HU195907B - Fungicidal composition comprising 1-triazolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivative as active ingredient and process for producing 1-azolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivatives - Google Patents
Fungicidal composition comprising 1-triazolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivative as active ingredient and process for producing 1-azolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivatives Download PDFInfo
- Publication number
- HU195907B HU195907B HU84655A HU65584A HU195907B HU 195907 B HU195907 B HU 195907B HU 84655 A HU84655 A HU 84655A HU 65584 A HU65584 A HU 65584A HU 195907 B HU195907 B HU 195907B
- Authority
- HU
- Hungary
- Prior art keywords
- cyclopropyl
- hydrogen
- phenyl
- propan
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 17
- 239000004480 active ingredient Substances 0.000 title claims description 19
- UOLZQNBMCWXHNR-UHFFFAOYSA-N 1-cyclopropyl-2-phenyl-3-(1H-pyrrol-2-yl)propan-2-ol Chemical class N1C(=CC=C1)CC(CC1CC1)(O)C1=CC=CC=C1 UOLZQNBMCWXHNR-UHFFFAOYSA-N 0.000 title claims 2
- QUTIWDZIVNKOMP-UHFFFAOYSA-N 1-cyclopropyl-2-phenyl-3-(2H-triazol-4-yl)propan-2-ol Chemical class N1N=NC(=C1)CC(CC1CC1)(O)C1=CC=CC=C1 QUTIWDZIVNKOMP-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical group 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 235000012211 aluminium silicate Nutrition 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000005909 Kieselgur Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 229920001732 Lignosulfonate Polymers 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 56
- 208000031888 Mycoses Diseases 0.000 abstract description 6
- 241000233866 Fungi Species 0.000 abstract description 4
- 239000000417 fungicide Substances 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000003032 phytopathogenic effect Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- -1 1-azolyl-2-phenyl-3-cyclopropyl- Chemical group 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000209140 Triticum Species 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 241000220225 Malus Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 241000896242 Podosphaera Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000221576 Uromyces Species 0.000 description 3
- 241000219094 Vitaceae Species 0.000 description 3
- 235000009754 Vitis X bourquina Nutrition 0.000 description 3
- 235000012333 Vitis X labruscana Nutrition 0.000 description 3
- 240000006365 Vitis vinifera Species 0.000 description 3
- 235000014787 Vitis vinifera Nutrition 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 235000021021 grapes Nutrition 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 2
- SVSQETXNYGNLQB-UHFFFAOYSA-N (4-chlorophenyl)-(1-cyclopropylcyclopropyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1(C2CC2)CC1 SVSQETXNYGNLQB-UHFFFAOYSA-N 0.000 description 2
- BMIJDNJCYGHLIJ-UHFFFAOYSA-N 1,3-bis(4-chlorophenyl)-1,3-dicyclopropylpropan-2-one Chemical compound C1=CC(Cl)=CC=C1C(C(=O)C(C1CC1)C=1C=CC(Cl)=CC=1)C1CC1 BMIJDNJCYGHLIJ-UHFFFAOYSA-N 0.000 description 2
- WAKBGVGRUCMZFV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-cyclopropyl-2-methylpropan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(C)(C)C1CC1 WAKBGVGRUCMZFV-UHFFFAOYSA-N 0.000 description 2
- QKCYUBJJPXLRFJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-cyclopropylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CC1CC1 QKCYUBJJPXLRFJ-UHFFFAOYSA-N 0.000 description 2
- LRWCURGZPQWMRG-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-cyclopropylpropan-1-one Chemical compound C=1C=C(Cl)C=CC=1C(=O)C(C)C1CC1 LRWCURGZPQWMRG-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000235349 Ascomycota Species 0.000 description 2
- 235000009849 Cucumis sativus Nutrition 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000208152 Geranium Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 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
- 241000699670 Mus sp. Species 0.000 description 2
- 241000221300 Puccinia Species 0.000 description 2
- 241000221535 Pucciniales Species 0.000 description 2
- 241001533598 Septoria Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 241000510929 Uncinula Species 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000001857 anti-mycotic effect Effects 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- MZMJHXFYLRTLQX-UHFFFAOYSA-N ethenylsulfinylbenzene Chemical compound C=CS(=O)C1=CC=CC=C1 MZMJHXFYLRTLQX-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960004125 ketoconazole Drugs 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 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 2
- 239000012044 organic layer Substances 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- SZIBSUZUPGRNEE-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-cyclopropyl-2-methoxy-3-methylbutyl]-1,2,4-triazole Chemical compound C=1C=C(Cl)C=CC=1C(C(C)(C)C1CC1)(OC)CN1C=NC=N1 SZIBSUZUPGRNEE-UHFFFAOYSA-N 0.000 description 1
- CNWYHNVDYQNCOF-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-3-cyclopropyl-3-methyl-2-phenylmethoxybutyl]-1,2,4-triazole Chemical compound ClC1=CC=C(C=C1)C(CN1N=CN=C1)(C(C)(C)C1CC1)OCC1=CC=CC=C1 CNWYHNVDYQNCOF-UHFFFAOYSA-N 0.000 description 1
- 125000006451 1-cyclopropyl cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- FIEMNCUPUKWJBC-UHFFFAOYSA-N 2-methylprop-1-ene-1-thiol Chemical class CC(C)=CS FIEMNCUPUKWJBC-UHFFFAOYSA-N 0.000 description 1
- ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 2-pyrrol-1-ylethanol Chemical compound OCCN1C=CC=C1 ZIOLCZCJJJNOEJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- 239000005747 Chlorothalonil Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241001529717 Corticium <basidiomycota> Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 241001181537 Hemileia Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000005802 Mancozeb Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241001503951 Phoma Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 101150059476 SLC44A3 gene Proteins 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000107946 Spondias cytherea Species 0.000 description 1
- 241000222646 Stereum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000865903 Thielaviopsis Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 241000221566 Ustilago Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 201000007096 Vulvovaginal Candidiasis Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JHRWWRDRBPCWTF-UHFFFAOYSA-N captafol Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)C21 JHRWWRDRBPCWTF-UHFFFAOYSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002925 oxirenes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plant Pathology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1196/83A CH658654A5 (de) | 1983-03-04 | 1983-03-04 | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU195907B true HU195907B (en) | 1988-08-29 |
Family
ID=4204755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU84655A HU195907B (en) | 1983-03-04 | 1984-02-20 | Fungicidal composition comprising 1-triazolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivative as active ingredient and process for producing 1-azolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivatives |
Country Status (35)
| Country | Link |
|---|---|
| US (2) | US4664696A (OSRAM) |
| JP (1) | JPH06756B2 (OSRAM) |
| AT (1) | AT387219B (OSRAM) |
| AU (1) | AU571490B2 (OSRAM) |
| BE (1) | BE899008A (OSRAM) |
| BR (1) | BR8400958A (OSRAM) |
| CA (1) | CA1232278A (OSRAM) |
| CH (1) | CH658654A5 (OSRAM) |
| CS (1) | CS251081B2 (OSRAM) |
| DE (1) | DE3406993A1 (OSRAM) |
| DK (1) | DK165407C (OSRAM) |
| DZ (1) | DZ613A1 (OSRAM) |
| EG (1) | EG16963A (OSRAM) |
| ES (1) | ES8506642A1 (OSRAM) |
| FI (1) | FI81784C (OSRAM) |
| FR (1) | FR2542000B1 (OSRAM) |
| GB (1) | GB2136423B (OSRAM) |
| GR (1) | GR82344B (OSRAM) |
| HU (1) | HU195907B (OSRAM) |
| IE (1) | IE57003B1 (OSRAM) |
| IL (1) | IL71126A (OSRAM) |
| IT (1) | IT1199079B (OSRAM) |
| KE (1) | KE3832A (OSRAM) |
| LU (1) | LU85237A1 (OSRAM) |
| MY (1) | MY8700767A (OSRAM) |
| NL (1) | NL189564C (OSRAM) |
| NZ (1) | NZ207359A (OSRAM) |
| PH (1) | PH22915A (OSRAM) |
| PL (1) | PL139662B1 (OSRAM) |
| PT (1) | PT78192B (OSRAM) |
| SE (1) | SE456678B (OSRAM) |
| SU (1) | SU1416058A3 (OSRAM) |
| TR (1) | TR22432A (OSRAM) |
| UA (1) | UA7048A1 (OSRAM) |
| ZA (1) | ZA841606B (OSRAM) |
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
| CH668772A5 (de) * | 1984-07-13 | 1989-01-31 | Sandoz Ag | 1,2,4-triazol-derivat, verfahren zu dessen herstellung und seine verwendung. |
| CN1008735B (zh) * | 1984-11-02 | 1990-07-11 | 拜尔公司 | 以取代的氮杂茂基甲基-环丙基-甲醇衍生物为活性成分的组合物 |
| EP0180850A3 (de) * | 1984-11-02 | 1987-05-27 | Bayer Ag | Antimykotische Azolylmethyl-cyclopropyl-carbinol Derivate |
| GB8429932D0 (en) * | 1984-11-27 | 1985-01-03 | Pfizer Ltd | Triazole antifungal agents |
| GB8614367D0 (en) * | 1986-06-12 | 1986-07-16 | Sandoz Ltd | Fungicides |
| GB8617780D0 (en) * | 1986-07-21 | 1986-08-28 | Sandoz Ltd | Fungicides |
| GB8629360D0 (en) * | 1986-12-09 | 1987-01-21 | Sandoz Ltd | Fungicides |
| FR2609368B1 (fr) * | 1987-01-14 | 1990-04-13 | Sandoz Sa Produits | Utilisation de derives du 1, 2, 4-triazole pour combattre les maladies de plaies de taille des plantes perennes |
| DE3800094C2 (de) * | 1987-01-14 | 1998-05-14 | Ciba Geigy Ag | Verfahren und hydrophobe Zubereitung zur Bekämpfung von Schnittwundparasiten bei Pflanzen |
| KR920002878B1 (ko) * | 1987-03-19 | 1992-04-06 | 산요덴끼 가부시끼가이샤 | 자동판매기의 표시장치 |
| DE3732388A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Azolylmethylcyclopropyl-carbinole enthaltende antimykotische mittel |
| DE3732387A1 (de) * | 1987-09-25 | 1989-04-06 | Bayer Ag | Azolylmethylcyclopropyl-derivate enthaltende antimykotische mittel |
| IT1232943B (it) * | 1987-11-09 | 1992-03-10 | Mini Ricerca Scient Tecnolog | Azolilderivati fungicidi. |
| US5219876A (en) * | 1987-12-02 | 1993-06-15 | Sandoz Ltd. | Substituted-cyano-2-[4-(phenyl-ethynyl)phenyl]-1-1 (1H-1,2,4-triazol-1-yl)ethane derivatives |
| GB8729107D0 (en) * | 1987-12-14 | 1988-01-27 | Ici Plc | Chemical process |
| DK105189A (da) * | 1988-03-04 | 1989-09-05 | Sankyo Co | Triazolderivater og fremgangsmaade til fremstilling deraf samt fungicide midler indeholdende derivaterne |
| BE1001499A5 (fr) * | 1988-07-14 | 1989-11-14 | Sandoz Sa | Procede pour combattre les maladies de plaies de taille des plantes perennes. |
| DE3834875A1 (de) * | 1988-10-13 | 1990-04-19 | Sandoz Ag | Staubfreie zusammensetzungen |
| ZA914221B (en) | 1990-06-05 | 1992-03-25 | Ciba Geigy | Aromatic compounds |
| EP0683980B1 (de) * | 1990-11-02 | 1999-03-24 | Novartis AG | Fungizide Mittel |
| US5156832A (en) * | 1991-03-18 | 1992-10-20 | Sandoz Ltd. | Compositions containing cyproconazole and rose bengal |
| DE59206041D1 (de) * | 1991-12-19 | 1996-05-23 | Ciba Geigy Ag | Mikrobizide |
| US6423732B1 (en) * | 1992-02-04 | 2002-07-23 | Syngenta Participations Ag | Synergistic combinations of cyproconazole |
| GB9202378D0 (en) * | 1992-02-05 | 1992-03-18 | Sandoz Ltd | Inventions relating to fungicidal compositions |
| ATE160483T1 (de) * | 1992-02-13 | 1997-12-15 | Ciba Geigy Ag | Fungizide mischungen auf der basis von triazol- fungiziden und 4,6-dimethyl-n-phenyl-2- pyrimidinamin |
| DE4325517A1 (de) * | 1992-07-31 | 1994-02-03 | Shell Int Research | Fungizide Zusammensetzungen |
| USH1400H (en) * | 1992-08-11 | 1995-01-03 | Culbreath; Albert K. | Fungicide |
| DE4233337A1 (de) * | 1992-10-05 | 1994-04-07 | Bayer Ag | Mikrobizide Mittel |
| US5342980A (en) | 1992-12-30 | 1994-08-30 | American Cyanamid Company | Fungicidal agents |
| ATE136734T1 (de) * | 1993-09-24 | 1996-05-15 | Basf Ag | Fungizide mischungen |
| DE69821940T2 (de) | 1997-06-30 | 2005-03-17 | Monsanto Technology Llc | Landwirtschaftlich aktive inhaltsstoffe enthaltende mikropartikel |
| IL149554A0 (en) * | 1999-12-13 | 2002-11-10 | Bayer Ag | Fungicidal combinations of active substances |
| DE10019758A1 (de) * | 2000-04-20 | 2001-10-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10103832A1 (de) * | 2000-05-11 | 2001-11-15 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| NZ534782A (en) * | 2002-03-07 | 2007-07-27 | Basf Ag | Synergistic fungicidal mixtures of prothioconazole with another triazole |
| BR0308830A (pt) * | 2002-04-05 | 2005-01-25 | Basf Ag | Mistura fungicida, processo para combater nocivos, e, agente fungicida |
| DE10347090A1 (de) * | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| JP2007512278A (ja) * | 2003-11-27 | 2007-05-17 | ビーエーエスエフ アクチェンゲゼルシャフト | トリアゾロピリミジン誘導体およびコナゾールに基づく殺菌混合物 |
| EA013507B1 (ru) | 2004-04-30 | 2010-06-30 | Басф Се | Фунгицидные смеси |
| DE102004049761A1 (de) * | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE102005015677A1 (de) * | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| US8754009B2 (en) | 2005-06-09 | 2014-06-17 | Bayer Cropscience Ag | Active compound combinations |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005035300A1 (de) * | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| EP2489266A3 (en) | 2006-09-18 | 2012-10-24 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
| US7772156B2 (en) * | 2006-11-01 | 2010-08-10 | Buckman Laboratories International, Inc. | Microbicidal compositions including a cyanodithiocarbimate and a second microbicide, and methods of using the same |
| EP2258177A3 (en) | 2006-12-15 | 2011-11-09 | Rohm and Haas Company | Mixtures comprising 1-methylcyclopropene |
| EP2679095A1 (en) | 2007-02-06 | 2014-01-01 | Basf Se | Pesticidal mixtures |
| CL2008001181A1 (es) | 2007-04-23 | 2009-10-23 | Basf Se | Metodo para mejorar la salud de la planta y/o controlar plagas en plantas con al menos una modificacion transgenica relacionada con el aumento del rendimiento que consiste en la aplicacion de una composicion quimica que comprende al menos un ingrediente activo seleccionado de insecticidas, fungicidas o herbicidas. |
| EP2000028A1 (de) * | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| PT2205082E (pt) | 2007-09-26 | 2012-05-02 | Basf Se | Composições fungicidas ternárias compreendendo boscalide e clorotalonil |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| AU2009342807B2 (en) | 2009-03-25 | 2015-04-02 | Bayer Cropscience Aktiengesellschaft | Synergistic combinations of active ingredients |
| CN101565406B (zh) * | 2009-04-29 | 2010-11-10 | 江苏七洲绿色化工股份有限公司 | 环唑醇的制备工艺 |
| WO2010142779A1 (en) | 2009-06-12 | 2010-12-16 | Basf Se | Antifungal 1,2,4-triazolyl derivatives having a 5- sulfur substituent |
| JP5642786B2 (ja) | 2009-07-16 | 2014-12-17 | バイエル・クロップサイエンス・アーゲーＢａｙｅｒ Ｃｒｏｐｓｃｉｅｎｃｅ Ａｇ | フェニルトリアゾール類を含む相乗的活性化合物組み合わせ |
| WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
| CN101786948B (zh) * | 2010-01-25 | 2013-01-30 | 江苏省农用激素工程技术研究中心有限公司 | 1-（4-氯苯基）-2-环丙基-1-丙酮的制备方法 |
| CN101857576B (zh) * | 2010-06-18 | 2012-07-25 | 中国科学院上海有机化学研究所 | 通过环丙基甲基酮制备环唑醇的方法 |
| US20140051735A1 (en) * | 2010-08-17 | 2014-02-20 | Bayer Intellectual Property Gmbh | Use of n-phenylethylpyrazole carboxamide derivatives or salts thereof for controlling powdery mildew primary infections |
| EA201300731A1 (ru) | 2010-12-20 | 2014-01-30 | Басф Се | Пестицидно активные смеси, которые содержат соединения пиразола |
| EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
| EP3378313A1 (en) | 2011-03-23 | 2018-09-26 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
| WO2013030338A2 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Agricultural mixtures comprising arylquinazolinone compounds |
| CN102349518B (zh) * | 2011-11-01 | 2013-05-15 | 海利尔药业集团股份有限公司 | 一种含有环唑醇和氟吗啉的杀菌组合物 |
| CN102584558B (zh) * | 2011-12-21 | 2013-10-30 | 湖南化工研究院 | 一种1-(4-氯苯基)-2-环丙基-1-丙酮的制备方法 |
| CN102584726B (zh) * | 2012-01-07 | 2014-05-14 | 浙江禾本科技有限公司 | 一种杀菌剂戊菌唑的制备方法 |
| BR122019015112B1 (pt) | 2012-06-20 | 2020-04-07 | Basf Se | mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal, uso de uma mistura pesticida e métodos para o combate dos fungos fitopatogênicos nocivos e para proteger vegetais de fungos fitopatogênicos nocivos |
| US20150257383A1 (en) | 2012-10-12 | 2015-09-17 | Basf Se | Method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
| WO2014095381A1 (en) | 2012-12-19 | 2014-06-26 | Basf Se | Fungicidal imidazolyl and triazolyl compounds |
| JP6576829B2 (ja) | 2012-12-20 | 2019-09-18 | ビーエーエスエフ アグロ ベー．ブイ． | トリアゾール化合物を含む組成物 |
| EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
| EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
| WO2015032692A1 (de) | 2013-09-03 | 2015-03-12 | Bayer Cropscience Ag | Verwendung fungizider wirkstoffe zur kontrolle von chalara fraxinea an eschenbäumen |
| CN105722833A (zh) | 2013-09-16 | 2016-06-29 | 巴斯夫欧洲公司 | 杀真菌的嘧啶化合物 |
| WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
| BR102013027313B1 (pt) * | 2013-10-23 | 2019-06-18 | Iharabras S.A. Indústrias Químicas | Processo para a preparação seletiva de (1h-1,2,4-triazol-1-il) alcanóis, composto hidrazinil alcanol obtido por tal processo e seu uso |
| EP3122732B1 (en) * | 2014-03-26 | 2018-02-28 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds as fungicides |
| EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
| AU2015334829B2 (en) | 2014-10-24 | 2019-09-12 | Basf Se | Non-amphoteric, quaternisable and water-soluble polymers for modifying the surface charge of solid particles |
| CN105777508B (zh) * | 2014-12-22 | 2019-01-25 | 上海泰禾国际贸易有限公司 | 一种1-(4-氯苯基)-2-环丙基-1-丙酮的合成方法 |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| PL3316692T3 (pl) | 2015-07-02 | 2021-10-11 | BASF Agro B.V. | Kompozycje owadobójcze zawierające związek triazolowy |
| US11185548B2 (en) | 2016-12-23 | 2021-11-30 | Helmholtz Zentrum Munchen—Deutsches Forschungszentrum Für Gesundheit Und Umwelt (Gmbh) | Inhibitors of cytochrome P450 family 7 subfamily B member 1 (CYP7B1) for use in treating diseases |
| CN109020905B (zh) * | 2017-06-09 | 2022-12-23 | 华东理工大学 | 两种环丙唑醇的多晶型及其制备方法 |
| KR20210040945A (ko) | 2018-06-21 | 2021-04-14 | 유마니티 테라퓨틱스, 인크. | 신경장애의 치료 및 예방을 위한 조성물 및 방법 |
| CN109006836A (zh) * | 2018-10-10 | 2018-12-18 | 江苏七洲绿色化工股份有限公司 | 一种含有环丙唑醇的干悬浮剂及其制备方法 |
| CN114401950A (zh) | 2019-09-12 | 2022-04-26 | 赛拓有限责任公司 | 用于由醛或酮制备环氧化物的改进方法 |
| MX2022002847A (es) | 2019-09-12 | 2022-04-06 | Saltigo Gmbh | Procedimiento mejorado para la preparacion de compuestos de ciclopropilo a partir de alquenos. |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654332A (en) * | 1979-03-07 | 1987-03-31 | Imperial Chemical Industries Plc | Heterocyclic compounds |
| EP0023103A1 (en) * | 1979-07-04 | 1981-01-28 | Pfizer Limited | Antifungal imidazole derivatives, process for their preparation and pharmaceutical compositions thereof |
| US4414210A (en) * | 1979-10-02 | 1983-11-08 | Rohm And Haas Company | 2-Hydroxyarylethyltriazole fungicides |
| CH647513A5 (de) * | 1979-11-13 | 1985-01-31 | Sandoz Ag | Triazol-derivate, deren herstellung und verwendung. |
| DE3042303A1 (de) * | 1979-11-13 | 1981-08-27 | Sandoz-Patent-GmbH, 7850 Lörrach | Organische verbindungen, deren herstellung und verwendung |
| US4366401A (en) * | 1979-12-01 | 1982-12-28 | Lucas Industries Limited | Electromagnetic devices |
| US4432989A (en) * | 1980-07-18 | 1984-02-21 | Sandoz, Inc. | αAryl-1H-imidazole-1-ethanols |
| ATE73293T1 (de) * | 1980-08-18 | 1992-03-15 | Ici Plc | Verwendung von triazolylaethanol-derivate und deren zusammensetzungen als nichtlandwirtschaftliche fungizide. |
| PH17522A (en) * | 1980-08-28 | 1984-09-13 | Ici Plc | Pharmaceutical compositions of fungicidal triazole derivatives |
| EP0052424B2 (en) * | 1980-11-19 | 1990-02-28 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| EP0117578A3 (en) * | 1983-02-23 | 1985-01-30 | Shionogi & Co., Ltd. | Azole-substituted alcohol derivatives |
| CH658654A5 (de) * | 1983-03-04 | 1986-11-28 | Sandoz Ag | Azolderivate, verfahren zu ihrer herstellung und mittel die diese verbindungen enthalten. |
| NL8402548A (nl) * | 1983-09-01 | 1985-04-01 | Sandoz Ag | Nieuwe azoolverbindingen. |
-
1983
- 1983-03-04 CH CH1196/83A patent/CH658654A5/de not_active IP Right Cessation
-
1984
- 1984-02-20 HU HU84655A patent/HU195907B/hu unknown
- 1984-02-20 NL NLAANVRAGE8400529,A patent/NL189564C/xx not_active IP Right Cessation
- 1984-02-27 US US06/584,161 patent/US4664696A/en not_active Expired - Lifetime
- 1984-02-27 DE DE19843406993 patent/DE3406993A1/de active Granted
- 1984-02-27 BE BE1/10967A patent/BE899008A/fr not_active IP Right Cessation
- 1984-02-27 FR FR8403095A patent/FR2542000B1/fr not_active Expired
- 1984-02-29 BR BR8400958A patent/BR8400958A/pt not_active IP Right Cessation
- 1984-02-29 GB GB08405226A patent/GB2136423B/en not_active Expired
- 1984-02-29 DK DK149684A patent/DK165407C/da not_active IP Right Cessation
- 1984-03-01 ES ES530203A patent/ES8506642A1/es not_active Expired
- 1984-03-01 FI FI840824A patent/FI81784C/fi not_active IP Right Cessation
- 1984-03-02 PT PT78192A patent/PT78192B/pt unknown
- 1984-03-02 AU AU25253/84A patent/AU571490B2/en not_active Expired
- 1984-03-02 CS CS841536A patent/CS251081B2/cs unknown
- 1984-03-02 CA CA000448704A patent/CA1232278A/en not_active Expired
- 1984-03-02 IT IT47791/84A patent/IT1199079B/it active
- 1984-03-02 AT AT0071684A patent/AT387219B/de not_active IP Right Cessation
- 1984-03-02 NZ NZ207359A patent/NZ207359A/xx unknown
- 1984-03-02 SU SU843707140A patent/SU1416058A3/ru active
- 1984-03-02 SE SE8401177A patent/SE456678B/sv not_active IP Right Cessation
- 1984-03-02 UA UA3707140A patent/UA7048A1/uk unknown
- 1984-03-02 IL IL71126A patent/IL71126A/xx not_active IP Right Cessation
- 1984-03-02 JP JP59041207A patent/JPH06756B2/ja not_active Expired - Lifetime
- 1984-03-02 LU LU85237A patent/LU85237A1/fr unknown
- 1984-03-02 IE IE508/84A patent/IE57003B1/en not_active IP Right Cessation
- 1984-03-02 PL PL1984246493A patent/PL139662B1/pl unknown
- 1984-03-02 ZA ZA841606A patent/ZA841606B/xx unknown
- 1984-03-02 PH PH30333A patent/PH22915A/en unknown
- 1984-03-02 TR TR1540/84A patent/TR22432A/xx unknown
- 1984-03-03 EG EG149/84A patent/EG16963A/xx active
- 1984-03-09 DZ DZ847095A patent/DZ613A1/fr active
- 1984-03-21 GR GR74167A patent/GR82344B/el unknown
-
1987
- 1987-03-20 US US07/028,453 patent/US4849439A/en not_active Expired - Lifetime
- 1987-12-30 MY MY767/87A patent/MY8700767A/xx unknown
-
1988
- 1988-09-15 KE KE3832A patent/KE3832A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU195907B (en) | Fungicidal composition comprising 1-triazolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivative as active ingredient and process for producing 1-azolyl-2-phenyl-3-cyclopropyl-propan-2-ol derivatives | |
| CS243477B2 (en) | Plants' fungi diseases subdueing agent method of efficient substances production | |
| FR2612741A1 (fr) | Alpha-aryl-alpha-phenylethyl-1h-1,2,4-triazole-1-propanenitriles, composition fongicide les contenant, procede pour combattre les champignons phytopathogenes avec de tels nitriles et procede de preparation de ces nitriles | |
| IE56024B1 (en) | Substituted 1-hydroxyethyl-triazolyl derivatives | |
| JPH0680517A (ja) | 殺菌性１，２，４−トリアゾール | |
| US4609668A (en) | Fungicidal α-(alkynylphenyl)azole ethanol compounds | |
| HU177167B (en) | Fungicide compositions and process for preparing 4-azolyl-4-phenoxy-butanoic acid derivatives as active substances thereof | |
| HU176919B (hu) | Fungicidnye preparaty soderzhahhie galogenozamehhjonnye proizvodnye 1-azolil-butana i sposob poluchenija aktivnykh vehhestv | |
| JPS623147B2 (OSRAM) | ||
| JPS6224425B2 (OSRAM) | ||
| JPH0463071B2 (OSRAM) | ||
| JPS6026111B2 (ja) | 新規な１−アゾリル−４−ヒドロキシ−ブタン誘導体，その製造方法およびそれを活性成分として含有する殺菌剤組成物 | |
| EP0100193B1 (en) | Triazole anti-fungal agents | |
| JPS5965088A (ja) | ２−アリ−ル−２−アゾリルメチル−１，３−ジオキセピン | |
| KR890003599B1 (ko) | 아졸 화합물의 제조방법 | |
| US4965277A (en) | Allylaminoethylazoles | |
| EP0319481B1 (en) | Azole compounds | |
| EP0113509A2 (en) | 1,3-Bis(triazolyl)-2-amino-2-aryl-propane derivatives and pharmaceutical fungicidal compositions containing them | |
| GB2142921A (en) | Triazole derivatives | |
| KR840000701B1 (ko) | 1-페닐-2-트리아졸일-에틸 유도체의 금속염 착화합물의 제조방법 | |
| JPS5965080A (ja) | 置換アゾリルエ−テル−ケトン類および−カルビノ−ル類、それらの製造法および殺菌剤としてのそれらの使用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: NOVARTIS AG (NOVARTIS SA, NOVARTIS INC.), CH |
|
| HPC4 | Succession in title of patentee |
Owner name: SYNGENTA PARTICIPATIONS AG, CH |