NL7907372A - Nieuwe antimicrobieele triazoolderivaten. - Google Patents

Nieuwe antimicrobieele triazoolderivaten. Download PDF

Info

Publication number: NL7907372A
Authority: NL; Netherlands
Prior art keywords: formula; phenyl; compound; triazole; halogen
Prior art date: 1978-10-06

Application number

NL7907372A

Other languages

English (en)

Dutch (nl)

Original Assignee

Janssen Pharmaceutica Nv

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.)

1978-10-06

Filing date

1979-10-04

Publication date

1980-04-09

1979-10-04 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1980-04-09 Publication of NL7907372A publication Critical patent/NL7907372A/nl

Links

230000000845 anti-microbial effect Effects 0.000 title description 3
229940042055 systemic antimycotics triazole derivative Drugs 0.000 title description 2
239000004599 antimicrobial Substances 0.000 title 1
-1 3-halo-2-propynyl Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 39
238000006243 chemical reaction Methods 0.000 claims description 28
229910052751 metal Inorganic materials 0.000 claims description 28
239000002184 metal Chemical class 0.000 claims description 28
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 22
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
238000000034 method Methods 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
239000011541 reaction mixture Substances 0.000 claims description 10
238000010992 reflux Methods 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
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238000003756 stirring Methods 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 7
239000002585 base Substances 0.000 claims description 7
238000009835 boiling Methods 0.000 claims description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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125000004385 trihaloalkyl group Chemical group 0.000 claims description 5
239000000654 additive Substances 0.000 claims description 4
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125000004429 atom Chemical group 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
150000000180 1,2-diols Chemical class 0.000 claims description 2
NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
150000004692 metal hydroxides Chemical class 0.000 claims description 2
150000004682 monohydrates Chemical class 0.000 claims description 2
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims description 2
BYIRPARYIJMTLP-UHFFFAOYSA-N 1-[[4-(butoxymethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical compound O1C(COCCCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 BYIRPARYIJMTLP-UHFFFAOYSA-N 0.000 claims 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
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229910013627 M-Si Inorganic materials 0.000 claims 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
ZFVNPQBTVHWDOK-UHFFFAOYSA-N nitric acid;1h-1,2,4-triazole Chemical compound O[N+]([O-])=O.C=1N=CNN=1 ZFVNPQBTVHWDOK-UHFFFAOYSA-N 0.000 description 7
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239000005995 Aluminium silicate Substances 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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240000005979 Hordeum vulgare Species 0.000 description 5
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150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
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230000001681 protective effect Effects 0.000 description 5
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FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 5
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239000004009 herbicide Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
150000004694 iodide salts Chemical group 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000010410 layer Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
OOSNUUSSUUDQNI-UHFFFAOYSA-N oxalic acid 1H-1,2,4-triazole Chemical compound C(C(=O)O)(=O)O.N1N=CN=C1 OOSNUUSSUUDQNI-UHFFFAOYSA-N 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940044654 phenolsulfonic acid Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000013138 pruning Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- 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
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals

Landscapes

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

NL7907372A 1978-10-06 1979-10-04 Nieuwe antimicrobieele triazoolderivaten. NL7907372A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US94932978A	1978-10-06	1978-10-06
US94932978		1978-10-06
US5364079		1979-06-29
US06/053,640 US4338327A (en)	1978-10-06	1979-06-29	Substituted 1-(2-aryl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazoles

Publications (1)

Publication Number	Publication Date
NL7907372A true NL7907372A (nl)	1980-04-09

Family

ID=26732083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907372A NL7907372A (nl)	1978-10-06	1979-10-04	Nieuwe antimicrobieele triazoolderivaten.

Country Status (26)

Country	Link
US (1)	US4338327A (cs)
AR (1)	AR224878A1 (cs)
AT (1)	AT381617B (cs)
AU (1)	AU529866B2 (cs)
BR (1)	BR7906455A (cs)
CA (1)	CA1137089A (cs)
CH (1)	CH648843A5 (cs)
CS (1)	CS228121B2 (cs)
DD (1)	DD150142A5 (cs)
DE (1)	DE2940133A1 (cs)
DK (1)	DK417379A (cs)
ES (1)	ES484797A1 (cs)
FR (1)	FR2438046A1 (cs)
GB (1)	GB2032921B (cs)
HU (1)	HU186347B (cs)
IE (1)	IE48685B1 (cs)
IL (1)	IL58407A (cs)
IT (1)	IT1164831B (cs)
MX (1)	MX5867E (cs)
NL (1)	NL7907372A (cs)
NZ (1)	NZ191719A (cs)
PT (1)	PT70280A (cs)
SE (1)	SE434641B (cs)
TR (1)	TR20859A (cs)
YU (1)	YU42196B (cs)
ZW (1)	ZW20279A1 (cs)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3039087A1 (de) *	1980-10-16	1982-05-19	Hoechst Ag, 6000 Frankfurt	1-(1,3-dioxolan-2-ylmethyl)-azole, ihre salze, verfahren zu ihrer herstellung und ihre verwendung
ATE14731T1 (de) *	1980-12-10	1985-08-15	Ciba Geigy Ag	Mikrobizide triazolylmethyldioxolane und deren herstellung.
DE3404819A1 (de) *	1984-02-10	1985-08-14	Ludwig Heumann & Co GmbH, 8500 Nürnberg	Neue 1,3-dioxolanylderivate, verfahren zu ihrer herstellung, ihre verwendung und diese verbindungen enthaltendes arzneimittel
DE3510203A1 (de) *	1985-03-21	1986-09-25	Bayer Ag, 5090 Leverkusen	Neue iodpropargylether, ein verfahren zu ihrer herstellung und ihre verwendung
IT1186784B (it) *	1985-11-04	1987-12-16	Montedison Spa	Azoliderivati ad attivita' antufungina
IT1204773B (it) *	1986-01-23	1989-03-10	Montedison Spa	Azolilderivati fungicidi
IT1196528B (it) *	1986-07-21	1988-11-16	Donegani Guido Ist	Azolilderivati ad attivita' antifungina
DE4132668C2 (de) *	1991-10-01	1993-09-30	Kammann Maschf Werner	Vorrichtung und Verfahren zum Dekorieren eines kegelförmigen Körpers
EP0937071A1 (en)	1996-11-12	1999-08-25	Sepracor, Inc.	2r,4s,s,s- and 2s,4r,s,s-hydroxyitraconazole
JP2001504121A (ja) *	1996-11-12	2001-03-27	セプラコール，インク．	２ｒ，４ｓ，ｒ，ｓ―および２ｓ，４ｒ，ｒ，ｓ―ヒドロキシイトラコナゾール―およびヒドロキシサパーコナゾール誘導体
US6147077A (en) *	1999-04-29	2000-11-14	Sepracor Inc.	2R,4S-hydroxyitraconazole isomers
CN101302213B (zh) *	2008-06-30	2012-07-25	寿光富康制药有限公司	顺式-2-(2，4-二氯苯基)-2-([1，2，4]-三唑-1-甲基)-[1，3]二氧戊环-4-甲基甲磺酸酯的制备方法
CN103275073B (zh) *	2013-06-20	2015-09-30	湖南大学	2-(1,2,4-三唑-1-甲基)-2-(苯并呋喃-5-基)-1,3-二氧戊环及其应用
CN115745719A (zh) *	2017-06-16	2023-03-07	罗地亚经营管理公司	用于芳基羧酸和脂族羧酸的催化脱羧交叉酮化的方法
EP3925957A4 (en) *	2019-02-15	2022-11-02	Tohoku University	1,3-DIOXOLANE DERIVATIVE
CN111848600B (zh) *	2020-07-30	2021-12-07	沈阳药科大学	2,4,4-三取代二氢噁唑衍生物及其用途

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4101665A (en) *	1975-10-06	1978-07-18	Janssen Pharmaceutica N.V.	1-(2-Ar-4-aryloxymethyl-1,3-dioxolan-2-ylmethyl)imidazoles
US4144346A (en) *	1977-01-31	1979-03-13	Janssen Pharmaceutica N.V.	Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4160841A (en) *	1977-01-31	1979-07-10	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles
US4218458A (en) *	1978-06-23	1980-08-19	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-aryloxy-methyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles

1979
- 1979-06-29 US US06/053,640 patent/US4338327A/en not_active Expired - Lifetime
- 1979-09-27 CA CA000336496A patent/CA1137089A/en not_active Expired
- 1979-10-01 NZ NZ191719A patent/NZ191719A/xx unknown
- 1979-10-02 YU YU2400/79A patent/YU42196B/xx unknown
- 1979-10-03 DE DE19792940133 patent/DE2940133A1/de not_active Ceased
- 1979-10-04 NL NL7907372A patent/NL7907372A/nl not_active Application Discontinuation
- 1979-10-04 AU AU51489/79A patent/AU529866B2/en not_active Ceased
- 1979-10-04 DK DK417379A patent/DK417379A/da not_active Application Discontinuation
- 1979-10-04 GB GB7934421A patent/GB2032921B/en not_active Expired
- 1979-10-04 PT PT70280A patent/PT70280A/pt unknown
- 1979-10-05 IL IL58407A patent/IL58407A/xx unknown
- 1979-10-05 AT AT0652379A patent/AT381617B/de not_active IP Right Cessation
- 1979-10-05 IT IT50480/79A patent/IT1164831B/it active
- 1979-10-05 IE IE1891/79A patent/IE48685B1/en not_active IP Right Cessation
- 1979-10-05 TR TR20859A patent/TR20859A/xx unknown
- 1979-10-05 SE SE7908279A patent/SE434641B/sv not_active IP Right Cessation
- 1979-10-05 HU HU79JA857A patent/HU186347B/hu not_active IP Right Cessation
- 1979-10-05 MX MX798420U patent/MX5867E/es unknown
- 1979-10-05 FR FR7924858A patent/FR2438046A1/fr active Granted
- 1979-10-05 ES ES484797A patent/ES484797A1/es not_active Expired
- 1979-10-05 CH CH9009/79A patent/CH648843A5/de not_active IP Right Cessation
- 1979-10-05 ZW ZW202/79A patent/ZW20279A1/xx unknown
- 1979-10-05 BR BR7906455A patent/BR7906455A/pt unknown
- 1979-10-08 CS CS796829A patent/CS228121B2/cs unknown
- 1979-10-08 AR AR278403A patent/AR224878A1/es active
- 1979-10-08 DD DD79216082A patent/DD150142A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1164831B (it)	1987-04-15
IT7950480A0 (it)	1979-10-05
AR224878A1 (es)	1982-01-29
AU5148979A (en)	1981-04-09
AU529866B2 (en)	1983-06-23
DK417379A (da)	1980-04-07
FR2438046A1 (fr)	1980-04-30
BR7906455A (pt)	1980-06-17
IE791891L (en)	1980-04-06
ZW20279A1 (en)	1981-05-20
IL58407A (en)	1984-08-31
FR2438046B1 (cs)	1983-03-25
ES484797A1 (es)	1980-09-01
NZ191719A (en)	1982-03-30
DD150142A5 (de)	1981-08-19
PT70280A (en)	1979-11-01
CS228121B2 (en)	1984-05-14
IE48685B1 (en)	1985-04-17
DE2940133A1 (de)	1980-04-17
IL58407A0 (en)	1980-01-31
HU186347B (en)	1985-07-29
AT381617B (de)	1986-11-10
SE7908279L (sv)	1980-04-07
GB2032921A (en)	1980-05-14
US4338327A (en)	1982-07-06
YU240079A (en)	1983-02-28
CH648843A5 (de)	1985-04-15
GB2032921B (en)	1983-01-19
YU42196B (en)	1988-06-30
MX5867E (es)	1984-08-15
TR20859A (tr)	1982-11-05
ATA652379A (de)	1986-04-15
CA1137089A (en)	1982-12-07
SE434641B (sv)	1984-08-06

Legal Events

Date	Code	Title
1980-06-25	BT	A notification was added to the application dossier and made available to the public
1985-01-01	A85	Still pending on 85-01-01
1986-11-03	BA	A request for search or an international-type search has been filed
1986-11-03	BB	A search report has been drawn up
1986-12-01	BC	A request for examination has been filed
1991-06-03	BV	The patent application has lapsed

Publication	Publication Date	Title
FI83776C (fi)	1991-08-26	Som mikrobicider anvaenda 1-azolyl -2-aryl-3-fluoalkan-2-oler.
NL7907372A (nl)	1980-04-09	Nieuwe antimicrobieele triazoolderivaten.
CA1215989A (en)	1986-12-30	Substituted 1-hydroxyethyl-triazolyl derivatives
US4329342A (en)	1982-05-11	1-(2-Aryl-4,5-disubstituted-1,3-dioxolan-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles
AU593337B2 (en)	1990-02-08	New hydroxyalkylazolyl derivatives
DK157866B (da)	1990-02-26	1-aryloxyphenyl-2-azolyl-ethanon-derivater eller syreadditionssalte eller komplekser med uorganiske eller organiske metalsalte deraf samt en fremgangsmaade til bekaempelse eller beskyttelse af kulturplanter mod angreb af fytopatogene mikroorganismer
US4939162A (en)	1990-07-03	1-(2-aryl-1,3-dioxon-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles
US4690942A (en)	1987-09-01	1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers, composition containing them, and use of them to control phytopathogenic microorganisms
CA1150277A (en)	1983-07-19	Fluorinated 1-triazolyl-butane derivatives, a process for their preparation and their use as fungicides
NZ208847A (en)	1986-10-08	Fungicidal compositions containing diazole and triazole derivatives
CA1132579A (en)	1982-09-28	Halogenated 1-azolyl-1-fluorophenoxy- butane derivatives, a process for their preparation and their use as fungicides
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JPS6328916B2 (cs)	1988-06-10
JPS5890565A (ja)	1983-05-30	殺菌剤組成物
JPS6344154B2 (cs)	1988-09-02
CA1097354A (en)	1981-03-10	2,4-dichlorophenyl-triazolyl-ethan-ones and -ols, and their use as fungicides
CA1106757A (en)	1981-08-11	Fungicidal agents
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JPS6344155B2 (cs)	1988-09-02
JPS6128674B2 (cs)	1986-07-01
JPH0121147B2 (cs)	1989-04-19
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CS208118B2 (en)	1981-08-31	Fungicide means and method of making the active substances