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WO2010029066A1 - Composés d'imidazole et de triazole, leur utilisation et produits contenant ces composés - Google Patents

Composés d'imidazole et de triazole, leur utilisation et produits contenant ces composés Download PDF

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Publication number
WO2010029066A1
WO2010029066A1 PCT/EP2009/061616 EP2009061616W WO2010029066A1 WO 2010029066 A1 WO2010029066 A1 WO 2010029066A1 EP 2009061616 W EP2009061616 W EP 2009061616W WO 2010029066 A1 WO2010029066 A1 WO 2010029066A1
Authority
WO
WIPO (PCT)
Prior art keywords
compounds
alkyl
cio
cycloalkyl
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2009/061616
Other languages
German (de)
English (en)
Inventor
Jens Renner
Jochen Dietz
Thomas Grote
Bernd Müller
Jan Klaas Lohmann
Sarah Ulmschneider
Alice GLÄTTLI
Marianna Vrettou
Wassilios Grammenos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of WO2010029066A1 publication Critical patent/WO2010029066A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms

Definitions

  • a 1 is hydrogen, hydroxy, Ci-C 8 -alkyl, C 8 haloalkyl, amino, Ci-C 8 -
  • inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, carbonic acid, sulfuric acid, phosphoric acid and nitric acid.
  • Suitable organic acids are, for example, formic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms ), Arylsulfonic acids or disulfonic acids (aromatic radicals such as phenyl and naphthyl carrying one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon
  • the compounds I according to the invention can be prepared in various ways in analogy to prior art processes known per se (see, for example, the cited prior art or EP 0 129 186, EP 0 129 152).
  • the compounds of the invention can be prepared by the syntheses shown in the following Schemes.
  • n in the group Z 1 stands for 4.
  • R Z1 , R Z2 , R Z5 and R Z6 are hydrogen.
  • R Z1 , R Z2 , R Z5 and R Z6 are independent of each other. which is selected from hydrogen and halogen (especially F and Cl), wherein at least one R z thereof is not hydrogen.
  • # represent the attachment sites
  • m and p are each 0, 1 or 2, where m + p> 1, preferably m + p> 2, and R Z1 , R Z2 , R Z3 and R Z4 are each independently selected is hydrogen and R z , where R z is each as defined herein or preferably defined.
  • the phenyl group is 2,4-disubstituted. In yet another embodiment, the phenyl group is 2,5-disubstituted. In yet another embodiment, the phenyl group is 2,6-disubstituted.
  • R 5 is CH 3 and R 6 + R 7 is cyclopentyl, and the combination of R 1 and Y corresponds in each case to one line of Table A (compounds I .A.1 17aA-1 to I .A.117aA-444).
  • Table 1 18a Compounds LA in which Z is CH 2 CH (CH 3 ) (CH 2 ) 2 CH 2 , R 2 , R 3 and R 4 are H, R 5 is CH 3 and R 6 + R 7 is cyclopentyl, and the combination from R 1 and Y corresponds in each case to one row of Table A (Compounds IA118aA-1 to IA118aA-444).
  • Table 1 19a Compounds LA in which Z is C (CH 3 ) 2 (CH 2 ) 3 CH 2 , R 2 , R 3 and R 4 stand for H,
  • Steroid metabolizing enzymes e.g. 3-hydroxy steroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase
  • ion channel blocker
  • Botrytis cinerea Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz) on deciduous and coniferous trees, z.
