DD283911A5 - Fungizide mittel - Google Patents

Fungizide mittel Download PDF

Info

Publication number: DD283911A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; alkyl; weight; parts; basf aktiengesellschaft
Prior art date: 1988-07-29

Application number

DD89331211A

Other languages

German (de)

English (en)

Inventor

Rainer Seele

Reiner Kober

Norbert Goetz

Eberhard Ammermann

Gisela Lorenz

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1988-07-29

Filing date

1989-07-27

Publication date

1990-10-31

1989-07-27 Application filed by ��@��k�� filed Critical ��@��k��

1990-10-31 Publication of DD283911A5 publication Critical patent/DD283911A5/de

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239000000417 fungicide Substances 0.000 title claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims abstract description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
239000004305 biphenyl Substances 0.000 claims abstract description 4
235000010290 biphenyl Nutrition 0.000 claims abstract description 4
125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
-1 nitro, Phenoxy, amino Chemical group 0.000 claims description 36
241000233866 Fungi Species 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
239000000463 material Substances 0.000 claims description 2
150000004696 coordination complex Chemical class 0.000 claims 2
230000002538 fungal effect Effects 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 32
229910052751 metal Chemical class 0.000 abstract description 4
239000002184 metal Chemical class 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 27
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 11
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000012074 organic phase Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
241000209140 Triticum Species 0.000 description 6
235000021307 Triticum Nutrition 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
230000000855 fungicidal effect Effects 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
150000003852 triazoles Chemical class 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
101100162703 Caenorhabditis elegans ani-1 gene Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
MTSHNPMLJVYGFR-LCYFTJDESA-N (e)-3-(2-chlorophenyl)-2-(4-fluorophenyl)prop-2-enal Chemical compound C1=CC(F)=CC=C1C(\C=O)=C/C1=CC=CC=C1Cl MTSHNPMLJVYGFR-LCYFTJDESA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
PRHYPTJXCWSQKU-UHFFFAOYSA-N 1-[[3-(4-chlorophenyl)-2-phenyloxiran-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(Cl)=CC=C1C1C(C=2C=CC=CC=2)(CN2N=CN=C2)O1 PRHYPTJXCWSQKU-UHFFFAOYSA-N 0.000 description 2
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
OEVGZRDJQXPUOU-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-1h-imidazole Chemical class N=1C=CNC=1CC1CO1 OEVGZRDJQXPUOU-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241001480061 Blumeria graminis Species 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000221785 Erysiphales Species 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
244000070406 Malus silvestris Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
229920001807 Urea-formaldehyde Polymers 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000021016 apples Nutrition 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
238000010410 dusting Methods 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
239000008096 xylene Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 1
DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 1
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
OVFIVOVMAPYCNB-UHFFFAOYSA-N 1-[[3-(4-chlorophenyl)-2-phenyloxiran-2-yl]methyl]imidazole Chemical compound C1=CC(Cl)=CC=C1C1C(C=2C=CC=CC=2)(CN2C=NC=C2)O1 OVFIVOVMAPYCNB-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
BAZBYDHOWMSZBD-UHFFFAOYSA-N 2,4,5-trimethylfuran-3-carboxylic acid Chemical compound CC=1OC(C)=C(C(O)=O)C=1C BAZBYDHOWMSZBD-UHFFFAOYSA-N 0.000 description 1
CNTHHNPBADVTRY-UHFFFAOYSA-N 2,5-dimethylfuran-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)O1 CNTHHNPBADVTRY-UHFFFAOYSA-N 0.000 description 1
YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 description 1
KCXZRESSSSYYCW-UHFFFAOYSA-N 2-(4-fluorophenyl)acetaldehyde Chemical compound FC1=CC=C(CC=O)C=C1 KCXZRESSSSYYCW-UHFFFAOYSA-N 0.000 description 1
UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
YAUCKEPYKXHCFF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;manganese Chemical compound [Mn].NC(=S)SCCSC(N)=S YAUCKEPYKXHCFF-UHFFFAOYSA-N 0.000 description 1
JMZRZEXRYJUHEB-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate;zinc Chemical compound [Zn].NC(=S)SCCSC(N)=S JMZRZEXRYJUHEB-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
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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 1
125000000335 thiazolyl group Chemical group 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
238000009369 viticulture Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
MAZZTUAWFTWGKB-UHFFFAOYSA-L zinc ethane-1,2-diamine manganese(2+) dicarbamodithioate Chemical compound [Mn+2].[Zn+2].NCCN.NC([S-])=S.NC([S-])=S MAZZTUAWFTWGKB-UHFFFAOYSA-L 0.000 description 1
DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD89331211A 1988-07-29 1989-07-27 Fungizide mittel DD283911A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3825841A DE3825841A1 (de)	1988-07-29	1988-07-29	1-halogen-1-azolypropene und -methyloxirane und diese enthaltende fungizide

Publications (1)

