DE2350122C2 - 1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide - Google Patents
1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als FungizideInfo
- Publication number
- DE2350122C2 DE2350122C2 DE2350122A DE2350122A DE2350122C2 DE 2350122 C2 DE2350122 C2 DE 2350122C2 DE 2350122 A DE2350122 A DE 2350122A DE 2350122 A DE2350122 A DE 2350122A DE 2350122 C2 DE2350122 C2 DE 2350122C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrogen
- meanings given
- general formula
- solvent
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 7
- -1 1-propyl-1,2,4-triazolyl Chemical class 0.000 title description 24
- 239000000417 fungicide Substances 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002902 organometallic compounds Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- NYYSPVRERVXMLJ-UHFFFAOYSA-N 4,4-difluorocyclohexan-1-one Chemical compound FC1(F)CCC(=O)CC1 NYYSPVRERVXMLJ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- SRZBHUBTUHPBDP-UHFFFAOYSA-N 4-ethyl-2h-triazole Chemical class CCC=1C=NNN=1 SRZBHUBTUHPBDP-UHFFFAOYSA-N 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 44
- 206010061217 Infestation Diseases 0.000 description 34
- 241000196324 Embryophyta Species 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000002877 alkyl aryl group Chemical group 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VLNUTKMHYLQCQB-UHFFFAOYSA-N 2,2-dimethylpentan-3-one Chemical compound CCC(=O)C(C)(C)C VLNUTKMHYLQCQB-UHFFFAOYSA-N 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 241000209219 Hordeum Species 0.000 description 3
- 241000896242 Podosphaera Species 0.000 description 3
- 206010037888 Rash pustular Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 235000013339 cereals Nutrition 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
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 208000024386 fungal infectious disease Diseases 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 208000029561 pustule Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- LUAREPUAXMHHLV-UHFFFAOYSA-N 1-chloro-2-(4-chloro-2-methylphenoxy)-4,4-dimethylpentan-3-one Chemical compound CC1=CC(Cl)=CC=C1OC(CCl)C(=O)C(C)(C)C LUAREPUAXMHHLV-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000969 carrier Substances 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
- 230000006378 damage Effects 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
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- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- HAGYXNVNFOULKK-UHFFFAOYSA-N 1-trityl-1,2,4-triazole Chemical compound N1=CN=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HAGYXNVNFOULKK-UHFFFAOYSA-N 0.000 description 1
- IFQYYZRQWOQQDT-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)-1-hydroxy-4,4-dimethylpentan-3-one Chemical compound CC1=CC(Cl)=CC=C1OC(CO)C(=O)C(C)(C)C IFQYYZRQWOQQDT-UHFFFAOYSA-N 0.000 description 1
- LRAVHNTWOPCEMF-UHFFFAOYSA-N 2-(4-chlorophenoxy)-3,4,4-trimethyl-1-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C=1C=C(Cl)C=CC=1OC(C(C)(O)C(C)(C)C)CN1C=NC=N1 LRAVHNTWOPCEMF-UHFFFAOYSA-N 0.000 description 1
- AWQRJARLPWUGTD-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4,4-dimethyl-1-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C=1C=C(Cl)C=CC=1OC(C(O)C(C)(C)C)CN1C=NC=N1 AWQRJARLPWUGTD-UHFFFAOYSA-N 0.000 description 1
- ZQZPGCKVJSFKAY-UHFFFAOYSA-N 2-(4-chlorophenoxy)-4,4-dimethyl-1-(1,2,4-triazol-1-yl)pentan-3-one Chemical compound C=1C=C(Cl)C=CC=1OC(C(=O)C(C)(C)C)CN1C=NC=N1 ZQZPGCKVJSFKAY-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 238000004821 distillation Methods 0.000 description 1
- 238000010410 dusting Methods 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
- 239000002024 ethyl acetate extract Substances 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000004313 glare Effects 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 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
- 239000000463 material Substances 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000010653 organometallic reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-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
- 244000052769 pathogen Species 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 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
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- QGDIJZMKEQCRBX-UHFFFAOYSA-N zinc;ethene Chemical group [Zn+2].[CH-]=C.[CH-]=C QGDIJZMKEQCRBX-UHFFFAOYSA-N 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2350122A DE2350122C2 (de) | 1973-10-05 | 1973-10-05 | 1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
| US05/509,881 US3972892A (en) | 1973-10-05 | 1974-09-27 | 1-[1,2,4-triazolyl-(1)]-2-aryloxy-3-hydroxy-alkanes |
| NL7412834A NL7412834A (nl) | 1973-10-05 | 1974-09-27 | 1-propyl 1.2.4-triazolylderivaten alsmede zou- aarvan, werkwijzen ter bereiding en toe- ng als fungiciden. |
| IT28027/74A IT1046666B (it) | 1973-10-05 | 1974-10-02 | I propil 1 2 4 triazolil derivati e loro sali processi per la loro produzione e loro impiego quali fungicidi |
| LU71041A LU71041A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-05 | 1974-10-03 | |
| CH1334574A CH588215A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-05 | 1974-10-03 | |
| IL7445770A IL45770A (en) | 1973-10-05 | 1974-10-03 | 1-(2-phenoxy-3-hydroxyalkyl)-1,2 4-triazoles and their salts their preparation and their use as fungicides |
| JP49114001A JPS5747884B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-05 | 1974-10-04 | |
| GB4310774A GB1437930A (en) | 1973-10-05 | 1974-10-04 | 1-propyl-1,2-4-triazolyl derivatives and their salts their prepa ration and their use as fungicides |
| BE149208A BE820702A (fr) | 1973-10-05 | 1974-10-04 | Nouveaux derives 1-propyl-1,2,4-triazolyliques et leurs sels, leur preparation et leur application comme fongicides |
| IE2056/74A IE40053B1 (en) | 1973-10-05 | 1974-10-04 | 1-propyl-1,2,4-triazolyl derivatives, and their salts, their preparation and their use as fungicides |
| BR8254/74A BR7408254D0 (pt) | 1973-10-05 | 1974-10-04 | Processo para a preparacao de derivados de 1-propil -1 2 4-triazolila e de seus sais e composicoes fungicidas a base destes |
| JP49114000A JPS5912669B2 (ja) | 1973-10-05 | 1974-10-04 | １−プロピル−１，２，４−トリアゾリル誘導体およびそれらの塩の製造法 |
| DK522574A DK139817C (da) | 1973-10-05 | 1974-10-04 | Fungicidt virksomme triazolyl-derivater og deres salte til anvendelse ved plantebeskyttelse og andre tekniske formaal |
| FR7433520A FR2246550B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-05 | 1974-10-04 | |
| JP58044589A JPS5941988B2 (ja) | 1973-10-05 | 1983-03-18 | １−プロピル−１，２，４−トリアゾリル誘導体およびそれらの塩の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2350122A DE2350122C2 (de) | 1973-10-05 | 1973-10-05 | 1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2350122A1 DE2350122A1 (de) | 1975-04-24 |
| DE2350122C2 true DE2350122C2 (de) | 1982-06-24 |
Family
ID=5894651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2350122A Expired DE2350122C2 (de) | 1973-10-05 | 1973-10-05 | 1-Propyl-1,2,4-triazolyl-Derivate und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
Country Status (14)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079142A (en) * | 1973-10-05 | 1978-03-14 | Bayer Aktiengesellschaft | 1-Propyl-triazolyl antimycotic compositions and methods of treating mycoses |
| US4156001A (en) * | 1975-11-26 | 1979-05-22 | Bayer Aktiengesellschaft | Synergistic fungicidal compositions containing 1,2,4-trizole derivatives and 2,4-dichloro-6-(o-chloroanilino)-1,3,5-triazine |
| DE2560512C2 (de) * | 1975-11-26 | 1984-11-15 | Bayer Ag, 5090 Leverkusen | Fungizides mittel |
| NZ184268A (en) * | 1976-06-08 | 1979-03-16 | Ici Ltd | 1,2,4-triazd-1-yl-alkone-diones derivatives and fungicidal and plant growth regulating compositions |
| DE2652313A1 (de) * | 1976-11-17 | 1978-05-18 | Basf Ag | Triazolderivate |
| DE2743767A1 (de) * | 1977-09-29 | 1979-04-12 | Bayer Ag | Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| EP0005600A1 (en) * | 1978-05-11 | 1979-11-28 | Imperial Chemical Industries Plc | Imidazolyl and triazolyl compounds, compositions containing them and methods of using them as plant fungicidal and growth regulating agents |
| DE2846980A1 (de) * | 1978-10-28 | 1980-05-08 | Bayer Ag | 1-ethen-azol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| DE2928967A1 (de) * | 1979-07-18 | 1981-02-12 | Bayer Ag | Azolyl-alkenole, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
| DE2928968A1 (de) * | 1979-07-18 | 1981-02-12 | Bayer Ag | Antimikrobielle mittel |
| GR78218B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-07-02 | 1984-09-26 | Ciba Geigy Ag | |
| DE3275088D1 (en) * | 1981-08-19 | 1987-02-19 | Ici Plc | Triazole derivatives, processes for preparing them, compositions containing them and processes for combating fungi and regulating plant growth |
| GB8301678D0 (en) * | 1983-01-21 | 1983-02-23 | Ici Plc | Heterocyclic compounds |
| JPS6019179U (ja) * | 1983-07-19 | 1985-02-08 | ティーディーケイ株式会社 | 凍結防止ヒ−タ |
| IL75017A (en) * | 1984-05-04 | 1989-07-31 | Basf Ag | Diastereoselective reduction of alpha-triazolylketones to beta-triazolylcarbinols |
| JPS63156946U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1987-03-31 | 1988-10-14 | ||
| KR102571394B1 (ko) * | 2020-10-14 | 2023-08-25 | 주식회사 케이티앤지 | 흡연재료의 가향숙성방법 및 이를 이용하여 제조된 흡연물품 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
-
1973
- 1973-10-05 DE DE2350122A patent/DE2350122C2/de not_active Expired
-
1974
- 1974-09-27 US US05/509,881 patent/US3972892A/en not_active Expired - Lifetime
- 1974-09-27 NL NL7412834A patent/NL7412834A/xx not_active Application Discontinuation
- 1974-10-02 IT IT28027/74A patent/IT1046666B/it active
- 1974-10-03 CH CH1334574A patent/CH588215A5/xx not_active IP Right Cessation
- 1974-10-03 LU LU71041A patent/LU71041A1/xx unknown
- 1974-10-03 IL IL7445770A patent/IL45770A/en unknown
- 1974-10-04 JP JP49114001A patent/JPS5747884B2/ja not_active Expired
- 1974-10-04 JP JP49114000A patent/JPS5912669B2/ja not_active Expired
- 1974-10-04 IE IE2056/74A patent/IE40053B1/xx unknown
- 1974-10-04 BR BR8254/74A patent/BR7408254D0/pt unknown
- 1974-10-04 FR FR7433520A patent/FR2246550B1/fr not_active Expired
- 1974-10-04 DK DK522574A patent/DK139817C/da not_active IP Right Cessation
- 1974-10-04 BE BE149208A patent/BE820702A/xx not_active IP Right Cessation
- 1974-10-04 GB GB4310774A patent/GB1437930A/en not_active Expired
-
1983
- 1983-03-18 JP JP58044589A patent/JPS5941988B2/ja not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |