Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, China Agricultural University, Beijing 100193, People's Republic of China.
J Agric Food Chem. 2010 Jun 9;58(11):6858-63. doi: 10.1021/jf1000919.
Fluobendiamide is the first commercialized artificial synthetic insecticide acting on the ryanodine receptor. This new molecule possesses a combination of excellent insecticidal activity and eco-friendly characteristics with a skeleton structure of phthalamide. In this study, we incorporated hydrazone, present in many pesticidal compounds reported during the last two decades, into phthalamide derivatives via Schiff-base condensation and aminolysis to obtain 21 new compounds; these compounds were characterized by proton nuclear magnetic resonance ((1)H NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS) or elemental analysis. A preliminary bioassay against peach aphids ( Myzus persicae ) revealed that the title compounds exhibited good stomach toxicity at 600 mg/L. Twelve new compounds were found to display higher activity than postive control flubendiamide (LC(50) = 184.099 mg/L), however, LC(50) was less than 100 mg/L only for compounds 4e, 4o, 4s, 4t (59-77 mg/L). That is, combinations of a p-fluorophenyl or (methyl)thienyl group at the Ar position with an isopropyl or cyclohexyl group at the R position might improve the lethality of the designed phthalamide derivative. Preliminary results of a bioassay at 600 mg/L against diamondback moth ( Plutella xylostella , Linnaeus) showed that only the title compound 4e possessed good larvicidal activity. On comparison of the bioassay results of stomach toxicity and larvicidal activity, it is noteworthy that the compound incorporating phenylpyrazolyl exhibited good larvicidal activity and poor stomach activity.
氟苯虫酰胺是第一个作用于兰尼碱受体的商业化人工合成杀虫剂。这种新分子具有优异的杀虫活性和生态友好特性，其骨架结构为邻苯二甲酰胺。在这项研究中，我们通过席夫碱缩合和氨解将酰腙（在过去二十年报道的许多农药化合物中都存在）引入邻苯二甲酰胺衍生物中，得到了 21 种新化合物；这些化合物通过质子核磁共振谱（(1)H NMR）、红外光谱（IR）和高分辨率质谱（HRMS）或元素分析进行了表征。对桃蚜（Myzus persicae）的初步生物测定表明，标题化合物在 600mg/L 时表现出良好的胃毒性。发现 12 种新化合物的活性高于阳性对照氟苯虫酰胺（LC(50) = 184.099mg/L），但 LC(50) 低于 100mg/L 的仅有化合物 4e、4o、4s、4t（59-77mg/L）。也就是说，在 Ar 位置上具有对氟苯基或（甲基）噻吩基与在 R 位置上具有异丙基或环己基的组合可能会提高设计的邻苯二甲酰胺衍生物的致死率。在 600mg/L 下对小菜蛾（Plutella xylostella，Linnaeus）进行生物测定的初步结果表明，只有标题化合物 4e 具有良好的幼虫杀灭活性。比较胃毒性和幼虫杀灭活性的生物测定结果，值得注意的是，含有苯基吡唑基的化合物表现出良好的幼虫杀灭活性和较差的胃活性。
