3-(5 amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(5 amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione
• 英文别名: 3-(5-Amino-2,4-dichlorophenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione
• 化学式: C₁₂H₈Cl₂F₃N₃O₂
• 分子量: 354.116
• InChiKey: XOFWQQIDOULUTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(5 amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-[2,4-dichloro-5-bis(ethanesulfonyl)-aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Uracil derivatives and herbicides containing the same as active ingredient

  摘要：

  公式 (I) 所代表的尿嘧啶衍生物：其中 R⁷ 代表氢或卤素，R⁸ 代表卤素，D²⁶ 代表C₁₋₄烷基或C₁₋₃卤代烷基；具有除草剂作用。

  公开号：

  EP0489480A1
• 作为产物：
  描述：

  2-(dimethylamino)-4-(trifluoromethyl)-1,3-oxazin-6-one 在 硫酸 、 硝酸 、 铁粉 、 caesium carbonate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(5 amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione
  参考文献：
  名称：

  通过反应中间衍生方法发现 N-苯氨基甲基硫代乙酰基嘧啶-2,4-二酮作为原卟啉原 IX 氧化酶抑制剂

  摘要：

  原卟啉原氧化酶（PPO，EC 1.3.3.4）是发现绿色除草剂的有效靶点。在这项工作中，我们在研究我们最初设计的N-苯基尿嘧啶噻唑烷酮 ( 1 ) 的反应中间体的基础上，意外发现了一系列新的N-苯基氨基甲硫基乙酰基嘧啶-2,4-二酮 ( 2-6 ) 作为有前景的 PPO 抑制剂。开发了一种高效的一锅法程序，可以以良好到高的收率产生 41 种目标化合物。系统性烟草PPO (NtPPO) 抑制和除草活性评估导致鉴定出一些化合物，其 NtPPO 抑制效力优于苯嘧磺草胺，并且在 37.5-150 g ai/ha 下具有良好的芽后除草活性。在这些类似物中，乙基 2-((((2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-(三氟甲基)-3,6-二氢嘧啶-1(2 H )-基)苯基)氨基)甲基)硫代)乙酸酯 ( 2c ) ( K i = 11 nM)，在 37.5–150 g ai/ha 时表现出优异的杂草控制效果，并且在

  DOI：

  10.1021/acs.jafc.1c00796

文献信息

• 1-(3-Heterocyclylphenyl)isothiourea, -isourea, -guanidine and -amidine compounds as herbicides
  申请人：American Cyanamid Company

  公开号：EP0985670A1

  公开（公告）日：2000-03-15

  There are provided 1-(3-heterocyclyphenyl)isothiourea, -isourea, -guanidine and -amidine compounds of formula I Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.

  提供了式I的1-(3-杂环苯基)异硫脲、-异脲、-胍和-胺类化合物。还提供了包含这些化合物的组合物和方法，用于控制不良植物物种。
• 化合物及其制备方法和用途
  申请人：华中师范大学

  公开号：CN105218582B

  公开（公告）日：2017-03-22

  本发明提供了化合物及其制备方法和用途，特别是式I所示化合物或其对映异构体、非对映异构体、外消旋体、药学上可接受的盐、结晶水合物、酮‑烯醇互变异构化合物或溶剂合物，R1为至少一个卤素、氢；R2为任选取代的苯基；R3和R4分别独立地为H或任选取代的烷基。本发明提供的化合物具有除草活性。
• Uracil derivatives and herbicides containing the same as active
  申请人：Nissan Chemical Industries Ltd.

  公开号：US05154755A1

  公开（公告）日：1992-10-13

  Disclosed herein is uracil derivatives having a trifluoromethyl group at the 6-position and a phenyl group at the 3-position which has a NHSO.sub.2 D.sup.26 group at 5-position of the benzene ring, halogen atom at 4-position thereof and hydrogen atom or halogen atom at 2-position thereof, which are represented by the formula (I) and showing penetrative translocation activity, a very high herbicidal activity and, particularly, no phytotoxicity against soybean, in which as compared with the conventional herbicidal compounds, the said uracil derivatives can be applied for either soil treatment or soil incorporation treatment, thereby producing a quick and high herbicidal effect even at a very low dosage against a large variety of weeds including perennial weeds, and have the property to residual effect for an appropriate period of time.

  本发明涉及尿嘧啶衍生物，其在6位具有三氟甲基基团，在3位具有苯基，在苯环的5位有NHSO.sub.2 D.sup.26基团，在4位有卤原子，在2位有氢原子或卤原子，其由式(I)表示，具有穿透转位活性、非常高的除草活性，并且特别是对大豆没有植物毒性。与传统的除草化合物相比，这些尿嘧啶衍生物可以用于土壤处理或土壤掺入处理，即使在非常低的用量下也能产生快速和高效的除草效果，包括多年生杂草在内的各种杂草，并具有适当一段时间的残留效果。
• 1 - (3-heterocyclylphenyl) isothiourea, -isourea, -guanidine and -amidine herbicidal agents
  申请人：Intellectual Property Department, BASF Aktiengesellschaft

  公开号：US20020137929A1

  公开（公告）日：2002-09-26

  There are provided 1-(3-heterocyclyphenyl)isothiourea, -isourea, -guanidine and -amidine compounds of formula I 1 Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.

  提供了式子I1中的1-(3-杂环苯基)异硫脲、异脲、鸟嘌呤和脒类化合物，此外还提供了包含这些化合物的组合物和方法，用于控制不良植物物种。
• Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety
  作者：Jian-yi Che、Xiao-yun Xu、Zi-long Tang、Yu-cheng Gu、De-qing Shi

  DOI：10.1016/j.bmcl.2016.01.010

  日期：2016.2

  A series of novel alpha-amino phosphonate derivatives containing a uracil moiety 3a-3l were designed and synthesized by a Lewis acid (magnesium perchlorate) catalyzed the Kabachnik-Fields reaction. The bioassays in vitro, in vivo [Glass House 1 (GH1) and Glass House 2 (GH2)]} showed that most of compounds 3 exhibited excellent and selective herbicidal activities; for example, in GH1 test, compounds 3b, 3d, 3f, 3h and 3j showed excellent and wide spectrum herbicidal activities at the dose of 1000 g/ha, and compounds 3b and 3j exhibited 100% inhibition activities against the four plants in both post- and pre-emergence treatments. Moreover, most of compounds 3 showed higher inhibition against Amaranthus retroflexus and Digitaria sanguinalis than Glyphosate did in pre-emergence treatment. In GH2 test, the four compounds (3b, 3d, 3h and 3j) exhibited 100% inhibition against Solanum nigrum, Amaranthus retroflexus and Ipomoea hederacea in post-emergence treatment and displayed 100% inhibition against Solanum nigrum, Amaranthus retroflexus in pre-emergence treatment at the rate of 250 g/ha, and compound 3b showed the best and broad spectrum herbicidal activities against the six test plants. However, the four compounds displayed weaker herbicidal activities against Lolium perenne and Echinochloa crus-galli than the other four plants at the rate of 250 g/ha in both pre- and post-emergence treatments. So, compounds 3 can be used as a lead compound for further structure optimization for developing potential selective herbicidal agent. Their preliminary structure-activity relationships were also investigated. (C) 2016 Elsevier Ltd. All rights reserved.