苯(甲)醛,2-[(4,6-二甲氧基-2-嘧啶基)氧代]- | 110284-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯(甲)醛,2-[(4,6-二甲氧基-2-嘧啶基)氧代]-
• 英文名称: 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)benzaldehyde
• 英文别名: 2-(4,6-dimethoxypyrimidine-2-oxy)benzaldehyde；2-(2-formylphenoxy)-4,6-dimethoxypyrimidine；2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde；Benzaldehyde, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-；2-(4,6-dimethoxypyrimidin-2-yl)oxybenzaldehyde
• CAS: 110284-76-9
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: OLJJNJSCMNETTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  70.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯(甲)醛,2-[(4,6-二甲氧基-2-嘧啶基)氧代]- 在 苯肼 作用下， 以 甲苯 为溶剂， 生成 2-(4,6-dimethoxy-pyrimidin-2-yl-oxy)-benzaldehyde phenylhydrazone
  参考文献：
  名称：

  Herbicidal substituted azines

  摘要：

  该公式表示的除草剂替代嘧啶类化合物，其中m代表数字0、1、2或3，A代表氮或C-X基团，其中X代表氢或卤素，Q代表氧或硫，R.sup.1和R.sup.2相同或不同，代表氢、卤素、烷基、卤代烷基、烷氧基-烷基、烷氧基、卤代烷氧基、烷基硫、烷基氨基或二烷基氨基，R.sup.3代表氨基、羟基、卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、烷基氨基、二烷基氨基、烷基羰胺基、烷氧羰基氨基或烷基磺酰氨基，R.sup.4代表氢或烷基，Z代表N-R.sup.5或另一个结构。

  公开号：

  US05167693A1
• 作为产物：
  描述：

  4,6-二甲氧基-2-甲硫基嘧啶 在 sodium tungstate 、 双氧水 、 potassium carbonate 作用下， 以 溶剂黄146 、 丁酮 为溶剂， 反应 3.0h， 生成 苯(甲)醛,2-[(4,6-二甲氧基-2-嘧啶基)氧代]-
  参考文献：
  名称：

  Dimethoxypyrimidines as Novel Herbicides. Part 2. Synthesis and Herbicidal Activity ofO-Pyrimidinylsalicylates and Analogues

  摘要：

  A new series of the O-pyrimidinylsalicylates was synthesized and their herbicidal activity was examined. Some of these compounds showed very strong herbicidal activity under pre- and post-emergent treatment conditions against various kinds of grass and broadleaf weeds. Among these compounds, O-(4, 6-dimethoxypyrimidin-2-yl) salicylic acid and its methyl ester were found to exhibit the highest activity. The herbicidal symptoms observed after the treatments included early cessation of plant growth followed by chlorosis, necrosis and plant death. The symptoms were similar to those caused by sulfonylureas and imidazolinones, which inhibit branched-chain amino acid biosynthesis.

  DOI：

  10.1002/(sici)1096-9063(199606)47:2<115::aid-ps397>3.0.co;2-r

文献信息

• Cyano-containing pyrimidine derivatives and their use as herbicides
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP0643048A2

  公开（公告）日：1995-03-15

  The present invention relates to novel cyano-containing pyrimidine derivatives of the general formula (I) wherein R1 represents halogen, C1-4-alkyl, C1 -4-alkoxy, halogeno-C, -4-alkyl, or halogeno-C1-4-alkoxy, R2 represents halogen, C1-4-alkoxy, halogeno-C1-4-alkyl, or halogeno-C1-4-alkoxy, R3 represents halogen, hydroxy, or an oxo group formed together with R4 or R3 represents one of the following groups represented by and-O-S02-R6, R4 represents hydrogen or an oxo group formed together with R3, R5 represents hydrogen or in each case an optionally substituted or unsubstituted C1-20 -alkyl, C2-20- alkenyl, C2-2o-alkynyl, C1-4-alkoxycarbonyl, C3-7-cycloalkyl, or carboxyl or phenyl, R5 represents an optionally substituted or unsubstituted five- or six-membered heterocyclic ring, or an optionally substituted bicyclic group formed by condensation of a five or six-membered heterocyclic ring with phenyl, and R6 represents in each case an optionally substituted or unsubstituted C1-20-alkyl, C2-2o-alkenyl, C2-20- alkynyl or phenyl; to processes for their preparation and to their use as herbicides.

  本发明涉及一般式(I)的新型含氰基嘧啶衍生物， 其中 R1代表卤素，C1-4-烷基，C1-4-烷氧基，卤代C1-4-烷基，或卤代C1-4-烷氧基， R2代表卤素，C1-4-烷氧基，卤代C1-4-烷基，或卤代C1-4-烷氧基， R3代表卤素，羟基，或与R4一起形成的氧代基， R3代表以下所示的一种基团之一 和-O-SO2-R6， R4代表氢或与R3一起形成的氧代基， R5代表氢或分别是一个可选择取代或未取代的C1-20-烷基，C2-20-烯基，C2-20-炔基，C1-4-烷氧羰基，C3-7-环烷基，或羧基或苯基， R5代表一个可选择取代或未取代的五元或六元杂环，或由五元或六元杂环与苯环缩合形成的可选择取代的双环基团，以及 R6代表分别是一个可选择取代或未取代的C1-20-烷基，C2-20-烯基，C2-20-炔基或苯基； 以及它们的制备方法和作为除草剂的用途。
• 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldoximes, preparation processes
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US04986846A1

  公开（公告）日：1991-01-22

  Disclosed are herbicidally active pyrimidine derivatives of the formula ##STR1## wherein R represents a hydrogen atom or an etherifying group, e.g., a lower alkyl, lower alkenyl, lower alkynyl, phenyl-substituted lower alkenyl, lower haloalkenyl, cycloalkyl, substituted phenyl-substituted lower alkenyl or phenyl-substituted lower alkynyl group; or a group represented by the following formula: ##STR2## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group, X a halogen atom or a lower alkyl or lower alkoxyl group, m and n individually 0-2, and when m is 2, both Xs may be the same or different, and herbicidal compositions containing the same, alone or in combination with another herbicidally active compound, the pyrimidine derivatives being prepared by reaction of 2-(4,6-dimethoxy-2-pyrimidinyloxy)benzaldehyde with NH.sub.2 OR or with a salt of hydroxylamine followed by reaction with a halide of the formula RY wherein R has the same value as above and Y is Cl, Br or I.

  揭示了具有以下式的除草活性嘧啶衍生物##STR1##其中R代表氢原子或醚化基团，例如，较低的烷基，较低的烯基，较低的炔基，苯基取代的较低烯基，较低的卤代烯基，环烷基，取代的苯基取代的较低烯基或苯基取代的较低炔基；或由以下式表示的基团：##STR2##其中R.sup.1代表氢原子或较低的烷基，X代表卤原子或较低的烷基或较低的烷氧基，m和n分别为0-2，当m为2时，两个X可能相同或不同，并且含有这些衍生物的除草组合物，单独或与另一种除草活性化合物结合使用，所述嘧啶衍生物通过2-(4,6-二甲氧基-2-嘧啶氧基)苯甲醛与NH.sub.2 OR或与羟胺盐反应，然后与具有上述相同值的R的卤化物RY反应，其中Y为Cl，Br或I制备而成。
• Synthesis and Biological Activity Evaluation of Novel α-Amino Phosphonate Derivatives Containing a Pyrimidinyl Moiety as Potential Herbicidal Agents
  作者：Jin-Long Chen、Wu Tang、Jian-Yi Che、Kai Chen、Gang Yan、Yu-Cheng Gu、De-Qing Shi

  DOI：10.1021/acs.jafc.5b02335

  日期：2015.8.19

  I exhibited good herbicidal activities; for example, the activities of compounds Ib, Ic, Ig, Ii, Ik, and Im were as good as the positive control herbicides (acetochlor, atrazine, mesotrione, and glyphosate). However, their structural isomers II and III and analogues IV did not display any herbicidal activities in vivo, although some of them possessed selective inhibitory activity against Arabidopsis

