HU187740B - Fungicides containing pyridine-carbinols and process for the produktion of active substances - Google Patents
Fungicides containing pyridine-carbinols and process for the produktion of active substances Download PDFInfo
- Publication number
- HU187740B HU187740B HU822220A HU222082A HU187740B HU 187740 B HU187740 B HU 187740B HU 822220 A HU822220 A HU 822220A HU 222082 A HU222082 A HU 222082A HU 187740 B HU187740 B HU 187740B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- hydrogen
- alkyl
- butyl
- methyl
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims abstract description 9
- VRWLBMGRSLQKSU-UHFFFAOYSA-N methanol;pyridine Chemical class OC.C1=CC=NC=C1 VRWLBMGRSLQKSU-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 239000013543 active substance Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 30
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical group [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000011734 sodium Chemical group 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical group [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
- 229910001623 magnesium bromide Chemical group 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001804 emulsifying effect Effects 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- -1 1- (3-pyridyl) -2-benzyl-1-ethanol derivatives Chemical class 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000003795 chemical substances by application Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000004480 active ingredient Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- 239000007921 spray Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- 241000220225 Malus Species 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- 208000031888 Mycoses Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 3
- XEZSLVWHMVRPHW-UHFFFAOYSA-N 4,4-dimethyl-1-pyridin-3-ylpent-2-en-1-one Chemical compound CC(C)(C)C=CC(=O)C1=CC=CN=C1 XEZSLVWHMVRPHW-UHFFFAOYSA-N 0.000 description 3
- 235000000832 Ayote Nutrition 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- 235000009854 Cucurbita moschata Nutrition 0.000 description 3
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 3
- 241000510928 Erysiphe necator Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000015136 pumpkin Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QSZOMCLHJKGKED-UHFFFAOYSA-N 2-carbamothioylsulfanylpropyl carbamodithioate Chemical compound NC(=S)SC(C)CSC(N)=S QSZOMCLHJKGKED-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
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- 240000004244 Cucurbita moschata Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 229960000583 acetic acid Drugs 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
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- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
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- 239000004009 herbicide Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229940044654 phenolsulfonic acid Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- AIPJZPPOFWCJRC-UHFFFAOYSA-N 1,2-dichloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1Cl AIPJZPPOFWCJRC-UHFFFAOYSA-N 0.000 description 1
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- ZJZCLBZCGKRRQQ-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5,5-dimethyl-2-pyridin-3-ylhex-3-en-2-ol Chemical compound CC(C=CC(O)(C=1C=NC=CC=1)CC1=C(C=C(C=C1)Cl)Cl)(C)C ZJZCLBZCGKRRQQ-UHFFFAOYSA-N 0.000 description 1
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- GPUKMTQLSWHBLZ-UHFFFAOYSA-N 1-phenyltridecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCC(S(O)(=O)=O)C1=CC=CC=C1 GPUKMTQLSWHBLZ-UHFFFAOYSA-N 0.000 description 1
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- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813126819 DE3126819A1 (de) | 1981-07-08 | 1981-07-08 | Pyridincarbinole, verfahren zu ihrer herstellung und diese enthaltende fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU187740B true HU187740B (en) | 1986-02-28 |
Family
ID=6136329
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822220A HU187740B (en) | 1981-07-08 | 1982-07-07 | Fungicides containing pyridine-carbinols and process for the produktion of active substances |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4431812A (en, 2012) |
| EP (1) | EP0069330B1 (en, 2012) |
| JP (1) | JPS5823665A (en, 2012) |
| KR (1) | KR880002228B1 (en, 2012) |
| AT (1) | ATE11133T1 (en, 2012) |
| AU (1) | AU562515B2 (en, 2012) |
| CA (1) | CA1176636A (en, 2012) |
| CS (1) | CS229689B2 (en, 2012) |
| DD (1) | DD202089A5 (en, 2012) |
| DE (2) | DE3126819A1 (en, 2012) |
| GB (1) | GB2104890B (en, 2012) |
| HU (1) | HU187740B (en, 2012) |
| IL (1) | IL66152A0 (en, 2012) |
| IN (1) | IN155341B (en, 2012) |
| MY (1) | MY8600420A (en, 2012) |
| NZ (1) | NZ201196A (en, 2012) |
| PL (1) | PL130636B2 (en, 2012) |
| ZA (1) | ZA824813B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU554104B2 (en) * | 1981-09-01 | 1986-08-07 | F. Hoffmann-La Roche Ag | Heterocyclic compounds and fungicides containing same |
| EP0117485A3 (de) * | 1983-02-28 | 1985-01-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridin-, Pyrazin- und Pyrimidinderivate und deren Verwendung als fungizide Wirkstoffe |
| DE3476543D1 (en) * | 1983-05-19 | 1989-03-09 | Ciba Geigy Ag | Microbicides |
| DK429884A (da) * | 1983-10-07 | 1985-04-08 | Hoffmann La Roche | Heterocycliske forbindelser |
| US4699652A (en) * | 1985-07-22 | 1987-10-13 | Hoffmann-La Roche Inc. | Fungicidal pyridine derivatives for use in agriculture |
| DE3734750A1 (de) * | 1987-10-14 | 1989-04-27 | Basf Ag | 3-substituierte pyridine und diese enthaltende fungizide |
| DE3744620A1 (de) * | 1987-12-31 | 1989-07-13 | Basf Ag | Pyridin-n-oxide und diese enthaltende fungizide |
| GB8814639D0 (en) * | 1988-06-20 | 1988-07-27 | Ici Plc | Heterocyclic tertiary alcohol derivatives |
| DE4004317A1 (de) * | 1990-02-13 | 1991-08-14 | Basf Ag | Neue 3-substituierte pyridinmethanole und diese enthaltende fungizide |
| DE19917160A1 (de) * | 1999-04-16 | 2000-10-19 | Bayer Ag | Disubstituierte Pyridine und Pyrimidine |
| US7541472B2 (en) * | 2004-05-24 | 2009-06-02 | Cropsolution, Inc. | 3-Aryl-3-hydroxy-2-methylenepropionic acid esters as fungicides |
| CN110885365B (zh) * | 2019-12-11 | 2022-05-10 | 海南大学 | Ataf2蛋白及其相关生物材料在调控植物对橡胶树白粉菌的抗病性中的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2863802A (en) * | 1957-04-11 | 1958-12-09 | Diamond Alkali Co | Treating plants with the systemically active fungicide, lower alkyl, 2(3, 3, 3-trihalo-2-hydroxypropyl)-pyridine |
| US3396224A (en) * | 1965-09-09 | 1968-08-06 | Lilly Co Eli | Controlling phytopathogenic fungi on plants with 3-pyridyl methane derivatives |
| US3397273A (en) * | 1966-02-18 | 1968-08-13 | Lilly Co Eli | Controlling phytopathogenic fungi on plants with 3-pyridyl methane derivatives |
| US3655359A (en) * | 1969-10-16 | 1972-04-11 | Lilly Co Eli | Plant growth control |
| GB1337359A (en) * | 1971-04-19 | 1973-11-14 | Sumitomo Chemical Co | Imidocarbonates processes for producing them and compositions containing them |
| US4039675A (en) * | 1972-09-15 | 1977-08-02 | Eli Lilly And Company | α,α-Dialkyl-substituted 3-pyridinemethanols as fungicidal agents |
| US4116665A (en) * | 1976-04-02 | 1978-09-26 | Eli Lilly And Company | Method of regulating the growth of aquatic weeds with pyridine derivatives |
| DE2659117A1 (de) * | 1976-12-28 | 1978-07-06 | Consortium Elektrochem Ind | Trichlormethyl-(3-pyridyl)-carbinol |
| DE2742173A1 (de) * | 1977-09-20 | 1979-03-29 | Bayer Ag | Phenoxy-pyridinyl(pyrimidinyl)-alkanole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| JPS5498331A (en) * | 1978-01-07 | 1979-08-03 | Lilly Co Eli | Agent and method for controlling aqueous weeds |
-
1981
- 1981-07-08 DE DE19813126819 patent/DE3126819A1/de not_active Withdrawn
-
1982
- 1982-06-28 IL IL66152A patent/IL66152A0/xx not_active IP Right Cessation
- 1982-06-30 DE DE8282105805T patent/DE3261844D1/de not_active Expired
- 1982-06-30 EP EP82105805A patent/EP0069330B1/de not_active Expired
- 1982-06-30 AT AT82105805T patent/ATE11133T1/de not_active IP Right Cessation
- 1982-07-01 US US06/394,185 patent/US4431812A/en not_active Expired - Fee Related
- 1982-07-02 JP JP57114123A patent/JPS5823665A/ja active Granted
- 1982-07-05 CA CA000406612A patent/CA1176636A/en not_active Expired
- 1982-07-05 IN IN782/CAL/82A patent/IN155341B/en unknown
- 1982-07-06 DD DD82241444A patent/DD202089A5/de unknown
- 1982-07-06 PL PL1982237304A patent/PL130636B2/xx unknown
- 1982-07-07 AU AU85704/82A patent/AU562515B2/en not_active Ceased
- 1982-07-07 GB GB08219657A patent/GB2104890B/en not_active Expired
- 1982-07-07 HU HU822220A patent/HU187740B/hu not_active IP Right Cessation
- 1982-07-07 ZA ZA824813A patent/ZA824813B/xx unknown
- 1982-07-07 NZ NZ201196A patent/NZ201196A/en unknown
- 1982-07-08 CS CS825226A patent/CS229689B2/cs unknown
- 1982-07-08 KR KR8203044A patent/KR880002228B1/ko not_active Expired
-
1986
- 1986-12-30 MY MY420/86A patent/MY8600420A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0261945B2 (en, 2012) | 1990-12-21 |
| KR840000497A (ko) | 1984-02-22 |
| IL66152A0 (en) | 1982-09-30 |
| US4431812A (en) | 1984-02-14 |
| GB2104890B (en) | 1985-08-07 |
| DE3126819A1 (de) | 1983-01-27 |
| CA1176636A (en) | 1984-10-23 |
| CS229689B2 (en) | 1984-06-18 |
| KR880002228B1 (ko) | 1988-10-20 |
| DD202089A5 (de) | 1983-08-31 |
| PL130636B2 (en) | 1984-08-31 |
| AU8570482A (en) | 1983-01-13 |
| EP0069330A1 (de) | 1983-01-12 |
| GB2104890A (en) | 1983-03-16 |
| NZ201196A (en) | 1984-12-14 |
| ZA824813B (en) | 1983-05-25 |
| EP0069330B1 (de) | 1985-01-09 |
| MY8600420A (en) | 1986-12-31 |
| PL237304A2 (en) | 1983-03-14 |
| JPS5823665A (ja) | 1983-02-12 |
| AU562515B2 (en) | 1987-06-11 |
| IN155341B (en, 2012) | 1985-01-19 |
| ATE11133T1 (de) | 1985-01-15 |
| DE3261844D1 (en) | 1985-02-21 |
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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 |