3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine | 123250-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine
• 英文别名: 7-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-one；7-fluoro-6-isocyanato-4-propargyl-4H-1,4-benzoxazin-3-one；7-fluoro-6-isocyanato-4-propargyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine；7-fluoro-6-isocyanato-4-(2-propynyl)-2 H-1,4-benzoxazin-3(4 H)-one；7-fluoro-6-isocyanato-4-prop-2-ynyl-1,4-benzoxazin-3-one
• CAS: 123250-00-0
• 化学式: C₁₂H₇FN₂O₃
• 分子量: 246.198
• InChiKey: OPALMTTXHJIANP-UHFFFAOYSA-N

物化性质

• 沸点：
  490.1±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine 在 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Design, Herbicidal Activity, and QSAR Analysis of Cycloalka[d]quinazoline-2,4-dione–Benzoxazinones as Protoporphyrinogen IX Oxidase Inhibitors

  摘要：

  In continuation of our search for potent protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) inhibitors, we designed and synthesized a series of novel herbicidal cycloalka[d]quinazoline-2,4-dione-benzoxazinones. The bioassay results of these synthesized compounds indicated that most of the compounds exhibited very strong Nicotiana tabacum PPO (NtPPO) inhibition activity. More than half of the 37 synthesized compounds displayed over 80% control of all three tested broadleaf weeds at 37.5-150 g ai/ha by postemergent application, and a majority of them showed no phytotoxicity toward at least one kind of crop at 150 g ai/ha. Promisingly, 17i (K_i = 6.7 nM) was 6 and 4 times more potent than flumioxazin (K_i = 46 nM) and trifludimoxazin (K_i = 31 nM), respectively. Moreover, 17i displayed excellent, broad-spectrum herbicidal activity, even at levels as low as 37.5 g ai/ha, and it was determined to be safe for wheat at 150 g ai/ha in postemergent application, indicating the great potential for 17i development as a herbicide for weed control in wheat fields.

  DOI：

  10.1021/acs.jafc.9b02996
• 作为产物：
  描述：

  三光气 、 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine
  参考文献：
  名称：

  Design, Herbicidal Activity, and QSAR Analysis of Cycloalka[d]quinazoline-2,4-dione–Benzoxazinones as Protoporphyrinogen IX Oxidase Inhibitors

  摘要：

  In continuation of our search for potent protoporphyrinogen IX oxidase (PPO, EC 1.3.3.4) inhibitors, we designed and synthesized a series of novel herbicidal cycloalka[d]quinazoline-2,4-dione-benzoxazinones. The bioassay results of these synthesized compounds indicated that most of the compounds exhibited very strong Nicotiana tabacum PPO (NtPPO) inhibition activity. More than half of the 37 synthesized compounds displayed over 80% control of all three tested broadleaf weeds at 37.5-150 g ai/ha by postemergent application, and a majority of them showed no phytotoxicity toward at least one kind of crop at 150 g ai/ha. Promisingly, 17i (K_i = 6.7 nM) was 6 and 4 times more potent than flumioxazin (K_i = 46 nM) and trifludimoxazin (K_i = 31 nM), respectively. Moreover, 17i displayed excellent, broad-spectrum herbicidal activity, even at levels as low as 37.5 g ai/ha, and it was determined to be safe for wheat at 150 g ai/ha in postemergent application, indicating the great potential for 17i development as a herbicide for weed control in wheat fields.

  DOI：

  10.1021/acs.jafc.9b02996

文献信息

• Heterocyclic substituted uracil derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US05232898A1

  公开（公告）日：1993-08-03

  The invention is concerned with compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, n and X have the significances given in the description, as well as enol ethers and salts thereof and their manufacture. The compounds have herbicidal properties and are accordingly suitable as active ingredients of weed control compositions. The invention is also concerned with weed control compositions containing one or more of such substances as well as the use of the substances or compositions for the control of weeds. Certain starting materials, which also have herbicidal activity, and their production are also described.

  这项发明涉及以下结构的化合物##STR1##其中R.sup.1、R.sup.2、R.sup.3、R.sup.4、R.sup.5、R.sup.6、R.sup.7、n和X的含义如描述中所示，以及烯醚及其盐和制备方法。这些化合物具有除草特性，因此适用作为除草剂配方的活性成分。该发明还涉及含有一种或多种这类物质的除草剂配方，以及利用这些物质或配方控制杂草。还描述了具有除草活性的某些起始材料及其生产。
• N-phenylimides, and their production and use
  申请人：Sumitomo Chemical Company, Limited

  公开号：US05322835A1

  公开（公告）日：1994-06-21

  A compound of the formula: ##STR1## wherein X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or a fluorine atom, Z is a methylene group or a group of the formula: N--R.sub.5 (in which R.sub.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group), R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group, a halo(C.sub.3 -C.sub.7)alkenyl group, a cyano(C.sub.1 -C.sub.6)alkyl group, a C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sub.3 and R.sub.4 are, the same or different, each is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; n is an integer of 0 or 1, which is useful as a herbicide.

  一种化合物的公式为：##STR1## 其中X是氧原子或硫原子，Y是氢原子或氟原子，Z是亚甲基基团或公式：N--R.sub.5（其中R.sub.5是氢原子、C.sub.1 -C.sub.6烷基基团、C.sub.3 -C.sub.7烯基基团、C.sub.3 -C.sub.7炔基基团、卤代（C.sub.2 -C.sub.6）烷基基团或C.sub.1 -C.sub.6烷氧羰基甲基基团），R.sub.1是氢原子、C.sub.1 -C.sub.6烷基基团、C.sub.3 -C.sub.7烯基基团、C.sub.3 -C.sub.7炔基基团、卤代（C.sub.2 -C.sub.6）烷基基团、卤代（C.sub.3 -C.sub.7）烯基基团、氰基（C.sub.1 -C.sub.6）烷基基团、C.sub.1 -C.sub.6烷氧基（C.sub.1 -C.sub.6）烷基基团或C.sub.1 -C.sub.6烷氧羰基甲基基团，R.sub.2是氢原子或C.sub.1 -C.sub.6烷基基团；R.sub.3和R.sub.4是相同或不同，每个是氢原子或C.sub.1 -C.sub.6烷基基团；n是0或1的整数，用作除草剂。
• Herbicidal N-phenyl-substituted oxazinediones and oxazinonethiones
  申请人：Bayer Aktiengesellschaft

  公开号：US05061310A1

  公开（公告）日：1991-10-29

  Combating unwanted vegetation with N-phenyl-substituted oxazinediones of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 can each be hydrogen or an organic radical or R.sup.2 and R.sup.3 and/or R.sup.6 and R.sup.7 can form a ring, and Q is oxygen or sulphur. Those compounds are new wherein at least three of the radicals R.sup.1 to R.sup.5 are other than hydrogen or the two radicals R.sup.2 and R.sup.3 together represent --O--CH.sub.2 --O--CH.sub.2 -- or the group --X--(CO).sub.n --A--Y--.

  使用N-苯基取代的氧杂环己二酮化合物对抗不受欢迎的植物，其化学式为##STR1##其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，R.sup.6和R.sup.7每个可以是氢或有机基团，或者R.sup.2和R.sup.3和/或R.sup.6和R.sup.7可以形成环，Q是氧或硫。这些化合物是新的，其中至少三个基团R.sup.1到R.sup.5不是氢，或者两个基团R.sup.2和R.sup.3一起代表--O--CH.sub.2--O--CH.sub.2--或者基团--X--(CO).sub.n--A--Y--。
• Heterocyclic compounds
  申请人：Nihon Tokushu Noyaku Seizo K.K.

  公开号：US05034051A1

  公开（公告）日：1991-07-23

  Herbicidal compounds of the formula ##STR1## in which X denotes an oxygen atom or sulfur atom, Y denotes a hydrogen atom or halogen atom, Z denotes an oxygen atom or sulfur atom, n denotes 0 to 1, and R denotes hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms or an alkynyl group having 2 to 4 carbon atoms. Intermediates of the formula ##STR2## are also new.

  化学式为##STR1##的除草剂化合物，其中X表示氧原子或硫原子，Y表示氢原子或卤素原子，Z表示氧原子或硫原子，n表示0到1，R表示氢、具有1到6个碳原子的烷基、具有2到4个碳原子的烯基或具有2到4个碳原子的炔基。化学式为##STR2##的中间体也是新的。
• N-Phenylimides, and their production and use
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0338533A2

  公开（公告）日：1989-10-25

  A compound of the formula I: wherein X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or a fluorine atom, Z is an oxygen atom, a methylene group or a group of the formula: N-Rs (in which Rs is a hydrogen atom, a C1-C6 alkyl group, a C3-C7 alkenyl group, a C3-C7 alkynyl group, a halo(C2-C6)alkyl group or a C1-C6 alkoxycarbonylmethyl group), R, is a hydrogen atom, a C1-C6 alkyl group, a C3-C7 alkenyl group, a C3-C7 alkynyl group, a halo(C alkyl group, a halo(C3-C7)alkenyl group, a cyano(C1-C6)alkyl group, a C1-C6 alkoxy(C1-C6)alkyl group or a C1-C6 alkoxycarbonylmethyl group, R2 is a hydrogen atom or a C1-C6 alkyl group; R3 and R4 are, the same or different, each a hydrogen atom or a C1-C6 alkyl group; n is an integer of 0 or 1, which is useful as a herbicide.

  式 I 的化合物 其中 X 是氧原子或硫原子，Y 是氢原子或氟原子，Z 是氧原子、亚甲基或式中的基团：N-Rs（其中 Rs 是氢原子、C1-C6 烷基、C3-C7 烯基、C3-C7 炔基、卤代（C2-C6）烷基或 C1-C6 烷氧羰基甲基），R, 是氢原子、C1-C6 烷基、C3-C7 烯基、C3-C7 炔基、卤代（C2-C6）烷基或 C1-C6 烷氧羰基甲基、C3-C7炔基、卤代(C-烷基)、卤代(C3-C7)烯基、氰基(C1-C6)烷基、C1-C6烷氧基(C1-C6)烷基或C1-C6烷氧基羰基甲基，R2是氢原子或C1-C6烷基；R3 和 R4 相同或不同，各自为氢原子或 C1-C6 烷基；n 为 0 或 1 的整数，可用作除草剂。