  为了找到具有新颖除草作用方式的新型高活性和低毒性除草剂先导化合物，由路易斯酸设计并合成了一系列含有嘧啶基部分I，II，III和IV的新型α-氨基膦酸酯衍生物（高氯酸镁）催化的醛，胺和亚磷酸酯的曼尼希型反应。通过光谱数据（IR，1 H NMR，31 P NMR，EI-MS）和元素分析清楚地鉴定了它们的结构。生物测定[体外，体内（GH1和GH2）]表明，大多数化合物I表现出良好的除草活性。例如，化合物Ib，Ic的活性，Ig，Ii，Ik和Im与阳性对照除草剂（乙草胺，阿特拉津，甲基磺草酮和草甘膦）一样好。然而，尽管它们中的一些具有体外对拟南芥的选择性抑制活性，但它们的结构异构体II和III和类似物IV在体内没有任何除草活性。有趣的是，发现化合物IVs，IVt和IVl对蚜虫或小菜蛾具有选择性的杀虫活性。， 分别。他们还初步研究了除草剂的作用方式和结构-活性关系。
• Synthesis, crystal structure, and herbicidal activity of pyrimidinyl benzylamine analogues containing a phosphonyl group
  作者：Wu Tang、Zhi-Hua Yu、De-Qing Shi

  DOI：10.1002/hc.20589

  日期：——

  A series of pyrimidinyl benzylamine analogues containing a phosphonyl group (2) was synthesized via the Mannich-type reactions of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoaldehyde 1, aromatic amines, and dialkyl phosphites or triphenyl phosphite in the presence of Mg(ClO4)2. Their structures were characterized by spectroscopic data (infrared, 1H NMR, 31P NMR, and mass spectrometry) and elemental analyses

  通过 2-(4,6-二甲氧基嘧啶-2-基氧基)苯甲醛 1、芳香胺和亚磷酸二烷基酯或亚磷酸三苯酯的曼尼希型反应合成了一系列含有膦酰基 (2) 的嘧啶基苄胺类似物Mg(ClO4)2。它们的结构通过光谱数据（红外、1H NMR、31P NMR 和质谱）和元素分析表征，化合物 2b 进一步通过 X 射线衍射晶体学确定。初步生物测定（体外）的结果表明，大多数标题化合物2对双子叶杂草（Brassica campestris L.）表现出比单子叶杂草（Echinochloa crus-galli）更高的除草活性。进一步的生物测定（体内）表明，在 1.5 kg/ha 的芽前和芽后处理中，2 中的一些显示出与市售除草剂 Bispyribac-sodium 一样好的对苋菜（Amaranthus retroflexus）的除草活性。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:148–155
• Synthesis and Herbicidal Activity of <i>α</i> ‐Hydroxy Phosphonate Derivatives Containing Pyrimidine Moiety
  作者：Hong Song、Huiyu Mao、Deqing Shi

  DOI：10.1002/cjoc.201090337

  日期：2010.10

  A series of α‐hydroxy phosphonate derivatives containing pyrimidine moiety were designed and synthesized. Their structures were characterized by IR, 1H NMR, MS and elemental analysis. The results of preliminary herbicidal activities (in vitro) showed that some of the title compounds 2 exhibited moderate herbicidal activities against dicotyledonous weeds (Brassica campestris L), and most of compounds

  设计并合成了一系列含有嘧啶部分的α-羟基膦酸酯衍生物。通过IR，1 H NMR，MS和元素分析对它们的结构进行了表征。初步除草活性（体外）的结果表明，某些标题化合物2对双子叶杂草（芸苔属L）表现出中等的除草活性，大多数化合物2对双子叶杂草的抑制作用均比单子叶杂草（棘刺E））。进一步的生物测定（体内）表明某些标题化合物2在芽前和芽后剂量为1.5 kg / ha的处理中，a菜具有良好的选择性除草活性。例如，化合物2a，2b和2e在出苗前处理中表现出对逆反射曲霉的100％抑制作用，在出苗后处理中以1.5 kg / ha的剂量分别表现出91.7％，98.8％和99.5％的抑制作用。