Publication Number	Publication Date
DD283911A5 true DD283911A5 (de)	1990-10-31

Family

ID=6359864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89331211A DD283911A5 (de)	1988-07-29	1989-07-27	Fungizide mittel

Country Status (14)

Country	Link
US (1)	US5017594A (fr)
EP (1)	EP0352673B1 (fr)
JP (1)	JPH0278664A (fr)
KR (1)	KR910002841A (fr)
AT (1)	ATE102620T1 (fr)
AU (1)	AU610746B2 (fr)
CA (1)	CA1334594C (fr)
DD (1)	DD283911A5 (fr)
DE (2)	DE3825841A1 (fr)
ES (1)	ES2050191T3 (fr)
HU (1)	HU206247B (fr)
IL (1)	IL90846A (fr)
NZ (1)	NZ230106A (fr)
ZA (1)	ZA895759B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3911059A1 (de) *	1989-04-06	1990-10-11	Basf Ag	1-alkoxy-1-azolylmethyloxirane, verfahren zu ihrer herstellung und ihre verwendung als pflanzenschutzmittel
IL95493A0 (en) *	1989-09-09	1991-06-30	Basf Ag	Azolylmethyloxiranes,their manufacture and their use as fungicides
GB2255333B (en) *	1991-05-01	1994-08-31	Matsura Kenkyusyo Kabushiki Ka	Cargo docking apparatus including forklifts
ES2400220T3 (es) *	2009-02-05	2013-04-08	Basf Se	Procedimiento para la producción de hidroximetildifeniloxiranos y los correspondentes 1-azolilmetil-1,2-difeniloxiranos
US10179891B2 (en)	2012-07-25	2019-01-15	Basf Se	Use of branched polyesters based on citric acid as additive in washing compositions, detergents or a formulation for water treatment
EP2746279A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés triazolyles et imidazolyles fongicides
EP2746277A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés triazolyles et imidazolyles fongicides
CN109293602B (zh) *	2018-09-26	2020-11-10	江苏七洲绿色化工股份有限公司	一种氟环唑中间体及氟环唑的制备方法

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1533375A (en) *	1976-07-20	1978-11-22	Bayer Ag	Halogenated 1-azolyl-butane derivatives and their use as fungicides
DE2652313A1 (de) *	1976-11-17	1978-05-18	Basf Ag	Triazolderivate
DE2960167D1 (en) *	1978-03-17	1981-04-02	Ciba Geigy Ag	1.1-diphenylethene derivatives, process for their preparation and their use as microbicides
DE3210570A1 (de) *	1982-03-23	1983-10-06	Hoechst Ag	3-azolyl-1,2-diaryl-1-halogen-1-propene, ihre herstellung, ihre verwendung als pflanzenschutzmittel und diese verbindungen enthaltende praeparate
DE3218130A1 (de) *	1982-05-14	1983-11-17	Basf Ag, 6700 Ludwigshafen	Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide
IL68433A (en) *	1982-05-14	1986-04-29	Basf Ag	Azolylmethyloxiranes,their manufacture and their use as fungicides and in pharmaceutical compositions
KR880001813B1 (ko) *	1983-01-10	1988-09-19	시바-가이기 코오포레이숀	플루오로아졸릴 프로판 유도체의 제조방법
GB8305377D0 (en) *	1983-02-25	1983-03-30	Pfizer Ltd	Antifungal agents
DE3327036A1 (de) *	1983-07-27	1985-02-07	Bayer Ag, 5090 Leverkusen	3-(1,2,4-triazol-1-yl)-l-propene
DE3572809D1 (de) *	1984-05-23	1989-10-12	Ciba Geigy Ag	Microbicidal 1-fluoro-1-azolyl-2,2-diarylethane derivatives
IL78175A (en) *	1985-03-29	1989-10-31	Basf Ag	Azolylmethyloxiranes,their preparation and their use as fungicide crop protection agents
DE3511411A1 (de) *	1985-03-29	1986-10-02	Basf Ag, 6700 Ludwigshafen	Verwendung von azolylmethyloxiranen zur bekaempfung von viralen erkrankungen
CA1321588C (fr) *	1986-07-02	1993-08-24	Katherine Eleanor Flynn	Alpha-aryl-alpha-phenethyl-1h-1,2,4-triazole-1- propanenitriles
DE3809069A1 (de) *	1988-03-18	1989-09-28	Basf Ag	Azolylmethylallylalkohole und diese enthaltende fungizide

1988
- 1988-07-29 DE DE3825841A patent/DE3825841A1/de not_active Withdrawn
1989
- 1989-07-03 IL IL90846A patent/IL90846A/xx not_active IP Right Cessation
- 1989-07-05 CA CA000604816A patent/CA1334594C/fr not_active Expired - Fee Related
- 1989-07-07 US US07/376,429 patent/US5017594A/en not_active Expired - Fee Related
- 1989-07-22 EP EP89113500A patent/EP0352673B1/fr not_active Expired - Lifetime
- 1989-07-22 DE DE89113500T patent/DE58907160D1/de not_active Expired - Lifetime
- 1989-07-22 ES ES89113500T patent/ES2050191T3/es not_active Expired - Lifetime
- 1989-07-22 AT AT89113500T patent/ATE102620T1/de not_active IP Right Cessation
- 1989-07-27 DD DD89331211A patent/DD283911A5/de unknown
- 1989-07-27 NZ NZ230106A patent/NZ230106A/en unknown
- 1989-07-28 ZA ZA895759A patent/ZA895759B/xx unknown
- 1989-07-28 JP JP1194450A patent/JPH0278664A/ja active Pending
- 1989-07-28 HU HU893906A patent/HU206247B/hu not_active IP Right Cessation
- 1989-07-28 AU AU39051/89A patent/AU610746B2/en not_active Ceased
- 1989-07-29 KR KR1019890010784A patent/KR910002841A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
JPH0278664A (ja)	1990-03-19
KR910002841A (ko)	1991-02-26
DE3825841A1 (de)	1990-02-01
EP0352673A2 (fr)	1990-01-31
ES2050191T3 (es)	1994-05-16
US5017594A (en)	1991-05-21
CA1334594C (fr)	1995-02-28
ZA895759B (en)	1991-03-27
EP0352673A3 (en)	1990-04-25
AU3905189A (en)	1990-02-01
IL90846A (en)	1993-05-13
DE58907160D1 (de)	1994-04-14
EP0352673B1 (fr)	1994-03-09
AU610746B2 (en)	1991-05-23
IL90846A0 (en)	1990-02-09
NZ230106A (en)	1990-12-21
ATE102620T1 (de)	1994-03-15
HU206247B (en)	1992-10-28

Legal Events

Date	Code	Title	Description
1992-08-27	EPE	Extended patent has ceased

Publication	Publication Date	Title
EP0196038A2 (fr)	1986-10-01	Azolylméthyloxiranes, leur préparation et leur utilisation comme agents protecteurs pour les plantes
DD244057A5 (de)	1987-03-25	Fungizide mittel
DE3907729A1 (de)	1990-09-13	Trifluormethylphenylazolylmethyloxirane, verfahren zu ihrer herstellung und deren verwendung als pflanzenschutzmittel
EP0352675A2 (fr)	1990-01-31	Imidazolylméthyloxiranes substitués et imidazolylpropènes substitués, leur préparation et fongicides les contenant
DD283911A5 (de)	1990-10-31	Fungizide mittel
DE3806089A1 (de)	1989-09-07	Azolylmethyloxirane und diese enthaltende fungizide
EP0332073A1 (fr)	1989-09-13	Imidazolylméthyloxiranes fungicides
DE3809069A1 (de)	1989-09-28	Azolylmethylallylalkohole und diese enthaltende fungizide
DE4028392A1 (de)	1992-03-12	Azolylmethyloxirane und diese enthaltende fungizide
EP0330132A1 (fr)	1989-08-30	Azolylméthylcycloalkyloxiranes, leur préparation et utilisation comme agents phytosanitaires
EP0391311B1 (fr)	1994-03-16	1-Alkoxy-1-azolylméthyloxiranes, leur procédé de préparation et leur application comme herbicides
DE3805376A1 (de)	1989-08-31	Neue azolylmethyloxirane und diese enthaltende fungizide
EP0346727A1 (fr)	1989-12-20	Dérivés du 1-halogène-1-azolyl-éthane et fongicides les contenant
EP0345639A1 (fr)	1989-12-13	Alpha-hydroxy azolyléthyloxirannes et fongicides les contenant
EP0207411B1 (fr)	1989-01-18	Sels o-substitués de 3-oxypyridinium, procédé pour leur préparation, et leur utilisation comme fongicides pour la protection des plantes
DE4034337A1 (de)	1992-04-30	Azolylmethylcyclohexanole und diese enthaltende fungizide
DE3536529A1 (de)	1987-04-23	Azolylmethyloxirane - ihre herstellung und verwendung als pflanzenschutzmittel
DE3913725A1 (de)	1990-10-31	1-halogenvinyl-azole und diese enthaltende fungizide und wachstumsregulatoren
DE4034352A1 (de)	1992-04-30	1-halogen-1-azolylmethanderivate und diese enthaltende fungizide
DE3930166A1 (de)	1991-03-21	Azolylmethyloxirane und diese enthaltende fungizide
DE3923153A1 (de)	1991-01-24	1-halogen-vinylazole und diese enthaltende fungizide
DE4009594A1 (de)	1991-10-02	Fungizide azolylethanderivate
EP0337198A2 (fr)	1989-10-18	Allyl-triazoles et fongicides les contenant
DE4022784A1 (de)	1992-01-23	Azolylmethylcycloalkanole und diese enthaltende pflanzenschutzmittel
DE3811916A1 (de)	1989-10-19	Azolylalkene und diese enthaltende fungizide