DE2725314A1 - 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide - Google Patents
1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizideInfo
- Publication number
- DE2725314A1 DE2725314A1 DE19772725314 DE2725314A DE2725314A1 DE 2725314 A1 DE2725314 A1 DE 2725314A1 DE 19772725314 DE19772725314 DE 19772725314 DE 2725314 A DE2725314 A DE 2725314A DE 2725314 A1 DE2725314 A1 DE 2725314A1
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- alkyl
- stands
- formula
- triazolium
- 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- Withdrawn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 11
- 239000000417 fungicide Substances 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 triazolium halides Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 6
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- GCDVQIPVANUWJO-UHFFFAOYSA-O 1-(2-phenylethyl)-1H-triazol-1-ium Chemical class C1(=CC=CC=C1)CC[NH+]1N=NC=C1 GCDVQIPVANUWJO-UHFFFAOYSA-O 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000460 chlorine Substances 0.000 description 77
- 239000004480 active ingredient Substances 0.000 description 42
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- 230000008018 melting Effects 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 11
- 241000220225 Malus Species 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- 241000221785 Erysiphales Species 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- 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 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000005554 pickling Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000209219 Hordeum Species 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- OBLLZPQPZHJHPR-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 OBLLZPQPZHJHPR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241001480061 Blumeria graminis Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000896242 Podosphaera Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XMCRWEBERCXJCH-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1Cl XMCRWEBERCXJCH-UHFFFAOYSA-N 0.000 description 2
- HKMHSWAVMUFIPA-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C(=CC=CC=1Cl)Cl)CN1N=CN=C1 HKMHSWAVMUFIPA-UHFFFAOYSA-N 0.000 description 2
- WNLYOHQDXYUFCT-UHFFFAOYSA-N 1-phenyl-2-(2h-triazol-4-yl)ethanol Chemical class C=1C=CC=CC=1C(O)CC1=CNN=N1 WNLYOHQDXYUFCT-UHFFFAOYSA-N 0.000 description 2
- IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 206010037888 Rash pustular Diseases 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
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- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 238000002955 isolation Methods 0.000 description 2
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- 230000017066 negative regulation of growth Effects 0.000 description 2
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- XCWJBJOPHSVLGU-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=NC=N1 XCWJBJOPHSVLGU-UHFFFAOYSA-N 0.000 description 1
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- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
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- 239000005909 Kieselgur Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
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- 229940077388 benzenesulfonate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000008121 dextrose 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
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
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- 208000024386 fungal infectious disease Diseases 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007800 oxidant agent 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
- 244000052769 pathogen Species 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772725314 DE2725314A1 (de) | 1977-06-04 | 1977-06-04 | 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DD78205501A DD137658A5 (de) | 1977-06-04 | 1978-05-22 | Fungizide mittel |
| PT68100A PT68100A (de) | 1977-06-04 | 1978-05-29 | 1-(2-phenylathyl)-triazolium-salze verfahren zur ihrer herstellung sowie ihre verwendung als funcizide |
| CS783506A CS199531B2 (en) | 1977-06-04 | 1978-05-30 | Fungicide and process for preparing effective compounds |
| TR19791A TR19791A (tr) | 1977-06-04 | 1978-05-30 | 1-(2-feniletil)-triazolyum tuzlari,imallerine mahsus bir usul ve fungisidler olarak kullanilmalari |
| IL54840A IL54840A (en) | 1977-06-04 | 1978-06-01 | 1-(2-phenylethyl)-triazolium salts,their preparation and their use as fungicides |
| DE7878100029T DE2861233D1 (en) | 1977-06-04 | 1978-06-01 | 1-(2-phenylethyl)-triazolium salts, their preparation and their use as fungicides |
| EP78100029A EP0000017B1 (de) | 1977-06-04 | 1978-06-01 | 1-(2-Phenyläthyl)-triazolium-Salze, Verfahren zur ihrer Herstellung sowie ihre Verwendung als Fungizide |
| JP6499878A JPS543070A (en) | 1977-06-04 | 1978-06-01 | Novel 11*22phenylethyl** triazolium salt * production thereof and bactericide composition containing same as active ingredient |
| PL1978207336A PL109267B1 (en) | 1977-06-04 | 1978-06-02 | Fungicide |
| ES470458A ES470458A1 (es) | 1977-06-04 | 1978-06-02 | Procedimiento para la obtencion de sales de 1-(2-feniletil) triazolio de efecto fungicida |
| IT7824171A IT7824171A0 (it) | 1977-06-04 | 1978-06-02 | Funghicidi. sali di 1-(2-feniletil)-triazolio, processo per la loro produzione, nonche' loro impiego quali |
| CA304,664A CA1100976A (en) | 1977-06-04 | 1978-06-02 | 1-(2-phenylethyl)-triazolium salts and their use as fungicides |
| ZA00783176A ZA783176B (en) | 1977-06-04 | 1978-06-02 | 1-(2-phenylethyl)-triazolium salts and their use as fungicides |
| DK248378A DK248378A (da) | 1977-06-04 | 1978-06-02 | 1-(2-phenylethyl)-triazolium-salte fremgangsmaade til fremstilling deraf samt disses anvendelse som fungcider |
| BR787803551A BR7803551A (pt) | 1977-06-04 | 1978-06-02 | Processo para a preparacao de sais de 1-(2-feniletil)-triazolio,composicao fungicida e sua aplicacao |
| AU36848/78A AU3684878A (en) | 1977-06-04 | 1978-06-06 | 1 (2-phenyl ethyl) - triazolium salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772725314 DE2725314A1 (de) | 1977-06-04 | 1977-06-04 | 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2725314A1 true DE2725314A1 (de) | 1978-12-14 |
Family
ID=6010741
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772725314 Withdrawn DE2725314A1 (de) | 1977-06-04 | 1977-06-04 | 1-(2-phenylaethyl)-triazolium-salze, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE7878100029T Expired DE2861233D1 (en) | 1977-06-04 | 1978-06-01 | 1-(2-phenylethyl)-triazolium salts, their preparation and their use as fungicides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE7878100029T Expired DE2861233D1 (en) | 1977-06-04 | 1978-06-01 | 1-(2-phenylethyl)-triazolium salts, their preparation and their use as fungicides |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0000017B1 (cs) |
| JP (1) | JPS543070A (cs) |
| AU (1) | AU3684878A (cs) |
| BR (1) | BR7803551A (cs) |
| CA (1) | CA1100976A (cs) |
| CS (1) | CS199531B2 (cs) |
| DD (1) | DD137658A5 (cs) |
| DE (2) | DE2725314A1 (cs) |
| DK (1) | DK248378A (cs) |
| ES (1) | ES470458A1 (cs) |
| IL (1) | IL54840A (cs) |
| IT (1) | IT7824171A0 (cs) |
| PL (1) | PL109267B1 (cs) |
| PT (1) | PT68100A (cs) |
| TR (1) | TR19791A (cs) |
| ZA (1) | ZA783176B (cs) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6224254Y2 (cs) * | 1979-09-17 | 1987-06-20 | ||
| DE2937595A1 (de) * | 1979-09-18 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-azolyl-1-phenoxy-alkan-2-onen |
| CA1179678A (en) * | 1981-03-27 | 1984-12-18 | Elmar Sturm | Antimicrobial triazole derivatives |
| ATE66676T1 (de) * | 1983-05-19 | 1991-09-15 | Ciba Geigy Ag | Verfahren zur herstellung von 1triazolylethylether-derivaten, sowie mikrobizide mittel enthaltende neue 1-triazolyl- phenoxyphenylethylether-derivate als wirkstoffe und deren verwendung. |
| DE3319845A1 (de) * | 1983-06-01 | 1984-12-06 | Basf Ag, 6700 Ludwigshafen | Arylalkylimidazolium- und -triazoliumsalze, verfahren zu ihrer herstellung und ihre verwendung als mikrozide |
| IT1200422B (it) * | 1985-03-19 | 1989-01-18 | Ripari Gero Ist Farm Biolog | Composto con attivita' antimicrobia,sua preparazione e composizioni farmaceutiche che lo contengono |
| ES2016660B3 (es) * | 1987-01-21 | 1990-11-16 | Ciba-Geigy Ag | Agente microbicida. |
| SK45795A3 (en) * | 1992-10-09 | 1995-10-11 | Uniroyal Chemical Ltd | Substituted azole derivatives as fungicidal effective matters, method of preparing of these compounds, intermediates of this method, fungicidal agent containing these derivatives and controlling method of phytogene molds |
| MX356322B (es) | 2011-07-13 | 2018-05-23 | Basf Se | Compuestos sustituidos fungicidas de 2-[2-halogenalquil-4-(fenoxi) -fenil]-1-[1,2,4]triaxol-1-il-etanol. |
| EA201400137A1 (ru) | 2011-07-15 | 2014-06-30 | Басф Се | Фунгицидные алкилзамещенные 2-[2-хлоро-4-(4-хлорофенокси)фенил]-1-[1,2,4]триазол-1-ил-этанольные соединения |
| EP2731934A1 (en) | 2011-07-15 | 2014-05-21 | Basf Se | Fungicidal alkyl- and aryl-substituted 2-[2-chloro-4-(dihalo-phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds |
| MX2014001669A (es) | 2011-08-15 | 2014-05-27 | Basf Se | Compuestos de fungicidas de 1-{2-[2-halo-4-(4-halogen-fenoxi)-feni l]-2-alcoxi-2-alquinil/alquenil-etil}-1h-[1,2,4]triazol sustituidos. |
| CN103717577B (zh) | 2011-08-15 | 2016-06-15 | 巴斯夫欧洲公司 | 杀真菌的取代的1-{2-环基氧基-2-[2-卤代-4-(4-卤代苯氧基)苯基]乙基}-1h-[1,2,4]三唑化合物 |
| WO2013024077A1 (en) | 2011-08-15 | 2013-02-21 | Basf Se | Fungicidal substituted 1-{2-[2-halo-4-(4-halogen-phenoxy)-phenyl]-2-alkoxy-3-methyl-butyl}-1h-[1,2,4]triazole compounds |
| JP2014524430A (ja) | 2011-08-15 | 2014-09-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 殺菌性置換１−｛２−［２−ハロ−４−（４−ハロゲン−フェノキシ）−フェニル］−２−エトキシ−エチル｝−１ｈ−［１，２，４］トリアゾール化合物 |
| CN105050406B (zh) | 2012-12-20 | 2017-09-15 | 巴斯夫农业公司 | 包含三唑化合物的组合物 |
| EP2943476B1 (en) | 2013-01-09 | 2019-05-15 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| CN106028817A (zh) | 2013-07-08 | 2016-10-12 | 巴斯夫农业公司 | 包含三唑化合物和生物农药的组合物 |
| US10212934B2 (en) | 2014-06-25 | 2019-02-26 | BASF Agro B.V. | Pesticidal compositions |
| EP3214937B1 (en) | 2014-11-07 | 2024-07-03 | Basf Se | Pesticidal mixtures |
| EP3337452B1 (en) | 2015-08-20 | 2024-03-27 | Unilever IP Holdings B.V. | Encapsulated lactams |
| US11425909B2 (en) | 2016-03-16 | 2022-08-30 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on fruits |
| BR112018068705B1 (pt) | 2016-03-16 | 2022-09-06 | Basf Se | Método para controlar fungos fitopatogênicos |
| US10905122B2 (en) | 2016-03-16 | 2021-02-02 | Basf Se | Use of tetrazolinones for combating resistant phytopathogenic fungi on cereals |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ181916A (en) * | 1975-09-10 | 1979-01-11 | Ici Ltd | 1-substituted-1,2,4-triazoles and fungicidal compositions |
-
1977
- 1977-06-04 DE DE19772725314 patent/DE2725314A1/de not_active Withdrawn
-
1978
- 1978-05-22 DD DD78205501A patent/DD137658A5/xx unknown
- 1978-05-29 PT PT68100A patent/PT68100A/pt unknown
- 1978-05-30 TR TR19791A patent/TR19791A/xx unknown
- 1978-05-30 CS CS783506A patent/CS199531B2/cs unknown
- 1978-06-01 JP JP6499878A patent/JPS543070A/ja active Pending
- 1978-06-01 EP EP78100029A patent/EP0000017B1/de not_active Expired
- 1978-06-01 DE DE7878100029T patent/DE2861233D1/de not_active Expired
- 1978-06-01 IL IL54840A patent/IL54840A/xx unknown
- 1978-06-02 BR BR787803551A patent/BR7803551A/pt unknown
- 1978-06-02 PL PL1978207336A patent/PL109267B1/pl unknown
- 1978-06-02 ZA ZA00783176A patent/ZA783176B/xx unknown
- 1978-06-02 IT IT7824171A patent/IT7824171A0/it unknown
- 1978-06-02 DK DK248378A patent/DK248378A/da unknown
- 1978-06-02 CA CA304,664A patent/CA1100976A/en not_active Expired
- 1978-06-02 ES ES470458A patent/ES470458A1/es not_active Expired
- 1978-06-06 AU AU36848/78A patent/AU3684878A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| PL207336A1 (pl) | 1979-02-26 |
| DD137658A5 (de) | 1979-09-19 |
| CA1100976A (en) | 1981-05-12 |
| EP0000017A1 (de) | 1978-12-20 |
| PT68100A (de) | 1978-06-01 |
| DE2861233D1 (en) | 1981-12-10 |
| PL109267B1 (en) | 1980-05-31 |
| IL54840A0 (en) | 1978-08-31 |
| JPS543070A (en) | 1979-01-11 |
| ZA783176B (en) | 1979-06-27 |
| IL54840A (en) | 1982-03-31 |
| TR19791A (tr) | 1979-12-19 |
| AU3684878A (en) | 1979-12-13 |
| EP0000017B1 (de) | 1981-09-30 |
| IT7824171A0 (it) | 1978-06-02 |
| BR7803551A (pt) | 1979-02-20 |
| DK248378A (da) | 1978-12-05 |
| ES470458A1 (es) | 1979-01-01 |
| CS199531B2 (en) | 1980-07-31 |
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Legal Events
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| 8130 | Withdrawal |