GB1589852A - 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles - Google Patents
1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles Download PDFInfo
- Publication number
- GB1589852A GB1589852A GB31630/77A GB3163077A GB1589852A GB 1589852 A GB1589852 A GB 1589852A GB 31630/77 A GB31630/77 A GB 31630/77A GB 3163077 A GB3163077 A GB 3163077A GB 1589852 A GB1589852 A GB 1589852A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triazole
- acid addition
- dichlorophenyl
- physiologically acceptable
- acceptable acid
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 34
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000004480 active ingredient Substances 0.000 claims abstract description 12
- NSPMIYGKQJPBQR-CVMUNTFWSA-N 1h-1,2,4-triazole Chemical class [13CH]=1[15N]=[13CH][15NH][15N]=1 NSPMIYGKQJPBQR-CVMUNTFWSA-N 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 lower alkyloxyphenyl Chemical group 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 9
- 230000000843 anti-fungal effect Effects 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 230000002538 fungal effect Effects 0.000 claims description 9
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 6
- XRTGEXMHEJYFCR-UHFFFAOYSA-N 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C(C1CCCCC1)CN1N=CN=C1 XRTGEXMHEJYFCR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 5
- 239000005648 plant growth regulator Substances 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- QTYNSYDZEQPZQG-UHFFFAOYSA-N 1-[2-(2,4-dibromophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Br)C=C(Br)C=1C(CCCC)CN1C=NC=N1 QTYNSYDZEQPZQG-UHFFFAOYSA-N 0.000 claims description 3
- OKFNDRAXJVLCSI-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-methylbutyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(C)C)CN1C=NC=N1 OKFNDRAXJVLCSI-UHFFFAOYSA-N 0.000 claims description 3
- SXMLWBVZPDZWTG-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(C)CC)CN1C=NC=N1 SXMLWBVZPDZWTG-UHFFFAOYSA-N 0.000 claims description 3
- NEDKLHZEQYTKIX-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)hexyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCCC)CN1C=NC=N1 NEDKLHZEQYTKIX-UHFFFAOYSA-N 0.000 claims description 3
- RXUKNHVFFYHSRK-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(F)=CC=C1C(CN1N=CN=C1)CCC1=CC=C(Cl)C=C1 RXUKNHVFFYHSRK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 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 claims description 3
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- PINPXQLXNURYOJ-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-4-methylpentyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CC(C)C)CN1C=NC=N1 PINPXQLXNURYOJ-UHFFFAOYSA-N 0.000 claims description 2
- GIDULHOTKAIVFM-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4-(4-methylphenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1CCC(C=1C=CC(F)=CC=1)CN1N=CN=C1 GIDULHOTKAIVFM-UHFFFAOYSA-N 0.000 claims description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 2
- FMGOPNNYXMJSQP-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)hexyl methanesulfonate Chemical compound CCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl FMGOPNNYXMJSQP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- PEASYXLOQMURPR-UHFFFAOYSA-N [4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl] methanesulfonate Chemical compound C=1C=C(F)C=CC=1C(COS(=O)(=O)C)CCC1=CC=C(Cl)C=C1 PEASYXLOQMURPR-UHFFFAOYSA-N 0.000 claims description 2
- UXIRDULGNFNBLX-UHFFFAOYSA-N [4-(4-chlorophenyl)-2-(4-methylphenyl)butyl] methanesulfonate Chemical compound C1=CC(C)=CC=C1C(COS(C)(=O)=O)CCC1=CC=C(Cl)C=C1 UXIRDULGNFNBLX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 4
- BIFSIDIOXLCEQE-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-methylphenyl)butyl]-1,2,4-triazole Chemical compound C1=CC(C)=CC=C1C(CN1N=CN=C1)CCC1=CC=C(Cl)C=C1 BIFSIDIOXLCEQE-UHFFFAOYSA-N 0.000 claims 2
- CIZMWWFUVMGBEL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)heptyl methanesulfonate Chemical compound CCCCCC(COS(C)(=O)=O)C1=CC=C(Cl)C=C1Cl CIZMWWFUVMGBEL-UHFFFAOYSA-N 0.000 claims 1
- GOWRHDOMJQAPCM-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-methylpentane-1-sulfonic acid Chemical compound CC(C)C(CCS(=O)(=O)O)C1=C(C=C(C=C1)Cl)Cl GOWRHDOMJQAPCM-UHFFFAOYSA-N 0.000 claims 1
- HTWYQTSMFXYLKB-UHFFFAOYSA-N [2-(2,4-dichlorophenyl)-3-methylpentyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(C(C)CC)C1=CC=C(Cl)C=C1Cl HTWYQTSMFXYLKB-UHFFFAOYSA-N 0.000 claims 1
- DPHPEEKNASPCHI-UHFFFAOYSA-N [2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl] methanesulfonate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COS(=O)(=O)C)C1CCCCC1 DPHPEEKNASPCHI-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- URIRDRHUUFRHAS-UHFFFAOYSA-N hexyl methanesulfonate Chemical compound CCCCCCOS(C)(=O)=O URIRDRHUUFRHAS-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 17
- 150000002148 esters Chemical class 0.000 abstract description 14
- 230000000855 fungicidal effect Effects 0.000 abstract description 6
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 31
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 17
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000002140 halogenating effect Effects 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- UPZGJLYTRBYTLM-UHFFFAOYSA-M lithium;iodide;dihydrate Chemical compound [Li+].O.O.[I-] UPZGJLYTRBYTLM-UHFFFAOYSA-M 0.000 description 1
- YZPNYLPAGHAAPJ-UHFFFAOYSA-N methyl 2-(2,4-dibromophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1Br YZPNYLPAGHAAPJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 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
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols 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
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940024986 topical antifungal imidazole and triazole derivative Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
-
- 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71330876A | 1976-08-10 | 1976-08-10 | |
| US79163277A | 1977-04-27 | 1977-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1589852A true GB1589852A (en) | 1981-05-20 |
Family
ID=27108969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31630/77A Expired GB1589852A (en) | 1976-08-10 | 1977-07-27 | 1-(2-aryl-2-r-ethyl)-1h-1,2,4-triazoles |
Country Status (25)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0096658A1 (de) * | 1982-06-08 | 1983-12-21 | Ciba-Geigy Ag | Mittel zur Bekämpfung von Pflanzenkrankheiten, dessen Herstellung und dessen Verwendung im Pflanzenschutz |
| EP0234242A3 (en) * | 1986-01-23 | 1988-06-15 | Montedison S.P.A. | Fungicidal azolyl-derivatives |
| EP0354689A1 (en) * | 1988-08-04 | 1990-02-14 | Imperial Chemical Industries Plc | Diphenylethane derivatives |
| US4999364A (en) * | 1988-08-08 | 1991-03-12 | Imperial Chemical Industries Plc | Azole derivatives |
Families Citing this family (20)
| 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 |
| NZ196075A (en) * | 1980-02-04 | 1982-12-07 | Janssen Pharmaceutica Nv | Agent to protect wood coatings and detergents from micro-organisms using a triazole |
| DE3267642D1 (en) * | 1981-03-10 | 1986-01-09 | Ciba Geigy Ag | Process for the preparation of phenylethyl triazoles |
| DE3362000D1 (en) * | 1982-06-18 | 1986-03-13 | Ciba Geigy Ag | Method for the production of 1-(2-(,4-dichlorphenyl)pentyl)-1h-1,2,4-triazole and hydrazone- or hydrazine-derivatives |
| EP0121081B1 (de) * | 1983-03-03 | 1991-01-30 | BASF Aktiengesellschaft | Azolylmethylcycloalkane, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE3310830A1 (de) * | 1983-03-24 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Substituierte phenethyl-triazolyl-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| EP0126430B1 (de) * | 1983-05-19 | 1991-08-28 | Ciba-Geigy Ag | Verfahren zur Herstellung von 1-Triazolylethylether-Derivaten, sowie mikrobizide Mittel enthaltende neue 1-triazolyl-phenoxyphenylethylether-derivate als Wirkstoffe und deren Verwendung |
| GB8405368D0 (en) * | 1984-03-01 | 1984-04-04 | Ici Plc | Heterocyclic compounds |
| JPH03125676A (ja) * | 1989-10-12 | 1991-05-29 | Deele Raumu:Kk | 自動車 |
| DE19829113A1 (de) | 1998-06-10 | 1999-12-16 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| EP2255650A3 (de) | 2005-06-09 | 2011-04-27 | Bayer CropScience AG | Wirkstoffkombinationen |
| DE102005035300A1 (de) | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| EP2000028A1 (de) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| BR112012001080A2 (pt) | 2009-07-16 | 2015-09-01 | Bayer Cropscience Ag | Combinações de substâncias ativas sinérgicas contendo feniltriazóis |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU557755A3 (ru) * | 1968-08-19 | 1977-05-05 | Янссен Фармасьютика Н.В. (Фирма) | Способ получени производных имидазола |
| US3647814A (en) * | 1969-07-03 | 1972-03-07 | Rohm & Haas | Method for preparing 4-substituted-1 2 4-triazoles |
| US3658813A (en) * | 1970-01-13 | 1972-04-25 | Janssen Pharmaceutica Nv | 1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles |
| DE2009020C3 (de) * | 1970-02-26 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen |
| US3821394A (en) * | 1970-07-29 | 1974-06-28 | H Timmler | Antimycotic composition and method employing a substituted benzyl-azoles |
| US3927017A (en) * | 1974-06-27 | 1975-12-16 | Janssen Pharmaceutica Nv | 1-({62 -Aryl-{62 -R-ethyl)imidazoles |
| DE2431407C2 (de) * | 1974-06-29 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | 1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
-
1977
- 1977-07-26 AU AU27326/77A patent/AU515134B2/en not_active Expired
- 1977-07-27 GB GB31630/77A patent/GB1589852A/en not_active Expired
- 1977-07-27 CY CY1204A patent/CY1204A/xx unknown
- 1977-07-29 CA CA283,776A patent/CA1133492A/en not_active Expired
- 1977-07-29 FR FR7723528A patent/FR2361375A1/fr active Granted
- 1977-08-03 NZ NZ184835A patent/NZ184835A/xx unknown
- 1977-08-08 IT IT50599/77A patent/IT1080109B/it active
- 1977-08-08 PT PT66902A patent/PT66902B/pt unknown
- 1977-08-09 BR BR7705266A patent/BR7705266A/pt unknown
- 1977-08-09 AT AT581377A patent/AT361918B/de not_active IP Right Cessation
- 1977-08-09 DK DK355477A patent/DK159551C/da not_active IP Right Cessation
- 1977-08-09 NL NLAANVRAGE7708764,A patent/NL181431C/xx not_active IP Right Cessation
- 1977-08-09 DE DE19772735872 patent/DE2735872A1/de active Granted
- 1977-08-09 IE IE1664/77A patent/IE45462B1/en not_active IP Right Cessation
- 1977-08-09 IL IL52692A patent/IL52692A/xx unknown
- 1977-08-09 AR AR268726A patent/AR222142A1/es active
- 1977-08-09 SE SE7709016A patent/SE437267B/xx not_active IP Right Cessation
- 1977-08-10 JP JP9521177A patent/JPS5321168A/ja active Granted
- 1977-08-10 GR GR54132A patent/GR58202B/el unknown
- 1977-08-10 ES ES461526A patent/ES461526A1/es not_active Expired
- 1977-08-10 CH CH982877A patent/CH630231A5/de not_active IP Right Cessation
-
1983
- 1983-06-17 SG SG346/83A patent/SG34683G/en unknown
- 1983-06-23 KE KE3299A patent/KE3299A/xx unknown
- 1983-11-24 HK HK606/83A patent/HK60683A/en not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY32/85A patent/MY8500032A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0096658A1 (de) * | 1982-06-08 | 1983-12-21 | Ciba-Geigy Ag | Mittel zur Bekämpfung von Pflanzenkrankheiten, dessen Herstellung und dessen Verwendung im Pflanzenschutz |
| EP0234242A3 (en) * | 1986-01-23 | 1988-06-15 | Montedison S.P.A. | Fungicidal azolyl-derivatives |
| EP0354689A1 (en) * | 1988-08-04 | 1990-02-14 | Imperial Chemical Industries Plc | Diphenylethane derivatives |
| US4999364A (en) * | 1988-08-08 | 1991-03-12 | Imperial Chemical Industries Plc | Azole derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19970726 |