ZA200105477B - 3-(heterocyclyl)-substituted benzoylpyrazols. - Google Patents
3-(heterocyclyl)-substituted benzoylpyrazols. Download PDFInfo
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- ZA200105477B ZA200105477B ZA200105477A ZA200105477A ZA200105477B ZA 200105477 B ZA200105477 B ZA 200105477B ZA 200105477 A ZA200105477 A ZA 200105477A ZA 200105477 A ZA200105477 A ZA 200105477A ZA 200105477 B ZA200105477 B ZA 200105477B
- Authority
- ZA
- South Africa
- Prior art keywords
- formula
- compound
- alkyl
- heterocyclyl
- substituted
- Prior art date
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- 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 title claims description 19
- -1 phenylsulfonyloxy Chemical group 0.000 claims description 181
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000011814 protection agent Substances 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000006150 1,1,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004711 1,1-dimethylethylthio group Chemical group CC(C)(S*)C 0.000 description 1
- 125000006133 1,1-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000006151 1,2,2-trimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006143 1,2-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000006134 1,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000006144 1,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 1
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- 125000006135 2,2-dimethylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000006146 2,3-dimethylbutyl sulfonyl group Chemical group 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006149 2-ethylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000006131 2-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000006139 2-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000006128 2-methylpropyl sulfonyl group Chemical group 0.000 description 1
- 125000004710 2-methylpropylthio group Chemical group CC(CS*)C 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006132 3-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006140 3-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000006141 4-methylpentyl sulfonyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002409 penten-3-yl group Chemical group C=CC(CC)* 0.000 description 1
- 125000002262 penten-4-yl group Chemical group C=CCC(C)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000005537 sulfoxonium group Chemical group 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
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
Description
. 0050/50555 + C . é 20015477 3-(Heterocyclyl)-substituted benzoylpyrazoles
The present invention relates to 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I 1 X R? 0 R N-
R11 | R3
R4 [I RS I
N~n 7 RS wd owe where:
X is O, NH or N(C;-Cg-alkyl);
Rl is C;-Cg¢-alkyl;
R2,R3,R%,R% are hydrogen, C;-C4-alkyl or C;-Cz-haloalkyl;
RS is halogen, nitro, C;-Cy-haloalkyl, C;-Cy-alkoxy,
C1-Cs-haloalkoxy, C;-C4-alkylthio, C;-Cy-haloalkylthio,
Ci1-C4-alkylsulfonyl or C;-Cs-haloalkylsulfonyl;
R? is hydroxyl, C;-Cg-alkoxy, C3-Cg¢-alkenyloxy,
C1-Cg-alkylsulfonyloxy, C;-Cg-alkylcarbonyloxy,
C;-C4-(alkylthio)carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, Ci;-C4-alkyl, C;-Cs-haloalkyl, C;-Cz-alkoxy or C;-Cs-haloalkoxy;
R8,R? are C;-Cy-alkyl;
R10 is hydrogen or C;-Cs-alkyl; where the number of the carbon atoms of the radicals 40 R8, R? and R10 together is at most 7,
R11 is hydrogen or C;-Cs-alkyl; and their agriculturally useful salts.
0050/50555
To AMENDED SHEET ® 2 - Moreover, the invention relates to intermediates and processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.
Pyrazol-4-yl benzoyl derivatives are disclosed in the literature, for example in WO 96/26206 and WO 98/31681.
However, the herbicidal properties of the prior-art compounds and their compatibility with crop plants are not entirely satisfactory.
A need exists to provide novel, in particular herbicidally active, compounds having improved properties.
The present invention provides the 3-(heterocyclyl)- substituted benzoylpyrazoles of the formula I and their herbicidal action.
Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing-these compositions and . - methods for controlling undesirable vegetation using the : compounds I.
Depending on the substitution pattern, the compounds of the - formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.
The compounds of the formula I can also be present in the form of their agriculturally useful salts, the kind of salt usually being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal : action of the compounds I. : 40 suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, . copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be 45 replaced by C;-C4-alkyl, hydroxy-C;-C4;-alkyl,
C;-C4-alkoxy-C;-C4-alkyl, hydroxy-C;-Cs-alkoxy~C;-C4-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium,
. 0050/50555 ® . ® 3 diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-l-oxy)eth-1l-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C;-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C;-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C;-Cs-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic molecular moieties mentioned for the substituents
R1-R1l or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, (alkylthio)carbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term “halogen” represents in each case fluorine, chlorine, bromine or iodine.
Examples of other meanings are: - C1-C4-alkyl, and the alkyl moieties of C;-C4-alkylcarbonyl and
C1-Cs-alkylcarbonyloxy: for example methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; - Ci1-Ce-alkyl, and the alkyl moieties of C;-Cg-alkylcarbonyl and
C;~-Cg-alkylcarbonyloxy: C;-C4-alkyl as mentioned above, and also, for example, pentyl, l-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, l-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, l-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 40 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, l-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, l-ethyl-l-methylpropyl and l-ethyl-3-methylpropyl; 45 - C1-C4-haloalkyl: a C;-Cy-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example,
- 0050/50555
® a chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl, l-chloroethyl, 1l-bromoethyl,
l-iodoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodethyl, 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, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl,
2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,
1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;
- C,-Cs~-alkoxy: for example methoxy, ethoxy, propoxy,
l-methylethoxy, butoxy, l-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
- C1-Cg-alkoxy: C;-Cs-alkoxy as mentioned above, and also, for example, pentoxy, l-methylbutoxy, 2-methylbutoxy,
3-methylbutoxy, 1,1l-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, l-ethylpropoxy, hexoxy, l-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy,
l-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, l-ethyl-l-methylpropoxy and l-ethyl-2-methylpropoxy;
- C;-Cy-haloalkoxy: a C;-Cy-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy,
40 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy,
2-chloro-2-fluorocethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy,
45 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy,
- 0050/50555 ® 5 heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, l-(chloromethyl)-2-chloroethoxy, l-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; - C,-Cy-alkylthio, and the alkylthio moieties of
Ci1-C4-(alkylthio)carbonyloxy: for example methylthio, ethylthio, propylthio, l-methylethylthio, butylthio, l-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio; - C;-C4-haloalkylthio: a C;-Cy-alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluorocethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, l1-(chloromethyl)-2-chloroethylthio, l-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio; - C;-Cy-alkylsulfonyl (C;-C4-alkyl-S(=0),-), and the alkylsulfonyl moieties of C;-C4-alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, l-methylethylsulfonyl, butylsulfonyl, l-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,l1-dimethylethylsulfonyl; - C;-Cg-alkylsulfonyl, and the alkylsulfonyl moieties of
C;-Cg¢-alkylsulfonyloxy: a C;-Cs~alkylsulfonyl radical as 40 mentioned above, and also, for example, pentylsulfonyl, l-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, l-ethylpropylsulfonyl, hexylsulfonyl, l-methylpentylsulfonyl, 45 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1l-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,
