1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one | 119162-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one
• 英文别名: 1-(2-Fluoro-4-hydroxyphenyl)-3-methyl-4-(difluoromethyl)-1H-1,2,4-triazol-5(4H)-one；4-(difluoromethyl)-2-(2-fluoro-4-hydroxyphenyl)-5-methyl-1,2,4-triazol-3-one
• CAS: 119162-25-3
• 化学式: C₁₀H₈F₃N₃O₂
• 分子量: 259.188
• InChiKey: HMNHUAILZMXURR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one 在 吡啶 、 硫酸 、 水 、 硝酸 、 铁粉 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 N-[2-(4-Chloro-benzyloxy)-5-(4-difluoromethyl-3-methyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-4-fluoro-phenyl]-methanesulfonamide
  参考文献：
  名称：

  Structure-Activity Relationships of Herbicidal Aryltriazolinones

  摘要：

  A series of substituted aryltriazolinones, known to inhibit protoporphyrinogen oxidase, were prepared and their structure-activity requirements at positions 4 and 5 of the aromatic ring investigated. A QSAR equation obtained for substituents at the 5 position identified the hydrophobicity term pi and the Sterimol minimum width B-1 as the two parameters affecting in-vitro biological activity. Greenhouse pre-emergence activity correlated with in-vitro activity and the hydrophobicity term pi of the substituent at that position. It was found that the phenoxy-4-oxyacetate group at aromatic position 5 was an outlier and had to be considered separately. SAR analysis of substituents at aromatic position 4 revealed that two different models were required to explain all observed substituent effects. In the first model, where the 5 position was occupied by hydrogen, the 4-chlorobenzyloxy group at aromatic position 4 gave the best compound. The second model, where the 5 position of the aromatic ring was occupied by a group other than hydrogen, resulted in a OSAR equation, previously derived, which links substituent effects at position 4 with pi and with the electronic para inductive term F-p. In this model the chloro group provides optimum biological activity. The need to separate the aryltriazolinone herbicides into several different classes in order to explain their substituent effects at aromatic positions 4 and 5 could be rationalized if more than one binding conformation, within the same binding site, is possible.

  DOI：

  10.1002/(sici)1096-9063(199708)50:4<283::aid-ps600>3.0.co;2-l
• 作为产物：
  描述：

  1-(4-amino-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one 、 sodium nitrite 在 Copper sulfate pentahydrate 、 (hexaaqua)iron(II) sulfate monohydrate magnesium sulfate 、 乙酸乙酯 、 ethyl acetate dichloromethane 作用下， 以 硫酸 、 水 、 xylenes 为溶剂， 反应 2.0h， 以leaving 12.17 g of 1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one, m.p. 112°-114° C的产率得到1-(2-fluoro-4-hydroxyphenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-one
  参考文献：
  名称：

  Herbicidal combinations containing

  摘要：

  本发明公开了含有除草2-\x9b(4-杂环苯氧甲基)苯氧基!脂肪酸酯和其他除草剂的除草组合物。该除草2-\x9b(4-杂环苯氧甲基)苯氧基!脂肪酸酯的化学式为##STR1## 其中R'为甲基，W为氧，Q为##STR2## R为氢，M，低碳基；由3到6个碳原子组成的环烷基；低碳烯基；或低碳炔基，每个基团可以选择地被一个或多个氯或氟取代，或--\x9bCHR.sup.7 --(CH.sub.2).sub.m O!.sub.n R.sup.8 ; R.sup.1到R.sup.5各自为低碳基或低卤代碳基；R.sup.6为低碳基、低卤代碳基、低氰基-碳基、低烷氧基-碳基、低烷氧羰基-碳基、低芳基-碳基或氨基；R.sup.7为氢或甲基；R.sup.8为低碳基；X为氢、甲基、氟或氯；Y为氢；Z为氢、氟、氯、溴、低碳基或甲氧基；Z'为氢、氟或氯；Z和Z'可以一起取--(CH.sub.2).sub.4 --形成四氢萘基；m为0到2，n为1到6；M为钠、钾或铵。这些除草脂肪酸酯可与控制草类或阔叶草的除草剂一起使用。

  公开号：

  US05798316A1

文献信息

• Herbicical 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates
  申请人：FMC Corporation

