EP0937046A2 - Substituierte 3-benzylpyrazole und ihre verwendung als herbizide und zur senkung des blutzuckergehaltes - Google Patents
Substituierte 3-benzylpyrazole und ihre verwendung als herbizide und zur senkung des blutzuckergehaltesInfo
- Publication number
- EP0937046A2 EP0937046A2 EP97948864A EP97948864A EP0937046A2 EP 0937046 A2 EP0937046 A2 EP 0937046A2 EP 97948864 A EP97948864 A EP 97948864A EP 97948864 A EP97948864 A EP 97948864A EP 0937046 A2 EP0937046 A2 EP 0937046A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- iic
- formula
- iii
- halogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- KTFGWHSLIOZEKH-UHFFFAOYSA-N 5-benzyl-1h-pyrazole Chemical class C=1C=CC=CC=1CC1=CC=NN1 KTFGWHSLIOZEKH-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 239000004009 herbicide Substances 0.000 title claims abstract description 12
- 239000008280 blood Substances 0.000 title claims abstract description 8
- 210000004369 blood Anatomy 0.000 title claims abstract description 8
- -1 methylene- Chemical class 0.000 claims abstract description 478
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 43
- 150000002367 halogens Chemical class 0.000 claims abstract description 39
- 239000000126 substance Substances 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- 230000035613 defoliation Effects 0.000 claims abstract description 14
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 14
- 239000002243 precursor Substances 0.000 claims abstract description 14
- 239000006227 byproduct Substances 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000005704 oxymethylene group Chemical class [H]C([H])([*:2])O[*:1] 0.000 claims abstract description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 119
- 239000001257 hydrogen Substances 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 20
- VGFQQHSLHWYJFB-UHFFFAOYSA-N 5-benzyl-1,2-dihydropyrazol-3-one Chemical compound N1C(O)=CC(CC=2C=CC=CC=2)=N1 VGFQQHSLHWYJFB-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 239000013543 active substance Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000002140 halogenating effect Effects 0.000 claims description 8
- PXXFHJONOGLXPU-UHFFFAOYSA-N 3-benzylpyrazole Chemical class C=1C=CC=CC=1CC1=CC=N[N]1 PXXFHJONOGLXPU-UHFFFAOYSA-N 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 239000002274 desiccant Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- PJAPXLXIEDUVSR-UHFFFAOYSA-N 5-[(2-aminophenyl)methyl]-1,2-dihydropyrazol-3-one Chemical compound NC1=CC=CC=C1CC1=CC(=O)NN1 PJAPXLXIEDUVSR-UHFFFAOYSA-N 0.000 claims description 3
- IEQSVLDUZRHYDD-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-1,2-dihydropyrazol-3-one Chemical compound ClC1=CC=CC(CC=2NNC(=O)C=2)=C1 IEQSVLDUZRHYDD-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000002837 defoliant Substances 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 claims description 2
- VWFWVBRGSXUYEB-UHFFFAOYSA-N 3-benzyl-1,5-dimethylpyrazole Chemical compound CN1C(C)=CC(CC=2C=CC=CC=2)=N1 VWFWVBRGSXUYEB-UHFFFAOYSA-N 0.000 claims description 2
- SLWCDZBRDSTRLV-UHFFFAOYSA-N 3-oxo-4-phenylbutanoic acid Chemical class OC(=O)CC(=O)CC1=CC=CC=C1 SLWCDZBRDSTRLV-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims 4
- VNOYHZYNOWVUFB-UHFFFAOYSA-N 4-benzylpyrazol-3-one Chemical class O=C1N=NC=C1CC1=CC=CC=C1 VNOYHZYNOWVUFB-UHFFFAOYSA-N 0.000 claims 1
- 239000002785 defoliant agent Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract description 5
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 40
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 241000196324 Embryophyta Species 0.000 description 27
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 11
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000008103 glucose Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000012954 diazonium Substances 0.000 description 8
- 150000001989 diazonium salts Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 244000038559 crop plants Species 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 description 6
- 210000002700 urine Anatomy 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
- 150000001345 alkine derivatives Chemical class 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 230000026030 halogenation Effects 0.000 description 5
- 238000005658 halogenation reaction Methods 0.000 description 5
- 239000003701 inert diluent Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
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- 241000219146 Gossypium Species 0.000 description 4
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- 240000002024 Gossypium herbaceum Species 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
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- 239000003112 inhibitor Substances 0.000 description 4
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- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
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- 150000003568 thioethers Chemical class 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 244000020551 Helianthus annuus Species 0.000 description 3
- 235000003222 Helianthus annuus Nutrition 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004324 thiepan-2-yl group Chemical group [H]C1([H])SC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004275 thietan-2-yl group Chemical group [H]C1([H])SC([H])(*)C1([H])[H] 0.000 description 1
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YOIAWAIKYVEKMF-UHFFFAOYSA-N trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F YOIAWAIKYVEKMF-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D231/14—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 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to new substituted 3-benzylpyrazoles of the formula I.
- R 1 are hydrogen, C 4 -alkyl, C, 4 haloalkyl, C ⁇ -C4 -Alkylsul- fonyl or C ⁇ -C4 haloalkylsulfonyl;
- R 2 C ⁇ -C -alkyl, C 4 haloalkyl, C ⁇ -C 4 -alkoxy, halo-C alkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C4-haloalkylthio, C ⁇ -C4 ⁇ alkyl - Sulfinyl, -C-C 4 haloalkylsulfinyl, C ⁇ -C 4 alkylsulfonyl or C ⁇ -C 4 haloalkylsulfonyl;
- R 3 is hydrogen, cyano, nitro, halogen, -CC 4 alkyl or C 1 -C 4 haloalkyl;
- X 1 , X 2 , X 3 , X 4 , X 5 independently of one another are a chemical bond or a methylene, ethylene, ethene-1, 2-diyl or oxymethylene or thiamethylene chain bonded to the phenyl ring via the hetero atom, where all chains can be unsubstituted or carry one or two substituents, each selected from the group consisting of cyano, halogen, C ⁇ -C 4 ⁇ alkyl and (-C-C 4 alkoxy) carbonyl;
- R, R 5 , R 6 , R 7 , R 8 independently of one another
- Cyano nitro, amino, hydroxy, carboxy, halogen, C ⁇ -C 4 -alkyl, C 4 haloalkyl, C ⁇ -C alkoxy, C -C 4 alkylthio, C ⁇ -C alkyl sulfonyl, (C ⁇ - C 4 -alkyl) carbonyl, (C ⁇ -C 4 -alkyl) carbonyloxy and (C ⁇ -C 4 -alkoxy) carbonyl, and
- R 11 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, phenyl or phenyl-C ⁇ -C 4 -alkyl stand,
- the invention relates to the use of the compounds I and their salts as herbicides and / or for the desiccation / defoliation of plants, herbicidal compositions and compositions for the desiccation and / or de-foliation of plants which the compounds I or their salts as active substances contain,
- Ila, Ilb, IIc and III or their salts contain as active substances, and
- EP-A 485 929 and WO 96/04273 for the production of angiotensin II receptor antagonists
- EP-A 420 397 JP-A 63/166 879 and JP-A 01/085 974 for the production of photochromic data carriers
- the object of the present invention was to provide new herbicidally active compounds which can be used to combat undesirable plants better than known ones.
- the up g ä be extended desiccant to the provision of new / defoliant active compounds as well as new active substances in the pharmaceutical field.
- herbicidal compositions which contain the compounds I and have a very good herbicidal action.
- processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
- the compounds I are also suitable for the desiccation / defoliation of parts of plants, for which crop plants such as cotton, potatoes, rape, sunflower,
- Soybeans or field beans, especially cotton, are suitable.
- agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with the compounds I have been found.
- compounds I In addition to their activity in the field of plant protection, compounds I, their precursors Ila, Ilb and IIc and by-products III have been found to have a pharmaceutical, in particular hypoglycemic, effect.
- One aspect of the present invention is therefore also corresponding pharmaceutical preparations.
- the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
- the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
- Haloalkyl preferably carry one to five identical or different halogen atoms.
- Halogen is fluorine, chlorine, bromine or iodine.
- C ⁇ -C 4 alkyl for: CH 3 , C 2 H 5 , CH 2 -C 2 H 5 , CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -C 2 H 5 , CH 2 -CH (CH 3 ) 2 or C (CH 3 ) 3 ;
- C ⁇ -C 4 -haloalkyl for: a C ⁇ -C 4 ⁇ alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CH 2 F, CHF, CF 3 , CH 2 C1 , CH (C1) 2 , C (C1) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2 Chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C 2 F 5 , 2-fluoropropyl, 3-fluoroprop
- C ⁇ -C 6 alkyl for: C ⁇ -C 4 alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl or l-ethyl-2-methylpropyl, preferably for CH 3 , C 2 H 5
- C ⁇ -C 6 -haloalkyl for: a C ⁇ -C 6 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the radicals mentioned under C ⁇ -C 4 -haloalkyl or for 5 - fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-penyl, undecafluoropentyl, 6 - Fluorine-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6 - iodine-1-hexyl, 6, 6, 6-trichloro-1-hexyl or dodecafluorohexyl;
- Phenyl-C ⁇ -C 4 -alkyl for: benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-l-yl, 1- phenylbut-1- yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2- yl, 4-phenylbut-2-yl, 1- (benzyl) eth-1-yl. 1- (benzyl) -1- (methyl) -eth-l-yl or 1- (benzyl) prop-1-yl, preferably for benzyl or 2-phenylethyl;
- C ⁇ -C 4 ⁇ haloalkoxy for: a C ⁇ -C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0CHF, OCHF 2 , 0CF 3 , 0CH 2 C1, OCH (Cl) 2 , 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2- Trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy,
- C ⁇ -C-Alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 , n-butylthio, 1-methylpropylthio, 2-methylpropylthio or SC (CH 3 ) 3 , preferably for SCH 3 or SCHs;
- C ⁇ -C 4 ⁇ haloalkylthio for: a C ⁇ -C 4 alkylthio radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example SCHF, SCHF 2 , SCF 3 , SCH 2 C1, SCH (C1) 2 , SC (C1) 3 , chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2,2, 2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, 2,
- C 1 -C 4 -alkoxy-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 -alkoxy - as mentioned above - substituted C ⁇ -C 4 -alkyl, for example for CH 2 -0CH 3 , CH 2 -0C 2 H 5 , n-propoxymethyl, CH 2 -0CH (CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH 2 -0C (CH 3 ) 3 , 2- (0CH 3 ) ethyl, 2- (OC 2 H 5 ) ethyl, 2- (n-propoxy) ethyl, 2- [OCH (CH 3 ) 2 ] ethyl, 2- (n-butoxy) ethyl, 2- (l-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, 2- [OC (CH 3 ) 3 ] ethyl, 2- (0CH
- C ⁇ -C 4 -haloalkoxy-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 -haloalkoxy substituted as mentioned above C ⁇ -C 4 -alkyl, for example for 2- (OCHF 2 ) ethyl, 2- (OCF 3 ) ethyl or 2- (OC 2 F 5 ) ethyl;
- C ⁇ -C 4 -alkylthio-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 ⁇ alkylthio - as mentioned above - substituted C ⁇ -C 4 -alkyl, for example for CH 2 -SCH 3 , CH 2 -SC 2 H 5 , n-propylthiomethyl, CH 2 -SCH (CH 3 ) 2 , n-butylthiomethyl, (1-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethyl, 2- (SCH 5 ) ethyl, 2- (n-propylthio) ethyl, 2- (1-methylethylthio) ethyl, 2- (n-butylthio) ethyl, 2- (1-methylpropylthio) ethyl , 2- (2-methylpropylthio) ethyl,
- C ⁇ -C 4 -haloalkylthio-C ⁇ -C 4 -alkyl for: C ⁇ -C 4 ⁇ haloalkylthio substituted as above-mentioned C ⁇ -C 4 alkyl, for example for 2- (SCHF 2 ) ethyl, 2- ( SCF 3 ) ethyl or 2- (SC 2 F 5 ) ethyl;
- CO-CH (CH 3 ) 2 n-butylcarbonyl, CO-CH (CH 3 ) -C 2 H 5 , C0-CH 2 -CH (CH 3 ) 2 or CO-C (CH 3 ) 3 , preferably for C0 -CH 3 or C0-C 2 Hs;
- (C ⁇ -C-Alkyl) carbonyloxy for: O-CO-CH 3 , 0-CO-C 2 H 5 , 0-CO-CH 2 -C 2 H 5 , 0-CO-CH (CH 3 ) 2 , 0 -CO-CH 2 -CH 2 -C 2 H 5 , 0-CO-CH (CH 3 ) -C 2 H 5 , 0-CO-CH 2 -CH (CH 3 ) 2 or O-CO-C (CH 3 ) 3 , preferably for 0-CO-CH 3 or 0-CO-C 2 H 5 ;
- (-C-C 4 -alkoxy) carbonyl for: CO-OCH 3 , CO-OC 2 H 5 , CO-OCH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH ( CH 3 ) -CH 5 , CO-OCH-CH (CH 3 ) 2 or CO-OC (CH 3 ) 3 , preferably for CO-OCH 3 or CO-OC 2 H 5 ;
- (C ⁇ -C 4 ⁇ alkoxy) carbonyl-C ⁇ -C 4 alkyl for: by (C ⁇ -C 4 ⁇ alkoxy) carbonyl - as mentioned above - substituted C -C 4 alkyl, so for example for CH 2 -CO -OCH 3 , CH 2 -CO-OC 2 H 5 , n-prop-oxycarbonyl-methyl, CH 2 -CO-OCH (CH 3 ) 2 , n-butoxycarbonylmethyl, CH 2 -CO-OCH (CH 3 ) -C 2 H 5 , CH 2 -CO-OCH 2 -CH (CH 3 ) 2 , CH 2 -CO-OC (CH 3 ) 3 , 1- (methoxycarbonyl) ethyl, 1- (ethoxycarbonyl) ethyl, l- (n- Propoxycarbonyl) ethyl, 1- (1-methylethoxycarbonyl) ethyl, 1- (n-butoxycarbon
- C ⁇ -C-alkylsulfinyl for: SO-CH 3 , SO-C 2 H 5 , SO-CH 2 -C 2 H 5 , SO-CH (CH 3 ) 2 , n-butylsulfinyl, SO-CH (CH 3 ) - C 2 H 5 , SO-CH 2 -CH (CH 3 ) 2 or SO-C (CH 3 ) 3 , preferably for SO-CH 3 or SO-CH 5 ;
- C ⁇ -C 4 -haloalkylsulfinyl for: a C ⁇ -C 4 -alkylsulfinyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example SO-CH 2 F, S0-CHF 2 , SO-CF 3 , S0-CH 2 C1, S0-CH (C1) 2 ,
- S0-C (C1) 3 chlorofluoromethylsulfinyl, dichlorofluoromethylsulfinyl, chlorodifluoromethylsulfinyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulfinyl, 2, 2, 2-trifluoroethylsulfinyl Chloro-2-fluoroethylsulfinyl, 2-chloro-2, 2-difluoroethylsulfinyl, 2, 2-dichloro-2-fluoroethylsulfinyl, 2, 2, 2-trichloroethylsulfinyl, S0-CF 5 , 2-fluoropropylsulfinyl, 3-fluoropropyl
- C -C -alkylsulfonyl for: S0 2 -CH 3 , S0 2 -C 2 H 5 , S0-CH 2 -C 2 H 5 , S0 2 -CH (CH 3 ) 2 , n-butylsulfonyl, S0 2 -CH ( CH 3 ) -C 2 H 5 , S0 2 -CH 2 -CH (CH 3 ) 2 or S0 2 -C (CH 3 ) 3 , preferably for S0 2 -CH 3 or S0-CH 5 # -
- C ⁇ -C 4 haloalkylsulfonyl for: a C ⁇ -C 4 alkylsulfonyl radical - as mentioned above - which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example S0 -CH 2 F, S0 2 -CHF 2 , S0 2 -CF 3 , S0 2 -CH 2 C1, S0 2 -CH (C1) 2 , S0 -C (C1) 3 , chlorofluoromethylsulfonyl, dichlorofluoromethylsulfonyl, chlorodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl , 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2,
- C ⁇ -C 4 ⁇ alkylsulfonyl-C ⁇ -C4-alkyl for: C ⁇ -C 4 alkylsulfonyl as mentioned above substituted C ⁇ -C 4 alkyl, for example for CH 2 S0 2 -CH 3 , CH 2 S0 2 -C 2 H 5 , CH 2 S0 2 -CH 2 -C 2 H 5 , CH 2 S0 2 -CH (CH 3 ) 2 , CH 2 S0 2 -CH 2 CH 2 -C 2 H 5 , (1-methylpropylsulfonyl) methyl, (2-methyl-propylsulfonyl) methyl, CH 2 S0 2 -C (CH 3 ) 3 , CH (CH 3 ) S0 2 -CH 3 , CH (CH 3 ) S0 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH 3 , CH 2 CH 2 S0 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH
- C ⁇ -C4-alkyl e.g. for 2- (2, 2, 2-trifluoroethylsulfonyl) ethyl;
- CO- (C 2 H 5 ) -CH (CH 3 ) 2 CO- (C 2 H 5 ) -CH 2 -C 2 H 5 , CO-N (C 2 H 5 ) -CH (CH 3 ) -C 2 H 5 , CO-N (C 2 H 5 ) -CH 2 -CH (CH 3 ) 2 , CO-N (C 2 H 5 ) -C (CH 3 ) 3 , CO-N [CH (CH 3 ) 2 ] -CH 2 -C 2 H 5 , CO-N (CH 2 -C 2 H 5 ) -CH 2 CH 2 -C 2 H 5 , CO-N (CH 2 -C 2 H 5 ) -CH (CH 3 ) -C 2 H 5 , CO-N (CH 2 -C 2 H 5 ) -CH 2 -CH (CH 3 ) 2 H 5 , CO-N (CH 2 -C 2 H 5 ) -CH 2 -CH (CH 3 ) 2 ,
- C 2 -C 6 alkenyl for: vinyl, prop-1-en-l-yl, allyl, 1-methylethenyl, 1-buten-l-yl, l-buten-2-yl, l-buten-3 -yl, 2-butene-1-yl, 1-methyl-prop-1-en-1-yl, 2-methyl-prop-1-en-1-yl, 1-methyl-prop-2-en-1 -yl, 2-methyl-prop-2-en-l-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1 -Methyl-but-l-en-l-yl, 2-methyl-but-l-en-l-yl, 3-methyl-but-1-en-l-yl, 1-methyl-but-2-ene -l-yl, 2-methyl-but-2-en- 1-yl, 3-methyl-but-2-en-l-yl, l-
- C 2 -Cg alkynyl for: ethynyl and C 3 -Cg alkynyl such as prop-1-in-1-yl, prop-2-in-1-yl, n-but-1-in-1-yl, n -But-1-in-3-yl, n-but-1-in-4-yl, n-but-2-in-1-yl, n-pent-1-in-1-yl, n-pent -l-in-3-yl, n-pent-l-in-4-yl, n-pent-l-in-5-yl, n-pent-2-in-l-yl, n-pent-2 -in-4-yl, n-pent-2-yn-5-yl, 3-methyl-but-l-yn-3-yl, 3-methylbut-l-yn-4-yl, n-hex -1-in-1-yl, n-hex-1-in-3-yl,
- C 3 -C 8 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
- C 3 -C 8 cycloalkyl which contains a carbonyl or thiocarbonyl ring member, for example for cyclobutanone-2-yl, cyclobutanone-3-yl, cyclopentanone-2-yl, cyclopentanone-3-yl, cyclohexanone-2 - yl, Cyclohexanon-4-yl, Cycloheptanon-2 -yl, Cyclooctanon-2 -yl, Cyclobutanthion-2 -yl, Cyclobutanthion-3 -yl, Cyclopentanthion-2-yl, Cyclopentanthion-3 -yl, Cyclohexanthion-2 -yl, Cyclohexanthion-4-yl, cycloheptanthion-2-yl or cyclooctanethion-2-yl, preferably for cyclopentanone-2-yl or cyclohexanone-2-yl
- 3- to 7-membered heterocyclyl is understood to mean both saturated, partially or completely unsaturated and aromatic heterocycles having one to three heteroatoms, selected from a group consisting of one to three nitrogen atoms, one or two oxygen atoms and one or two sulfur atoms.
- saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are: oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan 2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3- yl, tetra-hydrothiophene-2-yl, tetrahydrothiophene-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-di
- unsaturated heterocycles which may contain a carbonyl or thiocarbonyl ring member are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazoline-5-yl, 1,3-oxazoline 2-yl;
- heteroaromatics the 5- and 6-membered ones are preferred, e.g.
- Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-0xazolyl, 4-0xazolyl and 5-0xazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, Imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-0xadiazol-3-yl,
- 1,2,4-0xadiazol-5-yl and 1,3,4-oxadiazol-2-yl 1,2,4-0xadiazol-5-yl and 1,3,4-oxadiazol-2-yl
- thiadiazolyl such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and l, 3,4-thiadiazol-2-yl
- triazolyl such as 1,2,4-triazol-l-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl
- Pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl like
- R 1 C -C 4 alkyl or C ⁇ -C 4 ⁇ haloalkyl, especially methyl, ethyl or C ⁇ -C 2 haloalkyl, particularly preferably methyl;
- Haloalkoxy in particular, C ⁇ -C4-haloalkyl or C ⁇ -C ⁇ 4 haloalkoxy, particularly preferably trifluoromethyl, or di- fluoromethoxy; difluoromethoxy is very particularly preferred;
- R 3 cyano, nitro, halogen, C -C 4 alkyl or C ⁇ -C haloalkyl, especially halogen, particularly preferably chlorine;
- X 1 and X 2 each represent a chemical bond;
- R 4 and R 5 independently of one another halogen, in particular chlorine or bromine;
- X 5 stands for a chemical bond and R 8 for hydrogen and one of the two groups -X 3 R 6 or -X 4 R 7 denotes hydrogen which is linked to the phenyl ring via a chemical bond;
- R 9 and R 10 independently of one another are hydrogen, C ⁇ -C 6 -alkyl, C--C 6 -haloalkyl, C 2 -C 6 -alkenyl, C -C 6 -alkynyl, C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkoxy- C ⁇ -C 4 ⁇ alkyl, C ⁇ -C 4 -alkylthio-C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkylthio- C ⁇ -C 4 -alkyl, C ⁇ -C 4 ⁇ Alkylsulfonyl-C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkyl-sulfonyl-C ⁇ -C 4 -alkyl, (C ⁇ -C 4 -alkyl) carbonyl-C ⁇ -C 4 -alkyl, (C ⁇ -C 4 ⁇ alk
- C 3 -C 8 cycloalkyl which may contain a carbonyl or thiocarbonyl ring member, phenyl or 3- to 7-membered heterocyclyl, which may contain a carbonyl or thiocarbonyl ring member, each cycloalkyl, the phenyl and each heterocyclyl Ring can be unsubstituted or carry one or two substituents, each selected from the group consisting of cyano, nitro, amino, hydroxy, carboxy, halogen, C ⁇ -C 4 ⁇ alkyl, C ⁇ -C 4 ⁇ haloalkyl, C ⁇ -C 4 - Alkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C 4 ⁇ alkyl sulfonyl, (C ⁇ -C 4 alkyl) carbonyl, (C ⁇ -C 4 alkyl) carbonyloxy and (C ⁇ -C 4 ⁇ alkoxy) carbonyl.
- the compounds Ib.2 to Ib.767 which differ from the corresponding compounds Ia.2 to Ia.767 only in that the corresponding
- the variables preferably have the following meanings, each individually or in combination:
- R 1 is hydrogen, C ⁇ -C 4 alkyl or C 1 -C 4 haloalkyl, in particular hydrogen or methyl;
- R 2 C ⁇ -C 4 haloalkyl or C ⁇ -C 4 haloalkoxy, in particular dif1uormethoxy;
- R 3 is hydrogen or halogen, especially hydrogen
- R 4 and R 5 independently of one another halogen, in particular chlorine or bromine;
- X 5 represents a chemical bond and R 8 represents hydrogen and one of the two groups -X 3 R 6 or -X 4 R 7 represents hydrogen which is linked to the phenyl ring via a chemical bond;
- Ci-Cg-alkyl Ci-Cg-alkyl, C ⁇ -C 6 -haloalkyl, C -C 6 -alkenyl, C -C 6 -alkynyl, C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkyl, C ⁇ -C 4 ⁇ haloalkoxy-
- R 12 C -C 4 haloalkyl, especially difluoromethyl.
- the compounds of the formulas Ia to Id are particularly preferred, in particular
- the compounds of the formulas Ilaa to Ilah, Ilba to Ilbh and Ilca to lie are particularly preferred, in particular
- the compounds of the formulas purple to IIIn are particularly preferred, in particular
- the substituted 3-benzylpyrazoles of the formula I can be obtained in various ways, in particular by one of the following processes:
- Suitable halogenating agents are, for example, fluorine, chlorine, bromine, diethylaminosulfur trifluoride (DAST), N-chlorosuccinimide, N-bromosuccimide, sulfuryl chloride, thionyl chloride, phosgene, phosphorus trichloride, phosphorus oxychloride, phosphorus tribromide and phosphorus oxybromide.
- DAST diethylaminosulfur trifluoride
- an inert solvent / diluent for example in a hydrocarbon such as n-hexane and toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as diethyl ether, tetrahydrofuran and dioxane, an alcohol such as methanol and ethanol, one lower carboxylic acid such as acetic acid, or in an aprotic solvent such as acetonitrile.
- the reaction temperature is usually between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
- R 12 represents C -C 4 alkyl or C ⁇ -C 4 haloalkyl;
- L 1 stands for a common leaving group such as halide, methanesulfonate, toluenesulfonate (tosylate), trifluoromethanesulfonate (triflate) or 0-S0 2 -R 12 .
- the procedure is normally carried out in an inert solvent / diluent, for example in a hydrocarbon such as n-hexane and toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as diethyl ether, tetrahydrofuran and dioxane, or in an aprotic solvent such as acetonitrile, dimethylformamide and dimethyl sulfoxide .
- a hydrocarbon such as n-hexane and toluene
- a halogenated hydrocarbon such as dichloromethane
- an ether such as diethyl ether, tetrahydrofuran and dioxane
- an aprotic solvent such as acetonitrile, dimethylformamide and dimethyl sulfoxide .
- the bases include both inorganic bases, for example alkali or alkaline earth metal carbonates such as sodium carbonate, alkali or alkaline earth metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and also organic bases, for example tertiary amines such as triethylamine and 1,8-diazabicyclo [5.4.0] undec-7 -en (DBU).
- inorganic bases for example alkali or alkaline earth metal carbonates such as sodium carbonate, alkali or alkaline earth metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and also organic bases, for example tertiary amines such as triethylamine and 1,8-diazabicyclo [5.4.0] undec-7 -en (DBU).
- inorganic bases for example alkali or alkaline earth metal carbonates such as sodium carbonate, alkali or alkaline earth metal hydroxides such as sodium hydro
- the reaction temperature is usually between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
- base and alkylating agent are used in approximately equimolar amounts, based on the amount of II.
- base and / or alkylating agent in excess, up to about five times the molar amount on the amount of II.
- Process products I and III can be separated in a conventional manner, e.g. by means of distillation, extraction, crystallization or chromatography.
- the 3-benzyl-5-hydroxy-pyrazoles / pyrazolones II required as starting materials can preferably be synthesized in three stages from phenylacetic acid chlorides V, which are either known or can be prepared by processes known per se:
- V is reacted with Meldrum's acid or a Meldrum's acid derivative (VI) in the presence of a base.
- solvents / diluents and reaction temperature the information given above for reaction II + L 1 -R 12 applies.
- the base can be both inorganic, e.g. an alkali or alkaline earth metal hydroxide such as sodium hydroxide, an alkali or alkaline earth metal carbonate such as sodium carbonate, an alkali or alkaline earth metal hydrogen carbonate such as sodium hydrogen carbonate, as well as organic, e.g. a tertiary amine such as triethylamine and pyridine.
- inorganic e.g. an alkali or alkaline earth metal hydroxide such as sodium hydroxide, an alkali or alkaline earth metal carbonate such as sodium carbonate, an alkali or alkaline earth metal hydrogen carbonate such as sodium hydrogen carbonate, as well as organic, e.g. a tertiary amine such as triethylamine and pyridine.
- the Meldrum's acid or its derivative (VI) is used in an approximately equimolar amount or in excess, up to about five times the molar amount, based on the amount of V.
- phenylacetylmeldrum's acid is then reacted with an alcohol of the formula HR 13 , where R 13 is C ⁇ -C 4 -alkoxy, to give a phenylacetoacetic acid derivative IV, the alcohol preferably being used as a solvent.
- the reaction temperature is usually between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
- Solvents / diluents for example in a hydrocarbon such as n-hexane and toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether and dioxane, an alcohol such as methanol and ethanol, a lower car- bonic acid such as acetic acid, or in an aprotic solvent such as acetonitrile, dimethylformamide and dimethyl sulfoxide.
- a hydrocarbon such as n-hexane and toluene
- a halogenated hydrocarbon such as dichloromethane
- an ether such as diethyl ether, tetrahydrofuran, diethylene glycol dimethyl ether and dioxane
- an alcohol such as methanol and ethanol
- a lower car- bonic acid such as acetic acid
- an aprotic solvent such
- the reaction temperature is usually between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
- an approximately equimolar amount of hydrazine (derivative) or an excess, up to about five times the molar amount, based on the amount of IV or VII, is used.
- the base can be both inorganic, e.g. an alkali or alkaline earth metal hydroxide such as sodium hydroxide, an alkali or
- Alkaline earth metal carbonate such as sodium carbonate, an alkali or alkaline earth metal hydrogen carbonate such as sodium hydrogen carbonate, as well as organic, e.g. a tertiary amine such as triethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) and pyridine.
- a tertiary amine such as triethylamine, 1, 8-diazabicyclo [5.4.0] undec-7-ene (DBU) and pyridine.
- alkyne and base are used, based on the amount of VIII.
- An excess of alkyne and / or base up to about five times the molar amount, based on the amount of VIII, is used.
- nitration reagents used are, for example, nitric acid in different concentrations, also concentrated and fuming nitric acid, mixtures of
- the reaction can either be carried out solvent-free in an excess of the nitrating reagent or in an inert solvent or diluent, e.g. Water, mineral acids, organic acids, halogenated hydrocarbons such as methylene chloride, anhydrides such as acetic anhydride and mixtures of these solvents are suitable.
- an inert solvent or diluent e.g. Water, mineral acids, organic acids, halogenated hydrocarbons such as methylene chloride, anhydrides such as acetic anhydride and mixtures of these solvents are suitable.
- nitrating reagent are expediently used in approximately equimolar amounts; However, in order to optimize the conversion of the starting compound, it may be advantageous to use the nitrating reagent in excess, up to about ten times the molar amount. When carrying out the reaction without a solvent in the nitrating reagent, this is present in an even greater excess.
- the reaction temperature is normally from (- 100) to 200 ° C, preferably at (- 30) to 50 ° C.
- Process products I, Ha, Ilb, IIc or III with at least one nitro group on the phenyl ring can then be reduced to corresponding compounds I, Ha, Ilb, IIc or III with at least one amino group:
- the reduction can be carried out with a metal such as iron, zinc or tin under acidic reaction conditions or with a complex hydride such as lithium aluminum hydride and sodium borohydride, the solvents being - depending on the chosen reducing agent - for example water, alcohols such as methanol, ethanol and isopropanol or ether such as diethyl ether, methyl tert. butyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl ether.
- a metal such as iron, zinc or tin under acidic reaction conditions or with a complex hydride such as lithium aluminum hydride and sodium borohydride
- the solvents being - depending on the chosen reducing agent - for example water, alcohols such as methanol, ethanol and isopropanol or ether such as diethyl ether, methyl tert. butyl ether, dioxane, tetrahydrofuran and ethylene glycol dimethyl
- the process is preferably carried out in a solvent-free manner in an inorganic acid, in particular in concentrated or dilute hydrochloric acid, or in an organic acid such as acetic acid.
- an inert solvent to the acid, e.g. to mix one of the above.
- the starting compound I, Ha, Ilb, IIc or III ⁇ -X 1 R 4 , -X 2 R 5 , -X 3 R 6 , -XR 7 or -X 5 R 8 N0 2 ⁇ and the reducing agent are expediently approximately equimolar amounts used; To optimize the course of the reaction, however, it may also be advantageous to use the reducing agent in excess, up to about ten times the molar amount.
- the amount of acid is not critical.
- the reaction temperature is generally from (-30) to 200 ° C., preferably from 0 to 80 ° C.
- the reaction mixture is usually diluted with water and the product by filtration, crystallization or extraction with a solvent which is largely immiscible with water, e.g. isolated with ethyl acetate, diethyl ether or methylene chloride. If desired, the product can then be cleaned as usual.
- Suitable catalysts for this are, for example, Raney nickel, palladium on carbon, palladium oxide, platinum and platinum oxide, mean a catalyst amount of 0.05 to 10.0 mol%, based on the compound to be reduced, is sufficient.
- reaction solution can be worked up to the product in the customary manner.
- the hydrogenation can be carried out at normal pressure or under elevated pressure.
- the conversion of the diazonium salt thus obtained into the corresponding compound I, Ha, Ilb, IIc or III, each with -X i R 4 , -XR 5 , -X 3 R 6 , -X 4 R 7 or -X 5 R 8 cyano Chlorine, bromine or iodine is particularly preferably carried out by treatment with a solution or suspension of a copper (I) salt such as copper (I) cyanide, chloride, bromide and iodide, or with an alkali metal salt solution.
- a copper (I) salt such as copper (I) cyanide, chloride, bromide and iodide
- Meerwein arylation is usually the reaction of the diazonium salts with alkenes or alkynes.
- the alkene or alkyne is preferably used in excess, up to about 3000 mol%, based on the amount of the diazonium salt.
- the reactions of the diazonium salt described above can e.g. in water, in aqueous hydrochloric acid or hydrobromic acid, in a ketone such as acetone, diethyl ketone and methyl ethyl ketone, in a nitrile such as acetonitrile, in an ether such as dioxane and tetrahydrofuran or in an alcohol such as methanol and ethanol.
- reaction temperatures are normally from (- 30) to + 50 ° C. All reactants are preferably used in approximately stoichiometric amounts, but an excess of one or the other component, up to approximately 3000 mol%, can also be advantageous.
- Useful reducing agents are e.g. Transition metals such as iron, zinc and tin (see, for example, "The Chemistry of the Thiol Group", John Wiley, 1974, p. 216).
- Halosulfonation can be carried out in one solvent
- Excess sulfonating reagent or in an inert solvent / diluent e.g. in a halogenated hydrocarbon, an ether, an alkyl nitrile or a mineral acid.
- Chlorosulfonic acid is both the preferred reagent and solvent.
- the reaction temperature is usually between 0 ° C and the boiling point of the reaction mixture.
- the reaction mixture is mixed with water, for example, after which the product can be isolated as usual.
- Suitable solvents are organic acids, inorganic acids, aliphatic or aromatic hydrocarbons, which can be halogenated, and ethers, sulfides, sulfoxides and sulfones.
- halogenating agents are chlorine, bromine, N-bromosuccinimide, N-chlorosuccinimide or sulfuryl chloride.
- a radical initiator for example an organic peroxide such as dibenzoyl peroxide or an azo compound such as azobisisobutyronitrile, or irradiation with light can have an advantageous effect on the course of the reaction.
- a catalytic amount is usually sufficient.
- the reaction temperature is normally from (- 100) to 200 ° C, especially at 10 to 100 ° C or the boiling point of the reaction mixture.
- Alcohols, thiols, carboxylic acids or amines in which case it is preferably carried out in the presence of a base (for example an alkali metal or alkaline earth metal hydroxide or an alkali metal or alkaline earth metal carbonate), or the reaction is carried out by reacting the alcohols, thiols, carboxylic acids or amines with one Base (eg an alkali metal hydride) obtained alkali metal salts of these compounds.
- a base for example an alkali metal or alkaline earth metal hydroxide or an alkali metal or alkaline earth metal carbonate
- Base eg an alkali metal hydride
- Aprotic organic solvents e.g. Tetrahydrofuran, dimethylformamide, dimethyl sulfoxide, or hydrocarbons such as toluene and n-hexane.
- the reaction is carried out at a temperature between the melting point and the boiling point of the reaction mixture, preferably at 0 to 100 ° C.
- the reaction temperature is usually 0 to 120 ° C.
- Dimethyl sulfoxide for example, is suitable as a solvent.
- Ethene-1,2-diyl ⁇ The olefination is preferably carried out using the Wittig method or one of its modifications, phosphorylides, phosphonium salts and phosphates being used as reactants, or by aldol condensation.
- alkali metal alkyls such as n-butyllithium
- alkali metal hydrides and alcoholates such as sodium hydride, sodium ethanolate and potassium tert. -butanolate
- alkali metal and alkaline earth metal hydroxides such as calcium hydroxide
- reaction temperature is (-40) to 150 ° C.
- phosphonium salts, phosphonates or phosphorylides required as reactants are known or can be prepared in a manner known per se ⁇ cf. see, for example, Houben-Weyl, Methods of Organic Chemistry, Vol. El, pp. 636ff. and Vol. E2, pp. 345ff., Georg Thieme Verlag Stuttgart 1982; Chem. Ber. __ . , 3993 (1962) ⁇ .
- reaction mixtures are generally worked up in a manner known per se. Unless stated otherwise in the processes described above, the valuable products are obtained e.g. after dilution of the reaction solution with water by filtration, crystallization or solvent extraction, or by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase onto the product.
- Both the substituted 3-benzylpyrazoles I and the 3-benzyl -5-hydroxypyrazoles Ha and the pyrazolones Ilb, IIc and III can be obtained in the preparation as isomer mixtures, which, however, if desired according to the usual methods such as crystallization or chromatography, also on one optically active adsorbate into which largely pure isomers can be separated. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
- Agricultural salts of the compounds I or physiologically acceptable salts of the compounds I, Ha, Ilb, IIc and III can be obtained by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably that Hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid are formed.
- a base of the corresponding cation preferably an alkali metal hydroxide or hydride
- an acid of the corresponding anion preferably that Hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid are formed.
- Salts of I, Ha, Ilb, Hc or III can also be prepared in a conventional manner by salting over the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, Sulfonium or sulfoxonium hydroxides.
- the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
- the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
- the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
- the following crops are considered, for example:
- the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
- the substituted 3-benzylpyrazoles I are also suitable for the desiccation and / or defoliation of plants.
- desiccants are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.
- the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
- the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
- mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
- mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives,
- Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
- the substrates as such or dissolved in an oil or solvent, by means of wetting agents, adhesives, dispersants or emulsifiers in water be homogenized.
- concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
- alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl poly
- Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
- Solid carriers are mineral soils such as silica, silica gels, silicates, talc, kaolin, limestone, lime,
- the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
- the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient I.
- the active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
- the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
- the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
- the substituted 3-benzylpyrazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
- substituted 3-benzylpyrazoles I their precursors Ha, Ilb and IIc, the by-products III and the physiologically tolerable salts of all these compounds are suitable - both as isomer mixtures and in the form of the pure isomers - as active pharmaceutical ingredients, in particular for lowering the blood sugar Salary.
- the compounds, I, Ha, Ilb, IIc and III can be in free form or in the form of a salt with a physiologically compatible acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, malonic acid, succinic acid, fumaric acid, maleic acid, citric acid, tartaric acid, lactic acid and oxalic acid can be administered orally, parenterally or intravenously.
- a physiologically compatible acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, malonic acid, succinic acid, fumaric acid, maleic acid, citric acid, tartaric acid, lactic acid and oxalic acid can be administered orally, parenterally or intravenously.
- the daily dose of active substance is between 0.01 and 25, preferably between 0.1 and 20, in particular between 1 and 10 mg / kg of body weight in the case of oral, and between 0.5 and 5, preferably between 1 and 3 mg / kg body weight with intravenous use.
- the compounds, I, Ha, Ilb, IIc and III can be used in the customary pharmaceutical application forms in solid or liquid form, for example as tablets, film-coated tablets, coated tablets, capsules. be pills, powders, solutions or suspensions, infusion or injection solutions as well as pastes, ointments, gels, creams, lotions, powders, emulsions and sprays.
- the active ingredients can be processed with the usual pharmaceutical auxiliaries such as tablet binders, fillers, plasticizers, wetting agents, dispersants, emulsifiers, solvents, retardants and / or antioxidants (cf. H. Sucker et al., Pharmaceutical Technology, Thieme Verlag Stuttgart 1978 ).
- the preparations thus obtained normally contain the active ingredient in an amount of 0.1 to 99% by weight.
- Precursor 1 4- (2, 3-dichlorophenyl) -3-oxobutyric acid methyl ester
- Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
- the seeds of the test plants were sown separately according to species.
- the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
- the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
- test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
- the application rate for post-emergence treatment was 0.125 kg / ha aS (active substance).
- the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
- the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
- Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
- the plants used in the greenhouse experiments are composed of the following types:
- the young cotton plants were treated to runoff with aqueous preparations of the active compounds (with the addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac LF 700 X based on the spray mixture).
- the amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.
- Homozygous diabetes mice (40-60 g, from Harlan UK) were used as experimental animals, which were initially not fed for one night and then divided into different groups.
- the active substances were administered by gavage as a solution or suspension in 0.25% aqueous hydroxyethyl cellulose (CELLOSIZE from UCC), namely 5 ml / kg live weight.
- CELLOSIZE aqueous hydroxyethyl cellulose
- the compounds Icl, IHcl and Ia.l reduced the plasma glucose content by approx. 20-60%, whereby the plasma insulin level remained largely unchanged.
- mice received 0.25% aqueous Cellosize without active ingredient.
- the urine was then collected for 24 hours and its total volume measured. Each 10 ⁇ l urine was examined for its glucose content. In the 10 mice to which Cellosize had been administered without active ingredient, the total amount of urine after 24 hours was 9.0 ml, with a glucose concentration of 5.15 mmol / l. This corresponds to a total excretion of glucose of 46.35 ⁇ mol.
- Compound No. IHcl thus increased the excretion of glucose (via the urine) in CD1 mice by 52%.
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- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19645313A DE19645313A1 (de) | 1996-11-04 | 1996-11-04 | Substituierte 3-Benzylpyrazole |
DE19645313 | 1996-11-04 | ||
PCT/EP1997/006057 WO1998020000A2 (de) | 1996-11-04 | 1997-11-03 | Substituierte 3-benzylpyrazole und ihre verwendung als herbizide und zur senkung des blutzuckergehaltes |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0937046A2 true EP0937046A2 (de) | 1999-08-25 |
Family
ID=7810545
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP97948864A Withdrawn EP0937046A2 (de) | 1996-11-04 | 1997-11-03 | Substituierte 3-benzylpyrazole und ihre verwendung als herbizide und zur senkung des blutzuckergehaltes |
Country Status (7)
Country | Link |
---|---|
US (1) | US6451734B1 (ja) |
EP (1) | EP0937046A2 (ja) |
JP (1) | JP2001503421A (ja) |
AU (1) | AU7001798A (ja) |
CA (1) | CA2270545A1 (ja) |
DE (1) | DE19645313A1 (ja) |
WO (1) | WO1998020000A2 (ja) |
Families Citing this family (2)
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JP2012509885A (ja) * | 2008-11-21 | 2012-04-26 | グラクソスミスクライン エルエルシー | 化学プロセス |
WO2010127067A1 (en) * | 2009-04-30 | 2010-11-04 | Glaxosmithkline Llc | Chemical process |
Family Cites Families (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1261124B (de) | 1961-09-22 | 1968-02-15 | Hoechst Ag | Verfahren zur Herstellung von Pyrazolen |
DE1210431B (de) | 1961-09-22 | 1966-02-10 | Hoechst Ag | Verfahren zur Herstellung von Pyrazolen |
US3966954A (en) | 1973-09-21 | 1976-06-29 | American Cyanamid Company | 3,5-Cycloalkyl pyrazolium salts as fungicides |
IL45377A (en) * | 1973-09-21 | 1979-11-30 | American Cyanamid Co | 1,2-dimethyl-3,5-disubstituted pyrazolium salts and their use in the control of undesirable plants |
DE2409753A1 (de) * | 1974-03-01 | 1975-09-11 | Basf Ag | Substituierte pyrazole |
DE2829289A1 (de) * | 1978-07-04 | 1980-01-24 | Basf Ag | Pyrazolaetherderivate |
DE2922591A1 (de) | 1979-06-02 | 1980-12-04 | Basf Ag | Verfahren zur herstellung von pyrazolen |
DE3029160A1 (de) | 1980-08-01 | 1982-03-04 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolen |
ZA826213B (en) * | 1981-08-31 | 1983-07-27 | Uniroyal Inc | Substituted pyrazole herbicides |
US4954164A (en) | 1982-02-27 | 1990-09-04 | Nissan Chemical Industries, Ltd. | Pyrazolesulfonylurea derivatives, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof |
DE3209148A1 (de) | 1982-03-13 | 1983-09-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von pyrazolen durch katalytische dehydrierung von pyrazolinen |
GB2124211B (en) | 1982-06-25 | 1985-12-24 | Zyma Sa | Dithio compounds pharmaceutical preparations containing them and their use |
JO1410B1 (en) | 1984-11-03 | 1986-11-30 | سميث كلاين اند فرينش لابوراتوريز ليمتد | Vehicles |
ATE67493T1 (de) | 1985-02-04 | 1991-10-15 | Bayer Agrochem Kk | Heterocyclische verbindungen. |
US4649025A (en) | 1985-09-16 | 1987-03-10 | W. R. Grace & Co. | Anti-corrosion composition |
EP0230110A1 (en) | 1985-11-30 | 1987-07-29 | FISONS plc | Pharmacologically active pyrrole and pyrazole derivatives |
JPS63112566A (ja) | 1986-10-28 | 1988-05-17 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
JPS63166879A (ja) | 1986-12-27 | 1988-07-11 | Yamaha Corp | フルギド系フオトクロミツク化合物 |
IL84944A (en) | 1987-01-19 | 1992-02-16 | Ici Plc | Pharmaceutical compositions containing 1,2-dihydro-3h-indazolone derivatives,some new such compounds and their preparation |
US4877881A (en) | 1987-04-06 | 1989-10-31 | Warner-Lambert Company | Process of preparing pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxygenase inhibitors |
DE3716293A1 (de) | 1987-05-15 | 1988-11-24 | Basf Ag | Verfahren zur herstellung von pyrazolen |
JPH078866B2 (ja) | 1987-06-04 | 1995-02-01 | 東レ株式会社 | ホトクロミック性ピラゾリルフルギド化合物 |
CH671143A5 (ja) | 1987-06-09 | 1989-08-15 | Nestle Sa | |
US4906643A (en) | 1987-07-17 | 1990-03-06 | Janssen Pharmaceutica N.V. | Substituted N-(3-hydroxy-4-piperidinyl)benzamides as gastrointestinal agents |
DE3724035A1 (de) | 1987-07-21 | 1989-02-02 | Basf Ag | Verfahren zur herstellung von acylierten imidazolen und pyrazolen |
EP0300688A1 (en) | 1987-07-21 | 1989-01-25 | FISONS plc | Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them |
AT389106B (de) | 1987-10-08 | 1989-10-25 | Warner Lambert Co | Neue styrylpyrazole, isoxazole und analoge davon, welche als 5-lipoxygenaseinhibitoren wirksam sind,sowie diese verbindungen enthaltende pharmazeutische zusammensetzungen |
JPH01190670A (ja) | 1988-01-22 | 1989-07-31 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
US4925901A (en) | 1988-02-12 | 1990-05-15 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic hydroxyl-containing compounds |
DE3830238A1 (de) | 1988-09-06 | 1990-03-15 | Bayer Ag | Verfahren zur herstellung von 1-substituierten 2-(nitroimino)-1,3-diazacycloalkan-derivaten |
DE3834860A1 (de) | 1988-10-13 | 1990-04-19 | Basf Ag | Heterocyclisch substituierte alkoxycumarine, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
DE3905948A1 (de) | 1989-02-25 | 1990-08-30 | Basf Ag | Substituierte n-hydroxypyrazole und fungizide, die diese verbindungen enthalten |
DE3918979A1 (de) | 1989-06-10 | 1990-12-13 | Basf Ag | Verfahren zur herstellung von pyrazol und dessen derivaten |
EP0420397B1 (en) | 1989-07-28 | 1995-11-29 | Wako Pure Chemical Industries Ltd | Fulgimide derivatives |
WO1991002731A1 (de) | 1989-08-19 | 1991-03-07 | Boehringer Ingelheim Kg | Substituierte n-heterocyclen, ihre herstellung und verwendung |
DE3927483A1 (de) | 1989-08-19 | 1991-02-21 | Boehringer Ingelheim Kg | Neue substituierte heterocyclische fuenfringe, ihre herstellung und verwendung |
ZA9010460B (en) | 1989-12-29 | 1992-11-25 | Univ Technologies Int | Methods for modelling tertiary structures of biologically active ligands including agonists and antagonists thereto and novel synthetic antagonists based on angiotensin |
WO1991010662A1 (en) | 1990-01-12 | 1991-07-25 | Rhone-Poulenc Rorer S.A. | 2-substituted 4,5-diphenyl-imidazoles |
DE4023215A1 (de) | 1990-07-21 | 1992-01-23 | Hoechst Ag | Substituierte azole, verfahren zu deren herstellung, sie enthaltende mittel und deren verwendung |
DE4036645A1 (de) | 1990-11-16 | 1992-05-21 | Hoechst Ag | Substituierte azole, verfahren zu deren herstellung, deren enthaltende mittel und deren verwendung |
US5431635A (en) | 1990-12-18 | 1995-07-11 | Yoon; Inbae | Safety penetrating instrument having a triggered safety member for establishing an endoscopic portal in an anatomical cavity wall |
DE4103382A1 (de) | 1991-02-05 | 1992-08-06 | Basf Ag | Cyclopropancarbonsaeureamide und -thioamide, verfahren und zwischenprodukte zu ihrer herstellung sowie ihre verwendung zur schaedlingsbekaempfung |
JPH04334358A (ja) | 1991-05-02 | 1992-11-20 | Ono Pharmaceut Co Ltd | 縮合ベンゼンオキシ酢酸誘導体 |
GB9115190D0 (en) | 1991-07-12 | 1991-08-28 | Rhone Poulenc Rorer Ltd | New compositions of matter |
US5378607A (en) | 1991-07-29 | 1995-01-03 | Biomide Investment Limited Partnership | Method for testing for the presence of metastatic tumor cells |
JP3121061B2 (ja) | 1991-10-04 | 2000-12-25 | 塩野義製薬株式会社 | アルコキシイミノアセトアミド類製造用中間体の製造法およびそれに用いる中間体 |
US5258551A (en) | 1991-12-18 | 1993-11-02 | Shionogi & Co., Ltd. | Process for producing α-ketoamide derivative |
US5194435A (en) | 1992-04-07 | 1993-03-16 | American Home Products Corporation | 4-arylmethyl-5-alkyl-3h-pyrazol-3-ones |
US5183825A (en) | 1992-04-07 | 1993-02-02 | American Home Products Corporation | 4-arylmethyl-5-alkyl-3H-pyrazol-3-ones and hypoglycemic use |
US5274111A (en) * | 1992-04-07 | 1993-12-28 | American Home Products Corporation | Trifluoromethyl substituted 1H-pyrazoles and derivatives thereof |
DE4225053A1 (de) | 1992-07-29 | 1994-02-03 | Basf Ag | Verfahren zur Herstellung von 4-Dialkoxymethylpyrazolen |
DE59407859D1 (de) | 1993-06-08 | 1999-04-08 | Basf Ag | Verfahren zur Herstellung von N-substituierten Pyrazolen |
JPH06345728A (ja) | 1993-06-11 | 1994-12-20 | Nissan Chem Ind Ltd | N−置換アゾール誘導体の製造方法 |
SE9302332D0 (sv) | 1993-07-06 | 1993-07-06 | Ab Astra | New compounds |
US5391541A (en) | 1993-08-11 | 1995-02-21 | Fmc Corporation | Herbicidal 3-(substituted-benzyl)-1-methyl-6-trifluoromethyluracils |
DE4328228A1 (de) | 1993-08-23 | 1995-03-02 | Basf Ag | Verfahren zur Herstellung von Pyrazol und dessen Derivaten |
US5591776A (en) | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
ES2105939B1 (es) | 1994-08-02 | 1998-07-01 | Uriach & Cia Sa J | Nuevos pirazoles con actividad antagonista de la angiotensina ii. |
FR2725988B1 (fr) | 1994-10-24 | 1997-01-24 | Roussel Uclaf | Nouveaux derives de pyrazolones et pyrazoles acides, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant |
GB9422667D0 (en) | 1994-11-10 | 1995-01-04 | Zeneca Ltd | Herbicides |
DE4446194A1 (de) | 1994-12-23 | 1996-06-27 | Basf Ag | Verwendung von Pyrazolderivaten mit hydrophoben Resten als Nitrifikationsinhibitoren |
FR2729142A1 (fr) | 1995-01-06 | 1996-07-12 | Smithkline Beecham Lab | Nouvelles amines heterocycliques, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu'agents anti-arythmiques |
DE19523372A1 (de) | 1995-06-29 | 1997-01-09 | Basf Ag | Neue 1-Amino-3-benzyluracile |
DE19612032A1 (de) | 1996-03-27 | 1997-10-09 | Basf Ag | Substituierte 1-Methyl-3-benzyluracile |
-
1996
- 1996-11-04 DE DE19645313A patent/DE19645313A1/de not_active Withdrawn
-
1997
- 1997-11-03 WO PCT/EP1997/006057 patent/WO1998020000A2/de not_active Application Discontinuation
- 1997-11-03 AU AU70017/98A patent/AU7001798A/en not_active Abandoned
- 1997-11-03 US US09/297,529 patent/US6451734B1/en not_active Expired - Fee Related
- 1997-11-03 EP EP97948864A patent/EP0937046A2/de not_active Withdrawn
- 1997-11-03 JP JP52103998A patent/JP2001503421A/ja active Pending
- 1997-11-03 CA CA002270545A patent/CA2270545A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO9820000A2 * |
Also Published As
Publication number | Publication date |
---|---|
AU7001798A (en) | 1998-05-29 |
WO1998020000A2 (de) | 1998-05-14 |
JP2001503421A (ja) | 2001-03-13 |
US6451734B1 (en) | 2002-09-17 |
CA2270545A1 (en) | 1998-05-14 |
WO1998020000A3 (de) | 1998-10-29 |
DE19645313A1 (de) | 1998-05-07 |
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