- 0050/50555 ® 6 2,2~-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3~-dimethylbutylsulfonyl, l-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, l-ethyl-l-methylpropylsulfonyl and l-ethyl-2-methylpropylsulfonyl;
- C;-Cs-haloalkylsulfonyl: a C;-Cy-alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example,
fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl,
2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,
2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl,
2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, l1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2- chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl,
4-bromobutylsulfonyl and nonafluorobutylsulfonyl;
- C3-C¢-alkenyloxy: for example prop-l-en-l-yloxy, prop-2-en-1l-yloxy, l-methylethenyloxy, buten-1l-yloxy, buten-2-yloxy, buten-3-yloxy, l-methylprop-l-en-1l-yloxy,
2-methylprop-l-en-1-yloxy, l-methylprop-2-en-1l-yloxy, 2-methylprop-2-en-l-yloxy, penten-l-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, l-methylbut-l-en-l-yloxy, 2-methylbut-l-en-1-yloxy, 3-methylbut-l-en-l-yloxy, l-methylbut-2-en-1-yloxy, 2-methylbut-2-en-l-yloxy,
40 3-methylbut-2-en-1-yloxy, l-methylbut-3-en-1l-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1l-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1l-yloxy, 1,2-dimethylprop-2-en-l-yloxy, l-ethylprop-l-en-2-yloxy, l-ethylprop-2-en-l-yloxy, hex-l-en-l-yloxy, hex-2-en-1l-yloxy,
45 hex-3-en-1-yloxy, hex-4-en-1l-yloxy, Hex-5-en-1l-yloxy, l-methylpent-l-en-1-yloxy, 2-methylpent-l-en-1l-yloxy, 3-methylpent-l-en-1-yloxy, 4-methylpent-l-en-l-yloxy,
. 0050/50555
® 7 l-methylpent-2-en-l-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1l-yloxy, l-methylpent-3-en-l-yloxy, 2-methylpent-3-en-l-yloxy, 3-methylpent-3-en-1l-yloxy, 4-methylpent-3-en-l-yloxy,
l-methylpent-4-en-1l-yloxy, 2-methylpent-4-en-l-yloxy, 3-methylpent-4-en-1l-yloxy, 4-methylpent-4-en-1l-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1l-dimethylbut-3-en-l-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-l-en-l-yloxy,
1,3-dimethylbut-2-en-1l-yloxy, 1,3-dimethylbut-3-en-l-yloxy, 2,2-dimethylbut-3-en-l-yloxy, 2,3-dimethylbut-l-en-1l-yloxy, 2,3-dimethylbut-2-en-l-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-l-en-1l-yloxy, 3,3-dimethylbut-~2-en-1l-yloxy, l-ethylbut-l-en-1-yloxy, l-ethylbut-2-en-l-yloxy,
l-ethylbut-3-en-1-yloxy, 2-ethylbut-l-en-1l-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1l-yloxy, l-ethyl-~l-methylprop-2-en-1-yloxy, l-ethyl-2-methylprop-l-en-1l-yloxy and l-ethyl~2-methylprop-2-en-1- yloxy;
- C3;-Cg-alkenyl: prop-l-en-l-yl, prop-2-en-l-yl, l-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl,
l-methylprop-l-en-1-yl, 2-methylprop-l-en-1-yl, l-methylprop-2-en-1-yl, 2-methylprop-2-en-l-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, l-methylbut-l-en-1-yl, 2-methylbut-l-en-1-yl, 3-methylbut-l-en-1l-yl, l-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl,
3-methylbut-2-en-1-yl, l-methylbut-3-en-1l-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-l-en-1-yl, 1,2-dimethylprop-2-en-1-yl, l-ethylprop-l-en-2-yl, l-ethylprop-2-en-1-yl, hex-l-en-1-yl, hex-2-en-1-yl,
hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, l-methylpent-l1-en-1-y1, 2-methylpent-l-en-1-vyl, 3-methylpent-l-en-1-yl, 4-methylpent-l-en-1-yl, l-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl,
40 l-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, l-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1l-dimethylbut-3-en-1-yl,
45 1,2-dimethylbut-l-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1l,2-dimethylbut-3-en-1-yl, 1,3~dimethylbut-l-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,
. 0050/50555 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-l-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-l-en-1-yl, 3,3-dimethylbut-2-en-1-yl, l-ethylbut-1l-en-1-yl, l-ethylbut-2-en-1-yl, l-ethylbut-3-en-1-yl, 2-ethylbut-l-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, l-ethyl-1l-methylprop-2-en-1-yl, . l-ethyl-2-methylprop-l-en-1l-yl and l-ethyl-2-methylprop-2-en-1-yl.
The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one nitro group, one cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups.
Emphasis is given to those 3-(heterocyclyl)-substituted benzoyl- pyrazoles of the formula I where
R? is hydroxyl, C;-Cg¢-alkoxy, C3-Cg¢-alkenyloxy, C;-Cg-alkyl- sulfonyloxy, C;-Cg-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C;-Cs-alkyl, C;-Cs-haloalkyl,
C1-C4-alkoxy or C;-Cs-haloalkoxy. . Preference is given to the 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where:
X is 0;
Rl is C;-C4-alkyl; particularly preferably methyl or ethyl; with particular preference methyl;
R2,R3,R%,R% are hydrogen, C;-Cy-alkyl or C;-Cs-haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, l-methylethyl, fluoromethyl or 40 chloromethyl; with particular preference hydrogen, methyl, ethyl or chloromethyl;
RG is C;~-C4-alkylthio or C;-Cy-alkylsulfonyl; 45 particularly preferably methylthio, ethylthio or l-methyl-l-ethylthio, methylsulfonyl, ethylsulfonyl, l-methylethylsulfonyl or
‘ 0050/50555 ® ) propylsulfonyl; with particular preference methylsulfonyl, ethylsulfonyl, l-methylethylsulfonyl or propylsulfonyl;
R7 is hydroxyl, C;-Cg-alkoxy, C3-Cg-alkenyloxy,
C;-Ce-alkylsulfonyloxy, C;-Cg-alkylcarbonyloxy,
C1-C4-(alkylthio)carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C;-Cs-alkyl, C;-Cy-haloalkyl,
C;-C4-alkoxy or C;-Cy-haloalkoxy; particularly preferably hydroxyl, C;-Cs-alkoxy,
C3-Cg-alkenyloxy, C;-Cs-alkylsulfonyloxy,
C;-Cy-alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C;-Cs-alkyl, C;-Cs-haloalkyl,
Ci1-Cy-alkoxy or C;-Cs-haloalkoxy;
R8,R? are C;-Cg-alkyl; particularly preferably methyl, ethyl, propyl, l-methyl-1l-ethyl, butyl, l-methyl-l-propyl and 2-methyl-1-propyl;
R10 is hydrogen or C;-Cy-alkyl; particularly preferably C;-Cgz-alkyl; with particular preference methyl, ethyl or propyl;
R11 is hydrogen or C;-C4-alkyl; particularly preferably hydrogen or methyl.
Particular preference is given to the 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula 40 I where
X is 0;
Rl is C;-Cy-alkyl; 45 particularly preferably methyl or ethyl; with particular preference methyl;
Claims (32)
1. A 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I X 2 o RI R R11 | R3 R4 RS I NSN" Sgr RS ei we where: X is 0, NH or N(C;-Cg¢-alkyl); Rl is C;-Cg-alkyl; RZ,R3,R4,R5 are hydrogen, C,-Cq-alkyl or C;-Cs-haloalkyl; R6 is halogen, nitro, C;-C4-haloalkyl, C;-Cs-alkoxy, C1-Cs-haloalkoxy, C;-Cs-alkylthio, Ci-C4-haloalkylthio, C;-C4-alkylsulfonyl or C;-C4~-haloalkylsulfonyl; R7 is hydroxyl, C;-Cg-alkoxy, C3-Cg-alkenyloxy, C;-Cg-alkylsulfonyloxy, C;-Cg¢-alkylcarbonyloxy, C;-C4-(alkylthio)carbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C;-Cs4-alkyl, C;-Cy-haloalkyl, C1-Cs-alkoxy or C;-Cys-haloalkoxy; R8,RY are C;-Cs-alkyl; R10 is hydrogen or C;-Cy-alkyl; 40 where the number of the carbon atoms of the radicals R8, R? and R!0 together is at most 7, R11 is hydrogen or C;-C4-alkyl; 45 and its agriculturally useful salts.
. . 0050/50555 @ a9
2. A 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I as claimed in claim 1 where X is 0; Rl is C;-Cg4-alkyl; R6 is C;-Cg-alkylthio or C;-Cg-alkylsulfonyl.
3. A 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I as claimed in claim 1 where X is 0; Rl is C;-C4-alkyl; ‘ R6 is halogen, nitro, C;-C4-haloalkyl, C;-Cs-alkoxy or C;-Cy-haloalkoxy.
4. A 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I as claimed in claim 1 where X is N(C;-Cg-alkyl).
5. A process for preparing 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where R7 = hydroxyl as claimed in claim 1, which comprises acylating a pyrazole of the formula II rll TI Nn H II wa we with an activated benzoic acid IIIa or a benzoic acid IIIf, X R2 i X 2 0] Rl 0) Rl R R3 | R3 R4 R4 Ll RS HO RS 40 R6 R6 IIIa IIIf where the variables X, Rl! to R6 and R® to R!l are as defined in claim 1 and L! is a nucleophilically replaceable leaving 45 group and rearranging the acylation product, in the presence
. . 0050/50555 or absence of a catalyst, to give the compounds of the formula I where R7 = hydroxyl.
6. A process for preparing 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where R? = OH as claimed in claim 1, which comprises reacting a pyrazole of the formula IT R11 N H II Rl Toe in which the variables R8 to R!! are as defined in claim 1, or an alkali metal salt thereof, with a 3-(heterocyclyl)benzene derivative of the formula V 1 X R? R N- R3 L2 R4 v R3 R6 where the variables X and R! to R® are as defined in claim 1 and L2 is a leaving group in the presence of carbon monoxide, a catalyst and a base.
7. A process for preparing 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I where R? * hydroxyl as claimed in claim 1, which comprises reacting a 3-(heterocyclyl)-substituted benzoylpyrazole I where R7 = hydroxyl 1 X R2
[0] R N~- R11 R3 4 I R5 R I where R7 = OH N~y H R6 Rl ore with a compound of the formula VI 40 ] L3-R7a VI where 45 I3 is a nucleophilically replaceable leaving group;
+ . 0050/50555 C 1 ® 51 R72 is C;-Cg~alkyl, C3-Cg-alkenyl, C;-Cg-alkylsulfonyl, C;-Cg-alkylcarbonyl, C;-Cs-(alkylthio)carbonyloxy, phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C;-Cs-alkyl, C3-Cs-haloalkyl, C;-Cs-alkoxy or C;-C4-haloalkoxy.
8. A benzoic acid ester of the formula III 0 Rl R2 ) R3 L Ri ITI RS R6 where the variables X, Rl and R3 to Rf are as defined in claim 1 and RZ is C;-Cs-haloalkyl; and L is hydroxyl or a radical that can be removed by hydrolysis.
9. A 3-(heterocyclyl)benzene derivative of the formula V R2 L R4 v R5 R6 where the variables X, Rl and R3 to R® are as defined in claim 1 and 40 R2 is C;-C4-haloalkyl; and L2 is a nucleophilically displaceable leaving group.
10. A composition, comprising a herbicidally effective amount of 45 at least one 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I or an agriculturally useful salt of I as
0050/50555 AMENDED SHEET ® 52 ' claimed in any of claims 1 to 4 and auxiliaries which are customarily used for formulating crop protection agents.
11. A process for preparing compositions as claimed in claim 8, which comprises mixing a herbicidally effective amount of at least one 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in any of claims 1 to 4 and auxiliaries which are customarily used for formulating crop protection agents.
12. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one 3-(heterocyclyl)-substituted benzoylpyrazole of the formula I or an agriculturally useful salt of I as claimed in any one of claims 1 to 4 to act on the plants, their habitat and/or on seed.
13. The use of the 3-(heterocyclyl)-substituted benzoylpyrazoles of the formula I and/or their agriculturally useful salts as claimed in any of claims 1 to 4 as herbicides.
14. The compound of formula I as claimed in any one of claims l to 4, substantially as hereinbefore described or : exemplified.
15. The compound of formula I including any new and inventive integer or combination of integers, substantially as herein described.
16. A process according to the invention for preparing the compound of formula I, substantially as hereinbefore described or exemplified.
17. A process for preparing the compound of formula I including any new and inventive integer or combination of . integers, substantially as herein described.
18. The compound of formula III as claimed in claim 8, substantially as hereinbefore described or exemplified.
19. The compound of formula III including any new and inventive integer or combination of integers, substantially as herein described.
® AMENDED PAGE
20. The compound of formula V as claimed in claim 9, substantially as hereinbefore described or exemplified.
21. The compound of formula V including any new and inventive integer or combination of integers, substantially as herein described.
22. The composition comprising the compound of formula I as claimed in claim 10, substantially as hereinbefore described or exemplified.
23. The composition comprising the compound of formula I including any new and inventive integer or combination of integers, substantially as herein described.
24. A process according to the invention for preparing the composition comprising the compound of formula I, substantially as hereinbefore described or exemplified.
25. A process for preparing the composition comprising the compound of formula I including any new and inventive integer or combination of integers, substantially as herein described.
26. A method according to the invention for controlling undesirable vegetation, substantially as hereinbefore described or exemplified.
27. A method for controlling undesirable vegetation including any new and inventive integer or combination of integers, substantially as herein described.
28. The use of the compound of formula I as claimed in claim 13, substantially as hereinbefore described or exemplified.
29. The use of the compound of formula I including any new and inventive integer or combination of integers, substantially as herein described.
® AMENDED PAGE
30. The compound of formula I or the composition comprising thereof as claimed in any one of claims 1 to 4, 10, 14, 15, 22 and 23 whenever supplied with instructions for the use thereof in controlling undesirable vegetation.
31. The compound of formula I or the composition comprising thereof as claimed in claim 30 when the instructions are in printed or written form.
32. The compound of formula I or the composition comprising thereof as claimed in claim 31 supplied in a package or container having the said instructions provided therein or thereon.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19855850 | 1998-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200105477B true ZA200105477B (en) | 2002-07-18 |
Family
ID=7889889
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105476A ZA200105476B (en) | 1998-12-04 | 2001-07-03 | 3-(heterocyclyl)-benzoylpyrazole-derivatives. |
| ZA200105477A ZA200105477B (en) | 1998-12-04 | 2001-07-03 | 3-(heterocyclyl)-substituted benzoylpyrazols. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200105476A ZA200105476B (en) | 1998-12-04 | 2001-07-03 | 3-(heterocyclyl)-benzoylpyrazole-derivatives. |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR021540A1 (en) |
| AU (1) | AU2094700A (en) |
| WO (1) | WO2000034247A2 (en) |
| ZA (2) | ZA200105476B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3997255B2 (en) | 2004-02-13 | 2007-10-24 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | Androgen receptor modulator |
| US7507860B2 (en) | 2004-04-13 | 2009-03-24 | Pfizer Inc. | Androgen modulators |
| TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57212162A (en) * | 1981-06-23 | 1982-12-27 | Sankyo Co Ltd | Pyrazole derivative and herbicide |
| KR19980702466A (en) * | 1995-02-24 | 1998-07-15 | 페라 스타르크, 요헨 카르크 | Pyrazol-4-yl-benzoyl derivatives and their use as herbicides |
| WO1997041117A1 (en) * | 1996-04-26 | 1997-11-06 | Nippon Soda Co., Ltd. | Novel benzene derivatives substituted by heterocycles and herbicides |
| AU1670797A (en) * | 1996-04-26 | 1997-11-19 | Nippon Soda Co., Ltd. | Benzene derivatives substituted by heterocycles and herbicides |
| HUP9902423A3 (en) * | 1996-04-26 | 2001-02-28 | Nippon Soda Co | Benzene derivatives substituted by heterocycles and herbicides |
| AU3297397A (en) * | 1996-06-06 | 1998-01-05 | E.I. Du Pont De Nemours And Company | Herbicidal pyridinyl and pyrazolylphenyl ketones |
| WO1998021187A1 (en) * | 1996-11-13 | 1998-05-22 | Nippon Soda Co., Ltd. | Novel heterocycle substituted benzene derivatives and herbicide |
-
1999
- 1999-12-01 AU AU20947/00A patent/AU2094700A/en not_active Abandoned
- 1999-12-01 WO PCT/EP1999/009343 patent/WO2000034247A2/en active Application Filing
- 1999-12-03 AR ARP990106175 patent/AR021540A1/en unknown
-
2001
- 2001-07-03 ZA ZA200105476A patent/ZA200105476B/en unknown
- 2001-07-03 ZA ZA200105477A patent/ZA200105477B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR021540A1 (en) | 2002-07-24 |
| WO2000034247A2 (en) | 2000-06-15 |
| WO2000034247A3 (en) | 2000-11-23 |
| ZA200105476B (en) | 2002-07-16 |
| AU2094700A (en) | 2000-06-26 |
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