DE2547954C2 - - Google Patents
Info
- Publication number
- DE2547954C2 DE2547954C2 DE2547954A DE2547954A DE2547954C2 DE 2547954 C2 DE2547954 C2 DE 2547954C2 DE 2547954 A DE2547954 A DE 2547954A DE 2547954 A DE2547954 A DE 2547954A DE 2547954 C2 DE2547954 C2 DE 2547954C2
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- weight
- parts
- plants
- triazole
- 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
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Chemical group 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000417 fungicide Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- ARMYUHZPZQYHRI-UHFFFAOYSA-N 1-phenyl-2-(triazol-1-yl)ethanol Chemical class C=1C=CC=CC=1C(O)CN1C=CN=N1 ARMYUHZPZQYHRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 30
- 239000004480 active ingredient Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 206010061217 Infestation Diseases 0.000 description 22
- -1 β- chloro-phenyl-ethyl Chemical group 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 230000001681 protective effect Effects 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000007921 spray Substances 0.000 description 14
- 239000003995 emulsifying agent Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 241000220225 Malus Species 0.000 description 9
- 241000209219 Hordeum Species 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 8
- 239000010695 polyglycol Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 241000221785 Erysiphales Species 0.000 description 7
- 241000221787 Erysiphe Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241001480061 Blumeria graminis Species 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 206010037888 Rash pustular Diseases 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 208000029561 pustule Diseases 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 235000009849 Cucumis sativus Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000221577 Uromyces appendiculatus Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000017066 negative regulation of growth Effects 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- HGIUZBUHGQDZST-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(O)CN1C=NC=N1 HGIUZBUHGQDZST-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
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000489964 Fusicladium Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 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
- 229920003171 Poly (ethylene oxide) Polymers 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
- 241000209140 Triticum Species 0.000 description 2
- 241000221576 Uromyces Species 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 208000024386 fungal infectious disease Diseases 0.000 description 2
- 230000002464 fungitoxic effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000005283 haloketone group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-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
- 239000000843 powder Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OJWZLRXDUVBSTQ-UHFFFAOYSA-N 1-[2-chloro-2-[4-(4-chlorophenyl)phenyl]ethyl]-1,2,4-triazole Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(Cl)CN1C=NC=N1 OJWZLRXDUVBSTQ-UHFFFAOYSA-N 0.000 description 1
- BKLMMOVEZCBWFL-UHFFFAOYSA-N 1-[4-(2,4-dichlorophenyl)phenyl]-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(C=2C(=CC(Cl)=CC=2)Cl)C=CC=1C(O)CN1C=NC=N1 BKLMMOVEZCBWFL-UHFFFAOYSA-N 0.000 description 1
- ALNWCYLRUYXLCD-UHFFFAOYSA-N 1-ethyltriazole Chemical class CCN1C=CN=N1 ALNWCYLRUYXLCD-UHFFFAOYSA-N 0.000 description 1
- OUDWJLTZCWFWJV-UHFFFAOYSA-N 1-phenyl-2-(1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=CC=CC=1C(O)CN1C=NC=N1 OUDWJLTZCWFWJV-UHFFFAOYSA-N 0.000 description 1
- NYYSPVRERVXMLJ-UHFFFAOYSA-N 4,4-difluorocyclohexan-1-one Chemical compound FC1(F)CCC(=O)CC1 NYYSPVRERVXMLJ-UHFFFAOYSA-N 0.000 description 1
- 241000235349 Ascomycota Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 241000287436 Turdus merula Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 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
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000007796 conventional method Methods 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
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000004088 foaming agent 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
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 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
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 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
- 238000001665 trituration Methods 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
-
- 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 (33)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19752547954 DE2547954A1 (de) | 1975-10-27 | 1975-10-27 | 1-(2-halogen-2-phenyl-aethyl)-triazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
RO7687934A RO70233A (ro) | 1975-10-27 | 1976-10-06 | Procedeu de preparare a compusilor 1-(halogen-2-fenil-etil-5-triazoli |
US05/729,930 US4102891A (en) | 1975-10-27 | 1976-10-06 | 1-(2-Halogeno-2-phenyl-ethyl)-triazoles |
NO763440A NO763440L (en, 2012) | 1975-10-27 | 1976-10-08 | |
PT65749A PT65749B (de) | 1975-10-27 | 1976-10-22 | Verfahren zur herstellung von 1-(2-halogen-2-phenyl-athyl)-triazole und ihre verwendung als fungizide |
CH1342376A CH623575A5 (en, 2012) | 1975-10-27 | 1976-10-22 | |
IT28652/76A IT1068899B (it) | 1975-10-27 | 1976-10-25 | 1-(2-alogeno-2-fenil-etil)-triazoli,processo per la loro produzione e loro impiego quali fungicidi |
AT791876A AT350842B (de) | 1975-10-27 | 1976-10-25 | Fungizides mittel |
NLAANVRAGE7611807,A NL186906C (nl) | 1975-10-27 | 1976-10-25 | Werkwijze ter bereiding van 1-(2-halogeen-2-fenyl-ethyl)triazolen met fungitoxische werking, alsmede werkwijze ter bereiding van fungicide preparaten. |
GR52010A GR61270B (en) | 1975-10-27 | 1976-10-25 | Preparation process of 1-(2-halogen-2-phenyl-ethyl)-triazole and use thereof as fungicide |
DD7600195442A DD128372A5 (de) | 1975-10-27 | 1976-10-25 | Fungizide mittel |
FI763028A FI763028A7 (en, 2012) | 1975-10-27 | 1976-10-25 | |
IL7650758A IL50758A (en) | 1975-10-27 | 1976-10-25 | 1-(2halogeno-2-phenyl-ethyl)-triazoles,their preparation and fungicidal composition containg them |
LU76064A LU76064A1 (en, 2012) | 1975-10-27 | 1976-10-25 | |
EG649/76A EG12479A (en) | 1975-10-27 | 1976-10-25 | 1-(2-halogeno-2-phenyl-ethyl)-triazoles and their use as fungicides |
PL1976193255A PL100897B1 (pl) | 1975-10-27 | 1976-10-25 | Srodek grzybobojczy |
SU762414026A SU656463A3 (ru) | 1975-10-27 | 1976-10-25 | Фунгицидное средство |
CA264,230A CA1072104A (en) | 1975-10-27 | 1976-10-26 | 1-(2-halogeno-2-phenyl-ethyl)-triazoles and their use as fungicides |
ES452727A ES452727A1 (es) | 1975-10-27 | 1976-10-26 | Procedimiento para preparar 1-(2-halogeno-2-fenil-etil)- -triazoles. |
SE7611880A SE7611880L (sv) | 1975-10-27 | 1976-10-26 | ]-(2-halogen-2-fenyl-etyl)-triazoler, sett for deras framstellning och deras anvendning som fungicider |
GB44418/76A GB1510266A (en) | 1975-10-27 | 1976-10-26 | 1-(2-halogeno-2-phenyl-ethyl)-triazoles and their use as fungicides |
DK482276A DK482276A (da) | 1975-10-27 | 1976-10-26 | 1-(2-halogen-2-phenylethyl)-triazoler, fremgangsmade til deres fremstilling og deres anvendelse som fungicider |
BR7607151A BR7607151A (pt) | 1975-10-27 | 1976-10-26 | Processo para obtencao de 1-(2-halogeno-2-fenil-etil)-triazois,e composicoes fungicidas a base destes |
IE2357/76A IE43969B1 (en) | 1975-10-27 | 1976-10-26 | 1-2(-halogeno-2-phenyl-ethyl)-triazoles and their use as fungicides |
ZA766396A ZA766396B (en) | 1975-10-27 | 1976-10-26 | 1-(2-halogeno-2-phenyl-ethyl)-triazoles and their use as fungicides |
NZ182414A NZ182414A (en) | 1975-10-27 | 1976-10-26 | 1-(2-halo-2-phenylethyl)-1,2,4-triazoles and fungicidal compositions |
AU19051/76A AU501293B2 (en) | 1975-10-27 | 1976-10-27 | 1-(2-haloceni-2-phenyl-ethyl) triazoles |
CS766922A CS188294B2 (en) | 1975-10-27 | 1976-10-27 | Fungicide agent and method of preparation of active substances |
AR265243A AR217633A1 (es) | 1975-10-27 | 1976-10-27 | Nuevos compuestos quimicos industriales de propiedades fungicidas constituidos por 1-(2-halogeno-2-fenil-etil)-triazoles,composiciones fungicidas a base de los mismos y procedimiento para la produccion de dichos compuestos |
HU76BA3472A HU176746B (en) | 1975-10-27 | 1976-10-27 | Fungicide compositions comtaining 1-bracket-2-halogeno-2-phenyl-ethyl-bracket closed-triasole derivatives as active agents and process for producing the active agents |
TR18891A TR18891A (tr) | 1975-10-27 | 1976-10-27 | 1-(2-halojeno-2-fenil-etil)-triazoller,bunlarin hazirlanisina ait usul ve bunlarin fungisidler olarak kullanilmalar |
BE171818A BE847670A (fr) | 1975-10-27 | 1976-10-27 | Nouveaux 1-(2-halogeno-2-phenylethyl)-triazoles, leur procede de preparation et leur application comme fongicides |
FR7632432A FR2329660A1 (fr) | 1975-10-27 | 1976-10-27 | Nouveaux 1-(2-halogeno-2-phenylethyl)-triazoles, leur procede de preparation et leur application comme fongicides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19752547954 DE2547954A1 (de) | 1975-10-27 | 1975-10-27 | 1-(2-halogen-2-phenyl-aethyl)-triazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2547954A1 DE2547954A1 (de) | 1977-04-28 |
DE2547954C2 true DE2547954C2 (en, 2012) | 1989-02-16 |
Family
ID=5960150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752547954 Granted DE2547954A1 (de) | 1975-10-27 | 1975-10-27 | 1-(2-halogen-2-phenyl-aethyl)-triazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
Country Status (32)
Country | Link |
---|---|
US (1) | US4102891A (en, 2012) |
AR (1) | AR217633A1 (en, 2012) |
AT (1) | AT350842B (en, 2012) |
AU (1) | AU501293B2 (en, 2012) |
BE (1) | BE847670A (en, 2012) |
BR (1) | BR7607151A (en, 2012) |
CA (1) | CA1072104A (en, 2012) |
CH (1) | CH623575A5 (en, 2012) |
CS (1) | CS188294B2 (en, 2012) |
DD (1) | DD128372A5 (en, 2012) |
DE (1) | DE2547954A1 (en, 2012) |
DK (1) | DK482276A (en, 2012) |
EG (1) | EG12479A (en, 2012) |
ES (1) | ES452727A1 (en, 2012) |
FI (1) | FI763028A7 (en, 2012) |
FR (1) | FR2329660A1 (en, 2012) |
GB (1) | GB1510266A (en, 2012) |
GR (1) | GR61270B (en, 2012) |
HU (1) | HU176746B (en, 2012) |
IE (1) | IE43969B1 (en, 2012) |
IL (1) | IL50758A (en, 2012) |
IT (1) | IT1068899B (en, 2012) |
LU (1) | LU76064A1 (en, 2012) |
NL (1) | NL186906C (en, 2012) |
NO (1) | NO763440L (en, 2012) |
NZ (1) | NZ182414A (en, 2012) |
PL (1) | PL100897B1 (en, 2012) |
PT (1) | PT65749B (en, 2012) |
RO (1) | RO70233A (en, 2012) |
SE (1) | SE7611880L (en, 2012) |
TR (1) | TR18891A (en, 2012) |
ZA (1) | ZA766396B (en, 2012) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE44186B1 (en) * | 1975-12-03 | 1981-09-09 | Ici Ltd | 1,2,4-triazolyl alkanols and their use as pesticides |
DE2816817A1 (de) * | 1978-04-18 | 1979-10-31 | Bayer Ag | Oximino-triazolyl-aethane, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide |
DE2832234A1 (de) * | 1978-07-21 | 1980-01-31 | Bayer Ag | Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
DE2833193A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Insektizide mittel |
DE2833194A1 (de) * | 1978-07-28 | 1980-02-14 | Basf Ag | Triazolderivate |
US4414210A (en) * | 1979-10-02 | 1983-11-08 | Rohm And Haas Company | 2-Hydroxyarylethyltriazole fungicides |
DE3010093A1 (de) * | 1980-03-15 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | 1,1-diphenyl-2-(1.2.4-triazol-1-yl)-aethan-1-ole, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
US4479004A (en) * | 1980-11-03 | 1984-10-23 | Janssen Pharmaceutica N.V. | 1-[2-(4-Diphenyl)-1,3-dioxolan-2-yl-methyl]-1-H-triazoles |
EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
DE3923151A1 (de) * | 1989-07-13 | 1991-01-24 | Basf Ag | 1,2-dihalogenazolylethanderivate und diese enthaltende pflanzenschutzmittel |
DE4009594A1 (de) * | 1990-03-26 | 1991-10-02 | Basf Ag | Fungizide azolylethanderivate |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2009020C3 (de) * | 1970-02-26 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen |
DE2037610A1 (de) * | 1970-07-29 | 1972-02-03 | Bayer Ag | Neue alpha-substituierte Benzyl-azole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
US3679697A (en) * | 1970-10-08 | 1972-07-25 | Searle & Co | 1-({62 -halophenethyl)imidazoles |
DE2335020C3 (de) * | 1973-07-10 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | 1-(1,2,4-Triazol-1-yl)-2-phenoxy-4,4-dimethyl-pentan-3-on-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide |
DE2431407C2 (de) * | 1974-06-29 | 1982-12-02 | Bayer Ag, 5090 Leverkusen | 1,2,4-Triazol-1-yl-alkanone und -alkanole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide |
-
1975
- 1975-10-27 DE DE19752547954 patent/DE2547954A1/de active Granted
-
1976
- 1976-10-06 US US05/729,930 patent/US4102891A/en not_active Expired - Lifetime
- 1976-10-06 RO RO7687934A patent/RO70233A/ro unknown
- 1976-10-08 NO NO763440A patent/NO763440L/no unknown
- 1976-10-22 CH CH1342376A patent/CH623575A5/de not_active IP Right Cessation
- 1976-10-22 PT PT65749A patent/PT65749B/pt unknown
- 1976-10-25 GR GR52010A patent/GR61270B/el unknown
- 1976-10-25 LU LU76064A patent/LU76064A1/xx unknown
- 1976-10-25 AT AT791876A patent/AT350842B/de not_active IP Right Cessation
- 1976-10-25 IT IT28652/76A patent/IT1068899B/it active
- 1976-10-25 PL PL1976193255A patent/PL100897B1/pl unknown
- 1976-10-25 NL NLAANVRAGE7611807,A patent/NL186906C/xx not_active IP Right Cessation
- 1976-10-25 DD DD7600195442A patent/DD128372A5/xx unknown
- 1976-10-25 IL IL7650758A patent/IL50758A/xx unknown
- 1976-10-25 EG EG649/76A patent/EG12479A/xx active
- 1976-10-25 FI FI763028A patent/FI763028A7/fi not_active Application Discontinuation
- 1976-10-26 NZ NZ182414A patent/NZ182414A/xx unknown
- 1976-10-26 GB GB44418/76A patent/GB1510266A/en not_active Expired
- 1976-10-26 DK DK482276A patent/DK482276A/da unknown
- 1976-10-26 ES ES452727A patent/ES452727A1/es not_active Expired
- 1976-10-26 BR BR7607151A patent/BR7607151A/pt unknown
- 1976-10-26 CA CA264,230A patent/CA1072104A/en not_active Expired
- 1976-10-26 ZA ZA766396A patent/ZA766396B/xx unknown
- 1976-10-26 IE IE2357/76A patent/IE43969B1/en unknown
- 1976-10-26 SE SE7611880A patent/SE7611880L/xx unknown
- 1976-10-27 AR AR265243A patent/AR217633A1/es active
- 1976-10-27 CS CS766922A patent/CS188294B2/cs unknown
- 1976-10-27 TR TR18891A patent/TR18891A/xx unknown
- 1976-10-27 HU HU76BA3472A patent/HU176746B/hu unknown
- 1976-10-27 FR FR7632432A patent/FR2329660A1/fr active Granted
- 1976-10-27 BE BE171818A patent/BE847670A/xx not_active IP Right Cessation
- 1976-10-27 AU AU19051/76A patent/AU501293B2/en not_active Expired
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Legal Events
Date | Code | Title | Description |
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OD | Request for examination | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition |