CA1241658A - 2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides - Google Patents

2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides

Info

Publication number: CA1241658A
Authority: CA; Canada
Prior art keywords: formula; carbon atoms; compound; phenyl; reaction
Prior art date: 1983-04-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000547804A

Other languages

English (en)

Inventor

Erik Regel

Karl H. Buchel

Paul Reinecke

Wilhelm Brandes

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

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.)

1983-04-12

Filing date

1987-09-24

Publication date

1988-09-06

1983-04-12 Priority claimed from DE3313073A external-priority patent/DE3313073A1/de

1987-09-24 Application filed by Bayer AG filed Critical Bayer AG

1987-09-24 Priority to CA000547804A priority Critical patent/CA1241658A/fr

1988-09-06 Application granted granted Critical

1988-09-06 Publication of CA1241658A publication Critical patent/CA1241658A/fr

Status Expired legal-status Critical Current

Links

DJQIAXXQEKDMPD-UHFFFAOYSA-N 5-(oxiran-2-ylmethyl)-1h-pyrazole Chemical compound C1=CNN=C1CC1CO1 DJQIAXXQEKDMPD-UHFFFAOYSA-N 0.000 title claims description 6
239000000543 intermediate Substances 0.000 title abstract description 3
239000000417 fungicide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000006193 alkinyl group Chemical group 0.000 claims abstract description 7
125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 40
230000008569 process Effects 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 29
-1 tert.-butyl Chemical group 0.000 claims description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 15
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
239000011230 binding agent Substances 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 3
ANXKZXRDXAZQJT-UHFFFAOYSA-M methyl sulfate;trimethylsulfanium Chemical compound C[S+](C)C.COS([O-])(=O)=O ANXKZXRDXAZQJT-UHFFFAOYSA-M 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 13
230000000855 fungicidal effect Effects 0.000 abstract description 2
125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
235000013350 formula milk Nutrition 0.000 description 61
241000196324 Embryophyta Species 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000009472 formulation Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
229910052751 metal Chemical class 0.000 description 7
239000002184 metal Chemical class 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
239000008187 granular material Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
235000007686 potassium Nutrition 0.000 description 6
229960003975 potassium Drugs 0.000 description 6
150000001340 alkali metals Chemical class 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
229940093956 potassium carbonate Drugs 0.000 description 5
235000011181 potassium carbonates Nutrition 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
239000000969 carrier Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
230000001681 protective effect Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000190150 Bipolaris sorokiniana Species 0.000 description 3
239000004606 Fillers/Extenders Substances 0.000 description 3
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 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
150000003851 azoles Chemical class 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
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
235000015071 dressings Nutrition 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-1h-pyrrole Chemical class C=1C=CNC=1CC1CO1 ZFOWEXGOKLKOFQ-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
206010039509 Scab Diseases 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000012141 concentrate 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
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000003948 formamides Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 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
150000002825 nitriles Chemical class 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
239000006072 paste Substances 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000011814 protection agent Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
UWCXGQLUAITTNP-UHFFFAOYSA-N 1,3-dichloro-2-(4-chlorophenyl)propan-2-ol Chemical compound ClCC(O)(CCl)C1=CC=C(Cl)C=C1 UWCXGQLUAITTNP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
CICQCPXOTVUFNW-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)-3-(1h-pyrrol-2-yl)propan-2-ol Chemical class C=1C=NNC=1CC(O)CC1=CC=CN1 CICQCPXOTVUFNW-UHFFFAOYSA-N 0.000 description 1
XZUSXWMBZDIECA-UHFFFAOYSA-N 1-chloro-4-(3-methylbutyl)benzene Chemical compound CC(C)CCC1=CC=C(Cl)C=C1 XZUSXWMBZDIECA-UHFFFAOYSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
XGEGPTGOJZWONU-UHFFFAOYSA-N 2-(2-methyloxiran-2-yl)-1h-pyrrole Chemical class C=1C=CNC=1C1(C)CO1 XGEGPTGOJZWONU-UHFFFAOYSA-N 0.000 description 1
RWGAKLIRABCFDM-UHFFFAOYSA-N 2-(chloromethyl)-2-(2-chlorophenyl)oxirane Chemical compound C=1C=CC=C(Cl)C=1C1(CCl)CO1 RWGAKLIRABCFDM-UHFFFAOYSA-N 0.000 description 1
ZHGPXTMHXHRTOC-UHFFFAOYSA-N 2-(chloromethyl)-2-(4-chlorophenyl)oxirane Chemical compound C=1C=C(Cl)C=CC=1C1(CCl)CO1 ZHGPXTMHXHRTOC-UHFFFAOYSA-N 0.000 description 1
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241000235349 Ascomycota Species 0.000 description 1
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241001480061 Blumeria graminis Species 0.000 description 1
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229910021532 Calcite Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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244000060011 Cocos nucifera Species 0.000 description 1
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
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IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
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238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)

CA000547804A 1983-04-12 1987-09-24 2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides Expired CA1241658A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000547804A CA1241658A (fr)	1983-04-12	1987-09-24	2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP3313073.6		1983-04-12
DE3313073A DE3313073A1 (de)	1983-04-12	1983-04-12	1-azolyl-3-pyrazolyl-2-propanol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
CA000451607A CA1242444A (fr)	1983-04-12	1984-04-10	Derives de 1-azolyl-3-pyrazolyl-2-propanol; preparation et utilisation comme fongicides
CA000547804A CA1241658A (fr)	1983-04-12	1987-09-24	2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000451607A Division CA1242444A (fr)	1983-04-12	1984-04-10	Derives de 1-azolyl-3-pyrazolyl-2-propanol; preparation et utilisation comme fongicides

Publications (1)

Publication Number	Publication Date
CA1241658A true CA1241658A (fr)	1988-09-06

Family

ID=25670352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000547804A Expired CA1241658A (fr)	1983-04-12	1987-09-24	2-pyrazolylmethyl-oxirannes utiles comme produits intermediaires pour l'obtention de fongicides

Country Status (1)

Country	Link
CA (1)	CA1241658A (fr)

1987
- 1987-09-24 CA CA000547804A patent/CA1241658A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-09-06	MKEX	Expiry

Publication	Publication Date	Title
US4548945A (en)	1985-10-22	Fungicidally active substituted 1-hydroxyethyl-triazolyl derivatives
CA1092130A (fr)	1980-12-23	Emploi comme fongicides de derives d'acide azolyl- carboxylique
US4578396A (en)	1986-03-25	Fungicidal hydroxyalkinyl-azolyl derivatives
CA1131233A (fr)	1982-09-07	Derives acyles de 1-azolyl-2-hydroxy-butane; methodes pour les preparer et leur utilisation comme fongicides
US4587239A (en)	1986-05-06	1-azolyl-3-pyrazolyl-2-propanol fungicides
CA1187085A (fr)	1985-05-14	2-imidazolylmethyl-2-phenyl-1,3-dioxolanes; preparation et utilisation comme fongicides
CA1247110A (fr)	1988-12-20	.alpha.-ARYL-1H-AZOLE-1-ETHANOLS
NZ208847A (en)	1986-10-08	Fungicidal compositions containing diazole and triazole derivatives
CA1092129A (fr)	1980-12-23	Derives de 1-azolyl-4-hydroxy-butane; leur emploi en tant que fongicides et bactericides
CA1150279A (fr)	1983-07-19	Derives de triazolyl-alcene; methode de preparation et emploi comme fongicides
US4427673A (en)	1984-01-24	Azolylalkyl ketone and alcohol fungicides
US4472416A (en)	1984-09-18	Combating fungi with substituted azolyl-phenoxy derivatives
US4465680A (en)	1984-08-14	Combating fungi with azolylvinyldithioacetals
US4559355A (en)	1985-12-17	2-Aryl-2-azolylmethyl-1,3-dioxepine fungicides
US4818762A (en)	1989-04-04	Fungicidal novel hydroxyalkynyl-azolyl derivatives
US4396624A (en)	1983-08-02	Combating fungi with 1-(azol-1-yl)-2-hydroxy-or-keto-1-pyridinyloxy-alkanes
US4622335A (en)	1986-11-11	Fungicidal hydroxyethylazolyl-oxime derivatives
US4870092A (en)	1989-09-26	1,3-Diazolyl-2-propanols as fungicidal agents
US4500537A (en)	1985-02-19	Combating fungi with triazolyl-vinyl ketones and carbinols
CA1214469A (fr)	1986-11-25	Derives de 2-azolymethyl-1,3-dioxolane et -dioxane; preparation et utilisation comme fongicides
US4385061A (en)	1983-05-24	Combating fungi with imidazolyl-vinyl ketones and carbinols
US4428949A (en)	1984-01-31	Combating fungi with fluorinated 1-azolylbutane derivatives
US4596815A (en)	1986-06-24	Antifungal azolylmethyl-thienyl-carbinol derivatives
US4921870A (en)	1990-05-01	Fungicidal novel substituted phenethyl-triazolyl derivatives
US4360529A (en)	1982-11-23	Combating fungi with trisubstituted benzyl oxime ethers