DD218098A5 - Verfahren zur herstellung von triazol-derivaten - Google Patents

Verfahren zur herstellung von triazol-derivaten Download PDF

Info

Publication number: DD218098A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; alkoxy; formula; ethyl; compounds
Prior art date: 1982-09-30

Application number

DD83255229A

Other languages

German (de)

English (en)

Inventor

Geoffrey E Gymer

Kenneth Richardson

Cooper Kelvin

Original Assignee

Pfizer

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.)

1982-09-30

Filing date

1983-09-29

Publication date

1985-01-30

1983-02-02 Priority claimed from GB838302888A external-priority patent/GB8302888D0/en

1983-05-07 Priority claimed from GB838312624A external-priority patent/GB8312624D0/en

1983-09-29 Application filed by Pfizer filed Critical Pfizer

1985-01-30 Publication of DD218098A5 publication Critical patent/DD218098A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 17
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 45
-1 5-chloropyrid-2-yl group Chemical group 0.000 claims abstract description 19
125000001424 substituent group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 12
239000000417 fungicide Substances 0.000 abstract description 4
229910052757 nitrogen Inorganic materials 0.000 abstract description 4
229940042055 systemic antimycotics triazole derivative Drugs 0.000 abstract description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000000243 solution Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
238000004458 analytical method Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000284 extract Substances 0.000 description 6
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125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
230000000843 anti-fungal effect Effects 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
241000222122 Candida albicans Species 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
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239000002585 base Substances 0.000 description 4
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
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239000006071 cream Substances 0.000 description 4
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125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
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241000282412 Homo Species 0.000 description 3
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DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
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235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
JOKCRTQSVAOBSG-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-3-hydroxy-2-methyl-4-(1,2,4-triazol-1-yl)butanenitrile Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(C(C#N)C)CN1C=NC=N1 JOKCRTQSVAOBSG-UHFFFAOYSA-N 0.000 description 2
241001225321 Aspergillus fumigatus Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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241000233866 Fungi Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
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229910052783 alkali metal Inorganic materials 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical class [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
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XOHMICFWUQPTNP-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)CN1N=CN=C1 XOHMICFWUQPTNP-UHFFFAOYSA-N 0.000 description 1
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230000000391 smoking effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
238000005406 washing Methods 0.000 description 1
229940045860 white wax Drugs 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
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- 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

Landscapes

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

DD83255229A 1982-09-30 1983-09-29 Verfahren zur herstellung von triazol-derivaten DD218098A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8227978		1982-09-30
GB838302888A GB8302888D0 (en)	1983-02-02	1983-02-02	Antifungal agents
GB838312624A GB8312624D0 (en)	1983-05-07	1983-05-07	Triazole antifungal agents

Publications (1)

Publication Number	Publication Date
DD218098A5 true DD218098A5 (de)	1985-01-30

Family

ID=27261761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83255229A DD218098A5 (de)	1982-09-30	1983-09-29	Verfahren zur herstellung von triazol-derivaten

Country Status (16)

Country	Link
EP (1)	EP0106515B1 (fr)
KR (1)	KR880002208B1 (fr)
AU (1)	AU542694B2 (fr)
DD (1)	DD218098A5 (fr)
DE (1)	DE3378764D1 (fr)
DK (1)	DK166622B1 (fr)
ES (1)	ES8504150A1 (fr)
FI (1)	FI85694C (fr)
GR (1)	GR81270B (fr)
HU (1)	HU194837B (fr)
IE (1)	IE56019B1 (fr)
IL (1)	IL69825A (fr)
NO (1)	NO164168C (fr)
NZ (1)	NZ205795A (fr)
PT (1)	PT77430B (fr)
YU (4)	YU195683A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001011145A1 (fr)	1999-08-09	2001-02-15	Maschinen & Anlagen Service Gmbh	Arbre a brosse pour le nettoyage de voies ferrees

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4610716A (en) *	1982-12-14	1986-09-09	Ciba-Geigy Corporation	Fluorinated azolyl ethanol growth regulators and microbicides
JPS6025990A (ja) *	1983-07-20	1985-02-08	Shionogi & Co Ltd	トリアゾ−ル系ジオキソラン誘導体
GB8322983D0 (en) *	1983-08-26	1983-09-28	Pfizer Ltd	Triazole antifungal agents
CN1008735B (zh) *	1984-11-02	1990-07-11	拜尔公司	以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物
GB8510195D0 (en) *	1985-04-22	1985-05-30	Ici Plc	Heterocyclic compounds
GB8601952D0 (en) *	1986-01-28	1986-03-05	Ici Plc	Heterocyclic compounds
AU2811689A (en) *	1987-11-20	1989-06-14	Schering Corporation	Tri-and tetra-substituted-oxetanes and tetrahydrofurans and intermediates thereof
DE3839170A1 (de) *	1988-11-19	1990-05-31	Bayer Ag	Cyclopropyl-substituierte azolylmethylcarbinole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US5134152A (en) *	1989-12-07	1992-07-28	Sankyo Company, Limited	Oxetane derivatives and their use as anti-fungal or fungicidal agents
DE59108747D1 (de) *	1990-10-17	1997-07-17	Hoechst Schering Agrevo Gmbh	Pyrimidin-Derivate, Verfahren zu ihrer Herstellung sie enthaltende Mittel und ihre Verwendung als Fungizide
GB9107055D0 (en) *	1991-04-04	1991-05-22	Pfizer Ltd	Triazole antifungal agents
JP3471831B2 (ja) *	1991-12-09	2003-12-02	富山化学工業株式会社	新規なトリアゾール誘導体およびその塩
DE4206529A1 (de) *	1992-03-02	1993-09-09	Bayer Ag	Azolylmethyl-cyclopropyl-derivate
CN1054853C (zh) *	1995-01-11	2000-07-26	上海三维制药公司	氟康唑中间体1－[2－(2,4－二氟苯基)2,3－环氧丙基]－1h－1,2,4－三氮唑及其甲磺酸盐的制备方法
CA2838586C (fr) *	2011-06-07	2016-10-11	Kureha Corporation	Derive azole, son procede de fabrication, compose intermediaire et agent chimique agricole ou horticole et agent de protection de matiere industrielle
PL2784067T3 (pl)	2011-11-25	2017-08-31	Kureha Corporation	Przeciwgrzybicze pochodne azolowe
PL3078265T3 (pl)	2013-12-05	2017-10-31	Kureha Corp	Substancja chemiczna do zastosowań rolniczych lub ogrodniczych, metoda ochrony roślin przed chorobami oraz produkt ochrony roślin przed chorobami
EP3078266A4 (fr)	2013-12-05	2016-11-23	Kureha Corp	Produit chimique agricole ou horticole, procédé de lutte contre les maladies de plantes et produit de lutte contre les maladies de plantes

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0046633A1 (fr) *	1980-08-22	1982-03-03	Imperial Chemical Industries Plc	Composés hétérocycliques utilisés comme pesticides et leur procédé de préparation
DE3048267A1 (de) *	1980-12-20	1982-07-15	Bayer Ag, 5090 Leverkusen	Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte
GR78234B (fr) *	1981-03-10	1984-09-26	Ciba Geigy Ag
EP0084236A3 (fr) *	1981-12-22	1983-08-03	Fbc Limited	Composés hétérocycliques fongiques et compositions les contenant
GB2120235A (en) *	1982-03-23	1983-11-30	Ici Plc	Triazole and imidazole derivatives having fungicidal and plant-growth regulating activity
GB8301699D0 (en) *	1983-01-21	1983-02-23	Pfizer Ltd	Antifungal agents

1983
- 1983-09-09 DE DE8383305278T patent/DE3378764D1/de not_active Expired
- 1983-09-09 EP EP83305278A patent/EP0106515B1/fr not_active Expired
- 1983-09-26 KR KR1019830004490A patent/KR880002208B1/ko not_active Expired
- 1983-09-27 IL IL69825A patent/IL69825A/xx not_active IP Right Cessation
- 1983-09-28 FI FI833496A patent/FI85694C/fi not_active IP Right Cessation
- 1983-09-28 NZ NZ205795A patent/NZ205795A/en unknown
- 1983-09-28 DK DK443683A patent/DK166622B1/da not_active IP Right Cessation
- 1983-09-29 ES ES526066A patent/ES8504150A1/es not_active Expired
- 1983-09-29 GR GR72582A patent/GR81270B/el unknown
- 1983-09-29 YU YU01956/83A patent/YU195683A/xx unknown
- 1983-09-29 NO NO833549A patent/NO164168C/no unknown
- 1983-09-29 PT PT77430A patent/PT77430B/pt not_active IP Right Cessation
- 1983-09-29 IE IE2302/83A patent/IE56019B1/en not_active IP Right Cessation
- 1983-09-29 AU AU19771/83A patent/AU542694B2/en not_active Ceased
- 1983-09-29 HU HU833388A patent/HU194837B/hu not_active IP Right Cessation
- 1983-09-29 DD DD83255229A patent/DD218098A5/de unknown
1985
- 1985-08-14 YU YU01296/85A patent/YU129685A/xx unknown
- 1985-08-14 YU YU01295/85A patent/YU129585A/xx unknown
- 1985-08-14 YU YU01297/85A patent/YU129785A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2001011145A1 (fr)	1999-08-09	2001-02-15	Maschinen & Anlagen Service Gmbh	Arbre a brosse pour le nettoyage de voies ferrees

Also Published As

Publication number	Publication date
AU542694B2 (en)	1985-03-07
EP0106515B1 (fr)	1988-12-28
YU129685A (en)	1986-02-28
NO833549L (no)	1984-04-02
FI833496A7 (fi)	1984-03-31
DK166622B1 (da)	1993-06-21
IE832302L (en)	1984-03-30
YU195683A (en)	1986-02-28
NO164168B (no)	1990-05-28
YU129585A (en)	1986-02-28
YU129785A (en)	1986-02-28
PT77430A (en)	1983-10-01
KR880002208B1 (ko)	1988-10-18
GR81270B (fr)	1984-12-11
EP0106515A2 (fr)	1984-04-25
KR840006221A (ko)	1984-11-22
FI85694C (fi)	1992-05-25
ES526066A0 (es)	1985-04-16
IL69825A (en)	1986-12-31
IE56019B1 (en)	1991-03-27
DE3378764D1 (en)	1989-02-02
NZ205795A (en)	1985-09-13
DK443683A (da)	1984-03-31
FI833496A0 (fi)	1983-09-28
NO164168C (no)	1990-09-05
FI85694B (fi)	1992-02-14
HU194837B (en)	1988-03-28
ES8504150A1 (es)	1985-04-16
DK443683D0 (da)	1983-09-28
PT77430B (en)	1986-04-17
EP0106515A3 (en)	1985-12-04
AU1977183A (en)	1984-04-05
IL69825A0 (en)	1983-12-30

Publication	Publication Date	Title
EP0043419B1 (fr)	1984-03-14	Composition antimycotique
DD218098A5 (de)	1985-01-30	Verfahren zur herstellung von triazol-derivaten
EP0015387B1 (fr)	1983-01-12	Dérivés du 1-vinyltriazole, procédé pour leur préparation ainsi que leur utilisation comme régulateurs de croissance et fongicides
EP0011769B1 (fr)	1982-04-14	Hydroxyéthyl azoles, procédé pour leur préparation ainsi que leur utilisation dans des médicaments
DE3202601A1 (de)	1983-08-04	Substituierte 1 -hydroxyalkyl-azolyl-derivate, verfahren zu ihrer herstellung sowie ihrer verwendung als fungizide und pflanzenwachstumsregulatoren
EP0011768B1 (fr)	1981-10-21	Hydroxypropyl triazoles, procédé pour leur préparation et médicaments contenant ces composés
DE3609596A1 (de)	1987-10-01	2-azolylmethyl-2-aryl-1,3-dioxolane und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung
DD145105A5 (de)	1980-11-19	Verfahren zur herstellung von 1-(2 aryl-4,5-disubstituierten-1,3-dioxolan-2-ylmethyl)-1h-i idazolen und-1h-1,2,4-triazolen
US4482558A (en)	1984-11-13	Antifungal amide and urea derivatives of (3-amino-2-aryl-2-hydroxyprop-1-yl)-1H-1,2,4-triazoles
EP0120276A1 (fr)	1984-10-03	Diazolylalkyl ou triazolylalkyl carbinols substitués, leur procédé de préparation et leur application comme agents antimycosiques
DD142838A5 (de)	1980-07-16	Fungizide mittel
DD207715A5 (de)	1984-03-14	Verfahren zur herstellung von triazol-derivaten
US4618616A (en)	1986-10-21	Cyclopropylidene antifungal agents
US4503063A (en)	1985-03-05	N-Acyl 3-aryl-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)-butyramide antifungal agents
DD216457A5 (de)	1984-12-12	Verfahren zur herstellung von triazolen
DE2918894A1 (de)	1980-11-20	Fluorierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DD224850A5 (de)	1985-07-17	Verfahren zur herstellung neuer bis-triazol-derivate
US4767777A (en)	1988-08-30	Triazole antifungal agents
DE3124580A1 (de)	1983-01-05	Fungizide mittel
DD246998A5 (de)	1987-06-24	Verfahren zur herstellung von triazol-derivaten
US5047548A (en)	1991-09-10	3-aryl-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butyramide and derivatives as antifungal agents
DD216928A5 (de)	1985-01-02	Verfahren zur herstellung neuer triazol-derivate
EP0104300B1 (fr)	1986-03-26	Diazolyl-alcanoles, procédé pour leur préparation et leur utilisation comme agents antimycotiques
EP0011770B1 (fr)	1981-10-14	Fluorényl-azolylméthyl-carbinols, procédé pour leur préparation médicaments contenant ces composés et procédé pour la préparation de ces médicaments
DD231789A5 (de)	1986-01-08	Verfahren zur herstellung von triazol-derivaten

DD218098A5 - Verfahren zur herstellung von triazol-derivaten - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (3)

Publications (1)

Family

ID=27261761

Family Applications (1)

Country Status (16)

Cited By (1)

Families Citing this family (18)

Family Cites Families (6)

Cited By (1)

Also Published As

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