MXPA01005666A - Sizing composition - Google Patents
Sizing compositionInfo
- Publication number
- MXPA01005666A MXPA01005666A MXPA/A/2001/005666A MXPA01005666A MXPA01005666A MX PA01005666 A MXPA01005666 A MX PA01005666A MX PA01005666 A MXPA01005666 A MX PA01005666A MX PA01005666 A MXPA01005666 A MX PA01005666A
- Authority
- MX
- Mexico
- Prior art keywords
- ial
- formula
- nch3
- alkyl
- heterocyclyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 45
- 238000004513 sizing Methods 0.000 title abstract 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- -1 haloalkyl halogen Chemical class 0.000 claims description 278
- 150000001875 compounds Chemical class 0.000 claims description 125
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000003545 alkoxy group Chemical group 0.000 claims description 47
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 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 31
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 239000011780 sodium chloride Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 230000002363 herbicidal Effects 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 15
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 14
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- 239000011814 protection agent Substances 0.000 claims description 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 230000001276 controlling effect Effects 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000006185 dispersion Substances 0.000 abstract description 9
- 239000000839 emulsion Substances 0.000 abstract description 7
- 239000008346 aqueous phase Substances 0.000 abstract description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 6
- 125000002091 cationic group Chemical group 0.000 abstract 3
- 239000003381 stabilizer Substances 0.000 abstract 3
- 125000000129 anionic group Chemical group 0.000 abstract 2
- 230000002209 hydrophobic Effects 0.000 abstract 2
- 239000012071 phase Substances 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 42
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 22
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 21
- 102100004109 HEY1 Human genes 0.000 description 18
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 18
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 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
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- 230000000875 corresponding Effects 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Chemical group 0.000 description 6
- 150000008041 alkali metal carbonates Chemical group 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 150000002940 palladium Chemical class 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000001184 potassium carbonate Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 230000027455 binding Effects 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 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
- 239000008187 granular material Substances 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
- 150000003254 radicals Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004995 haloalkylthio group Chemical group 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
- 239000000463 material Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical group CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000001559 benzoic acids Chemical class 0.000 description 3
- 238000009835 boiling Methods 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
- 244000038559 crop plants Species 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- 150000002825 nitriles Chemical class 0.000 description 3
- 150000002923 oximes Chemical class 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- 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 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 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
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- 235000006463 Brassica alba Nutrition 0.000 description 2
- 235000011371 Brassica hirta Nutrition 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
- 235000010469 Glycine max Nutrition 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 240000006962 Gossypium hirsutum Species 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N Isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L Palladium(II) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 235000004443 Ricinus communis Nutrition 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
- 235000005773 Setaria viridis Nutrition 0.000 description 2
- 240000003461 Setaria viridis 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N Trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- LEIMLDGFXIOXMT-UHFFFAOYSA-N Trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 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
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 150000008055 alkyl aryl sulfonates 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
- 239000002956 ash Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 235000010086 green foxtail Nutrition 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 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 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
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- 239000002671 adjuvant Substances 0.000 description 1
- 230000000240 adjuvant Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
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- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- XUMDNHCCUNPEEY-UHFFFAOYSA-N bis(2-hydroxyethylidene)azanium Chemical compound OCC=[N+]=CCO XUMDNHCCUNPEEY-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- CXLSVMAGOLTCSL-UHFFFAOYSA-J calcium;barium(2+);dicarbonate Chemical compound [Ca+2].[Ba+2].[O-]C([O-])=O.[O-]C([O-])=O CXLSVMAGOLTCSL-UHFFFAOYSA-J 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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- 238000005810 carbonylation reaction Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
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- 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
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- 239000010949 copper Substances 0.000 description 1
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- 150000004891 diazines Chemical class 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
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
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- 238000004821 distillation Methods 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
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- KVXNKFYSHAUJIA-UHFFFAOYSA-M ethoxyethane;acetate Chemical compound CC([O-])=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-M 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 125000005816 fluoropropyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])* 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
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- 125000006343 heptafluoro propyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- OHORFAFFMDIQRR-UHFFFAOYSA-N hexafluorosilicate(2-) Chemical compound F[Si-2](F)(F)(F)(F)F OHORFAFFMDIQRR-UHFFFAOYSA-N 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
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- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- YBCISJAPWKQOPH-UHFFFAOYSA-N iodoethane Chemical group [CH2]CI YBCISJAPWKQOPH-UHFFFAOYSA-N 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 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
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M methanoate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000018343 nutrient deficiency Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000008048 phenylpyrazoles Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L phosphate Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000003032 phytopathogenic Effects 0.000 description 1
- 230000000885 phytotoxic Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 235000013526 red clover Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 235000012222 talc Nutrition 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
- 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
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- 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
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 235000021307 wheat Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Abstract
The present invention relates to a stabilized emulsified or dispersed composition comprising a hydrophobic phase and an aqueous phase, the composition being stabilized by a cationic colloidal coacervate stabilizing agent, the coacervate stabilizing agent comprising an anionic component and a cationic component, the anionic and cationic components being present in a proportion such that the composition has a zeta potential of at least about 20 millivolts. The hydrophobic phase is preferably a non-rosin sizing agent, including a reactive or nonreactive sizing agent, although mixtures of rosin and non-rosin sizing agents can form stable emulsions or dispersions using the coacervate of the invention. Methods of making and using the stable emulsions or dispersions are also disclosed, as is sized paper made using an emulsified or dispersed sizing agent stabilized with the coacervate stabilizing agent of the invention.
Description
DERIVATIVES OF 3- (HETEROCICLIL, BENZOYLPIRAZZOL The present invention relates to 3- (heterocyclic) benzoylpyrazole derivatives of the formula I
wherein: X is O, NH or N (C-C-alkyl); R 1 is nitro, halogen, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylsulfonyl, or C 1 haloalkylsulfonyl. - C4; R2 RJ, R4,?. ~, Are hydrogen, C.sub.4 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl R.sub.H is halogen, nitro, C.sub.H haloalkyl, C.sub.4 -C.sub.4 alkoxy, C.sub.4 -C.sub.4 haloalkoxy, alkylthio O-Z ?, haloalkylthio C_-C4, alkylsulfonyl C -C or haloalkyl Isulfonyl C? -C4; R 7 is hydroxyl, C 1 -C 6 alkenyloxy C -Cd alkoxy, C 1 -C 6 alkylsulfonyloxy, to C 1 -C 6 -carbonyloxy,
(alkylthio) C.-Cj-carbonyloxy, phenylsulphonyloxy or f-phenylcarbonyloxy, wherein the phenyl radical of the two above-mentioned substituents may be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C1-C4 alkyl, haloalkyl C? ~ C4, alkoxy C.- C4 or haloalkoxy C.-C4; R8, R9 are C] -C4 alkyl; R 10 is hydrogen or C 1 -C 4 alkyl; where the number of carbon atoms of the radicals
R8, R9 and R10 together is at most 7; R11 is hydrogen or C? -C4 alkyl; and its useful salts in agriculture. In addition, the invention relates to intermediates and processes for the preparation of compounds of formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them to control 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. It is an object of the present invention to offer novel, particularly herbicidally active compounds having improved properties. We have found that this object is achieved through 3- (heterocyclic) benzoylpyrazole derivatives of the formula I and its herbicidal action. In addition, we have found herbicidal compositions that flft comprise the compounds I and have a very good herbicidal action. In addition, we have found processes for the
Preparation of these compositions and methods for controlling undesirable vegetation using the compounds I. According to the substitution pattern, the compounds of the formula
I may contain one or several chiral centers, in said
^ case they are present as enantiomers or mixtures of
diastereomers. The invention offers both pure enantiomers or diastereomers and their mixtures. The compounds of the formula I can also be present in the form of their salts useful for agriculture, the type of salt is usually not a relevant factor. In general, they are
Suitable are the salts of the cations or the acid addition salts of the acids whose cations and anions,
^ fc respectively, do not adversely affect the herbicidal action of compounds I. Suitable cations are, in particular, metal ions
alkaline, preferably lithium, sodium and potassium, alkaline earth metals, preferably calcium and magnesium, and transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired , from one to four hydrogen atoms can be replaced by
C 1 -C 4 alkyl, C 1 -C 4 hydroxyalkyl, C 1 -C 4 alkoxy C 1 -C 6 alkyl, C 1 -C 4 hydroxyalkoxy C. C alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium , tetrabutylammonium, 2- (2-hydroxyethyl-1-yl) et-1-ylammonium, di (2-hydroxyethyl-1-yl) ammonium, trimethylbenzyl onium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1? -C4) sulfonium, and sulfoxonium ions, preferably tri (C1-C4 alkyl) sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, Sulfate, dihidrogensulfato, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of alkanoic acids C? -C4, preferably formate, acetate, propionate and butyrate. The organic moieties mentioned for the substituents R1-R11 or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, ie alkyl all portions ,, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, (alkylthio) carbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy may be straight or branched chain . Unless otherwise indicated, halogenated substituents preferably have one to five identical or different halogen atoms. The term "halogen" in each case represents fluorine, chlorine, bromine or iodine. Examples of other significant are: - alkyl C.-C4, and the alkyl portions of alkylcarbonyl C1-C4 alkylcarbonyloxy C1-C4: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl; - CI-CT alkyl, and the alkyl portions of Ci-Cß alkylcarbonyl and C?-C6 alkylcarbonyloxy: C 4 -C 4 alkyl according to the above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, l-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-trimethylpropyl, 1-ethyl- l-methylpropyl and l-ethyl-3-methylpropyl; - haloalkyl C? -C4: a C: -C alkyl radical according to the above mentioned partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl , trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, 1- iodoethyl, 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, pentafluoroethyl, 2-5 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- 10 fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2- bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl; C 4 -C 4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-15 dimethylethoxy; - alkoxy C: -Ce: C: -C4 alkoxy according to the above, and also, for example, pentoxy, 1-methylbutoxy, 2- • methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1,2- dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy 20, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2 2- dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1- ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and l ethyl-2-ethylpropoxy;
haloalkoxy C? ~ C: a C1-C4 alkoxy radical according to the above mentioned partially or totally substituted by fl fl or, chloro, bromo and / or iodo, ie, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy,
-chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy,
2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- ^^ trichloroethoxy, pentafluoroethoxy, 2- fluoropropoxy, 2-10 chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 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, heptafluoropropoxy, 1- (fluoromethyl) -2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2- 15 bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; alkylthio C? ~ C4, and the alkylthio portions of
• (alkylthio) carbonyloxy C 1 -C 4: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2- 20 methylpropylthio and 1,1-dimethylethylthio; haloalkylthio C? -C4: they are all an alkylthio C? -C4 radical according to the above mentioned partially or totally substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, fluoromethylthio difluoromethylthio, trifluoromethylthio,
chlorodifluoromethylthio, bromodifluoromethylthio, 2- d
fluoroethylthio, 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-fluoroethylthio, 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, 2,2,3,3,3-10 pentafluoropropylthio, heptafluoropropylthio, 1- ( fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio; alkylsulfonyl C? ~ C4 - (C.sub.C-C4-S alkyl (= 0) 2-) and the
alkylsulfonyl portions of alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-ethylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl; - Ci-Cg alkylsulfonyl, and the alkylsulfonyl portions of C 1 -C 6 alkylsulfonyloxy: a C 1 -C 4 alkylsulfonyl radical as mentioned above, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1 , 1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-ethylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1 / 2- fl-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3- 5 dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1-trimethylpropylsulfonyl, 1,2,2- trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl; ^ * - haloalkylsulfonyl C? -C4: an alkylsulfonyl radical C: -C4
As mentioned above partially or completely substituted by fluorine, chlorine, bromine and / or iodine, ie, for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2- 15-chloroethylsulfonyl, 2-bromoethylsulfonyl, -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, 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, | B-heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2,5-chloroethylsulfonyl, 1- (bromomethyl) -2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, - bromobutylsulfonyl and nonafluorobutylsulfonyl; - C3-C0 alkenyloxy: for example prop-1-en-l-yloxy, prop-2-en-yloxy, 1-methylenynyloxy, buten-1-yloxy, buten-2-yloxy, buten-10 3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten- 1- Iloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1- methylbut-1-en-l-yloxy, 2-methylbut-l-en-l-yloxy, 3-methylbutyl- l- en-1-yloxy, l-methylbut-2-en-l-yloxy, 2-methylbut-2-en-l-yloxy, 3-methylbut-2-en-l-yloxy, l-methylbut-3 -in-l-yloxy, 2- methylbut-3-en-l-yloxy, 3-methylbut-3-eh-l-yloxy, 1,1-dimethylprop-2-en-l-iioxy, 1,2-dimethylpropyl -l-en-l-yloxy, 1,2- • dimethylprop-2-en-l-yloxy, l-ethylprop-l-en-2-yloxy, 1- ethylprop-2-en-l-yloxy, hex- 1-en-l-yloxy, hex-2-en-l-yloxy,
hex-3-en-l-yloxy, hex-4-en-l-yloxy, hex-5-en-l-yloxy, 1-methylpent-l-en-l-yloxy, 2-methylpent-l-en -l-iloxy, 3-methylpent-l-en-l-yloxy, 4-methylpent-l-en-1-yloxy, l-methylpent-2-en-l-yloxy, 2-methylpent-2-en-l -iloxy, 3-methylpent-2-en-l-yloxy, 4-methylpent-2-en-l-yloxy, 25 l-methylpent-3-en-l-yloxy, 2-methylpent-3-en-l- Ioxy, 3-methylpent-3-en-l-yloxy, 4-methylpent-3-en-l-yloxy, 1-methylpent-4-en-l-yloxy, 2-methylpent-4-en-l-yloxy, 3-methylpent-4-en-l-yloxy, 4-methylpent-4-en-l-yloxy, 1, l-dimethylbut-2-en-l-yloxy, 1, l-dimethylbut-3-en-l- Iloxy, 1,2-dimethylbut-l-en-l-yloxy, 1,2-dimethylbut-2-en-l-yloxy, 1,2-dimethylbut-3-en-l-yloxy, 1,3-dimethylbutyl- l-en-l-yloxy, 1,3-dimethylbut-2-en-l-yloxy, 1,3-dimethylbut-3-en-l-yloxy, 2,2-dimethylbut-3-en-l-yloxy, 2, 3-dimethylbut-l-en-l-yloxy, 2,3-dimethylbut-2-en-l-yloxy, 2,3-dimethylbut-3-en-l-yloxy, 3, 3-dimethylbut-l- en-l-yloxy, 3, 3-dimethylbut-2-en-l-yloxy, 1-ethylbut-l-en-l-yloxy, l-ethylbut-2-en-l-yloxy, l-ethylbut-3- en-l-yloxy, 2-ethylbut-l-en-l-yloxy, 2- ethylbut-2-en-l-yloxy, 2-ethylbut-3-en-l-yloxy, 1,1, 2-trimethylprop-2-en-l-yloxy, 1-ethyl-1-methylprop-2-en- l-iloxy, l-ethyl-2-methylprop-l-en-l-yloxy and l-ethyl-2-methylprop-2-en-l-yloxy; - C3-C6 alkenyl: prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1- methylprop-l-en-l-yl, 2-methylprop-l-en-l-yl, 1-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, penten-1- ilo, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-l-en-l-yl, 2-methylbut-1-en-l-yl, 3-methylbut-l- en-l-yl, l-methylbut-2-en-1-yl, 2-methylbut-2-en-l-yl, 3-methylbut-2-en-l-yl, 1-methylbut-3-enyl l -yl, 2-methylbut-3-en-l-yl, 3-methylbut-3-en-1-yl, 1, l-dimethylprop-2-en-l-yl, 1,2-dimethylprop-l- en-1-yl, 1,2-dimethylprop-2-en-l-yl, l-ethylprop-l-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en- l -yl, hex-2-en-l-yl, hex-3-en-l-yl, hex-4-en-l-yl, hex-5-en-l-yl, 5-methylpentyl -in-l-yl, 2-methylpent-l-en-l-yl, 3-methylpent-l-en-l-yl, 4-methylpent-1-en-l-yl, l-methylpent-2-en -l-ilo, 2-methylpent-2-en-l-yl, 3-methylpent-2-en-l-yl, 4-methylpent-2-en-l-yl, l-methylpent-3-en-l -? lo, 2-methylpent-3-en-l-yl, • 10 3-methylpent-3-en-l-yl, 4-methylpent-3-en-l-yl, 1-methylpent -4-en-l-yl, 2-methylpent-4-en-l-yl, 3-methylpent-4-en-l-yl, 4-methylpent- -en-l-yl, 1, l-dimethylbut- 2-en-l-yl, 1, l-dimethylbut-3-en-l-yl, 1,2-dimethylbut-l-en-l-yl, 1,2-dimethylbut-2-en-l-yl, 15 1, 2-dimethylbut-3-en-l-yl, 1,3-dimethylbut-l-en-l-yl, 1,3-dimethylbutyl-2-en-l-yl, 1,3-dimethylbut-3 -in-l-yl, 2, 2-dimethylbut-3-en-l-yl, 2, 3-dimethylbut-l-en-l-yl, • 2,3-dimethylbut-2-en-l-yl, 2, 3-dimethylbut-3-en-l-yl, 3, 3-dimethylbut-l-en-l-yl, 3, 3-dimethylbut-2-en-l-yl, 1-ethylbut-l-en -l-yl, l-ethylbut-2-en-l-yl, l-ethylbut-3-en-l-yl, 2-ethylbut-l-en-l-yl, 2-ethylbut-2-en-l -yl, 2-ethylbut-3-en-l-yl, 1, 1, 2-trimethylprop-2-en-l-yl, 1-ethyl-1-methylprop-2-en-l-yl, 25 l- ethyl-2-methylprop-l-en-l-yl and l-ethyl-2-methylprop-2-en-l-yl. The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and / or a nitro group, a cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups. Emphasis is given to these compounds of the formula I wherein R 7 is hydroxyl, Ci-Cβ alkoxy, C 3 -C 5 alkenyloxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 6 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately be partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano, C? -C4alkyl, C? -Chaloalkyl, Ci- C4alkoxy or haloalkoxy C? -C4. * Preference is given to the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: X is O; R 1 is nitro, halogen, Ci-C 4 alkoxy or C 1 -C 4 alkylthio; particularly preferably nitro, halogen or C 1 -C 4 alkoxy; with particular preference halogen, for example fluorine, chlorine or bromine, or C1-C4 alkoxy, such as methoxy or ethoxy; with chlorine or methoxy being very particularly preferred;
R2, R3, R4, R5, are hydrogen, C-C alkyl or C? -C4 haloalkyl; particularly preferably hydrogen,
• methyl, ethyl, propyl, 1-methylethyl, fluoromethyl or chloromethyl; 5, particularly preferably hydrogen, methyl, ethyl or chloromethyl; Rd is alkylthio CL-C4 or C1-C4 alkylsulfonyl; particularly preferably methylthio, ethylthio or 1-methyl-1-ethylthio, methylsulfonyl, ethylsulfonyl, 1-methylethylsulphonyl or propylsulphonyl; particularly preferably methylsulfonyl, ethylsulfonyl, 1-methylethylsulphonyl or propylsulfonyl; R7 is hydroxyl, Ci-Cß alkoxy, C3-C6 alkenyloxy, C alqu.- C6 alkylsulfonyloxy, C?-C6 alkylcarbonyloxy, (Cilt-C4-alkylcarbonyloxy), phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two Substituents mentioned may ultimately be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C? -C alkyl, C? -C4 haloalkyl, C- C alkoxy or haloalkoxy C.- C4; particularly preferably hydroxyl, C 1 -C 4 alkoxy, C 3 -C 6 alkenyloxy, C 1 -C 4 alkylsulfonyloxy,
C 1 -C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately be used; be partially or wholly halogenated and / or carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; R8, R9 are alkyl C.-C; particularly preferably methyl, ethyl, 1-propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R 1"0 is hydrogen or C 1 -C 4 alkyl, particularly preferably C 1 -C 4 alkyl, with methyl, ethyl or propyl being preferred, R x is hydrogen or C 1 -C 4 alkyl, particularly preferably hydrogen Particularly preferred are 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein • X is O; R 1 is halogen or C 1 -C 4 alkoxy, particularly halogen, such as, for example, fluorine, chlorine or bromine or methoxy; ethoxy, with chloro or methoxy being very particularly preferred: R6 is C.sub.4-C.sub.4-alkylsulfonyl, particularly preferably methylsulfonyl, ethylsulfonyl, 1-methyl-1-ethylsulfonyl or propylsulfonyl, R.sup.7 is hydroxyl, alkylsulfonyloxy, Ci.sup.-C, alkylcarbonyloxy
• C?-C,, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two mentioned substituents can ultimately be partially or fully halogenated and / or can carry one to three of the following groups: nitro, cyano, alkyl C 1 -C 4, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; 10, particularly preferably hydroxyl; R8, R9 are Cr-C4 alkyl; RlL is hydrogen or C_-C4 alkyl. Especially preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 8 is C 2 -C alkyl, for example, ethyl, 1-methyl-1-ethyl, propyl or butyl; R ° is C 1 -C 4 alkyl, for example methyl or ethyl; R 1 is hydrogen or C 1 -C 4 alkyl, for example, methyl or ethyl. Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: Re is methyl; R "is C 1 -C 4 alkyl, for example methyl, ethyl, propyl or butyl; R" "is C 1 -C 4 alkyl, for example methyl or ethyl.
Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R8, R9 are methyl; R10 is hydrogen. * Also preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein: X is 0; R 1 is nitro, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; ^^ Nitro, halogen or C.sub.1 -C.sub.4 alkoxy are particularly preferred; with halogen, for example fluorine, chlorine or bromine, or C?-C4 alkoxy, for example methoxy or ethoxy being preferred; with chlorine or methoxy being very particularly preferred; R 2, R 3, R 4, R 5 are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; > ^ particularly preferably hydrogen, methyl, ethyl, propyl, 1-methyl-1-ethyl, chloromethyl or fluoromethyl; 20, particularly preferably hydrogen, methyl, ethyl or chloromethyl; particularly preferably hydrogen, methyl, ethyl or chloromethyl; R6 is halogen, nitro, haloalkyl C? -C4, alkoxy C: ~ C4 or well haloalkoxy C? -C4;
with particular preference being given to halogen, for example chlorine or bromine, nitro, haloalkyl C.-C;, such as, for example, difluoromethyl or trifluoromethyl, C-C2 alkoxy or C? -C2 haloalkoxy, such as, for example, difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy; R7 is hydroxyl, C-C6 alkoxy, C3-C6 anynyloxy, C?-C3 alkylsulfonyloxy, C?-C6 alkylcarbonyloxy, C alqu-C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two
• 10 substituents mentioned may ultimately be partially or totally halogenadc and / or may carry one to three of the following groups: nitro, cyano, C?-C4 alkyl, C halo-haloalkyl, C_-C alkoxy or haloalkoxy C? -C4; 15, particularly preferably hydroxyl, C?-C alco alkoxy, C3-C6 alkenyloxy, C alqu-C4 alkylsulfonyloxy, C alqu ~C-alkylcarbonyloxy, phenylsulphonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately
is partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 4 haloalkoxy; R8, R9 are C? -C4 alkyl; 25, particularly preferably methyl, ethyl, propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R10 is hydrogen or C? -C4 alkyl; particularly preferably C 1 -C 4 alkyl; with particular preference methyl, ethyl or propyl; R11 is hydrogen or C? -C alkyl; particularly hydrogen or methyl. Particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein X is O; R1 is halogen or C4-C4 alkoxy; with halogen being particularly preferred, such as, for example, fluorine, chlorine or bromine, or methoxy or ethoxy; with chlorine or methoxy being very particularly preferred; R6 is halogen, nitro, haloalkyl C: -C4, alkoxy C: -C4 or haloalkoxy Ci-C4; particularly preferably halogen such as, for example, chlorine or bromine, nitro, C?-C 2 haloalkyl, such as, for example, difluoromethyl or trifluoromethyl, C alco-C2 alkoxy or C?-C2 haloalkoxy, such as, for example, difluoromethoxy;
R7 is hydroxyl, alkylsulfonyloxy C.-CO, alkylcarbonyloxy
Ci-Cβ, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can be partially or totally halogenated and / or can carry one of three groups: nitro, cyano, C alquilo-C4 alkyl , haloalkyl C.-C, alkoxy C?
• C or haloalkoxy C? -C4; particularly preferably hydroxyl; R8, Rs are C_-C alkyl; R is hydrogen or C.sub.1 -C alkyl. Particularly preferred are 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R.sup.8 is C.sub.4 -C.sub.4 alkyl, for example, ethyl, 1-methyl-1-ethyl; propyl or butyl; R 9 is C 1 -C 4 alkyl, for example methyl or ethyl; R 10 is hydrogen or C 1 -C alkyl, for example, methyl or ethyl. Also very particularly preferred are the derivatives of 3-15 (heterocyclyl) benzoylpyrazole of the formula I wherein R8 is methyl; R9 is C: ~ C4 alkyl, for example, methyl, ethyl, propyl or butyl; R 10 is C 1 -C 4 alkyl, for example, methyl or ethyl. Also very particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 8, R "are methyl, R 10 is hydrogen. * Also preferred are benzoylpyrazoles substituted by 3-heterocyclyl [sic] of the formula I where:
X is N (C -C6 alkyl); particularly preferably N-methyl, N-ethyl, f | N- (1-methyl-1-ethyl) or N-propyl; R 1 is nitro, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio; 5 with particular preference being given to nitro, halogen or C.sub.4 -C.sub.4 alkoxy; very particularly preferably halogen such as, for example, fluorine, chlorine or bromine, or alternatively C 1 -C 4 alkoxy, such as, for example, methoxy or ethoxy; With chlorine or methoxy being very particularly preferred; R 2, R 3, R 4, R 5 are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methyl-1-ethyl, fluoromethyl or chloromethyl; with hydrogen, methyl, ethyl or f) chloromethyl being particularly preferred; R 6 is halogen, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkyl, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl; with particular preference being given to halogen, for example fluorine, chlorine or bromine, nitro, haloalkyl C.-C4 such as, for example, difluoromethyl or trifluoromethyl, C1-C4 alkoxy such as, for example, methoxy or ethoxy, haloalkoxy C.-C, such as, for example, difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C 1 -C 4 alkylthio, for example methylthio or ethylthio, or C 1 -C 4 alkylsulfonyl,
M for example methylsulfonyl, ethylsulfonyl, 1-methyl-1-ethylsulphonyl or propylsulfonyl; R7 is hydroxyl, Ci-Cß alkoxy, C3-C6 alkenyloxy, Ci-Cß alkylsulfonyloxy, C?-C6 alkylcarbonyloxy, (Cilt-C 4 alkylcarbonyloxy), phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two substituents mentioned can ultimately
is partially or totally halogenated and / or can carry one of three groups: nitro, cyano, C? -C4 alkyl, Ci-C haloalkyl, Ci- C4 alkoxy or C? -C4 haloalkoxy; hydroxyl, C-C4 alkoxy, is particularly preferred,
C 3 -C 6 alkenyloxy, C 1 -C 6 alkylsulfonyloxy, C 1 -C 4 alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two mentioned substituents can be partially or totally halogenated and / or can carry
one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C alkoxy or C 1 -C 4 haloalkoxy; R8, R9 are C? -C4 alkyl; particularly preferably methyl, ethyl,
Propyl, 1-methyl-1-ethyl, butyl, 1-methyl-1-propyl and 2-methyl-1-propyl; R10 is hydrogen or C? -C4 alkyl; ^? particularly preferably C 1 -C 4 alkyl; with methyl, ethyl or propyl being particularly preferred; R11 is hydrogen or C? -C4 alkyl; particularly hydrogen or methyl. Particularly preferred are the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein R 7 is hydroxyl, C 1 -C 6 alkylsulfonyloxy, alkylcarbonyloxy
• 10 Ci-C ?, phenylsulfonyloxy or phenylcarbonyloxy, wherein the phenyl radical of the two aforementioned substituents may be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, alkyl C? -C4, C1.-C4 haloalkyl, C? -C4 alkoxy or C: ~ C4 haloalkoxy; particularly preferably hydroxyl. * Preference is also given to the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I wherein the 20 variables are as defined below: X is 0; R1 is halogen or C4-C4 alkoxy; with fluorine, chlorine, bromine, methoxy or ethoxy being particularly preferred; With chlorine or methoxy being particularly preferred;
R > 2, R, R, R, are hydrogen; R6 is alkylsulfonyl C.-C4; with methylsulfonyl being particularly preferred; R 7 is hydroxyl, C 1 -C 6 alkoxy, C 1 -C 4 -carbonyloxy or phenylcarbonyloxy, wherein the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C.sub.4 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.4 -C.sub.4 haloalkoxy; The hydroxyl, C 1 -C 4 alkoxy, or phenylcarbonyloxy is particularly preferred, wherein the phenyl radical may be partially or fully halogenated and / or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 alkyl, haloalkyl C 1 -C 4, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; R8, R9 are C? -C alkyl; k R10 is hydrogen or C: -C4 alkyl; R11 is hydrogen. The compounds of the formula Ial are particularly preferred (if R 1 = Cl, R 8, R 9 = CH 3, R 10, R 11 = H), in particular the compounds Ial.l.al.300 of Table 1, wherein the Definitions of radicals X and R1 to Ru are of particular importance for the compounds according to the invention, not only in combination with each other, but also in each case, also by themselves.
Table 1: No. X R2 R3 R4 R5
Ial.l 0 H H H H
• 10 Ial.2 0 H H H H
Ial.3 0 H H H H
Ial.4 0 H H H H
Ial.5 0 H H H H
Ial.6 0 H H H H
Ial.7 0 H H H H
lal.8 0 H H H H
lal.9 0 H H H H
• Ial.10 0 H H H H
Ial.ll 0 H H H H
Ial.12 0 H H H H
lal.13 0 H H H H
lal.14 0 H H H H
Ial.15 0 H H H H
lal.16 0 CH3 H H H
lal 17 0 CH3 H H H Ial.18 0 CH3 H H H
Ial.19 0 CH3 H H H H H
• Ial.20 0 CH3 H
lal.21 0 CH3 H H H
lal.22 0 CH3 H H H
Ial.23 0 CH3 H H H
Ial.24 0 CH3 H H H
Ial.25 0 CH3 H H H
lal.26 0 CH3 H H H
• H H
Ial.27 0 CH3 H
Ial.28 0 CH3 H H H
Ial.29 0 CH3 H H H
Ial.30 0 CH3 H H H
Ial.31 0 H H CH3 H
Ial.32 0 H H CH3 H
Ial.33 0 H H CH3 H
Ial.34 0 H H CH3 H
• Ial.35 0 H H CH3 H
Ial.36 0 H H CH3 H
Ial.37 0 H H CH3 H
Ial.38 0 H H CH3 H
Ial.39 0 H H CH3 H
Ial.40 0 H H CH3 H
lal.41 0 H H CH3 H
Ial.42 0 H H CH3 H lal.43 0 H H CH3 H
Ial.44 0 H H CH3 H
• Ial.45 0 H H CH3 H
Ial.46 0 CH3 CH3 H H
Ial.47 0 CH3 CH3 H H
Ial.48 0 CH3 CH3 H H
lal.49 0 CH3 CH3 H H
Ial.50 0 CH3 CH3 H H
Ial.51 0 CH3 CH3 H H
# 10 Ial.52 0 CH3 CH3 H H
Ial.53 0 CH3 CH3 H H
Ial.54 0 CH3 CH3 H H
Ial.55 0 CH3 CH5 H H
Ial.56 0 CH3 CH3 H H
Ial.57 0 CH3 CH3 H H
Ial.58 0 CH3 CH3 H H
lal.59 0 CH3 CH3 H H
• Ial.60 0 CH3 CH3 H H
Ial.61 0 CH3 H CH3 H
Ial.62 0 CH3 H CH3 H
lal.63 0 CH3 H CH3 H
Ial.64 0 CH3 H CH3 H
Ial.65 0 CH3 H CH3 H
Ial.66 0 CH3 H CH3 H
Ial.67 0 CH3 H CH3 H Ial.68 0 CH3 H CH3 H
lal.69 0 CH3 H CH3 H H • lal.70 0 CH3 H CH3
Ial.71 0 CH3 H CH3 H
Ial.72 0 CH3 H CH3 H
Ial.73 0 CH3 H CH3 H
lal.74 0 CH3 H CH3 H
Ial.75 0 CH3 H CH3 H
Ial.76 0 H H CH3 CH3
• CH3 CH3
Ial.77 0 H H
Ial.78 0 H H CH3 CH3
Ial.79 0 H H CH3 CH3
Ial.80 0 H H CH3 CH3
Ial.81 0 H H CH3 CH3
Ial.82 0 H H CH3 CH3
Ial.83 0 H H CH3 CH3
Ial.84 0 H H CH3 CH3
• CH3 CH3
Ial.85 0 H H
Ial.86 0 H H CH3 CH3
Ial.87 0 H H CH3 CH3
Ial.88 0 H H CH3 CH3
Ial.89 0 H H CH3 CH3
Ial.90 0 H H CH3 CH3
Ial.91 0 CH3 CH3 CH3 H
Ial.92 0 CH3 CH3 CH3 H Ial.93 0 CH3 CH3 CH3 H
Ial.94 0 CH3 CH3 CH3 H
• Ial.95 0 CH3 CH3 CH3 H
Ial.96 0 CH3 CH3 CH3 H
Ial.97 0 CH3 CH3 CH3 H
Ial.98 0 CH3 CH3 CH3 H
lal.99 0 CH3 CH3 CH3 H
Ial.100 0 CH3 CH3 CH3 H
Ial.101 0 CH3 CH3 CH3 H
lal.102"0 CH3 CH3 CH3 H
Ial.103 0 CH3 CH3 CH3 H
Ial.104 0 CH3 CH3 CH3 H
Ial.105 0 CH3 CH3 CH3 H
Ial.106 0 CH3 H CH3 'CH3
lal.107 0 CH3 H CH3 CH3
Ial.108 0 CH3 H 'CH3 CH3
Ial.109 0 CH3 H CH3 CH3
• Ial.110 0 CH3 H CH3 CH3
Ial.lll 0 CH3 H CH3 CH3
Ial.112 0 CH3 H CH3 CH3
Ial.113 0 CH3 H CH3 CH3
Ial.114 0 CH3 H CH3 CH3
Ial.115 0 CH3 H CH3 CH3
Ial.116 0 CH3 H CH3 CH3
Ial.117 0 CH3 H CH3 CH3 lal.118 0 CH3 H CH3 CH3
Ial.119 0 CH3 H CH3 CH3
lal.120 0 CH3 H CH3 CH3
• Ial.121 0 CH3 CH3 CH3 CH3
Ial.122 0 CH3 CH3 CH3 CH3
Ial.123 0 CH3 CH3 CH3 CH3
lal.124 0 CH3 CH3 CH3 CH3
Ial.125 0 CH3 CH3 CH3 CH3
lal.126 0 CH3 CH3 CH3 CH3
• CH3
lal.127 0 CH3 CH3 CH3
Ial.128 0 CH3 CH3 CH3 CH3 3
Ial.129 0 CH3 CH3 CH3 CH
Ial.130 0 CH3 CH3 CH3 CH3
Ial.131 0 CH3 CH3 CH3 CH3
Ial.132 0 CH3 CH3 CH3 CH3
lal.133 '0 CH3 CH3 CH3 CH3
Ial.134 0 CH3 CH3 CH3 CH3
• Ial.135 0 CH3 CH3 CH3 CH3
lal.136 0 CH2C1 H H H
Ial.137 0 CH2C1 H H H
Ial.138 0 CH2C1 H H H
Ial.139 0 CH2C1 H H H
• lal.140 0 CH2C1 H H H
lal.141 0 CH2C1 H H H
Ial.142 0 CH2C1 H H H Ial.143 0 CH2C1 H H H
Ial.144 0 CH2C1 H H H
0 CH2C1 H H HALL.145 LA.146 0 CH2C1 H H H
Ial.147 0 CH2C1 H H H
Ial.148 0 CH2C1 H H H
Ial.149 0 CH2C1 H H H
Ial.150 0 CH2C1 H H H H LAL.151 NCH3 H H H
Ial.152 NCH3 H H H H
Ial.153 NCH3 H H H H
Ial.154 NCH3 H H H H
lal.155 NCH3 H H H H
Ial.156 NCH3 H H H H
Ial.157 NCH3 H H H H
'Ial.158 NCH3 H H H H
Ial.159 NCH3 H H H H
lal.160 NCH3 H H H H
Ial.161 NCH3 H H H H
Ial.162 NCH3 H H H H
Ial.163 NCH3 H H H H
Ial.164 NCH3 H H H H
Ial.165 NCH3 H H H H
Ial.166 NCH3 CH3 H H H
Ial.167 NCH3 CH3 H H H Ial.168 NCH3 CH3 H H H
Ial.169 NCH3 CH3 H H H
Ial.170 NCH3 CH3 H H H
• Ial.171 NCH3 CH3 H H H
Ial.172 NCH3 CH3 H H H
Ial.173 NCH3 CH3 H H H
Ial.174 NCH3 CH3 H H H
Ial.175 NCH3 CH3 H H H
Ial.176 NCH3 CH3 H H H
• 10 Ial.177 NCH3 CH3 H H H
Ial.178 NCH3 CH3 H H H
Ial.179 NCH3 CH3 H H H
Ial.180 NCH3 CH3 H H H
Ial.181 NCH3 H H CH3 H
Ial.182 NCH3 H H CH3 H
Ial.183 NCH3 H H CH3 H
Ial.184 NCH3 H H CH3 H
Ial.185 NCH3 H H CH3 H
Ial.186 NCH3 H H CH3 H
Ial.187 NCH3 H H CH3 H
Ial.188 NCH3 H H CH3 H
Ial.189 NCH3 H H CH3 H
Ial.190 NCH3 H H CH3 H
Ial.191 NCH3 H H CH3 H
Ial.192 NCH3 H H CH3 H Ial.193 NCH3 H H CH3 H
Ial.194 NCH3 H H CH3 H
Ial.195 NCH3 H H CH3 H lal.196 NCH3 CH3 CH3 H H
Ial.197 NCH3 CH3 CH3 H H
Ial.198 NCH3 CH3 CH3 H H
Ial.199 NCH3 CH3 CH3 H H
Ial.200 NCH3 CH3 CH3 H H
Ial.201 NCH3 CH3 CH3 H H
• 10 Ial.202 NCH3 CH3 CH3 H H
Ial.203 NCH3 CH3 CH3 H H lal.204 NCH3 CH3 CH3 H H
Ial.205 NCH3 CH3 CH3 H H
Ial.206 NCH3 CH3 CH3 H H
Ial.207 NCH3 CH3 CH3 H H
Ial.208 NCH3 CH3 CH3 H H
Ial.209 NCH3 CH3 CH3 H H
• Ial.210 NCH3 CH3 CH3 H H
Ial.211 NCH3 CH3 H CH3 H
Ial.212 NCH3 CH3 H CH3 H lal.213 NCH3 CH3 H CH3 H
Ial.214 NCH3 CH3 H CH3 H
Ial.215 NCH3 CH3 H CH3 H
Ial.216 NCH3 CH3 H CH3 H
lal.217 NCH3 CH3 H CH3 H Ial.218 NCH3 CH3 H CH3 H
lal.219 NCH3 CH3 H CH3 H
lal.220 NCH3 CH3 H CH3 H
lal.221 NCH3 CH3 H CH3 H
, Ial.222 NCH3 CH3 H CH3 H
lal.223 NCH3 CH3 H CH3 H
lal.224 NCH3 CH3 H CH3 H
Ial.225 NCH3 CH3 H CH3 H
Ial.226 NCH3 H H CH3 CH3
• 0 lal.227 NCH3 H H CH3 CH3
Ial.228 NCH3 H H CH3 CH3
Ial.229 NCH3 H H CH3 CH3
Ial.230 NCH3 H H CH3 CH3
Ial.231 NCH3 H H CH3 CH3
.5 lal.232 NCH3 H H CH3 CH3
Ial.233 NCH3 H H CH3 CH3
lal.234 NCH3 H H CH3 CH3
• lal.235 NCH3 H H CH3 CH3
Ial.236 NCH3 H H CH3 CH3
lal.237 NCH3 H H CH3 CH3
lal.238 NCH3 H H CH3 CH3
Ial.239 NCH3 H H CH3 CH3
lal.240 NCH3 H H CH3 CH3
Ial.241 NCH3 CH3 CH3 CH3 H
Ial.242 NCH3 CH3 CH3 CH3 H Ial.243 NCH3 CH3 CH3 CH3 H
lal.244 NCH3 CH3 CH3 CH3 H
Ial.245 NCH3 CH3 CH3 CH3 H
• Ial.246 NCH3 CH3 CH3 CH3 H
Ial.247 NCH3 CH3 CH3 CH3 H
Ial.248 NCH3 CH3 CH3 CH3 H
lal.249 NCH3 CH3 CH3 CH3 H
lal.250 NCH3 CH3 CH3 CH3 H
lal.251 NCH3 CH3 CH3 CH3 H
lal.252 NCH3 CH3 CH3 CH3 H
Ial.253 NCH3 CH3 CH3 CH3 H
Ial.254 NCH3 CH3 CH3 CH3 H
Ial.255 NCH3 CH3 CH3 CH3 H
