HU187270B - Plant growth regulating and fungicide compositions containing 1-vinyil-triazole derivatives as active substances further process for preparing the active substances - Google Patents
Plant growth regulating and fungicide compositions containing 1-vinyil-triazole derivatives as active substances further process for preparing the active substances Download PDFInfo
- Publication number
- HU187270B HU187270B HU80348A HU34880A HU187270B HU 187270 B HU187270 B HU 187270B HU 80348 A HU80348 A HU 80348A HU 34880 A HU34880 A HU 34880A HU 187270 B HU187270 B HU 187270B
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- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- cyclohexyl
- compounds
- growth
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 56
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- 230000008635 plant growth Effects 0.000 title description 5
- 230000001105 regulatory effect Effects 0.000 title description 5
- 239000000417 fungicide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000013543 active substance Substances 0.000 title 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 title 1
- -1 Triazole ketones Chemical class 0.000 claims description 159
- 150000001875 compounds Chemical class 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 55
- 239000004480 active ingredient Substances 0.000 claims description 52
- 230000008569 process Effects 0.000 claims description 47
- 239000002904 solvent Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000003995 emulsifying agent Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000003630 growth substance Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 12
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- GIVBQSUFWURSOS-UHFFFAOYSA-N 1-ethenyltriazole Chemical class C=CN1C=CN=N1 GIVBQSUFWURSOS-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 235000013312 flour Nutrition 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical class Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 2
- 239000002969 artificial stone Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 125000006277 halobenzyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 60
- 230000012010 growth Effects 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 238000009472 formulation Methods 0.000 description 27
- 230000009036 growth inhibition Effects 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 19
- 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 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 229920001577 copolymer Chemical group 0.000 description 16
- CNFMJLVJDNGPHR-UHFFFAOYSA-N 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)=CC1CCCCC1 CNFMJLVJDNGPHR-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000003306 harvesting Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000003556 assay Methods 0.000 description 10
- 229910052751 metal Chemical class 0.000 description 10
- 239000002184 metal Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 8
- 229920001213 Polysorbate 20 Polymers 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000021536 Sugar beet Nutrition 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 8
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 230000009105 vegetative growth Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 6
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 5
- LVNLYKURNBAIBO-UHFFFAOYSA-N 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)=CC1CCCCC1 LVNLYKURNBAIBO-UHFFFAOYSA-N 0.000 description 5
- 241001480061 Blumeria graminis Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 230000017066 negative regulation of growth Effects 0.000 description 5
- 239000005648 plant growth regulator Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
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- 238000009835 boiling Methods 0.000 description 4
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- 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 1
- 230000005087 leaf formation Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
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- 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 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 230000001069 nematicidal effect Effects 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
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- 235000019319 peptone Nutrition 0.000 description 1
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 125000004351 phenylcyclohexyl group Chemical group C1(=CC=CC=C1)C1(CCCCC1)* 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 230000001863 plant nutrition Effects 0.000 description 1
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- 235000021395 porridge Nutrition 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792906061 DE2906061A1 (de) | 1979-02-16 | 1979-02-16 | 1-vinyltriazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als wachstumsregulatoren und fungizide |
| DE19792938422 DE2938422A1 (de) | 1979-09-22 | 1979-09-22 | 1-vinyltriazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als wachstumsregulatoren und fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187270B true HU187270B (en) | 1985-12-28 |
Family
ID=25777838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU80348A HU187270B (en) | 1979-02-16 | 1980-02-15 | Plant growth regulating and fungicide compositions containing 1-vinyil-triazole derivatives as active substances further process for preparing the active substances |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US4647302A (en, 2012) |
| EP (1) | EP0015387B1 (en, 2012) |
| AR (1) | AR225756A1 (en, 2012) |
| AU (1) | AU532737B2 (en, 2012) |
| BG (3) | BG31462A3 (en, 2012) |
| BR (1) | BR8000996A (en, 2012) |
| CA (1) | CA1142529A (en, 2012) |
| DD (1) | DD149009A5 (en, 2012) |
| DE (1) | DE3061554D1 (en, 2012) |
| DK (1) | DK162891C (en, 2012) |
| EG (1) | EG14213A (en, 2012) |
| ES (1) | ES488643A1 (en, 2012) |
| FI (1) | FI67377C (en, 2012) |
| GR (1) | GR73922B (en, 2012) |
| HU (1) | HU187270B (en, 2012) |
| IE (1) | IE49397B1 (en, 2012) |
| IL (1) | IL59379A (en, 2012) |
| NZ (1) | NZ192858A (en, 2012) |
| PH (1) | PH16107A (en, 2012) |
| PL (1) | PL124651B1 (en, 2012) |
| PT (1) | PT70808A (en, 2012) |
| RO (1) | RO79266A (en, 2012) |
| TR (1) | TR20915A (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| FR2457858A1 (fr) * | 1979-04-05 | 1980-12-26 | Sumitomo Chemical Co | Isomeres geometriques de 1-triazolylstyrenes 1-substitues |
| DE2929602A1 (de) * | 1979-07-21 | 1981-02-12 | Bayer Ag | Triazolyl-alken-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE3019046A1 (de) * | 1980-05-19 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Triazolyl-vinyl-ketone und -carbinole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE3019045A1 (de) * | 1980-05-19 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Substituierte phenyl-triazolyl-vinylketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| GB2078719B (en) * | 1980-06-02 | 1984-04-26 | Ici Ltd | Heterocyclic compounds |
| DE3044802A1 (de) * | 1980-11-28 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Substituierte 1-phenyl-2-triazolyl-1-penten-3-ole, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide |
| DE3044801A1 (de) * | 1980-11-28 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | Antimikrobielle mittel |
| AU544099B2 (en) * | 1980-12-15 | 1985-05-16 | Sumitomo Chemical Company, Limited | Triazolylpentenols |
| DE3100261A1 (de) * | 1981-01-08 | 1982-08-05 | Basf Ag, 6700 Ludwigshafen | Keten-o,n-acetale, verfahren zu ihrer herstellung, diese enthaltende fungizide und ihre verwendung zur bekaempfung von pilzen |
| DE3221700A1 (de) * | 1982-06-09 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Pflanzenwuchshemmende mittel |
| DE3229274A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylvinyl-ketone und -carbinole |
| DE3231205A1 (de) * | 1982-08-21 | 1984-03-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von e-isomeren von 1-cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-on-derivaten |
| DE3302122A1 (de) * | 1983-01-22 | 1984-07-26 | Bayer Ag, 5090 Leverkusen | (-)-antipode des (e)-1-cyclohexyl-4,4-dimethyl-3- hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens |
| DE3302120A1 (de) * | 1983-01-22 | 1984-07-26 | Bayer Ag, 5090 Leverkusen | (+)-antipode des (e)-1-cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens |
| DE3313719A1 (de) * | 1983-04-15 | 1984-10-18 | Bayer Ag, 5090 Leverkusen | Phosphorylierte azolyl-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE3322818A1 (de) * | 1983-06-24 | 1985-01-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von e-isomeren von 1-cyclohexyl-2-(1,2,4-triazol-1-yl)-1-penten-3-on-derivaten |
| DE3420227A1 (de) * | 1984-05-30 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | Vinylazole, verfahren zu ihrer herstellung und ihre verwendung bei der bekaempfung von pilzen |
| DE3576272D1 (de) * | 1984-12-14 | 1990-04-12 | Sumitomo Chemical Co | Verfahren zur regulierung des wachstums von tulpen. |
| DE3501856A1 (de) * | 1985-01-22 | 1986-07-24 | Bayer Ag, 5090 Leverkusen | Mittel zur regulierung des pflanzenwachstums |
| DE3682711D1 (de) | 1985-06-18 | 1992-01-16 | Ici Plc | Als fungizide verwendbare heterocyclische verbindungen. |
| GB8716650D0 (en) * | 1987-07-15 | 1987-08-19 | Ici Plc | Use of olefinic compounds |
| ES2179961T3 (es) * | 1995-12-21 | 2003-02-01 | Basf Corp | Aminoetoxivinilglicina en combinacion con cloruro de mepiquat. |
| AU1373797A (en) * | 1995-12-21 | 1997-07-17 | Basf Corporation | Low rate application of inhibitors of ethylene biosynthesis or action |
| US5861360A (en) * | 1995-12-21 | 1999-01-19 | Basf Corporation | Encapsulated plant growth regulator formulations and applications |
| US5837653A (en) * | 1995-12-21 | 1998-11-17 | Basf Corporation | Encapsulated plant growth regulator formulations |
| US6255250B1 (en) | 1996-12-20 | 2001-07-03 | Basf Corporation | Plant growth regulators in pyrrolidone solvents |
| US7290895B2 (en) * | 2003-08-08 | 2007-11-06 | Production Resource Group, L.L.C. | File system for a stage lighting array system |
| PE20141468A1 (es) | 2010-12-21 | 2014-11-05 | Bayer Cropscience Lp | Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas |
| WO2013039937A1 (en) | 2011-09-12 | 2013-03-21 | Agraquest, Inc. | Methods of enhancing health and/or promoting growth of a plant and/or of improving fruit ripening |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4086351A (en) * | 1975-10-09 | 1978-04-25 | Imperial Chemical Industries Limited | 1,2,4-Triazole-containing compounds and their use as pesticides |
| IE43731B1 (en) * | 1975-10-09 | 1981-05-26 | Ici Ltd | A-(1,2,4-triazolyl or imidazolyl)-acetophenones and their use as pesticides |
| IE45765B1 (en) * | 1976-08-19 | 1982-11-17 | Ici Ltd | Triazoles and imidazoles useful as plant fungicides and growth regulating agents |
| JPS6053018B2 (ja) * | 1977-09-07 | 1985-11-22 | 住友化学工業株式会社 | アゾ−ル系化合物、その製造法および該化合物からなる殺菌剤 |
| US4182862A (en) * | 1978-10-18 | 1980-01-08 | Rohm And Haas Company | Process for the preparation of 1,3-disubstituted-2-azoyl-2-propen-1-ones |
| DE3019046A1 (de) * | 1980-05-19 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Triazolyl-vinyl-ketone und -carbinole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE3019045A1 (de) * | 1980-05-19 | 1981-11-26 | Bayer Ag, 5090 Leverkusen | Substituierte phenyl-triazolyl-vinylketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
-
1980
- 1980-02-04 DE DE8080100531T patent/DE3061554D1/de not_active Expired
- 1980-02-04 EP EP80100531A patent/EP0015387B1/de not_active Expired
- 1980-02-08 PT PT70808A patent/PT70808A/pt unknown
- 1980-02-11 BG BG046559A patent/BG31462A3/xx unknown
- 1980-02-11 BG BG047628A patent/BG31477A3/xx unknown
- 1980-02-11 BG BG047629A patent/BG31499A3/xx unknown
- 1980-02-13 FI FI800430A patent/FI67377C/fi not_active IP Right Cessation
- 1980-02-13 IL IL59379A patent/IL59379A/xx unknown
- 1980-02-13 AU AU55513/80A patent/AU532737B2/en not_active Ceased
- 1980-02-13 AR AR279950A patent/AR225756A1/es active
- 1980-02-13 NZ NZ192858A patent/NZ192858A/xx unknown
- 1980-02-14 CA CA000345638A patent/CA1142529A/en not_active Expired
- 1980-02-14 GR GR61207A patent/GR73922B/el unknown
- 1980-02-14 DD DD80219061A patent/DD149009A5/de not_active IP Right Cessation
- 1980-02-15 HU HU80348A patent/HU187270B/hu not_active IP Right Cessation
- 1980-02-15 IE IE286/80A patent/IE49397B1/en unknown
- 1980-02-15 BR BR8000996A patent/BR8000996A/pt unknown
- 1980-02-15 PL PL1980222047A patent/PL124651B1/pl unknown
- 1980-02-15 TR TR20915A patent/TR20915A/xx unknown
- 1980-02-15 ES ES488643A patent/ES488643A1/es not_active Expired
- 1980-02-15 DK DK067880A patent/DK162891C/da active
- 1980-02-16 RO RO80100207A patent/RO79266A/ro unknown
- 1980-02-16 EG EG89/80A patent/EG14213A/xx active
- 1980-02-18 PH PH23658A patent/PH16107A/en unknown
-
1984
- 1984-06-12 US US06/619,949 patent/US4647302A/en not_active Expired - Fee Related
-
1986
- 1986-07-30 US US06/894,437 patent/US4743293A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU5551380A (en) | 1980-08-21 |
| DK162891C (da) | 1992-05-11 |
| DE3061554D1 (en) | 1983-02-17 |
| IE800286L (en) | 1980-08-16 |
| NZ192858A (en) | 1982-02-23 |
| US4743293A (en) | 1988-05-10 |
| BR8000996A (pt) | 1980-10-29 |
| PT70808A (en) | 1980-03-01 |
| DK67880A (da) | 1980-08-17 |
| FI67377C (fi) | 1985-03-11 |
| EP0015387A2 (de) | 1980-09-17 |
| AU532737B2 (en) | 1983-10-13 |
| EG14213A (en) | 1983-09-30 |
| IL59379A0 (en) | 1980-05-30 |
| BG31499A3 (bg) | 1982-01-15 |
| DD149009A5 (de) | 1981-06-24 |
| US4647302A (en) | 1987-03-03 |
| BG31462A3 (bg) | 1982-01-15 |
| PH16107A (en) | 1983-06-30 |
| PL124651B1 (en) | 1983-02-28 |
| IL59379A (en) | 1984-07-31 |
| PL222047A1 (en, 2012) | 1982-01-04 |
| TR20915A (tr) | 1982-12-23 |
| ES488643A1 (es) | 1980-09-16 |
| CA1142529A (en) | 1983-03-08 |
| AR225756A1 (es) | 1982-04-30 |
| DK162891B (da) | 1991-12-23 |
| FI800430A7 (fi) | 1980-08-17 |
| FI67377B (fi) | 1984-11-30 |
| IE49397B1 (en) | 1985-10-02 |
| RO79266A (ro) | 1982-06-25 |
| GR73922B (en, 2012) | 1984-05-23 |
| BG31477A3 (bg) | 1982-01-15 |
| EP0015387B1 (de) | 1983-01-12 |
| EP0015387A3 (en) | 1980-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |