State Key Laboratory of Elemento-Organic Chemistry, and Department of Chemical Biology, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, Nankai University , Tianjin 300071, P. R. China.
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan 430079, P. R. China.
J Agric Food Chem. 2017 Jul 5;65(26):5278-5286. doi: 10.1021/acs.jafc.7b01990. Epub 2017 Jun 26.
To search for new protoporphyrinogen oxidase (PPO, EC 1.3.3.4) inhibitors with improved bioactivity, a series of novel pyrido[2,3-d]pyrimidine-2,4-dione-benzoxazinone hybrids, 9-13, were designed and synthesized. Several compounds with improved tobacco PPO (mtPPO)-inhibiting and promising herbicidal activities were found. Among them, the most potent compound, 3-(7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-benzo[b][1,4] oxazin-6-yl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, 11q, with a K value of 0.0074 μM, showed six times more activity than flumioxazin (K = 0.046 μM) against mtPPO. Compound 11q displayed a strong and broad spectrum of weed control at 37.5-150 g of active ingredient (ai)/ha by both post- and pre-emergence application, which was comparable to that of flumioxazin. 11q was safe to maize, soybean, peanut, and cotton at 150 g ai/ha, and selective to rice and wheat at 75 g ai/ha by pre-emergence application, indicating potential applicability in these fields.
为了寻找具有更好生物活性的原卟啉原氧化酶（PPO，EC 1.3.3.4）抑制剂，设计并合成了一系列新型吡啶并[2,3-d]嘧啶-2,4-二酮-苯并恶嗪酮杂合体 9-13。发现了几种具有改进的烟草 PPO（mtPPO）抑制作用和有前途的除草活性的化合物。其中，最有效的化合物 3-(7-氟-3-氧代-4-(2-炔丙基)-3,4-二氢-2H-苯并[b][1,4]恶嗪-6-基)-1-甲基吡啶并[2,3-d]嘧啶-2,4(1H,3H)-二酮，11q，K 值为 0.0074 μM，对 mtPPO 的活性比氟草肟（K = 0.046 μM）高六倍。化合物 11q 在 37.5-150 g/ha 的活性成分（ai）后和前处理均表现出强烈和广谱的杂草控制效果，与氟草肟相当。在 150 g ai/ha 时，11q 对玉米、大豆、花生和棉花安全，在 75 g ai/ha 时前处理对水稻和小麦具有选择性，表明在这些领域具有潜在的适用性。
