1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟丁烷-1,3-二酮 | 177211-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟丁烷-1,3-二酮
• 英文名称: 1-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-4,4,4-trifluoro-1,3-butanedione
• 英文别名: 1,3-Butanedione, 1-(4-chloro-2-fluoro-5-methylphenyl)-4,4,4-trifluoro-；1-(4-chloro-2-fluoro-5-methylphenyl)-4,4,4-trifluorobutane-1,3-dione
• CAS: 177211-21-1
• 化学式: C₁₁H₇ClF₄O₂
• 分子量: 282.622
• InChiKey: MKHDLSGGKWVJRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟丁烷-1,3-二酮 在 肼 作用下， 以 甲苯 为溶剂， 反应 9.0h， 生成 1-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-1-methyl-5-(trifluoromethyl)-1H-pyrazole
  参考文献：
  名称：

  The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat

  摘要：

  JV 485 [C-14-Ph] and JV 485 [C-14-Py] were synthesized in seven steps in 35% and 44% overall yields, respectively, utilizing the same reaction schemes. The key step in each of the syntheses is a one pot Mid-Century Oxidation (I) of an aromatic methyl group to a carboxylic acid. The C-14 radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Preparation of the JV 485 [phenyl-C-14(U)] amide was completed in 62% yield from 2-chloro-5-14-bromo-1-methyl-5-trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid [ring-C-14(U)], (9) over bar. Preparation of the JV 485 [phenyl-C-14(U)] desmethyl acid <(13)over bar> was accomplished in 18% overall yield in four steps from 3-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-5-(trifluoromethyl)1H-pyrazole, (4) over bar.

  DOI：

  10.1002/1099-1344(200006)43:7<645::aid-jlcr349>3.0.co;2-6
• 作为产物：
  描述：

  2-氯-4-氟甲苯 在 三氯化铝 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 1-(4-氯-2-氟-5-甲基苯基)-4,4,4-三氟丁烷-1,3-二酮
  参考文献：
  名称：

  The radiolabeled syntheses of JV 485, a herbicide candidate for winter wheat

  摘要：

  JV 485 [C-14-Ph] and JV 485 [C-14-Py] were synthesized in seven steps in 35% and 44% overall yields, respectively, utilizing the same reaction schemes. The key step in each of the syntheses is a one pot Mid-Century Oxidation (I) of an aromatic methyl group to a carboxylic acid. The C-14 radiolabeled syntheses of two isolated metabolites of JV 485 were also completed. Preparation of the JV 485 [phenyl-C-14(U)] amide was completed in 62% yield from 2-chloro-5-14-bromo-1-methyl-5-trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzoic acid [ring-C-14(U)], (9) over bar. Preparation of the JV 485 [phenyl-C-14(U)] desmethyl acid <(13)over bar> was accomplished in 18% overall yield in four steps from 3-(4-chloro-2-fluoro-5-methylphenyl [ring-14C(U)])-5-(trifluoromethyl)1H-pyrazole, (4) over bar.

  DOI：

  10.1002/1099-1344(200006)43:7<645::aid-jlcr349>3.0.co;2-6

文献信息

• Synthesis, structures, and herbicidal activity of isoxazole derivatives
  作者：Yuhan Zhou、Yanhui Chen、Weirong Miao、Jingping Qu

  DOI：10.1002/jhet.475

  日期：2010.11

  phenyl‐butan‐1,3‐dione. Their structures were confirmed by element analysis, IR, MS, and 1H NMR. X‐ray structure analysis indicated that the dihedral angles of the phenyl ring with the isoxazole ring in compounds 4a and 4b were 19.46° and 49.18°, respectively. Preliminary bioassay showed that the title compounds had good activity to various weeds, and 4a exhibited almost the same activity with 4b. This was different

  几种新颖的3-取代的苯基异恶唑衍生物是由取代的苯基-丁丹-1,3-二酮制得的。通过元素分析，IR，MS和1 H NMR确认了它们的结构。X射线结构分析表明，化合物4a和4b中苯环与异恶唑环的二面角分别为19.46°和49.18°。初步的生物分析表明，标题化合物对各种杂草均具有良好的活性，而4a的活性几乎与4b相同。这与以前的研究不同，后者表明具有杂环部分的苯环的大二面角对于高除草活性是必需的。J.杂环化​​学。（2010）。
• [DE] SUBSTITUIERTE 3-PHENYLISOXAZOLINE<br/>[EN] SUBSTITUTED 3-PHENYL ISOXAZOLINES<br/>[FR] 3-PHENYLISOXAZOLINE SUBSTITUEE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1999005130A1

  公开（公告）日：1999-02-04

  (DE) Substituierte 3-Phenylisoxazoline der Formel (I), deren Salze und Enolether als Herbizide, wobei X = -O-, -S-, -N(R9)-; R1 = CN, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Halogenalkoxy, C1-C4-Alkylsulfonyl; R2 = H oder gegebenenfalls substituiertes C1-C6-Alkyl, (C1-C6-Alkyl)carbonyl, C1-C6-Alkylsulfonyl, C2-C6-Alkenyl, (C2-C6-Alkenyl)carbonyl, C2-C6-Alkinyl, (C2-C6-Alkinyl)-carbonyl; R3 = H, Halogen; R4 = CN, Halogen, C1-C3-Halogenalkyl; R5 = H, CN, Halogen, C1-C3-Halogenalkyl; R6 = H, CN, Halogen, C1-C3-Halogenalkyl oder gegebenenfalls subst. C1-C6-Alkoxy; R7 = CN, Halogen; R8 an $g(a), wobei R7 dann an $g(b) steht, oder an $g(b), wobei R7 dann an $g(a) steht; 1) H, OH, SH, CN, NO2, Halogen, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Halogenalkoxy, C1-C6-Halogenalkylthio, C1-C6-Alkylthio-(C1-C6-alkyl)-carbonyl, (C1-C6-Alkyl)iminooxycarbonyl, C1-C6-Alkoxy-C1-C6-alkyl, C1-C6-Alkoxyamino-C1-C6-alkyl, C1-C6-Alkoxy-C1-C6-alkylamino-C1-C6-alkyl, 2) gegebenenfalls substituiertes C1-C6-Alkoxy, C1-C6-Alkylthio, C3-C6-Cycloalkoxy, C3-C6-Cycloalkylthio, C2-C6-Alkenyloxy, C2-C6-Alkenylthio, C2-C6-Alkinyloxy, C2-C6-Alkinylthio, (C1-C6-Alkyl)carbonyloxy, (C1-C6-Alkyl)carbonylthio, (C1-C6-Alkoxy)carboxyloxy, (C2-C6-Alkenyl)carbonyloxy, (C2-C6-Alkenyl)carbonylthio, (C2-C6-Alkinyl)carbonyloxy, (C2-C6-Alkinyl)carbonylthio, C1-C6-Alkylsulfonyloxy oder C1-C6-Alkylsulfonyl, 3) 29 weitere Reste; R9 = H, C1-C6-Alkyl, C3-C6-Cycloalkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C6-Alkoxy-C1-C6-alkyl, (C1-C6-Alkoxy)carbonyl-C1-C6-alkyl, (C3-C6-Alkenyloxy)carbonyl-C1-C6-alkyl, gegebenenfalls substituiertes Phenyl oder Phenyl-C1-C6-alkyl.(EN) The invention relates to substituted 3-phenyl isoxazolines of formula (I) and salts and enol ethers thereof, and to their use as herbicides. In said formula (I), X represents -O-, -S-, -N(R9)-; R1 represents CN, C1-C4alkyl, C1-C4alkyl halide, C1-C4halogen alkoxy, C1-C4alkyl sulfonyl; R2 represents H or optionally, substituted C1-C6 alkyl, (C1-C6 alkyl) carbonyl, C1-C6alkyl sulfonyl, C2-C6 alkenyl, (C2-C6 alkenyl) carbonyl, C2-C6alkinyl, (C2-C6alkinyl) carbonyl; R3 represents H, halogen; R4 represents CN, halogen, C1-C3 alkyl halide; R5 represents H, CN, halogen, C1-C3alkyl halide; R6 represents H, CN, halogen, C1-C3 alkyl halide or optionally, substituted C1-C6 