CZ184599A3 - Methylem substituované fungicidy a artropodicidy - Google Patents
Methylem substituované fungicidy a artropodicidy Download PDFInfo
- Publication number
- CZ184599A3 CZ184599A3 CZ991845A CZ184599A CZ184599A3 CZ 184599 A3 CZ184599 A3 CZ 184599A3 CZ 991845 A CZ991845 A CZ 991845A CZ 184599 A CZ184599 A CZ 184599A CZ 184599 A3 CZ184599 A3 CZ 184599A3
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- carbon
- atoms
- methyl
- optionally substituted
- Prior art date
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 65
- 230000000855 fungicidal effect Effects 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 315
- 238000000034 method Methods 0.000 claims abstract description 95
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 241000238421 Arthropoda Species 0.000 claims abstract description 21
- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 7
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 139
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 120
- 229910052799 carbon Inorganic materials 0.000 claims description 103
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 89
- 125000004429 atom Chemical group 0.000 claims description 85
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 66
- 125000001188 haloalkyl group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 241000196324 Embryophyta Species 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 239000007787 solid Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims 1
- XAGZJIQIVXSURR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]piperidin-2-one Chemical group C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCCC1 XAGZJIQIVXSURR-UHFFFAOYSA-N 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract description 11
- 238000006243 chemical reaction Methods 0.000 description 111
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- 239000000460 chlorine Substances 0.000 description 61
- 238000012360 testing method Methods 0.000 description 58
- 239000002585 base Substances 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 28
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 28
- 229940126142 compound 16 Drugs 0.000 description 28
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 27
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 229940126543 compound 14 Drugs 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 26
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229910052740 iodine Inorganic materials 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 235000019198 oils Nutrition 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 229910052794 bromium Inorganic materials 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000725 suspension Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 241000607479 Yersinia pestis Species 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000006722 reduction reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 11
- 239000012038 nucleophile Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 10
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 9
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 9
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 9
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 9
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000005730 Azoxystrobin Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 9
- 239000005756 Cymoxanil Substances 0.000 description 9
- 239000005757 Cyproconazole Substances 0.000 description 9
- 239000005758 Cyprodinil Substances 0.000 description 9
- 239000005767 Epoxiconazole Substances 0.000 description 9
- 239000005772 Famoxadone Substances 0.000 description 9
- 239000005778 Fenpropimorph Substances 0.000 description 9
- 239000005786 Flutolanil Substances 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000005800 Kresoxim-methyl Substances 0.000 description 9
- 239000005802 Mancozeb Substances 0.000 description 9
- 239000005807 Metalaxyl Substances 0.000 description 9
- 239000005814 Pencycuron Substances 0.000 description 9
- 239000005822 Propiconazole Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229930195482 Validamycin Natural products 0.000 description 9
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 9
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 9
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 9
- 239000006013 carbendazim Substances 0.000 description 9
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000001879 copper Chemical class 0.000 description 9
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 9
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 9
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 9
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 9
- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 9
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 9
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 9
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
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- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Description
Oblast techniky
Vynález se týká určitých methylem substituovaných fungicidů, jejich N-oxidů, zemědělsky vhodných solí a kompozic, a způsobů jejich použití jako . fungicidů a arthropodicidů.
Dosavadní stav techniky
Pro dosažení vysoké efektivity sklizně je velmi důležité kontrolovat choroby rostlin způsobené fungálními rostlinnými patogeny. Rostlinné choroby na okrasných rostlinách, zelenině, polních plodinách, cereáliích a ovoci mohou podstatným způsobem snížit produkci těchto rostlin, což má zase za následek zvýšení cen pro spotřebitele. Kontrola arthropodních škůdců je rovněž velmi důležitým krokem pro dosažení vysoké účinnosti sklizně. Škody, způsobené členovci na rostoucí a skladované zemědělské sklizni, mohou způsobit podstatné snížení produktivity a výsledkem může být opět zvýšení ceny zemědělských produktů pro spotřebitele. Kontrola arthropodních škůdců prováděná v lesích, u plodin pěstovaných ve sklenících, u okrasných rostlin, v pěstitelských školkách, u skladovaných potravinových a vláknitých produktů, u hospodářských zvířat, v domácnostech, u lidí a u zvířat je rovněž velmi důležitá. Pro tyto účely trh nabízí celou řadu komerčně dostupných produktů, ale stále existuje potřeba vyvíjet nové sloučeniny, které by byly v tomto ohledu účinnější,
01-859-99 Če lacinější, méně toxické a šetrnější k životnímu prostředí, nebo sloučeniny, které by kontrolu zajišťovaly odlišným způsobem.
Mezinárodní publikace WO 95/14009, WO 96/26190, WO 96/38425, WO 97/00612 a evropská patentová přihláška EP-A-178,826 a EP-A-226,917 popisují některé konkrétní methylem substituované fungicidy.
Podstata vynálezu
Vynález zahrnuje sloučeniny obecného vzorce I včetně všech jejich geometrických stereoisomerů, W-oxidů a zemědělsky vhodných solí:
ve kterém
T znamená
COOR5
T2
X-
01-859-99 Če
RlO ^bT^COOR5
TJ nebo
X znamená OR1, SÍOJ^R1 nebo atom halogenu;
A znamená atom kyslíku, atom síry, atom dusíku, NR5 nebo
CR7;
G znamená atom uhlíku nebo atom dusíku, za předpokladu že pokud G znamená atom uhlíku, potom A znamená atom kyslíku, atom síry nebo NR5 a pohyblivá dvojná vazba je navázána na G, pokud však G znamená atom dusíku, potom A znamená atom dusíku nebo CR7 a pohyblivá dvojná vazba je navázána na A;
W znamená atom kyslíku, atom síry, aminoskupinu, N-alkylovou skupinu s 1 až 6 atomy uhlíku, nebo NO-alkylovou skupinu s 1 až 6 atomy uhlíku;
Y znamená -0-, -CH2O-, -OCH2-, -CHR110-N=C (R8)-, přímou vazbu, -(CH2)e-, -C(R11)=C(R11)-, -CH2S(O)n-, -C(R8)=N-OCHR11-, -CHR11SC(R8)=N-, -C (R11)=N-N=C (R11) -CHR11O-N=C(R8)CH2S-, -CHR11O-N=C(R8)CH2O-, -C(R11)=N-N(CH3)-,
-CHRX1OC- (R8)=N-, -CHR^OC (=S)NR11-, -CHR^SC (=S) NR11-, -SCHR11- nebo -CHR110N=C (R11) C (=N-0R11)-; a nasměrování vazby Y je definováno tak, že část znázorněná na levé straně vazby je navázána na fenylový kruh, který má R3 a R4 substituenty, a část na pravé straně vazby je navázána na Z;
Z se nezávisle zvolí z:
• ·
01-859-99 Če
i) alkylové skupiny s 1 až 10 atomy uhlíku, halogenoalkylové skupiny s 1 až 10 atomy uhlíku nebo fenylové skupiny, přičemž všechny tyto skupiny mohou být případně substituovány R9 a případně substituovány jedním nebo více substituenty R10;
ii) pěti- nebo šestičlenného aromatického heterocyklického kruhu, přičemž každý heterocyklický kruh obsahuje 1 až 4 heteroatomy nezávisle zvolené z množiny zahrnující atom dusíku, atom kyslíku a atom síry, za předpokladu, že každý heterocyklický kruh neobsahuje více než 3 atomy dusíku, více než 1 atom kyslíku a více než 1 atom síry, přičemž každý aromatický heterocyklický kruh je případně substituován R9 a případně substituován jedním nebo více R10;
iii) naftalenového kruhu případně substituovaného R9 a případně substituovaného jedním nebo více R10; a iv) tetrahydronaftalenového kruhu ného R9 a případně substituovaného případně substituovajedním nebo více R10;
R1 znamená alkylovou skupinu s halogenoalkylovou skupinu s alkenylovou skupinu se 2 halogenoalkenylovou skupinu se alkinylovou skupinu se 2 halogenoalkinylovou skupinu se cykloalkylovou skupinu se 3 alkylkarbonylovou skupinu se 2 alkoxykarbonylovou skupinu se 2
1 | až 6 | atomy | uhlíku |
1 | až 6 | atomy | uhlíku |
až | 6 | atomy | uhlíku |
2 | až 6 | atomy | uhlíku |
až | 6 | atomy | uhlíku |
2 | až 6 | atomy | uhlíku |
až 6 | atomy | uhlíku |
až 4 atomy uhlíku nebo až 4 atomy uhlíku;
R2 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku,
01-859-99 Če
alkenylovou skupinu se | 2 | až 6 | atomy | uhlíku, |
halogenoalkenylovou skupinu | se | 2 až 6 | atomy | uhlíku, |
alkinylovou skupinu se | 2 | až 6 | atomy | uhlíku, |
halogenoalkinylovou skupinu | se | 2 až 6 | atomy | uhlíku, |
cykloalkylovou skupinu se | 3 | až 6 | atomy | uhlíku, |
alkylkarbonylovou skupinu | se | 2 až 4 | atomy | uhlíku, |
alkoxykarbonylovou skupinu | se | 2 až 4 | atomy | uhlíku, |
hydroxyskupinu, alkoxyskupinu s | 1 až 2 atomy uhlíku nebo |
acetyloxyskupinu;
R3 a R4 každý nezávisle znamenají atom vodíku, nebo methylovou skupinu za předpokladu, že R3 a R4 oba neznamenají atom vodíku;
R5 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy
uhlíku, halogenoalkylovou skupinu s | 1 až | 6 atomy | uhlíku, | |
alkenylovou skupinu se 2 | až | 6 | atomy | uhlíku, |
halogenoalkenylovou skupinu se | 2 | až 6 | atomy | uhlíku, |
alkinylovou skupinu se 2 | až | 6 | atomy | uhlíku, |
halogenoalkinylovou skupinu se | 2 | až 6 | atomy | uhlíku, |
cykloalkylovou skupinu se 3 | až | 6 | atomy | uhlíku, |
alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku nebo alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku;
Rs znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy
uhlíku, halogenoalkylovou skupinu s | 1 až | 6 atomy | uhlíku, | ||
alkenylovou skupinu se | 2 | až | 6 | atomy | uhlíku, |
halogenoalkenylovou skupinu | se | 2 | až 6 | atomy | uhlíku, |
alkinylovou skupinu se | 2 | až | 6 | atomy | uhlíku, |
halogenoalkinylovou skupinu | se | 2 | až 6 | atomy | uhlíku, |
cykloalkylovou skupinu se | 3 | až 6 | atomy | uhlíku, | |
alkylkarbonylovou skupinu | se | 2 | až 4 | atomy | uhlíku, |
alkoxykarbonylovou skupinu | se | 2 | až 4 | atomy | uhlíku, |
01-859-99 Če
hydroxyskupinu, alkoxyskupinu s 1 až 2 atomy uhlíku nebo acetyloxyskupinu;
R7 znamená atom vodíku, atom halogenu nebo methylovou skupinu;
R8 znamená atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku, alkoxyskupinu s 1 až 3 atomy uhlíku, alkylthioskupinu s 1 až 3 atomy uhlíku, halogenoalkylovou skupinu s 1 až 3 atomy uhlíku, alkenylovou skupinu se 2 až 3 atomy uhlíku, alkinylovou skupinu se 2 až 3 atomy uhlíku, cyklopropylovou skupinu, kyanoskupinu nebo aminoskupinu;
R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, alkylthioskupinu s 1 až 6 atomy
uhlíku, halogenoalkylthioskupinu | s 1 | až | 6 atomy | uhlíku, |
alkylsulfinylovou skupinu s 1 | až | 6 | atomy | uhlíku, |
alkylsulfonylovou skupinu s 1 | až | 6 | atomy | uhlíku, |
cykloalkylovou skupinu se 3 | až | 6 | atomy | uhlíku, |
trimethylsilylovou skupinu, alkinylovou | skupinu | se 2 až |
atomy uhlíku substituovanou trimethylsilylovou skupinou nebo cykloalkylovou skupinou se 3 až 6 atomy uhlíku, nebo fenylovou skupinu nebo fenoxyskupinu, přičemž každá fenylová skupina nebo fenoxyskupina může být případně substituována R12 a případně jedním nebo více R13 za předpokladu, že pokud R9 znamená fenylovou skupinu nebo fenoxyskupinu, která je případně která • ·
01-859-99 Če
substituována R12 a případně substituována jedním nebo několika R13, potom T neznamená T1;
R10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu; nebo
R9 a R10 pokud jsou navázány na sousedící atomy uhlíku, potom mohou společně tvořit -CH2CH20- nebo -OCH2CH2O-;
každý R11 znamená nezávisle atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku nebo cyklopropylovou skupinu;
R znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, alkylthioskupinu s 1 až 6 atomy uhlíku, halogenoalkylthioskupinu s 1 až 6 atomy uhlíku, alkylsulfinylovou skupinu s 1 až 6 atomy uhlíku, alkylsulfonylovou skupinu s 1 až 6 atomy uhlíku nebo cykloalkylovou skupinu se 3 až 6 atomy uhlíku;
R13 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu;
m znamená 0, 1 nebo 2;
n znamená 0, 1, nebo 2;
01-859-99 Če r znamená 1, 2, 3 nebo 4; a s znamená 0 nebo 1.
Vynález dále poskytuje způsob kontroly členovců, který zahrnuje uvedení členovců nebo jejich životního prostředí do kontaktu s arthropodicidně účinným množstvím sloučeniny obecného vzorce I, který zahrnuje všechny její geometrické isomery a stereoisomery, N-oxid a zemědělsky vhodné soli za předpokladu, že pokud T znamená T1, potom
i) pokud Y znamená -Ο-, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 6-chloro-4-pyrimidinylovou skupinu a 6-chloro2-pyrazinylovou skupinu;
ii) pokud Y znamená přímou vazbu, X znamená atom chloru, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená CH2Br;
iii) pokud Y znamená -0- a Z znamená 1,2,4-thiadiazol-5ylovou skupinu nebo 2-thiazolylovou skupinu případně substituovanou R9 a případně substituovanou R10, potom ani R9 ani R10 neznamená C(CH3)3; a iv) Y-Z neznamená alkylovou skupinu s 1 až 10 atomy uhlíku a alkoxyskupinu s 1 až 10 atomy uhlíku.
Vynález rovněž poskytuje vybrané sloučeniny obecného vzorce I, které jsou považovány za zvláště účinné fungicidy a arthropodicidy. Konkrétně tento vynález poskytuje sloučeniny obecného vzorce I, které zahrnují rovněž všechny jejich geometrické isomery a stereoisomery, N-oxidy a zemědělsky vhodné soli, zemědělské kompozice obsahující • · ·
01-859-99 Če tyto sloučeniny, a jejich použití jako fungicidy a arthropodicidy za předpokladu, že (a) pokud T znamená T1, potom
i) pokud Y znamená -0-, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 6-chloro-4-pyrimidinylovou skupinu a 6-chloro-2-pyrazinylovou skupinu;
ii) pokud Y znamená přímou vazbu, X znamená atom chloru, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená CH2Br;
iii) pokud Y znamená -0- a Z znamená 1,2,4thiadiazol-5-ylovou skupinu nebo 2-thiazolylovou skupinu případně substituovanou R9 a případně substituovanou R10, potom ani R9 ani R10 neznamená C(CH3)3;
iv) Y-Z neznamená alkylovou skupinu s 1 až 10 atomy uhlíku a aíkoxyskupinu s 1 až 10 atomy uhlíku;
v) pokud Y znamená -CH2O-N=C (CH3) -, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 3-(trifluoromethyl)fenyl;
vi) pokud Y znamená -CH20-N=C (CH3)-, X znamená OMe, R3 znamená atom vodíku a R4 znamená methylovou skupinu, potom Z neznamená 3(trifluoromethyl)fenyl;
01-859-99 Če vii) pokud Z znamená 2-naftalenylovou skupinu nebo 5,6,7,8-tetrahydro-2-naftalenylovou skupinu, potom Y neznamená -CH2O- a -CH2O-N=C (CH3)-;
viii) pokud Y znamená -CH2O-, R3 znamená methylovou skupinu, Z znamená fenylovou skupinu substituovanou R9 v poloze 2 a R9 znamená methylovou skupinu nebo atom halogenu, potom je Z substituován alespoň jedním R10, který neznamená methylovou skupinu a halogen; a ix) pokud Y znamená -CH2O-, R3 znamená methylovou skupinu, Z znamená fenylovou skupinu substituovanou R10 v poloze 2 a R10 znamená methylovou skupinu nebo atom halogenu, potom je Z substituován alespoň jedním R9 nebo R10, kterým není methylová skupina a atom halogenu;
(b) pokud T znamená T2, potom
i) Y neznamená -0CH2-, -C (R11) =C (R11) - a -SCHR11-;
ii) pokud Y znamená -O- nebo -(CH2)X-, potom Z znamená pyrimidinylovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo několika R10;
iii) pokud Y znamená -CH2O-, potom Z znamená pyridinylovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo několika R10; a iv) pokud Y znamená -CH20-N=C (CH3) potom s znamená 1;
• · • · • · | • · · ···· ·· ·· • · ·· · ««·· • ··· · Ě. - * | |
01-859-99 | V · · Ce · · | • ·· · · · ··« ··· • · · · · · |
• · | ··· ·· · ·· ·· | |
11 | ||
(c) pokud | T znamená T3, potom | |
i) Y neznamená -SCHR11-; a | ||
ii) pokud Y znamená -CH20-, | potom Z znamená |
fenýlovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo několika R10; a (d) pokud T znamená T4, potom
i) Y neznamená -C (R11) =C (R11) - a -CH2S(O)n-; a ii) pokud Y znamená -CH2O-, potom Z znamená fenýlovou skupinu nebo naftalenylovou skupinu, přičemž každá může být případně substituována R9 a případně substituována jedním nebo více R10.
Ve výše uvedeném textu výraz „alkylová skupina, použitý ve skupinách „alkylthioskupina, „halogenoalkylthioskupina, „alkylsulfinylová a „alkylsulfonylová zahrnuje alkylovou skupinu s přímým nebo větveným řetězcem, například methylovou skupinu, ethylovou skupinu, n-propylovou skupinu, i-propylovou skupinu nebo různé butylové, pentylové nebo hexylové isomery. Výraz „alkylová skupina, použitý samotný nebo ve výrazu „halogenoalkylová skupina zahrnuje alkylovou skupinu s přímým nebo větveným řetězcem, jako například methylovou skupinu, ethylovou skupinu, n-propylovou skupinu, i-propylovou skupinu nebo různé butylové, pentylové, hexylové, heptylové, oktylové, nonylové a decylové isomery. Výraz „alkenylová skupina, jak je zde uveden, zahrnuje alkeny s přímým nebo větveným řetězcem, jako například vinylovou skupinu, 1-propenylovou
01-859-99 Ce různé butenylové, Výraz „alkenylová skupinu, 2-propenylovou skupinu a pentenylové a hexenylové isomery.
skupina, jak je zde uveden, rovněž zahrnuje polyeny, jako například 1, 2-propadienylovou a 2,4-hexadienylovou skupinu. Výraz „alkinylová skupina, jak je zde uveden, zahrnuje alkiny s přímým nebo větveným řetězcem, jako například ethinylovou skupinu, 1-propinylovou skupinu, 2-propinylovou skupinu, a různé butinylové, pentinylové a hexinylové isomery. Výraz „alkinylová skupina, jak je' zde uveden, rovněž zahrnuje zbytky zahrnující více trojných vazeb, například 2,5-hexadiinyl.
Výraz „alkoxyskupina, jak je zde uveden, zahrnuje například methoxyskupinu, ethoxyskupinu, n-propyloxyskupinu, isopropyloxyskupinu a různé butoxy-, pentoxy- a hexyloxyisomery. Výraz „álkylthioskupina, jak je zde uveden, zahrnuje alkylthioskupiny s větveným nebo přímým řetězcem, jako například methylthioskupinu, ethylthioskupinu a různé propylthio-, butylthio-, pentylthio- a hexylthioisomery. Výraz „alkylsulfinylová skupina, jak je zde uveden, zahrnuje oba enantiomery alkylsulfinylové skupiny. Příklady „alkysulfinylové skupiny zahrnují například CH3S(O), CH3CH2S(O), CH3CH2CH2S (0) , (CH3)2CHS(O) a různé butylsulfinylové, pentylsulfinylové a hexylsulfinylové isomery. Příklady „alkylsulfonylových skupin zahrnují CH3S(O)2, CH3CH2S(0)2,
CH3CH2CH2S (0) 2, (CH3) 2CHS (0) 2 a různé butylsulfonylové, pentylsulfonylové a hexylsulfonylové „cykloalkylová skupina, jak je zde například cyklopropylovou skupinu, cyklobutylovou skupinu, cyklopentylovou skupinu a cyklohexylovou skupinu.
isomery. Výraz uveden, zahrnuje
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Výraz „halogen, buď samotný nebo ve výrazu „halogenoalkylová skupina, jak je zde uveden, zahrnuje fluor, chlor, brom nebo jod. Kromě toho, pokud se použije ve výrazu jako je například „halogenoalkylová skupina, potom může být uvedený alkylový zbytek částečně nebo zcela substituován atomy halogenu, které mohou být stejné nebo různé. Příklady „halogenoalkylových skupin zahrnují F3C, C1CH2, CF3CH2 a CF3CCI2. Výrazy „halogenoalkenylová skupina, „halogenoalkinylová skupina, halogenoalkoxyskupina, „halogenothioskupina apod., jak jsou zde uvedeny, jsou definovány analogicky s výrazem „halogenoalkylová skupina. Příklady „halogenoalkenylových skupin zahrnují (C1)2C=CHCH2 a CF3CH2CH=CHCH2. Příklady „halogenoalkinylových skupin zahrnují HC=CCHC1, CF3C=C, CCl3CsC a FCH2C=CCH2. Příklady „halogenoalkoxyskupin zahrnují CF3O, CCI3CH2O, HCF2CH2CH20 a CF3CH2O. Příklady „halogenoalkylthioskupin zahrnují CC13S, CF3S, CC13CH2S a CICH2CH2CH2S.
„Aromatické heterocyklické kruhy, jak jsou zde uvedeny, jsou zde definovány jako kruhy, které splňují Huckelovo pravidlo. Příklady zahrnují: pětičlenný a šestičlenný aromatický heterocyklický kruh obsahující 1 až 4 heteroatomy, například furanyl, furazanyl, thienyl, pyrrolyl, parazolyl, oxazolyl, oxadiazolyl, imidazolyl, isoxazolyl, thiazolyl, thiadiazolyl, isothiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl a triazinyl, přičemž uvedený kruh je navázán přes libovolný atom uhlíku nebo dusíku, který je k dispozici. Pokud je například aromatickým heterocyklickým kruhem furanyl, potom jím může být 2-furanyl nebo 3-furanyl. V případě pyrrolylu může být aromatickým heterocyklickým kruhem 1-pyrrolyl, 2-pyrrolyl nebo 3-pyrrolyl a v případě pyridylu může být aromatickým • · • f » i ···* * · · » · « « oi-859-99 če ·· J»» ·· · · · * « kruhem 2-pyridyl, 3-pyridyl nebo 4-pyridyl a totéž platí i pro ostatní aromatické heterocyklické kruhy.
Pokud Z znamená tetrahydronaftalenový kruh případně substituovaný R9 a případně substituovaný jedním nebo více R10, potom je substituent Y výhodně navázán na aromatický kruh tetrahydronaftalenu (tj. kruh, který splňuje Huckelovo pravidlo).
Celkový počet uhlíkových atomů v substituční skupině je označen předponou „Ci-Cj, ve které i a j znamenají čísla od 1 do 10. Například Ci~C3alkylthioskupina označuje methylthioskupinu až propylthioskupinu. Příklady „alkylkarbonylových skupin zahrnují C(O)CH3, C(0)CH2CH2CH3 a C(0)CH(CH3) 2 · Příklady „alkoxykarbonylových skupin zahrnují CH30C(=0), CH3CH2OC (=0) , CH3CH2CH2OC (=0) a (CH3) 2CH0C(=0) . „Acetyloxyskupina označuje CH30(=0)0.
Pokud skupina obsahuje substituent, kterým může být atom vodíku, například R2 nebo R7, potom pokud se zvolí tento substituent, lze uvedenou skupinu považovat za ekvivalent nesubstituované skupiny. Pokud je skupina případně substituována substituentem, například R1, potom pokud není tato skupina substituována substituentem, může být považována za ekvivalent skupiny, kde je substituentem atom vodíku.
Sloučeniny podle vynálezu mohou existovat jako jeden nebo více stereoisomerů. Různé stereoisomery zahrnují enantiomery, diastereomery, atropisomery a geometrické isomery. Odborník v daném oboru ví, že jeden stereoisomer může být účinnější a/nebo může mít prospěšné účinky, pokud bude jeho koncentrace v porovnání s dalším stereoisomerem (stereoisomery) vyšší nebo pokud se od ostatních
Β Β ·
Β · * · • · · · >
* · »
01-859-99 Če ·· *·«Μ λ · Β < · » β Β • » ·
Β Β · • » · · » » · <Ρ » « < « ί 4 « • · • Β · β stereoisomerů zcela izoluje. (Viz např. patentová přihláška US [Docket No. BA-9183-P1] , podaná 4. září 1997). Kromě toho umí odborník v daném oboru uvedené stereoisomery separovat, obohatit a/nebo selektivně připravit. Z výše uvedeného vyplývá, že vynález zahrnuje sloučeniny zvolené ze sloučenin obecného vzorce I a jejich zemědělsky vhodné soli. Sloučeniny podle vynálezu mohou být přítomny ve formě směsi stereoisomerů, jednotlivých stereoisomerů nebo jako opticky aktivní formy.
Soli sloučenin podle vynálezu zahrnují kyselinové adiční soli s anorganickými nebo organickými kyselinami, například kyselinou bromovodíkovou, kyselinou chlorovodíkovou, kyselinou dusičnou, kyselinou fosforečnou, kyselinou sírovou, kyselinou octovou, kyselinou butyrovou, kyselinou fumarovou, kyselinou mléčnou, malonovou, kyselinou maleinovou, kyselinou kyselinou propionovou, kyselinou salicylovou, vinnou, kyselinou 4-toluensulfonovou nebo valerovou.
kyselinou oxalovou, kyselinou kyselinou
Výhodnými sloučeninami pro tyto účely, které mají lepší účinnost a/nebo které se snadno syntetizují jsou následující „výhodné sloučeniny 1 až 5.
Výhodné sloučeniny 1
Sloučeniny výše uvedeného obecného vzorce I a jejich zemědělsky vhodné soli, ve kterých:
T znamená T1;
A znamená atom dusíku;
·· ···· • · » » « fe ·
01-859-99 Če » * · ··
G znamená atom dusíku;
Y znamená -O-;
Z znamená fenylovou skupinu, pyridinylovou skupinu, thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;
R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; a
R10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku;
za předpokladu, že pokud Z znamená 1,2,4-thiadiazol-5ylovou skupinu nebo 2-thiazolylovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo více R10, potom ani R9 ani R10 neznamenají C(CH3)3.
Výhodné sloučeniny 2
Sloučeniny výše uvedeného obecného vzorce I a jejich zemědělsky vhodné soli, ve kterých:
T znamená T1;
A znamená atom dusíku;
G znamená atom dusíku;
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Y znamená -CH2O-;
Z znamená fenylovou skupinu, pyridinylovou skupinu, thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;
R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; a
R10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku;
za předpokladu, že
i) pokud R3 znamená methylovou skupinu a Z znamená fenylovou skupinu substituovanou R9 v poloze 2 a R9 znamená methylovou skupinu nebo atom halogenu, potom je Z substituován alespoň jedním substituentem R10, který je jiný než methylová skupina a atom halogenu;
a ii) pokud R3 znamená methylovou skupinu a Z znamená fenylovou skupinu substituovanou R10 v poloze 2 a R10 znamená methylovou skupinu nebo atom halogenu, potom je Z substituován alespoň jedním substituentem R9 nebo R10, který je jiný než methylová skupina a atom halogenu.
• · « ·
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Výhodné sloučeniny 3
Sloučeniny výše uvedeného obecného vzorce I a jejich zemědělsky vhodné soli, ve kterých:
T znamená
A znamená
G znamená
Y znamená
T1;
atom dusíku;
atom dusíku;
-CH20-N=C(R8) - ;
Z znamená fenylovou skupinu, pyridinylovou skupinu, thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;
R8 znamená methylovou skupinu;
R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; a
R10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku;
za předpokladu, že
i) pokud X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená
3-(trifluoromethyl)fenylovou skupinu; a
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ii) pokud X znamená OMe, R3 znamená atom vodíku a R4 znamená methylovou skupinu, potom Z neznamená 3-(trifluoromethyl)fenylovou skupinu.
Výhodné sloučeniny 4
Sloučeniny výše uvedeného obecného vzorce I a jejich zemědělsky vhodné soli, ve kterých:
T znamená T1;
A znamená atom dusíku;
G znamená atom dusíku;
Y znamená -0-, -CH2O- nebo -CH20-N=C (R8)-;
Z znamená thienyl případně substituovaný R9 a případně substituovaný jedním nebo více R10;
R8 znamená methylovou skupinu;
R9 znamená atom halogenu nebo alkylovou skupinu s 1 až 3 atomy uhlíku; a
R10 znamená atom halogenu nebo alkylovou skupinu s 1 až 3 atomy uhlíku.
Výhodné sloučeniny 5
Výhodné sloučeniny 4, ve kterých Y znamená -0-.
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Nejvýhodnějšími sloučeninami podle vynálezu jsou sloučeniny zvolené ze skupiny zahrnující:
4-[2-(3-fluorofenoxy)-6-methylfenyl]-2,4-dihydro-5methoxy-2-methyl-3íř-lz 2,4-triazol-3-on;
2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(3methylfenoxy)fenyl]-3H-1,2,4-triazol-3-on;
2.4- dihydro-5-methoxy-2-methyl-4-(2-methyl-6fenoxyfenyl) -3íf-l, 2,4-triazol-3-on;
2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(4methylfenoxy)fenyl]-3H-1,2,4-triazol-3-on;
2.4- dihydro-5-methoxy-2-methyl-4-[6-methyl-2-[3(trifluoromethyl)fenoxy]fenyl]-3H-1,2,4-triazol-3on;
2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-[ [ [ [1-[4(trifluoromethyl)-2-pyridinyl]ethyliden]amino]oxy]methyl]fenyl]-3/7-1,2, 4-triazol-3-on;
4-[2-[[[[1-[2-fluoro-5-(trifluoromethyl)fenyl]ethyliden] amino]oxy]methyl]-6-methylfenyl]-2, 4-dihydro-5methoxy-2-methyl-3íř-l, 2,4-triazol-3-on;
4-[2-[[[[1-(2-fluoro-5-methylfenyl)ethyliden]amino]oxy]methyl]-6-methylfenyl]-2, 4-dihydro-5-methoxy-2methyl-3íf-l, 2,4-triazol-3-on; a
2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(2thienyloxy)fenyl]-3H-1,2, 4-triazol-3-on.
Vynález se rovněž týká fungicidních kompozic obsahujících fungicidně účinná množství sloučenin podle • ·
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vynálezu a alespoň jedno povrchově aktivní činidlo a pevné nebo kapalné ředidlo. Výhodnými kompozicemi podle vynálezu jsou ty kompozice, které obsahují výše uvedené výhodné sloučeniny.
Vynález se rovněž týká způsobu kontroly rostlinných chorob způsobených fungálními rostlinnými patogeny, přičemž tento způsob je založen na aplikaci fungicidně účinného množství sloučenin podle vynálezu (např. ve formě zde popsané kompozice) na rostlinu, její část, semeno nebo semenáč. Výhodnými způsoby použití jsou ty způsoby, které zahrnují aplikaci výše uvedených výhodných sloučenin.
Vynález se rovněž týká arthropodicidních kompozic obsahujících arthropodicidně účinná množství sloučenin podle vynálezu a alespoň jedno povrchově aktivní činidlo a pevné nebo kapalné ředidlo. Výhodnými kompozicemi podle vynálezu jsou ty kompozice, které obsahují výše uvedené výhodné sloučeniny.
Vynález se rovněž týká způsobu kontroly členovců, přičemž tento způsob je založen na uvedení členovců nebo jejich životního prostředí do styku s arthropodicidně účinným množstvím sloučenin podle vynálezu (např. ve formě zde popsané kompozice). Výhodnými způsoby použití jsou ty způsoby, které zahrnují aplikaci výše uvedených výhodných sloučenin.
Za zmínku stojí sloučeniny, ve kterých T znamená T1, G znamená atom dusíku, A znamená atom dusíku a pohyblivá dvojná vazba je navázána na A; W znamená atom kyslíku; X znamená OCH3; Y znamená -0-, -CH20-, -0CH2-, -CH2O-N=C (R3) nebo přímou vazbu; R8 znamená atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku, halogenoalkylovou skupinu s
01-859-99 Če až 3 atomy uhlíku, alkenylovou skupinu se 2 až 3 atomy uhlíku, alkinylovou skupinu se 2 až 3 atomy uhlíku, cyklopropylovou skupinu nebo kyanoskupinu; Z znamená fenylovou skupinu případně substituovanou R9 a případně substituovanou R10; R9 znamená atom vodíku, atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy se 2 až až 6 až 6 atomy až 6 atomy až 6 atomy atomy uhlíku, atomy uhlíku, atomy uhlíku, atomy uhlíku, uhlíku, uhlíku, uhlíku, uhlíku, halogenoalkoxyskupinu s 1 až alkenylovou skupinu se 2 až 6 halogenoalkenylovou skupinu alkinylovou skupinu se alkylthioskupinu s 1 halogenoalkylthioskupinu s 1 alkylsulfinylovou skupinu s 1 alkylsulfonylovou skupinu s 1 až 6 atomy uhlíku nebo cykloalkylovou skupinu se 3 až 6 atomy uhlíku; a R10 znamená atom vodíku, jeden až dva atomy halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyano s kupinu.
Za zmínku stojí sloučeniny, ve kterých R9 znamená atom vodíku, atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku,
alkylthioskupinu | s 1 až | 6 | atomy | uhlíku, |
halogenoalkylthioskupinu s 1 | až | 6 atomy | uhlíku, | |
alkylsulfinylovou | skupinu s 1 | až | 6 atomy | uhlíku, |
alkylsulfonylovou | skupinu s 1 | až | 6 atomy | uhlíku, |
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cykloalkylovou skupinu se 3 až 6 atomy uhlíku, trimethylsilylovou skupinu, fenylovou skupinu nebo fenoxyskupinu, přičemž každá fenylová skupina nebo fenoxyskupina je případně substituována R12 a případně substituována jedním nebo více R13; za předpokladu, že pokud R9 znamená fenylovou skupinu nebo fenoxyskupinu, které jsou případně substituovány R12 a případně substituovány jedním nebo více R13, potom T neznamená T1.
Za zmínku stojí sloučeniny 1 až 10 a 40, uvedené v indexové tabulce A. Za zmínku stojí rovněž sloučeniny obecného vzorce I, kterými nejsou sloučeniny 1 až 10 a 40 indexové tabulky A (např. sloučeniny 11 až 39 a 41 až 71 indexové tabulky A a sloučenina 72 indexové tabulky B).
Za zmínku stojí rovněž sloučeniny 1 až 19 indexové tabulky A a rovněž sloučeniny 20 až 71 indexové tabulky A a sloučenina 72 indexové tabulky B.
Podrobný popis syntetických postupů
Sloučeniny obecného vzorce I lze připravit jedním nebo několika následujícími postupy a jejich obměnami popsanými v Reakčních schématech 1 až 46. Definice T, A, G, W, X, Y, Z, R1 až R21, m, n, r a s ve sloučeninách obecného vzorce 1 až 62 mají stejný význam jako definice uvedené v podstatě vynálezu. Sloučeniny obecného vzorce Ia až Iy představují různé podskupiny sloučenin obecného vzorce I a všechny substituenty obecných vzorců Ia až Iy jsou definovány stejně jako v případě výše zmíněného obecného vzorce I.
Odborník v daném oboru je informován o tom, že některé sloučeniny obecného vzorce I mohou existovat v jedné nebo
01-859-99 Če několika tautomerních formách. Takže například sloučeniny obecného vzorce I, ve kterých T znamená T1 a R2 znamená atom vodíku mohou existovat ve formě tautomeru Ia nebo Ib, nebo v obou těchto tautomerních formách Ia I Ib. Vynález zahrnuje všechny tautomerní formy sloučenin obecného vzorce I, ve kterých T znamená T1.
Ib
Sloučeniny obecného vzorce I, ve kterém T znamená T1 lze připravit níže popsanými způsoby 1) až 5). Postupy 1) až 4) popisují syntézy zahrnující konstrukci heterocyklu po vytvoření arylového zbytku. Postup 5) popisuje syntézy arylového zbytku s T-zbytkem, který je již na místě.
1) Alkylační postupy
Sloučeniny obecného vzorce Ic, tj. sloučeniny obecného vzorce I, ve kterém T znamená T1, se připraví ošetřením sloučenin obecného vzorce 1 vhodným reakčním činidlem pro příslušný alkylový přesun v inertním rozpouštědle s dalšími nebo bez dalších kyselinových nebo bazických reakčních činidel nebo dalších činidel (Reakční schéma 1) . Vhodná rozpouštědla se zvolí ze skupiny tvořené polárními aprotickými rozpouštědly, jako například acetonitrilem, dimethylformamidem nebo dimethylsulf oxidem; ethery, jako • ·
01-859-99 Če například tetrahydrofuranem, diethyletherem; ketony, jako
2-butanonem; uhlovodíky, jako benzenem; a halogenovanými uhlovodíky, dichloromethanem nebo chloroformem.
dimethoxyethanem nebo například acetonem nebo například toluenem nebo jako například
Reakční schéma 1
X1 = OH nebo SH
X = =0R1 nebo SR1
Metoda 1
U-CH=N2 (U=H nebo (CH3)3Si)
Metoda 2: ll ; Lewisova kyselina
CIjC^OR1
Metoda 3: (R^aO+BFí-
Metoda 4: (R^zSOí; R^SOzQ; nebo Rx-hal; případná fáze (hal=F, Cl, Br nebo I) (Q=Ci-Csalkyl, Ci-C6halogenoalkyl) • · »
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Sloučeniny obecného vzorce Ic, tj. sloučeniny obecného vzorce I, ve kterém T znamená T1, lze například připravit působením diazoalkanových reakčních činidel obecného vzorce 2, například diazomethanu silyldiazomethanu (U=(CH3)3Si) vzorce 1 (metoda 1). Použití trimethylsilyldiazomethanu vyžaduje protické ko-rozpouštědlo, například methanol. Tyto metody lze například nalézt v Chem. Pharm. Bull. (1984), 32, 3759.
(U=H) nebo trimethylna sloučeniny obecného
Jak je naznačeno v metodě 2, sloučeniny obecného vzorce Ic, tj. sloučeniny obecného vzorce I, ve kterém T znamená T1, lze rovněž připravit uvedením karbonylových sloučenin obecného vzorce 1 do styku s alkyltrichloroacetimidáty obecného vzorce 3 a Lewisovou kyselinou jako katalyzátorem. Vhodné Lewisovy kyseliny zahrnují trimethylsilyltrifluormethansulfonát a kyselinu tetrafluoroboritou. Alkyltrichloroacetimidáty lze připravit z vhodného alkoholu a trichloroacetonitrilu způsobem popsaným v literatuře (J. Danklmaier a H. Honig, Synth. Commun., (1990), 20, 203) .
Sloučeniny obecného vzorce Ic, tj. sloučeniny obecného vzorce I, ve kterém T znamená T1, lze rovněž připravit ze sloučenin obecného vzorce 1 ošetřením trialkyloxoniumtetrafluoroborátem (např. Meerweinovou solí) obecného vzorce 4 (metoda 3) . Použití trialkyloxoniových solí jako účinných alkylačních činidel je v daném oboru známo (viz U. Schóllkopf, U.Groth, C.Deng, Angew. Chem., Int .Ed .Engl., (1981) , 20, 798) .
Další alkylační činidla, která mohou převádět sloučeniny obecného vzorce 1 na sloučeniny obecného vzorce • · • · · ·
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Ic, ve kterém T znamená T1, jsou dialkylsulfáty, například dimethylsulfát, halogenoalkylsulfonáty, jako například methyltrifluoromethansulfonát, a alkylhalogenidy, jako například jodomethan a propargylbromid (metoda 4). Tyto alkylace lze provádět s adični bází nebo bez adični báze. Vhodné báze zahrnují alkoxidy alkalických kovů, například terc.-butoxid draselný, anorganické báze, jako například hydrid sodný a uhličitan draselný, pyridin nebo terciální aminy, jako například triethylamin, ' 1,8-diazabicyklo[5.4.0]undek-7-en (DBU) a triethylendiamin. Příklady alkylací, které používají tento typ činidel, lze například nalézt v R. E. Benson, T. L. Cairns, J. Am. Chem. Soc., (1948), 70, 2115.
Sloučeniny obecného vzorce la (sloučeniny obecného vzorce 1, ve kterém G znamená atom uhlíku, W znamená atom kyslíku a X1 znamená hydroxylovou skupinu) lze připravit kondenzací malonátů nebo malonátových derivátů obecného vzorce 5 s ambidentním nukleofilem obecného vzorce 6 (Reakční schéma 2). Nukleofily obecného vzorce 6 jsou Ν'-substituované hydroxylaminy (HO-NHR2) a substituované hydraziny (HN (R5)-NHR2) . Příklady takových nukleofilů jsou N-methylhydroxylamin a methylhydrazin. Malonátestery obecného vzorce 5 (E=0(Ci-C4)alkyl)) lze připravit zde popsanými způsoby. Estery obecného vzorce 5 lze rovněž aktivovat hydrolyzací esteru za vzniku odpovídající karboxyiové kyseliny a následným převedením karboxyiové kyseliny na chlorid kyseliny (E=C1) pomocí thionylchloridu nebo oxalylchloridu, nebo na acylimidazol (E=l-imidazolyl) ošetřením pomocí 1,1'-karbonyldiimidazolu. Sloučeniny obecného vzorce lb lze připravit uvedením nitrilesterů obecného vzorce 7 do reakce s ambidentními nukleofily obecného vzorce 6. Viz M. Scobie a G. Tennant, J. Chem.
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Soc., Chem. Comm., (1994), 2451. Alkylace lb alkylhalogenidy v přítomnosti báze poskytne sloučeniny obecného vzorce lc. Alternativně ošetření lb alkylaminy nebo alkoxyaminy poskytne sloučeniny obecného vzorce lc.
Reakční schéma 2
O (Ci-C4alkyl) , Cl,
1-imidazolyl
nebo
lb
W = NH
H2N (Ci-Cealkyl) nebo
H2NO(Ci-C6alkyl)
W = N(Ci-Csalkyl) nebo NO (Ci-C6alkyl)
·> · * • · ·« | »·*» »· ·· « · · · * * « | |||
01-859-99 Če | 29 | * t « » * » » · · a * « · * | • · * t * * • ♦ » « · » » X * » · * · · · · •« · * * · · | |
Estery obecného | vzorce | 5a | lze | připravit z |
malonátesterů, z reakce | katalyzované | mědil ým | katalyzátorem | |
pomocí substituovaných | jodobenzenů | obecného vzorce 8 |
způsobem získaným přizpůsobením způsobů, které popsal A. Osuka T. Kobayashi a H. Suzuki, Synthesis, (1983), 67. Tento způsob ilustruje Reakční schéma 3.
Reakční schéma 3
5a
R = Ci-C4alkyl
Kromě toho lze malonátestery obecného vzorce 5a připravit ošetřením esterů kyseliny fenyloctové obecného vzorce 9a dialkylkarbonátem nebo alkylchloroformiátem v přítomnosti vhodné báze, jakou je například, ale bez omezení, sodíkový kov a hydrid sodný (Reakční schéma 4). Viz například J. Am. Chem. Soc., (1928), 50, 2758.
Nitrilestery obecného vzorce 7 lze připravit podobným způsobem ze sloučenin obecného vzorce 10.
·· ····
01-859-99 Če t* «·
Reakční schéma 4
báze
R = CiC4-alkyl
Estery obecného vzorce 9, ve kterém vzorce ,1
9a (sloučeniny obecného EA znamená OR) lze připravit z fenylacetonitrilů obecného vzorce 10, získaných kyselinou katalyzovanou alkoholýzou, nebo esterifikaci fenyloctových kyselin obecného vzorce 11, jak ukazuje Reakční schéma 5 (viz Org. Synth., Coli. sv. I, (1941), 270).
• f
01-859-99 Če • ·
Reakční schéma 5
Estery kyseliny fenyloctové obecného vzorce 9b (sloučeniny obecného vzorce 9a, ve kterých Y znamená Y1) lze rovněž připravit měďným katalyzátorem katalyzovanou kondenzací fenylhalogenidů obecného vzorce 12 se sloučeninami obecného vzorce 13, jak popisuje EP-A-307,103 a ilustruje níže uvedené Reakční schéma 6.
OR
9b r = CiC4-alkyl
Y1 = -0-, -OCHz-, -SCHR11• · • · · · • ·
01-859-99 Ce
Sloučeniny obecného vzorce 12 lze rovněž připravit Arndt-Eistertovou syntézou vycházející z benzoových kyselin obecného vzorce 14, kterou ilustruje Reakční schéma 7, (viz F. Arndt, B. Eistert, Ber. 68, 200 (1935); T. Aoyama, T.
Shioiri, Tetrahedron Letters 21, 44 61 (1980)) . Například ošetření kyselin benzoových obecného vzorce 14 halogenačním činidlem, například thionylchloridem, a následná adice alkylačního činidla, například diazomethanu, poskytne meziprodukt, který lze propláchnout R-OH ve vhodném rozpouštědle za vzniku požadovaného esteru obecného vzorce 12.
Reakční schéma 7
1) SOC12, UCHN2 -►
2) ROH, Ag2O
U = H nebo Si(CH3)3
Sloučeniny nitrobenzoových obecného vzorce 14 lze připravit z kyselin obecného vzorce 15 modifikací Sandmayerovy reakce způsobem, který navrhli S. Kanoh, H. Muramoto, N. Kobayashi, M. Motoi a H. Suda, Bull. Chem. Soc. Jpn. 60, 3659 (1987) a Μ. P. Doyle, J. Org. Chem. 42, 2426 (1977) (Reakční schéma 8). Nitrobenzoové kyseliny
15, ve kterých R3 znamená methylovou znamená atom vodíku nebo R3 znamená atom vodíku a R4 znamená methylovou skupinu, jsou komerčně dostupné ve formě odpovídajících anthranilových kyselin (ve obecného skupinu a vzorce
R4 ,4 ·· ···· ·· ·· »··» ·· · · · · ·
01-859-99 Če kterých se nitroskupina nahradí aminoskupinou). Sloučeninu, ve které R3 = R4 = CH3/ lze připravit nitrací a redukcí komerčně dostupné kyseliny 2,5-dimethylbenzoové způsobem, který navrhli A. N. Fugiwara a E. M. Acton, Can. J. Chem. 48, 1346 (1970).
Reakční schéma 8
1) redukce
2) NaN02/H+
-►
3) M+(C1, Br , 1)”
M+ = K, Na
ČO2H
Některé estery obecného vzorce 9c lze rovněž připravit vytvořením Y2 můstku pomocí konvenční nukleofilní substituční chemie (Reakční schéma 9). Nahrazení příslušné odstupující skupiny (Lg) v elekrofilech obecného vzorce 17 nebo 18 nukleofilním esterem obecného vzorce 16 poskytne sloučeniny obecného vzorce 9c. Báze, například hydrid sodný, se použije k vytvoření odpovídajícího alkoxidu nebo thioalkoxidu sloučeniny obecného vzorce 16.
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Reakční schéma 9
Lg-Z nebo
-►
Lg-CHR^-Z báze
R = Ci-C4alkyl
R14 = OH, SH, CH2OH, CH2SH
Y2 = -0-, -OCH2-, -SCHR11-, -CH2O-, -CH2S(0)nLg = Br, Cl, I, OSO2CH3, OSO2 (4-Me-Ph)
Sloučeniny obecného vzorce 16 lze připravit ze sloučenin obecného vzorce 12 způsobem popsaným v Chem. Pharm. Bull. 33 (12), 5184 (1985) nebo J. Org. Chem. 53 (2) 439, (1988). Například ošetření sloučenin obecného vzorce 12 hydroxidem kovu, jakým je například hydroxid sodný, v polárním protickém rozpouštědle v přítomnosti kovových druhů, například mědi, se získá sloučenina obecného vzorce 16a (sloučeniny obecného vzorce 16, ve kterých R14 znamená hydroxylovou skupinu). Sloučeniny obecného vzorce 16b (sloučeniny obecného vzorce 16, ve kterých R14 znamená CH2OH nebo CH2SH) lze připravit výměnou kov-halogen ve sloučeninách obecného vzorce 12 a následným propláchnutím vhodným elektrofilem. Například ošetření sloučenin obecného vzorce 12 vhodným alkyllithiem, například n-butyllithiem v inertním rozpouštědle, jakým je například ether nebo tetrahydrofuran (THF), a následné
01-859-99 Če • ·
Academie Press: propláchnutí propláchnutí elektrofilem, například paraformaldehydem, by poskytlo sloučeninu obecného vzorce 16b (ve které R14 znamená CH2OH) , viz B. J. Wakefield Organolithium Methods;
New York, (1988)). Alternativně poskytne metalovaných druhů formaldehydovým ekvivalentem D-CHO (ve kterém D znamená (CH3)2N nebo OMe) a následná redukce aldehydu vhodným redukčním činidlem sloučeniny obecného vzorce 16b. Příklady takových redukčních činidel jsou borohydrid sodný (NaBH4), kyanoborohydrid sodný (NaCNBHJ a diisobutylaluminiumhydrid (DIBAL-H) (Reakční schéma 10) . Vhodnými inertními rozpouštědly jsou methanol, ethanol, methylenchlorid a THF (viz M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons: New York, (1986)).
Reakční schéma 10
D
Některé estery obecného vzorce 9d lze rovněž připravit vytvořením Y3 můstku z vhodných hydroxylaminů obecného vzorce 16d a karbonylových sloučenin obecného vzorce 19. Hydroxylaminy obecného vzorce 16d se zase připraví z esterů obecného vzorce 16c. Sloučeniny obecného vzorce 16c, ve
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kterých Lg znamená atom bromu, chloru nebo jodu, 0S02CH3 nebo OSO2 (4-Me-Ph), lze připravit ze sloučenin obecného vzorce 16d (viz March J., Advanced Organic Chemistry; 3. vyd., John Wiley: New York, (1985). Tato metoda byla popsána v EP-A-600,835 a ilustruje ji Reakční schéma 11. Estery obecného vzorce 9d lze použít pro přípravu sloučenin obecného vzorce Id, ve kterých T znamená T2 nebo T3 * * * *, způsoby popsanými v EP-A-600,835.
Reakční schéma 11
16c B = CHR^Lg 16d B = CHR^ONHz . HCI
R = C1-C4alkyl Y3 = -CHR1:lON=C (R8)
T = T2 nebo T3
2) Vytěsňovací a konjugační adičně/eliminační postupy
Sloučeniny obecného vzorce Ic, tj. sloučeniny obecného vzorce I, ve kterých T znamená T1, lze rovněž připravit uvedením sloučenin obecného vzorce 20 do reakce s alkoxidy alkalických kovů (R1OM+) nebo thioalkoxidy alkalických kovů (R1SM+) ve vhodném rozpouštědle (Reakční schéma 12).
Odstupující skupinou Lg1 v amidech obecného vzorce 20 je libovolná v daném oboru známá skupina, která podléhá vytěsňovací reakci tohoto typu. Příklady vhodných odštěpujících se skupin zahrnují atom chloru, atom bromu a
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sulfonylovou a sulfonátovou skupinu. Příklady vhodných inertních rozpouštědel jsou dimethylformamid nebo dimethylsulfoxid.
Reakční schéma 12
Ic
Lg1 = Cl, Br, -S02Q nebo -OSO2Q Q = Ci-C6alkyl nebo Ci-Cs halogenoalkyl Μ = K nebo Na
Sloučeniny obecného vzorce 20a lze připravit ze sloučenin obecného vzorce ld (sloučeniny obecného vzorce 1, ve kterých X1 znamená hydroxylovou skupinu) reakcí s halogenačními činidly, jako například s thionylchloridem nebo oxybromidem fosforečným za vzniku odpovídajících βhalogenem substituovaných derivátů (Reakční schéma 13) . Alternativně lze sloučeniny obecného vzorce ld ošetřit alkylsulfonylhalogenidem nebo anhydridem halogenoalkylsulfonylu, jako například methansulfonylchloridem, p-toluensulfonylchloridem a anhydridem trifluoromethansulfonylu, za vzniku odpovídajícího β-alkylsulfonátu obecného vzorce 20b. Reakci se sulfonylhalogenidy lze provádět v přítomnosti vhodné báze (např. triethylaminu).
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Reakční schéma 13
V2 ld
Halogenační činidlo
-► nebo QSO2-hal nebo QSO2- 0—O2SQ
20a Lg1 = Cl nebo Br 20b Lg1 = -0S02Q
Q = Ci-C6alkyl nebo Ci-C6halogenoalkyl hal = Br, Cl nebo F
Jak ukazuje Reakční schéma 14, sulfonylové sloučeniny obecného vzorce 20c (sloučeniny obecného vzorce 20, ve kterých Lg1 znamená QSO2-) lze připravit oxidací odpovídající thiosloučeniny obecného vzorce 21 za použití dobře známých metod oxidace síry (viz Schrenk K. v The Chemistry of Sulphones and Sulphoxides; Patai S. a kol., vyd.; Wiley: New York, (1988)). Vhodná oxidační reakční činidla zahrnují kyselinu meta-chloroperoxybenzoovou, peroxid vodíku a Oxone (KHSO5) .
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Reakční schéma 14
Q = Ci-C6alkyl nebo Ci-C6halogenoalkyl
Alternativně lze halogenosloučeniny obecného vzorce 20d (sloučeniny obecného vzorce 20, ve kterých A znamená atom dusíku, G znamená atom dusíku a W znamená atom kyslíku) připravit z hydrazidů obecného vzorce 22, jak ukazuje Reakční schéma 15. Pokud R15 znamená C(=S)S(CiC4alkyl), potom se sloučenina obecného vzorce 22 ošetří přebytkem thionylhalogenidu, jakým je například thionylchlorid. Vzniklým produktem je nejprve sloučenina mající uzavřený kruh obecného vzorce 23, kterou lze izolovat nebo převést in sítu na sloučeniny obecného vzorce 20d; viz P. Molina, A. Tárraga, A. Espinosa, Synthesis, (1989), 923, kde lze nalézt popis tohoto postupu.
Alternativně, pokud R15 znamená R2, který byl definován výše, potom se hydrid obecného vzorce 22 cyklizuje s fosgenem za vzniku cyklické močoviny obecného vzorce 20d, ve kterém hal znamená chlor. Tento postup je podrobně popsán v J. Org. Chem., (1989), 54, 1048.
• · · «
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Reakční schéma 15
hal = Cl, Br, 1
Hydrazidy obecného vzorce 22 lze připravit způsobem, který ilustruje Reakční schéma 16. Kondenzace isokyanátu obecného vzorce 24 s hydrazinem obecného vzorce H2NNR2R15 v inertním rozpouštědle, jakým je například tetrahydrofuran poskytne požadovaný hydrazid.
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R15 = C (S) S (Ci-C4alkyl) nebo R2
3) Konjugační adičně/cyklizační postupy
Kromě pomocí výše popsaných postupů lze sloučeniny obecného vzorce I, ve kterém T znamená Τ1, X znamená SR1 a G znamená C (obecný vzorec le), připravit ošetřením ketendithioacetálu obecného vzorce 25 ambidentním nukleofilem obecného vzorce 6 (Reakční schéma 17). Nukleofily obecného vzorce 6 jsou popsány výše.
Reakční schéma 17
C(=W)O(Ci-C4alkyl)
01-859-99 Ce • · · a • » a • · « · · a • 4 • · · ·
Ketendithioacetály obecného vzorce 25a (sloučeniny obecného vzorce 25, ve kterém R1S znamená CO2 (Ci~C4alkyl)) nebo 25b (sloučeniny obecného vzorce 25, ve kterém R16 znamená C(=O)NHQ4) lze připravit kondenzací esterů kyseliny fenyloctové obecného vzorce 9a resp. amidů obecného vzorce 9e (sloučeniny obecného vzorce 9, ve kterém E1 znamená NHQ4) se sirouhlíkem v přítomnosti vhodné báze a následnou reakcí se dvěma ekvivalenty R1-halogenidu, například jodomethanu nebo propargylbromidu (Reakční schéma 18). Konverzi 25b na '25c (sloučeniny obecného vzorce 25, ve kterém R1S znamená C(=NQ4)OR) lze provést reakcí s trialkyltetrafluoroboráty.
OR
1) CS2, báze
R = Ci-C4alkyl
1) CS2, báze
2) 2 ekviv. ^-(Cl, Br,
Reakční schéma 18
Q4 = H, Ci-Cealkyl, Cá-Csalkoxy
R3O+BF4~
25c • · ·
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Sloučeniny obecného vzorce le (sloučeniny obecného vzorce 1, ve kterém A znamená atom dusíku a G znamená atom dusíku) lze připravit kondenzací N-aminomočovin obecného vzorce 2 6 s karbonylačním činidlem (Reakční schéma 19) . Karbonylačními činidly jsou reakční činidla přesunující karbonylovou nebo thiokarbonylovou skupinu, jako například fosgen, thiofosgen, difosgen (C1C(=0)OCC13), trifosgen (C13COC (=0) OCCI3) , Ν,Ν'-karbonyldiimidazol, Ν,Ν'-thiokarbonyldiimidazol a 1,1'-karbonyldi(1,2,4-triazol). Alternativně mohou být karbonylačními činidly alkylchloroformiáty nebo dialkylkarbonáty. Některé z těchto karbonylačních reakcí mohou vyžadovat přidání báze. λ/hodnými bázemi jsou v tomto případě například alkoxidy alkalických kovů, anorganické báze, draselný, pyridin zejména terč.-butoxid draselný, například hydrid sodný a uhličitan nebo terciální aminy, například triethylamin, 1,8-diazabicyklo[5.4.0]undek-7-en (DBU) nebo triethylendiamin. λ/hodná rozpouštědla zahrnují polární aprotická rozpouštědla, například acetonitril, dimethylformamid nebo dimethylsulfoxid; ethery, například tetrahydrofuran, dimethoxyethan nebo diethylether; ketony, například aceton nebo 2-butanon; uhlovodíky, například toluen nebo benzen; nebo halogenované uhlovodíky, například dichloromethan nebo chloroform. Reakční teplota se může pohybovat v rozmezí od 0°C do 150°C a reakční doba od 1 do 72 hodin, v závislosti na volbě konkrétní báze, rozpouštědla, teploty a substrátů.
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Reakční schéma 19
H->N—N
X2
případná báze
\2 lé
Q1 a Q2 znamenají nezávisle Cl, OCC13, O(Ci~C4alkyl), 1-imidazolyl, 1,2,4-triazolyl
X1 = OH nebo SH
X2 = O nebo S
N-aminomočoviny obecného vzorce 26 lze připravit způsobem, který ilustruje Reakční schéma 20. Ošetření anilinu obecného vzorce 27 fosgenem, thiofosgenem, Ν,Ν'-karbonyidiimidazolem nebo Ν,Ν'-thiokarbonyldiimidazolem poskytuje isokyanát nebo thioisokyanát obecného vzorce 28. Do reakční směsi lze při reakci s fosgenem nebo thiofosgenem přidat bázi. Následné ošetření iso(thio)kyanátu R2-substituovaným hydrazinem poskytne N-aminomočovinu obecného vzorce 26.
Reakční schéma 20
případná báze
CWC12 nebo
W
N^N-^N^N
V=/ U/ ->.
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R2- NH-NH2 w=o,s
(sloučeniny
Y4) lze připravit z redukčními metodami, obecného
Aniliny obecného vzorce 27a vzorce 27, ve kterých Y znamená nitrosloučenin obecného vzorce 29 které jsou v daném oboru známy a které ilustruje Reakční schéma 21 (viz M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons str. 69 až 76 (1986)).
Reakční schéma 21
Y4 = -CH2O-, -CHRl Io-N= C(R8)-, -CH2S(O)nSloučeniny obecného vzorce 29 lze připravit uvedením benzylhalogenidů, mesylátů nebo tosylátů obecného vzorce 30 do styku s různými nukleofily (Reakční schéma 22). Příslušný alkohol nebo thiol se ošetří bází, například hydridem sodným, za vzniku odpovídajícího alkoxidu nebo thioalkoxidu, který působí jako nukleofil.
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Reakční schéma 22
HOZ
-►
HON = C(R8)Z nebo HS-Z: báze
Lg = Br, Cl, I, OSO2CH3, 0S02 (4-Me-Rh)
Sloučeniny obecného vzorce 30 lze připravit z odpovídajících nitrobenzylakoholů obecného vzorce 30a (sloučeniny obecného vzorce 30, ve kterém Lg skupina byla nahrazena hydroxylovou skupinou) reakcí s halogenačními činidly, například s thionylchloridem nebo oxybromidem fosforečným za vzniku odpovídajících β-halogenem substituovaných derivátů (Reakční schéma 23) . Sloučeniny obecného vzorce 30a lze rovněž ošetřit alkylsulfonylhalogenidem nebo anhydridem halogenoalkylsulfonylu, například methansulfonylchloridem, p-toluensulfonylchloridem a anhydridem trifluoromethansulfonylu, za vzniku odpovídajícího β-alkylsulfonátu obecného vzorce 30. Reakci se sulfonylhalogenidy lze provádět v přítomnosti vhodné báze (např. triethylaminu).
báze
30a • · · • ·
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Sloučeniny obecného vzorce 30a lze připravit redukcí nitrobenzoových kyselin obecného vzorce 31 vhodným redukčním činidlem, například boranem v tetrahydrofuranu nebo dimethylsulfidu jak uvádí M. Pavia, W. H. Moos a F. M. Hershenson, J. Org. Chem. 55, 560, (1990) nebo C. F. Lané, H. L. Myatt, J. Daniels a Η . B. Hopps, J. Org. Chem. 39, 3052, (1974) (Reakční schéma 24).
31 BH3 · DMS
2-halogenokarboxylové, karboxylové nebo
Sloučeniny obecného vzorce lf (sloučeniny obecného vzorce 1, ve kterém A znamená CR5, G znamená atom dusíku a X znamená atom kyslíku) lze připravit způsoby, které ilustruje Reakční schéma 25. Močoviny obecného vzorce 32 se uvedou do reakce s aktivovanými deriváty kyseliny
2-halogenokarboxylové, například s chloridy kyseliny estery kyseliny 2-halogeno2-halogenoacylimidazoly obecného vzorce 33. Po acylací na anilinovém dusíku následuje intramolekulární vytěsnění 2-halogenoskupiny a dojde k cyklizaci. Urychlení acylace a/nebo následné cyklizace lze dosáhnout přidáním báze. Vhodné báze zahrnují triethylamin a hydrid sodný. Alternativně lze sloučeniny obecného vzorce lf připravit uvedením iso(thio)kyanátů obecného vzorce 28 nebo karbodiimidů obecného vzorce 28a do reakce s estery obecného vzorce 35. Jak je popsáno výše, pro urychlení reakce a následné cyklizace na sloučeniny • ·
J · < « • 4
01-859-99 Če obecného vzorce lf lze do reakční směsi přidat bázi. Karbodiimidy obecného vzorce 28a lze připravit způsobem, který ukazuje Reakční schéma 25 a který jako výchozí surovinu používá sloučeniny obecného vzorce 28. V tomto případě se vznikající sloučeniny obecného vzorce 34 dehydratují a poskytnou sloučeniny obecného vzorce 28a.
Reakční schéma 25
případná báze
O3 CHR5-ha!
Q3 = C1,O(C1-C4 alkyl), nebo 1-imidazolvl
případná báze q5nh?
hal = Cl, Br nebo I
R2NHCHR5C(O)OR 35 lf
W = O, S, NQ5
.Z dehydratace
případná báze ,/Z R = Cj-C4 alkyl
W = O, S
W = NQ5
Q5 = Cj-Cg alkyl, Cj-Cg alkoxy • F t · · ·
01-859-99 Če « · ·» » * » · (Thio)močoviny nebo amidiny obecného vzorce 32 lze připravit některým ze způsobů, které ilustruje Reakční schéma 26. Aniliny obecného vzorce 27 lze uvést do styku s isokyanátem nebo isothiokyanátem obecného vzorce RZN=C=W výše popsaným způsobem. Alternativně lze iso(thio)kyanát obecného vzorce 28 nebo karbodiimid obecného vzorce 28a kondenzovat s aminem obecného vzorce R2-NH2 za vzniku močoviny nebo amidinu. Aniliny a iso(thio)kyanáty obecného vzorce 27 resp. 28 jsou komerčně dostupné nebo se připraví známými postupy. Isothiokyanáty lze například připravit způsoby popsanými v J. Heterocycl. Chem., (1990), 27, 407. Isokyanáty lze zase připravit způsobem popsaným Marchem v J. Advanced Organic Chemistry; 3. vyd., John Wiley: New York, (1985), str. 944, 1166.
Reakční schéma 26
R2— NH2
W=OneboS 28a W = NQ5 ·· ·· ·»·· *· ··
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4) Thionační postupy
Sloučeniny obecného vzorce If (sloučeniny obecného vzorce Ic, ve kterém W znamená atom síry) lze připravit ošetřením sloučenin obecného vzorce Ig (sloučenin obecného vzorce Ic, ve kterém W znamená atom kyslíku) thionačními reakčními činidly, například P2S5 nebo Lawessonovým reakčním činidlem [2,4-bis(4-methoxyfenyl)-1,3-dithia-2,4difosfetan-2,4-disulfidem] způsobem, který ukazuje Reakční schéma 27 (viz Bull. Soc. Chim. Belg., (1978), 87, 229; a Tetrahedron Lett., (1983), 24, 3815).
Reakční schéma 27
P2S5 nebo
Lawessonovo činidlo
X = OR1 nebo SR1
Reakce sloučenin obecného vzorce Ih s alkylhalogenidem v přítomnosti báze poskytuje sloučeniny obecného vzorce li, které lze uvést do reakce se sloučeninami obecného vzorce Q5NH2 a následně alkylovat R2-(C1, Br nebo I) za vzniku sloučenin obecného vzorce Ij.
• · · · • · • ·
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• · · ·
Reakční schéma 28
5) Postupy založené na syntéze arylového zbytku
Sloučeniny obecného vzorce Ik (sloučeniny obecného vzorce I, ve kterém Y znamená -CH20-, CH2S(O)n-, -CHR11O-N=C (R8) - lze připravit vytěsněním příslušné odštěpující se skupiny (Lg) v elektrofilech obecného vzorce 3 6 různými nukleofily (Reakční schéma 29) .
Reakční schéma 29
Y4 = -CH20-, -CH110-N=C(R8)-, -CH2S(O)n• · · ·· · · · · ·· ···· ·· · ···· ·· · ·· · ···· • · · ·· ·· · ······ • · · ··· · · • · · · · « · · ·· · ·
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Příslušný alkohol nebo thiol se ošetří bází, například hydridem sodným, za vzniku odpovídajícího alkoxidu nebo thioalkoxidu, který působí jako nukleofil. Sloučeniny obecného vzorce Ik (sloučeniny obecného vzorce I, ve kterém T znamená T2 a Y znamená Y4, které je definováno v Reakčním schématu 29) lze připravit způsoby popsanými v následujících dokumentech: postup pro Y4 znamená -CH20- lze nalézt v EP-A-278,595 a EP-A-472,224; postup pro Y4 znamená -CH2S(0)n _ lze nalézt v EP-A-379, 098; a pro Y4 znamená -CHR11O-N=C (R8) - v EP-A-370, 629 a WO 94/05620. Sloučeniny obecného vzorce Ik (sloučeniny obecného vzorce I, ve kterém T znamená T3 a Y znamená Y4, které je definováno v Reakčním schématu 29) lze připravit pomocí postupů popsaných v následujících dokumentech: postup pro Y4 znamená -CH2O- lze nalézt v EP-A-253,213, EP-A-498,188 a EP-A-554,767; postup pro Y4 znamená -CH2S(O)n- lze nalézt v EP-A-374,811; a pro Y4 znamená -CHR11O-N=C (R8) - v EP-A-414,153, EP-A-472,300, EP-A-515,901 a WO 92/18494.
Sloučeniny obecného vzorce Im (sloučeniny obecného vzorce I, ve kterém T znamená T1, X znamená OR1, R1 znamená methylovou skupinu, R2 znamená methylovou skupinu, znamená atom kyslíku, A znamená atom dusíku, G znamená atom dusíku, Y5 znamená -0-, -OCH2- nebo -SCHR11-) lze připravit vytvořením Y5 můstku pomocí konvenční nukleofilní substituční chemie (Reakční schéma 30). Vytěsnění příslušné odštěpující se skupiny (Lg) v elektrofilech obecného vzorce 17 nebo 18 nukleofilními sloučeninami obecného vzorce 36 poskytne sloučeniny obecného vzorce Im. Pro přípravu odpovídajícího alkoxidu nebo thioalkoxidu sloučenin obecného vzorce 37 se použije báze, například hydrid sodný. V některých případech může být výhodný další
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substituent na Z, který aktivuje odštěpující se skupinu (Lg) (např. pokud Lg-Z znamená 2-chloro-3-nitrothiofen, potom lze aktivační nitroskupinu odstranit až po ukončení redukce a následné diazotace a redukce získaného aminu, které vedou ke vzniku sloučenin obecného vzorce Im).
Reakční schéma 30
R17 = OH nebo SH
Lg-Z nebo
-►
Lg-CHRX1-Z báze
Y5 =
-o-, -och2-, -schr11Benzylhalogenidy obecného vzorce 38 lze připravit radikálovou halogenací odpovídající alkylové sloučeniny obecného vzorce 39a, viz WO 96/38425. Benzylhalogenidy lze rovněž připravit kyselinovým štěpením odpovídajícího methyletheru obecného vzorce 39b za podmínek, které poskytují halogenid, viz Reakční schéma 31. Způsoby přípravy odpovídajících sloučenin obecného vzorce 38, ve kterých T1 skupina byla nahrazena T2 jsou popsány ve WO 94/05620. Způsoby přípravy odpovídajících sloučenin obecného vzorce 38, ve kterých T1 skupina byla nahrazena T3, jsou popsány v EP-A-254,426, EP-A-299,694 a
AU-A-55899/90.
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Reakční schéma 31
39a R18 = H 39b R18 = OCH3
1) NBS, CCl4, hv R18 = H
-► nebo
2) morfolin konc. HCI, H2O R18 = OCH3
Alternativně lze sloučeniny obecného vzorce 38 připravit z odpovídajícího alkoholu obecného vzorce 40 reakcí s halogenačními činidly, jakými jsou například thionylchlorid nebo oxybromid fosforečný, která poskytne odpovídající β-halogenem substituované deriváty. Alternativně lze sloučeniny obecného vzorce 40 ošetřit alkylsulfonylhalogenidem nebo anhydridem halogensulfonylu, například methansulfonylchloridem, p-toluensulfonylchloridem a anhydridem trifluoromethansulfonylu, za vzniku odpovídajícího β-alkylsulfonátu obecného vzorce 41. Reakce se sulfonylhalogenidy se může provádět v přítomnosti vhodné báze (např. triethylaminu), viz Reakční schéma 32.
• v « · · · · · ·· • ·
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Reakční schéma 32
Lg2 = Cl, Br
Lg2 = OSQz nebo OSO2(4-Me-Ph)
Sloučeniny obecného vzorce 42a, ve kterém T znamená T3, lze použít pro přípravu sloučenin obecného vzorce Io, ve kterém T znamená T4 a Y3 znamená -CHR110-N=C (R8) -, při použití způsobů popsaných v EP-A-585,751 a ilustrovaných Reakčním schématem 33. Sloučeniny obecného vzorce 42a se ošetří N-hydroxyftalimidem. Ošetření tohoto meziproduktu HNRSR5 poskytne sloučeniny obecného vzorce 42b, ve kterém T3 je převedeno na T4 a B znamená CHR11ONH2. Ošetření sloučenin obecného vzorce 42b sloučeninami obecného vzorce 19 poskytne sloučeniny obecného vzorce Io.
Reakční chéma 33
2) aq. HNR6r5
Io Y3 = -CHRHoN=C(R8)= T3 =-C(=NORl)-COOR5 [2, T = t4 = -C(=NOR1)-CONr6r5
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Sloučeniny obecného vzorce 40 lze připravit redukcí esterů obecného vzorce 44 nebo aldehydů obecného vzorce 43 vhodným redukčním činidlem (M. Hudlicky, Reductions in Organic Chemistry; John Wiley & Sons str. 147 až 160, (1986)). Například diisobutylaluminiumhydrid (DIBAL-H) lze použít pro redukci sloučeniny obecného vzorce 44 v inertním rozpouštědle, jakým je například methylenchlorid, diethylether nebo tetrahydrofuran. Sloučeniny obecného vzorce 43 lze redukovat borohydridem sodným v protickém rozpouštědle, jakým je například methanol nebo ethanol, Reakční schéma 34.
Reakční schéma 34
Estery obecného vzorce 44 lze připravit z esterů kyseliny anthranilové obecného vzorce 45 postupy, které ilustruje Reakční schéma 35. Estery obecného vzorce 45 lze připravit esterifikačními technikami známými v daném oboru ze snadno dostupných kyselin anthranilových.
·· f ·· ···· · · »··* · · · ···
01-859-99 Če • · * ·· · · · · · · • · · « . · « 4 ·· «·· · · · · ·
Reakční schéma 35
1) Fosgen
2) H2NN(CH3)2 -►
3) Fosgen
4) MeOH/NaOMe
CH3
Sloučeniny obecného vzorce 43 lze připravit buď výměnou kov-halogen ve sloučeninách obecného vzorce 46a (ve kterých R19 znamená chlor, brom, jod) nebo metalací sloučenin obecného vzorce 46b (ve kterých R19 znamená atom vodíku) alkyllithnými reakčními činidly v inertním rozpouštědle. Propláchnutí metalovaných druhů formaldehydovým ekvivalentem (tj . dimethylformamidem nebo methylchloroformiátem) poskytne sloučeninu obecného vzorce 43 (viz Reakční schéma 36).
Reakční schéma 36
1) Alkyllithium
2) D-CHO
-► h3o+
D = (Me)2N, OCH3
Ν—N xch3
Ν— xch3
46a R19 = Cl, Br nebo I 46b R19 = H
Sloučeniny obecného vzorce 46 se připraví z komerčně dostupných anilinů obecného vzorce 47 postupy, které jsou
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popsány pro syntézu sloučeniny obecného vzorce 44 a které naznačuje Reakční schéma 37.
Reakční schéma 37
1) Fosgen
2) H2NN(CH3)2 ->
3) Fosgen
4) CH3OH/NaOMe
Sloučeniny obecného vzorce 37a (sloučeniny obecného vzorce 37, ve kterých R17 znamená hydroxylovou skupinu) lze připravit oxidačním zpracováním meziproduktových kyselin borových obecného vzorce 48. Sloučeniny obecného vzorce 48 se zase mohou připravit ze sloučenin obecného vzorce 46 metalací pomocí alkyllithia a následným propláchnutím trialkoxyboranem (Reakční schéma 38), viz Organic Synthesis via Boranes; Wiley: New York, (1975).
CH3
37a
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Alternativně lze sloučeniny obecného vzorce 37b (sloučeniny obecného vzorce 37, ve kterém R3 znamená methylovou skupinu, R4 znamená atom vodíku a R17 znamená hydroxylovou skupinu) připravit cestou, kterou naznačuje Reakční schéma 39. Komerčně dostupné aniliny obecného vzorce 49a (ve kterých R3 znamená methylovou skupinu a P znamená ochrannou skupinu) se výše popsanými postupy převedou na triazol obecného vzorce 50. Odstranění ochranné skupiny z kyslíku a následná alkoholýza poskytnou sloučeniny obecného vzorce 37b. Alternativně lze sloučeniny obecného vzorce 49b (ve kterých R3 znamená atom vodíku a P znamená ochrannou skupinu), jak již bylo uvedeno, převést na triazol obecného vzorce 51. Metalace v ortho-poloze a následné propláchnutí elektrofilem, jakým je například Mel, poskytnou sloučeninu obecného vzorce 52, která po odstranění ochranné skupiny poskytne sloučeninu obecného vzorce 37b, viz Reakční schéma 39.
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Reakční schéma 39
49a R3 = CH3
1) Fosgen
2) H2NN(CH3)2
3) Fosgen
CH3
1) „odstranění ochranné skupiny“
2) CH3OH/NaOMe
Y
37b
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Sloučeniny obecného vzorce 37c (sloučeniny obecného vzorce 37, ve kterém je R3 shodné s R4 a znamená methylovou skupinu a R17 znamená hydroxylovou skupinu) lze připravit ze sloučenin obecného vzorce 54 již popsaným postupem. Sloučeniny obecného vzorce 54 se připraví nitrací komerčně dostupného 2,5-dimethylfenolu obecného vzorce 53 způsobem, který popsal M. Quertani, P. Girard a Η. B. Kagan, Tetrahedron Letters, 23, 4315 (1982), Reakční schéma 40.
Reakční schéma 40 /\Ζ^'
1) HNO2
2) „zavedení ochranné skupiny“
->3) redukce nh2
CH3
37c ch3
Sloučeniny obecného vzorce I, ve kterém Y znamená -CR11=CR11- lze připravit způsobem, který ilustruje Reakční schéma 41. Ošetření sloučenin obecného vzorce 36a (sloučenin obecného vzorce 36, ve kterém Lg znamená chlor, brom nebo jod) trifenylfosfinovým nebo trialkylfosfitovým postupem poskytne odpovídající fosfoniovou sůl (obecného vzorce 55a) resp. fosfonát (obecného vzorce 55b). Kondenzace fosforové sloučeniny s bází a karbonylovou sloučeninou obecného vzorce Z(R1:L)C=O poskytne olefin obecného vzorce Ip. Sloučeniny obecného vzorce Ip, ve kterých T znamená T2, lze připravit způsoby popsanými v EP-A-203, 606, EP-A-474,042, EP-A-528,245 a FR 2,670,781. Sloučeniny obecného vzorce Ip, ve kterých T znamená T3, lze připravit způsoby popsanými v EP-A-253,213 a EP-A-254,426.
01-859-99 Če
Reakční schéma 41
55a R20 = P(C6H5)3+ (Cl, Br nebo I)
O'.
55b R20 = P(O(Ci-C4alkyD)2
O=C(Rll)Z báze
[P katalyzátor
Ho
iq
Olefin obecného vzorce Ip lze rovněž připravit reverzí reaktivity reakčních látek při Wittigově nebo HornerEmmonsově kondenzaci. Například 2-alkylfenylové deriváty obecného vzorce 56 lze převést na odpovídající dibromosloučeniny obecného vzorce 57a, jak ukazuje Reakční schéma 42 (viz Synthesis, (1988), 330). Dibromosloučeniny lze hydrolyzovat na odpovídající karbonylové sloučeniny obecného vzorce 57b, které lze zase kondenzovat s nukleofilem obsahujícím fosfor obecného vzorce 58 nebo 59 a získat tak olefiny obecného vzorce Ip.
01-859-99 Če
Reakční schéma 42
.R4 | 1) Br2 nebo NBS | /R4 | |||
R3/Z | T | ^CH2RH | 2 ekviv., CCL) světlo | kR21 | |
T 56 | 2) morfolin konc.HCl,H2O | T 57 |
NBS = jV-bromosukcinimid
57a R21 = CÍBr^R11 57b r21=C(=O)RH (C6H5)3P=C(RlI)Z
5S
O
II nebo
M+ [ ((C1-C4 alkyI)0)2PC(R> >)Z ] 59
ip
Oximy obecného vzorce Ir (obecný vzorec I, ve kterém Y znamená -C (R8) =N-O-CHRX1) lze připravit z karbonylových sloučenin obecného vzorce 60 kondenzací s hydroxylaminem a elektrofily obecného vzorce (Reakční schéma 43) . Alternativně hydroxylaminy kondenzovat s karbonylovou sloučeninou obecného vzorce 60 za vzniku oximů obecného vzorce Ir přímo. Sloučeniny obecného vzorce Ir, ve kterém T znamená T2, T3 nebo T4, lze připravit způsoby popsanými v EP-A-499,823 a EP-A-596,254.
následnou O-alkylací ZCHR^-ÍCl, Br nebo I) lze O-substituované
Reakční schéma 43
nebo h2n-ochrHz
1) H2N-OH r.
2) ZCHRH-(CtBmeboI)
C(R8)=N-OCHRnz
01-859-99 Če • · · ·<·* · · ·
Karbamáty obecného vzorce lu lze připravit uvedením benzylalkoholů obecného vzorce 61 do reakce s iso(thio)kyanáty obecného vzorce 62 (Reakční schéma 44). Jako katalyzátor lze do této reakce přidat bázi, jakou je například triethylamin. Sloučeniny obecného vzorce lu, ve kterém T znamená Τ2, T3 nebo T4, lze připravit způsoby popsanými ve WO 93/07116.
Reakční schéma 44
CHRllOH
ZNCS
lu
Sloučeniny obecného vzorce Iw lze připravit způsoby popsanými v EP-A-178,826, EP-A-341,845 a EP-A-464,381.
Sloučeniny obecného vzorce Ix, které jsou definovány v Reakčním schématu 45, lze připravit způsoby popsanými v EP-A-398, 692.
Reakční schéma 45
O-Z
Y6 = -O-. -CH2CH2-, -CR11=crJL -CH2O-, -OCH2-. -CH2S(O)nnebo-S(O)nCHRU-
01-859-99 Če • · · · » * · «
I · · · * · · · · « • · • a · ·
Sloučeniny obecného vzorce Iy (sloučeniny obecného vzorce I, ve kterém Y7 znamená -O-) lze připravit ošetřením sloučenin obecného vzorce 62 triarylbismutovou sloučeninou nebo substituovanou kyselinou fenylborovou v přítomnosti octanu měďnatého a terciálního aminu, například pyridinu nebo triethylaminu, jak ilustruje Reakční schéma 46. Použití organobismutových reakčních činidel při přípravě diaryletherů je v daném oboru známé (viz například Tetrahedron Lett. (1986), 27, 3619 a Tetrahedron Lett., (1987), 28, 887).- Kyseliny borové jsou známy z literatury (viz například Acta Chem. Scand. 1993, 47, 221 a odkazy v nich uvedené).
Reakční schéma 46
BiZ3
--3 nebo (HO)2BZ
Eí3N, Cu(OAc)2
Je třeba vzít v úvahu, že některá výše popsaná reakční činidla a reakční podmínky popsané v souvislosti s přípravou sloučenin obecného vzorce I se nemusí slučovat s určitými funkčními skupinami, které obsahují vznikající meziprodukty. V těchto případech zabudování ochranných sekvencí a sekvencí zbavujících této ochrany nebo vnitřních konverzí funkční skupiny do syntézy napomůže získání požadovaného produktu (viz například, T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 2. vyd., Wiley: New York, 1991). Odborník v daném oboru vi, že v
01-859-99 Če některých případech po zavedení daného reakčního činidla, které je součástí kteréhokoliv konkrétního zmíněného reakčního schématu, může být pro dokončení syntézy sloučeniny obecného vzorce 1 nezbytné provést další rutinní syntetické kroky, které nejsou v těchto reakčních schématech detailně popsány. Odborník v daném oboru rovněž pozná, že v některých případech může být nutné provádět kombinaci kroků ilustrovaných ve výše uvedených schématech v jiném pořadí, než kterou schémata zachycují.'
Odborník v daném oboru si je rovněž vědom toho, že sloučeniny obecného vzorce I a zde popsané meziprodukty lze podrobit různým elektrofilním, nukleofilním, radikálovým, organometalovým oxidačním a redukčním reakcím a tím je obohatit o substituenty nebo modifikovat již existující substituenty.
Bez dalších pokusů se dá předpokládat, že odborník v daném oboru bude schopen při použití předcházejícího popisu využít vynález v jeho nejširším rozsahu. Následující příklady jsou tedy konstruovány tak, že mají pouze ilustrativní charakter a nikterak neomezují rozsah vynálezu, který je jednoznačně vymezen přiloženými patentovými nároky. Procenta představují hmotnostní procenta (% hmotn.) s výjimkou procent použitých pro chromatografické rozpouštědlové směsi, nebo není-li stanoveno jinak. Díly a procenta v případě chromatografických rozpouštědlových směsí představují, není-li stanoveno jinak, objemová procenta (% obj.). 1H NMR spektra jsou vyjádřena v ppm od tetramethylsilanu směrem dolů; s = singlet, d = dublet, t = triplet, m = multiplet a br s = široký singlet.
* · · ·
01-859-99 Če • · • · • · • · • · « <
Příklady provedení vynálezu
Příklad 1
Krok A: Příprava N-(2-methoxy-6-methylfenyl)-2,2-dimethylhydrazinkarboxamidu
Do míchaného roztoku fosgenu (108 g, 1,09 molů) v ethylacetátu (750 ml) se v průběhu dvaceti minut, při 0°C, přidal po kapkách 2-methoxy-6-methylanilin (125,0 g, 911 mmolů) rozpuštěný v ethylacetátu (250 ml). Reakční směs se pozvolna ohřála na pokojovou teplotu a potom jednu hodinu se vařila pod zpětným vařičem. Roztok se následně opět ochladil na pokojovou teplotu a za sníženého tlaku zahustil, čímž se získal surový isokyanát ve formě tmavě červené kapaliny, která se opět rozpustila v ethylacetátu (1 1) a ochladila na 0°C. Do směsi se v průběhu třiceti minut po kapkách přidal 1,1-dimethylhydrazin (55,0 g, 911 mmol), načež se směs nechala ohřát na pokojovou teplotu a míchala přes noc. Potom se směs ochladila, přefiltrovala a pevná látka se promyla ethylacetátem a po vysušení poskytla 200,0 g titulní sloučeniny kroku A ve formě bílé pevné látky, která tála při 151 až 153°C. XH NMR (CDC13) δ: 7,58 (br s,lH), 7,10 (t,lH), 6,84 (d, IH) , 6,74 (d,lH),
5,22 (brs,lH), 3,80 (s,3H), 2,63 (s,6H), 2,31 (s,3H).
Krok B: Příprava 5-chloro-2,4-dihydro-4-(2-methoxy-6methylfenyl) -2-methyl-3íf-l, 2,4-triazol-3-onu
Titulní sloučenina z kroku A (100,0 g, 447,9 mmolů) se suspendovala v ethylacetátu (11) a během tří a půl hodiny se po kapkách přidala, pomocí mechanického čerpadla, do ·· · φ φ φ φ ·» φ φ φφφ »·Φ φ ♦< · φ φ · φ φ » φ φ « »·»·»« * · t φφφ φ ·
ΦΦ φφφ φφφ Φ· ΦΦ
01-859-99 Če ·· ···· míchaného roztoku fosgenu (177 g, 1,79 molů) v ethylacetátu (1,5 1), který se ohřál na refluxní teplotu. Po přidání celého objemu se směs vařila pod zpětným chladičem další tři hodiny, načež se ochladila na pokojovou teplotu a míchala přes noc. Roztok se zahustil za sníženého tlaku a zbytek se rozpustil v ethylacetátu a vodě a čtyřikrát extrahoval ethylacetátem. Sloučené organické fáze se promyly nasyceným vodným roztokem NaCl, vysušily nad MgSO4, přefiltrovaly a po zahuštění poskytly 111(4 g titulní sloučeniny kroku B ve formě bledě žluté pevné látky tající při 132 až 134°C. XH NMR (CDC13) : δ 7,34 (t,lH), 6,93 (d,lH), 6,85 (d,lH), 3,79 (s,3H), 3,54 (s,3H), 2,20 (s,3H).
Krok C: Příprava 5-chloro-2,4-dihydro-4-(2-hydroxy-6methylfenyl) -2-methyl-3íf-l, 2,4-triazol-3-onu
Do míchaného roztoku titulní sloučeniny kroku B (15,0 g, 59,3 mmolů) v benzenu (200 ml) se při 0°C po malých částech přidal chlorid hlinitý (23,7 g, 178 mmolů). Směs se ohřála na pokojovou teplotu a dva dny míchala. Směs se nalila na led a vodu a následně čtyřikrát extrahovala ethylacetátem. Sloučené organické fáze se promyly nasyceným vodným roztokem chloridu sodného, vysušily nad bezvodým síranem hořečnatým, přefiltrovaly a po zahuštění poskytly olej, který se purifikoval mžikovou sloupcovou chromatografií na silikagelu a poskytl 13,6 g titulní sloučeniny kroku C ve formě bledě oranžové pevné látky tající při 175 až 178°C. ΧΗ NMR (CDC13) δ: 8,11 (s,lH), 6,92 (t,lH), 6,71 (d,lH), 6,41 (d,lH), 3,56 (s,3H), 2,12 (s,3H).
• · · · · ···· · · • · · · ·· · ···
01-859-99 Če • · · • · · ·· ·· « · · · ··· ··· « · • · ··· · Ί · · · · ·
Krok D: Příprava 2,4-dihydro-4-(2-hydroxy-6-methylfenyl) -5methoxy-2-methyl-3íf-l, 2,4-triazol-3-onu
Do míchaného roztoku titulní sloučeniny kroku C (133,5 g, 557,0 mmolu) v tetrahydrofuranu (1,5 1) se po kapkách přidal methoxid sodný (25 % hmotn. v methanolu, 382 ml, 1,67 molů). Směs se 3 hodiny vařila pod zpětným chladičem, načež se ochladila na pokojovou teplotu a následně naředila vodným roztokem chloridu', amonného a ethylacetátu. Vodná vrstva se okyselila (pH 4 až 5) IN HCI a třikrát extrahovala ethylacetátem. Sloučené organické vrstvy se promyly nasyceným vodným roztokem NaCl, vysušily nad bezvodým síranem hořečnatým, přefiltrovaly a po zahuštění poskytly tmavě hnědou pevnou látku, která se triturovala s ethylacetátem a poskytla 75,0 g titulní sloučeniny kroku D ve formě bílé pevné látky tající při 194 až 196°C. 3H NMR (Me2SO-d6) δ: 9,91 (s,lH), 7,17 (t,lH), 6,78 (m,2H), 3,84 (s,3H), 3,30 (s,3H), 2,03 (s,3H).
Krok E: Příprava 2,4-dihydro-5-methoxy-2-methyl-4-[6methyl-2-[3(trifluoromethyl)fenoxy]fenyl]-3H-1,2,4triazol-3-onu
Do roztoku 2,4-dihydro-4-(2-hydroxy-6-methylfenyl)-5methoxy-2-methyl-3H-l,2,4-triazol-3-onu (0,50 g,
2,13 mmolů) (připraveného podobným způsobem jako v krocích A až D) v methylenchloridu (15 ml) se přidala kyselina
3-trifluoromethylbenzenborová (0,88 g) , bezvodý octan měďnatý (0,38 g) a triethylamin (0,43 g) . Po dvacetisedmihodinovém míchání při pokojové teplotě se surová reakční směs přímo podrobila mžikové chromatografické purifikaci (silikagel, 30 % až 38 %
01-859-99 Če • · · · · ·· · ······ • · · ··· · · • ··· · · ·· ·· ethylacetátu v hexanu) a poskytla titulní sloučeninu (0,39 g, 47% výtěžek), tj. sloučeninu podle vynálezu, která tála při 95 až 96°C. NMR (CDC13) δ: 7,35 (m,3H), 7,14 (m,3H), 6,86 (d,lH), 3,82 (s,3H), 3,37 (s,3H), 2,28 (s,3H).
Příklad 2
Krok A: Tris(4-trifluoromethoxyfenyl)bismut '·
Roztok 4-(trifluoromethoxy)bromobenzenu (Maybridge Chemical Co., 200 g) v 830 ml bezvodého diethyletheru se pod dusíkem pomalu přidal do hořčíkových hoblin (20,2 g) tak, aby se udržel mírný var pod zpětným chladičem potom, co se iniciovala Grignardova reakce. Reakční směs se vařila pod zpětným chladičem dalších čtyřicet minut, načež se ochladila na 4°C. Do reakční směsi se potom po kapkách přidal roztok trichloridu bismutitého (Aldrich Chemical Co., 74,6 g) v tetrahydrofuranu (400 ml) tak, že se teplota udržovala pod 12°C. Reakční směs se nechala ohřát na pokojovou teplotu a míchala se další 1 hodinu. Potom se při 5°C přidal vodný roztok nasyceného chloridu amonného (80 ml), čímž se ukončila reakce. Reakční směs se přefiltrovala a filtrát se zahustil ve vakuu a poskytl jantarově žlutohnědý olej, který se při teplotě ledové lázně extrahoval několika částmi hexanu. Pevné látky izolované filtrací se extrahovaly diethyletherem (800 ml) . Hexanový extrakt se následně sloučil s diethyletherovými extrakty a zahustil ve vakuu za vzniku surové polopevné látky, která se triturovala s hexanem při teplotě suchého ledu. Triturovaná pevná látka se následně extrahovala vroucím hexanem a hexanový extrakt se zahustil ve vakuu za
01-859-99 Če ·· ··· ·· · · · • ·
71 | |||
vzniku | 74 g titulní | sloučeniny. 1H NMR (CDC13) | δ: 7,71 |
(d,6H), | 7,25 (d,6H). |
Krok B: Příprava 2,4-dihydro-5-methoxy-2-methyl-4-[6methyl-2-[4(trifluoromethoxy)fenoxy]fenyl]-3H1,2, 4-triazol-3-onu
Do roztoku 2,4-dihydro-4-(2-hydroxy-6-methylfenyl)-5methoxy-2-methyl-3H-l,2,4-triazol-3-onu (0,50 g,
2,13 mmolů) (připraveného podobným způsobem jako v krocích A až D Příkladu 1) v methylenchloridu (15 ml) se přidala titulní sloučenina z kroku A Příkladu 2 (2,32 g), bezvodý octan mědhatý (0,38 g) a triethylamin (0,36 g) . Po dvacetipětihodinovém míchání při pokojové teplotě se surová reakční směs přímo podrobila mžikové chromatografické purifikaci (silikagel, 30 % ethylacetátu v hexanu) a poskytla titulní sloučeninu (0,50 g, 59% výtěžek), t j . sloučeninu podle vynálezu, která tála při 75 až 77°C. ΐ NMR (CDC13) δ: 7,28 (t,lH), 7,15 (d,2H), 7,08 (d,lH),
7,00 (d,2H), 6,81 (d,lH), 3,86 (s,3H), 3,37 (s,3H), 2,27 (s,3H).
Příklad 3
Příprava 2, 4-dihydro-5-methoxy-2-methyl-4-[6-methyl-2-[3methylfenyl)methoxy]fenyl]-3H-1,2,4-triazol-3-onu
Do roztoku 2, 4-dihydro-4-(2-hydroxy-6-methylfenyl)-5methoxy-2-methyl-3íf-l, 2,4-triazol-3-onu (0,24 g, 1 mmol) (připraveného podobným způsobem jako v krocích A až D Příkladu 1) v tetrahydrofuranu (25 ml) se za stálého
01-859-99 Če míchání přidal hydrid sodný (0,05 g, 60% olejová disperze promytá hexany a suspendovaná v 10 ml tetrahydrofuranu). Po dvaceti minutách se do směsi přidal a-bromo-m-xylen (0,.14 ml) a výsledná směs se při pokojové teplotě míchala 66 hodin. Reakce se zastavila přidáním 20 ml vody a směs se extrahovala ethylacetátem (3x20 ml). Sloučené organické fáze se vysušily nad bezvodým síranem hořečnatým a po zahuštění ve vakuu poskytly titulní sloučeninu, tj . sloučeninu podle vynálezu, (0,22 g) ve formě oleje. 'H NMR (CDC13) δ: 7,24 (m,2H), 7,1 (m,3H), 6,85 (m,2H), 5,03 (s,2H), 3,88 (s,2H), 3,45 (s,3H), 2,35 (s,2H), 2,22 (s,3H).
Příklad 4
Příprava 2,4-dihydro-5-methoxy-2-methyl-4-(2-methyl-6fenoxyfenyl)-3H-1,2,4-triazol-3-onu
Do roztoku 2,4-dihydro-4-(2-hydroxy-6-methylfenyl)-5methoxy-2-methyl-3íf-l, 2,4-triazol-3-onu (1,0 g, 4,26 mmolu) (připraveného podobným způsobem jako v krocích A až D Příkladu 1) v methylenchloridu (20 ml) se přidal trifenylbismut (Aldrich Chemical Co., 3,76 g), bezvodý octan měďnatý (0,77 g) a triethylamin (0,86 g) . Po dvacetijednahodinovém míchání při pokojové teplotě se surová reakční směs přímo podrobila mžikové chromatografické purifikaci (silikagel, 30 % ethylacetátu v hexanu) a poskytla titulní sloučeninu (0,92 g, 70% výtěžek), tj. sloučeninu podle vynálezu, která tála při 58 až 60°C. XH NMR (CDC13) δ: 7,28 (m,3H), 7,06 (m,2H), 7,00 (m,2H), 6,79 (d,lH), 6,79 (d,lH), 3,86 (s,3H), 3,38 (s,3H),
2,27 (s,3H).
• * » ·
01-859-99 Če
Příklad 5
Krok A: 2, 4-dihydro-5-methoxy-2-methyl-4-[2-methyl-6-[(3nitro-2-thienyl)oxy]fenyl]-3H-1,2,4-triazol-3-on
Míchaná směs 2-chloro-3-nitrothiofenu (5,5 g, 33,62 mmolů), 2,4-dihydro-4-(2-hydroxy-6-methylfenyl)-5methoxy-2-methyl-3H-l,2,4-triazol-3-onu (7,9 g, 33,62 mmolů) a uhličitanu draselného (13,94 g, 100,86 mmolů) v bezvodém acetonitrilu (67 ml) se ohřála pod dusíkovou atmosférou na 80°C a při této teplotě se udržovala šest hodin. Reakční teplota se přes noc nechala ochladit na pokojovou teplotu. Potom se reakční směs zahustila za sníženého tlaku a zbytek se rozdělil mezi vodu a ethylacetát. Vodná vrstva se extrahovala třemi díly ethylacetátu. Sloučené ethylacetátové vrstvy se vysušily nad bezvodým síranem sodným a zahustily za sníženého tlaku, čímž se získalo 10,1 g sloučeniny ve formě hnědé, pevné látky. Tato pevná látka se triturovala s hexany a po přefiltrování poskytla 9,44 g titulní sloučeniny kroku A ve formě hnědé, pevné látky tající při 184 až 186°C. 1H NMR (CDC13) δ: 7,37 (d,lH), 7,37 (t,lH), 7,23 (d, IH) , 7,07 (d,lH), 6,69 (d,lH), 3,95 (s,3H), 3,38 (s,3H), 2,31 (s,3H). Vodná vrstva se dále extrahovala třemi díly dichloromethanu. Sloučené extrakty se sušily nad bezvodým síranem hořečnatým a po zahuštění za sníženého tlaku poskytly 0,9 g světle hnědé pevné látky. Tato pevná látka se triturovala s hexany a po přefiltrování poskytla 0,76 g titulní sloučeniny kroku A ve formě šedé pevné látky tající při 199 až 200°C.
01-859-99 Če
Krok B: 2,4-dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(2thienyloxy)fenyl]-3H-1,2,4-triazol-3-on
Do mechanicky míchaného roztoku titulní sloučeniny kroku A (3,0 g, 8,29 mmolů) v kyselině octové ' (96 ml) a vodě (13 ml), ohřátého na 75°C, se pod dusíkovou atmosférou, po částech přidalo práškové železo (1,53 g, 27,42 mmolů). Reakční směs se ohřála na 75 až 80°C a při této teplotě se udržovala 45 minut, načež se její teplota zvýšila na 80 až 90°C a při této- teplotě se udržovala další tři a půl hodiny. Potom se reakční směs ochladila (ledová lázeň), naředila vodou a dichloromethanem a přefiltrovala přes polštářek Celite. Vrstvy filtrátu se separovaly. Organická vrstva se promyla jedním dílem nasyceného vodného roztoku NaHCO3, vysušila nad bezvodým síranem sodným a po zahuštění za sníženého tlaku poskytla 2,4 g tmavé pevné látky. Do míchaného roztoku této pevné látky v bezvodém tetrahydrofuranu (129 ml), ochlazeném na 0°C, se pod dusíkovou atmosférou přidal koncentrovaný vodný roztok kyseliny chlorovodíkové (3,24 ml) a následně n-butylnitrit (0,87 g, 8,45 mmolů). Po uplynutí jedné hodiny se při 0°C přidal 50% hmotn. vodný roztok kyseliny hypofosforečné (1,11 g, 8,41 mmolů). Reakční směs se přes noc nechala ohřát na pokojovou teplotu. Potom se reakční směs zahustila za sníženého tlaku a zbytek se purifikoval mžikovou chromatografíí na silikagelu (3:7, ethylacetát:hexan) a poskytl hnědý olej. Tento olej se dvakrát rozpustil v toluenu a zahustil za sníženého tlaku a výsledný zbytek po vysušení ve vakuu poskytl 113 mg titulní sloučeniny kroku B, t j . sloučeniny podle vynálezu, ve formě hnědého oleje. Rf=0,25 (silikagel, 2:3 ethylacetát:hexan); a Rjř=0,45 (silikagel, 2:1 ethylacetát:hexan) . 1H NMR (CDC13)
01-859-99 Če ··· ··· ·· • · ··· · · · ·· ·· δ: 7,26 (t,lH), 7,05 (d,lH), 6,91 (d, IH) , 6,77 až 6,83 (m,2H), 6,55 (dd,lH), 3,93 (s,3H), 3,45 (s,3H), 2,27 (s,3H).
Příklad 6
4-[2-[(5-bromo-2-thienyl)oxy]-6-methylfenyl]2,4-dihydro-5methoxy-2-methyl-3H-l,2,4-triazol-3-on
Do míchaného roztoku titulní sloučeniny kroku B v Příkladu 5 (43 mg, 0,136 mmolu) v Ν,Ν-dimethylformamidu (1 ml) se při pokojové teplotě a pod dusíkovou atmosférou přidal nejprve N-bromosukcinimid (30 mg, 0,142 mmolu) a následně 2 kapky ředěného roztoku kyseliny bromovodíkové v Ν,Ν-dimethylformidu (připravený přidáním 2 kapek 48% vodného roztoku kyseliny bromovodíkové do 1 ml N,Ndimethylformamidu). Po dvou hodinách při pokojové teplotě se reakční směs naředila vodou a následně ethylacetátem. Vrstvy se separovaly a vodná vrstva se extrahovala dvěmi díly ethylacetátu. Sloučené organické vrstvy se promyly třemi díly vody a následně jedním dílem nasyceného vodného roztoku chloridu sodného. Po vysušení nad bezvodým síranem sodným se organická vrstva zahustila za sníženého tlaku a poskytla olej, který obsahoval určitý podíl NzN-dimethylformamidu. Tento olej se rozpustil v ethylacetátu a výsledný roztok se promyl čtyřmi díly vody a jedním dílem nasyceného vodného roztoku chloridu sodného. Po vysušení nad bezvodým síranem sodným se organická vrstva zahustila za sníženého tlaku na olej, který se rozpustil v dichloromethanu, po opakovaném zahuštění se vysušil ve vakuu a poskytl 46 mg titulní sloučeniny z Příkladu 6, tj . sloučeniny podle vynálezu, ve formě hnědého oleje.
01-859-99 Če XH NMR (CDC13) δ: 7,28 (t,lH), 7,07 (d,lH), 6,95 (d,lH), 6,79 (d,lH), 6,35 (d,lH), 3,94 (s,3H), 3,45 (s,3H), 2,26 (s,3H).
Zde popsanými postupy, dohromady s metodami známými v daném oboru, lze připravit následující sloučeniny, jejichž výčet uvádí Tabulky 1 až 13. V tabulkách jsou použity následující zkratky: t = terciální, i = iso, F = fluor, Cl = chlor, Br = brom, I = jod, Me = methylová skupina, Et = ethylová skupina, Pr = propylová skupina, i-Pr = isopropylová skupina, Bu = butylová skupina, CF3 = trifluoromethylová skupina, SCF3 = trifluoromethylthioskupina, SCHF2 = difluoromethylthioskupina, OMe = methoxyskupina, OCF3 = trifluoromethoxyskupina, 0CHF2 = difluoromethoxyskupina, SMe = methylthioskupina, (CH3)3Si = trimethylsilylskupina a CN = kyanoskupina.
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£ | 1 | 1 | 1-1 | ο | Ο | ι—I | tu | φ | CM | -Η | ||
o | a | Η | ο | Ρ | CO | ο | Ο | 2 | —' | μ | ||
1 | ι | 1 | 1 | I | 1 | 1 | 1 | 1 | 1 | >1 | V | |
P | Ρ | Ρ | Ρ | CO | Ρ | a | L0 |
Ρ
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Ρ | Ρ | ,—1 | β | ||||||||||
β φ | β -β | >1 γ· | 1—1 Ρ | ο β | |||||||||
Ρ | Ό | Χρ Η | β | 1—1 | |||||||||
I | -β | Ή | Ρ | ||||||||||
Φ | ι—1 | β | ♦Η | Ό | β | I—I | Ρ | ||||||
>ο | Ρ | -β | μ | •β | β | ι—1 | Ρ | Ρ | |||||
1—1 | 1-1 | ι—1 | X | β | β | Ρ | Ρ | β | β | ||||
σ | Ρ | Ρ | Ρ | φ | Ρ | κι a I | Ρ | 1 | β | φ | φ | ||
σ | β | β | β | a | a | a | Ρ | -β | ι—1 | Ρ | |||
ι | I | φ | φ | φ | 0 | ι | Ρ I | ι | Ό | φ | 1 | ||
σ | Ο 1 | Ρ | Ρ | Ρ | 1—I | Ρ | Ρ | -β | Ρ | β | |||
Ρ | 1-1 | 1 | 1 | 1 | a | I | η | I | Ρ | a | |||
00 | Ρ | φ | φ | φ | Ρ | 1—1 | a | φ | CM | -β | φ | I | |
ι | II | β | υ | υ | υ | β | β | Ρ | |||||
1—I | φ | 1 | 1 | 1 | ι | ι | ι | I | 1 | Ρ | 1 | 1 | |
ο | Ρ | Ρ | Ρ | sr | Ρ | Ρ | co | Ρ | a | Ρ | Ρ |
pyrazinyl
-SCF3-fenyl 4-t-Bu-fenyl 3,5,-di (CF3)-fenyl
-CF3-6-Me-2-pyridinyl 4-SCF3-fenyl 5-CF3-2-thiazolyl • · · ·
VO 00 τ—l
01-859-99 Če
1—1 | 1—1 £ | 1—1 £ | |||||||||||||
£ | 1—1 | i—1 | 1—1 £ | ||||||||||||
1—1 0 | o N | 0 N | 1—1 | ||||||||||||
1-1 | N fti | cd •H | 1-1 | l—1 | (d •H | i-1 Si £ Φ 4-1 I | £ β | β Φ | |||||||
£ | -β | d | >1 | £ | Φ | d | |||||||||
1—1 | a | <-*—1 1 1 | r-4 | I—1 | X I | a | 1—l | 1—1 | a | a | 1-1 | 1—1 | 1—1 | 1-1 | |
o | a | 4—' I | O | O | 1 | £ | £ | £ | a | £ | £ | £ | £ | ||
N | 1 | a I | N | N | CN I | β | β | β | 1 | β | β | β | β | ||
(ti | a | (ti | 1 | o | Φ | Φ | φ | a | Φ | Φ | Φ | Φ | |||
-H | 1 | (N | •d | H | Φ £ a I | o III | III | -d | •β | •β | 1 | -β | -H | -β | β |
a | β | a | X | a | a | a | a | i—1 | a | a | a | a | |||
a 1 | PQ 1 | o 1 | X 1 | a 1 | o | III o | a 1 | a 1 | a 1 | o 1 | a 1 | a 1 | a 1 - | a 1 | |
a | a | a | CN | a | oi | a | a | a | a | a | a | a | a | ||
1 | 1 | 1 | 1 | 1 | Ol | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | |
E | o | φ | 1—1 | E | Pm | O | A | i—1 | φ | β | φ | 1—1 | t—1 | φ | β |
O I | £ I | £ | | o | | O I | O I | I | I | o | | £ I | m | | £ I | o I | o | | £ I | CQ I |
1 a | 1 | 1 | 1 | 1 | 1 | 1 CO | 1 CO | a | I | 1 | 1 | a | a | 1 d | 1 |
i—1 | £ | 1-1 | £ | 1—1 | |||||||||||
>1 | 1-1 | £ | rd | £ | |||||||||||
o | _I | i—1 | o | β | 1—1 | 1—1 | i—1 | i—1 | |||||||
•d | N | O | N | Φ | >1 | £ | £ | Í>1 | |||||||
d | (ti | l-1 | Kd __1 | N | (ti | a | c | β | β | c | |||||
-β | -β | £ | (ti | •β | 1 | Φ | Φ | Φ | Φ | ||||||
β | a | I—1 | CJ M | -β | a | r—1 | -d | 1—1 | •β | -β | •d | ||||
£ | a | o | fd | a | a | £ | o | XI | 1—1 | £ | a | a | XI | 1—1 | |
Ρ | 1 | N | •d | a | 1 | β | III | X | £ | β | a | a | X | £ | |
I | a | (ti | d | 1 | a | Φ | o | 1 | β | Φ | 1 | 1 | 1 | β | |
l—1 | a | 1 | -β | o ll | a | 1 | a | -β | CN | Φ | ♦d | a | a | co | Φ |
I>1 | I | -β | a | -θ' I | 1 | E | 1 | a | 1 | •d | a | 1 | 1 | l | •d |
β | φ | a | a | 1 CN | H | O | n | o | a | a | φ | H | u | a | |
Φ | £ | F | 1 | I | 1 | 1 | o | (N | a | 1 | £ | 1 | a | ||
a | •d | M | a | oi | a | a | III | E | 01 | 1 | a | •β | a | Ol | 1 |
1 | Ό | E | 1 | E | 1 | 1 | o | O | K | a | 1 | d | 1 | K | a |
E | 1 | O | Φ | O | φ | Φ | E | o | 1 | 1—1 | 1 | φ | o | 1 | |
O 1 | co | £ I | a I | £ I | £ I | I | | | | | H I | o I | a | £ 1 | 1 | H I | |
1 a | 1 a | 1 a | 1 a | i | 1 | 1 a | a | Lf) | a | -^1 | Lf) | a |
£ | l—1 | ||||||
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I-1 | o | r—1 | |||||
I>1 | N | O | |||||
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iH Q | £ | 1—1 | -β | (ti | £ | £ | |
N | 1—1 | £ | a | -β | i—1 | Γ—1 | |
fd | o | r—l | a | a | o | o | |
*d | N | O | 1 | a | N | N | |
^β | X | (ti | N | a | 1 | (0 | (0 |
β | r*—( | 1 | •β | (ti | 1 | a | •β | •β |
'(ti | I | a | -β | I—1 | 1 | a | a |
> | CN | a | a | o | φ | a | a |
O | | | 1 | a | 1 | £ | 1 | 1 |
>u | oi | a | 1 | a | -β | a | a |
(ti | tm | 1 | a | 1 | d | 1 | 1 |
β | O | H | 1 | φ | 1 | β | φ |
a | O | O | H | £ | a | m | £ |
0 | 1 | 1 | 1 | 1 | 1 | 1 | |
p | LO | a | a | -3* | •31 |
i—1 £ β Φ | 1—1 Í>1 a | 1—1 a φ | ||||||
1—1 | a | φ | •d | |||||
£ | 1 | i—1 | i—1 | •d | a | 1—1 | 1-1 | |
Γ—1 | —- | £ | £ | X | 1—1 | a | £ | £ |
0 | o | β | β | X | £ | 1 | β | β |
N | III | Φ | Φ | 1 | β | a | Φ | Φ |
(ti | o | d | •d | CN | Φ | 1 | β | •d |
•β | u | a | a | 1 | •β | β | a | a |
a | oi | a | a | O | a | CQ | a | a |
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1 | E | a | a | oi | 1 | a | a | a |
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1 | φ | β | O | 1 | Φ | Φ | β | |
H I | I | £ I | m t | 1 | H I | £ | | £ 1 | m I |
1 | 1 OO | 1 LO | LO | 1 | 1 | 1 | LO | 1 LO |
(CH3) 3C-3-thienyl 4-Cl-3-thienyl 4-Me-5-Cl-3-thienyl
I-3-thienyl 4,5-diMe-3-thienyl 2-Cl-3-thienyl de-5-Br-3-thienyl 4-Me-5-I-3-thienyl r~
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l-1 | TJ | a | 1 | a |
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a | CO | CO | co | M1 |
l—1 Sl | i—1 >1 £ | |||
i—1 | i—1 | £ | •H | |
tí | tí | •H | Ť5 | |
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tí tí | tí tí | a | | tí CD | Si Cb |
a | a | CM | a | M-1 1 |
1 co | 1 co | 1 ro | 1 tí | CM i |
1 | 1 | Cm | a | ro |
CD | CD | O | 1 | Cm |
£ I | £ I | O t | a I | O I |
1 CO | 1 (O | 1 CO | CO | 1 |
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tí | tí | tí | Sl | >1 | TJ | £ | tí | 1—i | tí | |
tí | £ | g | £ | £ | •H | •μ | -tí | tí | tí | |
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a 1 | a I | a I | TJ * μ | TJ -μ | tí a | H £ | -tí g | -tí TJ | a 1 | |
tí | ro | ,—I | ro | μ | μ | 1 | H | -H | -tí | CD |
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Lf) | Mi | 1 | Mi | | | | | •H | CM | co | co | 1 |
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£ | | £ I | O I | £ I | U i | O I | LO | O I | o I | £ i | ro |
CM | CM | CO | CM | 1 | 1 CO | CO | 1 | 1 | 1 CO | co |
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tí | CD | TJ | •μ | -μ | -tí | a | -tí | |||||
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Tj | 1 | 1 | 1 | ro | 1 | 1 | 1 | LO | 1 | l | ||
1 | CD | CD | CD | Cm | CD | CD | l-1 | a | 1-1 | |||
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CO | CM | co | 1 LO | LO | Mi | LO | CO | CO | Mi | |||
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tí | M-l | 1—| | tí | tí | -tí | •tí | ||||||
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a | rt | >1 | | | 1 | 1 | rt | tí | -tí | ||||
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o | tí | 1—1 | Cm | a | Mi Φ | 2 | 1 | 1 | tí | CD | tí | |
CM | tí | o | O | | | Μμ | I | CD | CD | a | a | a | |
a | CD | 1 | CM | | | LO | £ | £ | 1 | rt | 1 | ||
o | a | Lf) | •H | a | ro | I | •μ | μ | co | a | co | |
1 | 1 | 1 | Ό | a | Cm | ro | TJ | TJ | 1 | a | 1 | |
CD | CD | 1 | u | O | a | 1 | 1 | 1—1 | rt | I—1 | ||
II | £ | £ | LO | o | O | o | LO | LO | O | tí | o | |
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tí | X | d | X | tí | Φ | >1 | tí | >1 | |||
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-β β
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I—1 | |||
Rt | |||
i—l | β | ||
Rt | -β | ||
rp | β | Τ | |
>Ί | Φ | -β | |
1-1 | £ | 2 | β |
Rt | >—I Q) | 1 | Ri |
β | 4-1 | i—! | a |
Φ | 1 | o | ι |
2 | m | -P | a |
1 | a | T | 1 |
Φ | o | 1 | φ |
2 | o | a | 2 |
ι | 1 | X. | ι |
tf | tf | a | tf |
01-859-99 Če
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β
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tu|
a 1 tf | T 1 a | a o o | T 1 co | | | ||||
X | 1 | X | 1 | |||||
CM | a | a | m | |||||
1—1 | 2 | |||||||
Rt | U | |||||||
β | ||||||||
-β | o | |||||||
Τ | i—1 | II | tul | 1-1 | ||||
-β | 1 | Ri | 2 | Si | ||||
β | CM •C | l—1 | I—1 | β | 1 | r—1 | £ | i—1 |
Ri | k-M Γ > | Ri | Φ | 2 | Rl | <D | Si | |
a | c> CM | 1 tul β | β | 1—1 | II | β | 4P | β |
I | 2 | φ | Φ | (ti | 2 | Φ | | | Φ |
a | U | 2 | 2 | 2 | O | 2 | 2 | |
ι | 1 | 1 | 1 | 2 | 1 | 1 | tu | 1 |
φ | Φ | rH | (ti | Φ | O | 1—1 | ||
2 I | II | 2 | | u | | β i | II | 2 1 | O I | o I |
1 a | >H | CM | 1 | a | R( | co | CO | tf |
I—I Ri β -β Τ β β ί>Ί a ι a ι ro a o i
a a
-naftalenyl 4, 6-diMe-2-pyridinyl 3-Et-fenyl
Ρ | |||||
ι—1 | β | ||||
1-1 | Ρ | Ή | |||
>1 | β | Ό | |||
-β | -Η | ||||
•Η Ό | Ό -Η | g -Η | |||
1-1 | Ή | β | β | ||
1-1 | Ρ | μ | Ρ | Ρ | |
κ=Ί £ | β φ | κθ a | a I | a I | |
φ | Ρ | ί CM | Ρ 1 | Ρ 1 | |
4-1 | 1 | ||||
1 | Γ0 | 1 | Γ0 | η | |
1-1 | a | Φ | a | a | |
ο I | ο I | (Ρ a ο | Σ I | ο | υ I |
1 00 | 1 | 1 | 1 Ρ | 1 <0 |
Ν|
Ρ
1-1 | β | |||
Ρ | •β | |||
β | Ό | |||
•Η | -β | |||
1-1 | Ό -Η | g -β | ||
1-1 | Ρ | β | β | |
1-1 | Ρ | β | Ρ | Ρ |
>1 α | β φ | Φ Ρ | a ι | a ι |
φ 4-1 | Ρ 1 | 1 β | Ρ 1 | Ρ 1 |
1 | ω | a | ω | (Ό |
I—1 | a | I | a | a |
υ I | ο I | Ρ I | υ I | ο I |
00 | 1 | 1 | ρ. | •sf |
I-1 >1 tM| β φ ρ ι φ
£
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Ό ι
ρ
Ρ Ρ Ρ κ—I ρ
1-1 | β | |||
Ρ | -β | |||
β | Ό | |||
•β | -β | |||
τ) | g | |||
ι—1 | 1—1 | -β | •β | |
ι—1 | Ρ | >1 | β | β |
Ρ | β | Ρ | Ρ | |
β | Φ | φ | a ι | a ι |
φ | Ρ | 4-4 | ||
Ρ 1 | 1 η | 1 3 | Ρ 1 | Ρ 1 |
(Ό | a | m | η | (Ό |
a | ο | I | a | a |
ο I | ο | | 4J ι | υ I | υ | |
1 Ρ | 1 | I κΤ | 1 | 1 |
Ν| ι-1
Ρ β
-Η
1-1 >1 | Ό -β | |||
1-1 | β | β | ||
Ρ | β | Ρ | ||
β | 1—I | Ό | a | |
φ | 1-1 | Ρ | •β | ι |
Ρ | >1 | β | β | Ρ |
1 | £ | φ | Ρ | ι |
φ | φ | 1—I | a | φ |
£ | 4-4 | φ | ι | £ |
-Η | | | Ρ | Ρ | •Η |
Ό | (Ρ | Ρ | ι | TJ |
I | tu | φ | φ | 1 |
Ρ | ο | β | £ | <0 |
V | 1 | 1 | ι | κ |
00 | 00 | Ρ | co |
ι-1
Ρ β
-Η
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Ρ|
I—I Ρ β φ Ρ I ι φ 1 £
I a υ ο a
1-1 | β | β | ||
Ρ | -Η | Ρ | ||
β | ,—I | 1-1 | Ό | a |
φ | >1 | Ρ | •β | ι |
Ρ | β | β | β | Ρ |
1 | Φ | φ | Ρ | ι |
1-1 | 4-4 | ι-1 | a | φ |
υ | | | φ | ι | £ |
-β | (Ρ | 4-> | Ρ | -Η |
τ) | tu | Ρ | ι | Ό |
ι | Ο | φ | φ | I |
Ρ | Ο | β | £ | co |
1 | 1 | I | ||
Ρ | 00 | Ρ | CO |
Ρ
i—i | β | ||
Ρ | -β | ||
β | γ~4 | Ό | |
φ | >1 | -β | |
ι—1 | Ρ | d | β |
Ρ | I | Χρ Φ | Ρ |
β | ι-1 | Ψ4 | a |
φ | ο | | | ι |
Ρ | -β | η | Ρ |
1 | Ό | tu | 1 |
φ | 1 | Ο | φ |
£ | Ρ | Ο | £ |
I | ι | I | |
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Ρ β
Η
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-Η β
Ρ a
I
Ρ
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φ | II | Ν| |
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σ | ο | Ρ |
σ | Μ | β |
I | a | φ |
σ | ο | Ρ |
Ρ C0 | I | 1 φ |
ι Ρ | II | £ I |
ο | Ρ | Ρ |
1—1 Ρ β φ Ρ 1 | 1—1 Ρ β -Η Ό -β | 1—1 Ρ β •Η Ό Ή μ | I ω a ο a | |
1-1 | η | β | I | |
Ρ | a | Ρ | Oj | | a |
β | υ | a | II | |
φ | ι | CM | a | |
Ρ | -Η | Ρ | | | ο |
1 | Ό | ι | <*> | I |
f—1 | 1 | g φ | tu | |
υ 1 | Ρ | a £ 1 I | Ο I | II |
1 | Ρ | 1 1 4-) Lf) | 1 <0 | Ρ |
Η | ||||
ι—1 Ρ β | >1 •μ | |||
1—1 | -β Ό | Ό •Η | ||
>1 | -β | μ | ||
ι—1 | ι—1 | £ | β | >1 |
Ρ | Ρ | φ | Ρ | Oj |
β | β | 4-ι | a | ι |
φ | φ | | | ι | CM |
Ρ | Ρ | ρο | Ρ | j |
I | 1 | tu | 1 | ω |
φ | 1—1 | Ο | φ | tu |
£ } | υ I | Ο I | £ I | Ο ι |
00 | 1 | 00 | L0) |
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Lf) t—I
1—1 a 2 •H | 1-1 a 2 -2 | r—1 a 2 -H | i—1 a 2 -H | ||||
1-1 | T | T | k| a | T | T | ||
>1 | -2 | -2 | a | -2 | •2 | ||
Cl | 1—1 | 2 | 2 | rt | i—1 | 2 | 2 |
X-i Φ | a | a | a | 2-1 Φ | a | a | a |
M-4 | 2 | a | a | a | 2 | a | a |
j | Φ | 1 | 1 | | | ω | 1 | 1 |
n | a | CN | CN | n | a | CN | CN |
Pq | 1 | 1 | 1 | £ | 1 | 1 | 1 |
O | Φ | Φ | ω | O | ω | ω | ω |
O | | £ I | £ | | £ I | O | | £ I | £ I | £ I |
CO | CO | 1 LO | LO | CO | (O | LO | LO |
>1 i—l -H a Ό k| a d Η -η
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φ ' ® £
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£ | T | a | 1 rn | £ | T | a | 1 m |
O | 1 | 2 | £ | O | 1 | 2 | £ |
O I | LO | 2 I | O 1 | O I | LO | 2 I | O | |
1 | co | 1 CN | 1 Lf) | 1 | co | CN | Lf) |
i—I | i—1 | ||||||
a | a | ||||||
2 | 2 | ||||||
-H | •H | ||||||
T | T | ||||||
•2 | -2 | ||||||
i—( | 2 | 1-1 | 2 | ||||
a | a | a | a | ||||
2 | a | cx]| | 2 | a | |||
r-4 a £ | I-1 a | φ a 1 | 1 CN 1 | l—1 a | i—1 a | φ a 1 | 1 CN 1 |
Φ | 2 | φ | φ | Φ | 2 | φ | Φ |
Ψ4 I | φ | £ | £ | a I | Φ | £ | £ |
a | -H | -H | a | •H | •H | ||
1 <*> | 1 | T | TJ | <O | 1 | T | TJ |
Pq | i—! | 1 | 1 | £ | I-1 | 1 | 1 |
O | o | LO | LO | O | o | lO | LO |
l | 1 | 1 | 1 | ||||
co | a | CO | CO | a | CO | ΤΤ1 |
01-859-99 Če ω
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i—1 a 2 φ a I | 1—1 a 2 φ a | l-1 a 2 φ a | 1—1 a 2 Ή T Ή 2 a a 1 CN | Φ | i—1 a 2 -2 T -2 2 a a 1 CN | |||
ω II O O CM £ O | κι | |||||||
1—1 a 2 φ a 1 | i—1 a 2 φ a | a a 2 φ a | ||||||
ΓΊ | I | 1 | 1 | 1 | (*) | 1 | 1 | 1 |
£ | i—1 | φ | φ | £ | 1-1 | φ | Φ | |
O I | o | | £ I | £ J | II | O I | u | | £ 1 | £ | |
1 | co | 1 | 1 | a | a | CO | a | a |
N|
X
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1—1 | rd a | i—1 | Y | |
a | β | >? | a | β |
β | CD | β | CD | |
CD | a | G | CD | a |
a I | 1 co | (D a | a I | 1 co |
1 CO | X | 1 | 1 <ra | X |
X | o | ω | X | o |
o I | o I | o I | o | | |
ra | 00 | ra | 1 | 1 |
l-1 | i—1 | Y g a |
a | a | 1 |
β | β | a |
CD | CD | o |
a | a 1 | J |
1 Jí | 1 rd | o 1 |
£ | o | LO |
1 | 1 | s. |
ra | ra | ra |
I I I I I I
β X N β > | γ X o & ¾ υ í o x1 | a & β & 1 Ϊ o XI X | i—1 ah X 8 & 3 a o Ϊ o x1 | 1-1 a*1 X 8 & á a υ Ϊ o x1 | i—1 Í>1 X o β X o u í o x1 | |-1 a*1 X 8 X o d a u Ϊ o x1 | i—1 a X o β X o d a υ Ϊ o x1 | Y X o β X o i u l 1 o ίβ1 |
>β | o | o | o | u | o | o | o | o |
X | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
N| β
X x1 ž
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& CD a 1 | Y g | Yi g a 1 | £ CD a I | Y g | 1-1 a β CD |
1 <*) | a | 1 <*> | a | a | |
X | 1 | 1 <*> | X | 1 | 1 |
o | CD | X | o | CD | a |
o | | o | | o i | o | | ||
00 | ra | 1 ’χτ1 | 1 | ra |
ω a
i a
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LO ra
01-859-99 Če ai <xm<xrx<XfO<XfO
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Φ | C-i Φ a 1 | 1—i | |
a | X | ||
1 Φ | β | 1—1 | |
0) | X | ||
2 | řO | a | β |
•rd | 2 | 1 | Φ |
2 | O | 1—1 | a |
1 | •—- | 0 | 1 |
a | -H | •H | β |
- | 2 | 2 | 2 |
a | 1 a | 1 a | 1 a |
k | 1 | 1 | |
a | a | a |
i—1 S 0 •rd | l—1 S β | 1—1 X β -rd | |
1—1 | TJ | •rd | 2 |
X | •rd | TJ | Ή |
β | 0 | -rd | β |
Φ | >1 | 0 | X |
a 1 | On l | £>1 On | a 1 |
CM 2 | CN | | 1 CN | a 1 |
2 | ro | 1 | co |
O | On | (L) | 2 |
O 1 | O 1 | 2 1 | ω | |
i ω | 1 | 1 | 1 LD |
Tabulka 3b
O
II
2“
II
1—i X
X β | 1—1 | 1—1 >1 | 1—1 >1 | β Φ | |
Φ | >1 | 1—1 | β | £ | a |
a | 0 | X | Φ | φ | 1 |
1 | Cl) | β | a | 4-1 | 1—1 |
φ | M-d | Φ | 1 | | | 0 |
2 | | | a | β | fO | -H |
1 | Γ0 | 1 | 2 | On | 2 |
a | On | β | 1 | O | 1 |
O | 2 I | a 1 | O 1 | I | |
1 | 1 | 1 | 1 | a |
X | |
0 | |
•rd | |
TJ | |
•H μ | 1—1 |
S | X |
On i | β -H |
1 CN 1 | 2 -β |
ω 2 | β X a |
LD | | 1 a |
(2 | l |
On | φ |
O j | 2 |
CO |
X β
-H
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X a
a
CO
O
I φ
>o σ
σ ι
σ a
co i
1—I o co *1
co | 2 | 1-1 | |||||||
II | O ω | 1—1 | X β •rd | 1—1 X β | |||||
CN | O | X | 1—1 | Tí | -H | ||||
II | β | a | X | •H | 2 | ||||
»k 1 | 2 1 | 1-1 | 1—1 X | 1—1 | Φ a | X β | β Φ | 0 S | -H β |
0 CM | O CM | X β | β Φ | X β | 1 β | φ a 1 | a 1 | On | | X a |
2 | 2 | Φ | a i | Φ | 2 | CM | CN | | 1 | |
O | O | a | a | H | CO | 2 | a | ||
1 | 1 | 1 | Cl | 1 | 2 | 2 | 2 | co | 1 |
Φ | 2 | r—1 | 1 | O | O | On | Φ | ||
II | II | 2 I | 0 I | O I | a | O 1 | O | | O 1 | 2 |
X | X | 1 00 | 1 a | 1 a | a | 1 a | 1 | 1 a | a |
a , 6-diMe-2-pyridinyl 2,6-diMe-4-pyridinyl 2,6-diCl-4-pyridinyl
-0Me-2-pyridinyl 4-OMe-2-pyridinyl 4-OCF3-2-pyridinyl
-OCF3-2-pyridinyl 6-OCF3-2-pyridinyl 4-OCHF2-pyridinyl co « · · · · · κ*ϊ
Ρ •Ρ ι—I Τ! Ρί
a | ι—ι Ρί β | ι—1 Ρί β Φ X 1 CO | 1—1 Ρί β Φ | 1-1 Ρί β •Η Ό -Η Ρ ί>1 | Ρ β Ρί a 1 X 1 φ | β •Ρ Ό •Ρ β Ρί a ι | 1-1 Ρί β | |||
ι—1 Ρί | Φ X | a ο | X 1 | Λ I | 5! ι | X 1 | Φ X | ||
β | ι—1 | | | — | (Μ | CM | LO | ΟΙ | 1 | |
Φ | >1 | CO | -Η | a | | | | | a | β | |
ι—1 | β | a | Ό | a | ΓΩ | (Ο | a | a | |
Φ | φ | ο | 1 | υ | ΙΡ | a | ο | ι | |
X | X | ο | Ό | ο | ο | ο | ο | X | |
X | 1 | I | I | 1 | ι | I | 1 | ||
φ | X | β | X | X | X | CO | χ | X | X, |
β I | a ι | a I | |||||||
1 CM | I (Ό | 1 +J |
Ρί β
ω ι-1 φ
X
X φ
β
I
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1-1 , a| β Η Ό •Η | I Ο β a Ρί a | 1-1 | ||
X | Ρ | φ | Ρί | |
Ό | >1 | β | β | |
C—1 | Q, | X | I—1 | Φ |
Μ-) | | Φ | Ρί | X | |
CM | X | β | ι—1 | |
| | 1 | Φ | Ρί | |
<Ν | X | X | β | |
a | 1 | -Η | ||
a | X | Φ | a | |
ο | 5! | X | ||
ο I | X | ω I | φ 1 | |
1 | X | 1 X | I X |
1-1 | Ρί | |||||
>1 | ι—1 | β | ||||
£ | Ρί | •Ρ | ||||
1-1 | •Ρ | β | Ό | |||
Ρί | Ό | Η | Ρ | |||
|-1 | β | ι—1 | Ή | a | ρ | ι—1 |
Ρί | Φ | Ρί | Ρ | •Η | >1 | Ρί |
β Φ | X 1 | β Φ | ί>1 Πι | β Ρί | | | β Φ |
X | ι—1 | ι—1 | 1 | a | CM | X |
| | υ | Φ | CM | 1 | I | 1 |
CO | -Η | X | J | X | ΓΩ | β |
a | a | X | ΓΩ | 1 | t, | a |
ο | I | φ | t, | Φ | Ο | ι |
ο | | Ό | β I | Ο ι | 53 I | Ο I | X ι |
1 | X | X | ι Ό | 1 | 1 | 1 X |
« · ·
I · · · • 9 · · · · • · • « · ·
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Ρί | 1-1 |
β | Ρί |
Φ | β |
1-1 | Φ |
φ | X |
X | — |
X | Ρί |
φ | X |
β | Ο |
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Ρί β -Η | 1—1 Ρί β | |||
a -Ρ | •Η a | |||
1-1 | Ρ | -Η | ||
>1 | rp | Η | >1 | β |
Ρ | Ρί | Ρί | Οι | Ρί |
φ | β | β | | | a |
Φ | Φ | CM | 1 | |
I | X | X | | | X |
ΓΩ | 1 | 1 | ΓΩ | 1 |
ti | 1-1 | φ | (i | φ |
Ο I | ο | | 53 I | Ο I | 53 |
ΓΩ | 1 | 1 | 1 | 1 Lf) |
Ρί β
Η
Ό
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Ρί a
I
X
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Ρί β
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1-1 | 1 | Φ | I—I | |||||||||
>1 | O | O | I | ι—1 | Ρί | |||||||
a| | β | β | £>1 | β | ||||||||
-Η | a | O | C0 | ι—1 | £ | • p | ||||||
Ό | Ρί | β | a | Ρί | •Ρ | a | ||||||
-Ρ | a | X | υ | β | a | Ρ | ||||||
β | φ | X | — | 1-1 | X | Ρ | β | |||||
Ρί | β | X | i—1 | a | Ν| | Ρί | a | β | Ρί | |||
'•Η | a | X | β | Ρί | ο | 1-1 | β | X | Ρί | a | ||
β | | | Φ | X | β | ο | >1 | 1—1 | ι—I | Φ | β | a | | |
'φ | X | X | 1 | Φ | a | £ | Ρί | X | Ρί | ι | X | |
I | 1 | X | ι—1 | II | φ | β | β | 1 | a | X | I | |
ο | Ο] | ra | v | Φ | a | ΨΊ | φ | Φ | οι | I | | | οι |
>υ | a | X | X | ο | I | X | X | a | χ | co | a | |
φ | a | l> | s. | X | I | ΓΩ | 1 | 1 | a | I | a | a |
β | o | X | φ | ti | X | φ | υ | φ | υ | o | ||
a | o | LO | -- | β | II | Ο | U | 53 | ο | 53 | ο | o |
ο | 1 | 1 | 1 | 1 | 1 | ι | ι | ι | ι | 1 | ||
a | Ό | Ό | X | τ—1 | >4 | X | X | χ | χ | X | Ό |
CO
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r—| | Co tí φ X | | 1—1 | I-1 Co tí X T |
X rp | d | Co tí | -H tí |
Φ | X | Φ | Co |
X | o | 1-1 | X |
1 d | -H | tí X | 1 CM |
X | T | X | 1 |
o | 1 | tí | 1—1 |
o | uo | tí | o |
1 | 1 | 1 | |
co | co | CM | L!0 |
1-1 | |||
1-1 | X Co tí | i—1 Co tí | Co tí -tí T tí tí Co a |
Co | Φ | Φ | 1 |
tí | X 1 | X I | CM I |
Φ X | | 1 i—1 | Φ | Φ |
o | £ | £ | |
d | -tí | X | Ή |
X | T | T | T |
O | 1 | 1 | 1 |
o | LO | LO | LO |
1 | V. | ||
sP | co | co |
>1
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-tí | >1 | i—I | ||
tí | Co | |||
Co | Φ | tí | ||
X | M-l | -H | ||
1 | ůM | I-( | 1 | l—1 | T |
CM | S | >1 | •tí | |
1 | P | PO | P | tí |
Φ | Φ | IP | φ | Co |
£ | M-l | o | i—1 | X |
1 | | | —' | Φ | 1 |
LO | PO | •H | 4-J | CM |
1 | IP | Ό | M-l | 1 |
tí | O | 1 | Φ | i—1 |
X I | o I | Lf) | P I | o I |
1 LO | 1 CO | co | 1 C\J | 1 LO |
l—I
S
P •H
r_4 | •H | |||
>1 | T | |||
P •H | 1—1 | i—1 | -tí tí | |
Ťí | Co | Co | Co | |
•H | n | ,—[ | tí | tí | X |
p | Co | Φ | Φ | 1 |
S | tí | X | X | CM |
řP 1 | Φ | 1 | 1 Φ | 1 |
X 1 | 1—1 | Φ | ||
CM | | o | £ | £ | |
d | -tí | •H | •H | |
po | X | T | T | Ό |
IP | O | 1 | 1 | 1 |
o | | o 1 | LO | LO | LO |
LO | 1 | co | co |
1—1 Co tí •H T H | i—1 Co tí •H T •H | N| f—| | 1-1 S P •H Ό H | |||||
>1 | X | X | tí | tí | S | 1—1 | l—1 | tí |
P | Co | Co | Co | Co | £ | Co | Co | Co |
Φ | tí | tí | X | X | Φ | tí | tí | X |
M-l | Φ | Φ | 1 | 1 | MM | Φ | Φ | 1 |
| | X | X | CM | CM | | | X | X | CM |
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Co | s | tí | tí | tí | Co |
tí | P | Φ | Φ | Φ | X |
Φ | Φ | X | X | X | 1 |
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ω | co | X | X | X | d |
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tí | rtí | 1—1 | rtí | |||
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tí | 4J | X | X | P Φ | X | |
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1 | g | T | IP | N | ||
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£ 1 | tí | LQ | o | —' | tí | |
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τί •Η | -β | X | Ρ | -Η | μ | β | Ρ | |
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tu | 1 | O | I-1 | 1 | III | 1 | 2 | 1 | O | i—1 | 1 |
O | LO | ω | o | tf | 0 | LO | O | LO | CO | o | tf |
1 | 1 | 1 | 1 | 1 | K. | 1 | 1 | ||||
co | CO | co | co | co | co | CO H | CO | co | co | CO | co |
LO
O cu *1 >1
rp | 1-1 Ri | 1—1 Ri | β ω | 2l | 1—1 | 1-1 Ri | 1-1 Ri | |||||
1-1 | >1 £ | β Φ | β Φ | 2 1 | 1-1 Ri | r—1 | Ri β | β Φ | β Φ | |||
Ri | Φ | 2 | 2 | Φ | β | Rl | Φ | 2 | 2 | |||
β | 4P | 1 | | | 2 | Φ | β | 2 | l | 1 | |||
Φ | | | M | CM | 1 | 2 | Φ | | | CM | CM | |||
2 | ro | 2 | 2 | tf | 1 | 2 | σι | 2 | 2 | |||
1 | tu | 2 | 2 | 1 | Φ | 1 | 2 | 2 | 2 | |||
Φ | O | O | O | 1—1 | 2 | Φ | O | O | O | |||
2 | O | O | ω | O | ω | ω | ro | 2 | O | O | ω | |
1 | 1 | 1 | 1 | 1 | ι | 2 | 2 | 1 | 1 | 1 | 1 | |
tf | tf | tf | co | tf | O | 0 | tf | tf | tf | tf |
1—I Ri β Φ 2 I ω
i tf
I
I—I o
I co
2l
01-859-99 Če β
φ
2l
1—1 | β | 1—1 | |||||||||||
1—1 | 1—1 | Ri | 2 | 1—1 | 1—l | Si | |||||||
1—| | Ri | Ri | β | -β | 1—I | Ri | Ri | P | |||||
1—1 | >1 £ | β Φ | β Φ | Φ 2 | 1—1 Ri | 2 ω | 1—1 | Ri β | β Φ | β Φ | φ MP | ||
Ri | Φ | 2 | 2 | 1 | β | 2 | Ri | Φ | 2 | 2 | 1 | ||
β | q_l | | | | | 2 | Φ | β | ro | β | 2 | I | I | 1—1 | |
Φ | 1 | CM | CM | U | 2 | co | Φ | | | CM | CM | u | ||
2 | 1 ro | 2 | 2 | •β | 1 | 0 | 2 | σι | 2 | 2 | •P | ||
1 | 2 | 2 | 2 | T | Φ | 'Ri | 1 | 2 | 2 | 2 | Ό | ||
Φ | 0 | O | O | 1 | 2 | β | β | II | Φ | υ | O | O | 1 |
2 | 0 | O | co | LO | co | m | Τ | o | 2 | o | O | co | to |
1 | 1 | 1 | 1 | 1 | 1 | 'Ρ | H | 1 | 1 | 1 | 1 | X | |
co | co | co | co | co | co | 2 | >cu | co | co | CO | co | co |
3-SMe-fenyl 4-SMe-fenyl 3-OCH-fenyl 4-C=CH-fenyl t-Bu CF3 3,5-diF-fenyl 3-cyklopropyl-fenyl
Žádný substituent R9 (tj . H) CH3 I Br • · · · · ·
Ρΐ
Tabulka 6b
X χ
II m
Ρ
-Γ~I Ρ xl
X
β | |-1 | 1—1 | |||
rH | Φ | >1 | X | ||
d | P 1 | £ d) | 1-1 X | 1-1 X | β Φ |
φ | Φ | 4-4 | β | β | P |
4-4 | £ | I | Φ | φ | 1 |
| | •H | ro | P | P | X |
ro | Ό | tu | 1 | 1 | o |
tu | 1 | O | 1-1 | β | lil |
O I | X | ω I | o | | m I | o I |
1 | X | 1 | 1 | 1 X | 1 |
I-1
X β
ω ρ
ι ι-1
X a
o β
a o
I-1
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X υ
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r£ | ||||||
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β Φ | I—1 | |||||
P | X | I—1 | ||||
| | r—| | β | 1—1 | X | ||
(—1 | >1 | Φ | X | β | ||
ω | £ | 1-1 | P | β | Φ | |
d | P | d) | X | 1 | Φ | P |
>—< d) | o | 4-4 | β | 1—1 | P | 1 |
4-4 | — | | | Φ | o | 1 | P |
I | -H | ro | P | -β | X | -β |
1 (X | P | tu | 1 | Ό | o | P |
P | 1 | O | 1-1 | 1 | lil | 1 |
o | X | ω | o | P | o | X |
1 | 1 | 1 | 1 | |||
X | X | ro | X | X | X | X |
Η
ΡΙ
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1—1 | ι—1 | β | |||
1-1 | X | X | φ | ||
1-1 X | X β Φ | β φ Ρ | β φ Ρ | Ρ 1 φ | 1—1 X β |
β | P | | | 1 | £ | φ |
Φ | | | Μ | οι | I | Ρ |
P | n | Ρ | Ρ | Ρ | I |
1 | P | X | X | 1 | φ |
Φ | u | Ο | ο | 1-1 | £ |
£ 1 | o I | ο I | ω I | ο I | χ I |
1 | 1 ’χΡ | 1 | 1 | X | Ρ |
xl β
PQ
φ β | Xl | ι—1 | φ β | ||||||
Ρ | I—1 | 1-1 | X | Ρ | |||||
Φ | -β | 1-1 | X | X | β | •β | |||
>ο | Ρ | X | (4 | β | φ | I—1 | