MXPA00005813A - Substituted triazole, imidazole and pyrazole each as herbicide - Google Patents
Substituted triazole, imidazole and pyrazole each as herbicideInfo
- Publication number
- MXPA00005813A MXPA00005813A MXPA/A/2000/005813A MXPA00005813A MXPA00005813A MX PA00005813 A MXPA00005813 A MX PA00005813A MX PA00005813 A MXPA00005813 A MX PA00005813A MX PA00005813 A MXPA00005813 A MX PA00005813A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- och
- conh
- haloalkyl
- sch
- Prior art date
Links
- 230000002363 herbicidal Effects 0.000 title claims abstract description 19
- 150000003852 triazoles Chemical class 0.000 title claims abstract description 8
- WTKZEGDFNFYCGP-UHFFFAOYSA-N pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title claims description 6
- 239000004009 herbicide Substances 0.000 title abstract description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000011780 sodium chloride Substances 0.000 claims abstract description 15
- 239000000460 chlorine Substances 0.000 claims description 1749
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 590
- 125000000217 alkyl group Chemical group 0.000 claims description 230
- -1 alkynyl haloalkyl Chemical group 0.000 claims description 159
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 94
- 125000001188 haloalkyl group Chemical group 0.000 claims description 77
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 73
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 29
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 21
- 230000036849 Clc Effects 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 20
- 241000196324 Embryophyta Species 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 18
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 15
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 14
- 201000002674 obstructive nephropathy Diseases 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 13
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 13
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 11
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
- 125000005418 aryl aryl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000004277 1,3-dioxalan-2-yl group Chemical group [H]C1([H])OC([H])(*)OC1([H])[H] 0.000 claims description 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 6
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 5
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N furane Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 101700037472 nhr-6 Proteins 0.000 claims description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000575 pesticide Substances 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 125000004806 1-methylethylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 239000003337 fertilizer Substances 0.000 claims description 2
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 1
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims 1
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims 1
- 101710019693 COR6 Proteins 0.000 claims 1
- 101710020095 COR9 Proteins 0.000 claims 1
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 239000001963 growth media Substances 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 150000003217 pyrazoles Chemical class 0.000 abstract description 4
- 150000002460 imidazoles Chemical class 0.000 abstract description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 83
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 61
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 50
- 239000004480 active ingredient Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 230000036880 Cls Effects 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Inorganic materials [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 2
- 240000007842 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 235000005824 corn Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 235000021307 wheat Nutrition 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1,2,3-triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WCRAKJMHCWUABB-UHFFFAOYSA-N 1,2,4-triazol-1-ylmethanol Chemical compound OCN1C=NC=N1 WCRAKJMHCWUABB-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-Triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-Benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- UVJHQYIOXKWHFD-UHFFFAOYSA-N 1,4-Cyclohexadiene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
- OUBKHTIJPWMLIK-UHFFFAOYSA-N 1H-1,2,4-triazol-5-ylmethyl 2-[2-chloro-5-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-4-fluorophenoxy]acetate Chemical compound C1=C(N2C(C3=C(CCCC3)C2=O)=O)C(F)=CC(Cl)=C1OCC(=O)OCC=1N=CNN=1 OUBKHTIJPWMLIK-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention relates to novel heterocyclic compounds and their agronomically suitable salts, methods for the use of these compounds in controlling unwanted plant species, and the use of herbicidal compositions containing these compounds. In particular, the present invention pertains to substituted and unsubstituted triazoles, imidazoles and pyrazoles linked to a heterocyclic substituted benzene group. Such compounds are useful as pre-emergent and post-emergent herbicides.
Description
OTriazoles, Imidazoles and Substituted Pyrazoles, as Herbicides
The present invention relates to novel heterocyclic compounds and their agronomically suitable salts, methods for the use of these compounds and controlling undesired plant species, and the use of herbicidal compositions containing these compounds. Does the presence of unwanted plant species cause substantial damage to the crop? useful, especially to agricultural products that satisfy humans with basic foods and their fiber needs, such as cotton, rice, corn, wheat, soybeans. The current explosion of the population and the global shortage of food and fibers, demand improvements in the efficiency of producing these crops.
The prevention or minimization of a portion of such valuable crops by destroying or inhibiting the growth of unwanted plant species is one way to improve this efficiency. Although many herbicides are available, there is still a need for more effective herbicides. The compounds of the present invention, generally, show a usefully improved level of crop safety in soybeans, corn or wheat, as compared to known compounds. EP 0 083 055 A2, published on July 6, 1983, discloses herbicidal compounds of the following formula (i):
wherein: R. is hydrogen, alkyl, lower cycloalkyl, lower alkyl-cycloalkyl (lower), lower cycloalkyl-lower alkyl, lower alkoxy-alkyl
(lower), lower alkenyl, lower cycloalkenyl, lower cycloalkenyl-lower alkyl, phenyl, cyano-lower alkyl, lower alkynyl, lower alkylidene
amino, lower alkylthio-lower alkyl, benzyl, haloalkyl (lower) or cycloalkylidene (lower) amino; R2 is hydrogen, lower alkyl, lower alkoxy;
X is chlorine or bromine; And it's oxygen or imino; and Z is oxygen or sulfur.
EP 0 273 417 A1, published on July 6, 1988, discloses herbicidal compounds, which have formula (ii):
wherein: each X and Y represents hydrogen or halogen; Z is -SCH (R) COOR1; R is hydrogen, alkyl and R 1 is alkyl, cycloalkyl or alkoxyalkyl or COOQ, where Q is alkyl, or Y and Z form together:
FT or R ° -O CH C N- attached to the phenyl ring, where R 2 is H or alkyl, and R 3 is alkyl, alkenyl or alkynyl.
The present invention relates to novel herbicidal compounds and to methods of their use in controlling unwanted plant species and their use in agricultural herbicide compositions. In particular, the present invention relates to substituted and unsubstituted triazoles, imidazoles and pyrazoles, bonded to a benzene group, substituted with heterocyclic. It has been found that certain triazoles, imidazole and pyrazoles, bonded to a benzene group, substituted heterocyclic, are useful as post-emergence pre-emergence herbicides. These novel compounds are represented by the formula I:
in which R? it is selected from H, F, Br, Cl, N02 and CN; R2 is selected from F, Cl, Br, H and CN; R3 is selected from H and CN; and alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, cycloalkenyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylalkyl, aryl, arylalkyl, heteroaryl heteroarylalkyl, all of which may be further substituted, - R4 and Rs are selected each, independently, of H, halogen and CN; and alkyl, cycloalkyl, haloalkyl, alkoxy, alkylthio, alkylsulfonyl alkyl, alkylsulfinylalkyl, alkylsulfonyl cycloalkyl, alkylsulfinylcycloalkyl, C02R6,
CONR6R13, OR6, SR6, S02R6, NR6R13, S02? R6R13, aryl, arylalkyl, heteroaryl heteroarylalkyl, all of which may be further substituted; R6 is selected from H, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinyl alkyl, alkylsulfonylcycloalkyl, alkyl sulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted;
R7 is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl and C0Ra, all of which may be further substituted; R8 is selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl, alkylsulfonylalkyl, alkyl-sulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted, - R9 is selected from H, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl , alkenyl, alkynyl, haloalkyl and cycloalkyl, all of which may be further substituted; R10 is selected from H, halogen, NH2, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, haloalkyl, CN, C02- (alkyl, CONH (alkyl); CON (alkyl) -, wherein each alkyl may be the same or different, CH2CN, CH2CH = CH2,
CH ^ C = CH, CH2C02 (alkyl), CH ^ OCHj and CH2-1,2,4-triazole, all of which may be further substituted; RX1 is selected from H, CN, alkyl, haloalkyl and
C02 (alkyl); R12 is selected from H, alkyl, C02R6, CONR6R15, OR6 SR6, S02R6_
S02? R6R13 and? R6R13; R13 is H, alkyl, aryl or aralkyl; A is? or CH; B is? or CR10; Z is O, CH (R3), CO, CS, C0? R12 or CSNR12; X is selected from 0, S; NR12, C02, 0CH (R6) C02, SCH (R6) C02, CH = C (halo) C02, CH2CH (halo) C02, CONH, OCH (R6) CONH,
SCH (R CONH, CH = C (halo) CONH and CH2CH (halo) CONH, when Z is CH (R3); X is selected from CO, 0CH (R6) C0, SCH (R6) C0, CH = C (halo) ) C0 and CH2CH (halo) CO, when Z is 0; X is selected from O, S, CO, OCH (R6), CH = C (halo),
CH2CH (halo), CONH, OCH (Rs) CONH, SCH (R6) CONH, CH = (halo) CONH, CH2CH (halo) CONH and NR12, when CO, CS, CO? R12 or XCSNR12; and Q is selected from NR7COR6, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8,
Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16, where Ql is 4, 5, 6, 7-tetrahydroftalimid-2-yl, Q2 is 5, 6, 7, 8-tetrahydro-l, 2, 4 -triazolo [4, 3-a] -pyridin-3 (2H) -one-1-yl, Q3 is 5, 6, 7, 8-tetrahydro-lH, 3H- [1, 3,4] -thiadiazolo [3 , 5- a] pyridazinimin-1-yl, Q4 is 4, 5, 6, 7-tetrahydroimidazo [1, 5-a] pyridin-1, 3- (2H.5H = -dione-1-yl, Q5 is 1 , 6, 8-triazabicyclo [4, 3, 0] -nonano-7, 9-dion-8-yl, Q6 is 5- (1-methylethylene) -2,4-oxazolidindion-3-yl, Q7 is 5- ( 1,1-dimethylethyl) -1,3-oxadiazol-2 (3H) -in-3-yl, Q8 is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazole-5 - (1H) -on-l-yl, Q9 is 2-methyl-l, 2,4-oxadiazolidin-3, 5-dion-4-yl, Q10 is 4-chloro-l-methyl-5-difluoromethoxy-lH -pyrazol-3-yl, Qll is 4-bromo-l-methyl-5-trifluoromethyl-lH-pyrazol-3-yl, Q12 is l-substituted-6-trifluoromethyl-2,4-pyrimidin-3-yl,
Q13 is l-substituted-6-trifluoromethyl-i, 3,5-triazin-2,4-dion-1-yl, Q14 is 4,5-disubstituted-4,5-dihydro-l, 2,4-triazin- 3 (2H) -in-2-yl, Q15 is 4-substituted-l, 2,4-triazin-3, 5 (2H, 4H) -dione-2-yl, and Q16.es 5-methyl-6- oxo-4- (trifluoromethyl) -6H-pyridazin-1-yl. or its agronomically acceptable salts. As used in the present invention, the term "aryl" is defined as a monocyclic or polycyclic ring, selected from benzene, naphthalene, indene, anthracene, indacene, fluorene, acenaphthalene, phenanthrene and azulene. "Heteroaryl" is defined as a ring, monocyclic or polycyclic, selected from furan, thiophene, pyrrole, isoxazole, oxazole, isothiazole, thiazole, pyrazole, imidazole, 1, 2, 3-triazole, 1,2-triazole, tetrazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1, 3, 5-triazine, 1,2,4-triazine, 1, 2, 4, 5-tetrazine, benzofuran, benzothiophene, indole, benzisoxazole, benzoxazole, benzisothiazole, benzothiazole, benzopyrazole, benzimidazole, benzotriazole, 1,2-methylenedioxybenzene, 1,2-ethylenedioxybenzene, quinoline and isoquinoline.
The structures of the heterocyclic "Q" groups,
previously mentioned, are: ionde R..j and R? l are as previously defined.
The term "alkyl" includes branched and straight chain alkyl groups. Typically, the alkyl groups with: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec. -butyl, isobutyl, tere. -butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, isooctyl, nonyl, decyl, undecyl, dodecyl and the like. The term "cycloalkyl" refers to a cyclic aliphatic ring structure, such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and the like. The term "haloalkyl" refers to an alkyl group substituted with one or more halogen groups. The term "halogen" refers to fluorine, chlorine, bromine or iodine. The term "alkylsulfonylalkyl" refers to an alkyl group substituted with a group of alkylsulfonyl (alkyl -S02), for example methylsulfonylmethyl. The term "alkylsulfinylalkyl" refers to an alkyl group substituted with a group of alkylsulfinyl (alkyl-SO), for example methylsulfinylmethyl.
The term "alkenyl" refers to an ethylenically unsaturated, straight or branched chain hydrocarbon group having 1 or 2 ethylenic bonds. The term "cycloalkenyl" refers to a cyclic aliphatic ring structure, having 1 or 2 ethylenic bonds, such as cyclopentene, cyclohexene, 1,4-cyclohexadiene, and the like. The term "haloalkenyl" refers to an alkenyl group substituted with one or more halogen groups. The term "alkynyl" refers to an unsaturated, straight or branched chain hydrocarbon group having 1 or 2 acetylenic bonds. The term "arylalkyl" is used to describe a group in which the alkyl chain may be branched or straight chain, with the aryl portion, as defined above, forming a terminal portion of the arylalkyl portion. The term "heteroarylalkyl" is used to describe a group in which the alkyl chain may be branched or straight, with the heteroaryl portion, as defined above, forming a terminal portion of the heteroarylalkyl part. The term "alkoxy" includes both branched chain and straight alkyl groups, attached to a terminal oxygen atom. Typical alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, tere. -butoxi, similar. The term "haloalkoxy" refers to an alkoxy group substituted with one or more halogen groups. The term "alkylthio" includes alkyl groups, both branched and straight chain, attached to a terminal sulfur atom. The term "haloalkylthio" refers to a group of alkylthio substituted with one or more d halogen groups.
Acceptable acids, which can form salts of the compounds of the present invention, can be selected from hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, oxalic acid, acetic acid, propionic acid, glycolic acid, methanesulfonic acid, toluenesulfonic acid, benzenesulfonic acid, (C2-C20) alkylbenzenesulfonic acid, sodium hydrogen sulfate and methyl hydrogen sulfate. Other agronomically acceptable salts can be formed as complexes of the compounds of the present invention with metal salts, such as zinc chloride or iron chloride.
A preferred embodiment of this invention relates to the compounds of the formula I, wherein: Rx is selected from H, F, Br, Cl, N02 and CN; R2 is selected from F, Cl, Br, H and CN; R3 is selected from H and CN; and alkyl (CLC ^), cycloalkyl (C3-Cß), alkenyl (C2-C12) cycloalkenyl (C3-Ca), alkynyl (C2-C12), haloalkyl (Cx- C12), haloalkenyl (C2-C12), haloalkynyl (C2-C12), alkoxy (C1-C12), alkyl [C.sup.-C12) thio, alkyl [Cx-C12) sulfonylalkyl [Cx-C12), alkyl (C1-C12) sulfinylalkyl (C1-C12), alkyl (Cx-C12) sulfonyl-cycloalkyl (C3-C8), alkyl (CLC- ^) sulfinylalkyl (C3-C8), cyanoalkoxy (Cx-C12), cyanoalkyl [C-. - C12), cyanocycloalkyl (C3-Ca), haloalkoxy (CLC ^), haloalkyl (C1-C12) thio, halocycloalkyl (C3-C8), aryl, heteroaryl, arylalkyl (Cx-C12) and hetroarylalkyl (C2-C12), all of which can be further substituted with one to three substituents, independently selected from: bromine, chlorine, fluorine, alkyl (C ^^ - C ^), cycloalkyl (C3-C8), alkenyl (C2-C12), cycloalkenyl ( C3-C8), alkynyl (C2-C12), haloalkyl (C1-C12), haloalkenyl (C2-C12),
Haloalkynyl (C2-C12), alkoxy (CLC ^), alkyl (Cx-C12) thio, alkyl (Oj-C- ^) sulfonyl, alkyl (C ^ C12) sulfinyl, phenyl, phenalkyl (Cx-C12), fenalkenyl (C2-C12), phenalkynyl (C2-C12), cyano, haloalkoxy (C1-C12), 1,3-dioxalan-2-yl and nitro; 15 R4 and Rs are each independently selected from H, halogen and CN; and (C1-C12) alkyl, (C3-Cs) cycloalkyl, (Cx-C12) haloalkyl, (Cx-C12) alkoxy, (CX-C12) alkyl, C1-C12 alkyl) sulfonylalkyl (CLC ^), alkyl (C1-C12) sulfinylalkyl (C1-C12), alkyl (Cx- 20 C12) sulfonylcycloalkyl (C3-C8), alkyl (Cx- C12) sulfinylcycloalkyl (C3-Ca), cyanoalkoxy (CL- C12), cyanoalkyl (C ^) C ^), cyanocycloalkyl (C3-C8), haloalkoxy (Cj_-C12), haloalkyl (Cx-C12) thio, halocycloalkyl (C3-Ca), C02R6, CONHR6, CON (alkyl (Cx-C12)) R6, ORs, SR6, S02Rs,? (alkyl (C 1 -C 7)) R 6, S 0 2 N ((C 1 -C 4) alkyl) R 6, aryl, heteroaryl, arylalkyl (C 2 C 4), and heteroarylalkyl (C 2 -C 12), all of which may be subsequently substituted all of which can be further substituted with one to three substituents, selected
independently of: bromine, chlorine, fluorine, alkyl (C ^ -C ^), cycloalkyl (C3-C8), alkenyl (C2-C12), cycloalkenyl (C3-C8), alkynyl (C2-C12), haloalkyl (C1 -Ci2), haloalkenyl (C2-C12), haloalkynyl (C2-C12), alkoxy (CLC ^), alkyl [C-15C12) thio, alkyl sulfonyl, alkyl [Cx- C12) sulfinyl, phenyl, phenalkyl (C1-) C12), phenalkenyl (C2-C12), phenalkynyl (C2-C12), cyano, haloalkoxy (CJ ^ -CJ ^ J), 1,3-dioxalan-2-yl and nitro; R- is selected from H, (C1-C12) alkyl, alkyl [C-. - C12) sulphonylalkyl (C1-C12) alkyl, [C1-C12 alkyl] sulfinylalkyl [C1-C12), [C-C12) alkyl sulfonylcycloalkyl (C3-C8), alkyl [C- C12) sulfinylcycloalkyl (C3-C8) , cyanoalkoxy (d-Cu), cyanoalkyl (Cj ^ -C ^), cyanocycloalkyl (C3-C8), haloalkoxy (C1-C12), haloalkyl (CLC ^) thio, halocycloalkyl (C3-C8) aryl and arylalkyl (CL-) ^); R7 is selected from H, alkyl (Cj ^ -C ^), cycloalkyl (C3-C8), haloalkyl (Cx-C12), alkyl (C ^ C ^) sulfonyl-alkyl (dC ^), alkyl (C1-C12) sulfinylalkyl (Cx-C12), alkyl ^ -C ^) sulfonylcycloalkyl (C3-C8), alkyl (C1-C12) sulfinylcycloalkyl (C3-C8), cyano-alkoxy [C12-C12), cyanoalkyl, cyanocycloalkyl (C3) -C8) haloalkoxy (CLC ^), haloalkyl [C .. - C12) thio, halo (C3 - C8) haloC0R8; R8 is selected from (C1-C12) alkyl, (C3-C8) cycloalkyl, (C3-C8) cycloalkenyl (C1-C12) haloalkyl, (CX-C12) alkylsulfonylalkyl (CLC ^), (CX-C12) alkyl sulfinylalkyl (dC ^), alkyl (Cx-C12) sulfonylcycloalkyl (C3-Ca), alkyl (C __-C12) sulfinylcycloalkyl (C3-Ca), cyanoalkoxy (Cj ^ -C ^). cyanoalkyl (C-L-C ^), cyanocycloalkyl (C3-C8), haloalkoxy thio, halocycloalkyl (C3-C8) aryl and arylalkyl (CÍ-C ^);
Rg is selected from H, (C1-C12) alkyl, alkenyl (Cx-C12), cycloalkyl (C3-C8), haloalkyl (dC ^), alkyl (Cx- C12) sulfonylalkyl (Cx-C12), alkyl (C1-C12) sulfinyl- (Cx-C12) alkyl, (Cx-C12) alkylsulfonyl-cycloalkyl (C3-C8), alkyl (Cj ^ -C ^) sulfinyl-cycloalkyl (C3-C8), cyanoalkoxy (Cx-C12), cyanoalkyl (C1-C12), cyanocycloalkyl (C3-C8), haloalkoxy (Cj ^ -Cx), haloalkyl (Cx-C12) thio halocycloalkyl (C3-C8); R10 is selected from H, chloro, NH2, alkyl, haloalkyl (C1-C12), CN, alkyl [C-. -C12) sulfonyl-alkyl (C ^^ - C ^), alkyl (Cj.-C ^) sulfinylalkyl (Cx- C12), alkyl (Cx-C12) sulfonylcycloalkyl (C3-C8), alkyl (Cj ^ -C ^ sulfinylcycloalkyl (C3-C8), haloalkyl, cyano (C1-C12) alkoxy, cyano (CX-C12) alkyl. cyanocycloalkyl (C3-C3) haloalkoxy (Cx-C12) haloalkyl (Cx-C12) thio, halocycloalkyl (C3-C8), C02- (C? -C12) alkyl, CONH-alkyl; WITH ((C 1 -C 4) alkyl), CH 2 CN, CH 2 = CH 2, CH 2 C = CH, CH 2 CO 2 -alkyl (C 2 C 4), CH 2 OCH 3, CH 1 -1,2 2,4-triazole; R1X is selected from H, CN, alkyl (Cx-C12), haloalkyl (Cx-C12) and C02-alkyl;
R12 is selected from H, (C1-C12) alkyl, C02R6, CON (CX-C12 alkyl) R6, 0R6 SR6, S02R6 > SOj? f alkyl iCi-Cj.;,)) and
N ((C 1 -C 4) alkyl R 13: R 13 is H, (C x C 12) alkyl, aryl or aryl (C x -C 12), A is N or CH, B is N or CR 10, Z is O, CH (R 3) ), CO, CS, C0NR12 ÓCSNR12; X is selected from O, S;? R12, C02, OCH (R6) C02, SCH (R6) C02,
CH = C (C1) C02, CH2CH (C1) C02, CONH, OCH (R6) CONH, SCH (R6) CONH, CH = C (Cl) CONH and CH2CH (Cl) CONH, when Z is CH (R3); X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (Cl) CO CH2CH (halo) CO, when Z is 0; X is selected from O, S, CO, OCH (R6), CH = C (C1), CH2CH (C1), CONH, OCH (R5) CONH, SCH (R6) CONH,
CH = (Cl) CONH, CH2CH (C1) C0NH and NR12, when Z is
CO, CS, CONR12 or CSNR12; and Q is selected from NR7COR8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8,
Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Ql6, where or their agronomically acceptable salts.
