(E)-2-(2-(((1,3-二氧代异吲哚啉-2-基)氧基)甲基)苯基)-2-(甲氧基亚氨基)乙酸甲酯 | 156581-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: (E)-2-(2-(((1,3-二氧代异吲哚啉-2-基)氧基)甲基)苯基)-2-(甲氧基亚氨基)乙酸甲酯
• 英文名称: methyl (E)-α-(methoxyimino)-2-(o-phthalimidoxymethyl)benzeneacetate
• 英文别名: methyl (2E)-2-[2-[(1,3-dioxoisoindolin-2-yl)oxymethyl]phenyl]-2-methoxyiminoacetate；methyl (E)-2-(O-phthalimidoxymethyl)phenyl glyoxylate O-methyloxime；methyl (2E)-2-[2-[(1,3-dioxoisoindol-2-yl)oxymethyl]phenyl]-2-methoxyiminoacetate
• CAS: 156581-14-5
• 化学式: C₁₉H₁₆N₂O₆
• 分子量: 368.346
• InChiKey: JWAUGXXRJKZYBD-CAPFRKAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(((1,3-二氧代异吲哚啉-2-基)氧基)甲基)苯基)-2-(甲氧基亚氨基)乙酸甲酯 在 sodium methylate 、 sodium hydride 、 一水合肼 、 potassium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 7.0h， 生成 (E)-5-(methoxyimino)-3-(prop-2-yn-1-yl)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one
  参考文献：
  名称：

  (E)-5-(甲氧基亚氨基)-3,5-二氢苯并[e][1,2]oxazep​​in-4(1H)-one类似物的设计、合成、晶体结构和杀菌活性

  摘要：

  首次报道了1,2-苯并恶吖啶酮的合成。这些化合物显示出优异的杀真菌活性。

  DOI：

  10.1039/c7md00025a
• 作为产物：
  描述：

  o-toluene-diazonium chloride 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium acetate 、 sodium hydride 、 copper(II) sulfate 、 sodium sulfite 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.83h， 生成 (E)-2-(2-(((1,3-二氧代异吲哚啉-2-基)氧基)甲基)苯基)-2-(甲氧基亚氨基)乙酸甲酯
  参考文献：
  名称：

  Stereoselective Synthesis and Antifungal Activities of (E)-α-(Methoxyimino)benzeneacetate Derivatives Containing 1,3,5-Substituted Pyrazole Ring

  摘要：

  Thirteen novel ( E)- R-( methoxyimino) benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of the methyl ( E)- methoxyiminoacetate moiety and 1,3,5-substituted pyrazole ring, were stereoselectively synthesized. It was found that the coupling reaction could give stereoselectively ( E: Z ca. 14: 1) the key intermediate material ( E)- methyl 2-( hydroxyimino)2- o- tolyl acetate ( 2). An X- ray crystallographic structure determination was carried out in a representative product. The preliminary bioassays indicated that all of the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola, and Bipolaris mayclis.

  DOI：

  10.1021/jf060074f

文献信息

• Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides
  申请人：Dow AgroSciences LLC

  公开号：US06348627B1

  公开（公告）日：2002-02-19

  Compounds with fungicidal and insecticidal properties having formula wherein X is N or CH; Z is O, S or NR8; A is hydrogen, halo, cyano, (C1-C12)alkyl, or (C1-C12)alkoxy; R1 and R8 are independently hydrogen or (C1-C4)alkyl; R2 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, heterocyclic(C1-C4)alkyl or C(R10)═N—OR9; R3 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R4 and R5 are independently hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, halo, cyano, (C1-C4)alkoxycarbonyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R6 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, halo, cyano, (C1-C4)alkoxycarbonyl, aryl, aralkyl, aryl(C3-C7)cycloalkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R7 is aryl, aralkyl, heterocyclic or heterocyclic(C1-C4)alkyl; R9 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, aryl, or aralkyl; and R10 is hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, or heterocyclic(C1-C4)alkyl.

  具有杀真菌和杀虫特性的化合物的化学式，其中X为N或CH；Z为O、S或NR8；A为氢、卤素、氰基、(C1-C12)烷基或(C1-C12)烷氧基；R1和R8独立地为氢或(C1-C4)烷基；R2为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环基、杂环基(C1-C4)烷基或C(R10)═N—OR9；R3为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R4和R5独立地为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、卤素、氰基、(C1-C4)烷氧羰基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R6为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、卤素、氰基、(C1-C4)烷氧羰基、芳基、芳基烷基、芳基(C3-C7)环烷基、杂环基或杂环基(C1-C4)烷基；R7为芳基、芳基烷基、杂环基或杂环基(C1-C4)烷基；R9为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、(C1-C4)烷基羰基、(C1-C4)烷氧羰基、芳基或芳基烷基；R10为氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环基或杂环基(C1-C4)烷基。
• Aryl and heteroarylcyclopropyl oxime ethers and their use as fungicides and insecticides
  申请人：ROHM AND HAAS COMPANY

  公开号：EP1024135A1

  公开（公告）日：2000-08-02

  Compounds with fungicidal and insecticidal properties having formula:    wherein X is N or CH; Y is O, S, or NR7; A is selected from the group consisting of hydrogen, halo, cyano, (C1-C12)alkyl, and (C1-C12)alkoxy; R1 and R8 are each independently selected from the group consisting of hydrogen, and (C1-C4)alkyl; R2 is selected from the group consisting of hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, heterocyclic(C1-C4)alkyl, and C(R10)=N-OR9; R3 is selected from the group consisting of aryl, aralkyl, heterocyclic and heterocyclic(C1-C4)alkyl; R4 and R5 are each independently selected from the group consisting of hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, halo, cyano, and (C1-C4)alkoxycarbonyl; R6 and R7 are each independently selected from the group consisting of hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C1-C4)alkoxy(C1-C12)alkyl, halo(C1-C4)alkoxy(C1-C12)alkyl, (C1-C4)alkoxy(C2-C8)alkenyl, and halo(C1-C4)alkoxy(C2-C8)alkenyl; R9 is selected from the group consisting of hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, (C1-C4)alkylcarbonyl, (C1-C4)alkoxycarbonyl, aryl, and aralkyl; and R10 is selected from the group consisting of hydrogen, (C1-C12)alkyl, halo(C1-C12)alkyl, (C3-C7)cycloalkyl, halo(C3-C7)cycloalkyl, (C2-C8)alkenyl, halo(C2-C8)alkenyl, (C2-C8)alkynyl, halo(C2-C8)alkynyl, aryl, aralkyl, heterocyclic, and heterocyclic(C1-C4)alkyl.

  具有杀真菌和杀虫性质的化合物具有以下结构式：其中X为N或CH；Y为O、S或NR7；A选自氢、卤素、氰基、(C1-C12)烷基和(C1-C12)烷氧基；R1和R8各自独立地选自氢和(C1-C4)烷基；R2选自氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环、杂环(C1-C4)烷基和C(R10)=N-OR9；R3选自芳基、芳基烷基、杂环和杂环(C1-C4)烷基；R4和R5各自独立地选自氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、卤素、氰基和(C1-C4)烷氧羰基；R6和R7各自独立地选自氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、(C1-C4)烷氧基(C1-C12)烷基、卤素(C1-C4)烷氧基(C1-C12)烷基、(C1-C4)烷氧基(C2-C8)烯基和卤素(C1-C4)烷氧基(C2-C8)烯基；R9选自氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、(C1-C4)烷基羰基、(C1-C4)烷氧羰基、芳基和芳基烷基；R10选自氢、(C1-C12)烷基、卤素(C1-C12)烷基、(C3-C7)环烷基、卤素(C3-C7)环烷基、(C2-C8)烯基、卤素(C2-C8)烯基、(C2-C8)炔基、卤素(C2-C8)炔基、芳基、芳基烷基、杂环和杂环(C1-C4)烷基。
• Design, synthesis, crystal structure and fungicidal activity of (E)-5-(methoxyimino)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one analogues
  作者：Dongyan Yang、Chuan Wan、MengMeng He、Chuanliang Che、Yumei Xiao、Bin Fu、Zhaohai Qin

  DOI：10.1039/c7md00025a

  日期：——

  It is the first reported the synthesis of 1,2-benzoxazepinone. These compounds showed excellent fungicidal activity.

  首次报道了1,2-苯并恶吖啶酮的合成。这些化合物显示出优异的杀真菌活性。
• [EN] USE OF STROBILURIN TYPE COMPOUNDS FOR COMBATING PHYTOPATHOGENIC FUNGI CONTAINING AN AMINO ACID SUBSTITUTION F129L IN THE MITOCHONDRIAL CYTOCHROME B PROTEIN CONFERRING RESISTANCE TO QO INHIBITORS V<br/>[FR] UTILISATION DE COMPOSÉS DE TYPE STROBILURINE POUR LUTTER CONTRE DES CHAMPIGNONS PHYTOPATHOGÈNES, CONTENANT UNE SUBSTITUTION D'ACIDES AMINÉS F129L DANS LA PROTÉINE CYTOCHROME B MITOCHONDRIAL CONFÉRANT UNE RÉSISTANCE À DES INHIBITEURS DE QO V
  申请人：BASF SE

  公开号：WO2021249928A1

  公开（公告）日：2021-12-16

  The present invention relates to the use of strobilurin type compounds of formula I and the N-oxides and the salts thereof for combating phytopathogenic fungi containing an amino acid substitution F129L in the mitochondrial cytochrome b protein (also referred to as F129L mutation in the mitochondrial cytochrome b gene) conferring resistance to Qo inhibitors, and to methods for combating such fungi. The invention also relates to novel compounds, processes for preparing these compounds, to compositions comprising at least one such compound, and to seeds coated with at least one such compound.

  本发明涉及使用式I的链霉亲菌素类化合物及其N-氧化物和盐，用于对抗含有线粒体细胞色素b蛋白中氨基酸替换F129L（也称线粒体细胞色素b基因中F129L突变）的植物病原真菌，该突变使其对Qo抑制剂产生抗性，并且涉及对抗这种真菌的方法。本发明还涉及新化合物、制备这些化合物的方法、至少包含一种这样的化合物的组合物以及涂有至少一种这样的化合物的种子。
• US5194662A
  申请人：——

  公开号：US5194662A

  公开（公告）日：1993-03-16