Synthesis and Herbicidal Activity of Pyrido[2,3-d]pyrimidine-2,4-dione-Benzoxazinone Hybrids as Protoporphyrinogen Oxidase Inhibitors
Synthesis and Herbicidal Activity of Pyrido[2,3-d]pyrimidine-2,4-dione-Benzoxazinone Hybrids as Protoporphyrinogen Oxidase Inhibitors
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原卟啉原氧化酶抑制剂吡啶并[2,3-d]嘧啶-2,4-二酮-苯并恶嗪酮杂化物的合成及其除草活性
DOI：
10.1021/acs.jafc.7b01990
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发表时间：
2017-07-05
影响因子：
6.1
通讯作者：
Xi, Zhen
中科院分区：
文献类型：
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作者：
Wang, Da-Wei;Li, Qian;Xi, Zhen
为了寻找新的具有更高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的吡啶并[2，3-d]嘧啶-2，4-二酮苯并恶嗪酮杂环化合物9-13。通过对烟草多酚氧化酶（mtPPO）抑制活性的研究，发现了几个具有较好除草活性的化合物，其中3-（7-氟-3-氧代-4-（丙-2-炔-1-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，3 H）-二酮，11 q，K-i值为0.0074 μ M，对mtPPO的活性比氟恶嗪（Ki = 0.046 μ M）高6倍。通过出苗后和出苗前施用，化合物11 q在37.5-150 g活性成分（ai）/ha下显示出强且广谱的杂草防治，其与氟恶嗪相当。11 Q在150 g ai/hm 2时对玉米、大豆、花生和棉花安全，在75 g ai/hm 2时对水稻和小麦有选择性，具有潜在的应用价值。
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-i value of 0.0074 mu M, showed six times more activity than flumioxazin (K-i = 0.046 mu M) 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.