HU179670B - Fungicide compositions containing metal-salt-complexes of i-phenyl-2-triasoly-ethen derivatives and process for producing the active agents - Google Patents
Fungicide compositions containing metal-salt-complexes of i-phenyl-2-triasoly-ethen derivatives and process for producing the active agents Download PDFInfo
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- HU179670B HU179670B HU78BA3661A HUBA003661A HU179670B HU 179670 B HU179670 B HU 179670B HU 78BA3661 A HU78BA3661 A HU 78BA3661A HU BA003661 A HUBA003661 A HU BA003661A HU 179670 B HU179670 B HU 179670B
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- weight
- phenyl
- dichloro
- parts
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- 239000000203 mixture Substances 0.000 title claims description 40
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000013543 active substance Substances 0.000 title description 6
- 239000000417 fungicide Substances 0.000 title description 3
- -1 1-phenyl-2-triazolyl Chemical group 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000004480 active ingredient Substances 0.000 claims description 37
- 238000002360 preparation method Methods 0.000 claims description 19
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000003995 emulsifying agent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229920005610 lignin Polymers 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 239000011572 manganese Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 239000011435 rock Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
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- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
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- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
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- 125000005228 aryl sulfonate group Chemical group 0.000 claims 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 9
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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- 239000000843 powder Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 244000141359 Malus pumila Species 0.000 description 7
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- 235000015103 Malus silvestris Nutrition 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- WNLYOHQDXYUFCT-UHFFFAOYSA-N 1-phenyl-2-(2h-triazol-4-yl)ethanol Chemical compound C=1C=CC=CC=1C(O)CC1=CNN=N1 WNLYOHQDXYUFCT-UHFFFAOYSA-N 0.000 description 5
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DSXJKFCLGZTRDG-UHFFFAOYSA-N 4-(2-phenylethyl)-2h-triazole Chemical compound C=1NN=NC=1CCC1=CC=CC=C1 DSXJKFCLGZTRDG-UHFFFAOYSA-N 0.000 description 3
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- 150000001340 alkali metals Chemical class 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
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- 150000004820 halides Chemical class 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000011592 zinc chloride Substances 0.000 description 3
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- VPGSXIKVUASQIY-UHFFFAOYSA-N 1,2-dibutylnaphthalene Chemical compound C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 VPGSXIKVUASQIY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
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- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- KDNUQPMWSQFNHK-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl)octan-1-ol Chemical compound C1=NC=NN1C(CCCCCC)C(O)C1=CC=C(Cl)C=C1Cl KDNUQPMWSQFNHK-UHFFFAOYSA-N 0.000 description 1
- SCZJKCNKEACEKR-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)ethyl]-1,2,4-triazole Chemical compound ClC1=CC(Cl)=CC=C1CCN1N=CN=C1 SCZJKCNKEACEKR-UHFFFAOYSA-N 0.000 description 1
- KEWBUOMVBFMGNS-UHFFFAOYSA-N 2-(2-phenylethyl)-1,3-thiazole Chemical compound N=1C=CSC=1CCC1=CC=CC=C1 KEWBUOMVBFMGNS-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
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- TUKHJQOBZOIDOE-UHFFFAOYSA-L [Cu](Cl)Cl.ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)OC(C(C)(C)C)=O.ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)OC(C(C)(C)C)=O Chemical class [Cu](Cl)Cl.ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)OC(C(C)(C)C)=O.ClC1=C(C=CC(=C1)Cl)C(CN1N=CN=C1)OC(C(C)(C)C)=O TUKHJQOBZOIDOE-UHFFFAOYSA-L 0.000 description 1
- 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
- 230000000895 acaricidal effect Effects 0.000 description 1
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- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 125000005336 allyloxy group Chemical group 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000033354 avian tuberculosis Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000009172 bursting Effects 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 208000034653 disorder of pilosebaceous unit Diseases 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007952 growth promoter Substances 0.000 description 1
- 239000004009 herbicide Substances 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
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000019988 mead Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 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
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010802 sludge 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772725214 DE2725214A1 (de) | 1977-06-03 | 1977-06-03 | Metallsalzkomplexe von 1-phenyl-2- triazolyl-aethyl-derivaten, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU179670B true HU179670B (en) | 1982-11-29 |
Family
ID=6010698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU78BA3661A HU179670B (en) | 1977-06-03 | 1978-06-02 | Fungicide compositions containing metal-salt-complexes of i-phenyl-2-triasoly-ethen derivatives and process for producing the active agents |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4366152A (en, 2012) |
| EP (1) | EP0000018B1 (en, 2012) |
| JP (1) | JPS543069A (en, 2012) |
| AR (1) | AR226278A1 (en, 2012) |
| AT (1) | AT357374B (en, 2012) |
| AU (1) | AU516653B2 (en, 2012) |
| BR (1) | BR7803550A (en, 2012) |
| CA (1) | CA1106386A (en, 2012) |
| CS (1) | CS199530B2 (en, 2012) |
| DD (1) | DD137659A5 (en, 2012) |
| DE (2) | DE2725214A1 (en, 2012) |
| DK (1) | DK248778A (en, 2012) |
| EG (1) | EG13358A (en, 2012) |
| ES (1) | ES470459A1 (en, 2012) |
| HU (1) | HU179670B (en, 2012) |
| IL (1) | IL54841A0 (en, 2012) |
| IT (1) | IT1098307B (en, 2012) |
| NZ (1) | NZ187449A (en, 2012) |
| PL (1) | PL109268B1 (en, 2012) |
| PT (1) | PT68099A (en, 2012) |
| SU (1) | SU1001848A3 (en, 2012) |
| TR (1) | TR19767A (en, 2012) |
| ZA (1) | ZA783177B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833194A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Triazolderivate |
| CA1179678A (en) * | 1981-03-27 | 1984-12-18 | Elmar Sturm | Antimicrobial triazole derivatives |
| US5266585A (en) * | 1981-05-12 | 1993-11-30 | Ciba-Geigy Corporation | Arylphenyl ether derivatives, compositions containing these compounds and use thereof |
| GB2104065B (en) * | 1981-06-04 | 1985-11-06 | Ciba Geigy Ag | Heterocyclyl-substituted mandelic acid compounds and mandelonitriles and their use for combating microorganisms |
| DE3208194A1 (de) * | 1982-03-06 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | Substituierte azolylethyl-oximinoalkyl-ether, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| US4533659A (en) * | 1982-06-09 | 1985-08-06 | Ciba-Geigy Corporation | Microbicidal 2-(1H-1,2,4-triazolylmethyl-1'-yl)-2-siloxy-2-phenyl-acetates |
| US4517194A (en) * | 1982-06-25 | 1985-05-14 | Ciba-Geigy Corporation | Azolylmandelic acid derivatives and use thereof for controlling microorganisms |
| US4584008A (en) * | 1982-07-14 | 1986-04-22 | Chevron Research Company | Aldol adducts containing triazole groups |
| DE3484968D1 (de) * | 1983-05-19 | 1991-10-02 | Ciba Geigy Ag | Verfahren zur herstellung von 1-triazolylethylether-derivaten, sowie mikrobizide mittel enthaltende neue 1-triazolyl-phenoxyphenylethylether-derivate als wirkstoffe und deren verwendung. |
| US4870094A (en) * | 1984-05-02 | 1989-09-26 | Uniroyal Chemical Company, Inc. | Substituted imidazoles and triazoles |
| US5039332A (en) * | 1985-09-19 | 1991-08-13 | Uniroyal Chemical Company, Inc. | Substituted oxathiolanes |
| EP0275955B1 (de) * | 1987-01-21 | 1990-07-04 | Ciba-Geigy Ag | Mikrobizides Mittel |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2423987C2 (de) * | 1974-05-17 | 1986-01-16 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2502932C2 (de) * | 1975-01-24 | 1985-04-18 | Bayer Ag, 5090 Leverkusen | Metallkomplexe von N-Trityl-azolen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
| DE2547953A1 (de) * | 1975-10-27 | 1977-04-28 | Bayer Ag | (1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
-
1977
- 1977-06-03 DE DE19772725214 patent/DE2725214A1/de not_active Withdrawn
-
1978
- 1978-05-22 DD DD78205506A patent/DD137659A5/xx unknown
- 1978-05-25 US US05/909,602 patent/US4366152A/en not_active Expired - Lifetime
- 1978-05-29 PT PT68099A patent/PT68099A/pt unknown
- 1978-05-30 TR TR19767A patent/TR19767A/xx unknown
- 1978-05-30 CS CS783505A patent/CS199530B2/cs unknown
- 1978-05-31 AR AR272409A patent/AR226278A1/es active
- 1978-06-01 NZ NZ187449A patent/NZ187449A/xx unknown
- 1978-06-01 EP EP78100030A patent/EP0000018B1/de not_active Expired
- 1978-06-01 JP JP6499778A patent/JPS543069A/ja active Granted
- 1978-06-01 SU SU782619251A patent/SU1001848A3/ru active
- 1978-06-01 IL IL7854841A patent/IL54841A0/xx not_active IP Right Cessation
- 1978-06-01 DE DE7878100030T patent/DE2860395D1/de not_active Expired
- 1978-06-02 HU HU78BA3661A patent/HU179670B/hu unknown
- 1978-06-02 AT AT401778A patent/AT357374B/de not_active IP Right Cessation
- 1978-06-02 CA CA304,643A patent/CA1106386A/en not_active Expired
- 1978-06-02 ZA ZA00783177A patent/ZA783177B/xx unknown
- 1978-06-02 PL PL1978207335A patent/PL109268B1/pl unknown
- 1978-06-02 DK DK248778A patent/DK248778A/da not_active Application Discontinuation
- 1978-06-02 BR BR787803550A patent/BR7803550A/pt not_active IP Right Cessation
- 1978-06-02 ES ES470459A patent/ES470459A1/es not_active Expired
- 1978-06-02 IT IT24172/78A patent/IT1098307B/it active
- 1978-06-03 EG EG351/78A patent/EG13358A/xx active
- 1978-06-06 AU AU36850/78A patent/AU516653B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA783177B (en) | 1979-06-27 |
| PL109268B1 (en) | 1980-05-31 |
| CS199530B2 (en) | 1980-07-31 |
| EP0000018B1 (de) | 1981-01-07 |
| ES470459A1 (es) | 1979-01-01 |
| US4366152A (en) | 1982-12-28 |
| EG13358A (en) | 1982-03-31 |
| AT357374B (de) | 1980-07-10 |
| JPS6337788B2 (en, 2012) | 1988-07-27 |
| DD137659A5 (de) | 1979-09-19 |
| JPS543069A (en) | 1979-01-11 |
| DE2725214A1 (de) | 1978-12-14 |
| CA1106386A (en) | 1981-08-04 |
| AU516653B2 (en) | 1981-06-18 |
| AR226278A1 (es) | 1982-06-30 |
| PL207335A1 (pl) | 1979-02-26 |
| AU3685078A (en) | 1979-12-13 |
| DK248778A (da) | 1978-12-04 |
| ATA401778A (de) | 1979-11-15 |
| BR7803550A (pt) | 1979-02-20 |
| NZ187449A (en) | 1979-11-01 |
| DE2860395D1 (en) | 1981-02-26 |
| PT68099A (en) | 1978-06-01 |
| IT7824172A0 (it) | 1978-06-02 |
| TR19767A (tr) | 1979-11-30 |
| SU1001848A3 (ru) | 1983-02-28 |
| EP0000018A1 (de) | 1978-12-20 |
| IT1098307B (it) | 1985-09-07 |
| IL54841A0 (en) | 1978-08-31 |
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