SK7482001A3 - 3-(heterocyclyl)-benzoylpyrazole-derivatives - Google Patents

3-(heterocyclyl)-benzoylpyrazole-derivatives Download PDF

Info

Publication number: SK7482001A3
Authority: SK; Slovakia
Prior art keywords: formula; alkyl; nch; group; heterocyclyl
Prior art date: 1998-12-04

Application number

SK748-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Ulf Neidlein

Norbert Gotz

Ulf Misslitz

Roland Gotz

Ernst Baumann

Deyn Wolfgang Von

Steffen Kudis

Klaus Langemann

Guido Mayer

Matthias Witschel

Martina Otten

Karl-Otto Westphalen

Helmut Walter

Original Assignee

Basf 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.)

1998-12-04

Filing date

1999-12-02

Publication date

2001-12-03

1999-12-02 Application filed by Basf Ag filed Critical Basf Ag

2001-12-03 Publication of SK7482001A3 publication Critical patent/SK7482001A3/sk

Links

-1 halogenalkylthio Chemical group 0.000 claims abstract description 251
150000001875 compounds Chemical class 0.000 claims abstract description 130
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 38
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
239000001257 hydrogen Substances 0.000 claims abstract description 35
229910052736 halogen Inorganic materials 0.000 claims abstract description 34
150000002367 halogens Chemical class 0.000 claims abstract description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 17
150000002431 hydrogen Chemical class 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 37
125000000623 heterocyclic group Chemical group 0.000 claims description 36
UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 claims description 32
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
239000002585 base Substances 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 11
125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
235000010233 benzoic acid Nutrition 0.000 claims description 6
238000005917 acylation reaction Methods 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
230000008707 rearrangement Effects 0.000 claims description 5
239000005711 Benzoic acid Substances 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 4
150000001559 benzoic acids Chemical class 0.000 claims description 4
239000004009 herbicide Substances 0.000 claims description 4
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 10
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 7
125000004438 haloalkoxy group Chemical group 0.000 abstract description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 5
125000001188 haloalkyl group Chemical group 0.000 abstract description 5
125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract description 2
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 abstract description 2
150000001350 alkyl halides Chemical class 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
239000000460 chlorine Substances 0.000 description 46
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
229910052801 chlorine Inorganic materials 0.000 description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 20
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 20
229910052794 bromium Inorganic materials 0.000 description 20
241000196324 Embryophyta Species 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
239000002253 acid Substances 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
239000011737 fluorine Substances 0.000 description 12
230000002363 herbicidal effect Effects 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
239000002904 solvent Substances 0.000 description 11
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
125000004441 haloalkylsulfonyl group Chemical group 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
150000002940 palladium Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
229910000288 alkali metal carbonate Chemical group 0.000 description 7
150000008041 alkali metal carbonates Chemical group 0.000 description 7
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
239000003446 ligand Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
239000004359 castor oil Substances 0.000 description 6
235000019438 castor oil Nutrition 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
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 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
125000006125 ethylsulfonyl group Chemical group 0.000 description 5
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
238000011065 in-situ storage Methods 0.000 description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000243 solution Substances 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000007859 condensation product Substances 0.000 description 4
230000006378 damage Effects 0.000 description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
238000010410 dusting Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
235000012054 meals Nutrition 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000287828 Gallus gallus Species 0.000 description 3
244000060234 Gmelina philippensis Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
150000008051 alkyl sulfates Chemical class 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
235000011920 black pudding Nutrition 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000005997 bromomethyl group Chemical group 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
230000012010 growth Effects 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
150000002923 oximes Chemical class 0.000 description 3
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
239000006072 paste Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
150000003217 pyrazoles Chemical class 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
241000894007 species Species 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
244000140786 Brassica hirta Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
241000209504 Poaceae Species 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
240000006394 Sorghum bicolor Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000002411 adverse Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000003973 alkyl amines Chemical group 0.000 description 2
150000005215 alkyl ethers Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
230000035784 germination Effects 0.000 description 2
125000004995 haloalkylthio group Chemical group 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
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229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
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LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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150000003456 sulfonamides Chemical class 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
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239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 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
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK748-2001A 1998-12-04 1999-12-02 3-(heterocyclyl)-benzoylpyrazole-derivatives SK7482001A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19855850		1998-12-04
DE19936705		1999-08-06
PCT/EP1999/009412 WO2000034272A2 (de)	1998-12-04	1999-12-02	3-(heterocyclyl)-benzoylpyrazol-derivate

Publications (1)

Publication Number	Publication Date
SK7482001A3 true SK7482001A3 (en)	2001-12-03

Family

ID=26050548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK748-2001A SK7482001A3 (en)	1998-12-04	1999-12-02	3-(heterocyclyl)-benzoylpyrazole-derivatives

Country Status (20)

Country	Link
US (1)	US6506708B1 (cs)
EP (1)	EP1135387B1 (cs)
JP (1)	JP2002531561A (cs)
KR (1)	KR20010081058A (cs)
CN (1)	CN1332739A (cs)
AT (1)	ATE227285T1 (cs)
AU (1)	AU1779700A (cs)
BG (1)	BG105634A (cs)
BR (1)	BR9915949A (cs)
CA (1)	CA2353573A1 (cs)
CZ (1)	CZ20011961A3 (cs)
DE (1)	DE59903358D1 (cs)
DK (1)	DK1135387T3 (cs)
EA (1)	EA200100601A1 (cs)
ES (1)	ES2188278T3 (cs)
HU (1)	HUP0200072A3 (cs)
IL (1)	IL143450A0 (cs)
PL (1)	PL348885A1 (cs)
SK (1)	SK7482001A3 (cs)
WO (1)	WO2000034272A2 (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GEP20022617B (en) *	1997-01-17	2002-01-25	Basf Ag	3-Heterocyclic YL-Substituted Benzoyl Derivatives, Method for Their Production, Herbicidal Preparation and Method for Undesirable Plants Control
EP1286991B1 (de)	1999-12-02	2007-06-06	Basf Aktiengesellschaft	Cyclopropyl-anellierte 3-(4,5-dihydroisoxazol-3-yl)-substituierte benzoylpyrazole als herbizide
BR0016086A (pt) *	1999-12-02	2002-08-06	Basf Ag	Benzoilpirazol 3-(4,5-diidroisoxazol-3-il) substituìdo, processo para preparar benzoilpirazóis 3-(4,5-diidroisoxazol-3-il) substituìdos, composto, composição, processo para a preparação de composição, método para controlar vegetação indesejável, e, uso dos benzolpirazóis 3-(4,5-diidroisoxazol-3-il) - substituìdos da fórmula i e/ou de seus sais agricolamente úteis
AR032779A1 (es) *	2000-12-11	2003-11-26	Basf Ag	Derivados de ciclohexenona de benzazolonas, acidos benzazolonacarboxilicos, agentes que contienen por lo menos un derivado de ciclohexenona, procedimiento para combatir el crecimiento indeseado de plantas y uso de dichos derivados como herbicidas
CN121449596A (zh) *	2025-11-28	2026-02-03	山东诚创蓝海医药科技有限公司	用于水稻田顽固抗性杂草防治的苯唑草酮衍生物及其应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR19980702466A (ko)	1995-02-24	1998-07-15	페라 스타르크, 요헨 카르크	피라졸-4-일-벤조일 유도체 및 제초제로서의 그의 용도
US6165944A (en)	1997-01-17	2000-12-26	Basf Aktiengesellschaft	4-(3-heterocyclyl-1-benzoyl) pyrazoles and their use as herbicides
GEP20022617B (en)	1997-01-17	2002-01-25	Basf Ag	3-Heterocyclic YL-Substituted Benzoyl Derivatives, Method for Their Production, Herbicidal Preparation and Method for Undesirable Plants Control
DE69839310T3 (de)	1997-10-30	2015-08-06	Nippon Soda Co. Ltd.	Verwendung einer benzoylpyrazol-verbindung als herbizid.

1999
- 1999-12-02 AU AU17797/00A patent/AU1779700A/en not_active Abandoned
- 1999-12-02 WO PCT/EP1999/009412 patent/WO2000034272A2/de not_active Ceased
- 1999-12-02 IL IL14345099A patent/IL143450A0/xx unknown
- 1999-12-02 CN CN99815253A patent/CN1332739A/zh active Pending
- 1999-12-02 CA CA002353573A patent/CA2353573A1/en not_active Abandoned
- 1999-12-02 BR BR9915949-0A patent/BR9915949A/pt not_active IP Right Cessation
- 1999-12-02 DK DK99961051T patent/DK1135387T3/da active
- 1999-12-02 PL PL99348885A patent/PL348885A1/xx not_active Application Discontinuation
- 1999-12-02 KR KR1020017006922A patent/KR20010081058A/ko not_active Withdrawn
- 1999-12-02 HU HU0200072A patent/HUP0200072A3/hu unknown
- 1999-12-02 US US09/857,034 patent/US6506708B1/en not_active Expired - Fee Related
- 1999-12-02 CZ CZ20011961A patent/CZ20011961A3/cs unknown
- 1999-12-02 SK SK748-2001A patent/SK7482001A3/sk unknown
- 1999-12-02 JP JP2000586719A patent/JP2002531561A/ja not_active Withdrawn
- 1999-12-02 EP EP99961051A patent/EP1135387B1/de not_active Expired - Lifetime
- 1999-12-02 EA EA200100601A patent/EA200100601A1/ru unknown
- 1999-12-02 DE DE59903358T patent/DE59903358D1/de not_active Expired - Lifetime
- 1999-12-02 AT AT99961051T patent/ATE227285T1/de not_active IP Right Cessation
- 1999-12-02 ES ES99961051T patent/ES2188278T3/es not_active Expired - Lifetime
2001
- 2001-06-20 BG BG105634A patent/BG105634A/xx unknown

Also Published As

Publication number	Publication date
EA200100601A1 (ru)	2001-10-22
US6506708B1 (en)	2003-01-14
PL348885A1 (en)	2002-06-17
ATE227285T1 (de)	2002-11-15
EP1135387B1 (de)	2002-11-06
BR9915949A (pt)	2001-08-21
JP2002531561A (ja)	2002-09-24
CZ20011961A3 (cs)	2002-02-13
ES2188278T3 (es)	2003-06-16
EP1135387A2 (de)	2001-09-26
CA2353573A1 (en)	2000-06-15
WO2000034272A3 (de)	2000-11-02
DK1135387T3 (da)	2002-11-25
HUP0200072A3 (en)	2004-05-28
HUP0200072A2 (hu)	2002-05-29
IL143450A0 (en)	2002-04-21
KR20010081058A (ko)	2001-08-25
DE59903358D1 (de)	2002-12-12
CN1332739A (zh)	2002-01-23
AU1779700A (en)	2000-06-26
WO2000034272A2 (de)	2000-06-15
BG105634A (en)	2002-01-31

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AU2004203481A1 (en)	2004-08-26	3-Heterocyclyl-substituted benzoyl derivatives
US6831039B1 (en)	2004-12-14	3-(heterocyclyl)-substituted benzolpyrazols
US6713436B1 (en)	2004-03-30	1-cycloalkylpyrazolyl-benzoyl derivatives
US6506708B1 (en)	2003-01-14	3-(heterocyclyl)-benzoylpyrazole-derivatives
SK8782002A3 (en)	2002-10-08	3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazoles
KR100523311B1 (ko)	2005-10-24	치환된 4-벤조일-피라졸
US6613719B1 (en)	2003-09-02	3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles
US6627581B1 (en)	2003-09-30	Cyclopropyl-anellated 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles
US6107254A (en)	2000-08-22	5-(Dioxabicyclohept-6-yl)-cyclohexenone oxime ethers, and the preparation and thereof use
DE19936520A1 (de)	2001-02-15	3-(Heterocyclyl)-benzoylpyrazolyl-Derivate
MXPA01005666A (en)	2002-05-09	Sizing composition
MXPA01005566A (en)	2001-12-04	3-(heterocyclyl)-benzoylpyrazole-derivatives
MXPA01005567A (en)	2001-12-04	3-(heterocyclyl)-substituted benzoylpyrazols