Ial.256 NCH3 CH3 H CH3 CH3
lal.257 NCH3 CH3 H CH3 CH3
Ial.258 NCH3 CH3 H CH3 'CH3
Ial.259 NCH3 CH3 H CH3 CH3
• Ial.260 NCH3 CH3 H CH3 CH3
Ial.261 NCH3 CH3 H CH3 CH3
Ial.262 NCH3 CH3 H CH3 CH3
Ial.263 NCH3 CH3 H CH3 CH3
Ial.264 NCH3 CH3 H CH3 CH3
Ial.265 NCH3 CH3 H CH3 CH3
Ial.266 NCH3 CH3 H CH3 CH3
Ial.267 NCH3 CH3 H CH3 CH3 Ial.268 NCH3 CH3 H CH3 CH3
Ial.269 NCH3 CH3 H CH3 CH3
Ial.270 NCH3 CH3 H CH3 CH3
Ial.271 NCH3 CH3 CH3 CH3 CH3
Ial.272 NCH3 CH3 CH3 CH3 CH3
Ial.273 NCH3 CH3 CH3 CH3 CH3
Ial.274 NCH3 CH3 CH3 CH3 CH3
Ial.275 NCH3 CH3 CH3 CH3 CH3
Ial.276 NCH3 CH3 CH3 CH3 CH3
• 10 Ial.277 NCH3 CH3 CH3 CH3 CH3
Ial.278 NCH3 CH3 CH3 CH3 CH3
Ial.279 NCH3 CH3 CH3 CH3 CH3
Ial.280 NCH3 CH3 CH3 CH3 CH3
Ial.281 NCH3 CH3 CH3 CH3 CH3
Ial.282 NCH3 CH3 CH3 CH3 CH3
Ial.283 NCH3 CH3 C'H3 CH3 CH3
Ial.284 NCH3 CH3 CH3 CH3 CH3
• Ial.285 NCH3 CH3 CH3 CH3 CH3
Ial.286 NCH3 CH2C1 H H H
Ial.287 NCH3 CH2C1 H H H
Ial.288 NCH3 CH2C1 H H H
- Ial.289 NCH3 CH2C1 H H H
Ial.290 NCH3 CH2C1 H H H
Ial.291 NCH3 CH2C1 H H H
Ial.292 NCH3 CH2C1 H H H Ial.293 NCH3 CH2C1 H H H
Ial.294 NCH3 CH2CI H H H H H
• Ial.295 NCH3 CH2C1 H Ial.296 NCH3 CH2C1 H H H
Ial.297 NCH3 CH2C1 H H H
Cal.298 NCH3 CH2C1 H H H
Ial.299 NCH3 CH2C1 H H H
Ial.300 NCH3 CH2C1 H H H
No. Rd R7 • 10 Ial.l SCH3 OH Ial.2 SCH2CH3 OH Ial.3 S02CH3 OH Ial.4 SO2CH2CH; OH Ial.5 S02CH (CH 3) 2 OH 15 Ial.6 S02 (CH2) to CH3 OH Ial.7 Cl OH Ial.8 Br OH • Ial.9 N02 OH Ial.10 CHF2 OH 20 Ial.ll CF3 OH Ial .12 OCH3 OH Ial.13 OCH2CH3 OH
Ial.15 OCF3 OH 25 lal.16 SCH3 OH Ial.17 SCH2CH3 OH
Ial.18 SO2CH3 OH
Ial.19 SO2CH2CH3 OH
• Ial.20 S02CH (CH3) 2 OH
Ial.21 S02 (CH2) 2CH3 OH
Ial.22 Cl OH
Ial.23 Br OH
Ial.24 N02 OH
Ial.25 CHF2 OH
• 10 Ial.26 CF3 OH
Ial.27 OCH3 OH
Ial.28 OCH2CH3 OH
Ial.29 OCHF2 OH 15 Ial.31 SCH3 OH
Ial.'32 SCH2CH3 OH
Ial.33 SO2CH3 OH
Ial.35 S02CH (CH3) 2 OH
Ial.36 S02 (CH2) 2CH3 OH
Ial.37 Cl OH
Ial.38 Br OH
Ial.39 N02 OH
Ial.40 CHF2 OH
Ial.41 CF3 OH Ial.42 0CH3 OH
Ial.43 OCH2CH3 OH
Ial.45 OCF3 OH
Ial.46 SCH3 OH
Ial.48 S02CH3 OH
Ial.50 S02CH (CH3) 2 OH
• 10 Ial.51 S02 (CH2) 2CH3 OH
Ial.52 Cl OH
Ial.53 Br OH
Ial.54 NO2 OH
Ial.55 CHF2 OH
Ial.56 CF3 OH
Ial.57 0CH3 OH
Ial.58 OCH2CH3 OH
Ial.59 OCHF2 OH
Ial.60 OCF3 OH
Ial.61 SCH3 OH
Ial.62 SCH2CH3 OH
Ial.64 S02CH2CH3 OH
Ial.65 S02CH (CH3) 2 OH
Ial.66 SO: (CH2) 2CH3 OH Ial.67 Cl OH
Ial.68 Br OH
Ial.69 N02 OH
lal.70 CHF2 OH
Ial.71 CF3 OH
Ial.72 OCH3 OH
Ial.73 OCH2CH3 OH
lal.74 OCHF? OH
lal.75 OCF3 OH
• 10 Ial.76 SCH3 OH
lal.77 SCH2CH2 OH
lal.79 SO2CH2CH3 OH
lal.80 S02CH (CH3): OH
Ial.81 S02 (CH2) 2CH3 OH
Ial.82 Cl OH
Ial.83 Br OH
• Ial.84 N0 OH
Ial.85 CHF2 OH
Ial.86 CF3 OH
Ial.87 OCH3 OH
Ial.88 OCH2CH3 OH
lal.90 OCF3 OH
Ial.91 SCH3 OH Ial.92 SCH2CH3 OH
Ial.93 S02CH3 OH
Ial.94 S02CH2CH3 OH
Ial.95 S02CH (CH3) 2 OH
Ial.96 S02 (CH2) 2CH3 OH
Ial.97 Cl OH
Ial.98 Br OH
lal.99 N02 OH
Ial.100 CHF2 OH
Ial.101 CF3 OH
Ial.102 OCH3 OH
Ial.103 OCH2CH3 OH
Ial.104 OCHF2 OH
Ial.106 SCH3 OH
Ial.110 S02CH (CH3) 2 OH
Ial.lll S02 (CH2) 2CH3 OH
Ial.112 Cl OH
Ial.113 Br OH
Ial.114 N02 OH
Ial.115 CHF2 OH
Ial.116 CF3 OH Ial.1.117 OCH3 OH Ial. .118 OCH2CH3 OH Ial. .119 OCHF2 OH
• Ial. .120 OCF3 OH 5 Ial .121 SCH3 OH Ial .122 SCH2CH3 OH Ial. .123 SO2CH3 OH Ial, .124 SO2CH2CH3 OH Ial. .125 S02CH (CH3) 2 OH
• 10 Ial, .126 S02 (CH2) 2CH3 OH Ial. .127 Cl OH Ial. .128 Br OH Ial. .129 N02 OH Ial. .130 CHF2 OH 15 Ial. .131 CF3 OH Ial, .132 OCH3 OH •
Ial. , 133 OCH2CH3 OH
• Ial. .134 OCHF2 OH Ial. .135 OCF3 OH 20 Ial. .136 SCH3 OH Ial. , 137 SCH2CH3 OH Ial. , 138 SO2CH3 OH Ial. , 139 S02CH2CH3 OH Ial. , 140 S02CH (CH3) 2 OH 25 Ial. 141 S02 (CH2) 2CH3 OH la.142 Cl OH
Ial.143 Br OH
Ial.144 N02 OH
Ial.145 CHF2 OH
Ial.146 CF3 OH
Ial.147 OCH3 OH Ial.149 OCHF2 OH
Ial.150 OCF3 OH
Ial.151 SCH3 OH
Ial.152 SCH2CH3 OH
Ial.153 S02CH3 OH
Ial.154 SO2CH2CH; OH
Ial.155 S02CH (CH3) 2 OH
Ial.156 S02 (CH2¡ 2CH3 OH
Ial.157 Cl OH
Ial.158 Br OH
Ial.159 N02 OH
Ial.160 CHF2 OH
Ial.161 CF3 OH
Ial.162 OCH3 OH
Ial.163 OCH2CH3 OH
Ial.164 OCHF2 OH
Ial.165 OCF3 OH
Ial.166 SCH3 OH Ial.170 S02CH (CH3) 2 OH
Ial.171 S02 (CH2) 2CH3 OH
Ial.172 Cl OH
Ial.173 Br OH
Ial.174 N02 OH
Ial.175 CHF2 OH
Ial.176 CF3 OH
Ial.177 OCH3 OH
Ial.179 OCHF; OH
Ial.180 OCF3 OH
Ial.181 SCH3 OH
Ial.183 SO: CH3 OH
• Ial.184 SO; CH2CH3 OH
Ial.186 S02 (CH2) 2CH3 OH
Ial.187 Cl OH
Ial.188 Br OH
Ial.189 N02 OH
Ial.190 CHF: OH
Ial.191 CF3 OH Ial.192 OCH3 OH
Ial.193 OCH2CH3 OH
Ial.194 OCHF2 OH
• Ial.195 OCF3 OH
Ial.196 SCH3 OH
Ial.199 SO2CH2CH3 OH
Ial.200 S02CH (CH3) 2 OH
• 10 Ial.201 S02 (CH2) 2CH3 OH
Ial.202 Cl OH
Ial.203 Br OH lal.204 N02 OH
Ial.205 CHF2 OH
Ial.206 CF3 OH
Ial.207 OCH3 OH
Ial.208 OCH2CH3 OH
Ial.209 OCHF2 OH
Ial.210 OCF3 OH
Ial.211 SCH3 OH
Ial.212 SCH2CH3 OH
Ial.213 SO2CH3 OH
Ial.215 S02CH (CH3) 2 OH
Ial.216 S02 (CH2) 2CH3 OH Ial.217 Cl OH
Ial.218 Br OH
• Ial.219 N02 OH
Ial.220 CHF2 OH
Ial.221 CF3 OH
Ial.222 OCH3 OH
Ial.223 OCH2CH3 OH
Ial.224 OCHF2 OH
Ial.226 SCH3 OH
Ial.228 S02CH3 OH
Ial.229 S02CH: CH3 OH
Ial.230 S02CH (CH3); OH
Ial.231 S02 (CH2) 2CH3 OH
Ial.232 Cl OH
Ial.233 Br OH
• Ial.234 N02 OH
Ial.235 CHF2 OH
Ial.236 CF3 OH
Ial.237 OCH3 OH
Ial.240 OCF3 OH
Ial.241 SCH3 OH Ial.243 SO2CH3 OH
Ial.244 S02CH2CH3 OH
^ Ial.245 S02CH (CH3) 2 OH
Ial.246 S02 (CH2) 2CH3 OH
Ial.247 Cl OH
Ial.248 Br OH
Ial.249 N02 OH
Ial.250 CHF2 OH
Ial.251 CF3 OH
Ial.252 OCH3 OH
Ial.253 OCH2CH3 OH
Ial.255 OCF3 OH
Ial.256 SCH3 OH
Ial.260 S02CH (CH3) 2 OH
Ial.261 S02 (CH2) 2CH3 OH
Ial.262 Cl OH
Ial.263 Br OH
Ial.264 N02 OH
Ial.265 CHF2 OH
Ial.266 CF3 OH lal.267 0CH3 OH
Ial.268 OCH2CH3 OH
Ial.269 OCHF2 OH
• 5 Ial.271 SCH3 OH
lal.272 SCH2CH3 OH
Ial.273 S02CH3 OH
Ial.274 SO2CH2CH3 OH
Ial.275 S02CH (CH3) 2 OH
lal.276 SO: (CH2) 2CH3 OH
lal.277 Cl OH
Ial.278 Br OH
Ial.279 N0 OH
Ial.280 CHF2 OH
Ial.281 CF3 OH
Ial.283 OCH2CH3 OH
• Ial.284 OCHF2 OH
Ial.285 OCF3 OH
Ial.286 SCH3 OH
Ial.287 SCH2CH3 OH
Ial.288 SO2CH3 OH
Ial.289 SO2CH2CH3 OH
Ial.290 S02CH (CH3) 2 OH
Ial.291 S02 (CH2) 2CH3 OH Ial.292 Cl OH Ial.293 Br OH Ial.294 NO: OH Ial.295 CHF OH lal.296 CF3 OH Ial.297 OCH 3 OH Ial.298 OCH: CH3 OH Ial .299 OCKF2 OH Ial.300 OCF3 OH Extraordinary preference is also given to the compounds of formula Ia2, particularly to compounds Ia2.1 to Ia2.300, which differ from the corresponding compounds Ial.300 because R1 * is methyl.
The compounds of the formula Ia3, particularly the compounds Ia3.1 to Ia3.300, which differ from the compounds Zal.l to Ial.300 in which R8 is ethyl, are also preferred in an extraordinary manner.
The compounds of the formula Ia4, in particular the compounds Ia4.1 to Ia4.300, which differ from the compounds Ial.l to Ial.300 in
• that R "is ecilo and R11 is methyl.
fifteen
• The compounds of the formula Ia5, particularly the compounds Ia5.1 to Ia5.300, which differ from the compounds Ial.l to Ial.300 in
that R8 is 1-methyl-l-ethyl.
The compounds of the formula Ia6, particularly the compounds Iaß.la Ia6.300, which differ from the compounds Ial.3la in which R8 is 1-methyl-1-ethyl and R11 is methyl, are also particularly preferred. .
The compounds of the formula Ia7, particularly the compounds Ia7.1 to Ia7.300, which differ from the compounds Ial.l to Ial.300 in which R10 is methyl, are particularly preferred. fifteen
The compounds of the formula Ia8, particularly the Iad compounds, are also preferred in an extraordinary manner. l to Ia8. 300, which differ from the compounds Ial. l to Ial. 300 in
that R10 is methyl or and Ru is methyl.
H3C CH3 CH3
The compounds of the formula Ia 9, particularly the compounds Ia9.1 to Ia9,300, which differ from the compounds Ial.l to Ial.300 in
• that Rr and R5 are 1-methyl-l-ethyl.
The compounds are also preferred in an extraordinary way
• of the formula IalO, particularly the compounds IalO.l to IalO.303, which differ from Ic.l. to Ial.sub.300 where R "and R9 are 1-methyl-l-ethyl and?." It is methyl. twenty
H3C CH3 Also desirably preferred are compounds of the formula Iall, particularly compounds Iall.l to Iall.300, which differ from compounds Ial.l to Ial.300 where R8 is ethyl and R "is methyl.
H3C CH2CH3 CB3 • 10 The compounds of the formula Ial2, particularly the compounds Ial2.1 to Ial2.300, which differ from the corresponding compounds Ial.300 in which R8 is ethyl and R "and R11 are methyl.
The compounds of the formula Ial3, particularly the compounds Ial3.1 to I3.300, which differ from the compounds Ial.I to I.300 where R1 is methoxy, are also particularly preferred. The compounds of the formula Ial4, particularly the compounds Ial4.1 to Ial4.300, which differ from the corresponding compounds, are also particularly preferred.
• Ial.l to Ial.300 where R ~ is methoxy and R11 is methyl. 10
Compounds are also preferred in an extraordinary way
• of the formula Ial5, particularly the compounds Ial5.1 to Ial5.300, which differ from the compounds Ial.l to Ial.300 where R1 is methoxy and R8 is ethyl. twenty
The compounds of the formula Ial6, particularly the compounds Ial.sub.1 to 6,300, which differ from the compounds Ial.l to I.sub.300 in crue R.sub.1 is methoxy, R.sub.8 is ethyl and Ru is methyl are also particularly preferred.
The compounds of the formula Ial7 are also particularly preferred, particularly the compounds Ial7.1 to I7.700, which differ from the compounds Ial.300 where R1 is methoxy and R8 is 1-methyl-l- ethyl. fifteen
CH:
The compounds of the formula Iald, particularly the compounds Iald.l to Ial8.300, which differ from the compounds Ial.l to Ial.300 in
that R1 is methoxy, R8 is 1-mecyl-l-ethyl and Ru is methyl.
The compounds of the formula Ial9, particularly the compounds Ial9.1 to Ial9.300, which differ from the compounds Ial.l to Ial.300 in
• that R1 is -ethoxy and R10 is methyl.
The compounds of formula Ia20, particularly compounds Ia20.1 to Ia20.300, which differ from the compounds Ial.3la in which R1 is netoxy, R10 is methyl and R ~ are also preferred in an extraordinary manner. ~ It's methyl.
Compounds are also preferred in an extraordinary way
• of the formula Ia21, particularly the compounds Ia21.1 to Ia21.3CQ, which differ from the compounds Ial.l to Ial.300 in which R: is methoxy and R8 and R9 are l-netyl-l-ethyl.
The compounds of the formula Ia22, in particular the compounds Ia22.1 to Ia22.310, which differ from the compounds Ial.la.al.30C in which R1 is methoxy, R8 and R9 are 1-methyl, are also particularly preferred. -l-ethyl and Ru is methyl.
fifteen
H3C CH3
The compounds of formula Ia23 are also particularly preferred, particularly compounds Ia23.1 to Ia23.3; 0, which differ from compounds Ial.l to Ial.30C in
that R "is methoxy, R8 is ethyl and R ~" is methyl.
The compounds of the formula Ia24, particularly the compounds Ia24.1 to Ia24,300, which differ from the compounds Ial.l.3".. in (in which Rz is methoxy, R8 is ethyl and R10 and Rn are methyl.
The 3- (heterocyclyl) benzoylpyrazole derivatives of the formula
• I can be obtained by several ways, for example, for the following processes. Process A: Reaction of pyrazoles of the formula II with an activated benzoic acid Illa or an activated benzoic acid Il lß, preferably activated in situ, to provide the corresponding acylation product IV, followed by rearrelation, which allows the obtaining of compounds of the formula I in
where R7 = OH.
•
twenty
I wherein R = OH L1 is a nucleophilically replaceable leaving group such as for example halogen, for example bromine, chlorine, hetaryl such as for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc. The activated benzoic acid can be used directly, as for example in the case of benzoyl halides, or can be generated in situ, for example, using dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole, etc. . It may be advantageous to effect the acylation reaction in the presence of a base. The reagents and the auxiliary base are used profitably in equimolar amounts here. A slight excess of auxiliary base, for example, from 1.2 to 1.5 molar equivalents, based on II, may be of benefit in some cases. Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable for use as solvents are, for example, chlorinated hydrocarbons such as, for example, methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, ethers such as, for example, diethyl ether, methyltert-butyl ether, dimethoxyethane, tetrahydrofuran. , dioxane, polar aprotic solvents such as for example acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters such as for example ethyl acetate, or mixtures thereof. If the activated carboxylic acid component employing benzoyl halide, it may be advantageous to cool the reaction mixture to a temperature of 0 to 10 ° C when this reaction partner is added. The mixture is subsequently stirred at a temperature of 20-100 ° C, preferably at 25-50 ° C, until the completion of the reaction. The treatment is carried out in a conventional manner, for example, by emptying the reaction mixture in water and extracting the valuable product. Solvents particularly suitable for this purpose are methylene chloride, diethyl ether, dimethoxyethane and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be used for rearrangement without further purification. The rearrangement of the esters to provide the compounds of the formula I is advantageously effected at a temperature of 20-40 ° C in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst. Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, dimethoxyethane, toluene or mixtures thereof. Preferred solvents are acetonitrile and dioxane.
Suitable bases are tertiary amines such as for example triethylamine or pyridine, or carbonates of alkaline B metals, such as sodium carbonate or potassium carbonate, which are preferably used in an equimolar amount or up to a four-fold excess, based on the ester. Preference is given to the use of triethylamine or alkali metal carbonates, preferably twice the equimolar amount, based on the ester. Suitable cyano compounds are inorganic cyanides such
• 10 as sodium cyanide and potassium cyanide, and cyano organic compounds, such as acetonanohydrin and trimethylsilyl cyanide. They are used in an amount of 1 to 50 mol%, based on the ester. Preference is given to the use of acetonanohydrin or trimethylsilyl cyanide, for example,
in an amount of 5 to 15, preferably 10 mol%, based on the ester. The treatment can be carried out in a manner known per se. The reaction mixture, for example, is acidified with dilute mineral acid, such as hydrochloric acid, for example.
% or sulfuric acid, and extracted with organic solvent, for example, methylene chloride or ethyl acetate. The organic extract can be extracted by a 5-10% alkali metal carbonate solution, for example, a solution of sodium carbonate or potassium carbonate. The
The aqueous phase is acidified and the resulting precipitate is removed by filtration with suction and / or extracted with netylene chloride or ethyl acetate, and the mixture is dried and concentrated. (Examples for the preparation of hydroxypyrazole esters and for the rearrangement of esters are provided, for example, in EP-A 282 944 and US 4 643 757). However, it is also possible to generate the "acylation product" IV in situ by reaction of a pyrazole of the formula II, or an alkali metal sai of the -ism,
• 10 with a derivative of 3- (heterccyl) benzene of the formula V in the presence of carbon monoxide, a catalyst and a base.
[catal i zador]
• Base
L2 is a leaving group such as, for example, halogen, for example chlorine, bromine or iodine, or sulfonate, such as, for example, p-mesylate or triflate; preferably bromine or triflate. The "acylation product" IV reacts directly or indirectly to provide the 3- (heterocyclyl) benzoylpyrazole derivative of the formula I. Suitable catalysts are palladium-ligand complexes wherein the palladium is present in the state of
^^ oxidation 0, metallic palace that has been optionally
absorbed in a vehicle, and preferably palladium salts
(II). The reaction with palladium (II) salts and metallic palladium is preferably carried out in the presence of complex ligands. An example of a complex paladic (0) - matching right is
tetrakis (triphenylphosphine) palladium. Palladium metalize is preferably absorbed in an inert carrier such as activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of ligands
of complex such as for example triphenylphosphine. Examples of suitable palladium (II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as for example triphenylphosphine is preferred. Suitable complex ligands for the palladium-ligand complexes or in the presence of which the reaction is preferably carried out with palladium metal or palladium salt (I I), are phosphines whose structure is represented by the following formulas:
R «Rd \ Rf P? B - ((CCHH2,) 2 - P < / Re \ R9
in dor.c z is from 1 to 4 and the radicals Ra to Rg are C- • C6 alkyl, C3-C6-chloroalkyl, C5-C2 arylalkyl, or
preference, arilo. For example, aryl is naphthyl and unsubstituted or substituted feryl, such as 2-tolyl and, particularly, unsubstituted phenyl. Complex palladium salts can be prepared in a manner known per se starting from palladium salts
commercially available eats for example paladic chloride or palladium acetate and the appropriate phosphines as
• for example triphenylphosphine or 1,2-bis (diphenylphosphino) ethane. Many of the palladium salts that form complexes are also commercially available.
The preferred palladium salts are [(R) (+) 2,2'-bis (diphenylphosphino) -1, 1'-cobaltii chloride. -palladium (II), bis (triphenylphosphine) palladium (II) acetate and, in particular, bis (triphenylphosphine) palladium (II) chloride. The palladium catalyst is usually used in a
concentration of 0.05 to 5 mol%, and preferably 1 to 3 mol%. Suitable bases are tertiary amines such as, for example, N-methyl-piperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Alkali metal carbonates are also suitable, such as, for example, sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable. In general, 2 to 4 molar equivalents are used,
• particularly 2 molar equivalents of the alkali metal carbonate and 1 to 4 molar equivalents, particularly 2 molar equivalents, of the tertiary amine, based on the 3- (heterocyclyl) -benzene derivatives of the formula V. 15 Solvents suitable are nitriles such as benzonitrile and acetonitrile, amides, for example dimethylformamide, dimethylacetamide, tetraalkyl C? -C4-ureas,
• or N-methylpyrrolidone and, preferably, ethers such as tetrahydrofuran and methyltert-butyl ethers. HE
particularly prefer ethers such as for example 1,4-dioxane and dimethoxyethane. Process B: Compounds of the formula I wherein R is different from hydroxyl are obtained by the reaction of compounds of
The formula I wherein R7 = hydroxyl with alkylating agents, sulfonylating agents or acylating agents L3-R7a (VI) •
# 10 I where R7 = OH VI I where R7 = OR a (= R7 other than OH) ~ is a nucleophically replaceable leaving group such as by halogen such as, for example, bromine or chlorine, acyloxy,
for example, acetyloxy or ethylcarbonyloxy, or alkylsulfonyloxy, for example, methylsulfonyloxy or
• trifluoromethylsulfonyloxy. R a is C 1 -C 5 alkyl, C 3 -C 6 alkenyl, C 1 -C 6 alkylsulfony, C 1 -C 6 alkylcarbonyl. , (alkylthio) C? -C4-carbonyl,
Phenylsulfonyl or phenylcarbonyl, wherein the phenyl radical of the two substituents mentioned can ultimately be partially or totally halogenated and / or can carry one to three of the following groups: nitro, cyano, C? -C4 alkyl, haloalkyl C? ? -C4, C: ~ C4 alkoxy or
Haloalkoxy C? -C4.
The compounds of formula VI can be used directly, for example, in the case of sulphonyl halides or sulfonic anhydrides, or can be generated in situ, for example, activated sulfonic acids (using sulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc.). The initial materials are generally used in equimolar quantities. However, it may be helpful to also use an excess of one or another component. 10 If appropriate, it may be helpful to effect the reaction in the presence of a base. The reagents and the auxiliary base are used profitably in equimolar amounts. An excess of auxiliary base, for example, from 1.5 to 3 molar equivalents, based on I, may be of benefit in certain
cases Suitable auxiliary bases are tertiary alkylamines, such as flk for example triethylamine, pyridine, alkali metal carbonates such as, for example, sodium carbonate or potassium carbonate, and alkali metal hydrides, for example hydride
of sodium. Preference is given to the use of triethylamine and pyridine. Suitable solvents are, for example, chlorinated hydrocarbons, such as, for example, methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, for example
Toluene, xylene, chlorobenzene, ethers, such as for example diethyl ether, methyltert-butyl ether, tetrahydrofuran and dioxane, polar aprotic solvents, for example acetonitrile, ip dimethylformamide, dimethyl sulfoxide, or esters, such as for example ethyl acetate or mixture thereof. In general, the temperature of the reaction is within a range of 0 ° C to the boiling point of the reaction mixture. The treatment may be carried out in a manner known per se ^^ to provide the product. 10 The pyrazoles of formula II used as materials
. initials are known or can be prepared through the process known per se (for example, EP-A 240 001 and J. Prakt. Chem. 315, 383 (1973)). Activated benzoic acids Illa can be obtained from
way known per se from the benzoic acids Illß. The latter, on the other hand, are obtained by hydrolysis from the corresponding esters VII. May
• prepared by converting an oxime or hydrazone of formula VIII to the hydroxamic acid halide
, particularly hydroxamic acid chloride or carbohydrazide halide, particularly carbohydrazide chloride; generating a nitrile oxide or nitrile imine in situ and reacting this with an alkene (see, for example, Chem. Ber. 106, 3258-3274 (1973)). 25 VII
VIII
Hydrolysis
inß
L4 indicates an alkoxy radical C.-Ce. However, the Illß benzoic acids can also be obtained by converting an oxime or hydrazine of the formula IX into the corresponding r-ityl oxides and
by reacting them with alquer.es to provide the corresponding cycloaddition products (see, for example, Chem. Ber. 106, 3258-3274, 1973)). Accordingly, for example, the oxime of formula IX (X = 0) is oxidized with sodium hypochlorite and reacted with a suitable alkene
in an inert solvent such as for example methylene chloride, chloroform, tetrahydrofuran, dioxane or acetonitrile. The product is then converted into the presence of a catalyst and
• a base in the benzoic acid Illß using carbon monoxide and water.
IX CC, H20 [catalyst]
Illß
L2 refers to a leaving group, for example halogen, for example, chlorine, bream or iodine, or sulfonate, such as, for example, mesylate or triflaco, preferably bromine c-triflate.
With regard to the carbonylation reaction, what has been said above is applied analogously. Preparation Examples 4- [2-chloro-3- (4,5-dihydrcisoxazol-3-yl) -4-methylsulfonylbenzyl] -5-hydroxy-1- (1,1-dimethyl-1-ethyl) -1H- pyrazole • (Compound 2.1) 2.32 g (0.02 mol) of 1- (1,1-dimethyl-1-ethyl) -5-5-hydroxy-1H-pyrazole and 2.3 g (0.02 mol) of potassium carbonate were added to a 5.4 g (0.02 mol) solution of 2-chloro-3- (4,5-dihydroisoxazil-3-yl) -4-methylsulfonylberozoic chloride in 100 ml of ethylene glycol dimethyl ether, and the mixture was stirred
^ fc during the night. The mixture was subsequently subjected to
After refluxing for 3 hours, the solvent was removed by distillation, the residue was taken up in 300 ml of water and washed with methylene chloride, and the aqueous phase was acidified to pH = .3 using 10% hydrochloric acid. The precipitate was removed by filtration cor. suction and drying 15 to 40 ° C. This gave 4.6 g (65% theoretical level) of 4- [2-chloro-3- (4,5-dihydroisoxazol-3-yl) -4-methylsulfonylbenzyl] -5-hydroxy -l- (1,1-dimethyl-l-ethyl) -1H-pyrazole] In addition to the above compound, table 2 presents a list of other benzoylpyrazoles substituted by 3- (heterocyclyl) of the formula I which were prepared either that can be prepared in a similar way.
I dcnde X = 0
Table 2: No. R1 R2 R3 R4 R5 R6 R7
• 2.1 Cl HHHH S02CH3 OH 2.2 Cl HHHH S02CH3 OH 5 2.3 Cl HHHH S02CH3 OCH (CH3) 2 2.4 Cl HHHH SO2CH3 OCH2CH3 2.5 Cl HHHH S02CH3 0CH3 2.6 Cl HHHH SO: CH3 OCO [3-F-C6H4] 2.7 Cl HHHH SO; CH3 OCOC6H5 • 10 2.8 Cl HHH n S0 CH3 OCO [3,5-F: -C6H3] 2.9 Cl HHHH S02CH3 OH 2.10 Cl HHHH SO-.CH3 OCH (CH3) 2 2.11 Cl HHHH S0: CH3 OCOC6H5 2.12 Cl HHHH S02CH3 OCO (3-F-C6H4] 15 2.13 OCH3 HHHH SO2CH3 OH 2.14 0CH3 HHHH S02CH3 OCOSCH3
2. 16 Cl H H H H S02CH3 OCH3 2.17 Cl H H H S02CH3 OCH2H5 20 2.18 OCH3 H H H S02CH3 OCO [3-F-C6H4] No. R8 R9 R: o R: Data: 5 physicists p.f. [° C] XH- -NMR [d in ppm] 2.1 CH3 CH3 CH3 H 198-200 2.2 CH3 CH3 H H 210-215 25 2.3 CH3 CH3 H H 175-180 2.4 CH3 CH3 H H 150-155 2.5 CH3 CH3 H H 185-190
• 2.6 CH3 CH3 HH 225-230 2.7 CH3 CH3 HH 220 225 2.8 CH3 CH3 HH 220-225 2.9 CH (CH3) 2 CH3 HH 150-155 2.10 CH (CH3) 2 CH3 HH 125-130 2.11 CH (CH3) 2 CH3 HH 135-140 2.12 CH (CH3) 2 CH3 HH 130-135 • 10 2.13 CH3 CH3 HH 154-156 2.14 CH3 CH3 HH oil 2.15 CH (CH3) 2 CH (CH3): HH 200-205 2.16 CH (CH3): CH (CH3): HH 65-70 2.17 CH (CH3) 2 CH (CH3); H H oil 15 2.18 CH3 CH3 H H 78-79 The 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I and their salts useful in agriculture are suitable, both
• in the form of mixtures of isomers, such as in the form of pure isomers, as herbicides. The herbicidal compositions that
comprise compounds of formula I control vegetation in areas where there are no crop plants very efficiently, especially at high application rates. They act against weeds and harmful grass in crops, for example, wheat, rice, corn, soybeans and cotton without
cause significant damage to the harvest plants. This effect is observed mainly in low application regimes. According to the method of application employed, the compounds I, or the compositions comprising them, can be additionally used in a further number of harvest plants to eliminate undesirable plants. Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus ^^ officinalis, Beta vulgaris spec. altissima, Beta vulgaris
spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lemon, Citrus sinensis, Coffea arabica Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus
carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuss, Hevea Brasiliensis,
• Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon
lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus pérsica, Pyrus communis, Ribes sylvestre,
Ricinus communis, Saccharum officinarum, Sécale cereale, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, V Vicia faba, Vitis vinifera and Zea mays. In addition, the compounds I can also be used in crops that tolerate the action of herbicides due to selection, including genetic engineering methods. The compounds I, or the herbicidal compositions comprising them, can be used, for example, in the form of
^^ aqueous solutions ready to spray, dust,
suspensions, also aqueous, oily or other highly concentrated suspensions or dispersions, emulsions, dispersions in oil, pastes, powders, materials for broadcast application, or granules, by means of spraying, atomization, spraying, broadcast application or irrigation.
The forms of use depend on the intended purposes; in any way, they must guarantee a very fine distribution of the active compounds according to the invention. The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the
formula I or a useful salt in agriculture of I and auxiliaries that are commonly used for the formulation of crop protection agents. Essentially, suitable inert auxiliaries include: fractions of mineral oil from medium boiling point to
, such as, for example, kerosene and diesel oil, in addition to coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons,
Example, paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their
derivatives, alcohols such as for example methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, for example, amines such as N-methylpyrrolidone and water.
^^ Aqueous forms of use can be prepared from
emulsion concentrates, suspensions, pastes, wettable powders or granules that can be dispersed in water, by adding water. To prepare the emulsions, pastes or dispersions in oil, the substances, either as such or dissolved in an oil or solvent, can
to be homogenized in water through a wetting agent, tackifier, dispersant or emulsifying agent. Alternatively, it is possible to prepare concentrates comprising an active compound, wetting agent, tackifier, dispersant or
emulsifier and, if desired, solvent or oil, which are suitable for dilution with water., Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example , acid
ligno-, phenol-, naphthalene- and dibutylnaphlenesulfonic, and fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and alcohol sulphates
• Fatty acids and salts of sulfated hexa-, hepta- and octadecanoles, and also fatty acid glycol ether, condensates of sulfated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylenectylphenol, isooctyl-, octyl- or nonylphenol ethoxylated, alkylphenyl or tributylphenyl, polyglycol ether, alkylaryl polyether alcohols,
• 10 isotridecyl alcohol, fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or
methylcellulose. Powders, materials for broadcasting can be prepared by mixing or milling the active compounds together with a solid carrier. Granules, for example, coated granules, granules
impregnated and homogeneous granules can be prepared by binding the active compounds with solid carriers. Solid vehicles are mineral lands, such as silicas, silicas, silicates, talc, kaolin, limestone, chalk, chalk, fine clay, loess,
clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, phosphate
• Ammonium and ammonium nitrate, ureas and products of vegetable origin, such as cereal powder, tree bark powder, wood dust and nut skin powder, cellulose powder, or other solid vehicles. The concentrations of compounds I in the ready-to-use preparations can vary within wide ranges. In general, the formulations comprise approximately
• 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are used in a purity of 90% to 100%, preferably 95 to 100% (in accordance with the NMR spectrum). The following formulation examples illustrate the preparation of such formulations: I. 20 parts by weight of compound No. 2.2 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 a 10 moles of ethylene oxide to 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. The solution is poured into 100,000 parts by weight of water and finally said solution is distributed to provide an aqueous dispersion comprising 0.02% by weight of the active compound. (fe II) 20 parts by weight of compound No. 2.8 are dissolved in a mixture consisting of 40 parts by weight of 5-cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide a 1 mole of isooctylphenol and 10 parts by weight the adduct of 40 moles of ethylene oxide to 1 mole of oil of
^. castor Emptying the solution in 100,000 parts by weight
of water and finely distributing therein is obtained an aqueous dispersion comprising 0.02% by weight of the active compound. III. 20 parts by weight of active compound No. 2.8 are dissolved in a mixture composed of 25 parts by weight
of cyclohexanone, 65 parts by weight of a fraction of mineral oil with a boiling point between 210 and 280 ° C and 10 parts by weight of the adduct of 40
• moles of ethylene oxide to 1 mole of castor oil. Emptying the solution in 100,000 parts by weight of
Water and finely distributing it therein is obtained an aqueous dispersion comprising 0.02% by weight of the active compound. IV. 20 parts by weight of active compound No. 2.2 are completely mixed with 3 parts by weight of
Sodium diisobutyl naphthalenesulfonate, 17 parts by weight of the sodium salt of lignosulfonic acid from a residual sulphite liquor and 60 parts by weight of gel P of silica powder, and the mixture is ground in a hammer mill. The fine distribution of the mixture in 5-20,000 parts by weight of water provides a spray mixture comprising 0.12% by weight of the active compound. V. 3 parts by weight of active compound No. 2.8 are mixed ^^ with 97 parts by weight of finely divided kaolin. This
provides a powder comprising 3% by weight of the active compound. SAW. 20 parts by weight of the active compound No. 2.2 are intimately mixed with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of
fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a condensate of
^ fc phenol / urea / formaldehyde and 68 parts by weight of a paraffin mineral oil. This provides a stable oily dispersion. 20 VII. 1 part by weight of active compound No. 2.8 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This provides an emulsion concentrate
stable.
VIII.1 part by weight of active compound No. 2.2 is dissolved in a mixture composed of 80 parts by weight of
• cyclohexanone and 20 parts by weight of Wettol® EM 31 (= non-ionic emulsifier based on ethoxylated castor oil). This provides a stable emulsion concentrate. The compound of the formula I or the herbicidal compositions can be applied before the emergence of the plants or
^^ after the emergence of plants. If the compounds
As the active ingredients are less tolerated by certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed, with the help of the spraying equipment, in such a way that they come into contact as little as possible, if at all. contact, with the leaves
plants of sensitive crops, while the active compounds reach the leaves of the undesirable plants that grow below, or the bare surface of the soil (lateral application, backward application). The application regimes of the compound of the formula I are
from 0.001 to 3.0, preferably from 0.01 to 1.0 kg / ha of active substance (s.a.), according to the control objective, the season, the target plants and the growth stage. To broaden the spectrum of activity and to achieve synergistic effects, the benzoylpyrazoles substituted by 3-25 heterocyclyl of the formula I can be mixed with a large number of representatives of other groups of active compounds that regulate growth or herbicides and flp applied after concomitantly. Suitable components for mixtures are, for example, 1, 2, 4-thiadiazoles,
1, 3, 4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anuides, acids
(het) aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2- (het) aroyl-1-, 3- ^ ^ cyclohexandiones, hetarylaryl ketones, benzylisoxazolidinones,
derivatives of meta-CF3-phenyl, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexeneone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, ethers
diphenyls, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles,
• imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydroftalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and their
Derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, 2-pyrimidylic ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils. It can also be advantageous to apply the compounds of the formula I, either alone or concomitantly in combination with other herbicides, in the form of a mixture with others
P crop protection agents, for example, together with agents to control pests or fungi or bacteria
phytopathogenic It is also interesting the ability to mix with solutions of mineral salts that are used for the treatment of deficiencies of nutrients and minor elements. You can also add oils not
^^ phytotoxic and oil concentrate. EXAMPLES OF USE The herbicidal activity of benzoylpyrazoles substituted by 3-heterocyclyl of the formula I was demonstrated through the following greenhouse experiments: The culture vessels used were plastic pots
containing loamy sand with approximately 3.0% humus as substrate. The seeds of the test plants were seeded separately for each species. For the pre-emergence treatment of the seedlings, the active compounds, which had been suspended or
emulsified in water were applied directly after sowing through fine distribution nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic bells until the plants
have taken root. This coating causes uniform germination of the test plants, unless they have been adversely affected by the compounds
• assets . For the post-emergence treatment of the plants, 5 the test plants were first cultivated to a height of 3 to 15 cm, according to the habit of the plant, and only then treated with the active compounds that had been suspended or emulsified in water. . The test plants were, for this purpose, either sown
• 10 directly and grown in the same containers, or were first cultivated separately as seedlings and transplanted in the test containers a few days before treatment. The application regime for post-emergence treatment can be 0.25, 0.125 or
0.0625 kg of s.a. (active substance) / ha. Depending on the species, the plants were kept at a temperature of 10-25 ° C or 20-35 ° C. The trial period
• extended for 2 to 4 weeks. During this period the plants were taken care of and their response to the
individual treatments. The evaluation was carried out using a scale of 0 to 100. 100 means the absence of emergence of the plants, or the complete destruction of at least the aerial parts and 0 means absence of damage or normal evolution
of growth.
The plants used in the greenhouse experiments were of the following species:
• Scientific name Common Name Chenopodium album ash Echinochloa cruz galli farm pasture Ipomoea ssp. wonder Polygonum persicaria persicario Setaria faberi giant fox tail Setaria eiridis green foxtail • 10 White mustard alba synapsis Solanum nigrum solano At application rates of 0.25 to 0.125 kg / ha, compound 2.2 (Table 2) showed a very good after-action at the emergence of seedlings against both harmful plants
such as farm pasture and green fox tail and against ashes, persicario and solano. In addition, compound 2.8 (Table 2) presented, under the above conditions, very good action
• against undesirable plants such as farm pasture, giant foxtail, marigold, white mustard and soda. twenty
Claims (6)
- CLAIMS 1. A 3- (heterocyclyl) bepzoylpyrazole derivative of the formula I • wherein X is O, NH c or N (C? -C6 alkyl); R 1 is nitro, halogen, Ci-C alkoxy, C 1 -C 4 haloalkoxy, C 1 -C alkylthio, C 1 -C 4 haloalkyl, C 4 -C 4 alkylsulfonyl, or C 1 -C 4 haloalkylsulfonyl; R 2, R 3, R 4, R 5 are hydrogen, C -C alkyl. or haloalkyl halogen, nitro, haloalkyl C: -C4, alkoxy C.-C4, haloalkoxy C1-C4, alkylthio C1-C4, haloalkiltio C.-C4, alkylsulfenyl C1-C4 or haloalkylsulfonyl C? -C4; R7 is hydroxy, C6-C6 alkoxy, C3-C6 alkenyloxy, alkylsulfonyloxy C.-Cd, alkylcarbonyloxy C.-C6, (alkylthio: C? -C4-carbonyloxy, phenylsulfonyloxy or phenylcarbonoxy), wherein the phenyl radical of the two above-mentioned substituents may be partially or totally halogenated and / or may carry one to three of the following groups: fl nitro, cyano, C1-C4 alkyl, haloalkyl C1-C4, alkoxy C_C or haloalkoxy C1- C4; R8, R9 are C? -C4 alkyl, R10 is hydrogen or C? -C4 alkyl, where the number of carbon atoms of the radicals Rr, R9 and R10 together is at most 7; ^^ R11 is hydrogen or C2-C4 alkyl and its salts useful in agriculture 2. A 3- (heterocyclyl) benzoylpyrazole derivative of the formula I according to claim 1, wherein X is O; R1 is nitro, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylthio, fe Rd is C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl 3. A 3- (heterocyclic) benzoyl derivative pyrazole of the formula I according to claim 1, in 20 where X is O; R1 is nitro, halogen, C.sub.4-alkoxy or alkylthio R.sub.6 is halogen, nitro, haloalkyl C? ~ C4, alkoxy C1-C4 or haloalkoxy Ci-C .. Four . A 3- (heterocyclyl) benzoylpyrazole derivative of the formula I in accordance with that claimed in • claim 1, wherein X is N (C.sub.C alkyl) • 5. A process for the preparation of 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I, wherein R = hydroxyl according to that claimed in Claim 1, comprising the acylation of a ^ pyrazole of the formula II with an activated Izo benzoic acid or an Illß activated benzoic acid 15, wherein the variables X, R1 to R6 and R8 to R11 are in accordance with that defined in claim 1 and L1 is a nucleophilically displaceable leaving group and rearregating the acylation product, in the presence or absence of a catalyst, to provide the compounds of the formula I wherein R7 = hydroxyl. 6. A process for the preparation of 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I, wherein R7 OH according to claim 1, wherein • comprises the reaction of a pyrazole of formula II • wherein the variables R8 to Ru are in accordance with that defined in claim 1, or an alkali metal salt thereof, with a 3- (heterocyclyl) benzene derivative of the formula V wherein the variables X and R1 to R are in accordance with that defined in claim 1 and L2 is a leaving group in the presence of carbon monoxide, a catalyst and a base. . A process for the preparation of 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I, wherein R7 is not hydroxy in accordance with claim 1, which comprises the reaction of a 3- (heterocyclyl) benzoylpyrazole derivative I where R7 = hydroxyl I where R7 = OH P with a compound of the formula VI 10 L3-Ra VI wherein L3 is a nucleophilically replaceable leaving group; R7a is C?-C6 alkyl, C3-C6 alkenyl, C alqu-C6 alkylsulfonyl, C?-C6 alkylcarbonyl, (alkylthio) carbonyloxy C.-C4, Phenylsulfonyl or phenylcarbonyl, wherein a phenyl radical of the two substituents mentioned in - last instance may be partially or totally halogenated and / or may carry one to three of the following groups: nitro, cyano, C1-C4 alkyl, haloalkyl C.-C4, C 1 -C 4 alkoxy or C 1 -C haloalkoxy. 8. A composition, comprising a herbicidally effective amount of at least one derivative of 3- (heterocyclyl) benzoylpyrazole of the formula I or a salt 25 useful in agriculture of I, in accordance with the claim in any of claims 1 to 4, and auxiliaries usually employed for the formulation of agents for the protection of crops. 9. A process for preparing compositions according to claim 8, comprising mixing a herbicidally effective amount of at least one 3- (heterocyclyl) benzoylpyrazole derivative of the formula I or a salt useful in the agriculture of I, in accordance with the claim in any of claims 1 to 4, and auxiliaries that are customarily employed to formulate crop protection agents. 10. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one 3- (heterocyclyl) benzoylpyrazole derivative of the formula I or a useful agricultural salt of I, in accordance with The claim in any of claims 1 to 4 acts on the plants, their habitat and / or seeds. 11. The use of the 3- (heterocyclyl) benzoylpyrazole derivatives of the formula I and / or their salts useful in agriculture, as claimed in any of claims 1 to 4, as herbicides.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09207834 | 1998-12-07 |
Publications (1)
Publication Number | Publication Date |
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MXPA01005666A true MXPA01005666A (en) | 2002-05-09 |
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