HU195079B - Fungicide compositions containing 3-/1,2,4-triazol-1-yl/-1-propene derivatives as active components and process for producing these derivatives - Google Patents
Fungicide compositions containing 3-/1,2,4-triazol-1-yl/-1-propene derivatives as active components and process for producing these derivatives Download PDFInfo
- Publication number
- HU195079B HU195079B HU842866A HU286684A HU195079B HU 195079 B HU195079 B HU 195079B HU 842866 A HU842866 A HU 842866A HU 286684 A HU286684 A HU 286684A HU 195079 B HU195079 B HU 195079B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- optionally substituted
- phenyl
- triazol
- weight
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims description 3
- 230000000855 fungicidal effect Effects 0.000 title abstract description 8
- 239000000203 mixture Substances 0.000 title description 40
- 238000000034 method Methods 0.000 title description 16
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 title description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- IADAMWWRAKRHRW-UHFFFAOYSA-N 1-prop-2-enyl-1,2,4-triazole Chemical class C=CCN1C=NC=N1 IADAMWWRAKRHRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 methoxy, tert-butyl Chemical group 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 239000003085 diluting agent Substances 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004575 stone Substances 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 235000013312 flour Nutrition 0.000 claims description 5
- KQQIIJSWEPRYPF-UHFFFAOYSA-N 1,3-bis(1,2,4-triazol-1-yl)propan-2-one Chemical compound C1=NC=NN1CC(=O)CN1C=NC=N1 KQQIIJSWEPRYPF-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 229910052751 metal Chemical class 0.000 abstract description 2
- 239000002184 metal Chemical class 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000005346 substituted cycloalkyl group Chemical group 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 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 47
- 241000196324 Embryophyta Species 0.000 description 30
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- 230000001681 protective effect Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 16
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 235000011167 hydrochloric acid Nutrition 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
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- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
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- 239000011541 reaction mixture Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000004808 allyl alcohols Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
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- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YTDLODZOJUYDKO-UHFFFAOYSA-N 1-[2-(bromomethyl)-3,3-dimethylbut-1-enyl]-2,4-dichlorobenzene Chemical compound CC(C)(C)C(CBr)=CC1=CC=C(Cl)C=C1Cl YTDLODZOJUYDKO-UHFFFAOYSA-N 0.000 description 2
- UAJPOQIIWXRQHZ-UHFFFAOYSA-N 1-[3-(2,4-dichlorophenyl)prop-2-enyl]-1,2,4-triazole Chemical compound ClC1=C(C=CC(=C1)Cl)C=CCN1N=CN=C1 UAJPOQIIWXRQHZ-UHFFFAOYSA-N 0.000 description 2
- DMCCATRZGWKQGB-UHFFFAOYSA-N 2,4-dichloro-1-(2,3,3-trimethylbut-1-enyl)benzene Chemical compound CC(C)(C)C(C)=CC1=CC=C(Cl)C=C1Cl DMCCATRZGWKQGB-UHFFFAOYSA-N 0.000 description 2
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- 241000190150 Bipolaris sorokiniana Species 0.000 description 2
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- 150000001299 aldehydes Chemical class 0.000 description 2
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
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- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
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- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
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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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- 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)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833327036 DE3327036A1 (de) | 1983-07-27 | 1983-07-27 | 3-(1,2,4-triazol-1-yl)-l-propene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT35157A HUT35157A (en) | 1985-06-28 |
| HU195079B true HU195079B (en) | 1988-04-28 |
Family
ID=6205031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU842866A HU195079B (en) | 1983-07-27 | 1984-07-25 | Fungicide compositions containing 3-/1,2,4-triazol-1-yl/-1-propene derivatives as active components and process for producing these derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4740515A (enEXAMPLES) |
| EP (1) | EP0132730B1 (enEXAMPLES) |
| JP (1) | JPS6042370A (enEXAMPLES) |
| KR (1) | KR850001176A (enEXAMPLES) |
| AT (1) | ATE34387T1 (enEXAMPLES) |
| AU (1) | AU568383B2 (enEXAMPLES) |
| BR (1) | BR8403715A (enEXAMPLES) |
| CA (1) | CA1234124A (enEXAMPLES) |
| DE (2) | DE3327036A1 (enEXAMPLES) |
| DK (1) | DK365384A (enEXAMPLES) |
| ES (1) | ES534630A0 (enEXAMPLES) |
| GR (1) | GR82264B (enEXAMPLES) |
| HU (1) | HU195079B (enEXAMPLES) |
| IL (1) | IL72493A (enEXAMPLES) |
| NZ (1) | NZ208984A (enEXAMPLES) |
| PT (1) | PT78928B (enEXAMPLES) |
| ZA (1) | ZA845782B (enEXAMPLES) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH064598B2 (ja) * | 1986-07-01 | 1994-01-19 | 塩野義製薬株式会社 | アゾ−ル誘導体、およびそれを含有する植物病害防除剤 |
| GB8716650D0 (en) * | 1987-07-15 | 1987-08-19 | Ici Plc | Use of olefinic compounds |
| DE3805684A1 (de) * | 1988-02-24 | 1989-09-07 | Basf Ag | Azolylmethylcycloalkyloxirane, ihre herstellung und verwendung als pflanzenschutzmittel |
| DE3811916A1 (de) * | 1988-04-09 | 1989-10-19 | Basf Ag | Azolylalkene und diese enthaltende fungizide |
| DE3825586A1 (de) * | 1988-07-28 | 1990-02-01 | Basf Ag | Substituierte imidazolylmethyloxirane und substituierte imidazolylpropene, ihre herstellung und sie enthaltende fungizide |
| DE3825841A1 (de) * | 1988-07-29 | 1990-02-01 | Basf Ag | 1-halogen-1-azolypropene und -methyloxirane und diese enthaltende fungizide |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2547953A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2652313A1 (de) * | 1976-11-17 | 1978-05-18 | Basf Ag | Triazolderivate |
| DE2833194A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Triazolderivate |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| DE3100261A1 (de) * | 1981-01-08 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | Keten-o,n-acetale, verfahren zu ihrer herstellung, diese enthaltende fungizide und ihre verwendung zur bekaempfung von pilzen |
| DE3103068A1 (de) * | 1981-01-30 | 1982-08-26 | Basf Ag, 6700 Ludwigshafen | Vinylazole, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von pilzen |
| DE3267642D1 (en) * | 1981-03-10 | 1986-01-09 | Ciba Geigy Ag | Process for the preparation of phenylethyl triazoles |
| GR78234B (enEXAMPLES) * | 1981-03-10 | 1984-09-26 | Ciba Geigy Ag | |
| DE3130215A1 (de) * | 1981-07-31 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | Phenylketenacetale und diese enthaltende fungizide |
| EP0094167A3 (en) * | 1982-05-12 | 1984-07-04 | Fbc Limited | Azolyl fungicide and plant growth regulators and compositions containing them |
| DE3218130A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide |
-
1983
- 1983-07-27 DE DE19833327036 patent/DE3327036A1/de not_active Withdrawn
-
1984
- 1984-07-14 AT AT84108291T patent/ATE34387T1/de not_active IP Right Cessation
- 1984-07-14 DE DE8484108291T patent/DE3471304D1/de not_active Expired
- 1984-07-14 EP EP84108291A patent/EP0132730B1/de not_active Expired
- 1984-07-16 AU AU30709/84A patent/AU568383B2/en not_active Ceased
- 1984-07-17 PT PT78928A patent/PT78928B/pt unknown
- 1984-07-18 US US06/632,138 patent/US4740515A/en not_active Expired - Fee Related
- 1984-07-23 JP JP59151465A patent/JPS6042370A/ja active Pending
- 1984-07-24 NZ NZ208984A patent/NZ208984A/en unknown
- 1984-07-25 IL IL72493A patent/IL72493A/xx unknown
- 1984-07-25 HU HU842866A patent/HU195079B/hu unknown
- 1984-07-25 GR GR75418A patent/GR82264B/el unknown
- 1984-07-25 CA CA000459652A patent/CA1234124A/en not_active Expired
- 1984-07-26 ES ES534630A patent/ES534630A0/es active Granted
- 1984-07-26 DK DK365384A patent/DK365384A/da not_active Application Discontinuation
- 1984-07-26 BR BR8403715A patent/BR8403715A/pt unknown
- 1984-07-26 ZA ZA845782A patent/ZA845782B/xx unknown
- 1984-07-27 KR KR1019840004466A patent/KR850001176A/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE34387T1 (de) | 1988-06-15 |
| DE3471304D1 (de) | 1988-06-23 |
| GR82264B (enEXAMPLES) | 1984-12-13 |
| EP0132730B1 (de) | 1988-05-18 |
| DK365384D0 (da) | 1984-07-26 |
| DE3327036A1 (de) | 1985-02-07 |
| JPS6042370A (ja) | 1985-03-06 |
| US4740515A (en) | 1988-04-26 |
| CA1234124A (en) | 1988-03-15 |
| DK365384A (da) | 1985-01-28 |
| NZ208984A (en) | 1986-11-12 |
| IL72493A (en) | 1988-06-30 |
| HUT35157A (en) | 1985-06-28 |
| AU568383B2 (en) | 1987-12-24 |
| KR850001176A (ko) | 1985-03-16 |
| BR8403715A (pt) | 1985-07-02 |
| PT78928B (de) | 1986-06-02 |
| IL72493A0 (en) | 1984-11-30 |
| PT78928A (de) | 1984-08-01 |
| EP0132730A1 (de) | 1985-02-13 |
| AU3070984A (en) | 1985-01-31 |
| ES8504744A1 (es) | 1985-05-01 |
| ES534630A0 (es) | 1985-05-01 |
| ZA845782B (en) | 1985-03-27 |
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