DD221342A5 - Fungizide mittel - Google Patents

Fungizide mittel Download PDF

Info

Publication number: DD221342A5
Authority: DD; German Democratic Republic
Prior art keywords: carbon atoms; formula; carbinols; item; ketones
Prior art date: 1983-04-30

Application number

DD84262368A

Other languages

German (de)

English (en)

Inventor

Udo Kraatz

Karl H Buechel

Paul Reinecke

Wilhelm Brandes

Gerd Haenssler

Original Assignee

Bayer Ag

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.)

1983-04-30

Filing date

1984-04-26

Publication date

1985-04-24

1984-04-26 Application filed by Bayer Ag filed Critical Bayer Ag

1985-04-24 Publication of DD221342A5 publication Critical patent/DD221342A5/de

Links

239000000417 fungicide Substances 0.000 title claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 12
JQSXAKLQKRLUHL-UHFFFAOYSA-N bis(5-phenoxy-2h-triazol-4-yl)methanone Chemical class N=1NN=C(OC=2C=CC=CC=2)C=1C(=O)C1=NNN=C1OC1=CC=CC=C1 JQSXAKLQKRLUHL-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
239000000460 chlorine Chemical group 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
229910052751 metal Chemical class 0.000 claims description 8
239000002184 metal Chemical class 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000000468 ketone group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 6
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000262 haloalkenyl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000011814 protection agent Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
241000233866 Fungi Species 0.000 claims 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 49
201000010099 disease Diseases 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
239000004480 active ingredient Substances 0.000 abstract description 5
150000002989 phenols Chemical class 0.000 abstract description 5
240000007594 Oryza sativa Species 0.000 abstract description 4
239000000575 pesticide Substances 0.000 abstract description 4
235000007164 Oryza sativa Nutrition 0.000 abstract description 3
241000317942 Venturia <ichneumonid wasp> Species 0.000 abstract description 3
235000013339 cereals Nutrition 0.000 abstract description 3
235000009566 rice Nutrition 0.000 abstract description 3
241000196324 Embryophyta Species 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 14
-1 4-Bromophenoxy Chemical group 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
239000003995 emulsifying agent Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
238000009472 formulation Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000003960 organic solvent Substances 0.000 description 7
230000001681 protective effect Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000126 substance Substances 0.000 description 6
125000002877 alkyl aryl group Chemical group 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
239000000969 carrier Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
230000000855 fungicidal effect Effects 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
238000005554 pickling Methods 0.000 description 4
239000000843 powder Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002689 soil Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000011701 zinc Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
241000190150 Bipolaris sorokiniana Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
KIVDZERHEZTUGL-UHFFFAOYSA-N 1-bromo-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)C(Br)N1C=NC=N1 KIVDZERHEZTUGL-UHFFFAOYSA-N 0.000 description 2
STYJVCJUJGDUEC-UHFFFAOYSA-N 1-fluoro-3,3-dimethyl-1-phenoxybutan-2-one Chemical compound CC(C)(C)C(=O)C(F)OC1=CC=CC=C1 STYJVCJUJGDUEC-UHFFFAOYSA-N 0.000 description 2
NQYYMVQNMWPZQK-UHFFFAOYSA-N 2-(2,6-dichlorophenoxy)-1-phenyl-2-(1,2,4-triazol-1-yl)ethanone Chemical compound ClC1=CC=CC(Cl)=C1OC(N1N=CN=C1)C(=O)C1=CC=CC=C1 NQYYMVQNMWPZQK-UHFFFAOYSA-N 0.000 description 2
PWRCOONECNWDBH-UHFFFAOYSA-N 4-prop-2-enoxyphenol Chemical compound OC1=CC=C(OCC=C)C=C1 PWRCOONECNWDBH-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
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000251730 Chondrichthyes Species 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000228452 Venturia inaequalis Species 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
150000008052 alkyl sulfonates Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 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
239000003814 drug Substances 0.000 description 2
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229910052500 inorganic mineral Inorganic materials 0.000 description 2
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238000002955 isolation Methods 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
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125000001424 substituent group Chemical group 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
WJZRIGCFBNOWMN-UHFFFAOYSA-N 1-(4-bromophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Br)C=C1 WJZRIGCFBNOWMN-UHFFFAOYSA-N 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
WTDHSODZVUOZOU-UHFFFAOYSA-N 1-bromo-1-chloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Cl)Br WTDHSODZVUOZOU-UHFFFAOYSA-N 0.000 description 1
HWLZJIJKCKHVAM-UHFFFAOYSA-N 1-fluoro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CF HWLZJIJKCKHVAM-UHFFFAOYSA-N 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
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RGCKGOZRHPZPFP-UHFFFAOYSA-N Alizarin Natural products C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
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229910052796 boron Inorganic materials 0.000 description 1
239000001273 butane Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000011161 development Methods 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
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005283 haloketone group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000004579 marble Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003595 mist Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000008659 phytopathology Effects 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
208000029561 pustule Diseases 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
- 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)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD84262368A 1983-04-30 1984-04-26 Fungizide mittel DD221342A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3315806A DE3315806A1 (de)	1983-04-30	1983-04-30	Phenoxytriazolyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide

Publications (1)

Publication Number	Publication Date
DD221342A5 true DD221342A5 (de)	1985-04-24

Family

ID=6197841

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84262368A DD221342A5 (de)	1983-04-30	1984-04-26	Fungizide mittel

Country Status (19)

Country	Link
US (1)	US4610996A (fr)
EP (1)	EP0124012A3 (fr)
JP (1)	JPS59206366A (fr)
KR (1)	KR840008339A (fr)
AU (1)	AU562528B2 (fr)
BR (1)	BR8401974A (fr)
CA (1)	CA1223263A (fr)
DD (1)	DD221342A5 (fr)
DE (1)	DE3315806A1 (fr)
DK (1)	DK212684A (fr)
ES (1)	ES532015A0 (fr)
GR (1)	GR81495B (fr)
HU (1)	HUT34108A (fr)
IL (1)	IL71680A0 (fr)
NZ (1)	NZ207988A (fr)
PH (1)	PH20241A (fr)
PT (1)	PT78468B (fr)
TR (1)	TR22220A (fr)
ZA (1)	ZA843154B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5013847A (en) *	1988-07-29	1991-05-07	Basf Aktiengesellschaft	Phenoxyalkyl-substituted heteroaromatics and a method for controlling pests
CN103848824A (zh) *	2012-12-05	2014-06-11	江苏七洲绿色化工股份有限公司	香豆素-三唑类化合物及其制备方法和用途

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2401715C3 (de) *	1974-01-15	1981-10-22	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von 1-(1,2,4-Triazol-1-yl)-1-phenoxy-3,3-dimethyl-butan-2-on-Derivaten
DE2423987C2 (de) *	1974-05-17	1986-01-16	Bayer Ag, 5090 Leverkusen	Metallkomplexe von Azolyläthern, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE2455955A1 (de) *	1974-11-27	1976-08-12	Bayer Ag	Fungizide mittel
DE2743767A1 (de) *	1977-09-29	1979-04-12	Bayer Ag	Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE2758784A1 (de) *	1977-12-29	1979-07-12	Basf Ag	Triazolyl-glykolaether
DE2925687A1 (de) *	1979-06-26	1981-01-22	Basf Ag	Triazolylglykolether enthaltende mittel zur regulierung des pflanzenwachstums
DE2937595A1 (de) *	1979-09-18	1981-04-02	Bayer Ag, 5090 Leverkusen	Verfahren zur herstellung von 1-azolyl-1-phenoxy-alkan-2-onen

1983
- 1983-04-30 DE DE3315806A patent/DE3315806A1/de not_active Withdrawn
1984
- 1984-04-11 US US06/599,035 patent/US4610996A/en not_active Expired - Fee Related
- 1984-04-17 AU AU27006/84A patent/AU562528B2/en not_active Ceased
- 1984-04-17 EP EP84104331A patent/EP0124012A3/fr not_active Withdrawn
- 1984-04-23 PT PT78468A patent/PT78468B/pt unknown
- 1984-04-24 TR TR22220A patent/TR22220A/xx unknown
- 1984-04-26 DD DD84262368A patent/DD221342A5/de unknown
- 1984-04-27 CA CA000452958A patent/CA1223263A/fr not_active Expired
- 1984-04-27 HU HU841657A patent/HUT34108A/hu unknown
- 1984-04-27 IL IL71680A patent/IL71680A0/xx unknown
- 1984-04-27 JP JP59084194A patent/JPS59206366A/ja active Pending
- 1984-04-27 ZA ZA843154A patent/ZA843154B/xx unknown
- 1984-04-27 PH PH30610A patent/PH20241A/en unknown
- 1984-04-27 NZ NZ207988A patent/NZ207988A/en unknown
- 1984-04-27 DK DK212684A patent/DK212684A/da not_active Application Discontinuation
- 1984-04-27 ES ES532015A patent/ES532015A0/es active Granted
- 1984-04-27 GR GR74526A patent/GR81495B/el unknown
- 1984-04-27 BR BR8401974A patent/BR8401974A/pt unknown
- 1984-04-30 KR KR1019840002307A patent/KR840008339A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
US4610996A (en)	1986-09-09
GR81495B (fr)	1984-12-11
TR22220A (tr)	1986-07-10
DK212684D0 (da)	1984-04-27
CA1223263A (fr)	1987-06-23
NZ207988A (en)	1986-04-11
PH20241A (en)	1986-11-10
EP0124012A2 (fr)	1984-11-07
BR8401974A (pt)	1984-12-04
EP0124012A3 (fr)	1986-08-20
IL71680A0 (en)	1984-07-31
PT78468A (en)	1984-05-01
AU2700684A (en)	1984-11-01
ES8502101A1 (es)	1984-12-16
PT78468B (en)	1986-05-27
DE3315806A1 (de)	1984-10-31
ZA843154B (en)	1984-12-24
JPS59206366A (ja)	1984-11-22
HUT34108A (en)	1985-02-28
DK212684A (da)	1984-10-31
KR840008339A (ko)	1984-12-14
ES532015A0 (es)	1984-12-16
AU562528B2 (en)	1987-06-11

Publication	Publication Date	Title
EP0077479A2 (fr)	1983-04-27	Phénoxyphényl-azolylméthyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides et intermédiaires
EP0096786B1 (fr)	1987-09-16	Dérivés hydroxyalkynyl-azolyles, leur procédé de préparation et leur application comme fongicides
DD140411A5 (de)	1980-03-05	Fungizide mittel
EP0019189B1 (fr)	1982-07-28	Agents fongicides, procédé pour leur préparation, ainsi que leur utilisation comme fongicides
EP0019131B1 (fr)	1982-12-22	Dérivés fluorés du 1-triazolyl butane, procédé pour leur préparation et leur application comme fongicides
EP0071009B1 (fr)	1987-02-04	Dérivés d'alcinyl-azol fongicide et leur utilisation
EP0047405B1 (fr)	1984-06-20	Dérivés azolylalkyles, leur procédé de préparation et leur application comme fongicides
EP0010674B1 (fr)	1982-01-27	Dérivés d'éthène-azole, procédé pour leur préparation, compositions fongicides, procédé de préparation de ces compositions, utilisation des dérivés d'azole pour combattre les champignons et méthode de lutte contre les champignons
EP0016974A1 (fr)	1980-10-15	Dérivés de la pyridine substituée en position 3, procédé pour leur préparation, leur utilisation comme fongicides et composés intermédiaires
DE2929602A1 (de)	1981-02-12	Triazolyl-alken-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0076370A1 (fr)	1983-04-13	Dérivés phénoxy azolyl substitués, leur procédé de synthèse et leur application comme fongicides
EP0032561A1 (fr)	1981-07-29	Dérivés de triazolylphénacyl-pyridyléthers, procédé pour leur préparation et leur utilisation comme fongicides
EP0042980A2 (fr)	1982-01-06	1-Azolyl-1-phénoxy-3,3-diméthyl-butan-2-ones et -2-ols, substitués en position 4, leur procédé de préparation et leur application comme fongicides
DD213825A5 (de)	1984-09-26	Pflanzenschutzmittel
EP0023286B1 (fr)	1983-04-13	Azolyl-alcénols, procédé pour leur préparation ainsi que leur utilisation comme fongicides
EP0109476A1 (fr)	1984-05-30	Phénoxypropyltriazolyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides ainsi que des intermédiaires de synthèse
EP0135083A2 (fr)	1985-03-27	3-Cycloalkyl-1-(1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-propan-1-ones et -propan-1-ols
EP0198191B1 (fr)	1989-09-06	Pipérazinylméthyl-1,2,4-triazolylméthylcarbinols
EP0118069A1 (fr)	1984-09-12	Fongicides contenant des 1,3-diazolyl-propanols
EP0047420A2 (fr)	1982-03-17	Dérivés fluorés de l'1-azolyl-butane, leur procédé de préparation et leur application comme fongicides
EP0189044A2 (fr)	1986-07-30	1-Aryl-2,2-dialkyl-2-(1,2,4-triazol-1-yl)-éthanols
EP0040367A1 (fr)	1981-11-25	Phényl-triazolyl-vinyl-cétones substituées, procédé pour leur préparation ainsi que leur application comme fongicides
EP0066771B1 (fr)	1984-10-03	1-Iodo-1-propyn-3-ols, procédé pour leur préparation et leur utilisation comme agent de protection des plantes
EP0124012A2 (fr)	1984-11-07	Phénoxytriazolyl-cétones et carbinols, leur procédé de préparation et leur application comme fongicides
DD221343A5 (de)	1985-04-24	Fungizide mittel