DE3048267A1 - Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte - Google Patents
Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukteInfo
- Publication number
- DE3048267A1 DE3048267A1 DE19803048267 DE3048267A DE3048267A1 DE 3048267 A1 DE3048267 A1 DE 3048267A1 DE 19803048267 DE19803048267 DE 19803048267 DE 3048267 A DE3048267 A DE 3048267A DE 3048267 A1 DE3048267 A1 DE 3048267A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- alkyl
- carbon atoms
- substituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000013067 intermediate product Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 45
- -1 methoxy, methylthio, cyclohexyl Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 15
- LBWLKXMHUYWHTF-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)butan-2-ol Chemical class CCC(O)CC1=CC=CN1 LBWLKXMHUYWHTF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052751 metal Chemical class 0.000 claims abstract description 12
- 239000002184 metal Chemical class 0.000 claims abstract description 12
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 8
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims abstract 3
- 239000000460 chlorine Substances 0.000 claims description 169
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000008635 plant growth Effects 0.000 claims description 4
- 239000011814 protection agent Substances 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- SWMBAEIZFIXVTB-UHFFFAOYSA-N 1-(1h-pyrrol-2-yl)butan-2-one Chemical class CCC(=O)CC1=CC=CN1 SWMBAEIZFIXVTB-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 239000004476 plant protection product Substances 0.000 claims 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 69
- 241000196324 Embryophyta Species 0.000 description 49
- 229920000728 polyester Polymers 0.000 description 48
- 150000001875 compounds Chemical class 0.000 description 37
- 239000004480 active ingredient Substances 0.000 description 26
- 239000003630 growth substance Substances 0.000 description 21
- 230000012010 growth Effects 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000003306 harvesting Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 235000013399 edible fruits Nutrition 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 206010061217 Infestation Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000009105 vegetative growth Effects 0.000 description 5
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 235000021536 Sugar beet Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 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 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000035613 defoliation Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
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- 239000010695 polyglycol Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CWRQPRXVSJTXNZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)propan-1-ol Chemical compound C1=NC=NN1C(C)C(O)C1=CC=C(Cl)C=C1 CWRQPRXVSJTXNZ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
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- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
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Classifications
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Luminescent Compositions (AREA)
- Light Receiving Elements (AREA)
- Fertilizers (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048267 DE3048267A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
| DE8181110222T DE3165591D1 (en) | 1980-12-20 | 1981-12-08 | Substituted 1-azolyl-2-ol butanes, their preparation and their application as plant protection agents and as intermediates |
| EP81110222A EP0055833B1 (de) | 1980-12-20 | 1981-12-08 | Substituierte 1-Azolyl-butan-2-ole, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenschutzmittel sowie als Zwischenprodukte |
| AT81110222T ATE8992T1 (de) | 1980-12-20 | 1981-12-08 | Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte. |
| PT74110A PT74110B (en) | 1980-12-20 | 1981-12-10 | Process for the preparation of substituted 1-azolyl-butan-2-ols having fungicidal and plant growth regulation effects |
| AU78547/81A AU541359B2 (en) | 1980-12-20 | 1981-12-16 | 1,2,4-triazolyl- and imidazolyl-butan-2-ol derivatives |
| IL64571A IL64571A0 (en) | 1980-12-20 | 1981-12-17 | Substituted 1-azolyl-butan-2-ols,their preparation and their use as plant protection agents and as intermediate products |
| JP56203840A JPS57128675A (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butan-2-ols, manufacture and use |
| GR66842A GR77635B (en, 2012) | 1980-12-20 | 1981-12-18 | |
| HU813866A HU188726B (en) | 1980-12-20 | 1981-12-18 | Plant protective substances containing 1-azolyl-buthan-2-ol derivatives as active substances and process for preparing the active substances |
| ES508133A ES8306478A1 (es) | 1980-12-20 | 1981-12-18 | Procedimiento para la obtencion de 1-azolil-butan-2-oles sustituidos. |
| CA000392731A CA1177076A (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butan-2-ols, a process for their preparation and their use as plant protection agents and as intermediate products |
| AR287857A AR228764A1 (es) | 1980-12-20 | 1981-12-18 | 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 |
| BR8108260A BR8108260A (pt) | 1980-12-20 | 1981-12-18 | 1-azolil-butano-2-ois substituidos,processo para sua preparacao,composicoes protetoras de plantas,processos para o combate de fungos e para a regulacao do crescimento de plantas,aplicacoes dos ditos compostos,e processo para preparacao de tais composicoes |
| DK563581A DK563581A (da) | 1980-12-20 | 1981-12-18 | Substituerede 1-azolylbutan-2-oler og deres syreadditionssalte og metalsaltkomplekser fremgangsmaade til deres fremstolling og deres anvendelse som plantebeskyttelsesmidler og plantevaekstregulatorer |
| ZA818758A ZA818758B (en) | 1980-12-20 | 1981-12-18 | Substituted 1-azolyl-butan-2-ols,a process for their preparation and their use as plant protection agents and as intermediate products |
| EG760/81A EG15266A (en) | 1980-12-20 | 1981-12-20 | Substituted 1-azolyl-butan-2-ols a process for their preparation and their use as plant protection agents and as intermediate products |
| US06/481,615 US4549900A (en) | 1980-12-20 | 1983-04-04 | Combating fungi with substituted 1-azolyl-butan-2-ones and -2-ols |
| US07/169,912 US4904297A (en) | 1980-12-20 | 1988-03-18 | Combating fungi with substituted 1-azolyl-butan-2-ones and -2-ols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803048267 DE3048267A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3048267A1 true DE3048267A1 (de) | 1982-07-15 |
Family
ID=6119803
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803048267 Withdrawn DE3048267A1 (de) | 1980-12-20 | 1980-12-20 | Substituierte 1-azolyl-butan-2-ole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
| DE8181110222T Expired DE3165591D1 (en) | 1980-12-20 | 1981-12-08 | Substituted 1-azolyl-2-ol butanes, their preparation and their application as plant protection agents and as intermediates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181110222T Expired DE3165591D1 (en) | 1980-12-20 | 1981-12-08 | Substituted 1-azolyl-2-ol butanes, their preparation and their application as plant protection agents and as intermediates |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0055833B1 (en, 2012) |
| JP (1) | JPS57128675A (en, 2012) |
| AT (1) | ATE8992T1 (en, 2012) |
| AU (1) | AU541359B2 (en, 2012) |
| BR (1) | BR8108260A (en, 2012) |
| CA (1) | CA1177076A (en, 2012) |
| DE (2) | DE3048267A1 (en, 2012) |
| DK (1) | DK563581A (en, 2012) |
| EG (1) | EG15266A (en, 2012) |
| ES (1) | ES8306478A1 (en, 2012) |
| GR (1) | GR77635B (en, 2012) |
| HU (1) | HU188726B (en, 2012) |
| IL (1) | IL64571A0 (en, 2012) |
| PT (1) | PT74110B (en, 2012) |
| ZA (1) | ZA818758B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108995A1 (de) * | 1982-11-15 | 1984-05-23 | Bayer Ag | Hydroxyalkinyl-azolyl-Derivate |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5862163A (ja) * | 1981-10-09 | 1983-04-13 | Sumitomo Chem Co Ltd | イミダゾリルカルボン酸誘導体 |
| DE3151440A1 (de) * | 1981-12-24 | 1983-07-07 | Bayer Ag, 5090 Leverkusen | Antimykotische mittel |
| US4940481A (en) * | 1982-03-04 | 1990-07-10 | Ciba-Geigy Corporation | Microbicidal and growth regulating compositions |
| DE3209431A1 (de) * | 1982-03-16 | 1983-09-22 | Bayer Ag, 5090 Leverkusen | Phenoxypropyltriazolyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE3229273A1 (de) * | 1982-08-05 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Substituierte azolylallyl-ketone und -carbinole |
| DE3378764D1 (en) * | 1982-09-30 | 1989-02-02 | Pfizer Ltd | Triazole anti-fungal agents |
| GB8312624D0 (en) * | 1983-05-07 | 1983-06-08 | Pfizer Ltd | Triazole antifungal agents |
| PH19347A (en) * | 1982-09-30 | 1986-04-02 | Pfizer | Triazole derivatives,pharmaceutical composition containing same and method of use thereof |
| US4505919A (en) * | 1982-10-09 | 1985-03-19 | Pfizer Inc. | Antifungal S-arylmethyl- and S-heterocyclylmethyl ethers of 2-aryl-3-mercapto-1-(1H-1,2,4-triazol-1-yl) propan-2-ols |
| DE3245504A1 (de) * | 1982-12-09 | 1984-06-14 | Bayer Ag, 5090 Leverkusen | Fungizide mittel, deren herstellung und verwendung |
| DE3313941A1 (de) * | 1983-04-15 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-azolyl-pentannitrile, verfahren zur herstellung dieser verbundungen sowie diese enthaltende biozide mittel |
| DE3322526A1 (de) * | 1983-06-23 | 1985-01-10 | Basf Ag, 6700 Ludwigshafen | Fungizide azolverbindungen, ihre herstellung und verwendung |
| US4602030A (en) * | 1984-05-24 | 1986-07-22 | Chevron Research Company | Fungicidal 2-substituted-1-(1-imidazolyl)-propyl aryl sulfides, sulfoxides and sulfones |
| DE3434158A1 (de) * | 1984-09-18 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Substituierte 1,1-bis-azolyl-butan-2-one und -ole |
| GB8601952D0 (en) * | 1986-01-28 | 1986-03-05 | Ici Plc | Heterocyclic compounds |
| DE3721695A1 (de) * | 1987-07-01 | 1989-01-12 | Bayer Ag | 1-phenoxy-3-triazolyl-1-hexen-derivate |
| DE3725397A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | 1,4-disubstituierte 1-azolyl-3,3-dimethylbutan-derivate |
| DE3813253A1 (de) * | 1988-04-20 | 1989-11-02 | Bayer Ag | Substituierte triazolylmethylcarbinole |
| DE4222542A1 (de) * | 1992-07-09 | 1994-01-13 | Bayer Ag | Triazolyl-butan-Derivate |
| DE4222541A1 (de) * | 1992-07-09 | 1994-01-13 | Bayer Ag | Triazolyl-butan-Derivate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2908378A1 (de) * | 1979-03-03 | 1980-09-11 | Hoechst Ag | Derivate des 1,2,4-triazols |
| DE2920437A1 (de) * | 1979-05-19 | 1980-11-27 | Bayer Ag | Geometrische isomere von 4,4- dimethyl-1-phenyl-2-(1,2,4-triazol-1-yl)- 1-penten-3-olen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2951163A1 (de) * | 1979-12-19 | 1981-07-16 | Bayer Ag, 5090 Leverkusen | Substituierte triazolylmethyl-tert.-butyl-carbinole, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel sowie als zwischenprodukte |
-
1980
- 1980-12-20 DE DE19803048267 patent/DE3048267A1/de not_active Withdrawn
-
1981
- 1981-12-08 EP EP81110222A patent/EP0055833B1/de not_active Expired
- 1981-12-08 DE DE8181110222T patent/DE3165591D1/de not_active Expired
- 1981-12-08 AT AT81110222T patent/ATE8992T1/de active
- 1981-12-10 PT PT74110A patent/PT74110B/pt unknown
- 1981-12-16 AU AU78547/81A patent/AU541359B2/en not_active Ceased
- 1981-12-17 IL IL64571A patent/IL64571A0/xx unknown
- 1981-12-18 CA CA000392731A patent/CA1177076A/en not_active Expired
- 1981-12-18 HU HU813866A patent/HU188726B/hu not_active IP Right Cessation
- 1981-12-18 ZA ZA818758A patent/ZA818758B/xx unknown
- 1981-12-18 GR GR66842A patent/GR77635B/el unknown
- 1981-12-18 DK DK563581A patent/DK563581A/da not_active Application Discontinuation
- 1981-12-18 BR BR8108260A patent/BR8108260A/pt not_active Application Discontinuation
- 1981-12-18 ES ES508133A patent/ES8306478A1/es not_active Expired
- 1981-12-18 JP JP56203840A patent/JPS57128675A/ja active Granted
- 1981-12-20 EG EG760/81A patent/EG15266A/xx active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108995A1 (de) * | 1982-11-15 | 1984-05-23 | Bayer Ag | Hydroxyalkinyl-azolyl-Derivate |
| US4622333A (en) * | 1982-11-15 | 1986-11-11 | Bayer Aktiengesellschaft | Fungicidal hydroxyalkynyl-azolyl derivatives |
| US4818762A (en) * | 1982-11-15 | 1989-04-04 | Bayer Aktiengesellschaft | Fungicidal novel hydroxyalkynyl-azolyl derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1177076A (en) | 1984-10-30 |
| JPH0216301B2 (en, 2012) | 1990-04-16 |
| EP0055833A1 (de) | 1982-07-14 |
| ES508133A0 (es) | 1983-06-01 |
| BR8108260A (pt) | 1982-10-05 |
| EG15266A (en) | 1987-04-30 |
| HU188726B (en) | 1986-05-28 |
| ES8306478A1 (es) | 1983-06-01 |
| ZA818758B (en) | 1982-11-24 |
| EP0055833B1 (de) | 1984-08-15 |
| JPS57128675A (en) | 1982-08-10 |
| PT74110B (en) | 1983-05-16 |
| IL64571A0 (en) | 1982-03-31 |
| PT74110A (en) | 1982-01-01 |
| ATE8992T1 (de) | 1984-09-15 |
| DK563581A (da) | 1982-06-21 |
| GR77635B (en, 2012) | 1984-09-25 |
| AU7854781A (en) | 1982-07-01 |
| DE3165591D1 (en) | 1984-09-20 |
| AU541359B2 (en) | 1985-01-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |