- NOVEL METHOD FOR PREPARATION OF EPOXYTRIAZOLE DERIVATIVES
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The present invention relates to novel processes for preparing epoxytriazole derivatives. The method of claim 1, further comprising the step of adding a base to the intermediate compound. The present invention relates to an epoxytriazole derivative and a manufacturing method thereof. Chemical Formula 1. Here, Ar denotes C. 6 -C10 Aryl group or C aryl group2 -C9 The aryl group 1 -4 is substituted or unsubstituted, and when 2 or more halogen is substituted, the heteroaryl group may be the same as or different from each other, and the heteroaryl group is represented by 1 -4 fluorine, chlorine, or C. 1 -C3 Substituted or unsubstituted alkyl groups, and fluorine, chlorine, or C. 1 -C3 When more than 2 substituents are substituted, each of these substituents may be the same or different and may be different from each other. The A is C. 1 -C3 Represents an alkyl group, and the R represents an alkyl group. 1 And R2 Is a methyl group or an ethyl group.
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Paragraph 0109; 0115-0116; 0126-0127
(2021/04/13)
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- Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
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An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
- Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Zhang, Dong,Zhang, Fengcai
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p. 6961 - 6966
(2021/09/11)
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- Triazole alcohol derivative, and preparation method and application thereof
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The invention relates to a triazole alcohol derivative, and a preparation method and an application thereof. The chemical structure of the triazole alcohol derivative is represented by formula I, A inthe formula I represents a benzene ring or a substituted benzene ring, and the substituent group of the substituted benzene ring can be located at each position of the benzene ring, is monosubstituted or polysubstituted, and is selected from: a) halogen which is F, Cl, Br or I; b) an electron-withdrawing group, wherein the electron withdrawing group is a cyano group, a nitro group or a trifluoromethyl group; c) a C1-4 low alkyl group or a halogen-substituted low alkyl group; and d) a C1-4 low alkoxy group or a halogen-substituted low alkoxy group. The compound has the advantages of high antifungal activity, low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal medicines.
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- PROCESS FOR PRODUCING EPOXY ALCOHOL COMPOUND
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A compound represented by formula (II): (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): that is useful for production of an antifungal agent.
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- METHOD FOR PREPARATION OF EFINACONAZOLE IN IONIC LIQUID MEDIUM
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The present invention relates to a novel method for preparation of efinaconazole in an ionic liquid medium, the method comprising: reacting 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole, and 4-methylenepiperidine or an organic chemically acceptable salt thereof, wherein the 4-methylenepiperidine or the organic chemically acceptable salt thereof is anionized on a base; and performing a coupling reaction with the 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole in the presence of an ionic liquid compound. The present invention uses an ionic liquid instead of an organic solvent when preparing efinaconazole, thereby reducing related substances compared to the conventional method, shortens the reaction time, thereby making it possible to easily obtain the final compound, efinaconazole, with high purity and high yield, and may be very suitably used for mass production.
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Paragraph 0090-0093
(2021/01/29)
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- Design, synthesis, and structure-activity relationship studies of novel triazole agents with strong antifungal activity against Aspergillus fumigatus
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The incidence of invasive fungal infections has dramatically increased for several decades. In order to discover novel antifungal agents with broad spectrum and anti-Aspergillus efficacy, a series of novel triazole derivatives containing 1,2,3-benzotriazin-4-one was designed and synthesized. Most of the compounds exhibited stronger in vitro antifungal activities against tested fungi than fluconazole. Moreover, 6m showed comparable antifungal activity against seven pathogenic strains as voriconazole and albaconazole, especially against Aspergillus fumigatus (MIC = 0.25 μg/ml), and displayed moderate antifungal activity against fluconazole-resistant strains of Candida albicans. A clear SAR study indicated that compounds with groups at the 7-position resulted in novel antifungal triazoles with more effectiveness and a broader-spectrum.
- Ding, Zichao,Ni, Tingjunhong,Xie, Fei,Hao, Yumeng,Yu, Shichong,Chai, Xiaoyun,Jin, Yongsheng,Wang, Ting,Jiang, Yuanying,Zhang, Dazhi
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supporting information
(2020/01/13)
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- Method for preparing efinaconazole intermediate
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The invention discloses a method for preparing an efinaconazole intermediate. The method comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound as shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant to prepare a compound as shown in the formula 3, wherein R is halogen or 1,2,4-triazolyl, and R is hydrogen or methyl. The method is green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formula 2 and the formula 3 are as shown in the description.
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- Efinaconazole, preparation method of efinaconazole intermediate and efinaconazole intermediate
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The invention discloses efinaconazole, a preparation method of an efinaconazole intermediate and the efinaconazole intermediate. A preparation method of efinaconazole comprises the following step: in a solvent, under the action of a reducing agent, performing reductive amination reaction on a compound shown in the formula 4 and a compound shown in the formula B. The invention also provides the efinaconazole intermediate shown in the formula 4 and the preparation method thereof, and the preparation method comprises the following step: performing oxidizing reaction on a compound shown in the formula 3 to obtain the compound shown in the formula 4. A preparation method of the compound shown in the formula 3 comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant. The efinaconazole and the preparation method of the efinaconazole intermediate are green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formulas 2, 3, 4 and B are as shown in the description.
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- A preparation method of the midbody sets up lucky Kang Zuo (by machine translation)
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The invention relates to the field of pharmaceutical technology, in particular to a method of preparing intermediates of sets up lucky Kang Zuo, comprising the following steps: D, L - methyl lactate, morpholine, 3, 4 - methoxychroman reaction, with 2, 4 - difluoro bromobenzene reagent reaction to obtain compound III format; compound III in the catalyst under the catalysis of the B L - menthol and triphenylphosphine, by the asymmetric kohl Chaikefusiji reaction to obtain the chiral compound IV; compound IV with 1, 2, 4 - triazole reaction, and then removing the water Cheng Huan, get sets up lucky Kang Zuo key intermediate compound V, this invention uses the D, L - lactic acid methyl ester, by adding the catalyst induction to generate chiral center, greatly reducing the reaction of the raw material cost, high yield, high purity, easy controlled, is suitable for industrial production. (by machine translation)
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Paragraph 0037; 0042; 0046
(2017/08/29)
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- Synthetic method of efinaconazole intermediate
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The invention relates to a synthetic method of an efinaconazole intermediate and discloses a synthetic method of the efinaconazole intermediate (2R, 3S)-2-(2, 4-difluorophenyl)-3-methyl-2-((1H-1, 2, 4 triazol-group) methyl) ethylene oxide. The preparation method comprises the following steps: synthesizing alpha-(1H-1, 2, 4 triazol)-2, 4-difluoroacetophenone by substitution reaction of alpha-halogenated-2, 4-difluoroacetophenone and 1H-1, 2, 4-triazole, then reacting with a sulfur ylide reagent, and synthesizing 2-(2, 4-difluorophenyl)-3-methyl-2-((1H-1, 2, 4 triazol-group) methyl) ethylene oxide. The synthetic method has the advantages that the used materials are low in price and easy in obtaining, the conditions are mild, the operation is simple, the environmental pollution is less and the production cost is low, and the synthetic method is suitable for industrial production.
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Paragraph 0017; 0019
(2017/08/31)
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- Synthetic method for antifungal drug intermediate (2R,3S)-1-(1,2,4-triazol)-2-difluorophenyl-2,3-epoxybutane
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The invention discloses a synthetic method for an antifungal drug intermediate (2R,3S)-1-(1,2,4-triazol)-2-difluorophenyl-2,3-epoxybutane. The synthetic method comprises the following steps: (1) reacting a compound IV with a Grignard reagent to obtain a compound III; (2) employing a one-pot reaction to react the compound III with trimethylsulfoxonium iodide and 1,2,4-triazole and then react with p-toluenesulfonic acid, so as to obtain a compound II; and (3) reacting the compound II with methanesulfonyl chloride under an alkali condition to generate the target compound I, wherein the Grignard reagent is 2,4-difluorophenylmagnesium bromide or 2,5-difluorophenylmagnesium bromide, and the structural formula of the compound IV is shown in the specification. According to the synthetic route, the reaction conditions are mild and easy to control, the reaction route is simple, the related solvents in the reaction process all are common solvents, the reaction conversion rate is high, and the method possesses extremely high feasibility, is beneficial for industrialized batch production, and possesses extremely large exploitation potential and extremely good application prospect.
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- An enantioselective synthesis of the key intermediate for triazole antifungal agents; Application to the catalytic asymmetric synthesis of efinaconazole (jublia)
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A new synthetic route, the shortest reported to date, to access a key intermediate for the synthesis of various triazole antifungal agents was developed. The elusive tetrasubstituted stereogenic center that is essential in advanced triazole antifungal agents was constructed via the catalytic asymmetric cyanosilylation of a ketone. The subsequent transformations were performed in two one-pot operations, enhancing the overall synthetic efficiency toward the intermediate. This streamlined synthetic approach was successfully applied to efficient enantioselective syntheses of efinaconazole (Jublia) and ravuconazole.
- Tamura, Keiji,Kumagai, Naoya,Shibasaki, Masakatsu
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supporting information
p. 3272 - 3278
(2014/05/06)
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- The process development of ravuconazole: An efficient multikilogram scale preparation of an antifungal agent
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The development of a safe, robust process for the preparation of ravuconazole (1), an antifungal agent, is described. The discovery and development of procedures enabling the efficient synthesis of multikilogram quantities of 1 and the process demonstration through plant scale preparations are presented. A controlled means to prepare a Grignard reagent and utilization of Fourier Transform Infrared spectroscopy (FTIR) monitoring to safely conduct the reaction is featured.
- Pesti, Jaan,Chen, Chien-Kuang,Spangler, Lori,DelMonte, Albert J.,Benoit, Serge,Berglund, Derek,Xbien, Derek,Brodfuehrer, Paul,Chan, Yeung,Corbett, Elisabeth,Costello, Carrie,DeMena, Paul,Discordia, Robert P.,Doubleday, Wendel,Gao, Zhinong,Gingras, Stephane,Grosso, John,Haas, Oscar,Kacsur, David,Lai, Chiajen,Leung, Simon,Miller, Melanie,Muslehiddinoglu, Jale,Nguyen, Nina,Qiu, Jun,Olzog, Martina,Reiff, Emily,Thoraval, Dominique,Totleben, Michael,Vanyo, Dale,Vemishetti, Purushotham,Wasylak, John,Wei, Chenkou
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experimental part
p. 716 - 728
(2010/04/22)
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- Enzyme-catalysed approach to the preparation of triazole antifungals: synthesis of (-)-genaconazole
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The work describes a new enzyme-mediated approach to optically active epoxide (2R,3S)-6, which is an important key intermediate in the preparation of single enantiomers of chiral azole antifungals. The conversion of (2R,3S)-6 into (-)-genaconazole is reported as an example of its synthetic relevance.
- Acetti, Daniela,Brenna, Elisabetta,Fuganti, Claudio,Gatti, Francesco G.,Serra, Stefano
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experimental part
p. 2413 - 2420
(2010/03/24)
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- Discovery of novel indazole-linked triazoles as antifungal agents
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The in vitro and in vivo activities of a series of (2R, 3R)-2-(2,4-difluorophenyl)-3-(substituted indazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol as potential antifungal agents are described. In particular, the analog 12j having 5-bromo substitution on the indazole ring exhibited significant antifungal activity against a variety of fungal cultures (Candida spp. and Aspergillus spp.). In addition, oral administration of 12j showed its excellent efficacy against Candida albicans in a murine infection model and the significantly improved survival rates of the infected mice.
- Park, Joon Seok,Yu, Kyung A,Kang, Tae Hee,Kim, Sunghoon,Suh, Young-Ger
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p. 3486 - 3490
(2008/02/11)
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- PROCESS FOR PRODUCING EPOXYTRIAZOLE DERIVATIVE
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This invention provides a process for producing an epoxytriazole derivative represented by formula (2): (wherein R and Ar are defined below), which comprises a step including a reaction of an epoxy derivative represented by formula (1'): (wherein R represents a hydrogen atom or C1-12 alkyl group and Ar represents an aromatic group optionally substituted by a halogen atom(s) or trifluoromethyl group(s), and X' represents a hydroxy group or leaving group), with 1,2,4-triazole in the presence of a base and water.
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Page/Page column 10
(2008/06/13)
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- PROCESS FOR PRODUCING EPOXYTRIAZOLE COMPOUND AND INTERMEDIATE THEREFOR
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The present invention provides a compound of the formula (I); wherein Ar represents difluorophenyl group, which is useful as an intermediate in a process for producing an epoxytriazole compound of the formula (VII); wherein Ar represents difluorophenyl group, which is a synthetic intermediate of antifungal agents. The present invention also provides a process for producing a compound of the formula (VII) which comprises epoxydation step, deprotection step, reaction step with a compound represented by RSO2X, and reaction step with 1,2,4-triazole; or comprises epoxydation step, reaction step with 1,2,4-triazole, deprotection step, reaction step with a compound represented by RSO2X and treatment step by a base.
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Page/Page column 25; 26
(2010/11/23)
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- OPTICALLY ACTIVE HALOHYDRIN DERIVATIVE AND PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY ALCOHOL DERIVATIVE FROM THE SAME
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The present invention provides an industrially safe, easily operable process for producing an optically active epoxy alcohol derivative useful as an intermediate for pharmaceuticals from inexpensively available materials, and also provides a novel halohydrin derivative serving as an important intermediate for the epoxyalcohol derivative. Furthermore, the present invention provides a process for producing an intermediate for a triazole antifungal agent by allowing a halohydrin to react with a triazole sulfonamide, the process including a small number of steps. A process for producing an optically active epoxy alcohol derivative includes allowing an optically active α-substituted propionate derivative to react with a haloacetic acid derivative in the presence of a base to prepare an optically active haloketone derivative, allowing the resulting haloketone derivative to react with an aryl metal compound to stereoselectively prepare a halohydrin derivative, eliminating a substituent for the hydroxy group of the halohydrin derivative, and performing epoxidation with a base. Furthermore, a process for producing an intermediate for a triazole antifungal agent includes allowing a halohydrin derivative to react with a triazole sulfonamide, the process including a small number of steps.
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Page/Page column 30
(2008/06/13)
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- ANTIFUNGAL AZOLE DERIVATIVES HAVING A FLUOROVINYL MOIETY AND PROCESS FOR THE PREPARATION THEREOF
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An azole derivative of formula (I) having a fluorovinyl moiety or a pharmaceutically acceptable salt thereof is superior to the conventional antifungal drugs in antifungal activity against a wide spectrum of pathogenic fungi, and has advantageously low toxicity.
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Page/Page column 15
(2010/02/10)
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- Optically active antifungal azoles: Synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol
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A series of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]- ethyl}-tetrazol-2-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (11a-n) and (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl} -tetrazole-1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol (12a-n) has been synthesized. The antifungal activity of compounds was evaluated by in vitro agar diffusion and broth dilution assay. Compounds 11d and its positional isomer 12d having 3-trifluoromethyl substitution on the phenyl ring of piperazine demonstrated significant antifungal activity against variety of fungal cultures (Candida spp. C. neoformans and Aspergillus spp.). The compound 12d showed MIC value of 0.12μg/mL for C. albicans, C. albicans V-01-191A-261 (resistant strain); 0.25μg/mL for C. tropicalis, C. parapsilosis ATCC 22019 and C. krusei and MIC value of 0.5μg/mL for C. glabrata, C. krusei ATCC 6258, which is comparable to itraconazole and better than fluconazole. Further, compound 11d showed significant activity (MIC; 0.25-0.5μg/mL) against Candida spp. and strong anticryptococcal activity (MIC; 0.25μg/mL) against C. neoformans.
- Upadhayaya, Ram Shankar,Sinha, Neelima,Jain, Sanjay,Kishore, Nawal,Chandra, Ramesh,Arora, Sudershan K.
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p. 2225 - 2238
(2007/10/03)
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- Optically active antifungal azoles. XIII. Synthesis of stereoisomers and metabolites of 1-[(1Rr,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3(1H-1,2,4-triazol-1- yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456)
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1-[(1R,2R)-2-(2,4-Difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1- yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyll-2-imidazolidinone [(1R,2R)-1: TAK-456] is a new antifungal agent selected as a candidate for clinical trials. The three stereoisomers [(1S
- Ichikawa,Yamada,Yamaguchi,Kitazaki,Matsushita,Higashikawa,Itoh
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p. 1110 - 1119
(2007/10/03)
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- Asymmetric synthesis of SM-9164, a biologically active enantiomer of antifungal agent SM-8668
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SM-9164, a biologically active enantiomer of antifungal agent SM-8668, was prepared by asymmetric synthesis in 10 steps in 13% overall yield from commercially available 2-chloro-1-(2,4-difluorophenyl)ethanone. The crucial steps were Katsuki-Sharpless asymmetric epoxidation of the (E)-allylic alcohol and epimerization of the erythro-sulfone to the desired threo-isomer under basic conditions.
- Miyauchi, Hiroshi,Nakamura, Toshio,Ohashi, Naohito
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p. 2625 - 2632
(2007/10/03)
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- Stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668)
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The stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl )-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2-(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent and aqueous alkaline solution.
- Saji,Tamoto,Tanaka,Miyauchi,Fujimoto,Ohashi
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p. 1427 - 1433
(2007/10/02)
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- Optically active antifungal azoles. I. Synthesis and antifungal activity of (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol and its stereoisomers
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(2R,3R)-2-(2,4-Difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2- butanol [(2R,3R)-7] and its stereoisomers [(2S,3R)-, (2S,3S)- and (2R,3S)-7] were prepared from the optically active oxiranes 6 by a newly developed ring- opening reaction and evaluated for antifungal activity. The thiol (2R,3R)-7 showed extremely potent antifungal activity in vitro and in vivo. The optically active oxirane (2R,3S)-6, a useful intermediate for the synthesis of sulfur-containing antifungal azoles 5, was synthesized from methyl (R)- lactate [(R)-8] via eight steps in a stereocontrolled manner. The key step in the synthesis is the Grignard reaction of an amide derivative [(R)-12a] of (R)-lactic acid with 2,4-difluorophenyl-magnesium bromide (13).
- Tasaka,Tamura,Matsushita,Teranishi,Hayashi,Okonogi,Itoh
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p. 1035 - 1042
(2007/10/02)
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- Payne rearrangement route to the optically active oxirane precursor for the preparation of triazole antifungals
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Optically active epoxide 1, an important intermediate for the preparation of antifungal triazole-amides 2, was synthesized starting from the (S)-lactic acid-derived ketone 9 and taking advantage of the Payne rearrangement of the epoxyalcohol 8.
- Konosu,Miyaoka,Tajima,Oida
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p. 562 - 564
(2007/10/02)
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- Triazole antifungals. III. Stereocontrolled synthesis of an optically active triazolylmethyloxirane precursor to antifungal oxazolidine derivatives
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Stereocontrolled synthesis of an optically active triazolylmethyloxirane 2, an important intermediate for the preparation of antifungal oxazolidine compounds 1, was achieved by two methods using L-lactic acid as a starting material. The key intermediate ketone 6 used in the procedures also served for the synthesis of the enantiomer of 2 and the corresponding diastereomeric epoxide.
- Konosu,Miyaoka,Tajima,Oida
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p. 2241 - 2246
(2007/10/02)
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- Concise Synthesis of Optically Active Oxirane Precursors for the Preparation of Triazole Antifungals Using the Friedel-Crafts Reaction of (S)-2-Tosyloxypropionyl Chloride
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Optically active epoxide (2R,3S)-4, a key intermediate for the preparation of triazole antifungal agents (4R,5R)-1 and (2R,3R)-2 (X = 2,4-F2), was synthesized.The Friedel-Crafts reaction between the (S)-lactic acid derivative (S)-10 and m-difluorobenzene gave the (R)-2-chloropropiophenone derivative (R)-11, which was converted into (2R,3R)-18 via Peterson olefination, stereoselective osmium(VIII) oxide oxidation, and mesylation.Treatment of (2R,3R)-18 with sodium triazolide gave (2R,3S)-4.Similarly, the 4-chlorophenyl analog (2R,3S)-4' was prepared.
- Konosu, Toshiyuki,Tajima, Yawara,Miyaoka, Takeo,Oida, Sadao
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p. 7545 - 7548
(2007/10/02)
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- Triazole derivatives, their preparation and their use as fungicides
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Compounds of formula (I): in which: Ar is optionally substituted phenyl; R1 is hydrogen or alkyl; X is optionally unsaturated alkylene, cycloalkylene or both; mis 0 or 1; -Yn-R2 is azido, phthalimido, 1-oxo-2,3-dihydro-2-isoindolyl, protected hydroxy or -OSO2R4 (in which R4 is alkyl group, haloalkyl or optionally substituted phenyl); or Y represents a group of formula -N(R5)CO-, -N(R5)CO-CH=CH-, -O-CO-, -O-CO-CH=CH-, -S-CO- or -S-CO-CH=CH- (in which R5 is hydrogen or alkyl); nis 0 or 1; R2 is alkyl, haloalkyl or optionally substituted phenyl, naphthyl or heterocyclic; and R3 is hydrogen; or R3 and -Xm-Yn-R2 together are a group of formula (II): in which R2 is as defined above, pis 0 or 1, and qis 0 or 1;, and acid addition salts thereof are fungicides, which find considerable value in the eradication of fungi in both agriculture and medicine.
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