DD206728A5 - Fungizide mittel - Google Patents

Fungizide mittel Download PDF

Info

Publication number: DD206728A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; carbon atoms; alkyl; cycloalkyl; formula
Prior art date: 1981-10-10

Application number

DD82243875A

Other languages

German (de)

English (en)

Inventor

Hans-Ludwig Elbe

Karl H Buechel

Wilhelm Brandes

Paul-Ernst Frohberger

Volker Paul

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.)

1981-10-10

Filing date

1982-10-08

Publication date

1984-02-08

1982-10-08 Application filed by Bayer Ag filed Critical Bayer Ag

1984-02-08 Publication of DD206728A5 publication Critical patent/DD206728A5/de

Links

239000000417 fungicide Substances 0.000 title claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 37
239000001257 hydrogen Substances 0.000 claims abstract description 37
-1 1,2,4-triazole-1-yl Chemical group 0.000 claims abstract description 25
238000002360 preparation method Methods 0.000 claims abstract description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 10
230000000855 fungicidal effect Effects 0.000 claims abstract description 8
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 6
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 92
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 38
238000000034 method Methods 0.000 claims description 30
150000002431 hydrogen Chemical class 0.000 claims description 24
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 19
239000011737 fluorine Substances 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
229910052751 metal Chemical class 0.000 claims description 9
239000002184 metal Chemical class 0.000 claims description 9
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 7
FYAOHNSWANDMPC-UHFFFAOYSA-N 1,3-diphenoxy-1,3-diphenyl-1,3-bis(1h-pyrrol-2-yl)propan-2-one Chemical class C=1C=CC=CC=1OC(C=1C=CC=CC=1)(C=1NC=CC=1)C(=O)C(C=1C=CC=CC=1)(C=1NC=CC=1)OC1=CC=CC=C1 FYAOHNSWANDMPC-UHFFFAOYSA-N 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
229910052727 yttrium Inorganic materials 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
239000004606 Fillers/Extenders Substances 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000011814 protection agent Substances 0.000 claims description 5
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 4
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 4
241000233866 Fungi Species 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 3
239000000543 intermediate Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 claims 1
125000005429 oxyalkyl group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 8
239000003795 chemical substances by application Substances 0.000 abstract description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
150000001875 compounds Chemical class 0.000 description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
241000196324 Embryophyta Species 0.000 description 17
239000002904 solvent Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
239000003995 emulsifying agent Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003085 diluting agent Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
230000001681 protective effect Effects 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000000243 solution Substances 0.000 description 6
240000007594 Oryza sativa Species 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
150000002902 organometallic compounds Chemical class 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
101150065749 Churc1 gene Proteins 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
102100038239 Protein Churchill Human genes 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
150000001298 alcohols Chemical class 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZCIJLRUKSWOMIT-UHFFFAOYSA-N 1,3-diphenyl-1,3-bis(1h-pyrrol-2-yl)propan-2-one Chemical compound C=1C=CNC=1C(C=1C=CC=CC=1)C(=O)C(C=1C=CC=CC=1)C1=CC=CN1 ZCIJLRUKSWOMIT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 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
238000003556 assay Methods 0.000 description 3
150000003851 azoles Chemical class 0.000 description 3
DKEKURXRUXRNES-UHFFFAOYSA-N bis(1h-pyrrol-2-yl)methanone Chemical class C=1C=CNC=1C(=O)C1=CC=CN1 DKEKURXRUXRNES-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
125000005283 haloketone group Chemical group 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000002689 soil Substances 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
241000221787 Erysiphe Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
241001617088 Thanatephorus sasakii Species 0.000 description 2
241000317942 Venturia <ichneumonid wasp> 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
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000003899 bactericide agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000013339 cereals Nutrition 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
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
231100000676 disease causative agent Toxicity 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000003948 formamides Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 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
238000004519 manufacturing process Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000003444 phase transfer catalyst Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
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238000004821 distillation Methods 0.000 description 1
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FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
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238000000746 purification Methods 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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230000002940 repellent Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
229960004889 salicylic acid Drugs 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
239000002002 slurry Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
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OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
- 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)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD82243875A 1981-10-10 1982-10-08 Fungizide mittel DD206728A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813140276 DE3140276A1 (de)	1981-10-10	1981-10-10	Phenoxyphenyl-azolylmethyl-ketone und -carbinole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und als zwischenprodukte

Publications (1)

Publication Number	Publication Date
DD206728A5 true DD206728A5 (de)	1984-02-08

Family

ID=6143812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82243875A DD206728A5 (de)	1981-10-10	1982-10-08	Fungizide mittel

Country Status (16)

Country	Link
EP (1)	EP0077479A3 (fr)
JP (1)	JPS5872568A (fr)
AU (1)	AU8922382A (fr)
BR (1)	BR8205929A (fr)
CA (1)	CA1187084A (fr)
CS (1)	CS235964B2 (fr)
DD (1)	DD206728A5 (fr)
DE (1)	DE3140276A1 (fr)
DK (1)	DK447082A (fr)
ES (1)	ES516368A0 (fr)
GR (1)	GR77014B (fr)
IL (1)	IL66942A0 (fr)
NZ (1)	NZ202107A (fr)
PL (1)	PL134646B1 (fr)
PT (1)	PT75638B (fr)
ZA (1)	ZA827370B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2143815B (en) *	1983-05-19	1988-01-20	Ciba Geigy Ag	Process for the preparation of micro biocidal 1-triazolylethyl ether derivatives
DE3322526A1 (de) *	1983-06-23	1985-01-10	Basf Ag, 6700 Ludwigshafen	Fungizide azolverbindungen, ihre herstellung und verwendung
HUT36990A (en) *	1983-07-08	1985-11-28	Sandoz Ag	Fungicide preparates containing azole derivatives as active ingredient and method for producing azole derivates and medicine preparates containing these compunds
US4690942A (en) *	1983-12-20	1987-09-01	Ciba-Geigy Corporation	1-aryl-2-fluoro-2-azolyl alkanones, alkanols, esters, and ethers, composition containing them, and use of them to control phytopathogenic microorganisms
DE3501370A1 (de) *	1985-01-17	1986-07-17	Bayer Ag, 5090 Leverkusen	1-aryl-2,2-dialkyl-2-(1,2,4-triazol-1-yl)-ethanole
GB8511344D0 (en) *	1985-05-03	1985-06-12	Ici Plc	Heterocyclic compounds
EP0275955B1 (fr) *	1987-01-21	1990-07-04	Ciba-Geigy Ag	Composition microbicide
MD36C2 (ro) *	1988-08-04	1995-03-31	Циба-Гейги АГ	Procedeu de combatere a micetelor
WO2011136285A1 (fr) *	2010-04-27	2011-11-03	日本製紙株式会社	Promoteur de différenciation cellulaire et son utilisation
BR112015012003A2 (pt) *	2012-11-27	2018-05-15	Basf Se	compostos de fórmula i, composição, utilização de um composto, método para o combate dos fungos nocivos, semente, processo para a preparação dos compostos e compostos intermediários
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WO2014082879A1 (fr)	2012-11-27	2014-06-05	Basf Se	Composés de [1,2,4]triazole substitués
CN105008336A (zh) *	2012-11-27	2015-10-28	巴斯夫欧洲公司	取代2-[苯氧基苯基]-1-[1,2,4]三唑-1-基乙醇化合物及其作为杀真菌剂的用途
EP2925732A1 (fr)	2012-11-27	2015-10-07	Basf Se	Composés de [1,2,4]triazole substitués
EP2746263A1 (fr)	2012-12-19	2014-06-25	Basf Se	Triazoles à substitution alpha et imidazoles
EP2745691A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés d'imidazole substitués et leur utilisation comme fongicides
US20150307460A1 (en)	2012-12-19	2015-10-29	Basf Se	Substituted Triazoles and Imidazoles and Their Use as Fungicides
EP2746274A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés de [1,2,4] triazole substitué
EP2746278A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés de [1,2,4]triazole et d'imidazole substitués
EP2746262A1 (fr)	2012-12-19	2014-06-25	Basf Se	Composés de [1,2,4]triazole et d'imidazole substitués pour combattre les champignons phytopathogènes
CA2894264C (fr)	2012-12-20	2023-03-07	BASF Agro B.V.	Compositions comprenant un compose triazole
EP2943476B1 (fr)	2013-01-09	2019-05-15	BASF Agro B.V.	Procédé de préparation de triazoles et d'oxiranes substitués
BR112016000299B8 (pt)	2013-07-08	2021-04-20	Basf Agro Bv	composições, uso de uma composição, método para o combate dos fungos fitopatogênicos e uso dos componentes
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WO2016071167A1 (fr)	2014-11-07	2016-05-12	Basf Se	Mélanges pesticides
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DE2832234A1 (de) *	1978-07-21	1980-01-31	Bayer Ag	Alpha -azolyl-keto-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide

1981
- 1981-10-10 DE DE19813140276 patent/DE3140276A1/de not_active Withdrawn
1982
- 1982-09-29 EP EP82108991A patent/EP0077479A3/fr not_active Withdrawn
- 1982-10-01 PT PT75638A patent/PT75638B/pt unknown
- 1982-10-07 JP JP57175430A patent/JPS5872568A/ja active Pending
- 1982-10-07 IL IL66942A patent/IL66942A0/xx unknown
- 1982-10-07 CS CS827177A patent/CS235964B2/cs unknown
- 1982-10-07 NZ NZ202107A patent/NZ202107A/en unknown
- 1982-10-08 AU AU89223/82A patent/AU8922382A/en not_active Abandoned
- 1982-10-08 PL PL1982238571A patent/PL134646B1/pl unknown
- 1982-10-08 BR BR8205929A patent/BR8205929A/pt unknown
- 1982-10-08 GR GR69481A patent/GR77014B/el unknown
- 1982-10-08 ZA ZA827370A patent/ZA827370B/xx unknown
- 1982-10-08 DD DD82243875A patent/DD206728A5/de unknown
- 1982-10-08 CA CA000413102A patent/CA1187084A/fr not_active Expired
- 1982-10-08 DK DK447082A patent/DK447082A/da not_active Application Discontinuation
- 1982-10-08 ES ES516368A patent/ES516368A0/es active Granted

Also Published As

Publication number	Publication date
PT75638B (en)	1985-01-11
AU8922382A (en)	1983-04-21
CS235964B2 (en)	1985-05-15
GR77014B (fr)	1984-09-04
PL238571A1 (en)	1983-05-23
EP0077479A2 (fr)	1983-04-27
ZA827370B (en)	1983-08-31
ES8307004A1 (es)	1983-06-16
NZ202107A (en)	1985-07-12
ES516368A0 (es)	1983-06-16
IL66942A0 (en)	1983-02-23
DK447082A (da)	1983-04-11
JPS5872568A (ja)	1983-04-30
CA1187084A (fr)	1985-05-14
BR8205929A (pt)	1983-09-13
EP0077479A3 (fr)	1983-05-25
PL134646B1 (en)	1985-08-31
PT75638A (en)	1982-11-01
DE3140276A1 (de)	1983-04-28

Publication	Publication Date	Title
DD206728A5 (de)	1984-02-08	Fungizide mittel
EP0096786B1 (fr)	1987-09-16	Dérivés hydroxyalkynyl-azolyles, leur procédé de préparation et leur application comme fongicides
EP0025949B1 (fr)	1983-07-20	Triazolyl-gamma-fluoropinacolols acylés, procédé pour leur préparation et leur application comme fongicides
EP0019131B1 (fr)	1982-12-22	Dérivés fluorés du 1-triazolyl butane, procédé pour leur préparation et leur application comme fongicides
EP0054865A1 (fr)	1982-06-30	1-Azolyl-butan-2-ones substitués, procédé de leur préparation et leur application comme fongicides ainsi que comme intermédiaires
EP0103798B1 (fr)	1986-12-30	Azolylalkyl-t-butyl-cétones et -carbinols substitués
DE2920374A1 (de)	1980-11-20	Fungizide mittel, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0004303A1 (fr)	1979-10-03	Dérivés acylés du 1-azolyl-2-hydroxy-butane, leur procédé de préparation ainsi que leur utilisation comme fongicides
EP0131845A2 (fr)	1985-01-23	Utilisation de diazolylalkylecarbinols substitués pour la protection de plantes contre les champignons
EP0047405B1 (fr)	1984-06-20	Dérivés azolylalkyles, leur procédé de préparation et leur application comme fongicides
EP0108995B1 (fr)	1986-05-28	Dérivés hydroxyalkinyl-azolyliques
DE2842137A1 (de)	1980-04-17	Halogenierte 1-azolyl-1-fluorphenoxy- butan-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
EP0109476A1 (fr)	1984-05-30	Phénoxypropyltriazolyl-cétones et -carbinols, leur procédé de préparation et leur application comme fongicides ainsi que des intermédiaires de synthèse
EP0025948B1 (fr)	1983-03-02	Dérivés acylés d'imidazolyl-gamma fluoropinacolyl, procédé pour leur préparation et leur utilisation comme fongicides
DE3321023A1 (de)	1984-12-13	Triazolylalkohole, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0141205A2 (fr)	1985-05-15	Dérivés d'hydroxyéthylazolyl-oximes
EP0023286A2 (fr)	1981-02-04	Azolyl-alcénols, procédé pour leur préparation ainsi que leur utilisation comme fongicides
DD201842A5 (de)	1983-08-17	Fungizide mittel
DD221343A5 (de)	1985-04-24	Fungizide mittel
EP0141204A2 (fr)	1985-05-15	Dérivés de hydroxyéthylazoles
EP0129115A2 (fr)	1984-12-27	Dérivés d'azolylméthyl-thiényl-carbinols
DE3441526A1 (de)	1986-05-15	Triazolylmethylcarbinol-arylacetale
DE2918893A1 (de)	1980-11-20	Fluorierte 1-imidazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
EP0019190A2 (fr)	1980-11-26	Utilisation des hydroxyalkyl-imidazoles comme fongicides
DD152466A5 (de)	1981-12-02	Fungizide mittel