S-Ethyl-N,N'-trimethylenethiuronium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: S-Ethyl-N,N'-trimethylenethiuronium bromide
• 英文别名: 2-Ethylsulfanyl-1,4,5,6-tetrahydropyrimidine;hydrobromide；2-ethylsulfanyl-1,4,5,6-tetrahydropyrimidine;hydrobromide
• 化学式: BrH*C₆H₁₂N₂S
• 分子量: 225.153
• InChiKey: ALPMTGLDNYAFPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.83
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  51.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-叔丁基苯乙胺 、 S-Ethyl-N,N'-trimethylenethiuronium bromide 生成 N-[2-(4-tert-butylphenyl)ethyl]-1,4,5,6-tetrahydropyrimidin-2-amine;hydrobromide
  参考文献：
  名称：

  Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors

  摘要：

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.

  DOI：

  10.1002/ps.2780440406

文献信息

• US5292743A
  申请人：——

  公开号：US5292743A

  公开（公告）日：1994-03-08
• [EN] FUNGICIDAL COMPOSITIONS, FUNGICIDAL COMPOUNDS, THEIR PRODUCTION AND USE
  申请人：DOW CHEMICAL COMPANY LIMITED

  公开号：WO1991005473A1

  公开（公告）日：1991-05-02

  (EN) Agricultural fungicidal compositions comprising compounds of formula (I-A), (I-B) or (I-C), wherein R1 and R7 are each independently hydrogen or C1-C3 alkyl, R2 is hydrogen or C1-C6 alkyl, R3 and R4 independently, and each R5 independently are hydrogen or C1-C4 alkyl, R6 is a cyclohexyl group or a monocyclic or bicyclic aromatic group, substituted with from 1 to 5 groups of the formula R8, wherein R8 is halogen, a C1-C10 alkyl group, a C1-C10 alkoxy group, a tri-C1-C4-alkylsilyl group, or a phenoxy, phenyl, phenyl-C1-C2-alkylene, or phenyl-C2-alkenylene group, each optionally substituted on the phenyl or phenoxy group with one or more of halogen atoms, C1-C6 alkyl or C1-C6 alkyl or C1-C6 alkoxy groups, trihalomethyl groups, phenyl groups or phenoxy groups. p is 0, 1 or 2, Y is a group of the formula -(CR9R9)n-, wherein n is 2, 3, or 4, each R9 independently is hydrogen or C1-C4 alkyl and X is a suitable counter-ion, together with an agriculturally acceptable carrier or diluent, and novel fungicidal compounds of formula (I-A), (I-B), or (I-C), wherein p is 1 or 2 and n is 3 or 4.(FR) Compositions fongicides agricoles comprenant des composés de la formule (I-A), (I-B) ou (I-C), où R1 et R7 sont chacun indépendamment hydrogène ou C1-C3 alkyle R2 est hydrogène ou C1-C6 alkyle, R3 et R4 indépendamment et chaque R5 indépendamment sont hydrogène ou C1-C4 alkyle, R6 est un groupe cyclohexyle ou un groupe aromatique monocyclique ou bicyclique, substitué par 1 à 5 groupes de la formule R8, où R8 est halogène, un groupe alhyle C1-C10, un groupe alkoxy C1-C10, un groupe tri-C1-C4-alkylsilyle, ou un groupe phénoxy, phényle, phényle-C1-C2-alkylène ou phényle-C2-alkenylène, chacun optionnellement substituté sur le groupe phényle ou phénoxy par un atome d'hydrogène ou davantage, des groupes alkyle C1-C6 ou alkyle C1-C6, ou alkoxy C1-C6, des groupes trihalométhyle, phényle ou phénoxy. p est 0, 1 ou 2, Y est un groupe de la formule -(CR9R9)n-, où n est 2, 3 ou 4, chaque R9 indépendamment est hydrogène ou C1-C4 alkyle et X est un contre-ion approprié, l'ensemble avec un diluant ou un transporteur acceptable pour l'agriculture, et de nouveaux composés fongicides de la formule (I-A), (I-B) ou (I-C) où p est 1 ou 2 et n est 3 ou 4.
• Guanidinium and amidinium fungicides: A new class of carbocation mimetic ergosterol biosynthesis inhibitors
  作者：Mary L. Arnold、Albert D. Duriatti、Michel Jung、Ruth B. Katz、John W. Liebeschuetz

  DOI：10.1002/ps.2780440406

  日期：1995.8

  AbstractA novel class of chemical has been designed with the aim of inhibiting the Δ14‐reductase and Δ8‐Δ7‐isomerase enzymes in the ergosterol biosynthesis pathway in fungi. Use was made of knowledge about the mechanisms of both enzymes and the mode of action of known, fungicidal inhibitors of these enzymes. Pioneer examples have been synthesised and have been demonstrated to be potent inhibitors of ergosterol biosynthesis in Ustilago maydis (DC) Corda, acting in the same manner as the commercial fungicide fenpropimorph. They also showed excellent fungicidal activity against Erysiphe graminis DC f. sp. hordei Marchal (powdery mildew of barley) and Puccinia recondita Rob. ex Desm. (wheat leaf rust) in in‐vivo glasshouse tests. Using these compounds as a starting point, systematic structural variation has been carried out. Testing of a wide range of analogues at high volume confirms the potential of this class of compound to control mildew and rust pathogens at levels comparable to those of the standards. Correlation of in‐vivo and enzymatic data is good and the structure‐activity relationship developed for this series of compounds closely parallels that found for the morpholine/piperidine class of fungicides, suggesting a common mode of action.