑环上氨基甲酰基与吡啶环之间的相对位置, 或以其它芳环取代原分子中的吡啶环, 设计合成了24个结构新颖的N-4-氯-2-取代氨基甲酰基-6-甲基苯基]-1-芳基-5-氯-3-三氟甲基-1H-吡唑-4-甲酰胺类化合物. 所有目标化合物的结构均通过¹H NMR谱、 元素分析或高分辨质谱表征确定. 初步的生物活性测试结果表明, 部分化合物对东方粘虫具有较好的杀虫活性, 其中化合物6m在浓度为50 mg/L时具有80%的杀虫活性. 同时, 在浓度为50 mg/L时目标化合物对5种常见病菌具有明显的抑制作用, 其中化合物6n和6x对苹果轮纹菌的抑菌率达62.1%.

Synthesis and Insecticidal Activity of 5-Chloro-N-[4-chloro-2-(substitutedcarbamoyl)-6-methylphenyl]-1-aryl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide

In the 21st century, one of the most serious challenges to mankind is food which plays a critical role to their survival and development. Seeking novel pesticides with new mechanism is an important approach in plant protection science. Anthranilic diamides recently appeared are of new type of potent insecticides which acts at ryanodine receptor of target insects. DuPont’s Chlorantraniliprole has become one of the focuses in the innovation of agrochemicals due to its high efficiency, low toxicity, broader insecticidal spectra and significant ovicidal activity. Since it came to the world market from 2008, there have been numerous patents relating to new structural optimization reports. Most of them retained the N-pyridylpyrazole moiety, and kept carbamoyl in the ortho-position with pyridyl moiety in pyrazole ring. It was postulated that the activity could be improved by changing the distance between carbamoyl and pyridyl in pyrazole ring or displacing the pyridyl with other aryls. 24 novel anthranilic diamides containing 1-aryl-5-chloro-3-(trifluoromethyl)-1H-pyrazole moieties were designed and synthesized. Their structures were characterized by ¹H NMR and elemental analysis or HRMS. The preliminary bioassay results indicated that all compounds exhibit moderate insecticidal activity against Mythimna separate at 200 mg/L and some of them exhibited good insecticidal activity at a concentration of 50 mg/L; most compounds exhibited unexpectedly fungicidal activity against five funguses at a concentration of 50 mg/L.