NL8301961A - Alfa-(1-triazolyl)-ketoderivaten met fungicide werking. - Google Patents
Alfa-(1-triazolyl)-ketoderivaten met fungicide werking. Download PDFInfo
- Publication number
- NL8301961A NL8301961A NL8301961A NL8301961A NL8301961A NL 8301961 A NL8301961 A NL 8301961A NL 8301961 A NL8301961 A NL 8301961A NL 8301961 A NL8301961 A NL 8301961A NL 8301961 A NL8301961 A NL 8301961A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- alkyl
- carbon atoms
- optionally substituted
- groups
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 15
- -1 1-TRIAZOLYL Chemical class 0.000 title claims description 7
- 230000000694 effects Effects 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 208000031888 Mycoses Diseases 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 206010017533 Fungal infection Diseases 0.000 claims description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 244000045561 useful plants Species 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 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
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 230000001143 conditioned effect Effects 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000003898 horticulture Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 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
- 239000013543 active substance Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 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
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241001000287 Helvetia Species 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- MOMWFXLCFJOAFX-UHFFFAOYSA-N OOOOOOOO Chemical compound OOOOOOOO MOMWFXLCFJOAFX-UHFFFAOYSA-N 0.000 description 1
- IVDBGHPEQSTHRK-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOOOOO IVDBGHPEQSTHRK-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 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
- 241000233626 Plasmopara Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- OVCZHIUAIOJCAF-UHFFFAOYSA-N ethyl 2-benzoyl-4-(4-chlorophenyl)-4-oxobut-2-enoate Chemical compound C=1C=CC=CC=1C(=O)C(C(=O)OCC)=CC(=O)C1=CC=C(Cl)C=C1 OVCZHIUAIOJCAF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 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
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21665/82A IT1157947B (it) | 1982-06-03 | 1982-06-03 | Alfa-(1-trazolil)-cheto-derivati fungicidi |
| IT2166582 | 1982-06-03 | ||
| IT2504882 | 1982-12-30 | ||
| IT25048/82A IT1155094B (it) | 1982-12-30 | 1982-12-30 | Alfa -(1-triazolil)-cheto-derivati fungicidi |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8301961A true NL8301961A (nl) | 1984-01-02 |
Family
ID=26327960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8301961A NL8301961A (nl) | 1982-06-03 | 1983-06-02 | Alfa-(1-triazolyl)-ketoderivaten met fungicide werking. |
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 |
| 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 |
| HU193166B (en) | 1987-08-28 |
| 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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| BT | A notification was added to the application dossier and made available to the public | ||
| A85 | Still pending on 85-01-01 | ||
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| BB | A search report has been drawn up | ||
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