AU603417B2 - Oxiranes as synthetic intermediates - Google Patents

Oxiranes as synthetic intermediates Download PDF

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AU603417B2
AU603417B2 AU10752/88A AU1075288A AU603417B2 AU 603417 B2 AU603417 B2 AU 603417B2 AU 10752/88 A AU10752/88 A AU 10752/88A AU 1075288 A AU1075288 A AU 1075288A AU 603417 B2 AU603417 B2 AU 603417B2
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fluorine
phenyl
hydrogen
alkyl
substituted
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AU1075288A (en
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Alfred Meyer
Elmar Sturm
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Novartis AG
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Ciba Geigy AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

y~J 3 4 17 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Complete Specification Lodged: Accepted: Published: Class Int Class 'II. ,J 1 the pri;t i Priority: 4 Related Art: S Name and Address of Applicant: Ciba-Geigy AG Klybeckstrasse 141 4002 Basle
SWITZERLAND
Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Address for Service: Complete Specification for the invention entitled: Oxiranes As Synthetic Intermediates The following statement is a full description of this inventicG, including the best method of performing it known to me/us t' OXIRANES AS SYNTHETIC INTERMEDIATES The present invention relates to novel oxiranes valuable as intermediates in the preparation of novel l-azolyl-2-aryl-3-fluoroalkan-2ols and ethers thereof which possess microbicidal properties. The invention furthermore relates to processes for the manufacture of said oxiranes.
The novel microbicidal end products mentioned above are the subject of our co-pending application AU 22345/83 and correspond to the general formula I
OR
1
R
2 10 Az-CH 2
(I)
0. 0 o o O 0 0 SAr R 3 o in which Az is lH-l,2,4-triazole, 4H-1,2,4-triazole or IH-imidazole; Ar is an unsubstituted or substituted aromatic radice a from the series comprising 0ooo phenyl, biphenyl, phenoxyphenyl and naphthyl; R 1 is hydrogen, C-C 4 alkyl, C 3
-C
5 -alkenyl or benzyl; R 2 is hydrogen, fluorine or C -C 6 alkyl and R 3 is hydrogen, fluorine, C 1
-C
6 -alkyl, C -C 6 -haloalkyl,
C
1
-C
6 -alkoxy, C -C 6 -alkylthio, phenyl, phenoxy, phenylthio or S C 3
-C
7 -cycloalkyl, and each aromatic substltuent or aromatic moiety of a substituent is unsubstiluted or mono- or poly-substituted by halogen, C, L 1
-C
4 alkyl, C 1
-C
4 -alkoxy, C 1
-C
4 -haloaikyl, nitro and/or cyano; including the acid addition salts, quaternary azolium salts and metal complexes with the proviso that R 2 and R 3 cannot simultaneously be fluorine, The term alkyl by itself or as a constituent of another substituent is to be understood as meaning, for example, one of the following groups, depending on the number of carbon atoms stated; methyl, ethyl, propyl, butyl, pentyl, hexyl and the like and their isomers, for example isopropyl, isobutyl, tert.-butyl, isopentyl and the like, Haloalkyl is a ronohalogenated to perhalogenated alkyl substituent, for example CHC12,
CHF
2
CH
2 CI, CCI 3
CH
2 F, CH 2
CH
2 C1, CH 2 Br and the like, in particular CF 3 Here and in the following text, halogen is to be understood as meaning fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. Alkenyl is, for example, prop-l-enyl, allyl, but-l-enyl, but-?-enyl or but-3-enyl. Naphthyl is a-or 3naphthyl.
The use of the compounds of the present invention in the preparation of the compounds of formula I is described in AU 22345/83.
SD/22m -2 SD/227m 2 _i In accordance with one aspect of the present invention there is provided a novel oxirane of the formula II 0
I/\
Ar- C CH2 (I)D
R
2 C- R 3
I
F
in which Ar is an unsubstituted or substituted aromatic radic0l from the series comprising phenyl, biphenyl, phenoxyphenyl and naphthyl; R 2 is hydrogen, fluorine or C 1
-C
6 -alkyl and R 3 is hydrogen, fluorine,
C
1 -C6-alkyl, C -C6-haloalkyl, C 1
-C
6 -alkoxy, Ci-C 6 -alkylthio, K phenyl, phenoxy, phenylthio or C 3
-C
7 -cycloalkyl, and each aromatic 0o substituent or aromatic moiety of a substituent is unsubstituted or mono- 0 0 0 1°lb or poly-substituted by haloge, C 1
-C
4 -alkyl, C -C4-alkoxy, o 0
C-C
4 -haloalkyl, nitro and/or cyano.
o 1 4 SoooO Preferred compounds of formula II are those which can yield end .o 0 products of formula I with marked microbicidal, in particular phytofungicidal properties. Accordingly the following substances are preferred: compounds of formula II in which Ar is an unsubstituted or 0 0o 0o 0substituted aromatic radical from the series comprising phenyl, biphenyl 0o and phenoxyphenyl; R 2 is hydrogen, fluorine or C -C3-alkyl; and R is hydrogen, fluorine, C 1
-C
4 -alkyl, C 1
-C
3 -haloalkyl, C -C 3 o alkoxy, C -C 3 -alkylthio, phenyl, phenoxy or phenylthio, each phpnyl moiety being unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy, CF3, NO 2 and/or cyano.
oo a 3 2 o o Particularly preferred are compounds of the formula II in which; Ar °°oi is phenyl or phenoxyphenyl which is unsubstituted or preferably substituted in the 2- and/or 4-position by methyl or halogen; R 2 is hydrogen, fluorine or methyl; and R 3 is hydrogen, fluorine, C 1
-C
4 -alkyl or a radical from the series comprising phenyl, phenoxy and phenylttilo which is substituted by fluorine, chlorine and/or bromine.
The oxiranes of the formula II are novel, and are Intermediates which have been developed particularly for the preparation of the useful active substances of the formula I. Because of their structural nature, they can be converted into the compounds of the formula I in a simple manner, and, moreover, some of the compounds of the formula II have a fungicidal activity towards harmful fungi from the families of Ascomycetes, Basidiomycetes or Fungi imperfecti. Ascomycetes Include yeasts and moulds whilst Basidiomycetes includes fungi capable of causing damage to cereal crops. Almost all fungi pathogenic to man are members of the family Fungi SD/227m 3
I
imperfecti.
The invention thus relates to fungicidal compositions and to the use of compounds of formula II for the control of harmful fungi on plants or crops or in other situations where control is required.
The present invention furthermore relates to pharmaceutical compositions and to the use of the compounds of the invention in the treatment of fungal diseases in man or animals.
The fungicidal and pharmaceutical compositions of the invention include carriers, diluents, adjuvants etc known to those skilled in the respective arts and may be formulated as, for example, wettable powders, solutions, granules, dusts, emulsions, etc suitable for agricultural use, Sor as creams, solutions or other forms suited to pharmaceutical use.
Oxiranes of the formula II can be prepared from ketones of the formula III R2 Ar--C-C -F
(III
I II 0 R 3 Sin a manner which is known per se by reaction with dimethylsulfonium methylide or dimethyloxosulfonium methylide (Corey and Chaykovsky, JACS, 1 1962, 84, 3782).
The ketones of the formula III are accessible by methods which are known per se from the literature (cf. J. Leroy, J. Org. Chem. 46, 206 (1981) or Houben-Neyl, volume V/3, page 211), from the corresponding known 1 -bromo-ketones by conventional replacement of the bromine by fluorine, or they can also be prepared by acylation of the aromatic on which they are based with fluorinated carboxylic acid derivatives, for example by a Friedel-Crafts reaction.
In principle, unless expressly specified in a particular case, one or more solvents or diluents which are inert in the reaction can be present in the preparation of all the starting substances, intermediates and end products mentioned here. Examples of suitable solvents or diluents are aliphatic and aromatic hydrocarbons, such as benzene, toluene, the xylenes and petroleum ether; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride and tetrachloroethylene; ethers and ether-like compounds, such as dialkyl ethers (diethyl ether, dilsopropyl ether, tert.-butyl methyl ether and the like), anisole, dioxane and tetrahydrofuran; nitriles, such as acetonitrile and proplonitrile; N,N-dialkylated amides, such as dimethylformamide; SD/227m 4 I dimethylsulfoxide; ketones, such as acetone, diethyl ketone and methyl ethyl ketone, and mixtures of these solvents with one another. In some cases, it may also be advantageous to carry out the reaction or part steps of a reaction under a protective gas atmosphere and/or in absolute solvents.
Suitable protective gases dre inert gases, such as nitrogen, helium, argon or, in certain cases, also carbon dioxide.
The examples which follow serve to illustrate the invention in more detail without restricting it. Temperatures are in degrees centigrade.
Percentages and parts are by weight. In a'ddition, the following symbols are used: h hour; d day; min. minute; RT room temperature; N normality; abs absolute, anhydrous; DMSO dimethylsulfoxide; and DMF dimethylformamide. Pressures are given in millibar mb or bar b.
/227 C Ct SD/227m 5
I
Example 1 /Cl e* 0H-C H 2 2-(2,4-Dichlorophenyl)-2-(l-fluoropropyl)-bxirane 8g of 80% Sodium hydride were suspended in 300ml of absolute DMSO.
68g of trimethyloxosulfonium iodide were introduced into this suspension in portions under a nitrogen atmosphere, while stirring. When the evolution of hydrogen had ended and the exothermic reaction had subsided, the mixture was stirred at RT for a further 2 hours. A solution of 57g of 1-(2,4-dichlorophenyl)-2-fluorobutanone in 100m1 of tetrahydrofuran was then added dropwise in the course of 30 minutes, and the resulting mixture was stirred for 3 hours and then diluted to five times its volume with icewater and extracted several times with diethyl ether. The combined extracts were washed with water, dried over sodium sulfate and freed from the solvent in vacuo. Yield: 55g in the form of a brown oil.
Example 2 /Cl C I 0 After the exothermic reaction had subsided, the mixture was stirred at RT for a further hour, a solution of 2-(2,4-dlchlorophenyl)-2-(4-chlorophenoxy)-2-fluoroethanone in 30ml of tetrahydrofuran was then added dropwise and the resulting mixture was stirred at 250 to 30 0 C for a further 5 hours and then poured onto 1 litre of water, The product was extracted with diethyl ether, the extracts were washed with water, dried over sodium sulfate and filtered and the filtrate was concentrated, Yield: 15g as a yellowish oil.
SD/227m 6

Claims (8)

1. A compound of the general formula II 0\ Ar C CH 2 (II) R 2 C R 3 F in which Ar is an unsubstituted or substituted aromatic radical from the series comprising phenyl, biphenyl, phenoxyphenyl and naphthyl; R 2 is hydrogen, fluorine or C -C 6 -alkyl and R 3 is hydrogen, fluorine, C, -C 6 -alk l, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, phenyl, phenoxy, phenylthio or C 3 -C 7 -cycloalkyl, and each aromatic substituent or aromatic moiety of a substituent is unsubstituted or mono- or poly-substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C-haloalkyl, nitro and/or cyano.
2. A compound of the formula II according to claim 1, in which Ar is an unsubstituted or substituted aromatic radical from the series comprising phenyl, biphenyl and phenoxyphenyl; R 2 is hydrogen, fluorine or C 1 -C 3 -alkyl; and 3 is hydrogen, fluorine, C 1 -C 4 -alkyl, C 1 -C 3 -haloalkyl, C -C 3 alkoxy, C 1 -C 3 alkylthio, phenyl, phenoxy or phenylthio, each phenyl moiety being unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy, CF 3 NO 2 and/or cyano.
3. A compound of the formula II according to claim 2, in which Ar is phenyl or phenoxyphenyl which is unsubstituted or substituted in the 2- and/or 4-position by methyl or halogen; R 2 is hydrogen, fluorine or methyl; and R 3 Is hydrogen, fluorine, C 1 -C 4 -alkyl or a radical from the series comprising phenyl, phenoxy and phenylthio which is substituted by fluorine, chlorine and/or bromine.
4. An oxlrane as herein described with reference to any one of the Examples. A process for the prepaiation of a compound of the formula II according to claim 1, which process comprises reacting a ketone of the formula III Ar- C- F (III) 0 R 3 with dimethylsulfonium methylide or dimethyloxosulfonlium methylTide. SD/227m 7 _i
6. A process for the preparation of an oxirane, substantially as herein described with reference to any one of the Examples. -7 rt,- 3 e
8. A fungicidal formulation comprising an effective amount o least one compound according to any one of claims 1 to 4 togeti with an agriculturally acceptable carrier or diluent tnerefor.
9. A pharmaceutical composition comprising f east one compound according to any 4 mw of claims 1 to 4 togethe th a pharmaceutically acceptabie carrier, diluent and/or adjuvn'f A method for the treatm nr'of a fungal disease in a patient in need of such treatment, whichim.thod comprises administering to said patient an effective aot of at least one compound according to any one of claims 1 to 4 o-aia composition according to claim 9.
11. nthod for control of fungi at a locus which method comprises applyjr at least one compound according to any one of claims 1 to 4 or a DATED this TWENTY-SECOND day of JANUARY 1988 S .Ciba-Geigy AG SPatent Attorneys for the Applicant SPRUSON FERGUSON i Ix cS. "ly TI SD/227m
AU10752/88A 1982-12-14 1988-01-22 Oxiranes as synthetic intermediates Ceased AU603417B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH7269/82 1982-12-14
CH726982 1982-12-14

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
AU22345/83A Division AU570659B2 (en) 1982-12-14 1983-12-13 1-azolyl-2-aryl-3-fluoroalkan-2-ols and ethers thereof

Publications (2)

Publication Number Publication Date
AU1075288A AU1075288A (en) 1988-07-28
AU603417B2 true AU603417B2 (en) 1990-11-15

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AU10752/88A Ceased AU603417B2 (en) 1982-12-14 1988-01-22 Oxiranes as synthetic intermediates

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Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8520027D0 (en) * 1985-08-09 1985-09-18 Ici Plc Insecticidal ethers
US4935436A (en) * 1989-01-23 1990-06-19 The Dow Chemical Company Substituted triazoles and their use as fungicides
US5140023A (en) * 1990-04-27 1992-08-18 G. D. Searle & Co. Azatetracycle compounds
JP3471831B2 (en) * 1991-12-09 2003-12-02 富山化学工業株式会社 Novel triazole derivatives and their salts
HU212424B (en) * 1993-09-23 1996-06-28 Richter Gedeon Vegyeszet New propan-2-ol derivatives substituted with triazole or imidazole and process for producing them
ES2159676T3 (en) * 1995-12-22 2001-10-16 Ss Pharmaceutical Co TRIAZOL DERIVATIVES WITH ANTIMICOTIC AND INTERMEDIATE ACTIVITY.
US6002028A (en) * 1995-12-22 1999-12-14 Ss Pharmaceutical Co., Ltd. Triazole derivative, preparation process thereof and pharmaceutical comprising the same as an effective ingredient
US5939448A (en) * 1996-06-21 1999-08-17 Ss Pharmaceutical Co., Ltd. Triazole derivative or salt thereof
TW438784B (en) * 1997-08-29 2001-06-07 Ssp Co Ltd Triazole derivative or salt thereof and pharmaceutical composition for treating mycosis containing the same
JP3638438B2 (en) 1997-12-26 2005-04-13 エスエス製薬株式会社 Triazole derivative or salt thereof, process for producing the same, and medicament containing the compound as an active ingredient
JP2004359646A (en) * 2003-06-09 2004-12-24 Ss Pharmaceut Co Ltd New azole derivative with antimycotic activity
CN103649057B (en) 2011-07-13 2016-05-11 巴斯夫农业公司 2-[2 haloalkyl-4-Phenoxyphenyl of antifungal replacement]-1-[1,2,4] triazol-1-yl alcohol cpd
JP2014520833A (en) * 2011-07-15 2014-08-25 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal phenylalkyl-substituted 2- [2-chloro-4- (4-chloro-phenoxy) -phenyl] -1- [1,2,4] triazol-1-yl-ethanol compounds
BR112014000319B1 (en) 2011-07-15 2019-05-14 Basf Se USES OF FORMULA I COMPOUNDS, COMPOUNDS, PHYTOPATHOGENIC FUNGI METHODS, FORMULA I COMPOUND PREPARATION PROCESSES AND AGROCHEMICAL COMPOSITION
EP2731934A1 (en) 2011-07-15 2014-05-21 Basf Se Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
EP2559688A1 (en) 2011-08-15 2013-02-20 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-butoxy-ethyl}-1h [1,2,4]triazole compounds
EP2744795B1 (en) * 2011-08-15 2015-12-30 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-cyclyl-ethyl}-1h [1,2,4]triazole compounds
EP2744793B1 (en) 2011-08-15 2015-10-14 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-ethoxy-ethyl}-1h- [1,2,4]triazole compounds
BR112014003412A2 (en) 2011-08-15 2017-03-14 Basf Se compounds of formula i, process, compounds of formula xii, viii and xi, agrochemical compositions, use and coated seed
PE20141393A1 (en) 2011-08-15 2014-10-22 Basf Se SUBSTITUTE 1- {2- [2-HALO-4- (4-HALOGEN-PHENOXY) -PHENYL] -2-ALUINYLOXY-ETHYL} -1H- [1,2,4] TRIAZOLE FUNGICIDE COMPOUNDS
CA2842262A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-3-methyl-butyl}-1h-[1,2,4]triazole compounds
JP2014524431A (en) 2011-08-15 2014-09-22 ビーエーエスエフ ソシエタス・ヨーロピア Bactericidal substituted 1- {2- [2-halo-4- (4-halogen-phenoxy) -phenyl] -2-alkoxy-hexyl} -1H- [1,2,4] triazole compounds
WO2013024083A1 (en) 2011-08-15 2013-02-21 Basf Se Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-2-alkynyl/alkenyl-ethyl}-1h-[1,2,4]triazole compounds
WO2014082871A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
EP2735563A1 (en) * 2012-11-27 2014-05-28 Basf Se Meta substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
EP2928873A1 (en) 2012-11-27 2015-10-14 Basf Se Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides
WO2014082879A1 (en) 2012-11-27 2014-06-05 Basf Se Substituted [1,2,4]triazole compounds
BR112015012003A2 (en) * 2012-11-27 2018-05-15 Basf Se compounds of formula I, composition, use of a compound, method for combating harmful fungi, seed, process for preparing the compounds and intermediate compounds
US20150313229A1 (en) 2012-11-27 2015-11-05 Basf Se Substituted [1,2,4] Triazole Compounds
MX2015008100A (en) 2012-12-20 2016-05-31 Basf Agro Bv Compositions comprising a triazole compound.
CN105008332A (en) * 2013-01-08 2015-10-28 巴斯夫欧洲公司 Substituted imidazole and (1,2,4)triazole compounds as fungicides
US9981931B2 (en) * 2013-01-09 2018-05-29 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10512267B2 (en) 2013-07-08 2019-12-24 BASF Agro, B.V. Compositions comprising a triazole compound and a biopesticide
EP2839745A1 (en) 2013-08-21 2015-02-25 Basf Se Agrochemical formulations comprising a 2-ethyl-hexanol alkoxylate
EA201990522A1 (en) * 2013-12-12 2019-07-31 Басф Агро Б.В. METHOD FOR PRODUCING SUBSTITUTED OXYRANES AND TRIAZOLE
CN106170205B (en) 2014-02-14 2020-01-17 巴斯夫农业公司 Emulsifiable concentrate comprising pesticide, fatty amide and lactamide
US10212934B2 (en) 2014-06-25 2019-02-26 BASF Agro B.V. Pesticidal compositions
CA2952896C (en) 2014-07-08 2022-10-18 BASF Agro B.V. Process for the preparation of substituted oxiranes and triazoles
US10206403B2 (en) 2014-07-14 2019-02-19 Basf Se Pesticidal compositions
PL3214937T3 (en) 2014-11-07 2024-10-14 Basf Se Pesticidal mixtures
EP3028573A1 (en) 2014-12-05 2016-06-08 Basf Se Use of a triazole fungicide on transgenic plants
WO2016174042A1 (en) 2015-04-27 2016-11-03 BASF Agro B.V. Pesticidal compositions
US10344008B2 (en) 2015-05-08 2019-07-09 BASF Agro B.V. Process for the preparation of terpinolene epoxide
EP3294700B1 (en) 2015-05-08 2020-01-29 BASF Agro B.V. A process for the preparation of limonene-4-ol
EP3111763A1 (en) 2015-07-02 2017-01-04 BASF Agro B.V. Pesticidal compositions comprising a triazole compound
EP3316692B1 (en) 2015-07-02 2021-03-17 BASF Agro B.V. Pesticidal compositions comprising a triazole compound
EP3429358A1 (en) 2016-03-16 2019-01-23 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits
UA125210C2 (en) 2016-03-16 2022-02-02 Басф Се Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals
WO2017157916A1 (en) 2016-03-16 2017-09-21 Basf Se Use of tetrazolinones for combating resistant phytopathogenic fungi on soybean
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EP3472138B1 (en) 2016-06-15 2020-08-26 BASF Agro B.V. Process for the epoxidation of a tetrasubstituted alkene
WO2018054832A1 (en) 2016-09-22 2018-03-29 Bayer Cropscience Aktiengesellschaft Novel triazole derivatives
CN109715622A (en) 2016-09-22 2019-05-03 拜耳作物科学股份公司 New triazole derivative and its purposes as fungicide
CA3052519A1 (en) 2017-02-08 2018-08-16 Andreas Gortz Triazolethione derivatives
US20200045967A1 (en) 2017-02-08 2020-02-13 Bayer Cropscience Aktiengesellschaft Novel triazole derivatives
BR112019016241A2 (en) 2017-02-08 2020-04-07 Bayer Cropscience Ag triazole derivatives and their use as fungicides
JP2020507579A (en) 2017-02-10 2020-03-12 バイエル アクチェンゲゼルシャフトＢａｙｅｒ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Composition for controlling harmful microorganisms containing 1- (phenoxy-pyridinyl) -2- (1,2,4-triazol-1-yl) -ethanol derivative
EP3421460A1 (en) 2018-03-15 2019-01-02 Bayer Aktiengesellschaft 2-[(4-alkylphenoxy)-pyridinyl]-1-(1,2,4-triazol-1-yl)alkan-2-ol fungicides
WO2020020813A1 (en) 2018-07-25 2020-01-30 Bayer Aktiengesellschaft Fungicidal active compound combinations
WO2020020816A1 (en) 2018-07-26 2020-01-30 Bayer Aktiengesellschaft Novel triazole derivatives
WO2020070050A1 (en) 2018-10-01 2020-04-09 Bayer Aktiengesellschaft Fungicidal 5-substituted imidazol-1-yl carbinol derivatives
EP3620053A1 (en) 2018-12-14 2020-03-11 Bayer Aktiengesellschaft Fungicidal active compound combinations

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6074686A (en) * 1985-08-09 1987-02-12 Imperial Chemical Industries Plc Insecticidal ethers
AU7420687A (en) * 1982-10-08 1987-10-01 Bayer Aktiengesellschaft Oxiranes
AU8299787A (en) * 1987-01-08 1988-07-14 Imperial Chemical Industries Plc Fluorinated ethers

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2912288A1 (en) * 1979-03-28 1980-10-09 Bayer Ag METHOD FOR PRODUCING HYDROXYETHYL AZOLES
NZ198085A (en) * 1980-08-18 1985-09-13 Ici Plc Regulation of plant growth with certain 2,2-di(hydrocarbyl)-1-(1,2,4-triazol-1-yl)ethan-2-ols
US4616027A (en) * 1982-08-14 1986-10-07 Pfizer Inc. Antifungal 1-aryl-1-fluoroalkyl-2-(1H-1,2,4-triazol-1-yl)ethanols
CS235337B2 (en) * 1982-08-14 1985-05-15 Pfizer Method of triazole derivatives production
DE3337937A1 (en) * 1982-10-28 1984-05-03 Sandoz-Patent-GmbH, 7850 Lörrach NEW AZOLE DERIVATIVES
JPS5998073A (en) * 1982-11-02 1984-06-06 フアイザ−・コ−ポレ−シヨン Triazole fungicide
DE3461637D1 (en) * 1983-02-16 1987-01-22 Pfizer Ltd Triazole antifungal agents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7420687A (en) * 1982-10-08 1987-10-01 Bayer Aktiengesellschaft Oxiranes
AU6074686A (en) * 1985-08-09 1987-02-12 Imperial Chemical Industries Plc Insecticidal ethers
AU8299787A (en) * 1987-01-08 1988-07-14 Imperial Chemical Industries Plc Fluorinated ethers

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