alkoxy; R7 represents CN, halogen; R8 is at $g(a) when R7 is at $g(b), or at $g(b) when R7 is at $g(a) and represents: 1) H, OH, SH, CH, NO2, halogen, C1-C6alkyl, C1-C6alkyl halide, C1-C6halogen alkoxy, C1-C6 halogenalkylthio, C1-C6 alkylthio (C1-C6alkyl) carbonyl, (C1-C6 alkyl) iminooxycarbonyl, C1-C6alkoxy C1-C6alkyl, C1-C6alkoxyamino C1-C6alkyl, C1-C6alkoxy C1-C6alkylamino C1-C6alkyl, 2) optionally, substituted C1-C6alkoxy, C1-C6 alkylthio, C3-C6 cycloalkoxy, C3-C6 cycloalkylthio, C2-C6 alkenyloxy, C2-C6alkenylthio, C2-C6 alkinyloxy, C2-C6 alkinylthio, (C1-C6 alkyl) carbonyloxy, (C1-C6 alkyl) carbonylthio, (C1-C6 alkoxy) carboxyloxy, (C2-C6 alkenyl) carbonyloxy, (C2-C6 alkenyl) carbonylthio, (C2-C6 alkinyl) carbonyloxy, (C2-C6 alkinyl) carbonylthio, C1-C6 alkylsulfonyloxy or C1-C6 alkylsulfonyl and 3) 29 other radicals; and R9 represents H, C1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 alkenyl, C3-C6 alkinyl, C1-C6 alkoxy C1-C6alkyl, (C3-C6 alkenyloxy) carbonyl C1-C6alkyl and optionally, substituted phenyl or phenyl C1-C6alkyl.(FR) L'invention concerne des 3-phénylisoxazoline substituées représentés par la formule (I), ainsi que les sels et enoléthers de ces dernières, utilisés comme herbicides. Dans la formule (I), X = -O-, -S-, -N(R9)-; R1 = CN, alkyle C1-C4, halogénalkyle C1-C4, halogénalkoxy C1-C4, Alkylsulfonyle C1-C4; R2 = H ou éventuellement alkyle C1-C6, (alkyl C1-C6)carbonyle, alkylsulfonyle C1-C6, alcényle C2-C6, (alcényl C2-C6)carbonyle, alcynyle C2-C6, (alcynyl C2-C6)carbonyle; R3 = H, halogène; R4 = CN, halogène, halogénalkyle C1-C3; R5 = H, CN, halogène, halogénalkyle C1-C3, R6 = H, CN, halogène, halogénalkyle C1-C3 ou éventuellement alkoxy C1-C6 substitué; R7 = CN, halogène; R8 est en $g(a), lorsque R7 est en $g(b), ou R8 est en $g(b) lorsque R7 est en $g(a): 1) H, OH, SH, CN, NO2, halogène, alkyle C1-C6, halogénalkyle C1-C6, halogénalcoxy C1-C6, halogénalkylthio C1-C6, alkylthio C1-C6-(alkyl C1-C6)-carbonyle, (alkyl C1-C6)imino-oxycarbonyle, alcoxy C1-C6-alkyle C1-C6, alcoxy C1-C6-amino-alkyle C1-C6, alcoxy C1-C6-alkylamino-alkyle C1-C6, 2) éventuellement alcoxy C1-C6, alkylthio C1-C6, cycloalkoxy C3-C6, cycloalkylthio C3-C6, alcényloxy C2-C6, alcénylthio C2-C6, alcynyloxy C2-C6, alcynylthio C2-C6, (alkyl C1-C6)carbonyloxy, (alkyl C1-C6)carbonylthio, (alkoxy C1-C6)carboxyloxy, (alcényl C2-C6)carbonyloxy, (alcényl C2-C6)carbonylthio, (alcynyl C2-C6)carbonyloxy, (alcynyl C2-C6)carbonylthio, alkylsulfonyloxy C1-C6 ou Alkylsulfonyl C1-C6 substitués, 3) 29 groupes additionnels; R9 = H, alkyle C1-C6, cycloalkyle C3-C6, alcényle C3-C6, alcynyle C3-C6, alkoxy C1-C6-alkyle C1-C6, (alkoxy C1-C6)carbonyl-alkyle C1-C6, (alcényloxy C3-C6)carbonyle-alkyle C1-C6, éventuellement phényle substitué ou phényl-alkyle C1-C6.

  这是一项涉及3-苯并噻吩取代物及其盐和甲基醚的发明，用于化学除草剂的使用。在该公式中，X代表-O-、-S-、-N(R9)-；R1代表CN、1-4号碳链基团、1-4号碳链基团含卤素、1-4号碳链基团含氧、1-4号碳链基团硫基；R2代表H或可选的1-6号碳链基团、1-6号碳链基团碳骨架、1-6号碳链基团硫基、2-6号烯基、2-6号烯基碳骨架、2-6号氮烯基、2-6号氮烯基碳骨架；R3代表H、卤素；R4代表CN、卤素、1-3号碳链含卤素；R5代表H、CN、卤素、1-3号碳链含卤素；R6代表H、CN、卤素、1-3号碳链含卤素或可选的1-6号氧杂基团；R7代表CN、卤素；R8位于Rb(g)(a)，当R7位于Rb(g)(b)时，或位于Rb(g)(b)，当R7位于Rb(g)(a)时。1) H、OH、SH、CN、NO2、卤素、1-6号碳链基团、1-6号碳链含卤素、1-6号碳氧含卤素基团、1-6号碳链硫基、1-6号碳链硫基碳骨架、1-6号氧杂基团碳链、1-6号氧杂基团碳链碳骨架、1-6号碳链硫基氧杂基团、1-6号氧杂基团碳链、1-6号氧杂基团碳链碳骨架、1-6号硫代碳链基团、1-6号硫代碳链基团；2)可选的1-6号氧杂基团、1-6号硫代碳链基团、3-6号环烷氧基、3-6号环烷硫代基团、2-6号烯氧基、2-6号烯硫代基团、2-6号键碱氧基、2-6号键碱硫代基团、1-6号碳链酸氧基、2-6号烯氧碳骨架、2-6号烯硫代基团、2-6号键碱氧碳骨架、2-6号键碱硫代碳骨架、1-6号碳链硫基氧、1-6号碳链硫基硫；3) 29个其他基团；R9代表H、1-6号碳链基团、3-6号环烷基团、3-6号烯基、3-6号键碱基团、1-6号氧杂基团碳链基团、3-6号烯基氧骨架碳骨架、可选的苯基或苯基1-6号碳链基团。
• [EN] PHENYLISOXAZOLINE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ DE PHÉNYLISOXAZOLINE ET SON UTILISATION<br/>[ZH] 一种苯基异恶唑啉类化合物及其用途
  申请人：SHENYANG SINOCHEM AGROCHEMICALS R & D CO LTD

  公开号：WO2021082901A1

  公开（公告）日：2021-05-06

  提供了一种苯基异恶唑啉类化合物及其用途。苯基异恶唑啉类化合物如通式(I)所示，通式(I)化合物具有很好的除草活性，可以有效地控制稗草、狗尾草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆等杂草，在低剂量下就可以获得很好的除草效果，且对作物如玉米、小麦、水稻等具有一定的安全性，在农业上可用作除草剂。
• BENZOYL DERIVATIVES AND SYNTHESIS THEREOF
  申请人：MONSANTO COMPANY

  公开号：EP0772580A1

  公开（公告）日：1997-05-14
• SUBSTITUIERTE 3-PHENYLISOXAZOLINE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0998468A1

  公开（公告）日：2000-05-10