多恶菌素D，可可链霉菌变种。麻生 | 22976-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 多恶菌素D，可可链霉菌变种。麻生
• 英文名称: Polyoxin D
• 英文别名: beta-D-Allofuranuronic acid, 5-[[2-amino-5-O-(aminocarbonyl)-2-deoxy-L-xylonoyl]amino]-1-(5-carboxy-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-1,5-dideoxy-；1-[(2R,3R,4S,5R)-5-[(S)-[[(2S,3S,4S)-2-amino-5-carbamoyloxy-3,4-dihydroxypentanoyl]amino]-carboxymethyl]-3,4-dihydroxyoxolan-2-yl]-2,4-dioxopyrimidine-5-carboxylic acid
• CAS: 22976-86-9
• 化学式: C₁₇H₂₃N₅O₁₄
• 分子量: 521.395
• InChiKey: JPFWJDMDPLEUBD-ITJAGOAWSA-N

物化性质

• 熔点：
  173-175 °C (decomp)
• 密度：
  1.864±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -7.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  322
• 氢给体数：
  10
• 氢受体数：
  15

制备方法与用途

生物活性

Polyoxin D（Polyoxorim）是一种多抗霉素类抗生素杀真菌剂，有效抑制几丁质合成酶（chitin synthetase）。

反应信息

• 作为反应物：
  描述：

  多恶菌素D，可可链霉菌变种。麻生 在 N-甲基吗啉 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 TFA*Phe-polyoxin D
  参考文献：
  名称：

  Synthesis and biological properties of chitin synthetase inhibitors resistant to cellular peptidases

  摘要：

  The synthesis and biological properties of seven polyoxins (4-10) designed to avoid peptidase hydrolysis in Candida albicans are presented. Five dipeptidyl and two tripeptidyl polyoxin analogues were synthesized by coupling an amino acid active ester or azlactone to uracil polyoxin C (2) or polyoxin D (1), subsequent removal of the protecting group, and purification by preparative HPLC. A new and novel route for introducing an n-propyl group onto the alpha-amino group of peptides is reported. With the exception of a carboxamide derivative, 8, all analogues were resistant to hydrolysis by a cell extract or permeabilized cells of Candida. Chitin synthetase inhibition constants were determined for 4-10 and the KI values ranged from 7.15 X 10(-6) M for octanoyl-phenylalanyl-polyoxin D (10) to 1.06 X 10(-3) M for D-tryptophanyl-uracil polyoxin C (6). These novel polyoxins do not compete with the transport of either peptides or uridine into the cell. Millimolar concentrations of compounds 4-10 are required to inhibit growth, cause morphological alterations, or reduce the viability of C. albicans.

  DOI：

  10.1021/jm00155a034
• 作为产物：
  描述：

  Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 水 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 多恶菌素D，可可链霉菌变种。麻生
  参考文献：
  名称：

  Uchida, Kimio; Kato, Keisuke; Yamaguchi, Kentaro, Heterocycles, 2000, vol. 53, # 10, p. 2253 - 2259

  摘要：

  DOI：

文献信息

• Fungicidal Mixtres Based On 3-Monosubstituted N-Bipenyl-Pyrazolecarboxamides
  申请人：Dietz Jochen

  公开号：US20090233795A1

  公开（公告）日：2009-09-17

  Fungicidal mixtures comprising, as active components, 1) at least one 3-mono disubstituted N-biphenylpyrazolecarboxamide of the formula I in which X=oxygen or sulfur; R 1 =cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, methoxy, difluoromethoxy, trifluoromethoxy, methylthio, difluoromethylthio or trifluoromethylthio; R 2 =halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 3 =hydrogen or halogen; and 2) at least one active compound II selected from active compound groups A) to F): A) azoles; B) strobilurins; C) carboxamides; D) heterocyclic compounds; E) carbamates; F) other fungicides; in a synergistically effective amount, methods for controlling harmful fungi using mixtures of at least one compound I and at least one active compound II, the use of the compound(s) I with active compounds II for preparing such mixtures and also compositions and seed comprising these mixtures.

  含有杀真菌混合物，其活性成分为1) 至少一种具有以下化学式I的3-单二取代N-联苯基吡唑羧酰胺，其中X=氧或硫；R1=氰基、硝基、卤素、C1-C6-烷基、C1-C6-卤代烷基、甲氧基、二氟甲氧基、三氟甲氧基、甲硫氧基、二氟甲硫基或三氟甲硫基；R2=卤素、C1-C4-烷基或C1-C4-卤代烷基；R3=氢或卤素；以及2) 从活性化合物组A)至F)中选择的至少一种活性化合物II：A) 唑类；B) 叠氮酮；C) 联苯基胺；D) 杂环化合物；E) 氨基甲酸酯；F) 其他杀真菌剂；在协同作用有效量下的方法，使用至少一种化合物I和至少一种活性化合合物II的混合物来控制有害真菌，使用化合物I与活性化合合物II来制备这种混合物，以及包含这些混合物的组合物和种子。
• Fungicidal Mixtures Based on 3,5-Disubstituted N-Biphenyl-Pyrazolcarboxamides
  申请人：Dietz Jochen

  公开号：US20090042725A1

  公开（公告）日：2009-02-12

  The invention relates to fungicide mixtures containing in the form of active componenets: 1) at least one type of 3,5-disubstituted pyrazol-carboxylic acid biphenylamide of (formula I), wherein X=oxygen or sulfur, R 1 and R 2 =cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenalkyl, methoxy, difluormethoxy or trifluormethoxy; R 3 =halogen, C 1 -C 4 -alkyl or C 1 -C 4 -halogenalkyl; R 4 =hydrogen or halogen; and (2) at least one type of active substance II selected from A) to F) groups: A) azole; B) strobilurin; C) carboxylic add amides; D) heterocyclic compounds; E) carbamates and F) other fungicides in synergistically active quantity. A method for combating parasitic fungi by means of mixtures consisting of at least one type of compound I and at least one type of active substance II, the use of the compound(s) I with the active substances II for producing said mixtures and substances and seeds containing them are also disclosed.

  本发明涉及含有以下活性成分的杀真菌混合物：1）至少一种3,5-二取代吡唑-羧酸联苯酰胺（式I）的活性成分，其中X=氧或硫，R1和R2=氰基、硝基、卤素、C1-C6烷基、C1-C6卤代烷基、甲氧基、二氟甲氧基或三氟甲氧基；R3=卤素、C1-C4烷基或C1-C4卤代烷基；R4=氢或卤素；以及2）至少一种选自A）至F）组的活性物质II：A）唑类；B）菌核素；C）羧酸酰胺；D）杂环化合物；E）氨基甲酸酯和F）其他杀真菌剂的协同活性量。还公开了一种通过使用至少一种化合物I和至少一种活性物质II的混合物来对抗寄生真菌的方法，以及使用化合物I与活性物质II制造所述混合物，以及包含它们的物质和种子的用途。
• Fungicidal Mixtures Based on 2,5-Disubstituted N-Biphenylpyrazolcarboxamides
  申请人：Dietz Jochen

  公开号：US20090239748A1

  公开（公告）日：2009-09-24

  The present invention relates to fungicidal mixtures comprising, as active components, 1) at least one 2,5-disubstituted N-biphenylpyrazolecarboxamide of the formula I in which X=oxygen or sulfur; R 1 and R 2 =cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, methoxy, difluoromethoxy or trifluoromethoxy; R 3 =halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 4 =hydrogen or halogen; and 2) at least one active compound II selected from groups A) to F): A) azoles; B) strobilurins; C) carboxamides; D) heterocyclic compounds; E) carbamates; F) other fungicides; in a synergistically effective amount, methods for controlling harmful fungi using mixtures of at least one compound I and at least one active compound II, the use of the compound(s) I with active compounds II for preparing such mixtures and also compositions and seed comprising these mixtures.

  本发明涉及杀真菌混合物，其包含以下活性成分：1）至少一种式I的2,5-二取代N-联苯基吡唑羧酰胺，其中X=氧或硫；R1和R2=氰基、硝基、卤素、C1-C6烷基、C1-C6卤代烷基、甲氧基、二氟甲氧基或三氟甲氧基；R3=卤素、C1-C4烷基或C1-C4卤代烷基；R4=氢或卤素；以及2）至少一种从A）到F）组中选择的活性化合物II：A）唑类；B）菌核素；C）羧酰胺；D）杂环化合物；E）氨基甲酸酯；F）其他杀真菌剂。本发明还提供了使用至少一种化合物I和至少一种活性化合物II的混合物控制有害真菌的方法，使用化合物I与活性化合物II制备这种混合物的用途，以及包含这些混合物的组合物和种子。
• Fungicidal mixtures based on 2,4-disubstituted n-biphenylpyrazolecarboxamides
  申请人：Dietz Jochen

  公开号：US20090042724A1

  公开（公告）日：2009-02-12

  The present invention relates to fungicidal mixtures comprising, as active components, 1) at least one 2,4-disubstituted N-biphenylpyrazolecarboxamide of the formula I in which X=oxygen or sulfur; R 1 and R 2 =independently of one another cyano, nitro, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, methoxy, difluoromethoxy or trifluoromethoxy; R 3 =halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 4 =hydrogen or halogen; and 2 ) at least one active compound II selected from groups A) to F): A) azoles; B) strobilurins; C) carboxamides; D) heterocyclic compounds; E) carbamates; F) other fungicides; in a synergistically effective amount, methods for controlling harmful fungi using mixtures of at least one compound I and at least one active compound II, the use of the compounds I with active compounds II for preparing such mixtures and also compositions and seed comprising these mixtures.

  本发明涉及杀真菌混合物，其包括以下活性成分：1) 至少一种式I的2,4-二取代N-联苯基吡唑甲酰胺，其中X=氧或硫；R1和R2独立地为氰基、硝基、卤素、C1-C6烷基、C1-C6卤代烷基、甲氧基、二氟甲氧基或三氟甲氧基；R3为卤素、C1-C4烷基或C1-C4卤代烷基；R4为氢或卤素；以及2) 至少一种选自A) 至 F) 组的活性化合物II：A) 咪唑类；B) 史托比林；C) 羧酰胺；D) 杂环化合物；E) 氨基甲酸酯；F) 其他杀真菌剂；在协同有效量下，使用至少一种化合物I和至少一种活性化合物II的混合物来控制有害真菌的方法，使用化合物I与活性化合物II制备这种混合物以及包含这些混合物的组合物和种子。
• Method For Controlling Fungal Pests
  申请人：Stammler Gerd

  公开号：US20100210652A1

  公开（公告）日：2010-08-19

  A method of controlling harmful fungi which are resistant to carboxamide fungicides consists in applying a fungicidally active amount of a compound of the general formula (I) where —R denotes, for example: —OCH 3 , —OC 2 H 5 or —OCH 2 —C≡CH and where —X denotes either —Cl or —F and where —Z— denotes, for example, a group: preventatively to the plants.

  一种控制对卡巴胺类杀菌剂有抗性的有害真菌的方法，包括施用一种通式（I）的化合物的杀菌有效量，其中—R表示例如：—OCH3，—OC2H5或—OCH2—C≡CH，而—X表示—Cl或—F，而—Z—表示例如，一种预防性地施用于植物的基团。