  • Botrytis cinerea Triomorph: Botryotina fuckeliana: gray mold, gray mold) on berry and pome fruit (including strawberries), vegetables (including lettuce, carrots, celery and cabbage), oilseed rape, flowers, vines, forestry crops and wheat (ear fungus); Bremia lactucae (downy mildew) on salad; Ceratocystis (Syn. Ophiostoma) spp. (Bläuepilz)
  • BP asparagi Pyrenophora (anamorph: Drechslera) tritici-repentis (leaf drought) on wheat or P. teres (net stains) on barley; Pyricularia spp., E.g. BP oryzae (teleomorph: Magnaporthe grisea, rice leaf-brandy) on rice and P. grisea on seeds and cereals; Pythium spp. (Turnip disease) on turf, rice, corn, wheat,
  • cerealis pointed eye-spot on wheat or barley; Rhizopus stolonifer (soft rot) on strawberries, carrots, cabbage, grapevine and tomato; Rhynchosporium secalis (leaf spot) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (Stem or white rot) in vegetables and crops such as oilseed rape, sunflowers (eg Sclerotinia sclerotium rum) and soybeans (eg BS rolfsii); Septoria spp. on different plants, eg.
  • the solvents used include water, organic solvents such as mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons.
  • aliphatic hydrocarbons for example paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, glycols, ketones such as cyclohexanone, gamma-butyrolactone, dimethyl fatty acid amides, fatty acids and fatty acid esters and strongly polar solvents, for example amines such as N-methylpyrrolidone, into consideration.
  • solvent mixtures and mixtures of the abovementioned solvents and water can also be used.
  • the activity spectrum can be broadened or resistance developments can be prevented. In many cases, synergistic effects are obtained.
  • Benzoic acid amides flumetover, fluopicolide, fluopyram, zoxamide, N- (3-ethyl-3,5,5-trimethylcyclohexyl) -3-formylamino-2-hydroxybenzamide;
  • antibiotics kasugamycin, kasugamycin hydrochloride hydrate, polyoxines, streptomycin, validamycin A;
  • Amino acid analogues bilanafos, glyphosate, glufosinate, sulfosate;
  • Macrocyclic lactones Abamectin, Emamectin, Milbemectin, Lepimectin, Spinosid, Spinetoram;
  • Another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of diseases, in particular the use of the compounds I as an antimycotic.
  • a pharmaceutical composition comprising at least one compound of the formula I and / or a pharmaceutically acceptable salt thereof.
  • Another embodiment relates to the use of a compound I and / or a pharmaceutically active salt thereof for the manufacture of an antimycotic.
  • Yet another object of the present invention is the use of compounds I and their pharmaceutically acceptable salts for the treatment of viral infections, in particular viral infections, which lead to diseases in warm-blooded animals.
  • one embodiment of the invention relates to the use of a compound I and / or a pharmaceutically active salt thereof for the manufacture of an agent for the treatment of viral infections.
  • the viral diseases to be treated include retrovirus diseases such as: HIV and HTLV, influenza virus, rhino-virus diseases, herpes and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés de formule (I), dans laquelle les variables ont les significations définies dans les revendications et la description.
PCT/EP2009/061616 2008-09-10 2009-09-08 Composés d'imidazole et de triazole, leur utilisation et produits contenant ces composés Ceased WO2010029066A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08164041.9 2008-09-10
EP08164041 2008-09-10

Publications (1)

Publication Number Publication Date
WO2010029066A1 true WO2010029066A1 (fr) 2010-03-18

Family

ID=41478777

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2009/061616 Ceased WO2010029066A1 (fr) 2008-09-10 2009-09-08 Composés d'imidazole et de triazole, leur utilisation et produits contenant ces composés

Country Status (3)

Country Link
AR (1) AR073286A1 (fr)
UY (1) UY32108A (fr)
WO (1) WO2010029066A1 (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103664808A (zh) * 2013-11-26 2014-03-26 中国农业大学 一种含氯代环丙烷的芳基三氮唑化合物及其制备方法与应用
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746260A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
WO2014167009A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazole
WO2014167008A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazolinthione
CN104151149A (zh) * 2014-08-07 2014-11-19 西安近代化学研究所 一种1-乙酰基-1-氯环丙烷的合成方法
CN104292089A (zh) * 2014-09-30 2015-01-21 大连九信生物化工科技有限公司 一种1-氯-1’-氯乙酰基环丙烷的合成工艺
CN105461533A (zh) * 2015-11-24 2016-04-06 大连世慕化学有限公司 3,5-二氯-2-戊酮的合成方法
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2016156294A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Dérivés de triazole utiles en tant que fongicides
CN106278845A (zh) * 2016-05-19 2017-01-04 海正化工南通股份有限公司 一种3,5-二氯-2-戊酮的合成工艺
US9668481B2 (en) 2013-04-12 2017-06-06 Bayer Cropscience Aktiengesellschaft Triazole derivatives
WO2018050456A1 (fr) 2016-09-13 2018-03-22 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs comprenant un dérivé d'imidazole substitué en position 5
WO2018060073A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2018060075A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Dérivés de 1 -[2- (1 -chlorocyclopropyl)-2-hydroxy-3-(3-phényl -1,2-oxazol-5-yl) propyl] -1 h-imidazole-5-carbonitrile et composés apparentés en tant que fongicides pour la protection des cultures
WO2018060074A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazolylmethyle à substitution en position 5
WO2019092086A1 (fr) 2017-11-13 2019-05-16 Bayer Aktiengesellschaft Dérivés de tétrazolylpropyle et leur utilisation en tant que fongicides
CN114685253A (zh) * 2020-12-30 2022-07-01 南通泰禾化工股份有限公司 一种丙硫菌唑中间体3,5-二氯-2-戊酮的制备方法
CN115626899A (zh) * 2022-12-08 2023-01-20 江苏禾本生化有限公司 一种戊菌唑的生产方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069290A1 (fr) * 1981-07-02 1983-01-12 BASF Aktiengesellschaft Dérivés azolyles, leur procédé de préparation et les fongicides les contenant
EP0079006A1 (fr) * 1981-11-10 1983-05-18 Bayer Ag Azolyl-alkénones et -ols, leur procédé de préparation et leur application comme agents régulateurs de croissance des plantes et fongicides
EP0109476A1 (fr) * 1982-03-16 1984-05-30 Bayer Ag Phénoxypropyltriazolyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides ainsi que des intermédiaires de synthèse
EP0159586A2 (fr) * 1984-04-26 1985-10-30 BASF Aktiengesellschaft Dérivés d'azoles, leur procédé de préparation et fongicides les contenant
EP0178587A2 (fr) * 1984-10-17 1986-04-23 BASF Aktiengesellschaft Benzyloxyalkylazoles et fongicides les contenant
EP0200149A2 (fr) * 1985-04-27 1986-11-05 BASF Aktiengesellschaft 1,3-Dioxane-5-yl alkyl triazoles, leur préparation, leur utilisation comme régulateur pour la croissance des plantes et composition
EP0199982A2 (fr) * 1985-04-01 1986-11-05 BASF Aktiengesellschaft Dérivés azoliques, leur procédé de préparation et composition pour régler la croissance des plantes
EP0236884A1 (fr) * 1986-03-04 1987-09-16 BASF Aktiengesellschaft Procédé pour la préparation de composés phénoxyalcanoltriazoliques et produits intermédiaires à cet effet
EP0297393A2 (fr) * 1987-07-01 1989-01-04 Bayer Ag Dérivés de 1-phénoxy-3-triazolyl-hex-1-ènes

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0069290A1 (fr) * 1981-07-02 1983-01-12 BASF Aktiengesellschaft Dérivés azolyles, leur procédé de préparation et les fongicides les contenant
EP0079006A1 (fr) * 1981-11-10 1983-05-18 Bayer Ag Azolyl-alkénones et -ols, leur procédé de préparation et leur application comme agents régulateurs de croissance des plantes et fongicides
EP0109476A1 (fr) * 1982-03-16 1984-05-30 Bayer Ag Phénoxypropyltriazolyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides ainsi que des intermédiaires de synthèse
EP0159586A2 (fr) * 1984-04-26 1985-10-30 BASF Aktiengesellschaft Dérivés d'azoles, leur procédé de préparation et fongicides les contenant
EP0178587A2 (fr) * 1984-10-17 1986-04-23 BASF Aktiengesellschaft Benzyloxyalkylazoles et fongicides les contenant
EP0199982A2 (fr) * 1985-04-01 1986-11-05 BASF Aktiengesellschaft Dérivés azoliques, leur procédé de préparation et composition pour régler la croissance des plantes
EP0200149A2 (fr) * 1985-04-27 1986-11-05 BASF Aktiengesellschaft 1,3-Dioxane-5-yl alkyl triazoles, leur préparation, leur utilisation comme régulateur pour la croissance des plantes et composition
EP0236884A1 (fr) * 1986-03-04 1987-09-16 BASF Aktiengesellschaft Procédé pour la préparation de composés phénoxyalcanoltriazoliques et produits intermédiaires à cet effet
EP0297393A2 (fr) * 1987-07-01 1989-01-04 Bayer Ag Dérivés de 1-phénoxy-3-triazolyl-hex-1-ènes

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2746259A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
EP2746260A1 (fr) 2012-12-21 2014-06-25 Basf Se Composés de [1,2,4]triazole et d'imidazole substitués
US9550752B2 (en) 2013-04-12 2017-01-24 Bayer Cropscience Aktiengesellschaft Triazolinthione derivatives
WO2014167009A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazole
WO2014167008A1 (fr) 2013-04-12 2014-10-16 Bayer Cropscience Ag Nouveaux dérivés triazolinthione
US9822099B2 (en) 2013-04-12 2017-11-21 Bayer Cropscience Aktiengesellschaft Triazole derivatives
US9668481B2 (en) 2013-04-12 2017-06-06 Bayer Cropscience Aktiengesellschaft Triazole derivatives
CN103664808A (zh) * 2013-11-26 2014-03-26 中国农业大学 一种含氯代环丙烷的芳基三氮唑化合物及其制备方法与应用
CN104151149A (zh) * 2014-08-07 2014-11-19 西安近代化学研究所 一种1-乙酰基-1-氯环丙烷的合成方法
CN104292089A (zh) * 2014-09-30 2015-01-21 大连九信生物化工科技有限公司 一种1-氯-1’-氯乙酰基环丙烷的合成工艺
CN104292089B (zh) * 2014-09-30 2016-01-13 大连九信生物化工科技有限公司 一种1-氯-1’-氯乙酰基环丙烷的合成工艺
WO2016156294A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Dérivés de triazole utiles en tant que fongicides
WO2016156290A1 (fr) 2015-04-02 2016-10-06 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
CN105461533A (zh) * 2015-11-24 2016-04-06 大连世慕化学有限公司 3,5-二氯-2-戊酮的合成方法
CN106278845A (zh) * 2016-05-19 2017-01-04 海正化工南通股份有限公司 一种3,5-二氯-2-戊酮的合成工艺
WO2018050456A1 (fr) 2016-09-13 2018-03-22 Bayer Cropscience Aktiengesellschaft Combinaisons de composés actifs comprenant un dérivé d'imidazole substitué en position 5
WO2018060073A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazole à substitution en position 5
WO2018060075A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Dérivés de 1 -[2- (1 -chlorocyclopropyl)-2-hydroxy-3-(3-phényl -1,2-oxazol-5-yl) propyl] -1 h-imidazole-5-carbonitrile et composés apparentés en tant que fongicides pour la protection des cultures
WO2018060074A1 (fr) 2016-09-29 2018-04-05 Bayer Cropscience Aktiengesellschaft Nouveaux dérivés d'imidazolylmethyle à substitution en position 5
WO2019092086A1 (fr) 2017-11-13 2019-05-16 Bayer Aktiengesellschaft Dérivés de tétrazolylpropyle et leur utilisation en tant que fongicides
CN114685253A (zh) * 2020-12-30 2022-07-01 南通泰禾化工股份有限公司 一种丙硫菌唑中间体3,5-二氯-2-戊酮的制备方法
CN115626899A (zh) * 2022-12-08 2023-01-20 江苏禾本生化有限公司 一种戊菌唑的生产方法

Also Published As

Publication number Publication date
UY32108A (es) 2010-03-26
AR073286A1 (es) 2010-10-28

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