  公开号：US05262390A1

  公开（公告）日：1993-11-16

  Herbicidal compounds, compositions containing them, and a method for controlling weeds by application of the compositions are disclosed. The herbicidal compounds are 2-[(4-heterocyclic(phenoxymethyl)phenoxy]alkanoates of the formula ##STR1## in which A is a derivative of an alkanoate bonded to the phenoxy oxygen at the alpha carbon, and Q is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazol-5(1H)-on-1-yl, 3,4,5,6-tetrahydrophthalimid-1-yl, 1-(1-methylethyl)imidazolidin-2,4-dion-3-yl, 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-on-1-yl, 3-chloro-4,5,6,7-tetrahydroindazol-2-yl, 4-methyl-1,2,4-triazine-3,5-dion-2-yl, 8-thia-1,6-diazabicyclo[4.3.0]nonane-7-on-9-ylimino, or 1-methyl-6-trifluoromethyl-2,4-pyrimidinedione-3-yl; X is hydrogen, fluorine, or chlorine; Y is hydrogen; W is oxygen or sulfur; Z is hydrogen, fluorine, chlorine, bromine, lower alkyl, or methoxy; Z' is hydrogen, fluorine, or chlorine; and the group AO-- may be in the 2, 3, or 4-position of the phenyl ring.

  除草化合物、含有这些化合物的组合物以及通过应用这些组合物来控制杂草的方法被披露。这些除草化合物是具有以下式子的2-[(4-杂环(苯氧甲基)苯氧基]烷酸盐：其中A是与苯氧基氧原子在α碳上键合的烷酸盐衍生物，Q是4-二氟甲基-4,5-二氢-3-甲基-1,2,4-三唑-5(1H)-酮-1-基，3,4,5,6-四氢邻苯二甲酰亚胺-1-基，1-(1-甲基乙基)咪唑啉-2,4-二酮-3-基，1,4-二氢-4-(3-氟丙基)-5H-四唑-5-酮-1-基，3-氯-4,5,6,7-四氢吲哚-2-基，4-甲基-1,2,4-三嗪-3,5-二酮-2-基，8-硫代-1,6-二氮杂双环[4.3.0]壬烷-7-酮-9-亚基，或1-甲基-6-三氟甲基-2,4-嘧啶二酮-3-基；X是氢、氟或氯；Y是氢；W是氧或硫；Z是氢、氟、氯、溴、低碳烷基或甲氧基；Z'是氢、氟或氯；而AO--基团可以位于苯环的2、3或4位。
• Herbicidal 2-[(4-heterocyclic-phenoxymethyl)phenoxy]-alkanoates
  申请人：FMC Corporation

  公开号：US05344812A1

  公开（公告）日：1994-09-06

  Herbicidal compounds, compositions containing them, and a method for controlling weeds by application of the compositions are disclosed. The herbicidal compounds are 2-[(4-heterocyclic-phenoxymethyl)phenoxy]alkanoates of the formula ##STR1## in which A is a derivative of an alkanoate bonded to the phenoxy oxygen at the alpha carbon, and Q is 4-difluoromethyl-4,5-dihydro-3-methyl-l,2,4-triazol-5(1H)-on-1-yl, 3,4,5,6-tetrahydrophthalimid-1-yl, 1-(1-methylethyl)imidazolidin-2,4-dion-3-yl, 1,4-dihydro-4-(3-fluoropropyl)-5H-tetrazol-5-on-1-yl, 3-chloro-4,5,6,7-tetrahydroindazol-2-yl, 4-methyl-l,2,4-triazine-3,5-dion-2-yl, 8-thia-1,6-diazabicyclo[4.3.0]-nonane-7-on-9-ylimino, or 1-methyl-6-trifluoromethyl-2,4-pyrimidinedione-3-yl; X is hydrogen, methyl, fluorine, or chlorine; Y is hydrogen; W is oxygen or sulfur; Z is hydrogen, fluorine, chlorine, bromine, lower alkyl, or methoxy; Z' is hydrogen, fluorine, or chlorine; and the group AO-- may be in the 2, 3, or 4-position of the phenyl ring.

  除草化合物、含有这些化合物的组合物以及通过应用这些组合物来控制杂草的方法被披露。这些除草化合物是具有以下式子的2-[(4-杂环-苯氧甲基)苯氧基]烷酸酯：##STR1## 其中A是与苯氧氧原子在α碳上结合的烷酸酯的衍生物，Q是4-二氟甲基-4,5-二氢-3-甲基-1,2,4-三唑-5(1H)-酮-1-基，3,4,5,6-四氢邻苯二甲酰亚胺-1-基，1-(1-甲基乙基)咪唑啉-2,4-二酮-3-基，1,4-二氢-4-(3-氟丙基)-5H-四唑-5-酮-1-基，3-氯-4,5,6,7-四氢吲哚-2-基，4-甲基-1,2,4-三嗪-3,5-二酮-2-基，8-硫代-1,6-二氮杂双环[4.3.0]-壬烷-7-酮-9-亚基，或1-甲基-6-三氟甲基-2,4-嘧啶二酮-3-基；X是氢、甲基、氟或氯；Y是氢；W是氧或硫；Z是氢、氟、氯、溴、低碳基或甲氧基；Z'是氢、氟或氯；以及AO--基团可能位于苯环的2、3或4位。
• Herbicidal compositions comprising
  申请人：FMC Corporation

  公开号：US05674810A1

  公开（公告）日：1997-10-07

  Herbicidal compounds, compositions containing them, and a method for controlling weeds by application of the compositions are disclosed. The herbicidal compounds are 2-\x9b(4-heterocyclic-phenoxymethyl)phenoxy!alkanoates of the formula ##STR1## in which A is a derivative of an alkanoate bonded to the phenoxy oxygen at the alpha carbon; X is hydrogen, methyl, fluorine, or chlorine; Y is hydrogen; W is oxygen or sulfur; Z is hydrogen, fluorine, chlorine, bromine, lower alkyl, or methoxy; Z' is hydrogen, fluorine, or chlorine; and the group AO-- may be in the 2, 3, or 4-position of the phenyl ring.

  本发明揭示了除草化合物、含有它们的组合物以及通过应用这些组合物控制杂草的方法。除草化合物是公式2- \ x9b（4-杂环-苯氧甲基）苯氧基！脂肪酸盐，其中A是与苯氧氧原子在α碳上结合的脂肪酸盐的衍生物；X是氢、甲基、氟或氯；Y是氢；W是氧或硫；Z是氢、氟、氯、溴、低碳基或甲氧基；Z'是氢、氟或氯；并且AO-基团可以位于苯环的2、3或4位置。
• [DE] ARYLALKYLTRIAZOLDERIVATE UND IHRE VERWENDUNG ALS HERBIZIDE<br/>[EN] ARYLALKYLTRIAZOLE DERIVATIVES AND THEIR USE AS HERBICIDES<br/>[FR] DERIVES DE TRIAZOLS D'ARYLALKYLE ET LEUR UTILISATION COMME HERBICIDES
  申请人：BAYER AKTIENGESELLSCHAFT

  公开号：WO1998032745A1

  公开（公告）日：1998-07-30

  (DE) Die Erfindung betrifft neue Arylalkylverbindungen der allgemeinen Formel (I), in welcher Q für O, S, SO oder SO2 steht, R1 für Wasserstoff oder gegebenenfalls substituiertes Alkyl steht, R2 für Wasserstoff oder gegebenenfalls substituiertes Alkyl steht, Z für eine der Gruppierungen (a), (b), (c) steht und (Y)n, (X)m, R3, R4, R5, R6, R7 und R8 für Wasserstoff oder bestimmte Substituenten stehen. Verfahren zu ihrer Herstellung, neue Zwischenprodukte sowie die Verwendung der Arylalkylverbindungen als Herbizide.(EN) The invention concerns novel arylalkyl compounds of general formula (I) in which Q stands for O, S, SO or SO2, R1 stands for hydrogen or optionally substituted alkyl, R2 stands for hydrogen or optionally substituted alkyl, Z stands for one of the groups: (a), (b), (c), and (Y)n, (X)m, R3, R4, R5, R6, R7 and R8 stand for hydrogen or given substituents. The invention also concerns processes for preparing these compounds, novel intermediate products, and the use of the arylalkyl compounds as herbicides.(FR) L'invention concerne de nouveau composés arylalkyle de la formule générale (I) dans laquelle Q désigne O, S, SO ou SO2, R1 désigne hydrogène ou alkyle éventuellement substitué, R2 désigne hydrogène ou alkyle éventuellement substitué, Z désigne un des groupes (a) (b) (c) et (Y)n, (X)m, R3, R4, R5, R6, R7 et R8 désignent hydrogène ou des substituants déterminés. L'invention concerne des procédés permettant de préparer ces composés arylalkyle, de nouveaux produits intermédiaires et leur utilisation comme herbicides.

  该发明涉及具有以下通用公式的新型苯甲基化合物，(I)其中Q代表O、S、SO或SO2, R1代表氢或可选取代的烷基，R2代表氢或可选取代的烷基，Z代表(a)、(b)、(c)中的一组，(Y)n、(X)m、R3、R4、R5、R6、R7和R8代表氢或特定的取代基。该发明还涉及这些化合物的制备方法、新型中间产物以及作为除草剂的这些苯甲基化合物的使用。
• CHANG, JUN H.;LYGA, JOHN W.
  作者：CHANG, JUN H.、LYGA, JOHN W.

  DOI：——

  日期：——