FI77458B - Nya mikrobicida arylfenyleterderivat, foerfarande foer deras framstaellning och deras anvaendning. - Google Patents
Nya mikrobicida arylfenyleterderivat, foerfarande foer deras framstaellning och deras anvaendning. Download PDFInfo
- Publication number
- FI77458B FI77458B FI821572A FI821572A FI77458B FI 77458 B FI77458 B FI 77458B FI 821572 A FI821572 A FI 821572A FI 821572 A FI821572 A FI 821572A FI 77458 B FI77458 B FI 77458B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- formula
- phenyl
- halogen
- compound
- Prior art date
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- 229940124561 microbicide Drugs 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 121
- -1 C3-C4-alkenyl Chemical group 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052751 metal Chemical class 0.000 claims description 21
- 239000002184 metal Chemical class 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 8
- 230000003032 phytopathogenic effect Effects 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- PSDXWJUGKAUIKY-UHFFFAOYSA-N 1-[[4-ethyl-2-(4-phenoxyphenyl)-1,3-dioxan-2-yl]methyl]-1,2,4-triazole Chemical group O1C(CC)CCOC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 PSDXWJUGKAUIKY-UHFFFAOYSA-N 0.000 claims description 2
- CWRLLCKWYVWFSC-UHFFFAOYSA-N 1-[[4-ethyl-2-(4-phenoxyphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical group O1C(CC)COC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 CWRLLCKWYVWFSC-UHFFFAOYSA-N 0.000 claims description 2
- KALBJJADLJSROW-UHFFFAOYSA-N 1-[[4-methyl-2-(4-phenoxyphenyl)-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical group O1C(C)COC1(C=1C=CC(OC=2C=CC=CC=2)=CC=1)CN1N=CN=C1 KALBJJADLJSROW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 230000012010 growth Effects 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 229910052705 radium Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- FFVXOZCQKGDMFL-UHFFFAOYSA-N 1-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-ethyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole Chemical group O1C(CC)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 FFVXOZCQKGDMFL-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 112
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000004480 active ingredient Substances 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 241000196324 Embryophyta Species 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000460 chlorine Substances 0.000 description 35
- 125000001309 chloro group Chemical group Cl* 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 125000001246 bromo group Chemical group Br* 0.000 description 12
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000003905 agrochemical Substances 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 239000011572 manganese Substances 0.000 description 11
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- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 240000005979 Hordeum vulgare Species 0.000 description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 230000002538 fungal effect Effects 0.000 description 10
- 229910017604 nitric acid Inorganic materials 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- 239000005995 Aluminium silicate Substances 0.000 description 8
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- 229910052794 bromium Inorganic materials 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 241000209140 Triticum Species 0.000 description 6
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
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- 150000003254 radicals Chemical class 0.000 description 6
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
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- 229910021380 Manganese Chloride Inorganic materials 0.000 description 4
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 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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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
-
- 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
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- 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
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- 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
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- 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
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- 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
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
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Claims (9)
1. Föreningar med formeln I „... Α-ώ X Ας! i vilken formel Y betecknar gruppen -CH= eller -N=, Ra och Rjj betecknar oberoende av varandra väte, halogen, Ci-C3~alkyl, Ci-C3~alkoxi eller nitro; Ar betecknar osubstituerad eller med halogen, C^-Cy-alkyl, Ci~C7-alkoxi, nitro och/eller CF3 en eller flera gänger subs-tituerad fenyl; U och V betecknar oberoende av varandra eventuellt med halogen eller C].-Cg-alkoxi substituerad eller de bildar tillsammans en av de följande alkylenbryggorna "k A V/1 kv- · · eller H \ ' ' . -+-Rs \H/ s*~\ varvid Rl och R2 betecknar oberoende av varandra väte, » en eller flera gänger med halogen substituerad Ci-Ci2"a^^y^· · fenyl, en eller flera gänger med halogen och/eller C1-C3-alkyl substituerad fenyl eller gruppen -CH2-Z-R7, varvid Z betecknar syre eller svavel och R7 väte, C^-alkyl, med substitue- 122 7 7458 rad C^-Cg-alkyl, C3-C4-alkenyl, 2-propinyl, 3-halogen-2-pro-pinyl, fenyl, med halogen, Ci-C3~alkyl, Ci-C3-alkoxi, nitro och/eller CF3 en eller flera ganger substituerad fenyl, ben-syl, eller med halogen, Ci~C3-alkyl och/eller Ci~C3-alkoxi en eller £lera ganger substituerad bensyl; R3, R4 och R5 betecknar oberoende av varandra väte eller C^-C4-alkyl, varvid totalantalet kolatomer i resterna R3, R4 och R5 inte överstiger talet 6 och Rg betecknar väte eller Ci-C3-alkyl? samt syraadditionssalter och metallkomplex av dessa forening-ar.
2. Förening enligt patentkravet 1, känneteck-n a d därav, att den är 2-[p-(fenoxi)-fenyl]-2-[l-(lH-l,2,4-triazolyl)-metyl]-4-etyl-l,3-dioxan eller ett salt därav.
3. Förening enligt patentkravet 1, känneteck-n a d därav, att den är 2-[p-(fenoxi)-fenyl]-2-[l-(lH-l,2,4-triazolyl)-metyl]-4-metyl-l,3-dioxolan eller ett salt därav.
4. Förening enligt patentkravet 1, känneteck-n a d därav, att den är 2-[p-(fenoxi)-fenyl]—2—[1—(1H-1,2,4-triazolyl)-metyl]-4-etyl-l,3-dioxolan eller ett salt därav.
5. Förening enligt patentkravet 1, känneteck-n a d därav, att den är 2-[4-(p-klorfenoxi)-2-klorfenyl]- 2 — [1—(1H-1,2,4-triazolyl)-metyl]-4-etyl-l,3-dioxolan eller ett salt därav.
6. Förfarande för framställning av föreningar med for-meln I „. „ ί X i vilken Y betecknar gruppen -CH= eller -N=, Ra och Rjj betecknar oberoende av varandra väte, halogen, r <-l_C3-alkoxi eller nitro? 123 77458 Ar betecknar osubstituerad eller med halogen, Ci-Cy-alkyl, Cl'Cy-alkoxi, nitro och/eller CF3 en eller flera ganger subs-tituerad fenyl; U och V betecknar oberoende av varandra eventuellt med halogen eller Ci-Cg-alkoxi substituerad Cx-Cx2~allcyl eller de bildar tillsammans en av de följande alkylenbryggorna \ /’ v- ' ' · \ +-*s eller \« > . varvid • — * ^ \ och R2 betecknar oberoende av varandra väte, Ci-C^-3!^! * en eller flera ganger med halogen substituerad Ci-C^-alkyl · fenyl, en eller flera ganger med halogen och/eller C1-C3-alkyl substituerad fenyl eller gruppen -CH2-Z-R7, varvid Z betecknar syre eller svavel och R7 betecknar väte, C^-Cg-alkyl, med Ci-C2~alkoxi substituerad Ci-Cg-alkyl, C3-C4~alkenyl, 2-propinyl, 3-halogen-2-pro-pinyl, fenyl, med halogen, Ci-C3-alkyl, C^-C3-alkoxi, nitro och/eller CF3 en eller flera ginger substituerad fenyl, ben-syl, eller med halogen, Ci-Cg-alkyl och/eller Ci-C3~alkoxi en eller flera ginger substituerad bensyl; R3, R4 och R5 betecknar oberoende av varandra väte eller C1-C4-alkyl, varvid totalantalet kolatomer i resterna R3, R4 och R5 inte överstiger talet 6 och Rg betecknar väte eller Ci-C3-alkyl; samt syraadditionssalter och metallkomplex av dessa förening-ar, kännetecknat därav, att A) en förening med formeln II Me-l/ I τ«· i vilken Me betecknar väte eller en metallkatjon, kondense-ras med en förening med formeln III 124 7 7 4 5 8 R /ί?Ν ΑΓ'°'·\ . /-7°\—ch2"x t «Ο (ΙΙΙ)· i vilken X betecknar en nukleofug avlägsnande grupp? eller B) i en förening med formeln IV R ]a ~* + \ -·Ν Ar'°'\ , >'J-CH2'\ <IV) s omvandlas karbonylgruppen till en grupp med formeln v V y (v) u-----V eller C) för framställning av föreningar med formeln I, i vilka U och V betecknar tillsammans en grupp med formeln -CH2-CH(CH2ZR7')- och Rj1 betecknar en fr£n väte avvikande rest R-j, föreningarna med formlerna VI och VII R Ar‘°'<»» °°h χ2-*7 ('id. loo \ -X 11 vilka en av resterna och X2 betecknar eventuellt i en saltform varande hydroxi eller merkapto, t.ex. en med formeln -Z-Me, och den andra betecknar en nukleofil avlägsnande grupp X, eller bide Χχ och X2 betecknar hydroxigrupper, kon-denseras med varandra, eller D) föreningarna med formlerna Vili och IX 125 77458 R Ar-X3 (VIII) och x4-/ )--(IX), 't· 07 \ N~ \ 1 1 i vilka en av resterna X3 och X4 betecknar en grupp -Ο-Me, i vilken Me är väte eller heist en metallkatjon, och den andra betecknar en rest som kan omvandlas till aryloxi, kondense-ras med varandra, eller E) en förening med formeln R 4· Ar-e-c-o-·^ .«ς [ (X) ο ·|· / \ *v 1 1 b U-----V dekarboxyleras intramolekylärt och, om si önskas, en enligt förfarandet erhlllen förening överförs i en annan förening med formeln I och/eller en enligt förfarandet erhlllen förening i ett syraadditionssalt, ett enligt förfarandet erhal-let syraadditionssalt i en fri förening eller ett annat syraadditionssalt, eller en enligt förfarandet erhlllen fri förening eller resp. ett enligt förfarandet erhlllet syraadditionssalt i ett metal1kömpiex, varvid substituenterna i formlerna II-X betecknar detsamma som vid formeln I, Z betecknar syre eller svavel och Me väte eller en metallkatjon.
7. Förfarande för bekämpning eller förhindring av smit-ta, som förorsakats av fytopatogena mikroorganismer i kul-turväxter, kännetecknat därav, att man sprider en förening med formeln I enligt patentkravet 1 pl en växt eller pä dess växtplats.
8. Användning av föreningar med formeln I enligt patentkravet 1 för bekämpning och/eller förebyggande av smitta förorsakats av mikroorganismer i växter.
9. Användning enligt patentkravet 8, känneteck-n a d därav, att mikroorganismerna är fytopatogena svampar.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306681 | 1981-05-12 | ||
| CH306681 | 1981-05-12 | ||
| CH242882 | 1982-04-21 | ||
| CH242882 | 1982-04-21 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI821572A0 FI821572A0 (fi) | 1982-05-05 |
| FI821572L FI821572L (fi) | 1982-11-13 |
| FI77458B true FI77458B (fi) | 1988-11-30 |
| FI77458C FI77458C (sv) | 1989-03-10 |
Family
ID=25690423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821572A FI77458C (sv) | 1981-05-12 | 1982-05-05 | Nya mikrobicida arylfenyleterderivat, förfarande för deras framställni ng och deras användning. |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0065485B1 (sv) |
| KR (1) | KR870001021B1 (sv) |
| AR (4) | AR241224A1 (sv) |
| AU (1) | AU562239B2 (sv) |
| BG (1) | BG60715B2 (sv) |
| CA (1) | CA1192203A (sv) |
| CS (1) | CS241507B2 (sv) |
| DD (2) | DD207143A5 (sv) |
| DE (1) | DE3280151D1 (sv) |
| DK (1) | DK157866C (sv) |
| ES (5) | ES8307797A1 (sv) |
| FI (1) | FI77458C (sv) |
| GB (1) | GB2098607B (sv) |
| GR (1) | GR76419B (sv) |
| HU (1) | HU189136B (sv) |
| IE (1) | IE53225B1 (sv) |
| IL (1) | IL65728A (sv) |
| MA (1) | MA19470A1 (sv) |
| NO (1) | NO160580C (sv) |
| NZ (1) | NZ200581A (sv) |
| OA (1) | OA07097A (sv) |
| PH (1) | PH21917A (sv) |
| PL (5) | PL138798B1 (sv) |
| PT (1) | PT74872A (sv) |
| SU (2) | SU1178309A3 (sv) |
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| DE3144318A1 (de) * | 1981-11-07 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | 2-imidazolylmethyl-2-phenyl-1, 3-dioxolane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| FI834141A7 (fi) * | 1982-11-16 | 1984-05-17 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya arylfenyleterderivat. |
| FI842502A7 (fi) * | 1983-06-27 | 1984-12-28 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya 2-substituerade bensofuran derivat. |
| 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 |
| US4870094A (en) * | 1984-05-02 | 1989-09-26 | Uniroyal Chemical Company, Inc. | Substituted imidazoles and triazoles |
| US5039332A (en) * | 1985-09-19 | 1991-08-13 | Uniroyal Chemical Company, Inc. | Substituted oxathiolanes |
| IT1186784B (it) * | 1985-11-04 | 1987-12-16 | Montedison Spa | Azoliderivati ad attivita' antufungina |
| MY100575A (en) * | 1985-11-22 | 1990-12-15 | Ciba Geigy Ag | Microbicides |
| EP0296518A1 (de) * | 1987-06-22 | 1988-12-28 | Ciba-Geigy Ag | Neue Phenylether-derivate als Mikrobizide, Verfahren zu deren Herstellung und deren Verwendung |
| EP0354182B1 (de) * | 1988-08-04 | 1993-01-20 | Ciba-Geigy Ag | Mikrobizide Mittel |
| US5250559A (en) * | 1988-11-18 | 1993-10-05 | Ciba-Geigy Corporation | Microbicidal compositions |
| EP0443980A1 (de) * | 1990-01-25 | 1991-08-28 | Ciba-Geigy Ag | Mikrobizide |
| EP0488945B1 (de) * | 1990-11-20 | 1996-03-13 | Ciba-Geigy Ag | Fungizide Mittel |
| ES2086716T3 (es) * | 1991-12-19 | 1996-07-01 | Ciba Geigy Ag | Microbicidas. |
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| US5741818A (en) * | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4101666A (en) * | 1975-10-06 | 1978-07-18 | Janssen Pharmaceutica N.V. | 1-(2-Ar-4-R-1,3-dioxolan-2-ylmethyl)imidazoles |
| US3936470A (en) * | 1975-01-27 | 1976-02-03 | Janssen Pharmaceutica N.V. | 1,3-Dioxolan-2-ylmethylimidazoles |
| US4160838A (en) * | 1977-06-02 | 1979-07-10 | Janssen Pharmaceutica N.V. | Antimicrobial and plant-growth-regulating triazole derivatives |
| IL61011A (en) * | 1979-09-12 | 1985-07-31 | Janssen Pharmaceutica Nv | Dioxolanyl-and dioxanyl-methazolium derivatives,their preparation and fungicidal compositions comprising them |
| CA1173449A (en) * | 1979-11-16 | 1984-08-28 | Adolf Hubele | 1-¬2-(4-diphenyl)ethyl|-1h-azolylketals |
| DE3018865A1 (de) * | 1980-05-16 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Antimikrobielle mittel |
| US4321272A (en) * | 1980-08-25 | 1982-03-23 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkylimidazoles |
| DE3144318A1 (de) * | 1981-11-07 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | 2-imidazolylmethyl-2-phenyl-1, 3-dioxolane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1982
- 1982-05-05 FI FI821572A patent/FI77458C/sv not_active IP Right Cessation
- 1982-05-06 DE DE8282810193T patent/DE3280151D1/de not_active Expired - Lifetime
- 1982-05-06 EP EP82810193A patent/EP0065485B1/de not_active Expired - Lifetime
- 1982-05-07 GB GB8213324A patent/GB2098607B/en not_active Expired
- 1982-05-10 CA CA000402589A patent/CA1192203A/en not_active Expired
- 1982-05-10 AR AR82289356A patent/AR241224A1/es active
- 1982-05-10 GR GR68119A patent/GR76419B/el unknown
- 1982-05-10 IL IL65728A patent/IL65728A/xx not_active IP Right Cessation
- 1982-05-10 MA MA19676A patent/MA19470A1/fr unknown
- 1982-05-11 PL PL1982243094A patent/PL138798B1/pl unknown
- 1982-05-11 PL PL1982236376A patent/PL138255B1/pl unknown
- 1982-05-11 NO NO821560A patent/NO160580C/no not_active IP Right Cessation
- 1982-05-11 AU AU83584/82A patent/AU562239B2/en not_active Expired
- 1982-05-11 SU SU823441700A patent/SU1178309A3/ru active
- 1982-05-11 HU HU821471A patent/HU189136B/hu unknown
- 1982-05-11 PL PL1982243095A patent/PL139118B1/pl unknown
- 1982-05-11 DK DK211582A patent/DK157866C/da not_active IP Right Cessation
- 1982-05-11 OA OA57684A patent/OA07097A/xx unknown
- 1982-05-11 PT PT74872A patent/PT74872A/pt unknown
- 1982-05-11 BG BG056607A patent/BG60715B2/xx unknown
- 1982-05-11 IE IE1128/82A patent/IE53225B1/en not_active IP Right Cessation
- 1982-05-11 ES ES512067A patent/ES8307797A1/es not_active Expired
- 1982-05-11 PL PL1982243096A patent/PL138797B1/pl unknown
- 1982-05-11 NZ NZ200581A patent/NZ200581A/en unknown
- 1982-05-11 PL PL1982243097A patent/PL139117B1/pl unknown
- 1982-05-12 PH PH27284A patent/PH21917A/en unknown
- 1982-05-12 CS CS823455A patent/CS241507B2/cs unknown
- 1982-05-12 DD DD82239803A patent/DD207143A5/de not_active IP Right Cessation
- 1982-05-12 DD DD255958A patent/DD212039A1/xx not_active IP Right Cessation
- 1982-05-12 KR KR8202108A patent/KR870001021B1/ko not_active Expired
- 1982-12-27 SU SU823529008A patent/SU1436855A3/ru active
-
1983
- 1983-04-15 ES ES521527A patent/ES521527A0/es active Granted
- 1983-04-15 ES ES521526A patent/ES521526A0/es active Granted
- 1983-04-15 ES ES521525A patent/ES8500936A1/es not_active Expired
- 1983-04-15 ES ES521528A patent/ES521528A0/es active Granted
- 1983-09-27 AR AR83294338A patent/AR244222A1/es active
- 1983-09-27 AR AR83294335A patent/AR241704A1/es active
- 1983-09-27 AR AR83294336A patent/AR241907A1/es active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: NOVARTIS AG |
|
| MA | Patent expired |
Owner name: NOVARTIS AG |