A more preferred embodiment of this invention relates to compounds of the formula I, wherein: Rj is H, F, or Cl; R2 is Cl; R3 is selected from H, bromo, chloro, fluoro, alkyl (C ^ Cg), cycloalkyl (C3-C6), alkenyl (C2-C6) cycloalkenyl (C3-C8), alkynyl (C2-C6), haloalkyl [C- C6), haloalkenyl (C2-C6), haloalkynyl (C2-C6), alkoxy (Cj ^ -8), alkyl (C1-C6) thio, aryl, heteroaryl, arylalkyl (C__-Cx2) and hetroarylalkyl (C2-C12) , wherein the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene, and triazole, and this aryl and heteroaryl group can be further substituted with one to three substituents, independently selected from: bromine, chlorine, fluorine, (Cx-C12) alkyl, (C3-C8) cycloalkyl, (C2-C12) alkenyl, (C3-Ca) cycloalkenyl, (C2-C12) alkynyl, [C .. -C12] haloalkyl, haloalkenyl ( C2-C12), haloalkynyl (C2-C12), alkoxy (Cx-C12), alkyl (Cx-C12) thio, alkyl (Cx-Cx2) sulfonyl, alkyl (Cx- C12) sulfinyl, phenyl, phenalkyl (Cx-C12) ), fenalkenyl (C2-CX2), phenalkynyl (C2-C12), cyano, haloalkoxy (Cx-C12), 1,3-dioxalan-2-yl and nitro; R4 and R5 are each independently selected from H, bromo, chloro, fluoro, CN; and (Cx-C6) alkyl, 5 (C5-C6) cycloalkyl, (Cx-C6) haloalkyl, (Cx-C6) alkoxy, (Ci-Cg) alkyl, C02R6, CONHRβ, CON (CX-C12 alkyl) ) R6, 0R6, SR6, S02R6, NHR6, N (alkyl (CX-CX2)) R6, S02N (alkyl (CX-CX2)) R6, aryl, heteroaryl, arylalkyl (Cx-C12), and
Heteroarylalkyl (C2-C12), where the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, these aryl and heteroaryl groups can be further substituted with one to three
substituents, independently selected from: bromine, chlorine, fluorine, alkyl (CX-CX2), cycloalkyl (C3-C8), alkenyl (C2-CX2), cycloalkenyl (C3-C8), alkynyl (C2-C12), haloalkyl ( Cx-C12), haloalkenyl (C2-C12), haloalkynyl (C2-C12),
Alkoxy (CX-CX2), alkyl (Cx-C12) thio, alkyl (Cx-C12) sulfonyl, alkyl (Cx-C12) sulfinyl, phenyl, phenalkyl (Cx-C12), fenalkenyl (C2-CX2), phenalkynyl ( C2-CX2), cyano, haloalkoxy (Cx-C12), 1,3-dioxalan-2-yl and nitro; R6 is selected from H, alkyl (Cx-C12), aryl and arylalkyl (Cx-C6), where the aryl group is naphthyl or phenyl; R7 is selected from H, alkyl (Cx-C12), cycloalkyl (C3-C8), haloalkyl (Cx-Cx2), and C0R6; R8 is selected from alkyl (Cx-C12), cycloalkyl (C3-C8), cycloalkenyl (C3-C8) haloalkyl (CX-CX2), aryl arylalkyl (Cx-C6); R9 is selected from H, alkyl (Cx-C6), alkenyl (Cx-C12), alkenyl (C2-C6) cycloalkyl (C3-C8), cycloalkyl (C5-C6), haloalkyl (CX-CX2), haloalkyl (Cx) -C6); Rxo is selected from H, chloro, NH2, alkyl (Cx-C6), haloalkyl (Cx-C12), haloalkyl (Cx-C6), C ?, C02- alkyl (Cx-Cxz), CONH-alkyl (CX-CX2) ), CO? - (alkyl (Cx-C6) 2, CH2C ?, CH2CH = CH2, CH2G = CH2, CH2C02- (Cx-C12) alkyl CH2OCH3, CH-1, 2,4-triazole; RX1 is selected from H , CN, alkyl (Cx-C3), haloalkyl (Cx-C12), haloalkyl (Cx-C6) and C02-alkyl (Cx-C12); RX2 is selected from H, alkyl (Cx-C8), C02R6, CON ( alkyl (Cx-C8)) R6, OR6 SRg, S02R6? S02N ((CX-C8) alkyl) N (CX-C8 alkyl) RX3;
R13 is H, alkyl (Cx-Ca), aryl or aryl (Cx-C6), where the aryl group is naphthyl or phenyl; A is N or CH; B is N or CRX0; Z is O, CH (R3), CO, CS, C0NRx2 or CSNR12; X is selected from O, S, C02, 0CH (R6) C02, SCH (R6) C02,
CH = C (C1) C02, CH2CH (C1) C02, CONH, OCH (R6) CO? H,
SCH (R6) CONH, CH = C (C1) C0? H and CH2CH (Cl) CONH, when Z is CH (R3), -X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (C1) C0 and
CH2CH (halo) CO, when Z is O; X is selected from O, S, CO, 0CH (R6), CH = C (C1),
CH2CH (C1), CO? H, OCH (R5) CONH, SCH (R6) CONH,
CH = (Cl) CONH, CHaCHÍCDCO? H and NR12, when Z is CO, CS, CONR12 or CSNRX2; and Q is selected from? R7COR8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8,
Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16, where or their agronomically acceptable salts, selected from those formed of hydrochloric acid, sulfuric acid, acetic acid, propionic acid, phosphoric acid and oxalic acid.
An even more preferred embodiment of this invention relates to the compounds of the formula I, in which
Rx is H, F or Cl; R2 is Cl; R3 is selected from H, bromine, chlorine, fluorine, alkyl (Cx-C6), cycloalkyl (C3-C £), alkenyl (C2-C6) cycloalkenyl (C3-C8), alkynyl (C2-C6), haloalkyl (Cx) - C6), haloalkenyl (C2-C6), haloalkynyl (C2-C6), haloalkynyl (C2-C6), alkoxy (Cx-C6), alkyl (CX-C6) thio, 3-furyl, 4-chloro-2- furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2, 5-dichloeo-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyano-phenyl, 3- (1,3-dioxolan-2-yl) phenyl, 2-fluorophenyl , 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3, 5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-chloro-phenyl, 3,4-difluorophenyl, 3-fluoro -5- trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo -3- pyridyl, 5, 6- dichloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl- 4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-dichloro-4-pyridyl, 2- thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-10-chloro-3-thienyl and 2,5-dichloro-3-thienyl; R4 and R5 are each independently selected from H, bromo, chloro, fluoro, CN; and (Cx-C6) alkyl, (C5-C6) cycloalkyl, (C1-C6) haloalkyl, (CX-C6) alkoxy, alkyl (C-C, thio, C02R6, CONHR6,
CON (alkyl (Cx-C6)) R6, OR6, SR6, S02R6, NHR6, 3- furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5-chloro-3-furyl, 2, 5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4- 20 trifluoromethylphenyl, 4-bromo-phenyl, chlorophenyl, -fluorophenyl, trifluoromethoxyphenyl, 4-cyano-phenyl, 3- (1,3-dioxolan-2-yl) phenyl, 2-fluorophenyl, chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4- difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-5-chloro-phenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl , 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl , 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, -methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4 - pyridyl, 2,6-dichloro-4-pyridyl, 2-thienyl, 3-15-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2.5- dichloro-3-thienyl; R6 is selected from H, (Cx-C3) alkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethyl, fluoromethylphenyl, -bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyano-phenyl, 3- (1, 3-dioxolan-2-yl) phenyl, 2-fluoro-
R9 is selected from H, alkyl (Cx-C6), alkenyl (CX-CX2), cycloalkyl (C5-C6) and haloalkyl (Cx-C6); Rx0 is selected from H, chloro, NH2, alkyl (Cx-C6), haloalkyl (Cx-C6), CN, C02-alkyl (Cx-C6), CO? H- alkyl (Cx-C6), CON- (alkyl) (Cx-C6) 2, CH2C ?,
CH2CH = CH2, CH2C = CH2, CH2C02-alkyl (CX-CX2) CH2OCH3,
CH-1, 2,4-triazole; Rxx is selected from H, CN, alkyl (Cx-C6), haloalkyl (Cx-C6) and C02-alkyl (CX-CX2); RX2 is selected from H, alkyl (Cx-C8), C02-alkyl (Cx-C6),
CON (alkyl (Cx-Cg)) 2, O-alkyl (Cx-C6), S-alkyl (Cx-C6), S02- (Cx-C6), S02N- (alkyl (Cx-C6)) 2 and
N ((Cx-C6) alkyl 2. R13 is H, (Cx-C6) alkyl, aryl or aryl (Cx-C4), where the aryl group is naphthyl or phenyl, A is N or CH, B is N or CRX0; Z is O, CH (R3), CO, CS, C0NR12 or CSNR12; X is selected from 0, S, C02, 0CH (R6) C02, SCH (R6) C02, CH = C (C1) C02, CH2CH (C1) C02, CONH, OCH (R6) CONH,
SCH (R6) CONH, CH = C (C1) C0NH and CH2CH (Cl) CONH, when Z is CH (R3);
29
X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (Cl) CO and
CH2CH (Cl) CO, when Z is O; X is selected from O, S, CO, OCH (R6), CH = C (C1),
CH2CH (C1), CONH, OCH (Rs) CONH, SCH (R6) CONH, CH = (Cl) CONH, CH2CH (Cl) CONH and NR12, when Z is
CO, CS, CONRx2 OR CS? R12; "and Q is selected from NR7COR8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8,
Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16; or its agronomically acceptable salts, selected from those formed of hydrochloric acid, acetic acid, propionic acid, and oxalic acid.
A second aspect of the invention relates to herbicidal compositions comprising a compound of the formula I and an agronomically acceptable carrier. A third aspect of this invention relates to a method for controlling weeds, which comprises applying a herbicidally effective amount of a composition comprising a compound of the formula I and an agronomically acceptable weed carrier to the site of these weeds herbs, or the means of growing them.
The following examples of the compounds of the formula I are presented in Tables 1 to 25 and are representative of the invention. In these tables, the abbreviation "Ph" is used to mean phenyl, "Ph-4-Cl" is used to mean 4-chlorophenyl, "Ph-4-F" is used to mean 4-fluorophenyl, "CHjPh "is used to mean benzyl," CH2Ph-4-Cl "is used to mean 4-chlorobenzyl," 3-Py "means 3 -pyridyl," Me "means methyl, and" Et "means ethyl.
31
Table 1
No R1 R2 R »R. Rs
1 F Cl CO2 H H H
2 F C! CO2 CH3 H H
3 F Cl CO2 C2H5 H H
4 F Cl CO2 C3H7 H H
F Cl C02 H CH3 CH3
6 F Cl CO2 CH3 Ph CH3
7 F Cl CO2 C2H5 Ph-4-CI H
8 F Cl CO2 H H SCH3
9 F Cl CO2 CN H H
F Cl CO2 Ph H H
11 F Cl CO2 CH2Ph H H
12 F Cl CO2 Ph-4-CI H H
13 F Cl CO2 CH2Ph-4-CI H H
14 F Cl CO2 3-Py H H
F Cl OCH2CO2 H H H
16 F Cl OCH2C02 CH3 H H
17 F Cl OCH2CO2 C2H5 H H
18 F Cl OCH2CO2 C3H7 H H
19 F Cl OCH2C02 H CH3 CH3
F Cl OCH2CO2 CH3 Ph CH3
21 F Cl OCH2C02 C2H5 Ph-4-CI H
22 F Cl OCH2C02 H H SCH3
23 F Cl OCH2C02 CN H H
24 F Cl OCH2C02 Ph H H
F Cl OCH2C02 CH2Ph H H
26 F Cl OCH2CO2 Ph-4-CI H H
27 F Cl 0CH2C02 CH2Ph-4-CI H H
28 F Cl OCH2C02 3-Py H H 9 F Cl OCH (CH 3) CO 2 H H H O F Cl OCH (CH 3) CO 2 CH 3 H 1 F Cl OCH (CH 3) CO 2 C 2 H 5 H 32 32 F Cl OCH (CH 3) CO 2 C 3 H 7 H H
33 F Cl OCH (CH3) CO2 H CH3 CH3
34 F Cl OCH (CH3) CO2 CH3 Ph CH3
F Cl CH = C (CI) C02 H H H
36 F Cl CH2CH (CI) CO2 H H H
37 F Cl OCH (CH3) CO2 CN H H
38 F Cl OCH (CH3) CO2 Ph H H
39 F Cl OCH (CH3) CO2 CH2Ph H H
40 F Cl OCH (CH3) C02 Ph-4-CI H H
41 F Cl OCH (CH3) CO2, CH2Ph-4-CI H H
42 F Cl OCH (CH3) CO2 3-Py H H
43 F Cl 0 H H H
44 F Cl O - CH3 H H
45 F Cl O C2H5 H H
46 F Cl O C3H7 H H
47 F Cl O H CH3 CH3
48 F C! O CH3 Ph CH3
49 F Cl O C2HS Ph-4-CI H
50 F Cl O H H SCH3
51 F Cl O CN H H
52 F Cl O Ph H H
53 F Cl 0 CH2Ph H H
54 F Cl O Ph-4-CI H H
55 F Cl O CH2Ph-4-CI H H
56 F Cl 0 3-Py H H
57 F Cl SCH2C02 H H H
58 F Cl SCH2CO2 CH3 H H
59 F Cl SCH2CO2 C2H5 H H
60 F Cl SCH2CO2 C3H7 H H
61 F Cl SCH2C02 H CH3 CH3
62 F Cl SCH2CO2 CH3 Ph CH3
63 F Cl SCH2CO2 C2H5 Ph-4-CI H
64 F Cl SCH2CO2 H H SCH3
65 F Cl SCH2C02 CN H H
66 F Cl SCH2CO2 Ph H H
67 F Cl SCH2CO2 CH2Ph H H
68 F Cl SCH2C02 Ph-4-CI H H
69 F Cl SCH2C02 CH2Ph-4-CI H H
70 F Cl SCH2CO2 3-Py H H
71 F H SCH (CH3) CO2 H H H
72 F Cl SCH (CH3) CO2 CH3 H H
73 F Cl SCH (CH3) CO2 C2H5 H H
74 F Cl SCH (CH3) C02 C3H7 H H
75 F Cl SCH (CH3) CO2 H CH3 CH3
76 F Cl SCH (CH3) C02 CH3 Ph CH3 33
77 F Cl SCH (CH3) C02 C2H5 Ph-4-CI H
78 F Cl SCH (CH3) CO2 H H SCH
79 F Cl SCH (CH3) CO2 CN H H
80 F C! SCH (CH3) CO2 Ph H H
81 F Cl SCh (CH3) CO2 CH2Ph H H
82 F Cl SCH (CH3) CO2 Ph-4-CI H H
83 F Cl SCH (CH3) CO2 CH2Ph-4-CI H H
84 F Cl SCH (CH3) CO2 3-Py H H
85 F Cl S H H H
86 F Cl S CH3 H H
87 F Cl S C2H5 H H
88 F Cl S - C3H7 H H
89 F Cl S. H CH3 CH3
90 F Cl S CH3 Ph CH3
91 F Cl S C2H5 Ph-4-CI H
92 F Cl S H SCH.
93 F Cl s CN H H
94 F Cl s Ph H H
95 F Cl s CH2Ph H H
96 F Cl s Ph-4-CI H H
97 F Cls CH2Ph-4-Cl H H
98 F Cl s 3-Py H H
99 F Cl CH = C (CI) CO2 CN H H
100 F Cl CH2CH (CI) CO2 CN H H
101 F Cl CH = C (CI) CO2 CH3 H H
102 F Cl CH2CH (CI) C02 CH3 H H
103 Cl Cl O H H H
104 Cl Cl OCH2CO2 H H H
105 Cl Cl OCH (CH3) CO2 H H H
106 Cl Cl CH = C (CI) CO2 H H H
107 Cl Cl CH2CH (CI) C02 H H H
108 Cl Cl CH2CH (CI) CO2 CH3 H H
109 Cl Cl SCH2CO2 H H H
110 Cl Cl SCH (CH3) C02 H H H
111 Cl Cl CO2 H H H
112 H Cl O H H H
113 H Cl OCH2CO2 H H H
114 H Cl OCH (CH3) C02 H H H
115 H Cl CH = C (CI) C02 H H H
116 H Cl CH2CH (CI) CO2 H H H
117 H Cl S H H H
118 H Cl SCH2CO2 H H H
119 H Cl SCH (CH3) CO2 H H H
120 H Cl CH = C (CI) C02 H H H 34 I 35
154 F Cl OCH (CH3) CO2 CH3 H H H
155 F Cl OCH (CH3) CO2 C2H5 H H H
156 F Cl OCH (CH3) CO2 H C! Cl CO2CH3
157 F Cl OCH (CH3) CO2 H CH3 CH3 H
158 F Cl OCH (CH3) CO2 CH3 Ph CH3 H
159 F Cl OCH (CH3) C02 C2H5 Ph-4-CI H H
160 F Cl OCH (CH3) CO2 H C2H5 CO2Et H
162 F Cl OCH (CH3) CO2 Ph H H H
163 F Cl OCH (CH3) CO2 CH2Ph H H H
164 F Cl OCH (CH3) CO2 Ph-4-CI H H H
165 F Cl OCH (CH3) C02 CH2Ph-4-CI H H H
166 F Cl OCH (CH3) CO2 3-Py H H H
167 F Cl O H H H H
168 F Cl 0 CH3 H H H
169 F Cl O C2H5 H H H
170 F Cl O H Cl Cl CO2CH3
171 F Cl O H CH3 CH3 H
172 F Cl O CH3 Ph CH3 H
173 F Cl O C2H5 Ph-4-Cl H H
174 F Cl 0 -H C2H5 C02Et H
175 F Cl O CN H H H
176 F Cl 0 Ph H H H
177 F Cl O CH2Ph H H H
178 F Cl O Ph-4-CI H H H
179 F Cl O CH2Ph-4-CI H H H 180 F Ci O 3-Py H H H 181 F Cl SCH2C02 H H H H 182 F Cl SCH2CO2 CH3 H H H 183 F Cl SCH2CO2 C2H5 H H H 184 F Cl SCH2C02 H Cl Cl CO2CH3
185 F Cl SCH2CO2 H CH3 CH3 H 186 F Cl SCH2C02 CH, Ph CH3 H 187 F Cl SCH2CO2 C2H5 Ph-4-CI HH 188 F Cl SCH2C02 H C2H5 C02Et H 189 F Cl SCH2CO2 CN HHH 190 F Cl SCH2C02 Ph HHH 191 F Cl SCH2CO2 CH2Ph HHH 192 F Cl SCH2CO2 Ph-4-CI HHH 193 F Cl SCH2C02 CH2Ph-4-CI HHH 194 F Cl SCH2CO2 3-Py HHH 195 F Cl SCH (CH3) C02 HHHH 196 FC! SCH (CH3) C02 CH3 H H H 197 F C! SCH (CH3) CO2 C2H5 H H H 198 F Cl SCH (CH3) C02 H Cl Cl C02CH3 36
199 F Cl SCH (CH3) C02 H CH3 CH3 H
200 F Cl SCH (CH3) CO2 CH3 Ph CH3 H
201 F Cl SCH (CH3) CO2 C2H5 Ph-4-CI H H
202 F Cl SCH (CH3) C02 H C2H5 C02EH H
203 F Cl SCH (CH3) CO2 CN H H H
204 F Cl SCH (CH3) CO2 Ph H H H
205 F Cl SCH (CH3) CO2 CH2Ph H H H
206 F Cl SCH (CH3) CO2 Ph-4-Cl H H H
207 F Cl SCH (CH3) C02 CH2Ph-4-CI H H H
208 F C! SCH (CH3) CO2 3-Py H H H
209 F Cl s H H H H
210 F Cl s CH3 H H H
211 F Cls C2H5 H H H
212 F Cl s H Cl Cl CO2CH3
213 F Cl s H CH3 CH3 H
214 F Cl s CH3 Ph CH3 H
215 F Cls C2H5 Ph-4-CI H H
216 F Cl s H C2H5 C02Et H
217 F Cl s CN H H H
218 F Cl s Ph H H H
219 F Cl s CH2Ph H H H
220 F Cl s Ph-4-CI H H H
221 F Cl s CH2Ph-4-CI H H H
222 F Cl s 3-Py H H H
223 F Cl CH = C (CI) CO2 H H H H
224 F Cl CH2CH (CI) C02 H H H H
225 Cl Cl O H H H H
226 Cl Cl OCH2C02 H H H H
227 Cl Cl S H H H H
228 Cl Cl SCH2CO2 H H H H
229 Cl Cl SCH (CH3) C02 H H H H
230 Cl Cl CO2 H H H H
231 H Cl O H H H H
232 H Cl OCH2CO2 H H H H
233 H Cl S H H H H
234 H Cl SCH2C02 H H H H
235 H Cl CO2 H H H H 37
TalD l a 3
where A = CH, B = N and Q = Q1 in a compound of the formula I
No R, R2 X R3 R4 R5 236 F Cl C02 HHH 237 F Cl CO2 CH3 HH 238 F Cl CO2 C2H5 HH 239 F Cl CO2 H Cl Cl 240 F Cl CO2 H CH3 CH3 241 F Cl CO2 CH3 Ph CH3 242 F Cl CO2 C2H5 Ph-4-CI H 243 FC! CO2 H Ph-4-CI CH3 244 F C! C02 CN HH 245 F Cl CO2 Ph HH 246 F Cl C02 CH2Ph HH 247 F Cl CO2 Ph-4-CI HH 248 F Cl C02 CH2Ph-4-CI HH 249 F Cl CO2 3-Py HH 250 F Cl OCH2CO2 HHH 251 F Cl OCH2C02 CH3 HH 252 F Cl OCH2CO2 C2H5 HH253 F Cl OCH2C02 Cl Cl Cl 254 Cl Cl OCH2CO2 H CH3 CH3 255 F Cl OCH2CO2 CH3 Ph CH3 256 F Cl OCH2CO2 C2H5 Ph-4-CI H 257 F Cl OCH2CO2 H Ph-4 -CI CH3 258 F Cl OCH2CO2 CN HH 259 F Cl OCH2CO2 Ph HH 260 F Cl OCH2CO2 CH2Ph HH 261 F Cl OCH2CO2 Ph-4-CI HH 262 F Cl OCH2CO2 CH2Ph-4-CI HH 263 F Cl OCH2CO2 3-Py HH 264 F Cl OCH (CH3) CO2 HHH 265 F Cl OCH (CH3) CO2 CH3 HH 266 F Cl OCH (CH3) CO2 C2H5 HH 267 F Cl OCH (CH3) CO2 H Cl Cl 268 F Cl OCH (CH3) CO2 H CH3 CH3 269 F Cl OCH (CH3) CO2 CH3 Ph CH3 38 270 F Cl OCH (CH3) CO2 C2H5 Ph-4-Ci H
271 F Cl OCH (CH3) CO2 H Ph-4-CI CH3
272 F Cl OCH (CH3) CO2 CN H H
273 F Cl OCH (CH3) CO2 Ph H H
274 F Cl OCH (CH3) CO2 CH2Ph H H
275 F Cl OCH (CH3) CO2 Ph-4-CI H H
276 F Cl OCH (CH3) CO2 CH2Ph-4-CI H H
277 F Cl OCH (CH3) CO2 3-Py H H
278 F Cl 0 H H H
279 F Cl O CH3 H H
280 F Cl O C2H5 H H
281 F Cl O H Cl Cl
282 F Cl O H CH3 CH3
283 F Cl 0 CH3 Ph CH3
284 F Cl O C2H5 Ph-4-CI H
285 F Cl O H Ph-4-CI CH3
286 F Cl O CN H H
287 F Cl O Ph H H
288 F Cl O CH2Ph H H
289 F Cl O Ph-4-CI H H
290 F Cl O CH2Ph-4-CI H H
291 F Cl 0 3-Py H H
292 F Cl SCH2CO2 H H H
293 F Cl SCH2CO2 CH3 H H
294 F Cl SCH2C02 C2H5 H H
295 F Cl SCH2C02 H Cl Cl
296 F Cl SCH2CO2 H CH3 CH3
297 F Cl SCH2CO2 CH3 Ph CH3
298 F Cl SCH2CO2 C2H5 Ph-4-CI H
299 F Cl SCH2CO2 H Ph-4-CI CH3
300 F Cl SCH2CO2 CN H H
301 F Cl SCH2CO2 Ph H H
302 F Cl SCH2CO2 CH2Ph H H
303 F Cl SCH2C02 Ph-4-CI H H
304 F Cl SCH2CO2 CH2Ph-4-CI HH 05 F Cl SCH2CO2 3-Py HH 06 F Cl SCH (CH3) CO2 HHH 07 F Cl SCH (CH3) CO2 CH3 HH 08 F Cl SCH (CH3) CO2 C2H5 HH 09 F Cl SCH (CH3) CO2 H Cl Cl 10 F Cl SCH (CH3) CO2 H CH3 CH3 11 F Cl SCH (CH3) C02 CH3 Ph CH3 12 F Cl SCH (CH3) CO2 C2H5 Ph-4-CI H 13 F Cl SCH ( CH3) CO2 H Ph-4-CI CH3 39 314 F Cl SCH (CH3) CO2 CN HH 315 F Cl SCH (CH3) CO2 Ph HH 316 F Cl SHHH 317 F Cl S CH3 HH 318 F Cl S C2H5 HH 319 F Cl SH Cl Cl 320 F Cl SH CH 3 CH 3 321 F Cl S CH 3 Ph CH 3 322 F Cl S C 2 H 5 Ph-4-CI H 323 F Cl CH = C (CI) CO 2 HHH 324 F Cl CH 2 CH (CI) CO 2 HHH 325 F Cl s Ph HH 326 F Cl s CH2Ph CH3 CH3 327 F Cl s Ph-4-CI HH 328 Cl Cl OHHH 329 Cl Cl OCH2C02 HHH 330 Cl Cl H HH 331 Cl Cl SCH2CO2 HHH 332 Cl Cl SCH (CH3) CO2 HHH 333 Cl Cl CO2 HHH 334 HC! O H H H 335 H Cl OCH 2 CO 2 H H H 336 H Cl S H H H 337 H Cl SCH 2 CO 2 H H H 338 H Cl C02 H H H
T a b l a 4 formula I 344 F Cl CO2 Ph-4-CI 40 345 F Cl CO2 CN 346 F Cl C02 3-Py
347 F Cl OCH2C02 H 348 F Cl OCH2CO2 CH3
349 F Cl OCH2C02 C2H5
350 F Cl OCH2CO2 Ph 351 F Cl OCH2CO2 CH2Ph
352 F Cl OCH2CO2 Ph-4-CI
353 F Cl OCH2CO2 CN 354 F Cl OCH2CO2 3-Py
355 F Cl OCH (CH3) CO2 H 356 F Cl OCH (CH3) CO2 CH3
357 F Cl OCH (CH3) C02 C2H5
358 F Cl OCH (CH3) CO2 Ph 359 F Cl OCH (CH3) CO2 CH2Ph
360 F Cl OCH (CH3) CO2 Ph-4-CI
361 F Cl CH = C (CI) CO2 H 362 F Cl CH2CH (CI) CO2 H 363 F Cl 0 H 364 F Cl O CH3
365 F Cl 0 C2H5
366 F Cl O Ph 367 F Cl O CH2Ph
368 F Cl CH = C (CI) CO2 CN 369 F Cl CH2CH (CI) CO2 CN 370 F Cl 0 3-Py
371 F Cl SCH2CO2 H 372 F Cl SCH2CO2 CH3
373 F Cl SCH2C02 C2H5
374 F C! SCH2CO2 Ph 375 F Cl SCH2CO2 CH2Ph
376 F Cl SCH2CO2 Ph-4-CI
377 F Cl SCH2C02 CN 378 F Cl SCH2CO2 3-Py
379 F H SCH (CH3) C02 H 380 F Cl SCH (CH3) C02 CH3 381 F Cl SCH (CH3) CO2 C2H5
382 F Cl SCH (CH3) C02 Ph 383 F Cl SCH (CH3) CO2 CH2Ph
384 F Cl SCH (CH3) C02 Ph-4-CI
385 F Cl SCH (CH3) CO2 CH2Ph-4-CI
386 F Cl SCH (CH3) CO2 3-Py
387 F Cl SH 388 F Cl S CH3 41 389 F Cl s C2H5 390 F Cl s Ph 391 F Cl s CH2Ph 392 F Cl s Ph-4-CI 393 F Cl s CH2Ph-4-CI 394 F Cl s 3-Py 395 C! Cl 0 H 396 Cl Cl OCH 2 CO 2 H 10 397 Cl Cl OCH (CH 3) C 0 2 H 398 Cl Cl CH = C (CI) CO 2 H 399 Cl Cl CH 2 CH (CI) CO 2 H 400 Cl Cl H 15 40 Cl Cl SCH 2 CO 2 H 402 Cl Cl SCH (CH 3) C 0 2 H 403 Cl Cl H 2 H 404 H Cl OH 20 405 H Cl OCH 2 CO 2 H 406 H Cl OCH (CH 3) CO 2 H 407 H Cl CH = C (CI) CO 2 H 408 H Cl CH 2 CH (CI) CO2 H? ? 409 H Cl S H 410 H Cl SCH2CO2 H 411 H Cl SCH (CH3) CO2 H 412 H Cl CH = C (CI) CO2 H 30 413 H C! CH2CH (CI) CO 2 H 414 H Cl CO 2 H 415 F Cl OCH 2 CO 2 Ph-4-F 416 F Cl SCH 2 CO 2 Ph-4-F 5 Ta b l a 5
this "of the" formula I
No X R3 0 417 F Cl CO2 H 418 F Cl co, CH, 42
453 F Cl SCH2C02 CH2Ph 454 F Cl SCH2C02 Ph-4-CI 455 F Cl SCH2CO2 CH2Ph-4-CI
45 456 F Cl SCH2CO2 3-Py 457 F Cl SCH (CH3) C02 H 458 F Cl SCH (CH3) CO2 CH3 459 F Cl SCH (CH3) C02 C2H5 50 460 F Cl SCH (CH3) CO2 Ph 461 F C! SCH (CH3) CO2 CH2Ph 43
462 F Cl SCH (CH3) C02 Ph-4-CI 463 F Cl SCH (CH3) CO2 CH2Ph-4-CI 464 F Cl SCH (CH3) C02 3-Py 465 F Cl S H 466 F C! s CH3 467 F Cls C2H5 468 F Cls Ph 469 F C i s CH2Ph 470 F Cl s Ph-4-CI 471 F Cl s CH2Ph-4-CI 472 F Cl s 3-Py 473 Cl Cl 0 H 474 Cl Cl OCH2CO2 H 475 Cl Cl s H 476 C! Cl SCH2CO2 H 477 Cl Cl SCH (CH3) C02 H 478 Cl Cl C H 479 H Cl O H 480 H Cl OCH 2 CO 2 H 481 H Cl S H 482 H Cl SCH 2 CO 2 H 483 H Cl CO, H
Ta b l a 6
where A = CH, B = N, R4 = R5 = H, Q = Q2, in a compound of the formula I
488 F Cl CO2 CH2Ph 489 F Cl CO, Ph-4-CI 44 490 F Cl CO2 CH2Ph-4-CI
491 F Cl CO2 3-Py
492 F Cl OCH2C02 H 493 F Cl OCH2CO2 CH3
494 F Cl OCH2CO2 C2H5
495 F Cl OCH2C02 Ph 496 F Cl OCH2CO2 CH2Ph
497 F Cl OCH2C02 CN 498 F Cl OCH2C02 CH2Ph-4-CI
499 F Cl OCH2CO2 3-Py
500 F Cl, OCH (CH3) C02 H 501 F Cl OCH (CH3) CO2 CH3 502 F Cl OCH (CH3) CO2 C2H5
503 F Cl OCH (CH3) C02 Ph 504 F Cl OCH (CH3) CO2 CH2Ph
505 F Cl OCH (CH3) C02 Ph-4-CI
506 F Cl OCH (CH3) C02 CH2Ph-4-CI
507 F Cl OCH (CH3) CO2 3-Py 508 F Cl 0 H 509 F Cl O CH3 510 F Cl O C2H5
511 F Cl O Ph 512 F Cl O CH2Ph
513 F Cl O Ph-4-CI
514 F Cl O CH2Ph-4-CI
515 F Ci O 3-Py 516 F Cl SCH2C02 H 517 F Cl SCH2CO2 CH3 518 F Cl SCH2C02 C2H5
519 F Cl SCH2CO2 Ph 520 F Cl SCH2C02 CH2Ph
521 F Cl SCH2C02 Ph-4-CI
522 F Cl SCH2CO2 CH2Ph-4-CI
523 F Cl SCH2C02 3-Py 524 F Cl SCH (CH3) CO2 H 525 F Cl SCH (CH3) CO2 CH3 526 F Cl SCH (CH3) C02 C2H5 527 F Cl SCH (CH3) CO2 Ph 528 F Cl SCH (CH3) C02 CH2Ph
529 F Cl SCH (CH3) CO2 Ph-4-CI
530 F Cl SCH (CH3) CO2 CH2Ph-4-CI
531 F Cl SCH (CH3) CO2 3-Py 532 F Cl S H 533 F Cl S CH3 45
534 F Cls C2H5 535 F Cl S Ph 536 F Cl S CH2Ph 537 F Cl s Ph-4-Cl 538 F Ci s CH2Ph-4-CI 539 F Cl S 3-Py 540 Cl Cl OH 541 Cl Cl OCH2CO2 H 542 Cl Cl H 543 Cl Cl SCH2CO2 H 544 Cl Cl SCH (CH3) CO2 H 545 CI Cl CO2 H 546 H Cl OH 547 H Cl OCH2C02 H 548 H Cl s H 549 H Cl SCH2C02 H 550 H Cl CO2 H Table 7
where A = B = N, R4 = R5 = H, Q = 3, in a compound of formula I
No R, XR, 551 F Cl co2 H 552 F Cl CO2 CH3 553 F Cl CO2 C2H5 554 F Cl CO2 Ph 555 F Cl co2 CH2Ph 556 F Cl CO2 Ph-4-CI 557 F Cl C02 CN 558 F Cl CO2 3- Py 559 F Cl OCH2C02 H 560 F Cl OCH2CO2 CH3 561 F Cl OCH2CO2 C2HS 562 FC! OCH2C02 Ph 563 F Cl OCH2C02 CH2Ph 564 F Cl OCH2CO2 Ph-4-CI 565 F Cl OCH2C02 CN 46 566 F Cl OCH2CO2 3-Py
567 F Cl OCH (CH3) C02 H 568 F C! OCH (CH3) C02 CH3
569 F C! OCH (CH3) CO2 C2H5
570 F Cl OCH (CH3) C02 Ph 571 F Cl OCH (CH3) CO2 CH2Ph
572 F C! OCH (CH3) CO2 Ph-4-CI
573 F Cl OCH (CH3) CO2 CN 574 F Cl OCH (CH3) CO2 3-Py
575 F Cl O H 576 F Cl 0 CH3 577 F Cl O C2H5
578 F Cl O Ph 579 F Cl 0 CH2Ph
580 F Cl O Ph-4-CI
581 F Cl O CH2Ph-4-CI
582 F Cl O 3-Py
583 F Cl SCH2CO2 H 584 F Cl .SCH2C02 CH3 585 F Cl SCH2CO2 C2H5
586 F Cl SCH2CO2 Ph 587 F Cl SCH2CO2 CH2Ph
588 F Cl SCH2CO2 Ph-4-Cl
589 F Cl SCH2CO2 CH2Ph-4-CI
590 F Cl SCH2CO2 3-Py
591 F H SCH (CH3) CO2 H 592 F Cl SCH (CH3) C02 CH3 593 F Cl SCH (CH3) CO2 C2H5
594 F Cl SCH (CH3) CO2 Ph 595 F Cl SCH (CH3) CO2 CH2Ph
596 F C! SCH (CH3) CO2 Ph-4-CI
597 F Cl SCH (CH3) C02 CH2Ph-4-CI
598 F Cl SCH (CH3) CO2 3-Py
599 F Cl S H 600 F Cl S CH3 601 F Cl S C2H5
602 F Cl S Ph 603 F Cl S CH2Ph
604 F Cl S Ph-4-CI
605 F Cl S CH2Ph-4-CI
606 F Cl S 3-Py
607 F Cl CH = C (CI) CO2 H 608 F Cl CH2CH (CI) CO2 H 47 609 Cl Cl OH 610 Cl Cl OCH2C02 H 611 Cl Cl CH = C (CI) CO2 H 612 Cl Cl CH2CH (CI) CO2 H 613 Cl Cl SCH2C02 H 614 Cl Cl SCH (CH3) CO2 H 615 Cl Cl CO2 H 616 H Cl OCH2C02 H 617 H Cl CH = C (CI) CO2 H 618 H Cl CH2CH (CI) C02 H 619 H Cl SH 620 H Cl SCH2C02 H 621 H Cl SCH (CH3) CO2 H 622 H Cl CO2 H 623 F Cl OCH2CO2 Ph-4-F 624 F Cl SCH2CO2 Ph-4-F
Ta b l a 8
where A = ?, B = CH, R = R5 = CH3, Q = Q3, in a compound of the formula I 639 F Cl OCH2CO2 CH2Ph-4-CI 640 F Cl OCH2CO2 3-Py
m O? n or m o -o or go, cs < O CO r r m
49 Ta b l a 9 where A = CH, B = N, R4 = R5 = H, Q = 3, in a compound of formula I
692 F Cl OCH2C02 Ph 693 F Cl OCH2CO2 CH2Ph 694 F Cl OCH2CO2 Ph-4-CI 695 F Cl OCH2C02 CH2Ph-4-CI 696 F Cl OCH2CO2 3-Py 697 F Cl OCH (CH3) CO2 H 698 F Cl OCH (CH3 ) CO2 CH3 699 F Cl OCH (CH3) CO2 C2H5 700 F Cl OCH (CH3) CO2 Ph 701 F Cl OCH (CH3) CO2 CH2Ph 702 F Cl OCH (CH3) C02 Ph-4-CI 703 F Cl OCH (CH3) CO2 CH2Ph-4-CI 704 F Cl -OCH (CH3) CO2 3-Py 705 F Cl 0 H 706 F Cl O CH3 707 F Cl 0 C2H5 708 F Cl O Ph 709 F Cl O CH2Ph 710 F Cl 0 Ph-4 -CI 711 F Cl O CH2Ph-4-CI 712 F Cl 0 3-Py 50 713 F Cl SCH2CO2 H 714 F Cl SCH2C02 CH3 715 F Cl SCH2CO2 C2HS 716 F Cl SCH2C02 Ph 717 F Cl SCH2CO2 CH2Ph 718 F Cl SCH2CO2 Ph- 4-CI 719 F Cl SCH2CO2 CH2Ph-4-Cl 720 F Cl SCH2CO2 3-Py 721 F Cl SCH (CH3) CO2 H 722 F Cl SCH (CH3) C02 CH3 723 F Cl SCH (CH3) CO2 C2H5 724 F Cl SCH (CH3) CO2 Ph 725 F Cl .SCH (CH3) CO2 CH2Ph 726 F Cl SCH (CH3) CO2 Ph-4-CI 727 F Cl SH 728 F Cl S CH3 729 F Cl S C2H5 730 F Cl S Ph 731 F Cl S CH2Ph 732 F Cl S Ph-4-CI 733 F Cl S CH2Ph-4-CI 734 F Cl S 3-Py Ta bla 1 0
I
744 F Cl OCH2C02 CH, 51 745 F Cl OCH2CO2 C2H5
746 F Cl OCH2CO2 Ph 747 F Cl OCH2CO2 CH2Ph
748 F Cl OCH2CO2 Ph-4-CI
749 F Cl OCH2CO2 CN 750 F Cl OCH2CO2 3-Py
751 F Cl OCH (CH3) C02 H 752 F Cl OCH (CH3) C02 CH3
753 F Cl OCH (CH3) CO2 C2H5
754 F Cl OCH (CH3) C02 Ph 755 F Cl OCH (CH3) CO2 CH2Ph
756 F Cl OCH (CH3) CO2 Ph-4-CI
757 F Cl 'OCH (CH3) C02 CN 758 F Cl OCH (CH3) CO2 3-Py
759 F Cl 0 H 760 F Cl O CH3 761 F Cl O C2H5
762 F Cl 0 Ph 763 F Cl O CH2Ph
764 F Cl O Ph-4-CI
765 F Cl O CN 766 F Cl O 3-Py
767 F Cl SCH2C02 H 768 F Cl SCH2CO2 CH3 769 F Cl SCH2CO2 C2H5
770 F Cl SCH2CO2 Ph 771 F Cl SCH2CO2 CH2Ph
772 F Cl SCH2CO2 Ph-4-CI
773 F Cl SCH2CO2 CN 774 F Cl SCH2C02 3-Py
775 F H SCH (CH3) CO2 H 776 F Cl SCH (CH3) C02 CH3
777 F Cl SCH (CH3) CO2 C2H5
778 F Cl SCH (CH3) C02 Ph 779 F Cl SCH (CH3) CO2 CH2Ph
780 F Cl SCH (CH3) CO2 Ph-4-CI
781 F Cl SCH (CH3) C02 CH2Ph-4-CI
782 F Cl SCH (CH3) CO2 3-Py
783 F Cl S H 784 F Cl. S CH3
785 F Cl S C2H5
786 F Cl S Ph 52 787 F Cl CH = C (CI) C02 CN 788 F Cl CH2CH (CI) CO2 CN 789 F Cl CH = C (CI) CO2 H 790 F Cl CH2CH (CI) CO2 H 791 Cl Cl OH 792 Cl Cl OCH2C02 H 793 Cl Cl OCH (CH3) CO2 H 794 Cl Cl SCH2CO2 H 795 Cl Cl CH = C (CI) CO2 H 796 Cl Cl CH2CH (CI) CO2 H 797 C! Cl C H 798 H Cl O H 799 H Cl. OCH2CO2 H 800 H Cl OCH (CH3) CO 2 H 801 H Cl SCH2C02 H 802 H Cl CH = C (CI) CO 2 H 803 H Cl CH 2 CH (CI) CO 2 H 804 H CO CO 2 H 805 F Cl OCH 2 CO 2 Ph-4-F 806 F Cl SCH2CO2 Ph-4-F Table 1 1 H
N H
where A = B = N, R4 = R5 = H, Q = Q5, in a compound of formula I
No R, R2 X R3 807 F Cl CO2 H 808 F Cl co2 CH3 809 F Cl CO2 C2H5 810 F Cl CO2 Ph 811 F Cl CO2 CH2Ph 812 F Cl CO2 Ph-4-CI 813 F Cl CO2 CN 814 F Cl CO2 3 -Py 815 F Cl OCH2CO2 H 816 F Cl OCH2CO2 CH3 817 F Cl OCH2C02 C2H5 818 F Cl OCH2CO2 Ph Ui -P- SJ? N > r s Oí O Lp o t_p O
C0 C0 C0 O00000 CO 00 C »C» OO C »OO CX3 C» C »OO OO OO OO OO C» O? ) OO OO C »a} CO OO OO C0030000 8? w -i O to oo s s) or? 4 ^ oo. -i? or a3 -j s. -p 4 ^? - or co oo ^ cD ?? 4 ^? w - ^
O? t? ? ? , t? ? t? -n? ? -p? ? ^? i? i t? -? ? ^ t? Item? ^ n? Item? ^, t? ? ti? i i? t? ? ^
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54
864 Cl Cl OCH2CO2 H 865 Cl Cl OCH (CH3) CO2 H 866 Cl Cl SCH2CO2 H 867 Cl Cl CH = C (CI) CO 2 H 868 Cl Cl - CH 2 CH (CI) C02 H 869 Cl Cl CO 2 H 870 H Cl OH 871 H Cl OCH 2 CO 2 H 872 H Ci OCH (CH 3) CO 2 H 873 H Ci SCH 2 CO 2 H 874 H Cl CH = C (CI) CO 2 H 875 H Cl CH 2 CH (CI) CO 2 H 876 H Cl CO 2 H 877 F Cl OCH 2 CO 2 Ph-4 -F 878 F Cl SCH2CO2 Ph-4-F Ta b la 1 2
where A = B = N, R4 = R5 = H, Q = 6, in a compound of formula I
891 F Cl OCH2CO2 CH2Ph 892 F Cl OCH2C02 Ph-4-CI 893 F Cl OCH2CO2 CN 894 F Cl 0CH2C02 3-Py 55 895 F Cl OCH (CH3) C02 H 896 F Cl OCH (CH3) CO2 CH3
897 F Cl OCH (CH3) CO2 C2H5
898 F Cl OCH (CH3) C02 Ph 899 F Cl OCH (CH3) CO2 CH2Ph
900 F Cl OCH (CH3) CO2 Ph-4-CI
901 F Cl OCH (CH3) CO2 CH2Ph-4-CI
902 F Cl OCH (CH3) CO2 3-Py
903 F Cl 0 H 904 F Cl O CH3 905 F Cl O C2H5
906 F Cl O Ph 907 F Cl O CH2Ph
908 F Cl O Ph-4-CI
909 F Cl O CN 910 F Cl O 3-Py
911 F Cl SCH2CO2 H 912 F Cl SCH2C02 CH3 913 F Cl SCH2CO2 C2H5
914 F Cl SCH2C02 Ph 915 F Cl SCH2C02 CH2Ph
916 F Cl SCH2CO2 Ph-4-CI
917 F Cl SCH2C02 CN 918 F Cl SCH2CO2 3-Py 919 F H SCH (CH3) CO2 H 920 F Cl SCH (CH3) CO2 CH3 921 F Cl SCH (CH3) CO2 C2H5
922 F Cl SCH (CH3) CO2 Ph 923 F Cl SCH (CH3) CO2 CH2Ph
924 F Cl SCH (CH3) CO2 Ph-4-CI
925 F Cl SCH (CH3) CO2 CH2Ph-4-CI
926 F Cl SCH (CH3) CO2 3-Py 927 F Cl S H 928 F Cl S CH3 929 F Cl S C2H5
930 F Cl S Ph 931 F Cl S CH2Ph
932 F Cl S Ph-4-CI
933 F Cl CH = C (CI) CO2 H 934 F Cl CH2CH (CI) CO2 H 935 Cl Cl O H 936 Cl Cl OCH2C02 H 937 Cl Cl CH = C (Cl) CO2 H 938 Cl Cl CH2CH (Cl) CO2 H 56
939 Cl Cl SCH 2 CO 2 H 940 Cl Cl SCH (CH 3) CO 2 H 941 Cl Cl CO 2 H 942 H Cl OH 943 H Cl OCH 2 CO 2 H 944 H Cl OCH (CH 3) CO 2 H 945 H Cl SCH 2 CO 2 H 946 H Cl CH = C (CI ) CO2 H 947 H Cl CH2CH (CI) CO2 H 948 H Cl CO2 H 949 F Cl OCH2CO2 Ph-4-F 950 F Cl SCH2C02 Ph-4-F Table 1 3
where A = B = N, R = R5 = H, Q = 7, in a compound of formula I
68 F Cl OCH (CH3) CO2 CH3 Ui * 4 * 00 oo s! J S3 l O Ul or Ul Ul O Lp
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58
1012 Cl Cl SCH (CH3) C02 H 1013 Cl Cl H 1014 H Cl 0 H 1015 H Cl OCH 2 CO 2 H 1016 H Cl OCH (CH 3) C 0 H 1017 H Cl SCH 2 C0 2 H 1018 H Cl CH = C (CI) CO2 H 1019 H Cl CH2CH (CI) C02 H 1020 H Cl C0 H 1021 F Cl OCH2C02 Ph-4-F 1022 F Cl SCH2CO2 Ph-4-F Ta b la 14
where A = B = N, R4 = R5 = H, Q = Q8, in a compound of formula I
1037 F Cl OCH2CO2 CN 1038 F Cl OCH2CO2 3-Py 1039 F Cl OCH (CH3) C02 H 1040 F Cl OCH (CH3) CO2 CH3 1041 F Cl OCH (CH3) C02 C2H5 1042 F Cl OCH (CH3) CO2 Ph 59
1043 F Cl OCH (CH3) C02 CH2Ph
1044 F Cl OCH (CH3) C02 Ph-4-Cl
1045 F Cl OCH (CH3) C02 CH2Ph-4-CI
1046 F Cl OCH (CH3) C02 3-Py
1047 F Cl 0 H 1048 F Cl 0 CH3 1049 F Cl 0 C2H5
1050 F Cl 0 Ph 1051 F Cl 0 CH2Ph
1052 F Cl 0 Ph-4-CI
1053 F Cl 0 CH2Ph-4-CI
1054 F Cl 0 3-Py
1055 F Cl SCH2C02 H 1056 F Cl SCH2C02 CH3 1057 F Cl SCH2CO2 C2H5
1058 F Cl SCH2CO2 Ph 1059 F Cl SCH2C02 CH2Ph
1060 F Cl SCH2CO2 Ph-4-CI
1061 F Cl SCH2C02 CN 1062 F Cl SCH2CO2 3-Py 1063 F H SCH (CH3) CO2 H 1064 F Cl SCH (CH3) C02 CH3 1065 F Cl SCH (CH3) CO2 C2H5
1066 F Cl SCH (CH3) C02 Ph 1067 F Cl SCH (CH3) CO2 CH2Ph
1068 F Cl - CH = C (CI) CO2 CN 1069 F Cl CH2CH (CI) C02 CN 1070 F Cl SCH (CH3) CO2 3-Py 1071 F Cl S H 1072 F Cl S CH3 1073 F Cl S C2H5
1074 F Cl S Ph 1075 F Cl S CH2Ph
1076 F Cl S Ph-4-CI
1077 F Cl CH = C (CI) CO2 H 1078 F Cl CH2CH (CI) CO2 H 1079 Cl Cl 0 H 1080 Cl Cl OCH 2 CO 2 H 1081 Cl Cl CH = C (CI) C02 H 1082 Cl Cl CH 2 CH (CI) CO2 H 1083 Cl Cl SCH2C02 H 1084 Cl C! SCH (CH3) CO2 H 1085 Cl Cl CO2 H Ul ^ 00 00 Yes r Ul
O Ul or Ul Ul O Ul o
61 1116 F Cl OCH (CH3) CO2 Ph-4-Ci
1117 F Cl OCH (CH3) C02 CN 1118 F Cl OCH (CH3) CO2 3-Py
1119 F Cl 0 H 1120 F Cl O CH3
1121 F Cl 0 C2H5
1122 F Cl 0 Ph 1123 F Ci O CH2Ph
1124 F Cl O Ph-4-CI
1125 F Cl O CN 1126 F Cl O 3-Py
1127 F Cl SCH2C02 H 1128 F Ci SCH2C02 CH3
1129 F Cl SCH2CO2 C2H5
1130 F Cl SCH2C02 Ph 1131 F Cl SCH2CO2 CH2Ph
1132 F Cl SCH2CO2 Ph-4-CI
1133 F Cl SCH2CO2 CN 1134 F Cl SCH2CO2 3-Py
1135 F H SCH (CH3) CO2 H 1136 F Cl SCH (CH3) CO2 CH3
1137 F Cl SCH (CH3) CO2 C2H5
1138 F Cl SCH (CH3) CO2 Ph 1139 F Cl SCH (CH3) CO2 CH2Ph
1140 F Cl SCH (CH3) CO2 Ph-4-CI
1141 F Cl SCH (CH3) CO2 CH2Ph-4-CI
1142 F Cl SCH (CH3) C02 3-Py
1143 F Cl .S H 1144 F Cl S CH3 1145 F Cl S C2H5
1146 F Cl S Ph 1147 F Cl S CH2Ph
1148 F Cl S Ph-4-CI
1149 F Cl CH = C (CI) CO2 H 1150 F Cl CH2CH (CI) C02 H 1151 C! Cl O H 1152 Cl Cl OCH2C02 H 1153 Cl Cl CH = C (CI) CO2 H 1154 Cl Cl CH2CH (CI) CO2 H 1155 Cl Cl SCH2C02 H 1156 C! Cl SCH (CH3) CO2 H 1157 Cl Cl CO2 H Ul 4 00 00 NO Ul Ui O Ul O l Ul O
H
63
1188 F Cl OCH (CH3) CO2 Ph-4-CI
1189 F Cl OCH (CH3) CO2 CH2Ph-4-CI
1190 F Cl OCH (CH3) C02 3-Py
1191 F C! O H 1192 F Cl 0 CH3 1193 F Cl O C2H5
1194 F Cl O Ph 1195 F Cl O CH2Ph
1196 F Cl O Ph-4-CI
1197 F Cl O CH2Ph-4-CI
1198 F Cl O 3-Py
1199 F Cl SCH2CO2 H 1200 F Cl SCH2C02 CH3 1201 F Cl SCH2CO2 C2H5
1202 F Cl SCH2CO2 Ph 1203 F Cl SCH2CO2 CH2Ph
1204 F Cl SCH2CO2 Ph-4-CI
1205 F Cl SCH2CO2 CH2Ph-4-CI
1206 F Cl SCH2CO2 3-Py 1207 F H SCH (CH3) CO2 H 1208 F Cl SCH (CH3) CO2 CH3 1209 F Cl SCH (CH3) C02 C2H5
1210 F Cl SCH (CH3) CO2 Ph 1211 F Cl SCH (CH3) CO2 CH2Ph
1212 F Cl SCH (CH3) C02 Ph-4-CI
1213 F Ci SCH (CH3) C02 CH2Ph-4-CI
1214 F Cl SCH (CH3) C02 3-Py
1215 F Cl S H 1216 F Cl S CH 3 1217 F Cl S C2H5
1218 F Cl S Ph 1219 F Cl S CH2Ph
1220 F Cl S Ph-4-CI
1221 F Cl CH = C (CI) C02 H 1222 F Cl CH2CH (CI) CO2 H 1223 Cl Cl OH 1224 Cl Cl OCH 2 CO 2 H 1225 Cl Ci CH = C (CI) CO2 H 1226 Cl Cl CH2CH (CI) C02 H 1227 Cl Cl SCH 2 CO 2 H 1228 Cl Cl SCH (CH 3) CO 2 H 1229 Cl Cl CO 2 H 1230 H Cl OH 64 1231 H Cl OCH 2 ClO 2 H 1232 H Cl OCH (CH 3) CO 2 H 1233 H Cl SCH 2 CO 2 H 1234 H Cl CH = C (CI ) CO2 H 1235 H Cl CH2CH (CI) CO2 H 1236 H Cl CO2 H 1237 F Cl OCH2CO2 Ph-4-F 1238 F Cl SCH2CO2 Ph-4-F Ta bla 1 7 •
where sto of the formula I
1249 F Cl OCH2CO2 C2H5 1250 F Cl OCH2CO2 Ph 1251 F Cl OCH2CO2 CH2Ph 1252 F Cl OCH2CO2 Ph-4-CI 1253 F Cl OCH2CO2 CH2Ph-4-CI 1254 F Cl OCH2CO2 3-Py 1255 F Cl OCH (CH3) CO2 H 1256 F Cl OCH (CH3) C02 CH3 1257 F Cl OCH (CH3) C02 C2H5 1258 F Cl OCH (CH3) C02 Ph 1259 F Cl OCH (CH3) C02 CH2Ph 1260 F Cl OCH (CH3) CO2 Ph-4-CI 1261 F Cl OCH (CH3) C02 CH2Ph-4-CI 1262 F Cl OCH (CH3) CO2 3-Py
1263 F Cl 0 H 1264 F Cl O CH3
1265 F Cl O C2H5
1266 F Cl O Ph 1267 F Cl O CH2Ph
1268 F Cl O Ph-4-CI
1269 F Cl O CH2Ph-4-CI
1270 F Cl O 3-Py
1271 F Cl SCH2CO2 H 1272 F Cl SCH2CO2 CH3 1273 F Cl SCH2CO2 C2HS
1274 F Cl SCH2CO2 Ph 1275 F Cl SCH2CO2 CH2Ph
1276 F Cl SCH2CO2 Ph-4-CI
1277 F Cl SCH2CO2 CH2Ph-4-CI
1278 F Cl SCH2CO2 3-Py 1279 F H SCH (CH3) CO2 H 1280 F Cl SCH (CH3) CO2 CH3 1281 F Cl SCH (CH3) C02 C2H5
1282 F Cl SCH (CH3) CO2 Ph 1283 F Cl SCH (CH3) C02 CH2Ph
1284 F Cl SCH (CH3) CO2 Ph-4-C!
1285 F Cl SCH (CH3) CO2 CH2Ph-4-CI
1286 F Cl SCH (CH3) C02 3-Py 1287 F Cl S H 1288 F Cl S CH3 1289 F Cl S C2H5
1290 F Cl S Ph 1291 F Cl S CH2Ph
1292 F Cl S Ph-4-CI
1293 F Cl CH = C (CI) C02 H 1294 F Cl CH2CH (CI) CO2 H 1295 Cl Cl OH 1296 Cl Cl OCH2CO2 H 1297 Cl Cl CH = C (CI) CO2 H 1298 Cl Cl CH2CH (CI) C02 H 1299 Cl Cl SCH 2 CO 2 H 1300 Cl Cl SCH (CH 3) C 0 2 H 1301 Cl Cl H H 1302 H Cl 0 H 1303 H Ci OCH 2 CO 2 H 1304 H Cl OCH (CH 3) CO 2 H 66
1305 H Cl SCH2CO2 H 1306 H Cl CH = C (CI) C02 H 1307 H Cl CH2CH (CI) C02 H 1308 H Cl CO 2 H 1309 F Cl OCH 2 CO 2 Ph-4-F 1310 F Cl SCH, CO, Ph-4- F Ta b la 1 8
where A = B = N, R4 = R5 = H, Q-Q12, in a compound of the formula I
1321 F Cl OCH 2 CO 2 C 2 H 5 CH 3 1322 F Cl OCH 2 CO 2 H NH 2 1323 F Cl OCH 2 CO 2 CH 3 NH 2 1324 F Cl OCH 2 CO 2 C 2 H 5 NH 2 1325 F Cl OCH 2 CO 2 CN NH 2 1326 F Cl OCH 2 CO 2 CN CH 3 1327 F Cl OCH (CH 3) CO 2 H CH 3 1328 F Cl OCH (CH3) CO2 CH3 CH3 1329 F Cl OCH (CH3) CO2 C2H5 CH3 1330 F Cl OCH (CH3) C02 H NH2 1331 F Cl OCH (CH3) CO2 CH3 NH2 1332 F Cl OCH (CH3) C02 C2H5 NH2 1333 F Cl OCH (CH3) CO2 CN NH2 1334 F Cl 0 HH 1335 F Cl OH CH3 67
1345 F Cl SCH2C02 C2H5 CH3
1346 F Cl SCH2C02 H NH2
1347 F Cl SCH2CO2 CH3 NH2
1348 F Cl SCH2CO2 C2H5 NH2
1349 F Cl SCH2CO2 CN NH2
1350 F Cl SCH2CO2 CN CH3
1351 F H SCH (CH3) C02 H CH3
1352 F Cl SCH (CH3) CO2 CH3 CH3
1353 F Cl SCH (CH3) CO2 C2H5 CH3
1354 F Cl SCH (CH3) C02 H NH2
1355 F Cl SCH (CH3) CO2 CH3 NH2
1356 F Cl SCH (CH3) C02 C2H5 NH2
1357 F Cl CH = C (CI) CO2 H NH2
1358 F Cl CH2CH (CI) CO2 H NH2
1359 F Cl CH = C (CI) CO2 CN NH2
1360 F Cl CH2CH (CI) C02 CN NH2
1361 F Cl S H CH3
1362 F Cl S H NH2
1363 F Cl CH = C (CI) CO2 H CH3
1364 F Cl CH2CH (CI) C02 H CH3
1365 F Cl CH = C (CI) CO2 CN CH3
1366 F Cl CH2CH (CI) CO2 CN CH3
1367 Cl Cl O H NH2
1368 Cl Cl OCH2C02 H CH3
1369 Cl Cl OCH (CH3) CO2 H CH3
1370 Cl Cl SCH2CO2 H CH3
1371 Cl Cl CH = C (CI) CO2 H CH3
1372 Cl Cl CH2CH (CI) CO2 H CH3
1373 Cl Cl C02 H CH3
1374 H Cl O H CH3
1375 H Cl OCH2C02 H CH3
1376 H Cl OCH (CH3) C02 H CH3
1377 H Cl SCH2CO2 H CH3
1378 H Cl CH = C (CI) C02 H NH2
1379 H Cl CH2CH (CI) CO2 H NH2
1380 H Cl C02 H NH2 68
1381 H Cl OCH2C02 H NH2 1382 H Cl SCH2CQ2 H NH2 T a b l a 1 9
where A = B = N, R4 = R5 = H, Q = Q13, in a compound of formula I
1393 F Cl OCH2C02 C2H5 CH3 1394 F Cl OCH2CO2 H NH2 1395 F Cl 0CH2C02 CH3 NH2 1396 F Cl OCH, CO2 C2H5 NH2 1397 F Cl OCH2C02 CN NH2 1398 F Cl OCH2CO2 CN CH3 1399 F Cl OCH (CH3) CO2 H CH3 1400 F Cl OCH (CH3) C02 CH3CH3 1401 F Cl OCH (CH3) CO2 C2H5 CH3 1402 F Cl OCH (CH3) C02 H NH2 1403 F Cl OCH (CH3) CO2 CH3 NH2 1404 F Cl OCH (CH3) C02 C2H5 NH2 1405 F Cl OCH (CH3) CO 2 CN NH 2 1406 F Cl OCH (CH 3) CO 2 CN CH 3 1407 F Cl 0 H CH 3 1408 F Cl O CH 3 CH 3 1409 F Cl 0 C 2 H 5 CH 3 1410 F Cl 0 H NH, 69
1411 F Cl O CH3 NH2
1412 F C! O C2H5 NH2
1413 F Cl O CN NH2
1414 F C! O CN CH3
1415 F Cl SCH2CO2 H CH3
1416 F Cl SCH2C02 CH3 CH3
1417 F Cl SCH2CO2 C2H5 CH3
1418 F Cl SCH2CO2 H NH2
1419 F Cl SCH2C02 CH3 NH2
1420 F Cl SCH2CO2 C2H5 NH2 NH2
1421 F Cl SCH2CO2 CN 1422 F Cl SCH2CO2 CN CH3
1423 F H SCH (CH3) CO2 H CH3
1424 F Cl SCH (CH3) C02 CH3 CH3
1425 F Cl SCH (CH3) CO2 C2H5 CH3
1426 F Cl SCH (CH3) CO2 H NH2
1427 F Cl SCH (CH3) CO2 CH3 NH2
1428 F Cl SCH (CH3) CO2 C2H5 NH2
1429 F Cl CH = C (CI) CO2 H NH2
1430 F Cl CH2CH (Ci) CO2 H NH2
1431 F Cl CH = C (CI) CO2 CN NH2
1432 F Cl CH2CH (CI) CO2 CN NH2
1433 F Cl S H CH3
1434 F Cl S H NH2
1435 F Cl CH = C (CI) CO2 H CH3
1436 F Cl CH2CH (CI) C02 H CH3
1437 F Cl CH = C (CI) CO2 CN CH3
1438 F Cl CH2CH (CI) C02 CN CH3
1439 Cl Cl 0 H NH2
1440 Cl Cl OCH2CO2 H CH3
1441 Cl Cl OCH (CH3) C02 H CH3
1442 Cl Cl SCH2CO2 H CH3
1443 Cl Cl CH = C (CI) CO2 H CH3
1444 Cl Cl CH2CH (CI) C02 H CH3
1445 Cl Cl CO2 H CH3
1446 H Cl 0 H CH3
1447 H Cl OCH2CO2 H CH3
1448 H Cl OCH (CH3) CO2 H CH3
1449 H Cl SCH2CO2 H CH3
1450 H Cl CH = C (CI) CO2 H NH2
1451 H Cl CH2CH (CI) C02 H NH2 70 1452 H Cl CO 2 H NH 2 1453 H Cl OCH 2 CO 2 H NH 2 1454 H Cl SCH, CO, H NH 2
Ta b l a 20
where A = B = N, R4 = 5 = H, R? _ = CH3 / Q = Q14, in a compound of the formula I
1465 F Cl OCH 2 CO 2 C 2 H 5 CH 3 1466 F Cl OCH 2 CO 2 H NH 2 1467 F Cl OCH 2 CO 2 CH 3 NH 2 1468 F Cl OCH 2 CO 2 C 2 H 5 NH 2 1469 F Cl OCH 2 CO 2 CN NH 2 1470 F Cl OCH 2 CO 2 CN CH 3 1471 F Cl OCH (CH 3) CO 2 H CH 3 1472 F Cl OCH (CH3) C02 CH3 CH3 1473 F Cl OCH (CH3) CO2 C2H5 CH3 1474 F Cl OCH (CH3) CO2 H NH2 1475 F Cl OCH (CH3) CO2 CH3 NH2 1476 F Cl OCH (CH3) C02 C2H5 NH2 1477 F Cl OCH (CH3) C02 CN NH2 1478 F Cl OCH (CH3) C02 CN CH3 1479 F Cl OH CH3 1480 F Cl O CH3 CH3 1481 F Cl O C2H5 CH3 71 1482 F Cl OH NH2
1483 F Cl O CH3 NH2
1484 F Cl O C2H5 NH2
1485 F Cl O CN NH2
1486 F Cl O CN CH3
1487 F Cl SCH2C02 H CH3
1488 F Cl SCH2CO2 CH3 CH3
1489 F Cl SCHoCOo C2H5 CH3
1490 F Cl SCH2CO2 H NH2
1491 F Cl SCH2CO2 CH3 NH2
1492 F Cl SCH2CO2 C2H5 NH2
1493 F Cl SCH2CO2 CN NH2
1494 F Cl SCH2CO2 CN CH3
1495 F H SCH (CH3) C02 H CH3
1496 F Cl SCH (CH3) CO2 CH3 CH3
1497 F Cl SCH (CH3) C02 C2H5 CH3
1498 F Cl SCH (CH3) CO2 H NH2
1499 F Cl SCH (CH3) CO2 CH3 NH2
1500 F Cl SCH (CH3) CO2 C2H5 NH2
1501 F Cl CH = C (CI) CO2 H NH2
1502 F Ci CH2CH (CI) CO2 H NH2
1503 F Cl CH = C (CI) CO2 CN NH2
1504 F Cl CH2CH (CI) CO2 CN NH2
1505 F Cl S H CH3
1506 F Cl S H NH2
1507 F Cl CH = C (CI) CO2 H CH3
1508 F Cl CH2CH (CI) C02 H CH3
1509 F. Cl CH = C (CI) CO2 CN CH3
1510 F Cl CH2CH (CI) CO2 CN CH3
1511 Cl Cl O H NH2
1512 Cl Cl OCH2CO2 H CH3
1513 Cl Cl OCH (CH3) C02 H CH3
1514 Cl Cl SCH2CO2 H CH3
1515 Cl Cl CH = C (CI) CO2 H CH3
1516 Cl Cl CH2CH (CI) C02 H CH3
1517 Cl Cl CO2 H CH3
1518 H Cl O H CH3
1519 H Cl OCH2CO2 H CH3
1520 H Cl OCH (CH3) CO2 H CH3
1521 H Cl SCH2C02 H CH3
1522 H Cl CH = C (CI) CO2 H NH2 72
1523 H Cl CH2CH (CI) CO. i H NH2 1524 H Cl CO 2 H NH2 1525 H Cl OCH2C02 H NH2 1526 H Cl SCH2CO2 H NH2 Ta b l a 21
where A = B = N, R = R5 = H, Q = Q15, in a compound of formula I
1537 F Cl OCH2CO2 C2H5 CH3 1538 F C! OCH2CO2H NH2 1539 F Cl OCH2C02 CH3 NH2 1540 F Cl OCH2CO2 C2H5 NH2 1541 F Cl OCH2CO2CN NH2 1542 F Cl OCH2CO2CN CH3 1543 F Cl OCH (CH3) CO2 H CH3 1544 F Cl OCH (CH3) C02 CH3CH3 1545 F Cl OCH (CH3) CO2 C2H5 CH3 1546 F Cl OCH (CH3) C02 H NH2 1547 F Cl OCH (CH3) CO2 CH3 NH2 1548 F Cl OCH (CH3) CO2 C2H5 NH2 1549 F Cl OCH (CH3) CO2 CN NH2 1550 F Cl OCH (CH3) CO 2 CN CH 3 1551 F Cl 0 H CH 3 1552 F Cl O CH 3 CH 3 1553 F Cl O C 2 H 5 CH 3 1554 F Cl 0 H NH, 73
1555 F Cl O CH3 NH2
1556 F Cl O C2H5 NH2
1557 F Cl O CN NH2
1558 F Cl 0 CN CH3
1559 F Cl SCH2CO2 H CH3
1560 F Cl SCH2C02 CH3 CH3
1561 F Cl SCH2CO2 C2H5 CH3
1562 F Cl SCH2CO2 H NH2
1563 F Cl SCH2CO2 CH3 NH2
1564 F Cl SCH2CO2 C2H5 NH2
1565 F Cl SCH2C02 CN NH2
1566 F Cl SCH2CO2 CN CH3
1567 F H SCH (CH3) CO2 H CH3
1568 F Cl SCH (CH3) C02 CH3 CH3
1569 F Cl SCH (CH3) CO2 C2H5 CH3
1570 F Cl SCH (CH3) CO2 H NH2
1571 F Cl SCH (CH3) CO2 CH3 NH2
1572 F Cl SCH (CH3) CO2 C2H5 NH2
1573 F Cl CH = C (CI) C02 H NH2
1574 F Cl CH2CH (CI) CO2 H NH2
1575 F Cl CH = C (CI) CO2 CN NH2
1576 F Cl CH2CH (CI) CO2 CN NH2
1577 F Cl S H CH3
1578 F Cl S H NH2
1579 F Cl CH = C (CI) CO2 H CH3
1580 F Cl CH2CH (CI) C02 H CH3
1581 F Cl CH = C (CI) CO2 CN CH3
1582 F Cl CH2CH (CI) CO2 CN CH3
1583 Cl Cl O H NH2
1584 C! Cl OCH2CO2 H CH3
1585 Cl Cl OCH (CH3) C02 H CH3
1586 Cl Cl SCH2CO2 H CH3
1587 C! Cl CH = C (CI) CO2 H CH3
1588 Cl Cl CH2CH (CI) CO2 H CH3
1589 Cl Cl CO2 H CH3
1590 H C! 0 H CH3
1591 H Cl OCH2CO2 H CH3
1592 H Cl OCH (CH3) CO2 H CH3
1593 H Cl SCH2CO2 H CH3
1594 H Cl CH = C (Ci) CO2 H NH2
1595 H Cl CH2CH (CI) C02 H NH2
1596 H Cl CO2 H NH2 74
1597 H Cl OCH2CO2 H NH2 1598 H Cl SCH2CO2 H NH2
Ta b l a 22
where A = B = N, R = R5 = H, Q = 16, in a compound of formula I
No R. R2 X R3 1599 F Cl C02 H 1600 F Cl CO2 CH3 1601 F Cl CO2 C2H5 1602 F Cl co2 Ph 1603 F Cl CO2 CH2Ph 1604 F Cl co2 Ph-4-CI 1605 F Cl CO2 CH2Ph-4-CI 1606 F Cl CO2 3-Py 1607 F Cl OCH 2 CO 2 H 1608 F Cl OCH 2 CO 2 CH 3 1609 F Cl OCH 2 CO 2 C 2 H 5 1610 F Cl OCH 2 CO 2 Ph 1611 F Cl OCH 2 CO 2 CH 2 Ph 1612 F Cl OCH 2 CO 2 Ph-4-CI 1613 F Cl OCH 2 CO 2 CH 2 P h 4 4 Cl 1614 F Cl OCH2C02 3-Py 1615 F Cl OCH (CH3) CO2 H 1616 F Cl OCH (CH3) CO2 CH3 1617 F Cl OCH (CH3) CO2 C, H5 1618 F Cl OCH (CH3) CO2 Ph 1619 F Cl OCH (CH3 ) CO2 CH2Ph 1620 F Cl OCH (CH3) C02 Ph-4-CI 1621 F Ci OCH (CH3) CO2 CH2Ph-4-CI 1622 F Cl OCH (CH3) CO2 3-Py 1623 F Cl OH 1624 F Cl O CH3 1625 F Cl O C2H5 1626 F Cl O Ph 1627 F Cl O CH2Ph 75 1628 F Cl O Ph-4-CI
1629 F Cl O CH2Ph-4-CI
1630 F Cl O 3-Py
1631 F Cl SCH2CO2 H 1632 F Cl SCH2CO2 CH3 1633 F Cl SCH2CO2 C2H5
1634 F Cl SCH2CQ2 Ph 1635 F Cl SCH2CO2 CH2Ph
1636 F Cl SCH2CO2 Ph-4-CI
1637 F Cl SCH2CO2 CH2Ph-4-CI
1638 F Cl SCH2CO2 3-Py
1639 F H SCH (CH3) CO2 H 1640 F Cl SCH (CH3) C02 CH3 1641 F Cl SCH (CH3) CO2 C2H5
1642 F Cl SCH (CH3) CO2 Ph 1643 F Cl SCH (CH3) C02 CH2Ph
1644 F Cl SCH (CH3) CO2 Ph-4-CI
1645 F Cl SCH (CH3) CO2 CH2Ph-4-CI
1646 F Cl SCH (CH3) C02 3-Py 1647 F Cl S H 1648 F Cl S CH3 1649 F Cl S C2H5
1650 F Ci S Ph 1651 F Cl S CH2Ph
1652 F Cl S Ph-4-CI
1653 F Cl CH = C (CI) CO2 H 1654 F Cl CH2CH (Ci) C02 H 1655 Cl Cl OH 1656 Cl Cl OCH2C02 H 1657 Cl Cl CH = C (CI) CO2 H 1658 Cl Cl CH2CH (CI) CO2 H 1659 Cl Cl SCH2C02 H 1660 Ci Ci SCH (CH3) CO2 H 1661 Cl Cl C02 H 1662 H Cl OH 1663 H Cl OCH2C02 H 1664 H Cl OCH (CH3) CO2 H 1665 H Cl SCH2CO2 H 1666 H Cl CH = C (Ci) C02 H 1667 H Cl CH2CH (CI) CO2 H 1668 H Cl CO2 H 1669 F Cl OCH2CO2 Ph-4-F Ul -P- 00 00 Ni (Ul
OR
O- ID
H P »H)
77
1701 F Cl CH2CH (Cl) CO Q1
1702 F Cl CH2CH (CI) CO Q2
1703 F Cl CH2CH (CI) CO Q3
1704 F Cl CH2CH (CI) CO Q4
1705 F Cl CH2CH (CI) CO Q5
1706 F Cl CH2CH (CI) CO Q6
1707 F Cl CH2CH (CI) CO Q7
1708 F Cl CH2CH (CI) CO Q8
1709 F Cl CH2CH (CI) CO Q9
1710 F Cl CH2CH (C!) CO Q10
1711 F Cl CH2CH (CI) CO Q11
1712 F Cl CH2CH (CI) CO Q12
1713 F Cl CH2CH (CI) CO Q13
1714 F Cl CH2CH (CI) CO Q14
1715 F Cl CH2CH (CI) CO Q16
1716 F Cl CH = C (CI) CO Q1
1717 F Cl CH = C (CI) CO Q2
1718 F Cl CH = C (CI) CO Q3
1719 F Cl CH = C (CI) CO Q4
1720 F Cl. CH = C (CI) CO Q5
1721 F Cl CH = C (CI) CO Q6
1722 F Cl CH = C (CI) CO Q7
1723 F Cl CH = C (Cl) CO Q8
1724 F Cl 'CH = C (CI) CO Q9
1725 F Cl CH = C (CI) CO Q10
1726 F Cl CH = C (CI) CO Q11
1727 F Cl CH = C (CI) CO Q12
1728 F Cl CH = C (CI) CO Q13
1729 F Cl CH = C (CI) CO Q14
1730 F Cl CH = C (CI) CO Q16
1731 F Cl CO Q1
1732 F Cl 'CO Q2
1733 F Cl CO Q3
1734 F Cl CO Q4
1735 F Cl co Q5
1736 F Cl CO Q6
1737 F Cl CO Q7
1738 F Cl CO Q8
1739 F Cl CO Q9
1740 F Cl CO Q10
1741 F Cl CO Q11
1742 F Cl CO Q12
1743 F Cl CO Q13 78 1744 F Cl CO Q14
1745 F Cl CO Q16
1746 F Cl SCH2CO Q1
1747 F Cl SCHjCO Q2
1748 F Cl SCH2CO Q3
1749 F Cl SCH2CO Q4
1750 F Cl SCH2CO Q5
1751 F Cl SCH2CO Q6
1752 F Cl SCH2CO Q7
1753 F Cl SCH2CO Q8
1754 F Cl SCH2CO Q9
1755 F Cl SCH2CO Q10
1756 F Cl SCH2CO Q11
1757 F Cl SCH2CO Q12
1758 F Cl SCH2CO Q13
1759 F Cl SCH2CO Q14
1760 F Cl SCH2CO Q16
1761 Cl Cl CH = C (CI) CO Q1
1762 Cl Cl CH = C (CI) CO Q3
1763 Cl Cl CH = C (CI) CO Q6
1764 C! Cl CH = C (CI) CO Q7
1765 Cl Cl CH = C (CI) CO Q8
1766 Cl Cl CH = C (CI) CO Q10
1767 Cl Cl CH = C (CI) CO Q11
1768 Cl Cl - CH = C (CI) CO Q12
1769 Cl Cl CH = C (CI) CO Q16
1770 Cl Cl CH2CH (CI) CO Q1
1771 Cl Cl CH2CH (CI) CO Q3
1772 Cl Cl CH2CH (CI) CO Q6
1773 Cl Cl CH2CH (CI) CO Q7
1774 Cl Cl CH2CH (CI) CO Q8
1775 Cl Cl CH2CH (CI) CO Q10
1776 Cl Cl CH2CH (CI) CO Q11
1777 Ci Cl CH2CH (CI) CO Q12
1778 Cl Cl CH2CH (CI) CO Q16
1779 Cl Cl OCH2CO Q1
1780 Cl Cl 'OCH2CO Q3
1781 Cl Cl OCH2CO Q6
1782 Cl Cl OCH2CO Q7
1783 Cl Cl OCH2CO Q8
1784 Cl Cl OCH2CO Q10
1785 Cl Cl OCH2CO Q11
1786 Cl Cl OCH2CO Q12
1787 Cl Cl OCH2CO Q16 r- CO (O N 00 ooooo
r
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oooooooooooooooo oo? ooooooooxxxx xxxxxxxxxxxx
CO O) O t- (\ | C 'c l l CD N CO CD O r- CM C to ra si pp ro ffl p ffl Q ffi pi ggy OOOOOO (M co' < t? (O? Oo s)? t- CM, c tt ií. (o N co s? h- K t ^ h- K h- 8888 8888888888s8ssss CsMsCMsCMsCM CsMsCM CsM CsMsCMsCMsCO
m m or I? Or I? CN C or go, OR CO co r • o- m
80
1831 H Cl CH2CH (CI) CO Q12
1832 H Cl CH2CH (CI) CO Q16
1833 H Cl OCHoCO Q1
1834 H Cl OCH2CO Q3
1835 H Cl OCH2CO Q6
1836 H Cl OCH2CO Q7
1837 H Cl OCH2CO Q8
1838 H Cl OCH2CO Q10
1839 H C! OCH2CO Q11
1840 H Cl OCH2CO Q12
1841 H Cl OCH2CO Q16
1842 H Cl SCH2CO Q1
1843 H Cl 'SCH2CO Q3
1844 H Cl SCH2CO Q6
1845 H Cl SCH2CO Q7
1846 H Cl SCH2CO Q8
1847 H Ci SCH2CO Q10
1848 H Cl SCH2CO Q11
1849 H Cl SCH2CO Q12
1850 H Cl SCH2CO Q16
1851 H Cl CO Q1
1852 H Cl CO Q3
1853 H Cl CO Q6
1854 H Cl CO Q7
1855 H Cl CO Q8
1856 H Cl CO Q10
1857 H Cl CO Q11
1858 H Cl CO Q12
1859 H Cl CO Q16
1860 H Cl OCH (CH3) CO Q1
1861 H Cl OCH (CH3) CO Q3
1862 H Cl OCH (CH3) CO Q6
1863 H Cl OCH (CH3) CO Q7
1864 H Cl. OCH (CH3) CO Q8
1865 H Cl OCH (CH3) CO Q10
1866 H Cl OCH (CH3) CO Q11
1867 H Cl OCH (CH3) CO Q12
1868 H Cl OCH (CH3) CO Q16 81
where R3 = R = R5 = H, A = B = N, R? 0 = CH3, in a compound of the formula I
1873 F Cl CH2CH (CI) C02 Q1 HCl 1874 F Cl CH = C (CI) CO2 Q1 HCl 1875 F Cl OCH2C02 Q1 H3P04 1876 F Cl OCH2CO2 Q1 CH3C02H 1877 F Cl OCH2CO2 Q1 HCO2CO2H 1878 F Cl SCH2C02 Q1 HC02C02H 1879 F Cl CO2 Q1 HCO2CO2H 1880 F Cl CH2CH (CI) C02 Q1 HC02C02H 1881 F Cl CH = C (CI) C02 Q1 HC02C02H 1882 Cl Cl O Q1 HCl 1883 Cl Cl OCH2C02 Q1 HCl 1884 Cl Cl SCH2CO2 Q1 HCl 1885 Cl Cl C02 Q1 HCl 1886 Cl Cl CH2CH (CI) CO2 Q1 HCi 1887 Cl Cl CH = C (CI) C02 Q1 HCl 1888 Cl Cl O Q1 HCO2CO2H 1889 Cl Cl OCH2CO2 Q1 HCO2CO2H 1890 Cl Cl SCH2C02 Q1 HC02C02H 1891 Cl C! CO2 Q1 HCO2CO2H 1892 Cl Cl CH2CH (CI) C02 Q1 HC02C02H 1893 Cl Cl CH = C (CI) CO2 Q1 HCO2CO2H 1894 H Cl O Q1 HCl 1895 H Cl 0CH2C02 Q1 HCl 1896 H Cl SCH2CO2 Q1 HCl 1897 H Cl CO2 Q1 HCl 1898 HCl CH2CH (CI) C02 Q1 HCl 1899 H Cl CH = C (CI) C02 Q1 HCl 1900 H Cl O. Q1 HC02C02H 82 1901 H Cl OCH2C02 Q1 HC02C02H
1902 H Cl SCH2CO2 Q1 HCO2CO2H
1903 H Cl co2 Q1 HC02C02H
1904 H Cl CH2CH (CI) C02 Q1 HCO2CO2H
1905 H Cl CH = C (Ci) C02 Q1 HCO2CO2H
1906 F Cl 0 Q3 HCl
1907 F Cl OCH2CO2 Q3 HCl
1908 F Cl SCH2C02 Q3 HCl
1909 F Cl C02 Q3 HCl
1910 F Cl CH2CH (CI) C02 Q3 HCl
1911 F Cl CH = C (CI) C02 Q3 HCl
1912 F Cl O Q7 HCl
1913 F Cl OCH2C02 Q7 HCl
1914 F Cl SCH2C02 Q7 HCl
1915 F Cl CO2 Q7 HCl
1916 F Cl CH2CH (CI) C02 Q7 HCl
1917 F Cl CH = C (Cl) CO2 Q7 HCl
1918 F Cl 0 Q8 HCl
1919 F Cl OCH2C02 Q8 HCl
1920 F Cl SCH2CO2 Q8 HCl
1921 F Cl C02 Q8 HCl
1922 F Cl CH2CH (CI) CO2 Q8 HCl
1923 F Cl CH = C (CI) C02 Q8 HCl
1924 F Cl 0 Q10 HCl
1925 F Cl OCH2CO2 Q10 HCl
1926 F Cl SCH2C02 Q10 HCl
1927 F Cl C02 Q10 HCl
1928 F Cl CH2CH (CI) C02 Q10 HCl
1929 F Cl CH = C (CI) CO2 Q10 HCl
1930 F Cl 0 Q11 HCl
1931 F Cl OCH2CO2 Q11 HCl
1932 F Cl SCH2C02 Q11 HCl
1933 F Cl C02 Q11 HCl
1934 F Cl CH2CH (CI) C02 Q11 HCl
1935 F Cl CH = C (CI) C02 Q11 HC!
1936 Cl Cl O Q12 HCl 1937 Cl Cl OCH2CO2 Q12 HCl 1938 Cl Cl SCH2CO2 Q12 HCl 1939 Cl Cl C02 Q12 HCl 1940 Cl Cl CH2CH (CI) C02 Q12 HCl 1941 Cl Cl CH = C (CI) CO? Q12 HCl 83 Ta b la 25
where compound of the formula
1945 F Cl NH CO H C02CH3 Q1 NN 1946 F Cl NH CO Ph-4-CI H Q1 NN 1947 F Cl NH CO - CH3 C02CH3 Q1 NN 1948 F Cl NH CO HH Q1 N CH 1949 F Cl NH CO CH3 CH3 Q1 N CC02CH3
1950 F Cl NH CO Cl Cl Q1 N CCONMe2
1951 F Cl NH CO C2H5 C02CH3 Q1 N CH 1952 F Cl NH with CH3 CONHPh Q1 N CH 1953 F Cl NH CO Ph-4-CI CO2NMe2 Q1 N CCI 1954 F Cl NH CO HH Q1 CH N 1955 F Cl NSO2CH3 CO HH Q1 NN 1956 F Cl NSO2CH3 CO HH Q1 N CH 1957 F CN NS02CH3 co HH Q1 CH N 1958 FC! NSO2CF3 CO HH Q1 NN 1959 F CN NS02CF3 co HH Q1 N CH 1960 F Cl NSO2CF3 CO HH Q1 CH N 1961 p Cl NSO2CH3 CH2 HH Q1 NN 1962 F Cl NS02CH3 CH2 HH Q1 N CH 1963 F Cl NSO2CH3 CH2 HH Q1 CH N 1964 F Cl NS02CF3 CH2 HH Q1 NN 1965 F Cl NSO2CF3 CH2 HH Q1 N CH 1966 F Cl NSO2CF3 CH2 HH Q1 CH N 1967 F Cl NS02CH3 CO HH Q2 NN 1968 F CN NSO2CH3 CO HH Q2 N CH 1969 F Cl NS02CH3 CO HH Q2 CH N 1970 F Cl NS02CF3 CO HH Q2 NN 1971 F Cl NSO2CF3 CO HH Q2 N CH 84
1972 F CN NSO2CF3 CO H H Q2 CH N
1973 F Cl NS02CH3 CH2 H H Q2 N N
1974 F Cl NS02CH3 CH2 H H Q2 N CH
1975 F Cl NSO2CH3 CH2 H H Q2 CH N
1976 F Cl NSO2CF3 CH2 H H Q2 N N
1977 F CN NSO2CF3 CH2 H H Q2 N CH
1978 F Cl NSO2CF3 CH2 H H Q2 CH N
1979 F CN NSO2CH3 CO H H Q3 N CH
1980 F Cl NSO2CH3 CO H H Q3 CH N
1981 F Cl NSO2CF3 CO H H Q3 N N
1982 F Cl NS02CH3 CH2 H H Q3 N N
1983 F Cl NSO2CH3 CH2 H H Q3 N CH
1984 F Cl NS02CH3 CH2: H H Q3 CH N
1985 F Cl NSO2CH3 CO H H Q7 N CH
1986 F Cl NS02CH3 CO H H Q7 CH N
1987 F Cl NS02CH3 CO H H Q7 N N
1988 F Cl NSO2CH3 CH2 H H Q7 N N
1989 F Cl NS02CH3 CH2 H H Q7 N CH
1990 F Cl NS02CH3 CH2 H H Q7 CH N
1991 F Cl NSO2CH3 CO H H Q8 N N
1992 F Cl NS02CH3 CO H H Q8 CH N
1993 F Cl NSO2CH3 CO H H Q8 N CH
1994 F Cl NS02CF3 CO H H Q8 N N
1995 F Cl NSO2CF3 CO H H Q8 CH N
1996 F Cl NSO2CF3 CO H H Q8 N CH
1997 F Cl NS02Et CO CH3 CH3 Q8 N N
1998 F Cl NS02Et co CH3 CH3 Q8 CH N
1999 F Cl NS02Et co CH3 CH3 Q8 N CH
2000 ClCl NSO2CH3 CO H H Q8 N N
2001 Cl Cl NSO2CH3 CO H H Q8 CH N
2002 Cl Cl NS02CH3 CO H H Q8 N CH
2003 Cl Cl NS02CF3 CO H H Q8 N N
2004 Cl Cl NS02CF3 CO H H Q8 CH N
2005 Cl Cl NS02CF3 CO H H Q8 N CH
2006 Cl Cl NS02Et co CH3 CH3 Q8 N N
2007 Cl Cl NS02Et co CH3 CH3 Q8 CH N
2008 Cl Cl NSO2Et CO CH3 CH3 Q8 N CH
2009 F Cl CH2C (CI) CO H H Q8 N N
2010 F Cl CH2C (CI) CO H H Q8 CH N
2011 F Cl CH2C (CI) CO H H Q8 N CH
2012 F Cl CH2C (Cl) CO H H Q1 N N
2013 F Cl CH2C (CI) CO H H Q1 CH N
2014 F Cl CH2C (CI) co H H Q1 N CH 85
2015 H Cl CH = C (CI;) CO H H Q1 N N
2016 F Cl OCH2 CO H H Q1 N N
2017 F Cl SCH2 CO H H Q3 N N
2018 F Cl .CH2C (CI) CO H H Q10 N CH
2019 H Ci CH = C (CI) i CO H H Q10 N N
2020 F Cl OCH2 CO H H Q10 N N
2021 F Cl SCH2 CO H H Q10 N N
2022 F Cl CH2C (CI) CO H H Q11 N CH
2023 H Cl CH = C (CI) CO H H Q11 N N
2024 F Cl OCH2 CO H H Q11 N N
2025 F Cl SCH2 CO, H H Q11 N N
2026 F Cl CH2C (CI) CO H H Q12 N CH
2027 H Cl CH = C (CI) CO H H Q12 N N
2028 F Cl OCH2 CO H H Q12 N N
2029 F Cl SCH2 co H H Q12 N N
2030 F Cl CH2C (CI) CO H H Q16 N CH
2031 H Cl CH = C (CI) CO H H Q16 N N
2032 F Cl OCH2 CO. H H Q16 N N
2033 F Cl SCH2 CO H H Q16 N N
2034 F Cl NS02CH3 CO H H Q7 N N
2035 F Cl NS02CH3 CO H H Q10 N N
2036 F Cl NS02CH3 CO H H Q11 N N
2037 F Cl NS02CH3 CO H H Q12 N N
2038 F Cl NS02CH3 CO H H Q16 N N
2039 F Cl NS02CH3 CH2 H H Q7 N N
2040 F Cl NS02CH3 CH2 H H Q10 N N
2041 F Cl NS02CH3 CH2 H H Q11 N N
2042 F Cl NS02CH3 CH2 H H Q12 N N
2043 F Cl NS02CH3 CH2 H H Q16 N N
2044 Cl Cl NS02CH3 CO H H Q7 N N
2045 Cl Cl NS02CH3 CO H H Q10 N N
2046 Cl Cl NS02CH3 CO H H Q11 N N
2047 Cl Cl NS02CH3 CO H H Q12 N N
2048 Cl Cl NS02CH3 CO H H Q16 N N
2049 Cl Cl NS02CH3 CH2 H H Q7 N N
2050 Cl Cl NS02CH3 CH2 H H Q10 N N
2051 Ci Cl NS02CH3 CH2 H H Q11 N N
2052 Cl Cl NS02CH3 CH2 H H Q12 N N
2053 Cl Cl NS02CH3 CH2 H H Q16 N N
2054 H Cl NS02CH3 CO H H Q7 N N
2055 H Cl NS02CH3 CO H H Q10 N N
2056 H Cl NS02CH3 CO H H Q11 N N Ul 4 4 00 OO NO N5 Ul
O Ul O Ul O Ul D Ul
87
The compounds of the formula I of the present invention can be prepared by the following processes:
Scheme 1
lll 10 Ester and amide bonds For structures II and III, where X is, for example, C03, 0CH (R6) C02, SCH (R6) C02, CH2CH (Cl) C02, CH = C (C1) C0 and Y is, for example, OH, NH2: L5 Compounds II, or their sodium or potassium salts, are reacted with one of the following reagents: SOC1., (C0C1) 2, C0C12, PC13 or P0Cl3j in a solvent, such with chloroform, dichloromethane, carbon tetrachloride, hexane, benzene, toluene, tetrahydrofuran, dioxane, acetone 0 or methyl ethyl ketone, to supply an acid chloride. This acid chloride is then reacted with the intermediate III (optionally in the presence of
bases, such as Et3N, pyridine, NaOH, KOH, Na2C03, K2C03, NaHCO,) at a temperature from -40 ° C to the boiling point of the solvent, for 3 minutes to 8 hours, to supply the final product I. Intermediate II can be obtained from the ester (made by known methods, such as those described in EP 0 083 055 A2) by reacting with 10,003, NaOH + or KOH, in ethanol, then with an inorganic acid, such as the acid hydrochloric. Intermediate III (where R3 is alkyl) can be obtained from known reactions of an aldehyde with IV, in the presence or absence of ammonium hydroxide.
89
Ether, thioether, amine bonds For structure II (where X is O, S, NH) and structure III (where Y = C1, OS02CH3, etc.) the compounds II are reacted with the intermediates III, in the presence of bases, such as Et3N, pyridine, NaOH, KOH, Na2CO;, K_, C03, NaHC03, NaH, NaOCH3, NaOC2H5, in a solvent, such as tetrahydrofuran, dioxane, acetone, methyl-ethyl -LO-ketone, acetonitrile, N, '-dimethylformamide, at a temperature from -40 ° C to the boiling point of the solvent, for 30 minutes up to 18 hours, to supply the final product I.
Scheme 2 L5
0 For structure II, where X is, for example,
CO ,, OCH SCH (R6) C02, CH2CH (C1) C02 or CH = C (Cl) C02.
90
Compounds II, or their sodium or potassium salts are reacted with one of the following reagents SOCl ,, (COCÍ) 2, C0C12, PClj or P0C13_ in a solvent, such as chloroform, dichloromethane, carbon tetrachloride, hexane, benzene , toluene, tetrahydrofuran, dioxane, aceton or methyl ethyl ketone, to supply an acid chloride This acid chloride is then reacted with intermediate III (optionally in the presence of bases, such as Et3N, pyridine, NaOH, KOH, Na2C03, K ^ C ^ NaHCO,) at a temperature from -40 ° C to the boiling point of the solvent, for 3 minutes to 8 hours to supply the final product I. The intermediate products V are prepared by known methods, for example see EP 0 567 82 Al.
Scheme 3 The preparation of the salts of formula I, for example, is direct, as shown: 91
The salts of the formula I can be prepared in ethanol or another solvent, with HCl, CHC02H, H3P04 / H02CC02H, etc. or other acids. The present invention will now be described, in greater detail, with reference to the Examples, in order to give an additional guidance to the practitioner. However, it should be understood that the present invention is not restricted to this specific Examples.
EXAMPLE OF PREPARATION A (Compound No. 15)
92
The 2- (4-chloro-2-fluoro-5-ethoxycarbonylmethoxy-phenyl) -4,5,6,7-tetrahydro-2H-isoindol-1,3-dione (4.0 g, obtained substantially by the methods described in EP 0 083 055 A2) and KOH (85%, 2.1 g) in 50 ml of ethanol, were stirred at room temperature for 1 hour and then evaporated to dryness. To the residue were added 100 ml of chloroform and 8 ml of SOCl2. The reaction mixture was then heated to reflux for 2 hours. The potassium chloride was filtered and washed with fresh chloroform. The filtrate was evaporated to dryness. To the residue were added 50 ml of chloroform and 1.5 g of 1-hydroxymethyl- (1H) -1,2,4-triazole. The reaction mixture was then stirred at room temperature for 5 hours. The water was added to the mixture, the organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography, to give 2.0 g of 2- (4-chloro-2-fluoro-5- [(1,2,4-triazolylmethoxy) -carbonylmethoxy] -phenyl) -4 , 5, 6, 7-tetrahydro-2H-isoindol-1,3-dione (Compound No. 15). Fusion Point of 151-154 ° C.
EXAMPLE OF PREPARATION B (Compound No. 43) 93
2 - (4-Chloro-2-fluoro-5-hydroxyphenyl) -4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (4.0 obtained substantially following the methods of EP 083 055 A2 ), K2C03 in 50 ml of the methyl ethyl ketone and 2.0 chloromethyl-1,2, -triazole hydrochloride, and then the mixture was heated to reflux for 5 hours. After cooling, the mixture was filtered and evaporated. Water and ethyl acetate were added to the residue. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography, to give 2.6 g of the 2- [4-chloro-2-fluoro-5-? (1, 2, 4-triazol-lH-yl) -methoxy] phenyl] -4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (Compound No. 43), as an oil. ^ NMR (CDClj): d 8.32 (s, 1H), 8.01 (s, 1H), 7.28 (d, 2H), 7.06 (d, 2H), 6.04 (s, 2H), 2.44 (bs, 4H), 2.83 (bs, 4H).
EXAMPLE OF PREPARATION C (Compound No. 1334) 94
To a suspension of 60% NaH (0.5 g) in 5 ml of N, N-? Imethylformamide, 0.8 g of 3- [4-chloro-2-fluoro-5-hydroxyphenyl] -6-trifluoromethyl-2 was added, 4-pyrimidione (obtained substantially following the methods of the patent EP 0 255 047 Al). After 10 minutes, 0.8 g of the chloromethyl-1,2,4-triazole hydrochloride was added and the mixture was heated in the 80 ° C bath for 8 hours. After cooling, the agu and ethyl acetate were added to the mixture. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 0.75 g of the 3- [4-chloro-2-fluoro-5- [(1, 2,4-triazol-1H-yl) -methoxy [phenyl]] -6-trifluoromethyl-2,4-pyrimidione (compound 1334), PF. 216-219 ° C. XH NMR (acetone-D6): 8.64 (s, 1H), 7.96 (s, 1H),
7. 55 Td, 2H), 7.52 (d, 2H), 6.36 (s, 1H), 6.27 (s, 2H). EXAMPLE OF PREPARATION D (Compound No. 1335) 95
To a suspension of 60% NaH (0.08 g) in 5 ml of the N, -dimethylformamide, 0.5 g of the 3- [4-chloro-2-fluoro-5- [(1,2,4-triazole) were added. -lH-yl) -methoxy [-phenyl] -6-trifluoromethyl-2,4-pyrimidione (compound 1334). After 10 minutes, 0.2 g of dimethyl sulfate was added and then the mixture was stirred at room temperature overnight. Water and ethyl acetate were added to the mixture. The organic layer was separated and washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography to give 0.2 g of l-methyl-3 - [4-chloro-2-fluoro-5- [1,2,4-triazol-lH-yl] -methoxy ] phenyl] -6-trifluoromethyl-2,4-pyrimidione (compound 1335). * H NMR (CDC13): 8.31 (s, 1H), 7.98 (s, 1H), 7.36 (d, 2H), 7.07 (d, 2H), 6.60 (s, 1H), 6.06 (s, 2H), 4.00 (s, 3H).
EXAMPLE OF PREPARATION E (Compound No. 1870) 96
2- [4-chloro-2-fluoro-5- [(1, 2,4-triazol-lH-yl) -methoxy] phenyl] -4,5,6,7-tetrahydro-2H-isoindol -1, 3 -dione (2.0 g) in hydrochloric acid (36%, 0.7 g) in 20 ml of ethanol was stirred for 10 minutes and then evaporated to dryness. To the residue was added 5 ml of acetone and the mixture was filtered and dried to obtain 1.6 g of the hydrochloride salt of 2- [4-chloro-2-fluoro-5- [(1, 2, 4-triazole-1H) -yl) methoxy] phenyl] -4,5,6,7-tetrahydro-2H-isoindole -1,3-dione (Compound 1870), as a solid. iH NMR (DMSO-DJ: 8.79 (s, 1H), 8.12 (s, 1H), 7.70
(d, 1H), 7.28 (d, 1H), 6.25 (s, 2H), 4.96 (s, 2H), 2.36 (bs, 4H), 1.75 (bs, 4H).
The compounds of the formula I are useful as active ingredients APRA herbicides. When the compound of the formula I of the present invention is used as a herbicide, this active ingredient can be used in a
suitable formulation, depending on the particular purposes and the appropriate application method. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and is used in a formulation such as a powder, a wettable powder, an emulsifiable concentrate, an aqueous or oil suspension, pellets, granules, etc. If convenient, a surfactant and / or other additive may also be added. Also, one of ordinary skill in the art will recognize that the compound of the present invention can be used in combination with an insecticide, a nematocide, a fungicide, other herbicides, an agent that controls the growth of plants, a fertilizer, etc. The compounds of the present invention can be used in the form of compositions or formulations. Examples of preparation of the compositions and formulations can be found in the American Chemical publication
Society, in "Research of Pesticide Formulations"
(1969). Advances in Chemistry Series No. 86, written by Wade Van Valkenburg and the publication of Marcel Dekker, Inc., "Formulations of Pesticides" (1973), edited by Wade Van Valkenburg. In these compositions and formulations, the 98
Active substances are mixed with conventional pesticide diluents, inert, agronomically acceptable (ie compatible with the plant and / or inertly pesticidally), such as a solid carrier material or a liquid carrier material, of the type that can be used in compositions or formulations conventional pesticides. By "agronomically acceptable carrier" is meant any substance that can be used to dissolve, disperse or diffuse the active ingredient in the composition, without harming the effectiveness of the active ingredient and which, by itself, does not have a significant detrimental effect to the soil , equipment, desired plants or agronomic environment. If desired, auxiliary agents, such as surfactants, stabilizers, antifoaming agents, anti-dripping agents, may also be combined. The compositions and formulations, according to the present invention, may also include known pesticidal compounds. This expands the spectrum of preparation activity and can lead to smergism. The formulations contain about 0.1 to 99% by weight of one or more active ingredients and at least one of (a) about 0.1% to 20% of agents 99
surfactants and (b) about 1 to 99.9% of one or more solid or liquid diluents. If the compound of formula (I) is combined with an additional herbicide, the concentration of one or more active ingredients in the compositions can vary within a wide range, depending on the active compound, the applications for which they are intended, environmental conditions and the formulation class. The concentration of one or more active ingredients in the compositions is generally between 1% and 95%, preferably between 5% and 60%. The formulations will now be described in detail with reference to examples of typical Formulations, and do not limit the scope of the invention. In the following Formulation Examples, "parts" mean "parts by weight". The number of the compound of the active ingredient corresponds to that in Tables 1 to 24.
Examples of Formulations la-c
Compound Nos, 1, 15 or 43 (all 50 parts), 5 parts of polyoxyethylene-alkylaryl ether, 5 parts of sodium dodecylbenzene and 40 parts of dioxide of 100
Synthetic hydrated silicon, mixed well, while being milled, in order to obtain a 50% wettable powder.
Formulation Example 2
Compound No. 35 (10 parts), 6 parts of polyoxyethylene alkylaryl ether, 4 parts of sodium dodecylbenzenesulfate, 30 parts of xylene and 50 parts of cyclohexanone, were mixed well, while being milled in order to obtain a concentrate. emulsifiable at 10% by weight.
Formulation Example 3
Compound No. 15 (20 parts), 2 parts of synthetic hydrated silicon dioxide, 3 parts of polyoxyethylene sorbitan monooleate, 5 parts of carboxymethylcellulose and 70 parts of water, were mixed well and pulverized until the size of particles of the active ingredient became less than 5 microns, in order to obtain a granulate at 20% by weight.
Formulation Example 4
Compound No. 15 (5 parts, 1 part of isopropyl acid phosphate, 64 parts of kaolin and 30 parts of 101
talc, they were mixed and pulverized well, up to a particle size of the active ingredient less than 5 microns, in order to obtain a powder at 5% by weight.
Formulation Example 5
Compound No. 15 (25 parts), 3 parts of polyoxyethylene sorbitan monooleate, 2 parts of polyvinyl alcohol and 70 parts of water, were mixed and pulverized well until the particle size of the active ingredient reached sex less than 5. microns, in order to obtain a 25% aqueous suspension.
The effective dose of the compounds of the present invention is usually within the range of 1 g / ha to 3 kg / ha, preferably 5 g / ha to 500 g / ha.
Biological Test The herbicidal activity of the compounds of the formula (I), with respect to weeds, such as
Bidens pilosa (cuscuta pilosa, BID), Solanum nígrum
(belladonna, NS), Polygonum lapathi folium (barbaasco, SMT),
Abutilon theophasti (hobby, VEL), were evaluated.
102
For each compound, the evaluation tests were carried out in accordance with the following operating procedures. For the pre-emergence tests, immediately after planting, the test compound was sprayed directly on the soil surface. The drawers or pots were placed in a greenhouse and then watered. For post-emergence tests, the seeds were allowed to germinate and grow for 10 to 21 days. Before the application, of each development series, the test plants were selected for uniformity, size and stage of development. The test plants were then treated with the test compound, returned to the greenhouse and watered. The plants not treated with the compound under evaluation, were used as a comparison. The compound to be evaluated was dissolved in a suitable solvent, usually acetone, or the formulation of the evaluated compounds was added to the water and sprayed on the boxes or pots using a volume of carrier equivalent to 187 or 468 liters per hectare , in the application regime in grams per hectare (g / ha). Around two or four weeks after the application of the 103
Test compounds, the state of the plant was observed. Each species was evaluated on a scale from 0 to 100, where 0 equals no activity and 100 equals total control. Some of the test results are shown in table 26.
Table 26
Compound Type g / ha BID NS SMT VEL
POST 150 60 100 40 100 43 POST 1200 100 100 100 100
Claims (8)
1. A compound represented by formula I wherein: R. is selected from H, F, Br, Cl, N02 and CN; R2 is selected from F, Cl, Br, H and CN; R3 is selected from H and CN; and alkyl, alkenyl, alkynyl haloalkyl, cycloalkyl, cycloalkenyl haloalkenyl, haloalkynyl, alkoxy, alkylthio alkylsulfonylalkyl, alkylsulfinylalkyl alkylsulfonylcycloalkyl, alkylsulfinylalkyl aryl, arylalkyl, heteroaryl heteroarylalkyl, all of which may be further substituted; R, and R5 are each independently selected from H halogen and CN; and alkyl, cycloalkyl haloalkyl, alkoxy, alkylthio, alkylsulfonyl 105 alkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, C02R6, CONR6R13, 0R6, SR6, S02R6, NR6R13, S02NR6R13, aryl, arylalkyl, heteroaryl and heteroarylalkyl, all of which may be further substituted; R6 is selected from H, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkyl sulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted; R7 is selected from H, alkyl, alkenyl, alkynyl, haloalkyl, cycloalkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl and C0Rs, all of which may be further substituted; Ra is selected from alkyl, haloalkyl, cycloalkyl, cycloalkenyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, aryl and arylalkyl, all of which may be further substituted, - 106 R9 is selected from H, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, alkenyl, alkynyl, haloalkyl and cycloalkyl, all of which may be further substituted; R10 is selected from H, halogen, NH2, alkyl, alkylsulfonylalkyl, alkylsulfinylalkyl, alkylsulfonylcycloalkyl, alkylsulfinylcycloalkyl, haloalkyl, CN, C02- (alkyl, CONH (alkyl); CON (alkyl) 2, wherein each alkyl may be the same or different, CH2CN, CH2CH = CH2, CH2C = CH, CH2C02 (alkyl), CH3OCH3 and CH _.- 1,2,4-triazole, all of which can be further substituted; RX1 is selected from H, CN, alkyl, haloalkyl and C02 ( alkyl); R12 is selected from H, alkyl, C02R6, CONR6R15, 0R6 SR6, S02R6, S02NR6R13 and NR6 R13, R13 is H, alkyl, aryl or aralkyl; A is? or CH; B is? or CR ^ -; Z is O, CH (R3), CO, CS, C0? R12 or CS? R12; 10 ' X is selected from O, S; NR12, C02, OCH (R6) C02, SCH (R6) C02, CH = C (halo) C02, CH2CH (halo) C02, CONH, OCH (R6) CONH, SCH (R6) CONH, CH = C (halo) CONH and CH2CH (halo) CONH, when Z is CH (R3); X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (halo) CO and CH2CH (halo) CO, when Z is 0; X is selected from O, S, CO, OCH (R6), CH = C (halo), CH_, CH (halo), CONH, OCH (Rs) CONH, SCH (R6) CONH, CH = (halo) CONH, CH2CH (halo) CONH and NR12, when Z is CO, CS, CONR12 or XCSNR12; and Q is selected from NR7COR6, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16, where Ql is 4, 5, 6, 7-tetrahydroftalimid-2-yl, Q2 is 5,6,7, 8-tetrahydro- 1, 2, 4 -triazolo [4, 3-a] -pyridin-3 (2H) -one-1-yl, Q3 is 5,6,7,8-tetrahydro-lH, 3H- [1,3,4] -thiadiazolo [3 , 5- a] iridazinimin-1-yl, Q4 is 4, 5, 6, 7-tetrahydroimidazo [1, 5-a] pyridin-1, 3- (2H.5H = -dione-1-yl, Q5 is 1 , 6, 8-triazabicyclo [, 3, 0] -nonano-7, 9-dion-8-yl, Q6 is 5- (1-methylethylene) -2,4-oxazolidindion-3-yl, Q7 is 5- ( 1,1-dimethylethyl) -1,4,4-oxadiazol-2 (3H) -in-3-yl, 108 Q8 is 4-difluoromethyl-4,5-dihydro-3-methyl-1,2,4-triazole-5- (1H) -one-1-yl, Q9 is 2-methyl-1,2,4-oxadiazolidin- 3, 5-dione-4-yl, Q10 is 4-chloro-l-methyl-5-difluoromethoxy-lH-pyrazol-3-yl, Qll is 4-bromo-l-methyl-5-trifluoromethyl-lH-pyrazole- 3-ilo, Q12 is 1-substituted-6-trifluoromethyl-2,4-pyrimidione-3-yl, Q13 is 1-substituted-6-trifluoromethyl-1,3,5-triazin-2, 4-dione-1-yl, Q14 is 4, 5-disubstituted-4,5-dihydro-l, 2, -triazin-3 (2H) -in-2-yl, Q15 is 4-substituted-l, 2,4-triazin-3, 5 (2H, 4H) -dione-2-yl, and Q16 is 5-methyl-6-oxo-4- (trifluoromethyl) -6H-pyridazin-1-yl. or its agronomically acceptable salts.
2. The compound of claim 1, wherein R? it is selected from H, F, Br, Cl, N02 and CN; R2 is selected from F, Cl, Br, H and CN; - is selected from H CN; and alkyl (C ^ C ^), cycloalkyl (C3-C8), alkenyl (C2-C12) cycloalkenyl (C3-Ca), alkynyl (C2-C12), haloalkyl [C ^ C12), haloalkenyl (C2-C12), haloalkynyl (C2-C12), alkoxy (Cj ^ -C ^), alkyl [C .. -C12) thio, alkyl (C_- 109) C12) sulfonylalkyl (CLC ^), alkyl (Cx-C12) sulfinylalkyl (Cx-C12), alkyl (CLC ^) sulfonyl-cycloalkyl (C3-C8), alkyl (Cx-C12) sulfinylalkyl (C3-C8), cyanoalkoxy ( C1-C12), cyanoalkyl [C-5 C12), cyanocycloalkyl (C3-C8), haloalkoxy (Cj ^ -C ^), haloalkyl (Cj-C- ^) thio, halocycloalkyl (C3-C8), aryl, heteroaryl, Arylalkyl (Cx-C12) and Hetroarylalkyl (C2-C12), all of which can be further substituted with one to three 10- substituents, independently selected from: bromine, chlorine, fluorine, alkyl (CLC ^), cycloalkyl (C3-C8), alkenyl (C2-C12), cycloalkenyl (C3-C8), alkynyl (C2-C12), haloalkyl [ C? -C12), haloalkenyl (C2-C12), Haloalkynyl (C2-C12), alkoxy (C1-C12), alkyl (Cx-C12) thio, alkyl (CJ ^ -C ^) sulfonyl, alkyl (Cj ^ - C12) sulfinyl, phenyl, phenalkyl [QX-CX2) , (C2-C12) phenalkenyl, (C2-C12) phenalkynyl, cyano, (Cx-C12) haloalkoxy, 1,3-dioxalan-2-yl and nitro; R4 and Rs are each independently selected from H, halogen and CN; and (C1-C12) alkyl, (C3-C8) cycloalkyl, haloalkyl (Cj ^ -C ^), (C1-C12) alkoxy, alkyl (Cx- not) C12) thio, [C1-C12 alkyl] sulfonylalkyl (CLC ^), alkyl sulfinylalkyl (C1-C12), alkyl [Cx- C12) sulfonylcycloalkyl (C3-C8), alkyl (Cx- C12) sulfinylcycloalkyl (Cj-Cg), cyanoalkoxy [C? - C12), cyanoalkyl (C ^ C ^), cyanocycloalkyl (C3-C8), haloalkoxy (C1-C12), haloalkyl (CLC ^) thio, halocycloalkyl (C3-C6), C02R6, CONHR6, CON ( alkyl (C, -C ^)) R6, OR6, SR6, S02R6, N (alkyl (C ^ C ^)) R6, S02N (alkyl (C ^ C ^)) R6, aryl, Heteroaryl, arylalkyl (Cj ^ -C ^), and heteroarylalkyl (C2-C12), all of which can be further substituted all of which can be further substituted with one to three substituents, selected 15 independently of: bromine, chlorine, fluorine, alkyl (C ^^ - C ^), cycloalkyl (C3-C8), alkenyl (C2-C12), cycloalkenyl (C3-C8), alkynyl (C2-C12), haloalkyl ( C1-C12), haloalkenyl (C2-C12), haloalkynyl (C2-C12), alkoxy (Cx-C12), alkyl (Cx- 20 C12) thio, alkyl (C ^ C. ^) sulfonyl, alkyl (Cj ^ - C12) sulfinyl, phenyl, phenalkyl (Cx-C12), 111 phenalkenyl (C2-C12), phenalkynyl (C2-C12), cyano, haloalkoxy [C .. -C12), 1,3-dioxalan-2-yl and nitro; R6 is selected from H, alkyl (Cx-C12), alkyl [C-C12) sulfonylalkyl (C ^ C ^), alkyl (C __-C12) sulfinylalkyl (C ^ C ^), alkyl [C-. - C12) sulfonylcycloalkyl (C3-C8), alkyl [C-C12) sulfinylcycloalkyl (C3-C8), cyanoalkoxy (Cj ^ -C ^), cyanoalkyl (Cx-C12), cyanocycloalkyl (C3-C8), haloalkoxy (Cj ^ C ^), haloalkyl [C .. C12) thio, halo (C3-C8) alkyl aryl and arylalkyl (CLC ^); R7 is selected from H, alkyl (Cj ^ -C ^), cycloalkyl (C3-C8), haloalkyl (C _-C12), alkyl (Cj ^ -C ^) sulfonyl- (C1-C12) alkyl, alkyl (CLC) - ^) sulfinylalkyl (Cx-C12), alkyl (C ^ C ^) sulfonylcycloalkyl (C3-C8), alkyl sulfinylcycloalkyl (C3-C8), cyanoalkoxy (CL-C12), cyanoalkyl (Cx-C12), cyanocycloalkyl (C3- C8) haloalkoxy (Cj ^ -C ^), haloalkyl (Cj ^ -C ^) thio, halocycloalkyl (C3-C8) and C0R8; R8 is selected from alkyl (C ^^ j), cycloalkyl (C3-C8), cycloalkenyl (C3-Ca) haloalkyl (Cj ^ -C ^), alkyl [C1-C12) sulfonylalkyl (C1-C12), alkyl (C) ^ 112 C12) sulfinylalkyl (C1-C12), alkyl (Cx-C12) sulfonylcyclalkyl (C3-Ca), alkyl (Cx-C12) sulfinylcycloalkyl (C3-C8), cyanoalkoxy (Cj ^ -C ^). cyanoalkyl (C ^ C ^), cyanocycloalkyl (C3-C8), haloalkoxy (Cj ^ -C ^), haloalkyl (C ^ C ^) thio, halocycloalkyl (C3-C8) aryl and arylalkyl (C-L-C ^); Rg is selected from H, alkyl (C ^^ - C ^) alkenyl (C ^ ^), cycloalkyl (C3-C8), haloalkyl (C1-CX2), alkyl [C ± - C12) sulfonylalkyl (C1-C12), alkyl (C ^ C. ^) sulfinyl- (Cx-C12) alkyl, (C1-C12) alkylsulfonyl-cycloalkyl (C3-C8), alkyl [C .. -C12) sulfinyl-cycloalkyl (C3-Ca), cyanoalkoxy (C1-C12), cyanoalkyl (Cj ^ -C ^), cyanocycloalkyl (C3-C8), haloalkoxy, haloalkyl (C1-C12) thio and halocycloalkyl (C3-C8); R. is selected from H, chloro, NH2, alkyl (CLC ^), haloalkyl (C ^ C ^), CN, alkyl (C ^ C ^) sulfonyl-alkyl (C ^ ^ - C ^), alkyl (CLC ^) ) sulfinylalkyl (Cx-C12), alkyl [C1-C12) sulfonylcycloalkyl (C3-C8), alkyl (Cj ^ -C ^) sulfinylcycloalkyl (C3-C8), haloalkyl, cyanoalkoxy (C ^ C. ^), cyanoalkyl (Cx) - C12). cyanocycloalkyl (Cj-Cg) haloalkoxy (Cx-C12) 113haloalkyl (C 1 -C 12) thio, halo (C 3 -C 8) alkyl, C 0 2 -alkyl (C 2 C 4), CONH-alkyl (C 2 C 4); WITH ((C1-Cl2) alkyl) 2, CH2CN, CH2 = CH2, CH2C = CH, CH2C02- (C1-C12) alkyl, CH2OCH3, CH2-1, 2,4-triazole; R1 is selected from H, CN, (C1-C12) alkyl, haloalkyl (Cx-C12) and C02- (C1-C12) alkyl; R12 is selected from H, alkyl, C02R6, CON (alkyl (Cx-C12)) R6, 0R6 SR6, S02R6 (S02N (alkyl (C.-C ,,)) and N (alkyl (CLC ^) R13, -R13 is H, alkyl (Cj ^ -C ^), aryl or aryl (C.-C12), A is N or CH, B is N or CR10, Z is O, CH (R3), CO, CS, CONR12 ÓCSNR12; X is selected from O, S, NR12, C02, OCH (Rs) C02, SCH (R6) C02, CH = C (C1) C02, CH2CH (C1) C02, CONH , OCH (R6) CONH, SCH (R6) CONH, CH = C (C1) C0NH and CH2CH (Cl) CONH, when Z is CH (R3); X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (Cl) CO and CH2CH (halo) CO, when Z is 0; X is selected from O, S, CO, 0CH (R6), CH = C (C1), C ^ CH (Cl), CONH, OCH (R5) CONH, SCH (Rs) CONH, 114 CH = (C1) C0NH, CH2CH (C1) CONH and NR12, when Z is CO, CS, CONR12 or CSNR12; and Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16, where or their agronomically acceptable salts.
3. The compound of claim 2, wherein R1 is H, F, or Cl; R2 is Cl; R3 is selected from H, bromine, chlorine, fluorine, alkyl (C ^ Cg), cycloalkyl (C3-C6 alkenyl (C2-C6) cycloalkenyl (C3-C8), alkynyl (C2-C6), haloalkyl [C-C6) , (C2-C6) haloalkenyl, (C2-C6) haloalkynyl, alkoxy (Ci-Cg) thio, aryl, heteroaryl, arylalkyl and (C2-C12) hetroarylalkyl, wherein the aryl or heteroaryl group is selected from furan, naphthalene , phenyl, pyrazole, pyridine, pyrimidine, thiophene, and triazole, and this aryl and heteroaryl group can be further substituted with one to three substituents, independently selected from: bromine, chlorine, fluorine, alkyl (C- ^ C ^), cycloalkyl (C3-Ca), alkenyl (C2-115) C12), (C3-C8) cycloalkenyl, (C2-C12) alkynyl, [Cx-C12) haloalkyl, (C2-C12) haloalkenyl, (C2-C12) haloalkynyl, (Cx-C12) alkoxy, [C-] alkyl. - C12) thio, (Cx-C12) alkylsulfonyl, (Cx-5C12 alkyl) sulfinyl, phenyl, phenalkyl (CLC ^), phenalkenyl (C2-C12), phenalkynyl (C2-C12), cyano, haloalkoxy (CLC ^) ), 1,3-dioxalan-2-yl and nitro; R4 and R5 are each independently selected from H, bromo, chloro, fluoro, CN; and alkyl, 10 (C3-C6) cycloalkyl, (C ^ C) alkoxy, (Cx-C6) alkoxy, alkyl (Ci-Cg) thio, C02R6, C0NHR6, CON (alkyl (C ^ C ,,,)) R6, 0R6, SR6 , S02R6, NHR6, N ((C ^ C ^) alkyl) R6, S02N ((C ^ C ^) alkyl) R6, aryl, heteroaryl, arylalkyl [C., -C12), and In the case of heteroarylalkyl (C2-C12), where the aryl or heteroaryl group is selected from furan, naphthalene, phenyl, pyrazole, pyridine, pyrimidine, thiophene and triazole, these aryl and heteroaryl groups can be further substituted with one to three 20 substituents, independently selected from: bromine, chlorine, fluorine, alkyl (C-L-C ^), cycloalkyl (C3-C8), alkenyl (C2-C12), cyclo-116 alkenyl (C3-C8), alkynyl (C2-C12), haloalkyl (Cx-C12), haloalkenyl (C2-C12), haloalkynyl (C2-C12), alkoxy (Cx-C12), alkyl [Cx- C12) thio, (C 1 -C 12) alkylsulfonyl, C 1 -C 12 alkylsulfinyl, phenyl, (C 1 -C 12) phenalkyl, (C 2 -C 2) phenalkenyl, (C 2 -C 12) phenalkynyl, cyano, haloalkoxy (CL 2), 1, 3- disxalan-2-yl and nitro; R6 is selected from H, (C1-C12) alkyl, aryl, and arylalkyl (C-L-C8), wherein the aryl group is naphthyl or phenyl; R7 is selected from H, alkyl (Cj ^ -C ^), cycloalkyl (C3-C8), haloalkyl, and COR6; R8 is selected from alkyl (Cx-C12), cycloalkyl (C3-C8), cycloalkenyl (C3-C8) haloalkyl (Cx-C12), aryl and arylalkyl (C ^ Cg); R9 is selected from H, alkyl (Cx-C6), alkenyl (Cx-C12), alkenyl (C2-C6) cycloalkyl (C3-Ca), cycloalkyl (C5-C6), haloalkyl (Cx-C12), haloalkyl (C ^ Cg); R10 is selected from H, chloro, NH2, alkyl (^ Cg), haloalkyl (C1-C12), haloalkyl (^ Cg), CN, C02- (Cx-C12) alkyl, CONH-alkyl (C ^ C ^), CON- (lkyloCi-CsJa, CH2CN, CH2CH = CH2, CH2C = CH2, CH2C02- alkylCjL-Ci;,) CH2OCH3, CH-1, 2,4-triazole; 117 R is selected from H, CN, alkyl (Cx-C6), haloalkyl (Cx-C12), haloalkyl 2-alkyl (Cx-C12); R12 is selected from H, al, C02R6, CON (C-C8 alkyl) R6, 0R6 SR6, S02R6r S02N (CX-CB alkyl) and N (Cj ^ -8 alkyl) R13; R13 is H, alkyl, where the aryl group is naphthyl or phenyl, A is N or CH, B is N or CR10, Z is O, CH (R3), CO, CS, CONR12 or CSNR12; X is selected from O, S, C02 , OCH (R6) C02, SCH (R6) C02, CH = C (C1) C02, CH2CH (C1) C02, CONH, OCH (R6) CONH, SCH (R6) CONH, CH = C (Cl) CONH and CH2CH (Cl) CONH, when Z is CH (R3); X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (C1) C0 and CH2CH (halo) CO, when Z is O; X is selected from O, S, CO, OCH (R6), CH = C (C1), CH2CH (C1), CONH, OCH (R5) CONH, SCH (R6) CONH, CH = (C1) C0NH, CH2CH (Cl) CONH and NR12, when Z is CO, CS, CONRx2 or CSNR12; and Q is selected from NR7COR8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16, where 118 or their agronomically acceptable salts, selected from those formed of hydrochloric acid, sulfuric acid, acetic acid, propionic acid, phosphoric acid and oxalic acid.
4. The compound of claim 3, wherein Rx is H, F or Cl; R2 is Cl; , R3 is selected from H, bromine, chlorine, fluorine, alkyl (C ^ Cg), cycloalkyl (C5-C6), alkenyl (C2-C6) cycloalkenyl (C3-C8), alkynyl (C2-C6), haloalkyl (Cx) - C6), haloalkenyl (C2-C6), haloalkynyl (C2-C6), haloalkynyl (C2-C6), alkoxy, alkyl [C1-Cs) thio, 3-furyl, 4-chloro-2-furyl, 5-chloro -2- furyl, 5-chloro-3-furyl, 2, 5-dichloeo-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4 - chlorophenyl, 4-trifluoromethylphenyl, bromophenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3- (1, 3-dioxolan-2-yl) phenyl, 2-fluorophenyl, 2-chlorophenyl, 2 - trifluoromethoxyphenyl, 3,5- 119 difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-chloro-phenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, 3,4,5-trifluorophenyl, 2-5-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3 -pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4- pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-dichloro-4-pyridyl, 2-thienyl, 3- thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3-thienyl; R4 and Rb are each independently selected from H, bromo, chloro, fluoro, CN; and alkyl, (C5-C6) cycloalkyl, haloalkyl, (CX-C6) alkoxy, (C1-C6) alkyl, C02R6, CONHR6, CON (CX-C6) alkyl, R6, OR6, SR6, S02R6, NHR6, 3- 20 furyl, 4-chloro-2-furyl, 5-chloro-2-furyl, 5- chloro-3-furyl, 2,5-dichloro-3-furyl, 1-naphthyl, 2-naphthyl, phenyl, -methylphenyl, 4-methoxyphenyl, 120 4 - . 4-Nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromo-phenyl, chlorophenyl, 3-fluoro-phenyl, 4-trifluoromethoxyphenyl, 4-cyanophenyl, 3- (1,3-dioxolan-2-yl) phenyl, -fluorophenyl, chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-chloro-phenyl, 3,4-difluorophenyl, 3-fluoro -5- 10 trifluoromethylphenyl, 3, 5-trifluorophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 6-chloro-2-pyridyl, 4,6-dichloro-2-pyridyl, 3-pyridyl, 5-bromo -3- pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 5-fluoro-3-pyridyl, 4-pyridyl, 2- 15-fluoro-4-pyridyl, 2-chloro-4- pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2, 6-dichloro-4-pyridyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl and 2,5-dichloro-3-thienyl; Rg is selected from H, alkyl, l-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitro- 121 phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 4-bromo-phenyl, 4-chlorophenyl, 3-fluorophenyl, 4-trifluoromethoxyphenyl, 4-cyano-phenyl, 3- (1,3-dioxolan-2-yl) phenyl , 2-fluoro-phenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3, 5-difluorophenyl, 3, 5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3, 4 -difluorophenyl, 3-fluoro-5-trifluoromethylphenyl and 3, 4, 5-trifluorophenyl; R7 is selected from H, alkyl, (C5-C6) cycloalkyl, haloalkyl (Ci-Cg), and COR9; R8 is selected from alkyl, (C3-C6) cycloalkyl, (C1-C12) haloalkyl, 1-naphthyl, 2-naphthyl, phenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, trifluoromethylphenyl, 4-bromo-phenyl, chlorophenyl, 3-fluoro-phenyl, trifluoromethoxyphenyl, 4-cyano-phenyl, 3- (1, 3-dioxolan-2-yl) phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl , 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3,5- 122 dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl and 3,4,5-trifluorophenyl; aryl and arylalkyl (C ^ Cg); R9 is selected from H, alkyl, alkenyl (Cx-C12), cycloalkyl (C5-C6) and haloalkyl (C ^ Cg); R10 is selected from H, chloro, NH2, alkyl (Cx-C8), haloalkyl (C -.- C, CN, C02- (C1-C6) alkyl, CONH- (Ci-Cg) alkyl, CON- (alkyl ( C1-C6) 2, CH2CN, CH2CH = CH2, CH2G = CH2, CH2C02-alkyl (Cx-C12) CH2OCH3, CH-1, 2,4-triazole; Rxl is selected from H, CN, alkyl and C02-alkyl (Cj ^ -C ^); R12 is selected from H, alkyl (C ^ Cg), C02-alkyl (Cx-C6), CON (alkyl (Ci-Cg)) 2, O-alkyl, S-alkyl (Cx-C6), S02- (C .-Cg), S02N- (alkyl (CL-Cg)) 2 and N (alkyl (C ^ Cg) 2. R13 is H, alkyl (Ci-Cg), aryl or aryl (C1-C4), where the group aryl is naphthyl or phenyl, A is N or CH, B is N or CR10, Z is O, CH (R3), CO, CS, C0NR12 or CSNR12; 123 X is selected from O, S, C02, OCH (R6) C02, SCH (R6) C02, CH = C (C1) C02, CH2CH (C1) C02, CONH, OCH (R6) CONH, SCH (R6) CONH, CH = C (Cl) CONH and CH2CH (Cl) CONH, when Z is CH (R3); X is selected from CO, OCH (R6) CO, SCH (R6) CO, CH = C (Cl) CO and CH2CH (C1) C0, when Z is O; X is selected from O, S, CO, OCH (R6), CH = C (C1), CH2CH (C1), CONH, OCH (Rs) CONH, SCH (R6) CONH, CH = (Cl) CONH, CH2CH ( Cl) CONH and NR12, when Z is CO, CS, C0NR12 or CSNR12; and Q is selected from NR7COR8, Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Qll, Q12, Q13, Q14, Q15 and Q16; or its agronomically acceptable salts, selected from those formed of hydrochloric acid, acetic acid, propionic acid, and oxalic acid.
5. A herbicidal composition, comprising a compound according to claims 1, 2, 3 or 4, and an agronomically acceptable carrier.
6. The composition of claim 5, which contains about 0.1% up to 99% by weight of said compound. 124
7. The composition of claim 6, further comprising a second pesticide or a fertilizer.
8. A method for controlling weeds, which comprises applying a herbicidally effective amount of a composition according to claim 5, and an agronomically acceptable carrier for weeds, to the site of the weeds to the growth medium of these weeds .
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60/139,152 | 1999-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA00005813A true MXPA00005813A (en) | 2002-07-25 |
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