HU193166B - Process for preparing alpha-/1-triazolyl/-keto-derivatives - Google Patents
Process for preparing alpha-/1-triazolyl/-keto-derivatives Download PDFInfo
- Publication number
- HU193166B HU193166B HU832008A HU200883A HU193166B HU 193166 B HU193166 B HU 193166B HU 832008 A HU832008 A HU 832008A HU 200883 A HU200883 A HU 200883A HU 193166 B HU193166 B HU 193166B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- chlorophenyl
- carbonyl
- solid
- compounds
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 239000012442 inert solvent Substances 0.000 claims abstract description 7
- 150000007530 organic bases Chemical class 0.000 claims abstract description 7
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- 238000010992 reflux Methods 0.000 claims abstract description 6
- -1 1-triazolyl Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000468 ketone group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 150000003512 tertiary amines Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 44
- 230000000855 fungicidal effect Effects 0.000 abstract description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 19
- 239000003208 petroleum Substances 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- XVVGBFGMWMOBLB-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-oxoacetaldehyde Chemical compound ClC1=CC=C(C(=O)C=O)C=C1 XVVGBFGMWMOBLB-UHFFFAOYSA-N 0.000 description 1
- DIMRGVFIRSHSEE-UHFFFAOYSA-N 2-benzoylbutanoic acid Chemical compound CCC(C(O)=O)C(=O)C1=CC=CC=C1 DIMRGVFIRSHSEE-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- BIOFRTXSGXLHQZ-UHFFFAOYSA-N CCC(=C(C(=O)C1=CC=CC=C1)C(=O)O)C(=O)C2=CC=C(C=C2)Cl Chemical compound CCC(=C(C(=O)C1=CC=CC=C1)C(=O)O)C(=O)C2=CC=C(C=C2)Cl BIOFRTXSGXLHQZ-UHFFFAOYSA-N 0.000 description 1
- 241000582541 Cetraspora helvetica Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 235000021013 raspberries Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21665/82A IT1157947B (it) | 1982-06-03 | 1982-06-03 | Alfa-(1-trazolil)-cheto-derivati fungicidi |
| IT25048/82A IT1155094B (it) | 1982-12-30 | 1982-12-30 | Alfa -(1-triazolil)-cheto-derivati fungicidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU193166B true HU193166B (en) | 1987-08-28 |
Family
ID=26327960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832008A HU193166B (en) | 1982-06-03 | 1983-06-03 | Process for preparing alpha-/1-triazolyl/-keto-derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4894384A (enExample) |
| KR (1) | KR900005678B1 (enExample) |
| AT (1) | AT383348B (enExample) |
| AU (1) | AU565221B2 (enExample) |
| BR (1) | BR8302921A (enExample) |
| CA (1) | CA1203807A (enExample) |
| CH (1) | CH659249A5 (enExample) |
| DE (1) | DE3319990A1 (enExample) |
| ES (1) | ES8407481A1 (enExample) |
| FR (1) | FR2528045B1 (enExample) |
| GB (1) | GB2121042B (enExample) |
| GR (1) | GR79206B (enExample) |
| HU (1) | HU193166B (enExample) |
| IL (1) | IL68894A (enExample) |
| MX (1) | MX7123E (enExample) |
| NL (1) | NL8301961A (enExample) |
| NZ (1) | NZ204441A (enExample) |
| OA (1) | OA07451A (enExample) |
| PT (1) | PT76792B (enExample) |
| SE (1) | SE454443B (enExample) |
| SU (2) | SU1209028A3 (enExample) |
| TR (1) | TR23880A (enExample) |
| YU (1) | YU43180B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1170080B (it) * | 1983-12-30 | 1987-06-03 | Montedison Spa | Triazolil-cheto-derivati aventi attivita' fungicida |
| IT1176008B (it) * | 1984-04-11 | 1987-08-12 | Montedison Spa | Triazolilcheto derivati fungicidi |
| US5429570A (en) * | 1993-12-23 | 1995-07-04 | Beyer; Eric L. | Free weight exercise device |
| JP4463766B2 (ja) * | 2003-09-25 | 2010-05-19 | パナソニック株式会社 | 圧電素子及びそれを備えたインクジェットヘッド並びにそれらの製造方法 |
| GB0919194D0 (en) | 2009-11-02 | 2009-12-16 | Lytix Biopharma As | Compounds |
| JP7079494B2 (ja) | 2016-04-01 | 2022-06-02 | 国立大学法人 東京大学 | 新規化合物とその合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4130409A (en) * | 1976-06-08 | 1978-12-19 | Imperial Chemical Industries Limited | Triazolyl butandiones |
| GB1553907A (en) * | 1976-07-29 | 1979-10-10 | Ici Ltd | Substituted ketones and their use as fungicidal compounds |
| GB1554490A (en) * | 1977-12-05 | 1979-10-24 | Ici Ltd | Method of regulating plant growth using triazole and imidazole compounds and some of the compounds themselves |
| US4181518A (en) * | 1976-12-24 | 1980-01-01 | Imperial Chemical Industries Limited | Method of regulating plant growth using triazole and imidazole compounds |
| DE2831235A1 (de) * | 1978-07-15 | 1980-01-31 | Basf Ag | Neue azolyl- beta -dicarbonyl-verbindungen |
| DE2836945A1 (de) * | 1978-08-24 | 1980-03-13 | Hoechst Ag | Derivate des 1,2,4-triazols |
| DE3032326A1 (de) * | 1980-08-27 | 1982-04-08 | Bayer Ag, 5090 Leverkusen | Azolylalkyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| AR228764A1 (es) * | 1980-12-20 | 1983-04-15 | Bayer Ag | 1-azolil-3,3-dimetilalcan(c3-4)-2-onas y-2-oles,sustituidos,procedimiento para su produccion y composiciones protectoras de plantas fungicidas y reguladoras del crecimiento de las plantas a base de dichos compuestos |
| DE3104311A1 (de) * | 1981-02-07 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | 2-azolylmethyl-1,3-dioxolan- und -dioxan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
-
1983
- 1983-05-31 GR GR71513A patent/GR79206B/el unknown
- 1983-05-31 AU AU15242/83A patent/AU565221B2/en not_active Ceased
- 1983-06-01 ES ES522885A patent/ES8407481A1/es not_active Expired
- 1983-06-01 FR FR8309054A patent/FR2528045B1/fr not_active Expired
- 1983-06-01 DE DE3319990A patent/DE3319990A1/de not_active Ceased
- 1983-06-01 PT PT76792A patent/PT76792B/pt unknown
- 1983-06-01 NZ NZ204441A patent/NZ204441A/en unknown
- 1983-06-01 CH CH2995/83A patent/CH659249A5/fr not_active IP Right Cessation
- 1983-06-01 BR BR8302921A patent/BR8302921A/pt not_active IP Right Cessation
- 1983-06-02 TR TR83/3722A patent/TR23880A/xx unknown
- 1983-06-02 SU SU833605553A patent/SU1209028A3/ru active
- 1983-06-02 MX MX8310640U patent/MX7123E/es unknown
- 1983-06-02 NL NL8301961A patent/NL8301961A/nl not_active Application Discontinuation
- 1983-06-02 SE SE8303117A patent/SE454443B/sv not_active IP Right Cessation
- 1983-06-02 CA CA000429591A patent/CA1203807A/en not_active Expired
- 1983-06-02 YU YU1229/83A patent/YU43180B/xx unknown
- 1983-06-03 OA OA58017A patent/OA07451A/xx unknown
- 1983-06-03 AT AT0204683A patent/AT383348B/de not_active IP Right Cessation
- 1983-06-03 KR KR1019830002486A patent/KR900005678B1/ko not_active Expired
- 1983-06-03 GB GB08315303A patent/GB2121042B/en not_active Expired
- 1983-06-03 HU HU832008A patent/HU193166B/hu unknown
- 1983-06-06 IL IL68894A patent/IL68894A/xx unknown
-
1984
- 1984-01-27 SU SU843701272A patent/SU1410860A3/ru active
-
1988
- 1988-02-29 US US07/165,382 patent/US4894384A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TR23880A (tr) | 1990-10-16 |
| GR79206B (enExample) | 1984-10-22 |
| SU1209028A3 (ru) | 1986-01-30 |
| PT76792A (en) | 1983-07-01 |
| IL68894A0 (en) | 1983-10-31 |
| FR2528045B1 (fr) | 1988-09-02 |
| AU1524283A (en) | 1983-12-08 |
| ES522885A0 (es) | 1984-10-01 |
| YU122983A (en) | 1985-12-31 |
| SU1410860A3 (ru) | 1988-07-15 |
| OA07451A (fr) | 1984-12-31 |
| AT383348B (de) | 1987-06-25 |
| FR2528045A1 (fr) | 1983-12-09 |
| BR8302921A (pt) | 1984-02-07 |
| IL68894A (en) | 1987-02-27 |
| US4894384A (en) | 1990-01-16 |
| ES8407481A1 (es) | 1984-10-01 |
| CA1203807A (en) | 1986-04-29 |
| DE3319990A1 (de) | 1983-12-08 |
| NL8301961A (nl) | 1984-01-02 |
| MX7123E (es) | 1987-06-29 |
| GB2121042B (en) | 1986-02-19 |
| KR900005678B1 (ko) | 1990-08-06 |
| GB8315303D0 (en) | 1983-07-06 |
| SE8303117D0 (sv) | 1983-06-02 |
| AU565221B2 (en) | 1987-09-10 |
| NZ204441A (en) | 1985-09-13 |
| GB2121042A (en) | 1983-12-14 |
| YU43180B (en) | 1989-04-30 |
| ATA204683A (de) | 1986-11-15 |
| SE8303117L (sv) | 1983-12-04 |
| CH659249A5 (fr) | 1987-01-15 |
| KR840005112A (ko) | 1984-11-03 |
| PT76792B (en) | 1986-02-27 |
| SE454443B (sv) | 1988-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |