CH615569A5 - - Google Patents
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- Publication number
- CH615569A5 CH615569A5 CH173575A CH173575A CH615569A5 CH 615569 A5 CH615569 A5 CH 615569A5 CH 173575 A CH173575 A CH 173575A CH 173575 A CH173575 A CH 173575A CH 615569 A5 CH615569 A5 CH 615569A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- chloride
- acid
- active ingredient
- alkyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 24
- -1 Trityl halides Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 206010061217 Infestation Diseases 0.000 description 17
- 239000002904 solvent Substances 0.000 description 15
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
- 239000013543 active substance Substances 0.000 description 14
- 239000007921 spray Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- OZHQKHFCDZKWFC-UHFFFAOYSA-N [azido(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N=[N+]=[N-])C1=CC=CC=C1 OZHQKHFCDZKWFC-UHFFFAOYSA-N 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000251730 Chondrichthyes Species 0.000 description 4
- 206010017533 Fungal infection Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000896242 Podosphaera Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 208000024386 fungal infectious disease Diseases 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- GJSLXMFWNANRIA-UHFFFAOYSA-N 1-[azido(diphenyl)methyl]-2-chlorobenzene Chemical compound ClC1=CC=CC=C1C(N=[N+]=[N-])(C=1C=CC=CC=1)C1=CC=CC=C1 GJSLXMFWNANRIA-UHFFFAOYSA-N 0.000 description 3
- MFOLMJVKEKAVIV-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MFOLMJVKEKAVIV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 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
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 208000029561 pustule Diseases 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 2
- ZSVGIOJJUOHJCG-UHFFFAOYSA-N 1,2-dichloro-4-[chloro(diphenyl)methyl]benzene Chemical compound C1=C(Cl)C(Cl)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 ZSVGIOJJUOHJCG-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SKWWCKGHUDPXOZ-UHFFFAOYSA-N 1-(trichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)(Cl)Cl)=C1 SKWWCKGHUDPXOZ-UHFFFAOYSA-N 0.000 description 1
- MOZMGJFHFHARAB-UHFFFAOYSA-N 1-[azido(diphenyl)methyl]-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(N=[N+]=[N-])(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 MOZMGJFHFHARAB-UHFFFAOYSA-N 0.000 description 1
- JNJRULCXXGGTRN-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2,3-dimethylbenzene Chemical compound CC1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C JNJRULCXXGGTRN-UHFFFAOYSA-N 0.000 description 1
- GTRODSBTUFVLBP-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 GTRODSBTUFVLBP-UHFFFAOYSA-N 0.000 description 1
- WOVRDRPEWHQOGZ-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 WOVRDRPEWHQOGZ-UHFFFAOYSA-N 0.000 description 1
- BXDIQZMXXDWMSE-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-3-iodobenzene Chemical compound C=1C=CC=CC=1C(C=1C=C(I)C=CC=1)(Cl)C1=CC=CC=C1 BXDIQZMXXDWMSE-UHFFFAOYSA-N 0.000 description 1
- XURJOVWXWPQFBN-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-3-methylbenzene Chemical compound CC1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 XURJOVWXWPQFBN-UHFFFAOYSA-N 0.000 description 1
- LDJOPWBFPCHUPY-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LDJOPWBFPCHUPY-UHFFFAOYSA-N 0.000 description 1
- BOSHBPXJWFPGDJ-UHFFFAOYSA-N 1-[chloro(diphenyl)methyl]-4-(trifluoromethyl)benzene Chemical compound C1=CC(C(F)(F)F)=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 BOSHBPXJWFPGDJ-UHFFFAOYSA-N 0.000 description 1
- BUAJFEJSDOBJOE-UHFFFAOYSA-N 1-[chloro-(2-methylphenyl)-phenylmethyl]-2-methylbenzene Chemical compound CC1=CC=CC=C1C(Cl)(C=1C(=CC=CC=1)C)C1=CC=CC=C1 BUAJFEJSDOBJOE-UHFFFAOYSA-N 0.000 description 1
- QKOPYEDBKRYHMW-UHFFFAOYSA-N 1-[chloro-(4-methylphenyl)-phenylmethyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(Cl)(C=1C=CC(C)=CC=1)C1=CC=CC=C1 QKOPYEDBKRYHMW-UHFFFAOYSA-N 0.000 description 1
- JUIWWCQVVPXWNF-UHFFFAOYSA-N 1-bromo-3-[chloro(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=C(Br)C=CC=1)(Cl)C1=CC=CC=C1 JUIWWCQVVPXWNF-UHFFFAOYSA-N 0.000 description 1
- VRDBENSNKJSVBL-UHFFFAOYSA-N 1-chloro-2-[chloro-(2-chlorophenyl)-phenylmethyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C(=CC=CC=1)Cl)C1=CC=CC=C1 VRDBENSNKJSVBL-UHFFFAOYSA-N 0.000 description 1
- LHYWXKLRGQMXAW-UHFFFAOYSA-N 1-chloro-4-[chloro-(4-chlorophenyl)-phenylmethyl]benzene Chemical compound C1=CC(Cl)=CC=C1C(Cl)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 LHYWXKLRGQMXAW-UHFFFAOYSA-N 0.000 description 1
- UMOADUKJXDTOPX-UHFFFAOYSA-N 2-[chloro(diphenyl)methyl]-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 UMOADUKJXDTOPX-UHFFFAOYSA-N 0.000 description 1
- VZXHNYMLNDXSHK-UHFFFAOYSA-N 2-[chloro(diphenyl)methyl]-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(C(Cl)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 VZXHNYMLNDXSHK-UHFFFAOYSA-N 0.000 description 1
- DPCWGEYMPDGJGJ-UHFFFAOYSA-N 2-[chloro(diphenyl)methyl]benzonitrile Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)C#N)(Cl)C1=CC=CC=C1 DPCWGEYMPDGJGJ-UHFFFAOYSA-N 0.000 description 1
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-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
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241001480059 Erysiphaceae Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000287436 Turdus merula Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- AAYFQAPISKPSSI-UHFFFAOYSA-N [N].C#C Chemical compound [N].C#C AAYFQAPISKPSSI-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2407305A DE2407305C2 (de) | 1974-02-15 | 1974-02-15 | Triphenyl-1,2,3-triazol-1-yl-methane, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615569A5 true CH615569A5 (en, 2012) | 1980-02-15 |
Family
ID=5907525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH173575A CH615569A5 (en, 2012) | 1974-02-15 | 1975-02-13 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4098894A (en, 2012) |
| JP (1) | JPS5734804B2 (en, 2012) |
| BE (1) | BE825479A (en, 2012) |
| BR (1) | BR7500883A (en, 2012) |
| CH (1) | CH615569A5 (en, 2012) |
| DD (1) | DD118367A5 (en, 2012) |
| DE (1) | DE2407305C2 (en, 2012) |
| DK (1) | DK135694C (en, 2012) |
| FR (1) | FR2261274B1 (en, 2012) |
| GB (1) | GB1457986A (en, 2012) |
| IL (1) | IL46619A (en, 2012) |
| IT (1) | IT1046877B (en, 2012) |
| LU (1) | LU71839A1 (en, 2012) |
| NL (1) | NL7501659A (en, 2012) |
| SE (1) | SE7501615L (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225520A1 (de) * | 1981-07-17 | 1983-02-03 | Sandoz-Patent-GmbH, 7850 Lörrach | Triazole und ihre verwendung zur bekaempfung von schaedlingen |
| JPS5948203U (ja) * | 1982-09-23 | 1984-03-30 | 国際商事株式会社 | 運動ぐつ |
| US4845227A (en) * | 1984-06-18 | 1989-07-04 | Eli Lilly And Company | Aromatase inhibitors from azoles |
| US4801594A (en) * | 1984-06-18 | 1989-01-31 | Eli Lilly And Company | Aromatase inhibitors |
| TW210334B (en, 2012) * | 1990-12-12 | 1993-08-01 | Ciba Geigy Ag | |
| JPH06315403A (ja) * | 1993-04-28 | 1994-11-15 | Top Uin Japan Kk | 運動靴 |
| AU2003240482B2 (en) | 2002-05-30 | 2009-03-12 | The Scripps Research Institute | Copper-catalysed ligation of azides and acetylenes |
| US7060850B2 (en) * | 2002-07-11 | 2006-06-13 | Fluorous Technologies Incorporated | Fluorous tagging and scavenging reactants and methods of synthesis and use thereof |
| WO2015193915A1 (en) * | 2014-06-20 | 2015-12-23 | Council Of Scientific & Industrial Research | Novel 1,2,3 triazole antifungal agents and preparation thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1940626U (de) | 1965-04-13 | 1966-06-16 | Siemens Ag | Anordnung zur gleichrichtung von wechselstroemen hoher spannung und hoher frequenz. |
| DE1940628U (de) | 1965-11-10 | 1966-06-16 | Siemens Ag | Beauelement zum druckfreien aufnehmen von magnetischen kernen mit rechteckfoermiger hystereseschleife. |
| DE1940627U (de) | 1966-02-09 | 1966-06-16 | Fritz Hellige & Co G M B H Fab | Flache elektrode zur abnahme oder applikation elektrischer spannungen und stroeme ammenschlichen oder tierischen koerper. |
| DE1670976B2 (de) * | 1968-01-29 | 1976-07-22 | N-trityl-imidazole | |
| CH488713A (de) * | 1968-08-28 | 1970-04-15 | Bayer Ag | Verfahren zur Herstellung von 1-Trityl-1,2,4-triazolen |
| BE754506A (fr) * | 1969-08-09 | 1971-02-08 | Bayer Ag | Procede de fabrication de n-triphenylmethyl-limidazoles et de n-triphenylmethyltriazoles a l'aide d'organo-magnesiens |
-
1974
- 1974-02-15 DE DE2407305A patent/DE2407305C2/de not_active Expired
-
1975
- 1975-02-05 US US05/547,428 patent/US4098894A/en not_active Expired - Lifetime
- 1975-02-12 IL IL7546619A patent/IL46619A/xx unknown
- 1975-02-12 NL NL7501659A patent/NL7501659A/xx not_active Application Discontinuation
- 1975-02-13 DD DD184163A patent/DD118367A5/xx unknown
- 1975-02-13 BE BE153313A patent/BE825479A/xx not_active IP Right Cessation
- 1975-02-13 BR BR883/75A patent/BR7500883A/pt unknown
- 1975-02-13 LU LU71839A patent/LU71839A1/xx unknown
- 1975-02-13 CH CH173575A patent/CH615569A5/de not_active IP Right Cessation
- 1975-02-13 IT IT20249/75A patent/IT1046877B/it active
- 1975-02-13 SE SE7501615A patent/SE7501615L/xx not_active Application Discontinuation
- 1975-02-14 JP JP1810675A patent/JPS5734804B2/ja not_active Expired
- 1975-02-14 GB GB627975A patent/GB1457986A/en not_active Expired
- 1975-02-14 FR FR7504731A patent/FR2261274B1/fr not_active Expired
- 1975-02-14 DK DK56375A patent/DK135694C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| BR7500883A (pt) | 1975-12-02 |
| DE2407305C2 (de) | 1984-06-28 |
| IT1046877B (it) | 1980-07-31 |
| US4098894A (en) | 1978-07-04 |
| IL46619A0 (en) | 1975-04-25 |
| DK135694B (da) | 1977-06-13 |
| FR2261274B1 (en, 2012) | 1978-10-06 |
| GB1457986A (en) | 1976-12-08 |
| IL46619A (en) | 1978-12-17 |
| DK56375A (en, 2012) | 1975-10-13 |
| JPS5734804B2 (en, 2012) | 1982-07-26 |
| JPS50116645A (en, 2012) | 1975-09-12 |
| DD118367A5 (en, 2012) | 1976-03-05 |
| DE2407305A1 (de) | 1975-08-28 |
| LU71839A1 (en, 2012) | 1975-12-09 |
| BE825479A (fr) | 1975-08-13 |
| FR2261274A1 (en, 2012) | 1975-09-12 |
| DK135694C (da) | 1977-11-21 |
| SE7501615L (en, 2012) | 1975-08-18 |
| NL7501659A (nl) | 1975-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |