MXPA94007991A - Phenylsulfonylureas, synthesis and use thereof as herbicides and vegetal growth regulators - Google Patents
Phenylsulfonylureas, synthesis and use thereof as herbicides and vegetal growth regulatorsInfo
- Publication number
- MXPA94007991A MXPA94007991A MXPA/A/1994/007991A MX9407991A MXPA94007991A MX PA94007991 A MXPA94007991 A MX PA94007991A MX 9407991 A MX9407991 A MX 9407991A MX PA94007991 A MXPA94007991 A MX PA94007991A
- Authority
- MX
- Mexico
- Prior art keywords
- och
- ochg
- alkyl
- och3
- chg
- Prior art date
Links
- 230000002363 herbicidal Effects 0.000 title claims abstract description 18
- 239000004009 herbicide Substances 0.000 title claims abstract description 10
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 239000003630 growth substance Substances 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 230000002194 synthesizing Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 42
- 239000011780 sodium chloride Substances 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims description 101
- 125000003545 alkoxy group Chemical group 0.000 claims description 59
- 241000196324 Embryophyta Species 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 39
- UJTMLNARSPORHR-UHFFFAOYSA-N OC2H5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000002689 soil Substances 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatoms Chemical group 0.000 claims description 4
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 229960001663 sulfanilamide Drugs 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 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
- QTRRBBBZOZXIMT-UHFFFAOYSA-N carbamoyl benzenesulfonate Chemical compound NC(=O)OS(=O)(=O)C1=CC=CC=C1 QTRRBBBZOZXIMT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000005648 plant growth regulator Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 239000004476 plant protection product Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- -1 defined in claim 1 Chemical class 0.000 abstract description 29
- 229940093912 Gynecological Sulfonamides Drugs 0.000 abstract description 7
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 abstract description 7
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 abstract description 7
- 150000003456 sulfonamides Chemical class 0.000 abstract description 7
- 229940026752 topical Sulfonamides Drugs 0.000 abstract description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract description 4
- 101700079793 NR13 Proteins 0.000 abstract description 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 102220012898 rs397516346 Human genes 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 41
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000011734 sodium Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 12
- 239000008187 granular material Substances 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000000227 grinding Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- JNYAEWCLZODPBN-CTQIIAAMSA-N Sorbitan Chemical class OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- DGDAVTPQCQXLGU-UHFFFAOYSA-N 5437-38-7 Chemical class CC1=CC=CC(C(O)=O)=C1[N+]([O-])=O DGDAVTPQCQXLGU-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 150000003939 benzylamines Chemical class 0.000 description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- AZMDSEPVJOPNKY-UHFFFAOYSA-N methyl 4-(acetamidomethyl)-2-(tert-butylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=C(CNC(C)=O)C=C1S(=O)(=O)NC(C)(C)C AZMDSEPVJOPNKY-UHFFFAOYSA-N 0.000 description 3
- GTOCTSLJVLBGCM-UHFFFAOYSA-N methyl 4-(azidomethyl)-2-(tert-butylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=C(CN=[N+]=[N-])C=C1S(=O)(=O)NC(C)(C)C GTOCTSLJVLBGCM-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 230000001105 regulatory Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000004546 suspension concentrate Substances 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 239000004562 water dispersible granule Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N Azobisisobutyronitrile Chemical compound N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000006463 Brassica alba Nutrition 0.000 description 2
- 244000140786 Brassica hirta Species 0.000 description 2
- 244000144786 Chrysanthemum segetum Species 0.000 description 2
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 240000006962 Gossypium hirsutum Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- 240000006022 Lolium multiflorum Species 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-Bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- KDEDDPRZIDYFOB-UHFFFAOYSA-N N-methyl-N-phenylnitramide Chemical class [O-][N+](=O)N(C)C1=CC=CC=C1 KDEDDPRZIDYFOB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000005616 Rimsulfuron Substances 0.000 description 2
- 235000007238 Secale cereale Nutrition 0.000 description 2
- 240000002057 Secale cereale Species 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000005824 corn Nutrition 0.000 description 2
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000000749 insecticidal Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- UGZZXAHJFHYIMU-UHFFFAOYSA-N methyl 4-(acetamidomethyl)-2-sulfamoylbenzoate Chemical compound COC(=O)C1=CC=C(CNC(C)=O)C=C1S(N)(=O)=O UGZZXAHJFHYIMU-UHFFFAOYSA-N 0.000 description 2
- ZHFKPVIRVHQEKF-UHFFFAOYSA-N methyl 4-(aminomethyl)-2-(tert-butylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1S(=O)(=O)NC(C)(C)C ZHFKPVIRVHQEKF-UHFFFAOYSA-N 0.000 description 2
- XKAAYWVNUUCVGC-UHFFFAOYSA-N methyl 4-(bromomethyl)-2-(tert-butylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=C(CBr)C=C1S(=O)(=O)NC(C)(C)C XKAAYWVNUUCVGC-UHFFFAOYSA-N 0.000 description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000005338 nitrobenzoic acids Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
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- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- CCPPLLJZDQAOHD-FLIBITNWSA-M vernolate Chemical compound CCCCCC1OC1C\C=C/CCCCCCCC([O-])=O CCPPLLJZDQAOHD-FLIBITNWSA-M 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The present invention relates to compounds of fórmula (I) or their salts, such as defined in claim 1, wherein:R1 means CO-Q-R8, being R8=H or R, R2, R3 mean H or C1-C4 alkyl, R4 means H, R, RO, OH, RCO, RSO2, PhSO2, (Ph=phenyl), R5 means RSO2, PhSO2, PhCO, RNHSO2, R2NSO2, RCO, CHO, COCOR', CW-T-R9, CW-NR10R11, CW-N(R12)2 or R4 and R5, together, form chain (CH2)mB or -B1-(CH2)m1B-, being B=SO2, CO;M=3, 4;m1=2, 3;T,W mean O, S;Q means O, S, NR13, being R13=H, R;R6 means H, R, RO, RCO, ROCO, Hal, NO2, CN;R7 means H, CH3;R9 is R;R10 and R11 are H, R;N(R122 means heterocycle;A means a pyrimidyl or triazinyl residue, or an analog thereof, provided that R means an aliphatic hydrocarbon residue (subst.), which are ideal as selective herbicides. Obtainment is performed similarly to processes already known (see claim 4) through sulfonamides of fórmula (II), which are somewhat novel.
Description
"PHENILSULFONILUREAS, SYNTHESIS AND USE OF THEM AS HERBICIDES AND REGULATORS OF VEGETABLE GROWTH"
Inventor (s): LAUS LORENZ, LOTHAR WILLMS, LAUS BAUER and HERMANN BIERINGER, Germans; the first and second Chemists with diplomas, the third qualified Biologist and the fifth Diplomado Engineer in Agriculture, residing in: Vor der Brube 9, D-64331 Weiterstadt; Kanigsteiner Strasse 59, D-65719 Hofhei; Daorner Strasse 53d, D-? SM-Bó Hanau and Eichenweg 26, D-65ñl7 Eppstein, respectively Federal Republic of Germany.
Causation: HOECHST-SCHERING AGREVO GMBH, a German company, domiciled at: D-13509 Berlin, Federal Republic of Germany.
SUMMARY
The compounds of the formula I or their salts, as defined in claim 1 »
R2- the
wherein R1 signifies CO-Q-R8, where R8 = H or R, R2, R3 signify H or C, -C4 alkyl, R4 signifies H, R, RO, OH, RCO, RS02, PhS02 (Ph = phenyl) ,
R5 means RS02, PhS02, PhCO, RNHS02, R2NS02, RCO, CHO,
COCOR ', CW-T-R9, CW-NRU, RU, CW-N (R12) 2 or R4 and R5, together, form the chain (CH2) mB or the -B1- (CH2) m, B-, being B = S02, CO; M = 3, 4; m1 = 2, 3; T, W mean O, S; Q means 0, S, NR13, where R13 =
H, R;
R6 means H, R, RO, RCO, ROCO, Hai, N02, CN; R7 is H, CH3; R9 is R; R10 and Rp are H, R; N (R, 2) 2 means heterocycle; A means a pyrimidyl or triazinyl radical or an analogue thereof, given that R represents an aliphatic hydrocarbon radical (sust-,), are suitable as selective herbicides. The preparation is carried out in a manner similar to known processes (see claim 4) through sulfonamides of the formula (II), which are in part new.
DESCRIPTIVE MEMORY
It is known that some phenylsulfonylureas possess herbicidal and plant growth regulating properties; see US-A-4,786, 314, US-A-4, 927, 453 and WO 89/10921. However, in some cases these have drawbacks in their application, such as, for example, high persistence or insufficient selectivity in important crops of plants of agricultural interest. Now phenylsulfonylureas have been found with special moieties on the phenyl ring which can be used with advantages as herbicides and plant growth regulators. The subject of the present invention are the compounds of the formula (I) or their salts,
NR * R wherein R means CO-Q-R8, R2, R3, independently of each other, mean H or C ^ alkyl, R4 signifies H, C, -C8 alkyl which may be unsubstituted or substituted by one or various residues of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfinyl, (C 1 -C 4) alkylsulfonyl, (alkoxy) -C, -C4) - carbonyl and CN, or C3-C6 alkenyl which may be unsubstituted or substituted by one or more halogen atoms, or C3-C6 alkynyl which may be unsubstituted or substituted by one or more atoms of halogen, or hydroxy, C ^ Q alkoxy, (C-alkyl, -C4) -carbonyl or (C-C4 alkyl) -sulfonyl, given that each of the three last-mentioned residues is unsubstituted or substituted on its alkyl part by one or more halogen atoms or by C 1 -C 4 alkoxy or (C 1 -C 4) alkyl, or phenylsulfonyl, taking into account that the phenyl radical is unsubstituted or substituted , preferably by one or more remains of the series consisting of halogen, CN, N02, C, -C4 alkyl, C, -C4 haloalkyl and C, -C4 alkoxy, and R5 means (C-C4 alkyl) -sulfonyl or (C3-C3-alkenyl) - sulfonyl, in view of the fact that each of the last-mentioned radicals is unsubstituted or substituted by one or more halogen atoms or by C, -C4 or (C 1 -C 4 alkyl) -thio alkoxy; or phenylsulfonyl or phenylcarbonyl, taking into account that the phenyl residue of each of the two last-mentioned radicals is unsubstituted or substituted, preferably by one or more residues of the series consisting of halogen, CN, N02, alkyl Cj-C ,,, haloalkyl C ^, and alkoxy Cj-,; either mono- or di- (C 1 -C 4 alkyl) -aminosulfonyl or (C 1 -C 6 alkylcarbonyl), given that each of the three last-mentioned residues is unsubstituted or substituted by one or several residues of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfinyl, (C 1 -C 4 alkyl) -sulfonyl, ( alkyl-C, -C4) -carbonyl, (C-C4-alkoxy) -carbonyl and CN; or formyl, a group of the formula -CO-CO-R ', in which R' signifies H, OH, C, -C4 alkoxy or C, -C4 alkyl, or (C3-C6 cycloalkyl) -carbonyl (C2-C6-alkenyl) -carbonyl or (C2-C6-alkynyl) -carbonyl, taking into account that each of the three last-mentioned radicals is unsubstituted or substituted by one or more halogen atoms; or a group of the formula WWW II II - C - T - R9, - C - NR? Rp or - C - N (R1) 2 or R4 and R5, together, form a chain of formula (-CH2) mB- or -B1- (CH2) ml-B-, given that the chain can be unsubstituted or substituted by one or more, preferably up to four C! -C3 alkyl moieties and m is the number 3 or 4, or okay m1 is number 2 or 3, as well as
W means an oxygen or sulfur atom (i.e., O or S), B, B1 independently of each other, meaning S02 or CO, Q means O, S or -NR13-, T means O or S, R6 means H , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, (C 1 -C 8 alkyl) carbonyl or (C 1 -C 6 alkoxycarbonyl, in view of the fact that each of the 4 last mentioned moieties may be replacing or substituted in its alkyl part by one or more halogen atoms, or halogen, N02 or CN, R7 means H or CH3, R8 means H, C, -C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl, Note that each of the three last-mentioned moieties is unsubstituted or substituted by one or more moieties of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (alkyl), C, -C 4) - carbonyl or (C 1 -C 4 -alkoxycarbonyl, R 9 means C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl, given that each of the three residues mentioned last place is unsubstituted or replaced by one or vari The remains of the series consisting of halogen, C 1 -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -carbonyl and (C 1 -C 4 alkoxy) -carbonyl, R 10, R 11, independently of each other, they mean H, C 1 -C 4 alkyl, C 3 -C 4 alkenyl or C 3 -C 4 alkynyl, given that each of the three last-mentioned residues is unsubstituted or substituted by one or more residues of the series consisting of halogen, Cj-C4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4) alkylcarbonyl, and (alkoxy- ^ -,) -carbonyl, the R 12 moieties, together with the N, form a 5- or 6-membered heterocyclic ring, which may have other heteroatoms of the series consisting of N, O and S in their possible oxidation degrees, and is unsubstituted or substituted by C, -C4 alkyl or by the group oxo or is condensed with a benzene, R13 means H, C, - ^, C3-C4 alkenyl or C3-C4 alkynyl, given that each of the three last mentioned moieties is unsubstituted or substituted by one or several rest of the series consisting of halogen, alkoxy 0, -04 and (C-alkyl, -4-thio) is a residue of the formula
one of the radicals X and Y is hydrogen, halogen, C-C3-alkyl or C-C3-alkoxy, in view of the fact that the two last-mentioned radicals are unsubstituted or substituted one or more times by halogen or once by alkoxy C, -C3, and the second of residues X and Y is hydrogen, C, -C3 alkyl, C, -C3 alkoxy or (C, -C3 alkyl) -thio bearing in mind that the three last mentioned moieties they are unsubstituted or substituted one or more times by halogen or one or two times by C 1 -C 0 alkoxy or (C 1 -C 3 alkyl) -thio; or a residue of the formula NR14R15, C3-C6 cycloalkyl, C2-C4 alkenyl, C2-C4 alkynyl, C3-C4 alkenyloxy or C3-C4 alkynyloxy, Z means CH or N, R14 and R15, independently of each other, mean H , I rent
Cj-Cj or C3-C4 alkenyl, X1 means CH3, OCH3, or C2H5 or OCHF2, Y1 means -O-, -CH2-, X2 means CH3, C2H5 or CH2CF3, Y2 means OCH3, OC2H5, SCH3, SCH2CH3, CH3 or C2H5 X3 means CH3 or OCH3, Y3 signifies H or CH3, X4 signifies CH3, OCH3, OC2H5, CH2OCH3 or Cl, Y4 signifies CH3, OCH3, OC2H5 or Cl and Y5 signifies CH3, C2H5, OCH, or Cl. In the formula ( I) and hereinafter, the alkyl, alkoxy, haloalkyl, alkylamino and alkylthio moieties as well as the corresponding unsaturated and / or substituted moieties can have a carbon skeleton in each case linear or branched. The alkyl radicals, even in their compound meanings such as alkoxy, haloalkyl, etc. , they mean methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl; the alkenyl and alkynyl moieties have the meaning of the possible unsaturated moieties corresponding to the alkyl moieties, such as 2-propenyl, 2- or 3-butenyl, 2-propinyl, 2- or 3-butinyl. Halogen means fluorine, chlorine, bromine or iodine; "haloalkyl" means alkyl that is substituted by one or more atoms of the halogen series; haloalkyl is for example CF3, CHF2, CH2CF3. Substituted phenyl preferably means phenyl which is substituted by one or more, preferably 1, 2 or 3 residues of the series formed by halogen, such as F, Cl, Br, I, preferably F, Cl and Br, in addition alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxy, amino, nitro, cyano, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and ialkylamino, alkylsulfinyl and alkylsulfonyl, and among the residues with C atoms, those having 1 to 4 C atoms, especially 1 or 2, are preferred. generally preferred are substituents of the series consisting of halogen, eg fluorine and chlorine, C, -C 4 alkyl, preferably methyl or ethyl, C] -C 4 haloalkyl, preferably trifluoromethyl, C, -C 4 alkoxy , preferably methoxy or ethoxy, haloalkoxy C, -C4, nitro and cyano. A 5- or 6-membered heterocyclic moiety, which is optionally condensed with a benzene and has an N atom (eg in the case of N (R, 2) 2), can be a saturated, unsaturated or heteroaromatic moiety, eg, a residue linked by the N atom of the series consisting of pyrrolidyl, piperidyl, pyrazolyl, morpholinyl, indolyl, quinolinyl, pyrimidinyl, triazolyl, oxazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thiazolyl, oxazolyl, pyrrolyl. , pyrazolyl, imidazolyl and benzoxazolyl. All the stereoisomers encompassed by the formula (I) and their mixtures are also subject of the present invention. Such compounds of the formula (I) contain one or more asymmetric C atoms or with double bonds, which are not indicated separately in the general formula (I). The possible stereoisomers defined by their specific spatial form, such as the enantiomers, diastereomers, isomers Z and E, are all contemplated by the formula (I) and can be obtained by the usual methods from mixtures of stereoisomers or also by stereoselective reactions in combination with the use of raw raw materials from the stereochemical point of view. The compounds of the formula (I) can form salts, in which the hydrogen of the -SOz-NH group is replaced by an appropriate cation for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, but also ammonium salts or salts of organic amines. Of special interest are the compounds of the formula (I) of the present invention or salts thereof, wherein R 4 is H, C, -C 4 alkyl, which may be unsubstituted or substituted by one or more residues from the series consisting of halogen , C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfonyl, (C 1 -C 4 alkoxycarbonyl, and CN, or C 3 -C 4 alkenyl, C 3 alkynyl -C4, hydroxy, C, -C4 alkoxy, (C-alkyl, -C4) -carbonyl or (Cj-C4-alkyl) -sulfonyl, in view of the fact that each of the five last-mentioned residues is unsubstituted or substituted in its alkyl part by one or more halogen atoms; or phenylsulfonyl, provided that the phenyl moiety is unsubstituted or substituted by one or more moieties of the series consisting of halogen, C, -C 4 alkyl and C 1 -C 4 alkoxy and R 5 means (C 1 -C 4 alkyl) -sulfonyl, (C-C4-haloalkyl) -sulfonyl, phenylsulfonyl or phenylcarbonyl, taking into account that the phenyl residue of each of the two last-mentioned residues is unsubstituted or substituted by one or more residues of the series formed by halogen, C, -C4 alkyl and C.C4 alkoxy; either mono- or di- (alkyl-Cj-j) -aminosulfonyl or (C 1 -C 6 alkyl) -carbonyl, which is unsubstituted or substituted by one or more halogen atoms or alkoxy 0, -04 and (alkyl) -C, - C4) -thio; or formyl, OHC-CO-, 2-oxo- (C3-C5 alkanoyl), (C-C4 alkoxy) -oxalyl, (C3-C6 cycloalkyl) -carbonyl, (C2-C4 alkenyl) - carbonyl or (C2-C4 alkynyl) -carbonyl or a group of the formula WWW
II II - C - T - R9, - C - NR10Rn or - C - N (R, 2) 2 W means O or S, R6 means H, C - C4 alkyl, C - C4 haloalkyl, C - alkoxy, - C4, haloalkoxy C, -C4 or halogen, R8 independently of one another, means Cj-C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl, which is unsubstituted or substituted by one or more halogen atoms, or by alkenyl C3-C4 or C3-C4 alkynyl, R9 signifies H, alkyl 0, -0, which is unsubstituted or substituted by one or more halogen atoms or by alkoxy 0, -0 ,,, (C-alkyl, -C4 ) -thio (alkoxy-C, -C4) -carbonyl or (alkyl-C, -C4) -carbonyl, R10, Rp, independently of each other, mean H, C, -C4 alkyl, which is unsubstituted or substituted by one or more halogen atoms; or C3-C4 alkenyl or C3-C4 alkynyl, given that at least one of the radicals R10 and Rp is other than hydrogen, the radicals R12, together with the N atom, form a heterocyclic ring of 5 or 6 links, which may have another heteroatom of the series consisting of N, O and S in their possible oxidation degrees, and is unsubstituted or substituted by C, -C4, and R13 alkyl independently of each other, means H, C alkyl, -C4, which is unsubstituted or substituted by one or more halogen atoms; or C3-C4 alkenyl or C3-C alkynyl. Preferred compounds of the formula (I) or salts thereof are those in which W means an oxygen atom and A is a radical of the formula
where X, Y and Z have the meanings defined before. Especially preferred compounds of the formula (I) or their salts are those in which R 4 denotes H, C, -C 4 alkyl or C, -C 4 alkoxy, R 5 means (C 1 -C 4 alkyl) -sulfonyl, CHO, ( alkyl-C, -C 4) -carbonyl which is unsubstituted or substituted by one or more halogen atoms; or (C-C4 alkoxy) -oxalyl, (C3-C6 cycloalkyl) -carbonyl or a group of the formula W W W
II II - C - T - R9, - C - NR10Rn or - C - N (R12) 2 given that W, T, from R9 to R12 have the meanings defined above for the formula (I), R6 means H , C, -C3 alkyl, C, -C3 alkoxy or halogen, A is a residue of the formula
Z means CH or N, preferably CH, and one of the radicals X and Y means halogen, C, -C2 alkyl, C, -C2 alkoxy, OCF2H or OCH2CF3 and the second of the X and Y residues means C, - alkyl. C2, C, -C2 alkoxy or haloalkoxy
^ l-C2. For reasons of their greater ease of obtaining or of their best biological effects, the compounds of the formula (II) of the invention or their salts are of special interest, in which the group -CR2R3-NR4R5 occupies an ortho or para position with respect to to the group R1 or the ortho position with respect to the sulfo group; the para position of the group -CR2R3-NR4R5 with respect to the group R1 is preferred in this context. The present invention also relates to processes for obtaining the compounds of the general formula (I) or their salts, characterized in that a) a compound of the formula (II) is reacted
V 4 5
with a heterocyclic carbamate of the formula (III) R * -O-CO-NR7-A (III) in which R * means optionally substituted phenyl or C, -C4 alkyl, or b) a phenylsulfonyl carbamate is reacted of the formula (IV)
NR R with an aminoheterocycle of the formula (V) H-NR7-A (V) or C) is reacted with a sulfonyl isocyanate of the formula (VI)
\ NR 4R5
with an aminoheterocycle of the formula H-NR7-A (V), or d) in a reaction in a single reactor, an aminoheterocycle of the formula H-NR7-A (V) is first reacted with phosgene in the presence of a base and then the intermediate product formed is reacted with a phenylsulfonamide of the formula (II), or e) a sulfonyl chloride of the formula (VII) is reacted
NR4R5 with a cyanate of formula M-OCN, where M means
NH4, Na or K, and with an aminoheterocycle of the formula H- NR7-A (V) in the presence of a base, f) a sulfonamide of the formula (II) mentioned is reacted with a (thio) -isocyanate of the formula (V) W = C = N - A (V) in the presence of a base, in view of the fact that in formulas (II) - (VII) and (V ') the radicals or groups R1-R7, A or W have the same meaning defined for formula (I) and variants a) - e ) the compounds of the formula (I) in which W is O are first obtained. The reaction of the compounds of the formula (II) and (III) is preferably carried out by basic catalysis in an inert organic solvent. , such as, for example, dichloromethane, acetonitrile, dioxane or THF, at a temperature between 0 ° C and the boiling point of the solvent. As bases, for example, organic amine bases, such as 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), are used, especially when R * is phenyl (sust.) (See PE-A-44807 ), or trimethylaluminum or triethylaluminum, the latter especially when R * signifies alkyl (see PE-A-166516). Sulfonamides (II) are new compounds. They and their obtaining are also object of the present invention. Taking as an example the compound (II), in which R2 = R3 = H and Q = O, the possibilities of obtaining are illustrated in more detail, which, with minor variations, can also be used for the compounds in which R2, R3 are other than hydrogen or in which Q is other than O. Starting from optionally substituted methylanilinesulfonic acids (VIII) (see DRP 48383, page 242), which are first converted by diazotization and reaction with KCN / CnCN according to Sandmeyer in the nitriles (IX), the sulfonamide (X) is obtained as an intermediate product, after saponification of the nitrile, esterification of the carboxylic acid groups and conversion of the sulfonic acid group to the sulfonamide protein group with a tert-butyl group, by a process analogous to already known by the technical bibliography (see diagram 1).
Scheme 1
Otherwise, the sulfonamides (X) are obtained starting from optionally substituted methylnitrobenzoic acids (XI) by esterification, reduction of the nitro group, diazotization and coupling with S02 / CuCl (see H. Meerwein et al., Chem. Ber. 90, 841-1178 (1957)) and aminolysis with tert-butylamine (see scheme 2). Scheme 2
The sulfonamides (X) can also be synthesized starting from optionally substituted methylnitroanilines (XII). Diazotization and coupling with KCN / CuCN provides the corresponding nitriles, which by hydrolysis of the cyano group and esterification can be converted into nitrobenzoic acid esters (XIII).
The nitro group can then be converted, as described in scheme 2, to the tert-butylaminosulfonyl group (see scheme 3). Scheme 3
To obtain the sulfonamides (II), the compounds of the formula (X) by halogenation of the side chain are converted to (XIV), then by substitution of the halogen atom of (XIV) with amines or with azide with subsequent reduction they become in benzylamines (XV) and by functionalization of the amino group as well as removal of the tert-butyl protecting group in a manner similar to that described in the technical literature (eg with CF3COOH) they are transformed into the sulfonamides (II ') (see scheme 4). Scheme 4
NHC (CH3) 3
The method can also be used in a similar way to obtain other compounds of the formula (II), given that the compound of the formula (XV) is used in the last step.
NR4R5
The carbamates of the formula (III) can be obtained by methods described in the South African patent applications 82/5671 and 82/5045 or PE-A-70804 (US-A-4 480 101) or RD 275056. The reaction of the compounds (IV) with the aminohete-rocicls (V) are preferably carried out in aprotic, inert solvents, such as, for example, dioxane, acetonitrile or tetrahydrofuran, at a temperature between 0 ° C and the boiling point of the solvent. The required starting materials (V) are known in the technical literature or can be obtained by processes described in the technical literature. The phenylsulfonyl carbamates of the formula (IV) are obtained in a manner similar to that described in US-4 684 393 or US-4 743 290. The phenylsulfonyl isocyanates of the formula (VI) can be obtained in a similar manner to that described in US Pat. No. 4,481,029. The phosgenation of the compounds of the formula (V) according to variant d) can be carried out in the presence of bases, such as the sterically hindered organic amine bases, for example triethylamine. The subsequent reaction with the compounds of the formula (II) can be carried out according to variant d) in a manner similar to the processes already known (see EP-A-232 067). The sulfochlorides (VII) can be obtained from the corresponding sulphonic acids, for example by the normal methods such as the reaction of the potassium salt with phosphorus oxychloride or thionyl chloride in inert solvents, such as acetonitrile and / or the Sulfoian, or else en masse by heating at reflux (see Houben-Weyl-Klamann, "Methoden der organischen Chemie", 4th ed., Volume E XI / 2, pp. 1067-1073, Thieme Verlag, Stuttgart 1985).
The sulfonic acids in question can be obtained from the corresponding nitrated compounds, similar to the conversion of the compounds (XI). In specific cases there is an alternative for obtaining the sulfochlorides (VII) consisting of the sulfonation (+ chlorination) or sulfochlorination of the appropriate substituted benzoic acid esters; Sulfochlorination is carried out similarly to Houben-Weyl-Klamann "Methoden der organischen Chemie", 4§ ed. , tome E XI / 2, p. 1067 ff., Thieme Publishing, Stuttgart 1985; Houben-Weyl-Müller, "Methoden der organischen Chemie11, 4th ed., Volume E XI / 2, P. 1055 et seq., Thieme editorial, Stuttgart 1985, Houben-Weyl-Müller," Methoden der organischen Chemie ", 4§ ed. , Volume IX, p. 435 et seq., Thieme Verlag, Stuttgart 1955. The (thio) isocyanates of the formula (V) can be obtained by methods known from the technical literature (EP-A-232067, EP-A-166516). The reaction of the (thio) isocyanates (V) with the compounds (II) is carried out between -10 ° C and 100 ° C, preferably between 20 and 100 ° C, in an inert aprotic solvent, such as, for example, acetone or acetonitrile, in the presence of a suitable base, eg N (C2H5) 3 or K2C03. The salts of the compounds of the formula (I) are preferably obtained in inert polar solvents, such as, for example, water or acetone, at a temperature between 0 and 100 ° C. Suitable bases for the preparation of the salts of the present invention are, for example, alkali metal carbonates, such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, for example NaOH or KOH, or ammonia or ethanolamine. With the term "inert solvents" used in the above process variants, solvents are referred to in each case which, under the reaction conditions, are inert, but this does not mean that they are in all imaginable reaction conditions. The compounds of formula (I) of the present invention exhibit excellent herbicidal efficacy against a wide range of mono- and dicotyledonous plant species that cause significant damage to agricultural crops. Even perennial weeds, difficult to control, that sprout from rhizomes, roots or from other perennial organs, are well controlled by the active ingredients. In this case it does not matter if the application of the active substances is carried out in the pre-emergency, in the pre-emergency or in the postemergence. We will cite in particular some of the typical exponents of the harmful flora, both mono- and dicotyledonous, for illustrative purposes, which can be controlled with the compounds of the present invention, without this enumeration being intended to restrict the application to certain species.
On the side of the harmful monocotyledonous species, eg Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and the Cyperus species of the annual group are well controlled; and on the perennial group side, the species Agropyron, Cynodon, Imperata and Sorghum as well as the Cyperus species of the perennial type. Regarding dicotyledonous weeds, the spectrum of action includes species such as eg Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Aids of the annual group as well as Convolvulus, Cirsium , Ru ex and Artemisia from the perennial weeds. Weeds that appear in the specific conditions of the rice culture, such as, for example, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are also excellently controlled with the active ingredients of the present invention. If the compounds of the invention are applied on the surface of the soil before germination, the emergence of the weeds may be completely inhibited or the weeds may grow to the state of the germinal leaf but then its growth is blocked and, finally, they die in their entirety after three to four weeks have elapsed.
In case of applying the active substances on the green parts of the plants in postemergence, there is also a drastic stoppage of the growth shortly after the treatment, the weeds stay stagnant in the growth stage existing at the time of application and die in its totality after a certain period of time, in such a way that the harmful competition exerted by weeds with respect to crops of agricultural interest is eliminated very early and definitively. Although the compounds of the present invention exhibit an herbicidal activity against mono- and dicotyledonous weeds, economically important crops such as, for example, wheat, barley, rye, rice, corn, sugar beet, cotton and soybeans, are not significantly affected or are not affected at all. For these reasons, the compounds of the present invention are suitable for the selective control of weed growth in plantations of agricultural interest. On the other hand, the substances of the present invention have excellent characteristics of growth regulation of cultivated plants. They affect the plant's own metabolism, regulating it and, therefore, allow concrete influence on the materials accumulated by the plants and facilitate the collection, for example, triggering the desiccation or stagnation of growth. In addition, they are appropriate for the general control and inhibition of unwanted vegetative growth, without thereby killing the plants. An inhibition of vegetative growth is very important in many monocotyledonous and dicotyledonous crops since it reduces the storage of them or avoids them altogether. The compounds of the invention can be applied in the form of spray powders, emulsifiable concentrates, spraying solutions, dusting powders or granules, in the customary formulations. Thus, the object of the present invention is also the herbicidal and plant growth regulating products containing compounds of the formula
(I) The compounds of the formula (I) or their salts can be formulated in different ways, depending on the biological and / or physical-chemical parameters existing in each of the cases. Possible formulation possibilities are, for example: spray powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as emulsions of oil-in-water and water-in-oil, sprayable solutions, suspension concentrates (SC), oil-based or water-based dispersions, oil-miscible solutions, encapsulated suspensions (CS), dusting products (DP), disinfectants, granules for spreading and application on soil, granules (GR) in the form of microgranulate, spraying, adsorption, dispersion in water (WG), water-soluble granules ( SG), the formulations ULV (= at ultra low volume), the microcapsules and the waxes. The different types of formulation are known, in principle, and are described for example in: Winnac er-Küchler, "Chemische Technologie", volume 7, Cari Hanser publishing house, Munich, 4§ ed. , 1986; Wade van Valkenburg, "Pesticide For-mulations", Marcel Dekker, N.Y. 1973; K. Martens, "Spray Drying" Handbook, 32 ed. , 1979, G. Goodwin Ltd. London. The auxiliaries necessary for the formulations, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluent and Carriers", 2 ed. , Darland Books, Caldwell, N.J .; H.v. Olphen, "Introduction to Clay Colloid Chemistry," 2 ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide", 2nd ed. , Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schónfeldt, "Grenzflachenaktive Áthylenoxidaddukte", Wiss. Verlagsgesell. , Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", volume 7, editorial C. Hanser, Munich, 4th ed. 1986. On the basis of these formulations, combinations can also be prepared with other effective substances such as pesticides, such as insecticides, acaricides, herbicides, fungicides, safeners, fertilizers and / or growth regulators, for example in Form of a ready-to-use formulation or in the form of a mixture prepared in the same application tank or "tankmix". Spray powders are prepared homogeneously dispersible in water which, apart from the active ingredient, the diluent and the inert material, also contain ionic and / or nonionic surfactants (wetting agents, dispersants), eg polyethoxylated alkylphenols, fatty alcohols polyethoxylates, polyethoxylated fatty amines, fatty alcohol and polyglycol ether sulfates, alkanesulfonates, alkylbenzene sulphonates, sodium lignosulfonate, 2,2-dinaphtylmethane-6,6'-sodium disulfonate, sodium dibutylnaphthalene sulfonate or even sodium oleoylmethyltaurinate. To prepare the spray powders, the herbicidal active ingredients are finely milled, for example, in conventional apparatuses such as hammer mills, pneumatic mills and air jet mills and, at the same time or subsequently, they are mixed with the formulation auxiliaries. The emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example in butanol, cyclohexanone, dimethylformamide, xylene or also in high-boiling hydrocarbons or aromatics or in mixtures of organic solvents, with the addition of one or more surfactants of ionic and / or non-ionic character (emulsifiers). Examples of emulsifiers which may be used are: calcium salts of alkylarylsulfonic acids such as Ca dodecylbenzenesulfonate or nonionic emulsifiers such as polyglycol esters of fatty acid, alkylaryl polyglycol ethers, fatty alcohol ethers and polyglycol ethers, condensation products with oxides of propylene and ethylene oxide, alkylpolyethers, sorbitan esters, such as, for example, fatty acid and sorbitan esters or polyethoxylated sorbitan esters, such as, for example, polyethoxylated fatty acid and sorbitan esters. Dusting products are obtained by grinding the active ingredient with finely divided solids, eg talcum, natural clays, such as kaolin, bentonite or pyrophyllite, or diatomaceous earths. The suspension concentrates can be water based or oil based. They can be prepared, for example, by wet grinding in a bead mill and, if appropriate, surfactants can be added, such as, for example, those already mentioned above for other formulations. Emulsions, eg oil-in-water (EW) emulsions can be prepared, for example, by stirring, colloidal grinding and / or static mixers, with the use of aqueous organic solvents and, if appropriate, surfactants, such as .ej those previously mentioned for other types of formulations. The granules can be prepared either by dosing through the nozzle of the active ingredient on an inert adsorbent materialgranules, or by application of concentrates of active ingredient by means of adhesives, eg polyvinylalcohol, sodium polyacrylate or also mineral oils, on the surface of the support materials, such as sand, kaolinites or granulated inert material. The suitable active ingredients can also be granulated in the usual way in the manufacture of granular fertilizers, if desired by mixing them with fertilizers. The water-dispersible granules are generally obtained by the usual processes such as spray drying, fluidized bed granulation, plate granulation, mixing in high speed mixers and extrusion without solid inert material.
As regards the preparation of cymbal granules, fluidized bed, extrusion and atomization, see eg the process in "Spray-Drying Handbook", 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 et seq .; "Perry's Chemical Engineer's Handbook", 5th ed. , McGraw-Hill, New York 1973, pp. 8-57. For more details regarding the formulation of phytosanitary products, see eg G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York 1961, pages 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5s ed. , Blackwell Scientific Publications, Oxford, 1968, pages 101-103. The agrochemical formulations generally contain from 0.1 to 99% by weight, especially from 0.1 to 95% by weight of active ingredient of the formula (I). In the spray powders, the active ingredient concentration is, for example, between 10 and 90% by weight, the rest up to 100% by weight consists of the other usual ingredients of the formulation. In emulsifiable concentrates, the concentration of active substance is between 1 and 90, preferably between 5 and 80% by weight. Dusting formulations contain from 1 to 30, preferably from 5 to 20% by weight of active ingredient in most cases. Sprayable solutions contain from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In water-dispersible granules, the content of active ingredient depends in part on whether the active compound is liquid or solid and on the granulation aids, filling fillers, etc. that are going to be used. In water-dispersible granules, the content of active ingredient is, for example, between 1 and 95%, preferably between 10 and 80% by weight. The aforementioned active ingredient formulations, if appropriate, may contain the adherents, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and customary solvents, filler fillers, support materials and dyes, defoamers, evaporation inhibitors and products that influence in the pH and in the viscosity. As the combination compounds for the active ingredients of the present invention in mixture or "tank-mix" formulations, for example, active ingredients can be used which are described for example in Weed Research 26, 441-445 (1986), or in "The Pesticide Manual", 9th ed. , The British Crop Protection Council, 1990/91, Bracknell, England, or in the technical literature cited therein. As herbicides already known from the technical literature, which can be combined with the compounds of the formula (I), it is possible to mention, for example, the following active ingredients (Note: the compounds are named either with the "common yam" of the International Organization for Standardization (ISO) or with the chemical name, possibly with the usual code number): acetochlor; acifluorfen; Aclonifen; AKH 7088, ie [[[l- [5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrophenyl-] - 2-methoxyethylidene] -amino] -oxy] -acetic acid and its methyl ester; Alachlor aloxidime; ametryn; amidosulfuron; Amitrol; AMS, that is, ammonium sulphamate; anilophos; asulam; atrazine; azimsulfuron (DPX-A8947); aziprotrine; barban BAS 516 H, ie, 5-fluoro-2-phenyl-4H-3, l-benzoxazin-4-one; benazoline; benfluralin; benfuresate; bensulfuron-methyl; bensulide; bentazone; benzofenap; benzofluor; benzoylprop-ethyl; benztia-zuron; bialaphos; bifenox; bromacil; bromobutide; bromophen-xim; Bromoxynil; bro uron; buminafos; Busoxinone; butachlor; butamiphos; butenachlor; butidazole; butralin; butylate; cafenstrol (CH-900); carbetamide; Cafentrazon (ICI-A0051); CDAA, i.e., 2-chloro-N, N-di-2-propenylacetamide; CDEC, i.e., 2-chloroalyl diethyldithiocarbamate; clometoxifene; chloramben; clorazifop-butyl; Chlormesulon (ICI-A0051); chlorobromuron; chlorbufam; chlorfenac; chlorflurecol-methyl; chloridazon; chlorimuron ethyl; clornitrofen; Chlorotoluron;
chloroxuron; chlorprofam; Clorsulfuron; chlortal-dimethyl; chlortiamide; cinmetilin; Cinosulfuron; Cletodim; clodinafop and its ester-like derivatives (eg clodinafop-propargyl); clomazon; clomeprop; cloproxidime; clopyralid; cumiluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycle-xidime; cycluron; cyhalofop and its ester-type derivatives (eg, butyl ester, DEH-112); cyperquat; ciprazine; ciprazole; daimuron; 2,4-DB; dalapon; desmedifam; desmethrin; dialate; dicamba; diclobenil; dichlorprop; diclofop and its ester-type derivatives such as diclofop-methyl; dietyl; diphenoxuron; difenzoquat; diflufenican; di efuron; dimethachlor; dimethame-trin; dimethenamid (SAN-582H); di etazon; clomazon; dimetipin; dimethrulphuron; Dinitramine; dinoseb; dinoterb; diphenamide; dipropetrin; diquat; ditiopir; diuron; DNOC; eglinazin-ethyl; EL 177, i.e., 5-cyano-l- (1,1-dimethylethyl) -N-methyl-lH-pyrazole-4-carboxamide; endotal; EPTC; esprocarb; etalflura-lina; etametsulfuron-methyl; etidimuron; etiozine; etofume-sato; F5231, i.e., N- [2-chloro-4-fluoro-5- [4- (3-fluorpro-pyl) -4,5-dihydro-5-oxo-lH-tetrazol-1-yl] -phenyl] -etanosulfo-namide; ethoxyfen and its esters (eg, ethyl ester, HN-252); etobenzanide (HW 52); fenoprop; fenoxan; fenoxaprop and fenoxaprop-P as well as their esters, e.g., fenoxaprop-P-ethyl and fenoxaprop-ethyl; phenoxydim; fenuron; flamprop-methyl; flaza-sulfuron; fluazifop and fluazifop-P as well as their esters, e.g.
fluazifop-butyl and fluazifop-P-butyl; flucloraline; flumetsu-lam; flumeturon; flumiclorac and its esters (e.g., pentylester, S-23031); flumioxazin (S-482); flu ipropin; flupoxam (KNW-739); fluorodifene; fluoroglycophon-ethyl; flupropacil (UBIC-4243); fluridone; flurocloridone; fluroxy-pir; flurtamon; fomesafeno; fosamine; furiloxifene; glufosinate; glyphosate; halosatene; halosulfuron and its esters (eg the methyl ester, NC-319); haloxifop and its esters; haloxifop-P (= R-haloxifop) and its esters; hexazinone; imazametabenz-methyl; imazapyr; imazaquin and its salts as the ammonium salt; imazetametapir; imazethapyr; imazosulfuron; ioxinil; isocarba ida; isopropaline; isoproturon; isouron; isoxaben; isoxapirifop; carbutylate; Lastophen; lenacilo; linuron; MCPA; MCPB; mecoprop; mefenacet; mefluidid; metami-tron; metazachlor; metabenzthiazuron; metam; metazole; methoxyphene; methyldimron; metabenzuron; metobenzuron; metobromuron; metolachlor; metosulam (XRD 511); Etoxuron; metribuzin; et-sulfuron-methyl; MH; molinate; monalid; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128, i.e., 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazine-ina; MT 5950, i.e., N- [3-chloro-4- (1-methylethyl) -phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e., 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxy-pyrazole; neburon; nicosulfuron; nipiraclofen; nitraline;
nitrophen; nitrofluorfen; norflurazon; orbencarb; orizalin; Oxadiargyl (RP-020630); oxadiazon; oxyfluorfen; paraquat; pebble pendimethalin; perfluidone; fenisofam; fenmedifam; picloram; piperophos; pyributicarb; pirifenop-butyl; preti-lachlor; primisulfuron-methyl; procyanine; prodiamine; pro-fluralin; proglinazine-ethyl; prometona; prometryn; propa-clor; propanil; propaquizafop and its esters; propazine; profam; propisoclor; propizamide; prosulfaliña; prosulfocarb; prosulfuron (CGA-152005); prinaclor; pyrazolinate; pyrazona; pyrosulfuron-ethyl; pyrazoxyphene; pyridate; piritiobac (KIH-2031); piroxofop and its esters (e.g., propargyl ester); quinclorac; quinmeras; quinofop and its ester-like derivatives; quizalofop and quizalsfop-P as well as their ester-type derivatives, eg quizalofop-ethyl; quizalofop-P-tefuril and -P-ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, i.e., 2- [4-chloro-2-fluoro-5- (2-propynyloxy) -phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; Sethoxydim; siduron; simazine; symmetry; SN 106279, ie, 2- [[-7- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-naphthalenyl] -oxy] -propionic acid and its methyl ester; sulfentrazon (FMC-97285, F-6285); sulfazuron; sulfometuron-methyl; Sulfosate (ICI-A0224); TCA; tebutam (GCP-5544); tebutiuron; terbacil; terbucarb; terbuclor; terbume-ton; terbuthylazine; terbutrin; TFH 450, ie, N, N-diethyl-3- [(2-ethyl-6-methylphenyl) -sulfonyl] -lH-1, 2,4-triazole-l-carboxamide; Tenilchlor (NSK-850); triazafluron; tizopir (Mon-13200); tidiazimin (SN-124085); tifensulfuron-methyl; tioben-carb; thiocarbazil; tralcoxidim; trialate; triasulfuron; triazophenamide; tribenuron-methyl; triclopyr; tridifan; trietazine; trifluralin; trisulfuron and esters (eg the methyl ester, DPX-66037); tri eturon; tsitodef; vernolate; WL 110547, i.e., 5-phenoxy-l- [3- (trifluoromethyl) -phenyl] -1H-tetrazole; UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127 and KIH-2023. The commercial formulations are applied, if appropriate, in a form which is generally diluted, for example, with water in the case of powder applied by spraying, emulsifiable concentrates, dispersions and granules dispersible in water. Powder formulations, spreadable granules and for inclusion in the soil as well as liquids applied by spraying or spraying are generally not diluted with inert materials before their application. The amount necessary for the application of the compounds of the formula (I) may vary depending on external conditions such as temperature, humidity, type of applied herbicide, etc. It can oscillate within wide ranges ranging, for example, from 0.001 to 10.0 kg / ha or more active substance, but preferably lies within the range between 0.005 and 5 kg / ha. A. Chemical examples Abbreviations: data in% and proportions of quantities refer to weight, unless otherwise indicated, in vacuum - at reduced pressure h = hour (s) Example To N-tert-butyl-5-bromome il-2-methoxycarbonylbenzenesulphonamide A solution of 54.8 g (192 mmol) of N-tert-butyl-2-methoxycarbonyl-5-methylbenzenesulfonamide in 420 ml of tetrachloromethane is heated to reflux in an atmosphere of nitrogen protective gas, with the simultaneous incidence of a daylight source and 36 g (202 mmol) of N-bromosucci-nimide and 0.5 g of azobisisobutyronitrile (AIBN) are added, maintaining reflux for 6-8 h. The solution is then filtered and then washed successively with a solution of sodium bisulfite, a solution of sodium hydrogencarbonate and with water, dried over Na 2 SO 4 and concentrated to dryness under vacuum. The residue is crystallized from diisopropyl ether / ethyl acetate and 41.9 g (57%) of N-tert-butyl-5-bromomethyl-2-methoxycarbonylbenzenesulfonamide, of m.p. 88-90 ° C.
Example A2 N-tert-butyl-5-azidomethyl-2-methoxycarbonylbenzenesulfonamide A solution of 25.5 g (70 mmol) of N-tert-butyl-5-bromomethyl-2-methoxycarbonylbenzenesulfonamide and 5.9 g (90 mmol) ) of sodium azide in 240 ml of ethanol is heated to reflux and kept for 6 h. It is then concentrated to dryness and the residue is extracted with water / ethyl acetate. The crude product is digested in diisopropyl ether, yielding 16.6 g (72.5%) of N-tert-butyl-5-azidomethyl-2-methoxycarbonylbenzenesulfonamide, m.p. 63-65 ° C. Example A3 N-tert-butyl-5-aminatomethyl-2-methoxycarbonylbenzenesulfonamide 16.3 g (50 mmol) of N-tert-butyl-5-azidomethyl-2-methoxycarbonylbenzenesulfonamide are dissolved in 300 ml of methanol and hydrogenate over Pd / C (5%). The reaction mixture is filtered and concentrated to dryness. The resulting crude product is purified by column chromatography on silica gel with ethyl acetate / methanol 4: 1 as eluent. 11.2 g (74%) of N-tert-butyl-5-aminomethyl-2-methoxycarbonylbenzenesulfonamide are obtained in the form of a viscous oil.
'N-NMR (100 MHz, CDCl 3): 5 = 1.25 (s, 9H, C (CH 3) 3), 1.80 (broad s, 2H, NH 2), 3.95 (s, 3H, OCH 3) , 4.00 (s, 2H, Ar-CH2), 6.20 (broad s, 1H, S02NH), 7.58 (double d, 1H, Ar-H), 7.80 (d, 1H, Ar- H), 8.10 (double d, 1H, Ar-H). Example A4 N-tert-butyl-5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide To a solution, cooled to 0 ° C, of 2.01 g (6.7 mmol) of N-tert-butyl-5-aminomethyl-2 -methoxycarbonylbenzenesulfonamide and 0.93 ml (6.7 mmol) of triethylamine in 30 ml of dichloromethane are added dropwise 0.63 g (8 mmol) of acetyl chloride, dissolved in 10 ml of dichloromethane, and then kept stirring at room temperature for 2 hours. The reaction solution is washed with water, dried and concentrated to dryness in vacuo. 2.1 g (91%) of N-tert-butyl-5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide are obtained in the form of a viscous oil. 'N-NMR (100 MHz, CDC13): d = 1.25 (s, 9H, C (CH3) 3), 2.05 (s, 3H, C0CH3), 3.95 (S, 3H, OCH3), 4.50 (s, 2H, Ar-CH2), 6.15 (S, 1H, S02NH), 6.38 (broad t, 1H, NH), 7.47 (double d, 1H, Ar-H), 7.75 (d, 1H, Ar-H), 7.95 (double d, 1H, Ar-H). Example A5 5-Acetylamidomethyl-2-methoxycarbonylbenzenesulfonamide A solution of 2.09 g (6.1 mmol) of N-tert-butyl-5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide in 25 ml of trifluoroacetic acid is stirred at room temperature for 14 h it is then concentrated to dryness by evaporation. The residue is crystallized from ethyl acetate and 1.33 g (76%) of 5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide, of m.p. 173-175 ° C. Example A6 N- [4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -5-aceta-mymethyl-2-methoxycarbonylbenzenesulfonamide To a suspension of 1.3 g (4.54 mmol) of 5-acetamido-methyl-2- methoxycarbonylbenzenesulfonamide and 1.25 g (4.54 mmol) of N- (4,6-dimethoxypyrimidin-2-yl) phenyl carbamate in 20 ml of acetonitrile are added at 0 ° C 0.69 g (4.54 mmol). of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU). It is kept at room temperature for 2 h and diluted with water and with diethyl ether, acidified with hydrochloric acid to pH 1-2 and the precipitate that forms is filtered off and dried. 1.32 g (62%) of N - [(4,6-dimethoxypyrimidin-2-yl) aminocarbonyl] -5-acetamidomethyl-2-methoxycarbonylbenzenesulfonamide, of m.p. 149-150 ° C. The compounds described in Tables 1 to 4, which are presented below, are obtained in a manner similar to Examples Al-A6. In the tables, the abbreviations mean the following: "Fp." = melting point Vb. = ns of compound = ns of example Me = methyl Et = ethyl Bu = n-Bu = n-butyl n-C4H9 Ph = phenyl
Table 1 :
X
m. Rs p. f. ° C
1 C02CH3 H CHO H OCH3 OCH3 CH 124-125
2 H OCH 3 CH 3 CH 3 H CH 3 CH 3 CH 4 H CH 3 OC 2 H 5 CH 5 H OCH 3 OCH 3 N 6 H OCH 3 CH 3 N 7 H OCH 3 Cl CH 8 H OCF 2 H CH 3 CH 9 H OCF 2 H OCF 2 H CH 10 H OCH 3 Br CH 1 1 H OCH 3 OC 2 H 5 CH 12 H OCH 3 SCH 3 CH 13 H OCH 3 OC 2 H 5 N 14 H OCH 3 OC 3 H 7 CH 15 H CH 3 Cl CH 16 H Cl OC 2 H 5 CH 17 H OC 2 H 5 OC 2 H 5 CH 18 H C 2 H 5 OCH 3 CH 19 H CF 3 OCH 3 CH 20 H 0CH 2 CF 3 CH 3 CH 21 H OCH 2 CF 3 OCH 3 CH 22 H OCH 2 CF 3 OCH 2 CF 3 CH 23 H 0 CH 2 CF 3 OCH 3 N Rs R 7 Z p. f.
H OCH3 CH (OCH3) 2 CH3 OCH3 OCH3 CH OCH3 CH CH3 CH3 H OCH3 OCH3 NH C0CH3 CH 149-150 H OCH3 H CH3 CH3 CH3 CH CH CH H H CH3 OC2H5 OCH3 OCH3 NH OCH3 OCH3 CH3 NH Cl H CH OCF2H CH3 CH H 0CF2H OCF2H CH H OCH3 Br CH H OCH3 OC2H5 CH H OCH3 SCH3 CH H OCH3 OC2H5 NH OCH3 OC3H7 CH H CH3 Cl CH H Cl OC2H5 CH H OC2H5 OC2H5 CH H C2H5 OCH3 CH H CF3 OCH3 CH H OCH2CF3 CH3 CH H 0CH2CF3 OCH3 OCH2CF3 OCH2CF3 H CH CH NH H OCH3 OCH3 CH 0CH2CF3 (OCH3) 2 CH3 CH OCH3 OCH3 OCH3 CH3 CH3 CH N CH, H OCH3 OCH3 CHO 171 CH -175 OCH3 H H CH3 CH3 CH 135-140 H CH3 CH3 CH 123-126 OC2H5 CH H OCH3 OCH3 NH OCH, CH, N 105
R5 z p.f. ° C
94 H Cl OC2H5 CH 95 H OC2H5 0C2H5 CH 96 H C2H5 0CH3 CH 97 H CF3 OCH3 CH 98 H 0CH2CF3 CH3 CH 99 H OCH2CF3 OCH3 CH 100 H 0CH2CF3 0CH2CF3 CH 101 H OCH2CF3 OCH3 N 102 H OCH3 CH (OCH3) 2, CH 103 CH3 OCH3 OCH3 CH 104 CH3 OCH3 CH3 N 105 H S02CH3 H OCH3 OCH3 CH 192-194
106 H OCH 3 CH 3 CH 107 H CH 3 CH 3 CH 108 H OCH 3 OCH 3 N 109 H OCH 3 CH 3 N 110 H OC 2 H 5 NHCH 3 N 111 CH 3 OCH 3 0CH 3 CH 112 CH 3 OCH 3 CH 3 N 113 CH, S 0 2 CH 3 H OCH 3 OCH 3 CH 107-109
114 H OCH 3 CH 3 CH 115 H CH 3 CH 3 CH 116 H OCH 3 OCH 3 N 117 H OCH 3 CH 3 N 118 H OC 2 H 5 NHCH 3 N 119 CH 3 OCH 3 OCH 3 CH 120 CH 3 OCH 3 CH 3 N 121 OH CHO H OCH 3 OCH 3 CH 122 H OCH 3 CH 3 CH 123 H CH 3 CH 3 CH 124 H OCH 3 OCH 3 N 125 H OCH 3 CH 3 N 126 H OC 2 H 5 NHCH 3 N 127 CH 3 OCH 3 OCH 3 CH 128 CH 3 OCH 3 CH 3 N mp, p. f. ° c R "R5
129 OCH, CHO H OCH 3 OCH 3 CH 142-145 130 H OCH 3 CH 3 CH 131 H CH 3 CH 3 CH 132 H OCH 3 0CH 3 N 133 H OCH 3 CH 3 N 134 H OC 2 H 5 NHCH 3 N 135 CH 3 OCH 3 OCH 3 CH 136 CH 3 OCH 3 CH 3 N 137 OH COCH 3 H OCH 3 OCH 3 CH 138 H OCH 3 CH 3 CH 139 H CH 3 CH 3 CH 140 H OCH 3 OCH 3 N 141 H OCH 3 CH 3 N 142 H OC 2 H 5 NHCH 3 N 143 CH 3 OCH 3 OCH 3 CH 144 CH 3 OCH 3 CH 3 N 145 OCH, COCH 3 H OCH 3 OCH 3 CH 1 95-196 146 H OCH 3 CH 3 CH 147 H CH 3 CH 3 CH 148 H OCH 3 OCH 3 N 149 H OCH 3 CH 3 N 150 H OC 2 H 5 NHCH 3 N 151 CH 3 OCH 3 0CH 3 CH 152 CH 3 OCH 3 CH 3 N 153 H COC 2 H 5 H OCH 3 OCH 3 CH 150-152 154 H OCH 3 CH 3 CH 155 H OCH 3 OCH 3 N 156 H OCH 3 CH 3 N 157 CH, H OCH 3 OCH 3 CH 158 H OCH 3 CH 3 CH 159 H OCH 3 OCH 3 N 160 H OCH 3 CH 3 N 161 H COCH 2 OCH 3 H OCH 3 OCH 3 CH 162 H OCH 3 CH 3 CH 163 H OCH, OCH, N mp. R «R5 p. f. ° C
164 H OCH 3 CH 3 N 165 CH, H OCH 3 OCH 3 CH 166 H OCH 3 CH 3 CH 167 H OCH 3 OCH 3 N 168 H OCH 3 CH 3 N 169 H COC02C 2 H 5 H OCH 3 OCH 3 CH 170 H OCH 3 CH 3 CH 171 H OCH 3 OCH 3 N 172 H OCH 3 CH 3 N 173 CH, H OCH 3 0CH 3 CH 174 H OCH 3 CH 3 CH 175 H OCH 3 OCH 3 N 176 H OCH 3 CH 3 N 177 H COCF 3 H OCH 3 OCH 3 CH 158 178 H OCH 3 CH 3 CH 179 H OCH 3 OCH 3 N 180 H OCH 3 CH 3 N 181 CH, H OCHg OCH 3 CH 144-147 182 H 0CH 3 CH 3 CH 183 H OCH 3 OCH 3 N 184 H OCH 3 CH 3 N 185 H COOCH 3 H OCH 3 OCH 3 CH 1 60-1 61 186 H OCHg CH 3 CH 187 H OCH 3 OCH 3 N 188 H OCH 3 CH 3 N 189 CH, H OCH 3 OCH 3 CH 157-159 190 H OCH 3 CH 3 CH 191 H OCH 3 OCH 3 N 192 H OCH 3 CH 3 N 193 H CONHC 2 H 5 H OCH 3 OCH 3 CH 194 H OCH 3 CH 3 CH 195 H OCH 3 OCH 3 N 196 H OCH 3 CH 3 N 197 CH, H OCH 3 OCH 3 CH 198 H OCH3 CH3 CH mp. X p.f. ° c
199 H 0CH 3 OCH 3 O 200 H OCH 3 CH 3 N 201 H CSNHC 2 H 5 H OCH 3 OCH 3 CH 202 H OCH 3 CH 3 CH 203 H OCH 3 OCH 3 N 204 H OCH 3 CH 3 N 205 CH, H OCH 3 OCH 3 CH 206 H OCH 3 CH 3 CH 207 H OCH 3 OCH 3 N 208 H OCH 3 CH 3 N 209 H S02NHCH 3 H OCH 3 OCH 3 CH 210 H OCH 3 CH 3 CH 211 H OCH 3 OCHg N 212 H OCH 3 CH 3 N 213 CH, H OCH 3 OCHg CH 171-173
214 H OCH 3 CH 3 CH 215 H OCH 3 OCH 3 N 216 H OCH 3 CH 3 N 217 H S02N (CH 3). H OCH3 OCH3 CH 1 62
218 H OCH 3 CH 3 CH 219 H OCH 3 OCH 3 N 220 H OCH 3 CH 3 N 221 CH, H OCH 3 OCH 3 CH 127-129
222 H OCH3 CH3 H OCH3 OCH3 CH 223 N 224 H OCH3 CH3 N H OCH3 OCH3 -CH2CH2CH2CO- 225 CH 226 H OCH3 CH3 H OCH3 OCH3 CH 227 N 228 H OCH3 CH3 N H OCH3 OCH3 -CHCH2CH2S02- 229 CH 230 H OCH3 CH3 CH 231 H OCH 3 OCH 3 N 232 H OCH 3 CH 3 N 233 -CH 2 CHCH 2 CH 2 CO-H OCH, OCH, CH comp. p. f. ° C
R1 R7 X Y z
. 234 H 0CH 3 CH 3 CH 235 H OCH 3 OCH 3 N-236 H OCH 3 CH 3 N 237"2 2 2 ^ 2" H OCH 3 OCH 3 CH 238 H OCH 3 CH 3 CH n 239 H OCH 3 OCH 3 N 240 H OCH 3 CH 3 N 241 -CH 2 CH 2 OCH 2 CH 9"H OCHg OCH 3 CH 242 H OCH 3 CH 3 CH 243 H OCH 3 OCH 3 N 244 H OCH 3 CH 3 N 245 H COC 3 H-, H OCH 3 OCH 3 CH 246 H OCH 3 CH 3 CH 247 H OCH 3 OCH 3 N 248 H OCH 3 CH 3 N 249 CH, H OCH 3 OCH 3 CH 250 H OCH 3 CH 3 CH 251 H OCH 3 OCHg N "252 H OCH 3 CH 3 N 253 H COCH 2 Cl H OCH 3 OCH 3 CH 144-145
254 H OCH 3 CH 3 CH 255 H OCHg OCH 3 N 256 H OCH 3 CH 3 N 257 CH, H OCH 3 OCH 3 CH 138-140
258 H OCH 3 CH 3 CH 259 H OCH 3 OCH 3 N 260 H OCH 3 CH 3 N 261 H COCHCI 2 H OCH 3 OCH 3 CH 262 H OCH 3 CH 3 CH 263 H OCH 3 OCH 3 N 264 H OCH 3 CH 3 N 265 CH, H OCH 3 OCH 3 CH 266 H OCH 3 CH 3 CH 267 H OCH 3 OCH 3 N 268 H 0CH 3 CH 3 N mp. Rl R4 R5 R7 X Y Z P - f. ° C
269 H COCCI3 H OCH3 OCH3 CH 270 H OCH3 CH3 CH 271 H OCH3 OCH3 N 272 H OCH3 CH3 N 273 CH H OCH3 OCH3 CH
274 H OCH 3 CH 3 CH 275 H OCH 3 OCH 3 N 276 H OCH 3 CH 3 N 277 H COCH = CH 2 H OCHg OCH 3 CH 278 H OCH 3 CH 3 CH 279 H OCHg OCH 3 N 280 H OCH 3 CH 3 N 281 CH 3 H OCH 3 OCH 3 CH 282 H OCH 3 CH 3 CH 283 H OCH 3 OCH 3 N 284 H OCH 3 CH 3 N 285 H COC = CH H OCH 3 OCH 3 CH 286 H OCHg CH 3 CH 287 H OCH 3 OCH 3 N 288 H OCH 3 CH 3 N 289 CH 3 H OCH 3 OCH 3 CH 290 H OCH 3 CH 3 CH 291 H OCH 3 OCH 3 N 292 H OCH 3 CH 3 N 293 H COC 6 H 5 H OCH 3 OCH 3 CH 294 H OCH 3 CH 3 CH 295 H OCH 3 OCH 3 N 296 H OCH 3 CH 3 N 297 CH, H OCH 3 OCH 3 CH 298 H OCH 3 CH 3 CH 299 H OCHg OCH 3 N 300 H OCH 3 CH 3 N 301 S02C6H5 S02C6H5 H OCH3 OCH3 CH 302 H 0CH3 CH3 CH 303 H OCH3 OCH3 N p. Rl R4 R5 R7 X Y Z p. f. ° C
304"H OCH3 CH3 N 305" S02CH3 S02CH3 H OCH3 OCH3 CH
306"H OCH3 CH3 CH
307"H OCH3 OCH3 N 308" H OCH3 CH3 N 309"H C0CH2Br H OCH3 OCH3 CH
310"H OCH 3 CH 3 N 31 1 CH 3 H OCH 3 OCH 3 CH 312 H OCH 3 CH 3 N 313 H COCH 2 F H OCH 3 OCH 3 CH 314 H OCH 3 CH 3 N 315 CH 3 H OCH 3 OCH 3 CH 316 H OCH 3 CH 3 N 317 H COCH 2 C --- CH H OCH 3 OCH3 CH 318 H OCH3 CH3 N 319 CH3 H OCH3 OCH3 CH
320"H OCH3 CH3 N 321" H COC02CH3 H OCH3 OCH3 CH
322 H OCH3 CH3 N 323 CH 3 H OCH3 OCH3 CH
324 H OCH3 CH3 N 325"H C02C2H5 H OCH3 OCH3 CH
326 H OCH3 CH3 N 327"CH3 H OCH3 OCH3 CH
328 H OCH3 CH3 N 329"H COSCH3 H OCH3 OCH3 CH
330 H OCH3 CH3 N 331"CH3 H OCH3 OCH3 CH
332 H OCH3 CH3 N 333"H CSOCH 3 H OCH3 OCH3 CH
334"H OCH 3 CH 3 N 335" CH 3 H OCH 3 OCH 3 CH 336 H OCH 3 CH 3 N 337"H CSSCH H OCH 3 OCH 3 CH
338 H OCH3 CH3 N mp. p.f. ° c R £
339 CH, H OCH 3 0CH 3 CH 340 H OCH 3 CH 3 N 341 H COCH (CH 3) 2 H OCH 3 OCH 3 CH 342 H 0CH 3 CH 3 N 343 CH, H 0CH 3 OCH 3 CH 344 * H OCH 3 CH 3 N 345 H COC (CH 3) 3 H OCH 3 OCH 3 CH 346 H OCHg CH 3 N 347 CH, H OCH 3 OCH 3 CH 348 H OCH 3 CH 3 N 349 H CO-Cyclopropyl H OCH 3 OCH 3 CH 350 H OCH 3 CH 3 N 351 CH, H OCH 3 OCH 3 CH 352 H OCH 3 CH 3 N 353 H CO-Cyclobutyl H OCH 3 OCH 3 CH 354 H OCH 3 CH 3 N 355 CH, H OCH 3 OCHg CH 356 H OCH 3 CH 3 N 357 H CO-Ci clopentyl H OCH 3 OCHg CH 358 H OCH 3 CH 3 N 359 CH, H OCH 3 OCH 3 CH 360 H OCH 3 CH 3 N 361 H CO-Cyclohexane H OCH 3 OCHg CH 362 H OCH 3 CHg N 363 CH, H OCH 3 OCHg CH 364 H OCH 3 CH 3 N 365 H CONHCH 2 CH 2 Cl H OCH 3 OCH 3 CH 366 H OCH 3 CH 3 N 367 CH, H OCH 3 OCH 3 CH 368 H OCH 3 CHg N 369 H CSNHCH2CH2CI H OCH3 OCHg CH 370 H OCHg CH3 N 371 CH, - H OCH3 OCH3 CH 372 H OCH3 CHg N 373 H C0NH-n-C4H9 H OCH3 OCHg CH comp. R4 R7 X Z p. f. ° C
374 H OCH3 CH3 N 375 CH3 H OCH3 OCHg CH
376 H OCH3 CHg N 377 H CSNHCH3 H OCH3 OCHg CH
378 H OCH3 CHg N 379 CH3 H OCH3 OCH3 CH
380 H OCH3 CH3 N 381 H CSNHCH2CH = CH2 H OCH3 OCHg CH
382 H OCH3 CHg N 383 CH3 H OCH3 OCHg CH
384 H OCH3 CH3 N 385 CH3 CSNHCH2COCH3 H OCH3 0CH3 CH
386 H OCH3 CHg N 387 CH3 CSNHCH2COC2H5 H OCH3 OCHg CH
388 H OCH3 CHg N 389 CHg CONHCH2COCH3 H OCH3 OCHg CH
390 H OCH3 CHg N 391 CHg CONHCH2COC2H5 H OCH3 OCHg CH
392 H OCHg CH3 N 393 -CONHCH2CO - H OCHg OCHg CH
394 H OCHg CHg N 395 H S02CH2F H OCHg OCHg CH
396 H OCHg CHg N 397 CHg H 0CH3 OCHg CH
398 H 0CH3 CHg N 399 H S02CF3 H OCHg OCHg CH
400 H OCH3 CH3 N 401 CH3 H OCH3 OCHg CH
402 H OCH3 CH3 N 403 H SO2C H5 H OCH3 OCH3 CH
404 H OCHg CH3 N 405 CH3 H OCHg 0CH3 CH
406 H OCHg CH3 N 407 H S02-n-C3H7 H OCHg 0CH3 CH
408 H OCH3 CH3 N comp. R1 R4 R5 R7 X Y Z p. f. ° C
409 CH 3 H OCH 3 OCH 3 CH 410 n H OCH 3 CH 3 N 41 1 OH COC 2 H 5 H OCH 3 OCH 3 CH 412 H OCH 3 CH 3 N 413 OCH 3 H OCH 3 OCH 3 CH 414 H OCH 3 CH 3 N 415 OH C0CH 2 C H OCH 3 OCH 3 CH 416 H OCH 3 CH 3 N 417 « • OCH 3 H OCH 3 OCH 3 CH 41 8 H OCH 3 CH 3 N 419 OH COCFg H OCH 3 OCH 3 CH 420 H OCH 3 CH 3 N 421 OCH 3 H OCH 3 OCH 3 CH 159-1 61
422 H OCH 3 CH 3 N 423 OH COCH 2 OCH 3 H OCH 3 OCH 3 CH p 424 H OCH 3 CH 3 N 425 OCH 3 H OCH 3 OCH 3 CH 130-131
426 H OCH3 CH3 N - 427 OH COC02C2H5 H OCH3 OCH3 CH 428 p H OCH3 CH3 N - 429 OCHg H OCH3 OCH3 CH 1 58-1 59
430 H OCH3 CH3 N 431 OH COOCH3 H OCH3 OCH3 CH 432 H OCH3 CH3 N 433 OCH3 H OCH3 0CH3 CH 137-138
434 H OCH3 CH3 N 435 OH Cyclopropyl H OCH3 OCH3 CH 436 H OCH3 CHg N 437 OCH3 H OCH3 OCHg CH 1 18-120
438 H OCH 3 CH 3 N 439 OH COC 6 H 5 H OCH 3 OCH 3 CH 440"H OCH 3 CH 3 N 441 OCH 3 H OCH 3 OCHg CH n 442 H OCH 3 CH 3 N 443 OH COCH (CH 3) 2 H OCH 3 OCH 3 CH mp. p. f. ° C
R1 R4 Re R7 X Y Z
444 H OCH 3 CHg N 445 OCH 3 H OCH 3 OCHg CH 126-128 446 H OCHg CH 3 N 447 OH COCH = CH 2 H OCHg OCH 3 CH 448 H OCH 3 CH 3 N 449 OCH 3 H OCH 3 OCHg CH 450 H OCHg CH 3 N 451 OH COC --- CH H OCH 3 OCH 3 CH 452 H OCH 3 CH 3 N 453 OCH 3 H OCH 3 OCH 3 CH 454 H OCH 3 CH 3 N 455 OH S02CH 3 H OCH 3 OCH 3 CH 456 H OCH 3 CH 3 N 457 OCH 3 H OCH 3 OCH 3 CH 146-148 458 H OCHg CH 3 N 459 OH S02NHCH 3 H OCH 3 OCH 3 CH 460 H OCH 3 CH 3 N 461 OCH 3 H OCH 3 OCH 3 CH 179-1 80 462 H OCH 3 CH 3 N 463 OH S02N (CH 3) 2 H OCH 3 OCH 3 CH 464 H OCHg CH 3 N 465 OCH 3 H OCH 3 OCH 3 CH 179-180 466 H OCH 3 CH 3 N 467 C 2 H 5 CHO H OCH 3 OCH 3 CH 1 68-170 468 H OCH 3 CH 3 N 469 COCHg H OCHg OCH 3 CH 470 H OCHg CH 3 N 471 Cyclopropyl H OCHg 0CH 3 CH 472 H OCHg CH 3 N 473 COCH 2 Cl H OCHg OCH 3 CH 474 H 0CH 3 CH 3 N 475 COCFg H OCH 3 OCH 3 CH 476 H OCH 3 CH 3 N 477 COOCHg H OCH 3 OCH 3 CH 478 H OCH 3 CH 3 N mp. f. ° C R4 R5 R '
479 COC6H5 H OCHg OCH3 CH 480 H OCHg CH3 N 481 CONHC2H5 H OCHg OCH3 CH 482 H OCHg CH3 N 483 CSNHC2H5 H OCHg OCH3 CH 484 H OCHg CH3 N 485 S02CH3 H OCHg OCH3 CH 1 54-1 55
486 H OCHg CHg N 487 S02NHCH3 H OCHg OCH3 CH 150-152
488 H OCHg CH3 N 489 S02N (CH3) 2 H OCHg OCHg CH 490 H OCHg CH3 N 491 S02C6H5 H OCH3 OCH3 CH 492 H OCH3 CH3 N 493 C0 C Hg H CHO H OCH3 OCH3 CH 494 H OCH3 CH3 N 495 COCHg H 0CH3 OCH3 CH 496 H 0CH3 CH3 N 497 S02CH3 H OCH3 OCH3 CH 498 H OCH3 CH3 N 499 CH, CHO H OCH3 OCH3 CH 500 H 0CH3 CH3 N 501 COCHg H OCH3 OCH3 CH 502 H OCH3 CH3 N 503 S02CH3 H OCH3 0CH3 CH n 504 H 0CH 3 CH 3 N 505 C 2, Hp 5 CHO H OCH 3 0CH 3 CH 506 H OCH 3 CH 3 N 507 COCHg H OCH 3 OCH 3 CH 508 H OCHg CH 3 N 509 S02CH 3 H OCHg OCH 3 CH 510 H OCH 3 CH 3 N 51 OH OH CHO H 0CH 3 OCH 3 CH 512 H OCH3 CH3 N 513 COCHg H OCH3 OCH3 CH comp. . R1 R4 R5 R7 X z p. f. ° c
514 H OCH 3 CH 3 N 515 S02CH 3 H OCH 3 OCH 3 CH 516 H OCH 3 CH 3 N 517 OCH, CHO H OCH 3 OCHg CH 518 H OCH 3 CH 3 N 519 COCH 3 H OCH 3 OCH 3 CH 520 H OCH 3 CH 3 N 521 C02-n-Bu H CHO H OCH 3 OCH3 CH 522 C0N (CH3) 2 CH; CHO H OCH 3 CH 3 N 523 CONHCH 3 H CHO H OCH 3 OCH 3 CH 524 COSCH 3 CH, COCH 3 H OCH 3 CH 3 N 525 C02CH 3 n -Bu CHO H OCH 3 OCH 3 CH 526 H OCH 3 CH 3 N 527 HH OCH 2 CF 3 N (CH 3) 2 N 528 CH, HN 529 H COCH3 H - 530 CH, H 531 S02CH3 H OCH3 OCH3 CH - 532 H OCH3 CH3 N
534 H OCH3 CH3 535 C02CH3 CH3 CHO H OCH3 OCH, CH Salt Na 236-238
536 C02CH3 H S02CH3 H OCH, OCH, CH Salt Na 170-173
537 C02CH3 CH3 S02CH3 H OCH, OCH, CH Salt Na 191
538 C02CH3 OCH3 CHO H OCH, OCH, CH Salt Na 215-216
539 C02CH3 OCH, COCH3 H OCH, OCH, CH Salt Na 224-225
mp. R1 R4 R5 R7 X p. f. ° C
564 C02CH3 C2H5 COCH2OCH3 H OCH3 CHg N 565 C02CH3 C2H5 S02CH3 H OCH3 OCH3 CH 154-155
566 C02CH3 C2H5 S02CH3 H OCH3 0CH3 CH Salt Na 161
567 C02CH3 C2H5 S02NHCH3 H OCH3 OCH3 CH 150-152
568 C02CH3 C2H5 S02NHCH3 H OCH3 0CH3 CH Salt Na 165-168
569 C02CH3 OC2H5 S02CH3 H OCH3 OCH3 CH 163-164
570 C02CH3 OC2H5 S02CH3 H OCH3 OCH3 CH Salt Na 166-168
571 C02CH3 OC2H5 CHO H OCH3 OCH3 CH 165-166
572 C02CH3 OC2H5 CHO H OCH3 OCH3 CH Salt Na 207-208
573 C02CH3 0CH3 CONHPh H OCH3 OCH3 CH 178-179
574 C02CH3 OCH3 CONHEt H OCH3 OCH3 CH 1 55-1 57
575 C02CH3 OCH3 COCCI3 H OCH3 OCH3 CH 1 65-1 68
576 C02CH3 OCH3 COCCI3 H OCH3 OCH3 CH Salt Na 100
577 C02CH3 OCH3 C0CHCI2 H OCH3 OCH3 CH 145-150
578 C02CH3 OCH3 COCHCI2 H OCH3 OCH3 CH Salt Na 235
Table 2
mp. R £ R7 X p. f. ° C
1 C02CH3 H CHO H OCH3 OCH3 CH 142-144
2 H OCH 3 CH 3 CH 3 H CH 3 CH 3 CH 4 H CH 3 0C 2 H 5 CH 5 H OCHg OCH 3 N 6 H OCH 3 CH 3 N 7 H 0CH 3 Cl CH 8 H 0CF 2 H CH 3 CH 9 H OCF 2 H OCF 2 H CH 10 H OCH 3 Br CH 1 1 H OCH 3 OC 2 H 5 CH 12 H OCH 3 SCH 3 CH 13 H OCH 3 OC 2 H 5 N 14 H OCH 3 OC 3 H-, CH 15 H CH 3 Cl CH 16 H Cl OC 2 H 5 CH 17 H 0 C 2 H 5 0C 2 H 5 CH 18 H C 2 H 5 OCH 3 CH 19 H CF 3 OCH 3 CH 20 H OCH 2 CF 3 CHg CH 21 H 0CH2CF3 0CH3 CH 22 H 0CH2CF3 OCH2CF3 CH 23 H OCH2CF3 OCH3 N 24 H OCH3 CH. { OCH3) 2 CH 25 CH 3 OCH 3 0CH 3 CH comp. R4 p. f. ° C
- 26 Ch lg OCHg CHg N 27 H COCH, H OCHg OCHg CH 167-169
. 28 H 0CH 3 CH 3 CH 29 H CH 3 CH 3 CH 30 H CH 3 OC 2 H 5 CH 31 H OCHg OCH 3 N 32 H OCHg CH 3 N 33 H OCH 3 Cl CH 34 H OCF 2 H CH 3 CH 35 H 0CF 2 H OCF 2 H CH 36 H OCHg Br CH 37 H OCH 3 OC 2 H 5 CH 38 H OCH 3 CH 3 CH 39 H OCH 3 OC 2 H 5 N 40 H OCHg OC 3 H 7 CH 41 H CH 3 Cl CH 42 H Cl OC 2 H 5 CH 43 H OC 2 H 5 OC 2 H 5 CH - 44 H C 2 H 5 OCH 3 CH 45 H CF 3 OCH 3 CH "46 H OCH 2 CF 3 CH 3 CH 47 H 0 CH 2 CF 3 OCH 3 CH 48 H OCH 2 CF 3 OCH 2 CF 3 CH 49 H 0 CH 2 CF 3 OCH 3 N 50 H OCHg CH (OCH 3) 2 CH 51 CHg OCHg OCH 3 CH 52 CHg OCHg CHg N 53 CH, CHO H OCHg OCHg CH 160-162
54 H OCHg CH3 CH 55 H CHg CH3 CH 56 H CHg OC2H5 CH 57 H OCHg OCH3 N 58 H OCHg CHg N 59 H OCH3 Cl CH 60 H OCF2H CH3 CH
m. R5 P. f. ° c
97 H CF 3 OCH 3 CH 98 H OCH 2 CF 3 CH 3 CH 99 H OCH 2 CF 3 OCH 3 CH 100 H OCH 2 CF 3 0 CH 2 CF 3 CH 101 H OCH 2 CF 3 OCHg N 102 H OCH 3 CH (OCH 3) 2, CH 103 CH 3 OCH 3 OCHg CH 104 CH 3 OCH 3 CH 3 N 105 H S02CH 3 H OCHg OCH 3 CH 106 H OCHg CH 3 CH 107 H CH 3 CH 3 CH 109 H OCHg CH 3 N 110 H 0C 2 H 5 NHCH 3 N 111 CH 3 OCH 3 OCH 3 CH 112 CH 3 OCH 3 CH 3 N 113 CH, S 0 2 CH 3 H OCHg OCH 3 CH 114 H OCH 3 CH 3 CH 115 H CH 3 CH 3 CH 116 H OCH 3 OCH 3 N 117 H OCH 3 CH 3 N 118 H OC 2 H 5 NHCH 3 N 119 CH 3 OCH 3 OCH 3 CH 120 CH 3 OCH 3 CH 3 N 121 OH CHO H OCH 3 OCH 3 CH 122 H OCH 3 CH 3 CH 123 H CH 3 CH 3 CH 124 H OCH 3 OCH 3 N 125 H OCH 3 CH 3 N 126 H 0 C 2 H 5 NHCH 3 N 127 CH 3 OCH 3 OCH 3 CH 128 CH 3 OCH 3 CH 3 N 129 OCH, CHO H OCH 3 OCH 3 CH 130 H OCH 3 CH 3 CH mp. p. f. ° C R «R £ R7 X
131 H CH 3 CH 3 CH 132 H OCH 3 OCH 3 N 133 H OCH 3 CH 3 N 134 H OC 2 H 5 NHCH 3 N 135 CH 3 OCH 3 OCH 3 CH 136 CH 3 OCH 3 CH 3 N 137 OH COCH 3 H OCH 3 OCH 3 CH 138 H OCH 3 CH 3 CH 139 H CH 3 CH 3 CH 140 H OCHg OCH 3 N 141 H OCH 3 CH 3 N 142"H OC 2 H 5 NHCH 3 N 143 CH 3 OCHg OCH 3 CH 144 CH 3 OCH 3 CH 3 N 145 OCH, COCH 3 H OCH 3 OCH 3 CH 146 H OCH 3 CH 3 CH 147 H CH 3 CH 3 CH 148 H OCH 3 OCH 3 N 149 H OCH 3 CH 3 N 150 H OC2H 5 NHCH 3 N 151 CH 3 OCH 3 OCH 3 CH 152 CH 3 OCH 3 CH 3 N 153 H C 0 C 2 H 5 H OCH 3 OCH 3 CH 196 154 H OCH 3 CH 3 CH 155 H OCH 3 OCH 3 N 156 H OCH 3 CH 3 N 157 CH, H OCH 3 OCH 3 CH 158 H OCH 3 CH 3 CH 159 H OCH 3 OCH 3 N 160 H OCH 3 CH 3 N 161 H C 0 CH 20 CH 3 H 0 CH 3 OCH 3 CH 192-1 95
162 H OCH 3 CH 3 CH 163 H OCH 3 OCH 3 N 164 H OCH 3 CH 3 N 165 CH, n H OCH 3 OCH 3 CH om. p. f. ° C R4 R5 R7 'X Y Z
166 H OCH3 CHg CH 167 H OCHg OCHg N 168 H OCHg CHg N 169 H COC02C2H5 H OCHg OCHg CH 183-185
170 H OCHg CH3 CH 171 H OCHg 0CH3 N 172 H OCHg CH3 N 173 CH H OCHg OCH3 CH 174 H 0CH3 CH3 CH 175 H 0CH3 OCH3 N 176 H 0CH3 CH3 N 177 H COCFg H 0CH3 OCH3 CH 180-182
178 tt H 0CH3 CH3 CH 179 n H 0CH3 OCH3 N 180 H OCHg CH3 N 181 CH, H OCHg OCHg CH 144-147
182 H 0CH3 CH3 CH 183 H OCH3 OCH3 N 184 H 0CH3 CH3 N 185 H COOCHg H OCHg OCH3 CH 178-180
186"H OCHg CH 3 CH 187 H OCHg OCH 3 N 188 H 0CH 3 CH 3 N 189 CH 3 H 0CH 3 OCH 3 CH 190 H 0CH 3 CH 3 CH 191 H OCHg OCH 3 N 192 H OCHg CH 3 N 93 H CONHC 2 H 5 H OCHg OCHg CH 94 H OCH 3 CH 3 CH 95 H OCHg OCH3 N 96 H OCHg CH3 N 97 CH p 3 H OCHg OCHg CH 98 H OCHg CHg CH 99 H OCHg OCHg N 00 H OCHg CHg N ou
z
l? or
co Xu or x
i? CO CN
om R1 R5 p. f. ° C
- 236 H OCHg CHg N 237 2CH S02- H OCHg OCHg CH - 238 H OCHg CHg CH 239 H OCHg OCHg N 240 H OCHg CHg N 241 d 2 CH 2 - H OCHg OCH 3 CH 242 H OCHg CHg CH 243 H OCH 3 OCH 3 N 244 H OCH 3 CHg N 245 H COCgH-, H OCHg OCHg CH 246 H OCHg CHg CH 247 H OCH 3 OCHg N 248 H OCHg CH 3 N 249 CH, H OCHg OCH 3 CH 250 H OCHg CH 3 CH 251 n H OCHg 0CH 3 N 252 H OCH 3 CH 3 N 253 H COCH2CI H 0CH3 OCHg CH 1 70-1 72 254 H OCHg CHg CH 255 H OCHg OCHg N 256 H OCH 3 CHg N 257 CH, H OCHg 0CH 3 CH 258 H OCHg CH 3 CH 259 H OCH 3 OCH 3 N 260 H OCH 3 CH 3 N 261 H COCHCI2 H OCHg OCH3 CH 158-160
262 H OCHg CH 3 CH 263 H OCH 3 OCH 3 N 264 H OCH 3 CH 3 N 265 CH, H OCH 3 OCH 3 CH 266 H OCH 3 CH 3 CH 267 H OCH 3 OCH 3 N 268 n H OCH 3 CHg N 269 H COCCIG H OCH 3 OCHg CH 1 94-1 96
270 H OCHg CH3 CH mp. p. f. ° C
R1
271 H OCH 3 0CH 3 N 272 H OCH 3 CH 3 N 273 CH, H OCH 3 OCHg CH 274 H OCH 3 CH 3 CH 275 H OCH 3 OCH 3 N 276 H OCH 3 CH 3 N 277 H COCH = CH 2 H OCH 3 OCHg CH 278 H OCH 3 CHg CH 279 H OCH 3 OCHg N 280 H OCHg CHg N 281 CH, H OCH 3 OCHg CH 282 H OCH 3 CHg CH 283 H OCH 3 OCH 3 N 284 H OCH 3 CHg N 285 H COC-CH H OCH 3 OCHg CH 286 H OCH 3 CHg CH 287 H OCH 3 OCHg N 288 H OCH 3 CHg N 289 CH, H OCH 3 OCHg CH 290 H OCH 3 CHg CH 291 H OCH 3 OCHg N 292 H OCH 3 CHg N 293 H C 0 C 6 H 5 H OCH 3 OCHg CH 294 H OCH 3 CHg CH 295 H OCH 3 OCHg N 296 H OCHg CHg N 298 H OCHg CH 3 CH 299 H OCHg OCH 3 N 300 H OCHg CH3 N 301 S02C6H5 S02C6H5 H OCHg OCH3 CH 302 H OCHg CH3 CH 303 H OCHg OCH3 N 304 H OCHg CH3 N 305 S02CH3 S02CH3 H OCHg OCH3 CH com. R1 R4 p. f. ° C
• 306 H OCH3 CH3 CH 307 H OCH3 OCH3 N • 308 H OCH3 CH3 N 309 H COCH2Br H OCH3 OCH3 CH 310 H OCHg CH3 N 31 1 CH, H OCHg OCH3 CH 312 H OCHg CH3 N 313 H COCH2F H OCHg OCH3 CH 314 H OCHg CH 3 N 315 CH, H OCHg OCH 3 CH 316"H OCHg CH 3 N 317 H COCH 2 C B CH H OCHg OCH 3 CH 318 H OCHg CH 3 N 319 CH, H OCH 3 OCH 3 CH 320 H OCH 3 CH 3 N 321 H COC02CH 3 H OCH 3 OCH 3 CH 322"H OCH 3 CH 3 N 323 CH, H OCH 3 OCH 3 CH" 324 H OCH 3 CH 3 N 325 H ^^ 2 ^ * 2 ^ 5 H OCH 3 OCH 3 CH 326 H OCH 3 CH 3 N 327 CH, H OCH 3 OCH 3 CH 328 H OCH 3 CH 3 N 329 H COCH 3 H OCH 3 OCH 3 CH 330 H OCH 3 CH 3 N 331 CH, H OCH 3 OCH 3 CH 332 H OCH 3 CH 3 N 333 H CSOCH 3 H OCH 3 OCH 3 CH 334 H OCH 3 CH 3 N 335 CH, H OCH 3 OCH 3 CH 336 H OCH 3 CH 3 N 337 H CSSCH 3 H OCH 3 OCH 3 CH 338 H OCH 3 CH 3 N 339 CH, H OCH 3 OCHg CH 340 H OCH 3 CHg N mp.! F. ° c
341 H COCH (CH3) 2 H OCHg OCHg CH 195-196
342 H OCHg CH3 N 343 CH, H OCHg OCHg CH 344 H OCHg CHg N 345 H COCICHg.g H OCHg OCHg CH 346 H OCHg CHg N 347 CH, H OCHg 0CH3 CH 348 H OCHg CH3 N 349 H CO-Cyclopropyl H OCHg OCHg CH 202-203
350 H OCHg CHg N 351 CH, H OCHg OCHg CH 352 H OCH3 CHg N 353 H CO-Cyclobutyl H OCH3 OCHg CH 354 H 0CH3 CHg N 355 CH, H 0CH3 OCHg CH 356 H 0CH3 CHg N 357 H CO-Ci clopentyl H 0CH3 OCHg CH 358 H 0CH3 CHg N 359 CH, H 0CH3 OCHg CH 360 H 0CH3 CHg N 361 H CO-Exhlo Cycle H 0CH3 OCHg CH 362 H 0CH 3 CHg N 363 CH, H OCH 3 OCHg CH 364 - H 0CH 3 CHg N 365 H CONHCH2CH2CI H 0CH3 OCHg CH 178-182
366 H 0CH3 CHg N 367 CH, H 0CH3 OCHg CH 368 H 0CH3 CH3 N 369 H CSNHCH2CH2CI H OCH3 OCH3 CH 370 H OCH3 CHg N 371 CH, H OCHg OCHg CH 372 H OCHg CHg N 373 H CONH-n-C4Hg H 0CH3 OCHg CH 183-184
374 H 0CH3 CHg N 375 CH, H OCH, OCH, CH om. R1 R4 R5 R7 X p. f. ° C
- 376 H OCH, CHg N 377 H CSNHCH, H OCH 3 OCH; CH-378 H 0CH 3 CH 3 N 379 CH, H OCHg OCHg CH 380 H OCH 3 CH 3 N 381 H CSNHCH 2 CH = CH 2 H OCH 3 OCH 3 CH 382 H OCH 3 CH 3 N 383 CH, H OCH 3 OCHg CH 384 H OCHg CHg N 385 CH, CSNHCH 2 COCH 3 H OCHg OCHg CH 386 H OCHg CHg N 387 CH, CSNHCH2COC2H5 H OCHg OCHg CH 388 H OCHg CHg N 389 CH, CONHCH2COCH3 H OCHg OCHg CH 390 H OCHg CH3 N 391 CH, CONHCH2COC2H5 H OCHg OCHg CH 392 H OCH3 CHg N 393 -CONHCH , CO- H OCH3 OCHg CH 394 H OCHg CH3 N 395 H S02CH2F H OCH3 OCHg CH 396 H OCH3 CHg N 397 CH, H OCH3 OCHg CH 398 H OCH3 CH3 N 399 H S02CF3 H OCH3 OCH3 CH 400 H OCH3 CH3 N 401 CH , H OCHg OCH3 CH 402 H OCHg CH3 N 403 H S0 C2Hg H OCHg OCH3 CH 404 H OCHg CH3 N 405 CH, H OCHg OCH3 CH 406 H OCHg CH3 N 407 H S02-n-C3H7 H OCH, OCH3 CH 408 H OCHj CH 3 N 409 CH, H OCH, OCH 3 CH 410 H OCH, CH, N p. f. ° C
R «R6 X
OH COC2H5 H OCHg OCHg CH H OCHg CHg N 0CH 3 H OCHg OCH 3 CH H OCHg CH 3 N OH COCH 2 Cl H OCHg OCHg CH H OCH 3 CHg N OCHg H OCH 3 OCHg CH H OCH 3 CHg N OH COCFg H OCH 3 OCHg CH H OCH 3 CHg N OCH 3 H OCH 3 OCHg CH H OCHg CHg N OH COCH 2 OCH 3 H OCHg CH CH CH N N OCH 3 tt H OCHg OCHg CH H OCHg CHg N OH COC02C2H5 H OCHg OCHg CH H OCHg CHg N OCHg H OCHg OCHg CH H OCHg CHg N OH COOCHg H OCH3 OCHg CH H OCHg CHg N OCHg H OCHg OCHg CH H OCHg CHg N OH Cyclopropyl H OCHg OCHg CH H OCHg CHg N OCHg H OCHg OCHg CH H OCHg CHg N OH COC 6 H 5 H OCH 3 OCH 3 CH H OCH 3 CH 3 N OCHg H OCH 3 OCH 3 CH H OCHg CH 3 N OH COCH (CH 3) 2 H OCHg OCH 3 CH H OCHg CH 3 N OCH, H OCHg OCH 3 CH - 446 H OCH 3 CH 3 N 447 OH COCH = CH 2 H OCH 3 OCH 3 CH
- 448 H OCHg CH3 N 449 OCH, H OCHg OCH3 CH 450 H OCH3 CH3 N 451 OH COCHESCH H OCH3 0CH3 CH 452 H OCH3 CH3 N 453 OCH, H OCH3 OCH3 CH 454 H OCH3 CH3 N 455 OH S02CH3 H OCH3 0CH3 CH 456 H OCH 3 CH 3 N 457 OCH, H OCH 3 OCH 3 CH 458 H OCH 3 CH 3 N 459 OH S02NHCH 3 H OCH 3 OCH 3 CH 460 H OCH 3 CH 3 N 461 OCH, H OCH 3 OCH 3 CH 462"H OCH 3 CH 3 N 463 OH S02N (CH 3) 2 H OCH 3 OCH 3 CH 464 H OCH 3 CH 3 N 465 OCH, H OCH 3 OCH 3 CH 466 H OCH 3 CH 3 N 467 C 2 H 5 CHO H OCH 3 OCHg CH 468 H OCH 3 CH 3 N 469 COCH 3 H OCH 3 OCH 3 CH 470 n H OCH 3 CH 3 N 471 Cyclopropyl H OCH 3 OCH 3 CH 472 H OCH3 CH3 N
473 COCH2CI H OCH3 OCH3 CH
474 tt H OCH3 CH3 N
475 COCF3 H OCH3 OCH3 CH
476 H OCH3 CH3 N
477 COOCHg H OCH3 OCHg CH
478 H OCH3 CHg N
479 COC6H5 H OCH3 OCHg CH
480 H OCH3 CH, N p. f. ° C R4
481 CONHC2H5 H OCH3 OCH3 CH 482 n H OCH3 Chg N 483 CSNHC2H5 H OCHg OCHg CH 484 H OCHg Chg N 485 S02CH3 H OCHg OCHg CH 486 H OCHg Chg N 487 S02NHCH3 H OCHg OCH3 CH 488 H 0CH3 Chg N 489 S02N (CH3) 2 H OCH3 OCH3 CH 490 H OCH3 Chg N 491 S02C6H5 H OCH3 OCHg CH 492 n H OCH3 Chg N 493 C0 C Hg H CHO H OCH3 OCHg CH 494 H OCHg Chg N 495 COCHg H OCH3 OCH3 CH 496 H OCH3 Chg N 497 S02CH3 H OCH3 OCHg CH 498 H OCH3 CHg N 499 CH, CHO H OCH3 OCHg CH 500 n H OCH3 CHg N 501 COCHg H OCH3 OCHg CH 502 n H OCHg CHg N 503 S02CH3 H OCHg OCHg CH 504 H OCHg CHg N 505 C2H5 CHO H OCHg OCHg CH 506 n H OCHg Chg N 507 COCHg H OCHg OCHg CH 508 H OCHg CH3 N 509 S02CH3 H OCHg OCH3 CH 510 H OCHg Chg N 51 1 OH CHO H OCHg OCHg CH 512 n H OCHg Chg N 513 COCHg H OCHg OCHg CH 514 n H OCHg CHg N 515 S02CH3 H OCH, OCH, CH mp. p. f. ° C R4
516 tt H OCH 3 CH 3 N 517 OCH CHO H OCH 3 OCH 3 CH 518 H OCH 3 CH 3 N 519 COCH 3 H OCH 3 OCH 3 CH 520 tt H OCH 3 CH 3 N 521 C02-n-Bu H CHO H OMe CH 522 CONMe2 Me H Me N 523 CONHMe HH OMe CH 524 COSMe Me CO-Me H Me N 525 C02Me n-Bu CHO H OMe CH 526 n-Bu H Me N 527 HH OCH2CF3 NMe2 528 Me H 529 H CO-Me H 530 Me H 531 S02CH3 H OCHg OCH3 CH 532 H OCH3 CH3 N
534 H OCH, CH, N
Table 3:
R
p. p. f. ° c
C02CH3 H CHO H OCHg OCHg CH H OCHg Chg CH H CH3 CHG CH H Chg OC2H5 CH H OCHg OCHg NH OCHg Chg NH OCHg Cl CH H OCF2H Chg CH H OCF2H OCF2H CH H OCHg Br CH H OCHg OC2H5 CH H OCHg schg CH H OCHg OC2H5 NH OCHg OC3H7 CH H Cl Cl H H Cl OC2H5 CH H OC2H5 OC2H5 CH H C2H5 OCH3 CH H CFg OCH3 CH H OCH2CF3 CH3 CH H OCH2CF3 OCHg CH H OCH2CF3 OCH2CF3 CH H OCH2CF3 OCHg NH OCHg CH (OCH3) 2 CH 10
o o
p. f. ° C
R4 R5
H H CH OCF2H Chg 0CF2H 0CF2H CH H H OCHg 0CH3 CH Br CH OC2H5 H H OCHg OCHg schg CH OC2H5 OCHg OCgH- NH, CH H CH H Cl Cl Chg OC2H5 OC2H5 OC2H5 CH H CH H CH H OCH3 C2H5 OCH3 CF3 H CH OCH2CF3 CH3 CH H OCH2CF3 OCH3 CH H OCH2CF3 0CH2CF3 CH H OCH2CF3 OCH3 NH OCH3 CH (OCH3) 2, CH CH3 OCH3 OCH3 CH CH3 OCH3 CH3 N CH, COCH3 H OCH3 OCH3 CH H OCHg CH3 CH H CH3 CH3 CH H Chg OC2H5 CH H OCHg OCH3 NH OCH3 CH3 NH OCHg Cl CH H OCF2H CH3 CH H 0CF2H OCF2H CH H OCHg Br CH H OCHg OC2H5 CH H OCHg SCH3 CH H OCHg 0C2Hs NH OCHg OC3H7 CH H CHg Cl CH H Cl OC2H5 CH
mp. R4 R7 X p. f. ° C
130 H OCH 3 CHg CH 131 H CH 3 CHg CH 132 H OCH 3 OCHg N 133 H OCH 3 CH 3 N 134 H OC 2 H 5 NHCH 3 N 135 CH 3 OCH 3 OCH 3 CH 136 CH 3 OCH 3 CH 3 N 137 OH COCH 3 H OCH 3 OCH 3 CH 138 H OCH 3 CH 3 CH 139 H CH 3 CH 3 CH 140 H OCH 3 OCH 3 N 141 H OCH 3 CH 3 N 142 H OC 2 H 5 NHCH 3 N 143 CH 3 OCH 3 OCH 3 CH 144 CHg OCH 3 CH 3 N 145 OCH, COCH 3 H OCH 3 OCH 3 CH 1 6-H OCHg CH 3 CH 147 H CHg CH 3 CH 148 H 0CH 3 OCH 3 N 149"H OCHg CH 3 N 150" H OC 2 H 5 NHCHg N 151 CHg OCH 3 OCHg CH 152 tt CH 3 OCHg CH 3 N 153 H COC 2 H 5 H OCHg OCHg CH 154 H OCHg CHg CH 155 H OCHg OCHg N 156 H OCHg CH 3 N 157 CH, H OCHg 0CH3 CH 158 H OCHg CH3 CH 159 H OCHg OCHg N 160 H OCHg CH3 N 161 H COCH2OCH3 H OCHg 0CH3 CH 162 H OCHg CH3 CH 163 H OCHg OCH3 N 164 H OCH, CH, N mp R4 Rs R7 X p f. ° C
165 CH, H OCHg OCHg CH 166 H OCH 3 CHg CH 167 H OCH 3 OCHg N 168 H OCH 3 CHg N 169 H COC02C2H5 H OCH 3 OCHg CH 170 H OCH 3 CHg CH 171 H OCH 3 OCHg N 172 H OCH 3 CHg N 173 CH, H OCH 3 OCHg CH 174 H OCH 3 CHg CH 175 H OCH 3 OCHg N 176 H OCH 3 CHg N 177 H COCFg H OCH 3 OCHg CH 178 H OCH 3 CHg CH 179 H OCH 3 OCH 3 N 180 H OCH 3 CH 3 N 181 CH, H OCH 3 OCH 3 CH 182 H OCH 3 CH 3 CH 183 H OCH 3 OCH 3 N 184 H OCH 3 CH 3 N 185 H COOCHg H OCH 3 OCH 3 CH 186 H OCH 3 CH 3 CH 187 H OCH 3 OCHg N 188 H OCH 3 CH 3 N 189 CH, H 0CH 3 OCH 3 CH 190 H OCHg CH 3 CH 191 H OCHg OCH 3 N 192 H OCHg CH3 N 193 H C0NHC2HE H OCHg OCH3 CH 194 H OCHg CH3 CH 195 H OCHg OCH3 N 196 H OCHg CH3 N 197 CH, H OCHg OCH3 CH 198 H OCHg CH3 CH 199 H 0CH3 OCH, N
or
na com
- - 235 n H OCH3 OCHg N
236 H OCHg CHg N
"237 -CH2CH CH CH S02- H OCH3 OCH3 CH
238 n H OCH3 CH3 CH
239 n H OCH3 OCH3 N
240 H OCH3 CH3 N
241 n -CH2CH2OCH2CH2- H OCHg OCHg CH
242 n H OCH3 CH3 CH
243 n H OCH3 OCHg N
244 n H OCH3 CHg N
245"H COC3H7 H OCH3 OCHg CH
246 n H OCH3 CHg CH
247 n H OCH3 OCHg N
248 p H OCH3 CHg N
249 n CH, H OCH3 OCHg CH
250 n H OCHg CHg CH
251 H OCHg OCHg N
252 H OCHg CHg N
253 H COCH2CI H OCHg OCHg CH
254 H OCHg CHg CH
255 tt H OCHg OCHg N 256 H OCHg CHg N 257 n CH, H OCHg OCHg CH
258 n H OCH3 CHg CH
259 n H OCH3 OCHg N
260 H OCH3 CHg N
261 H COCHCI, H OCHg OCHg CH
262 H OCHg CHg CH
263 n H OCHg OCH3 N
264 H OCHg CHg N
265 n CH, H OCHg OCHg CH
266 H OCHg CHg CH
267 H OCHg OCHg N
268 n H OCH, CH3 N
269 H coca, H OCH, OCH, CH na com. "R1 R4 R5 R7 X Y Z p.
- "270 H OCHg CH3 CH 271" H OCHg OCH3 N * 272 H OCHg CH3 N 273 n CHg H OCHg 0CH3 CH 274 n H OCHg CH3 CH 275 H OCHg 0CH3 N 276 H OCHg CHg N 277 H COCH = CH2 H OCHg OCHg CH 278 tt H OCHg CH3 CH 279 tt H OCHg OCHg N 280 tt H OCHg CHg N 281 CHg "H OCHg OCHg CH 282 H OCHg CHg CH 283 H OCHg OCHg N 284 H OCHg CHg N 285 H COC s CH H OCHg OCHg CH 286 H OCHg CH 3 CH 287 H OCH 3 OCH 3 N 288 H 0CH 3 CH 3 N 289 CHg H OCH 3 OCH 3 CH 290"H OCH 3 CH 3 CH 291 H OCH 3 OCH 3 N 292 H 0CH 3 CH 3 N 293 H COC 6 H 5 H 0CH 3 OCH 3 CH 294 H 0CH 3 CH 3 CH 295 tt H 0CH3 OCHg N 296 tt H OCH3 CH3 N 297 CHg H OCH3 OCHg CH 298 H 0CH3 CH3 CH 299 H 0CH3 OCH3 N 300 H 0CH3 CH3 N 301 St ^ CgHg S02C6H5 H OCH3 OCHg CH 302 H OCH3 CH3 CH 303 H OCH3 OCH3 N 304 H 0CH3 CH, N na com. - - 305 S02CH3 S02CH3 H OCHg OCHg CH 306 H OCH3 CHg CH "307 H OCH3 OCH3 N 308 H OCH3 CH3 N 309 H COCH2Br H OCH3 OCHg CH 310 tt H OCH3 CHg N 31 1 CH, H OCH 3 OCHg CH 312 H OCH 3 CHg N 313 H COCH 2 F H OCH 3 OCHg CH 314 H OC H 3 CHg N 315 CH, H OCH 3 OCHg CH 316 H OCH 3 CHg N 317 H COCH 2 C- = CH H OCH 3 OCHg CH 318 tt H OCH 3 CHg N 319 CH, H OCH 3 OCHg CH 320 H OCH 3 CHg N 321 H COC02CH 3 H OCH 3 OCHg CH 322 H OCH3 CHg N 323 CH, H OCH3 OCHg CH 324 H OCH3 CHg N 325 H CO2C2H5 H OCH3 OCHg CH
326 H OCH3 CHg N 327 CH, H OCH3 OCHg CH
328 «H OCH3 CHg N
329 H COSCHg H OCH3 OCHg CH
330 H OCH3 CHg N
331 CH, H OCH3 OCHg CH
332 H OCH3 CHg N
333 H CSOCH3 H OCH3 OCHg CH
334 H OCH3 CHg N
335 CH, H OCH3 OCHg CH
336 H 0CH3 CHg N
337 H CSSCH3 H OCHg OCHg CH
338 n H OCHg CHg N
339 CH, H OCHg OCHg CH m. R1 R7 X p. f. ° C
340 H OCHg CH3 N 341 H COCH (CH3) 2 H OCHg OCH3 CH 342 H OCHg CHg N 343 CH, H OCHg OCHg CH 344 H OCHg CHg N 345 H COClCHgJg H OCHg OCHg CH 346 H OCHg CH3 N 347 CH, H OCHg OCHg CH 348 H OCHg CHg N 349 H CO-Ci Clopropyl H OCHg OCHg CH 350 H OCHg CHg N 351 CH, H OCHg OCHg CH 352 H OCHg CHg N 353 H CO-Cyclobutyl H OCHg OCHg CH 354 H OCHg CHg N 355 CH, H OCHg OCHg CH 356"H OCHg CHg N 357 H CO-Ci clopent? Ls H OCHg OCHg CH 358 H 0CH3 CHg N 359 CH, H 0CH3 OCHg CH 360 H OCH3 CHg N 361 H CO-Ci clo exilo H OCH3 OCHg CH 362 H OCH3 CHg N 363 CH, "H OCH3 OCHg CH 364 H OCH3 CHg N 365 H CONHCH2CH2CI H OCH3 OCHg CH 366 H OCH3 CHg N 367 CH, tt H OCH3 0CH3 CH 368 tt H OCH3 CHg N 369 H CSNHCH2CH2CI H OCH 3 OCH 3 CH 370 H OCH 3 CHg N 371 CH, H OCH 3 OCHg CH 372 H OCH 3 CH 3 N 373 H C0NH-n-C 4 Hg H OCH 3 OCHg CH 374"H OCH, CH, N m R 5 R 7 X f.
375 CH, H OCH 3 OCHg CH 376 H OCH 3 CH 3 N 377 H CSNHCHg H OCH 3 OCH 3 CH 378 H OCH 3 CHg N 379 CH, H OCH 3 OCHg CH 380 H OCH 3 CHg N 381 H CSNHCH 2 CH = CH 2 H OCH 3 OCHg CH 382 H OCH 3 CHg N 383 CH, H OCH3 OCHg CH 384 tt H OCH3 CH3 N 385 CH, CSNHCH2COCH3 H OCH3 OCHg CH 386 H OCH3 CHg N 387 CH, CSNHCH2COC2H5 H OCH3 OCHg CH 388 tt H OCH3 CHg N 389 CH, C0NHCH2C0CH3 H OCH3 OCHg CH 390 H OCH3 CHg N 391 CH, CONHCH2COC2H5 H OCH3 OCHg CH 392 H OCH3 CHg N 393 -CONHCH, CO- H OCH3 OCHg CH 394 H OCHg CHg N 395 H S02CH2F H OCHg OCHg CH 396 H OCH3 CHg N 397 CH, H OCHg OCHg CH 398 H OCH3 CHg N 399 H S02CF3 H 0CH3 OCHg CH 400 H OCH 3 CHg N 401 CH, H OCH 3 OCHg CH 402 H OCH 3 CHg N 403 H SO 2 C 2 H 5 H OCH 3 OCHg CH 404 H OCHg CH 3 N 405 CH, H OCHg OCH 3 CH 406 H OCHg CHg N 407 H S02-n-C3H7 H OCHg OCHg CH 408 tt H OCHg CH3 N 409 CH, H OCH, OCH, CH m. R < p. f. ° C
410 tt H OCH 3 CHg N 41 1 OH COC 2 H 5 H OCHg OCH 3 CH 412 H OCH 3 CH 3 N 413 OCH, H OCH 3 OCHg CH 14 H OCH 3 CH 3 N 1 5 OH COCH 2 Cl H OCH 3 OCH 3 CH 1 6 H OCH 3 CH 3 N 1 7 OCH, H OCH 3 OCH 3 CH 18 H OCH 3 CHg N OH OH COCFg H OCH 3 OCHg CH 20 tt H OCHg CHg N 21 OCH, H OCHg OCHg CH 22 H OCHg CHg N 23 OH COCH 2 OCH 3 H OCH 3 OCHg CH 24 H 0 CH 3 CHg N 25 OCH, H OCHg OCHg CH 26 H OCHg CHg N 27 OH COC02C2H5 H OCHg OCHg CH 28 H OCHg CHg N 29 OCH, H OCH 3 OCHg CH 30 n H OCH 3 CHg N 31 OH COOCH 3 H OCH 3 OCHg CH 32 H OCHg CHg N 33 OCH, H OCHg OCHg CH 34 H OCHg CHg N 5 OH Cyclopropyl H OCHg OCH, CH 6 H OCHg CHg N 7 OCH, H OCHg OCHg CH 8 tt H OCHg CHg N 9 OH COC 6 H 5 H OCH, OCHg CH 0 H OCH 3 CHg N 1 OCH, H OCHg OCHg CH 2 H OCHg CHg N 3 OH COCH (CH 3) 2 H OCHg OCHg CH 4 H OCH, CH, N m. p. f. ° c R < R5
445 OCH, H OCH 3 OCH 3 CH 446 H OCH 3 CH 3 N 447 OH COCH = CH, H OCH 3 0CH 3 CH 448 H OCH 3 CH 3 N 449 OCH, H OCH 3 0CH 3 CH 450 H OCH 3 CH 3 N 451 OH COCsCH H OCH 3 OCH 3 CH 452 H OCH 3 CH 3 N 453 OCH, H OCH3 OCH3 CH 454 H OCH3 CHg N 455 OH S02CH3 H OCH3 OCHg CH 456 H OCH3 CHg N 457 OCH, H OCH3 OCHg CH 458 H OCH3 CHg N 459 OH S02NHCH3 H OCHg OCHg CH 460 H OCHg CHg N 461 OCH, H OCHg OCHg CH 462 H OCHg CHg N 463 OH S02N (CH3) 2 H OCHg OCHg CH 464 H OCHg CHg N 465 OCH, H OCHg OCHg CH 466 H OCHg CHg N 467 C2H5 CHO H OCHg OCHg CH 468 n H OCHg CHg N 469 COCH 3 H OCHg OCHg CH 470 n H OCHg CHg N 471 Cyclopropyl H OCHg OCHg CH 472 H OCHg CHg N 473 COCH 2 Cl H OCHg OCHg CH 474 H OCHg CHg N 475 COCF, H OCHg OCH 3 CH 476 H OCH 3 CHg N 477 COOCH 3 H OCH3 OCHg CH 478 H OCH3 CHg N 479 COC6HE H OCH, OCH, CH * - 480 H OCH3 CH3 N
481 CONHC2H5 H OCH3 OCH3 CH
- 482 H OCH3 CHg N
483 n n CSNHC2H5 H OCH3 0CH3 CH
484 n H OCH3 CHg N
485 w S02CH3 H OCH3 OCH3 CH
486 H OCH3 CHg N
487 S02NHCH3 H OCH3 OCHg CH
488 H OCH3 CHg N
489 S02N (CH3) 2 H OCH3 OCHg CH
490 tt tt H OCH3 CHg N
491 S02C6H5 H 0CH3 OCHg CH
492 tt tt H OCH3 CH3 N
493 CO2C H5 H CHO H OCHg OCHg CH
494 H OCH3 CHg N
495 B COCHg H OCHg 0CH3 CH
496 H OCHg CH3 N
497 S02CH3 H OCH3 0CH3 CH
498 n H OCHg CH3 N
499 CHg CHO H OCHg 0CH3 CH
500 H OCHg CH3 N
501 COCH3 H OCHg OCHg CH
502"H OCHg CHg N
503 tt S02CH3 H OCHg OCHg CH
504 H OCHg CHg N
505 C2H5 CHO H OCHg OCHg CH
506 H OCHg CHg N
507 n COCH3 H OCHg OCHg CH
508 H OCHg CHg N
509 S02CH3 H OCHg OCHg CH
510 H OCHg CH3 N
511 OH CHO H OCHg OCH3 CH
512 H OCHg CH3 N
513 COCH3 H OCHg 0CH3 CH
514 H OCHg CH, N na com. p. f. ° C
R1 R4 R £
- * 515 S02CH3 H OCH3 OCH3 CH 516 H OCH3 CH3 N * 517 n OCH CHO H OCH3 OCHg CH 518 n H OCH3 CHg N 519 COCH3 H OCH3 OCHg CH 520 H OCH3 CHg N 521 COO-n-Bu H CHO H OMe CH 522 CONMe2 Me H Me N 523 CONH Me HH OMe CH 524 COSMe Me CO-Me H Me N 525 COOMe n-Bu CHO H OMe CH 526 H Me N 527 HH OCH2CF3 NMe2 N 528 Me HN 529 H CO-Me HN 530 Me H t N 531 S02CH3 H OCH3 OCHg CH 532 - H OCH3 CH3 N
534 H OCH, CH, N 535 C02CH3 H COCH3 H OCH, OCH, CH Si, f 270
Table 4:
. ° C C02CH3 H CHO H 0CH3 OCHg CH H OCH 3 CHg CH H CH 3 CH 3 CH H CH 3 OC 2 H 5 CH H OCH 3 OCHg NH OCH 3 CHg NH OCH 3 Cl CH H OCF 2 H CHg CH H 0CF 2 H OCF 2 H CH H OCH 3 Br CH H OCH 3 OC 2 H 5 CH H OCH 3 SCH CH H OCH 3 OC 2 H 5 NH OCH 3 OC 3 H 7 CH H CH 3 Cl CH H Cl OC 2 H 5 CH H OC 2 H 5 OC 2 H 5 CH H C 2 HS OCHg CH H CF 3 OCHg CH H 0 CH 2 CF 3 CH 3 CH H OCH 2 CF 3 OCH 3 CH H OCH 2 CF 3 OCH 2 CF 3 CH H 0 CH 2 CF 3 OCH 3 NH OCH 3 CH (0 CH 3); , CH
mp. R? R4 R5 R7 X Y Z p. f. ° C
95 H OC2H 5 OC 2 H 5 CH 96 H C 2 H 5 OCH 3 CH 97 H CF 3 OCH 3 CH 98 H 0 CH 2 CF 3 CH 3 CH 99 H OCH 2 CF 3 OCH 3 CH 100 H 0 CH 2 CF 3 OCH 2 CF 3 CH 101 H 0 CH 2 CF 3 OCH 3 N 102 H OCH 3 CH (OCH 3) 2 ¡CH 103 CH 3 OCH 3 OCH 3 CH 104 CH3 OCH3 CH3 N 105 H S02CH3 H OCH3 OCH3 CH 106 H OCH3 CH3 CH 107 H CH3 CH3 CH 108 H OCH3 OCH3 N 109 H OCH3 CH3 N 110 H OC2H5 NHCH3 N CH3 OCH3 OCH3 CH 112 CH3 OCH3 CH3 N 113"CH3 S02CH3 H OCH 3 OCH 3 CH 114"» "H OCH 3 CH 3 CH 115 H CH 3 CH 3 CH 116 H OCH 3 OCH 3 N 117 H OCHg CH 3 N 118 H 0C 2 H 5 NHCH 3 N 119" CH 3 OCHg OCH 3 CH 120 CH 3 OCH 3 CH 3 N 121 OH CHO H OCH 3 OCH3 CH not "ft ti H OCH3 CH3 CH 123 H CH3 CH3 CH 124 H 0CH3 OCH3 N 125 H OCH3 CH3 N 126 H OC2H5 NHCH3 N 127 CH3 OCH3 OCH3 CH 128 CH3 OCH3 CH3 N 129" OCH3 CHO H OCH3 OCH3 CH com. - 130 H OCHg CHg CH 131 H CHg CHg CH-132 H OCHg OCHg N 133 H OCHg CHg N 134 H OC 2 H 5 NHCHg N 135"CHg OCHg OCH 3 CH 136 CH 3 0CH 3 CH 3 N 137 OH COCH 3 H OCHg OCHg CH 138 H OCHg CHg CH 139 H CH 3 CHg CH 140 H OCHg OCH 3 N 141 H OCHg CH 3 N 142 H OC 2 H 5 NHCH 3 N 143 CH 3 OCHg OCH 3 CH 144 CH 3 OCH 3 CHg N 145 OCH, COCHg H OCH 3 OCHg CH 146 H OCH 3 CHg CH 147"H CH 3 CHg CH 148 H OCH 3 OCHg N 149 H OCH 3 CHg N 150 H OC 2 H 5 NHCHg N 151 n CH 3 OCHg OCHg CH 152 p CH 3 OCHg CHg N 153 H COC 2 H 5 H OCHg OCHg CH 154 H OCHg CH 3 CH 155 H OCHg 0CH 3 N 156 H OCHg CHg N 157 CH, tt H OCHg OCHg CH 158 H OCHg CHg CH 159 H OCHg OCHg N 160 H OCHg CHg N 161 H COCH 2 OCH 3 H OCHg OCHg CH 162 H OCHg CHg CH 163 H OCHg OCHg N 164 H OCH3 CHg N na comp. R? R4 p. f. ° C
- * 165 CH, H OCHj OCHg CH 166"H OCHg CHg CH 167 tt H OCHg OCH3 N 168 H OCH3 CH3 N 169 H COC02C2H5 H OCH3 OCH3 CH 170 H OCH3 CH3 CH 171 H OCH3 OCHg N 172 H OCH3 CHg N 173 CH , H OCH 3 OCHg CH 174 H OCH 3 CHg CH 175 H OCH 3 OCHg N 176 H OCH 3 CHg N 177 H C 0 CF 3 H OCH 3 OCHg CH 178"H OCH 3 CHg CH 179 - H OCH 3 OCHg N 180 H OCHg CHg N 181 CH, H OCH 3 OCHg CH 182 H OCHg CH3 CH 183"H OCHg OCHg N 184 H OCH3 CHg N 185 H COOCH3 H OCHg OCH, CH 186 H OCHg CHg CH 187 H OCHg OCHg N 188 H OCHg CHg N 189 CH, H OCHg OCHg CH 190 H OCHg CHg CH 191 H OCH 3 OCHg N 192 H OCHg CHg N 193 H CONHC2H5 H OCHg OCHg CH 194 H OCHg CHg CH 195 H OCHg OCHg N 196 H OCHg CHg N 197 CH, H OCHg OCHg CH 198 H OCH, CHg CH 199 tt H OCH, OCH, N? >
fo co 4-
x O cox
x "
X or
m. R4 Rs p. f. ° C
235 H OCH3 OCHg N 236 H OCH3 CHg N 237 -CH2CH2CH, CH S02- H OCH3 OCHg CH 238 H OCH3 CHg CH 239 H OCH3 OCH3 N 240 H OCH3 CHg N 241 -CH2CH2OCH2CH2- H OCHg OCHg CH 242 H OCHg CHg CH 243 H OCH 3 OCHg N 244 H OCH 3 CHg N 245 H COC 3 H 7 H OCHg OCH 3 CH 246 H OCHg CHg CH 247 H OCHg OCHg N 248 H OCHg CHg N 249 CH, H OCHg OCHg CH 250 H OCHg CHg CH 251 H OCHg OCHg N 252 H OCHg CHg N 253 H C0CH2CI H OCHg OCHg CH 254 H OCHg CHg CH 255 H OCH 3 OCHg N 256 H OCH 3 CHg N 257 CH, H OCH 3 OCHg CH 258 H OCH 3 CHg CH 259 H OCH 3 OCHg N 260 H OCH 3 CHg N 261 H COCHCI , H 0CH 3 OCHg CH 262 H OCH 3 CHg CH 263 H OCH 3 OCHg N 264 H OCHg CHg N 265 CH, H OCHg OCHg CH 266 H OCHg CHg CH 267 H OCHg OCHg N 268 H OCHg CHg N 269 H COCCI, H OCH, OCH , CH mp. p. f. ° C
270 H OCH3 CH3 CH 271"H OCHg OCH3 N 272 H OCHg CH3 N 273 CH, H OCHg OCH3 CH 274 H OCHg CHg CH 275 tt H OCHg OCHg N 276 tt H OCH3 CHg N 277 H COCH = CH2 H OCHg OCHg CH 278 tt H OCHg CHg CH 279 tt H OCHg OCHg N 280 H OCH 3 CHg N 281 CH, "H OCH 3 OCHg CH 282 H OCH 3 CHg CH 283 H OCH 3 OCHg N 284 H OCH 3 CHg N 285 H COC = CH H OCH 3 OCHg CH 286 H OCH 3 CHg CH 287 tt H OCHg OCHg N 288 H OCHg CHg N 289 CH, H OCH 3 OCHg CH 290 »H OCH 3 CHg CH 291" H OCH 3 OCHg N 292 H OCH 3 CHg N 293 H COC 6 H 5 H OCH 3 OCHg CH 294 H OCH 3 CHg CH 295 H OCH3 OCHg N 296 H OCH3 CHg N 297 CH, H OCH3 0CH3 CH 298 H OCH3 CH3 CH 299 H OCH3 OCH3 N 300 H OCH3 CH3 N 301 S02C6Hs S02C6H5 H OCH3 0CH3 CH 302 tt H OCH3 CH3 CH 303 H OCH3 OCH3 N 304 tt H OCH3 CH3 N m. R4 R6 R7 X Y Z p. f. ° C
305 S02CH3 S02CH3 H OCHg OCHg CH 306 H OCHg CH3 CH 307 H OCHg OCH3 N 308 H OCHg CHg N 309 H COCH2Br H OCHg OCHg CH 310 H OCHg CHg N 31 1 CH, H OCHg OCHg CH 312 H OCHg CHg N 313 H COCH2F H OCHg OCHg CH 314 H OCHg CHg N 315 CH, H OCHg OCHg CH 316 H OCHg CHg N 317 H COCH 2 C = CH H OCHg OCHg CH 318 H OCH 3 CHg N 319 CH, H OCHg OCH 3 CH 320 H OCHg CHg N 321 H COC02CH3 H OCHg OCHg CH 322 H OCHg CH3 N 323 CH, H OCHg OCHg CH 324 H 0CH3 CHg N 325 H C02C2Hg H 0CH3 OCHg CH 326 H 0CH3 CHg N 327 CH, H OCHg OCHg CH 328 H OCHg CHg N 329 H COSCHg H OCHg OCH 3 CH 330 H OCHg CH 3 N 331 CH, H OCHg OCHg CH 332 H OCHg CHg N 333 H CSOCHg H OCHg OCHg CH 334 H OCHg CHg N 335 CH, H OCHg OCHg CH 336 H OCHg CHg N 337 H CSSCH, H OCHg OCHg CH 338 H OCHg CH3 N 339 CH, H OCH, OCH, CH na comp. R1 R4 R5 R7 X Y p. í Z
- "340« H OCHg CH3 N 341 H COCH (CH3) 2 H OCHg OCH3 CH 342 H OCHg CH3 N 343 CHg H OCHg OCH3 CH 344 H OCHg CHg N 345 H COC (CH3) 3 H OCHg OCHg CH 346 H OCHg CHg N 347 CHg H OCHg OCH 3 CH 348"H OCHg CHg N 349 H CO-C i cloproprium H OCHg OCHg CH 350 H OCHg CHg N 351 CHg H OCH 3 OCHg CH 352 H 0CH 3 CH 3 N 353 H CO-Ci clobut i lo H 0CH3 OCHg CH 354 H OCH3 CHg N 355 CHg H 0CH3 OCHg CH 356"•• H OCH3 CHg N 357 H CO-Ci clopent i lo H 0CH3 OCHg CH 358 H OCH3 CHg N 359 CHg H 0CH3 OCHg CH 360 H 0CH3 CHg N 361 H CO- Gi oexi oo H 0CH3 OCHg CH 362"- H OCHg CHg N 363 CHg H 0CH3 OCHg CH 364 H OCH3 CHg N 365" H CONHCH2CH2CI H OCH3 OCHg CH 366 H OCH3 CHg N 367 CHg H OCH3 OCHg CH 368 H 0CH 3 CHg N 369 H CSNHCH 2 CH 2 Cl H 0 CH 3 OCHg CH 370 H OCH 3 CH 3 N 371 CHg H OCH 3 OCH 3 CH 372 H 0 CH 3 CHg N 373 H C0NH-n-C 4 H 9 H OCH 3 0CH 3 CH 374 H 0 CH 3 CH, N n com. R4 pf. ° C R5 R: • "
H OCHg CHg N OH C0C2H5 H OCHg 0CH3 CH H OCHg CHg N "0CH2 H OCHg 0CH3 CH tt H OCHg CH3 N OH C0CH2CI H OCHg 0CH3 CH H OCH3 CH3 N OCH 3 H OCH3 0CH3 CH H OCH3 CH3 N OH COCFg H OCH3 0CH3 CH tt H OCH 3 CH 3 N OCH 3 H OCH 3 OCH 3 CH H OCH 3 CH 3 N OH COCH 2 OCH 3 H OCH 3 OCH 3 CH H OCH 3 CH 3 N OCH 3 H OCH 3 OCH 3 CH H OCH 3 CH 3 N "OH COC02C 2 H 5 H OCHg OCH 3 CH H OCHg CH 3 N" OCH 3 H OCHg OCHg CH H OCHg CHg N "OH COOCHg H OCHg OCHg CH H OCHg CHg N - OCH 3 H OCH 3 OCHg CH H OCH 3 CH 3 N" OH Cl Clopropium H OCH 3 OCH 3 CH n H 0CH 3 CHg N - OCH n 3 H OCH 3 OCH 3 CH "H OCH 3 CH 3 N" OH COC 6 H 5 H OCHg OCHg CH H OCHg CHg N "OCH tt 3 H OCHg OCHg CH n H OCHg CHg N" OH COCH (CH 3) 2 H OCHg OCHg CH "" tt H OCHg CHg N na com . R1 R4 p. i R5 R7 X Y Z
* * 445 OCHg H OCHg OCH3 CH 446 H OCHg CH3 N 447 OH C0CH = CH2 H OCHg OCHg CH 448 tt H OCHg CHg N 449 OCHg H OCHg OCHg CH 450 H OCHg CHg N 451 OH COC ^ CH H OCHg OCHg CH 452 tt tt H OCHg CHg N 453 OCHg tt H OCHg OCHg CH 454 tt H OCHg CHg N 455 OH S02CH3 H OCHg OCHg CH 456 tt H OCHg CHg N 457"OCHg H OCHg OCHg CH 458 tt H OCHg CHg N 459 OH S02NHCH3 H OCHg OCHg CH 460 H OCHg CHg N 461 OCHg H OCHg OCHg CH 462 H OCHg CHg N 463 OH S02N (CH3) 2 H OCHg OCHg CH 464 H OCHg CHg N 465 OCHg H OCHg OCHg CH 466 H OCHg CHg N 467 C2H5 CHO H OCHg OCHg CH 468 H OCHg CHg N 469 fl tt COCHg H OCHg 0CH3 CH 470 tt H OCHg CH3 N 471 Cyclopropyl H OCHg OCHg CH 472 tt H OCHg CHg N 473 C0CH2CI H OCHg OCHg CH tt 474 n H OCHg CHg N 475 tt COCFg H OCHg OCHg CH 476 H OCHg CHg N 477 COOCHg H OCHg OCHg CH 478 H OCHg CHg N 479 COC6H5 H OCH3 OCHg CH mp p.f. ° C
R1
480 H OCH3 CHg N 481 C0NHC2H5 H OCHg OCHg CH 482 H OCHg CHg N 483 CSNHC2H5 H OCHg OCHg CH 484 »H OCHg CHg N 485 S02CH3 H OCHg 0CH3 CH 486 H OCHg CH3 N 487 S02NHCH3 H OCHg 0CH3 CH 488 H OCH3 CH3 N 489 S02N (CH3) 2 H 0CH3 0CH3 CH 490 H 0CH3 CH3 N 491 S02C6H5 H OCH3 0CH3 CH 492 n H 0CH3 CH3 N 493 C02C Hg H CHO H OCHg 0CH3 CH 494 n H OCHg CH3 N 495 COCH3 H OCHg 0CH3 CH 496 n H 0CH3 CH3 N 497 S02CH3 H 0CH3 OCH3 CH 498 n H OCH3 CHg N 499 CH, CHO H OCHg OCHg CH 500 tt H OCHg CHg N 501 COCH3 H OCHg OCHg CH 502 H OCHg CHg N 503 S02CH3 H OCHg OCHg CH 504 H OCHg CHg N 505 C2H5 CHO H OCHg OCHg CH 506 tt H OCHg CHg N 507 COCH3 H OCHg OCHg CH 508 H OCHg CHg N 509 S02CH3 H OCHg OCHg CH 510 H OCHg CH3 N 51 1 OH CHO H OCHg 0CH3 CH 512 tt H OCHg CHg N 513 COCH 3 H OCHg OCH 3 CH 514 H OCH, CH, N m. p. f. ° C
R1 R4
515 S02CH3 p --- j - .pg OCH3 CH 516 H OCHg CHg N 517 OCH CHO H OCH 3 OCHg CH 518 H OCH 3 CHg N 519 COCH 3 H OCH 3 OCHg CH 520 H OCH 3 CHg N 521 COO-n-Bu H CHO H OMe CH 522 CONMe2 Me H Me N 523 CONHMe HH OMe CH 524 CO-SMe Me CO-Me H Me N 525 CO-OMe n-Bu CHO H OMe CH 526 n-Bu H Me N 527 HH OCH2¡ NMe2 N 528 Me H "N 529 H CO-Me HN 530 Me HN 531" »S02CH3 H OCH3 OCH3 CH 532 H OCH3 CHg N 533 CO, CH, UH OCH3 OCH, CH
534 H OCH, CH, N
B. Formulation Examples a) A dusting product is obtained by mixing 10 parts by weight of a compound of the formula (I) and 90 parts by weight of talc as an inert material and grinding them in a hammer mill. b) A wettable powder, easily dispersible in water, is obtained by mixing 25 parts by weight of a compound of the formula (I), 64 parts by weight of quartz containing kaolin as an inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleylmethyltaurinate as humectant and dispersant and grinding in a needle mill. c) A concentrate easily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) with 6 parts by weight of alkyl phenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol-poly-glycol ether (8 units of ethylene oxide) and 71 parts by weight of mineral paraffinic oil (boiling range eg between 255 and 277 ° C) and grinding them in a friction ball mill to a fineness of 5 microns. d) An emulsifiable concentrate is obtained starting from 15 parts by weight of a compound of the formula (I), 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.
e) A water-dispersible granulate is obtained by mixing 75 parts by weight of a compound of the formula (I), 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight. weight of kaolin, grinding in a pin mill and granulating the powder in a fluidized bed on which sprayed water is sprayed as granulation liquid. f) A water-dispersible granulate is obtained by homogenizing and pretrigating in a colloidal mill 25 parts by weight of a compound of the formula (I), 5 parts by weight of 2,2'-dinaphimethane-6,6 '. sodium disulfonate, 2 parts by weight of sodium oleyl ethyltaurinate, 1 part by weight of polyvinylalcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water and then grinding them in a bead mill and spraying and drying the suspension thus obtained in a spray tower (drizzle) by means of a feed nozzle. C. Biological examples 1. Control of weeds in pre-emergence The seeds or rhizomes of mono- and dicotyledonous weeds were introduced in plastic pots with clay and sandy earth and covered with soil. Then, on the ground surface covering them, the aqueous suspension or emulsion of the compounds of the invention, formulated in the form of wettable powders or concentrates, emulsifiable, with a water consumption equivalent to a volume comprised between 600 and 800 1 / ha, in different dosages. After the treatment, the pots were moved to a greenhouse and kept in good growing conditions for the weeds. The visual assessment of the plants or of the emergency damages took place after the emergence of the trial plants, after 3 to 4 weeks had elapsed, and by comparison with control plants that did not receive any treatment. As evidenced by the results of the tests, the compounds of the invention have good herbicidal control in preemergence against a broad spectrum of weeds and lawns. For example, the compounds of examples 1, 27, 53 to 55, 58, 59, 79, 105, 113, 129, 145, 153, 177, 181, 185, 189, 213, 217, 221, 253, 257, 421, 425, 429, 433, 437, 445, 457, 461, 465, 467, 485, 487, 535 to 543, 547, 551 to 559, 562, 563 and 565 to 578 of Table 1 as well as those of the Examples 1, 27, 53, 79, 153, 161, 169, 177, 181, 185, 253, 261, 269, 341, 349, 365 and 373 of Table 2 as well as examples 27 and 535 of the table 3 and example 53 of table 4 present an excellent herbicidal effect against weeds such as Sinapis alba, Stellaria media, Chry-santhemum segetum and Lolium multiflorum when applied in preemergence in a dose of 0.3 -kg to 0.005 kg of active ingredient per hectare. 2. Post-emergence weed control Seeds or rhizomes of mono- and dicotyledonous weeds were introduced in plastic pots with clay and sandy soil, covered with soil and moved to a greenhouse and kept in good growth conditions. Three weeks after sowing, the experimental plants in the three-leaf stage underwent treatment. The compounds of the formula (I) present invention or their salts, formulated as spraying powders or emulsifiable concentrates with a water consumption equivalent to a volume between 600 and 800 1 / ha, were sprayed onto the green parts of the plants and After a period between 3 and 4 weeks of plant permanence in the greenhouse under optimum growth conditions, the visual evaluation of the effect of the preparations was carried out, by comparison with control plants that did not receive any treatment. The compounds of the invention have a good post-emergence herbicidal control against a broad spectrum of weeds and lawns that are economically important due to the damage they cause. For example, the compounds of examples 1, 27, 53 to 55, 58, 59, 79, 105, 113, 129, 145, 153, 177, 181, 185, 189, 213, 217, 221, 253, 257, 421, 425, 429, 433, 437, 445, 457, 461, 465, 467, 485, 487, 535 to 543, 547, 551 to 559, 562, 563 and 565 to 578 of Table 1 as well as those of Examples 1 , 27, 53, 79, 153, 161, 169, 177, 181, 185, 253, 261, 269, 341, 349, 365 and 373 of Table 2 as well as of Examples 27 and 535 of Table 3 as well as of Example 53 of Table 4 present an excellent herbicidal effect against weeds such as Sinapis alba, Stellaria media, Chry-santhemum segetum and Lolium multiflorum when applied post-emergence in a dose of 0.3 kg to 0.005 kg of active ingredient per hectare. 3. Tolerance by cultivated plants In other greenhouse trials, seeds of a large number of cultivated plants and weeds were placed in a sandy loamy soil and covered with soil. A part of the sherds was treated immediately as described in section 1, the remaining sherds were placed in the greenhouse until the plants removed from two to three true leaves and were then sprayed as described in section 2 with the substances of the formula (I) of the present invention in different doses. After four to five weeks of rest in the greenhouse, it was verified by visual inspection that the compounds of the present invention did not damage dicot crops such as soybean, cotton, rapeseed, sugar beet or potato, when apply in pre- or postemergence, even with high doses of active ingredient. Some substances were also mild with cereal crops, such as, for example, barley, wheat, rye, common sorghum, corn or rice. The compounds of the formula (I) thus exhibit a high selectivity when applied to control unwanted plant growth in crops of agricultural interest.
Claims (9)
- NOVELTY OF THE INVENTION CLAIMS Compounds of the formula (I) and their salts, wherein R means CO-Q-R8, R2, R3, independently of each other, mean H or C, -C4 alkyl, R4 signifies H, C, -C8 alkyl which may be unsubstituted or substituted by one or more residues of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfinyl, (C 1 -C 4) alkylsulfonyl, (C-alkoxy, -C4) - carbonyl and CN, or C3-C6 alkenyl which may be unsubstituted or substituted by one or more halogen atoms, or C3-C6 alkynyl which may be unsubstituted or substituted by one or more halogen atoms, or hydroxy, C, -C 4 alkoxy, (C 1 -C 4) alkyloxycarbonyl or (C 1 -C 4) alkylsulfonyl, taking into account that each of the three last mentioned moieties is unsubstituted or substituted in its alkyl part by one or more halogen atoms or by C, -C4 or (C 1 -) alkyloxy, or phenylsulfonyl, given that the phenyl moiety is unsubstituted or substituted, And R5 means (C 1 -C 4 alkyl) -sulfonyl or (C 4 -C 4 alkenyl) sulfonyl, given that each of the last-mentioned radicals is unsubstituted or substituted by one or more halogen atoms or by alkoxy Cj-C4 or (C 1 -C 4 alkyl) -thio; or phenylsulfonyl or 1-enylcarbonyl, taking into account that the phenyl radical of each of the two radicals mentioned a is unsubstituted or substituted; either mono- or di- (alkyl-C, -C4) -aminosulfonyl or (C-C6 alkyl) -carbonyl, taking into account that each of the three residues mentioned last is unsubstituted or substituted by one or several residues of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfinyl, (C 1 -C 4) alkylsulfonyl, (alkyl) -C, -C4) -carbonyl, (C-C4-alkoxy) -carbonyl and CN; or formyl, a group of the formula -CO-CO-R ', in which R' signifies H, OH, C, -C4 alkoxy or C, -C4 alkyl, or (C3-C6 cycloalkyl) -carbonyl (C2-C6-alkenyl) -carbonyl or (C2-C6-alkynyl) -carbonyl, taking into account that each of the three last-mentioned radicals is unsubstituted or substituted by one or more halogen atoms; or else a group of the formula W W W - C - T - R9, - C - NR10Rp or - C - N (RI2) 2 or R4 and R5, together, form a chain of formula (-CH2) mB- or -Bl- (C2) ml-B -, given that the chain can be unsubstituted or substituted by one or more C, -C3 alkyl radicals and m is the number 3 or 4, or m1 is the number 2 or 3, as well as W means an oxygen atom or of sulfur, B, B1 independently of each other, mean S02 or CO, Q means O, S or -NR13-, T means O or S, R6 means H, C ^ C ^ alkyl, C-C4 alkoxy, (C-alkyl, -C4) -carbonyl or (C-C4-alkoxy) -carbonyl, taking into account that each of the 4 radicals mentioned last may be unsubstituted or substituted in their alkyl part with one or more halogen atoms; or halogen, N02 or CN, R7 signifies H or CH3, R8 signifies H, C, -C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl, given that each of the three last mentioned residues is unsubstituted or substituted by one or more residues from the series consisting of halogen, C, -C4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -carbonyl or (C-C 4 alkoxy) -carbonyl, R9 means C, -C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl, given that each of the three last-mentioned residues is unsubstituted or substituted by one or more residues of the series formed by halogen, C 1 -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -carbonyl and (C 1 -C 4 alkoxycarbonyl, R 10, R 11, independently of each other, mean H, Cj-C4 alkyl, C3-C4 alkenyl or C3-C4 alkynyl, given that each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals from the series consisting of halogen, C1-alkoxy -C4, (alkyl-e ,,) -thio, ( alkyl-Cj-C ^ -carbonyl and (C ^, alkoxy) carbonyl, the residues R12, together with the N atom, form a 5- or 6-membered heterocyclic ring, which may have other heteroatoms of the series consisting of N, O and S in their possible oxidation degrees, and is unsubstituted or substituted by C-alkyl, -C4 or by the oxo group or is condensed with a benzene, R13 means H, C3-C4 alkenyl alkyl or C3-C4 alkynyl, given that each of the three last mentioned moieties is unsubstituted or substituted by one or several remains of the series formed by halogen, CX-C alkoxy and (Cj-Q alkyl) -thio, is a remainder of the formula one of the radicals X and Y is hydrogen, halogen, C, -C 3 alkyl or C 1 Cj alkoxy, given that the two last-mentioned radicals are unsubstituted or substituted one or more times by halogen or once by alkoxy C, -C3, and the second of residues X and Y is hydrogen, C, -C3 alkyl, C, -C3 alkoxy or (C, -C3 alkyl) -thio bearing in mind that the three last mentioned moieties they are unsubstituted or substituted one or more times by halogen or one or two times by C 1 -C 3 alkoxy or C 1 -C 4 alkyl, or a t residue of the formula NR 14 R 15, C 3 -C 6 cycloalkyl, C 2 -C 4 alkenyl , C2-C4 alkynyl, C3-C4 alkenyloxy or C3-C4 alkynyloxy, Z stands for CH or N, R14 and R15, independently of each other, denote H, C, -C3 alkyl or C3-C4 alkenyl, X1 means CH3, 0CH3 , oC2H5 or 0CHF2, means -O-, -CH2-, Xz means CH3, C2H5 or CH2CF3, means 0CH3, OC2H5, SCH3, SCH2CH3, CH3 or C2H5, XJ means CH3 or 0CH3, Y3 means H or CH3, X4 means CH3 , 0CH3, 0C2H5, CH2OCH3 or Cl, Y4 means CH3, 0CH3, 0C2H5 or Cl and Y5 means CH3, C2H5, 0CH3 or Cl.
- 2. Compounds or their salts according to claim 1, characterized in that R4 means H, Cj-Q alkyl, which may be unsubstituted or substituted by one or more residues of the series consisting of halogen, C, -C 4 alkoxy, (C 1 -C 4 alkyl) -thio, (C 1 -C 4 alkyl) -sulfonyl, (C 4 -C 4 alkoxy) carbonyl and CN, or C3-C4 alkenyl, C3-C4 alkynyl, hydroxy, C, -C4 alkoxy, (C1-C4 alkyl) -carbonyl or (Cj-C4 alkyl) -sulfonyl, given that each of the five last mentioned moieties is unsubstituted or substituted in its alkyl part by one or more halogen atoms; or phenylsulfonyl, provided that the phenyl moiety is unsubstituted or substituted by one or more moieties of the series consisting of halogen, C, -C 4 alkyl and C 1 -C 4 alkoxy, and R 5 means (C 1 -C 4 alkyl) ) -sulfonyl, (C 1 -C 4 -haloalkyl) -sulfonyl, phenylsulfonyl or phenylcarbonyl, taking into account that the phenyl residue of each of the two last-mentioned residues is unsubstituted or substituted by one or more residues of the series formed by halogen, Cj- alkyl, and C? -C4 alkoxy; either mono- or di- (alkyl-Cj-C4) -aminosulfonyl or (C-C6 alkyl) -carbonyl, which is unsubstituted or substituted by one or more halogen atoms or C? -C4 alkoxy and (alkyl) -C! - C4) -thio; or formyl, OHC-CO-, 2-oxo- (C3-C5 alkanoyl), (C4-C4 alkoxy) -oxalyl, (C3-C6 cycloalkyl) -carbonyl, (C2-C4 alkenyl) -carbonyl or (C2-C4 alkynyl) -carbonyl or a group of the formula II II - C - T - R9, - C - NR10Rn O - C - N (R, 2) 2 means O or S, R6 means H, C ^ q alkyl, C1 - C4 haloalkyl, C - C4 alkoxy , haloalkoxy C ^ Q, or halogen, R8 independently of each other, means C, -C4, C3-C4 alkenyl or C3-C4 alkynyl, which is unsubstituted or substituted by one or more halogen atoms, or by C3 alkenyl -C4 or C3-C4 alkynyl, R9 means H, C, -C4 alkyl, which is unsubstituted or substituted by one or more halogen atoms or by C, -C4 alkoxy, (C1-C4 alkyl) -thio, ( C 1 -C 4 alkoxycarbonyl or (C 1 -C 4 alkylcarbonyl), R 10, Rp, independently of each other, mean H, C, -C 4 alkyl, which is unsubstituted or substituted by one or more halogen atoms; or C3-C4 alkenyl or C3-C4 alkynyl, given that at least one of the radicals R10 and Rp is other than hydrogen, the radicals R12, together with the N atom, form a heterocyclic ring of 5 or 6 links, which may have another heteroatom of the series consisting of N, O and S in their possible oxidation degrees, and is unsubstituted or substituted by alkyl 0, -0, and R13 independently of each other, means H, alkyl C , -C4, which is unsubstituted or substituted by one or more halogen atoms; or C3-C4 alkenyl or alkynyl -3-4.
- 3. Compounds or their salts according to claim 1 or 2, characterized in that R4 means H, Cj-C4 alkyl or C-alkoxy, -C4 R5 means (C-C4 alkyl) -sulfonyl, CHO, (C-alkyl, - C4) - carbonyl which is unsubstituted or substituted by one or more halogen atoms; or (C 1 -C-alkoxy-oxalyl, (C 3 -C 6 cycloalkyl) -carbonyl or a group of the formula - C - T - R9, - C - NRI0Rp or - C - N (RI2) 2 given that W, T, from R9 to R12 have the meanings defined above for formula (I), R ° means H, alkyl C, -C3, C, -C3 alkoxy or halogen, is a residue of the formula Z means CH or N, and one of the radicals X and Y means halogen, C, -C2 alkyl, C, -C2 alkoxy, OCF2H or OCH2CF3 and the second of the residues X and Y means alkyl Cj-C2, alkoxy C] - ^ or haloalkoxy C-? ~ C2. Process for obtaining compounds of the formula (I) or their salts according to claim 1, characterized in that a) a compound of the formula (II) is reacted with a heterocyclic carbamate of the formula (III) R * -O-CO-NR7-A (III) in which R * means optionally substituted phenyl or C 1 -C 4 alkyl, or b) a phenylsulfonyl carbamate is reacted of the formula (IV) N R R 5 with an aminoheterocycle of the formula (V) H-NR7-A (V) or c) a sulfonyl isocyanate of the formula (VI) is reacted R2R3C A 5 with an aminoheterocycle of the formula H-NR7-A (V), or d) in a reaction in a single reactor, an aminoheterocycle of the formula H-NR7-A (V) is first reacted with phosgene in the presence of a base and then the intermediate product formed is reacted with a phenylsulfonamide of the formula (II), or e) a sulfonyl chloride of the formula (VII) is reacted R2- \ NR4R with a cyanate of formula M-OCN, where M means NH
- 4, Na or K, and with an aminoheterocycle of the formula H- NR7-A (V) in the presence of a base, f) a sulfonamide of the formula (II) mentioned is reacted with a (thio) -isocyanate of the formula (V) = C = N - A (V) in the presence of a base, given that in formulas (II) - (VII) and (V) the residues or groups R1 - R7, A or have the same defined meaning for the formula (I) and in the variants a) - e) the compounds of the formula (I) are first obtained in which it is 0.
- 5. Herbicide and plant growth regulator, characterized in that it contains less a compound of the formula (I) or a salt thereof according to one of the claims 1 to 3 and the customary formulation auxiliaries for plant protection products.
- 6. Process of weed control or plant growth regulation, characterized in that an effective amount of at least one of the compounds of the formula (I) or a salt thereof according to one of the claims 1 to 3 is applied, on harmful plants or on plants, seeds or soil, on the surface on which the plants grow.
- 7. Use of the compounds of the formula (I) or their salts according to one of claims 1 to 3 as herbicides or plant growth regulators.
- 8. Compounds of the formula (II), \ NR R5 in which from R1 to R6 have the meanings defined for formula (I) in claim 1.
- 9. Process for obtaining the compounds of formula (II) according to claim 8, characterized in that a compound of the formula (XV) NR4R5 similarly to the known method for the elimination of the tert-butyl protecting group, given that the radicals R1 to R6 of the formula (XV) have the same meanings defined for the formula (II). ,, In testimony of which I sign the above in this City of Mexico, D.F., on the 14th day of the month of October of 1994. BY HOECHST-SCHERING A.GREVO GMBH HOE / crg *
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4335297.9 | 1993-10-15 |
Publications (1)
Publication Number | Publication Date |
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MXPA94007991A true MXPA94007991A (en) | 1999-02-24 |
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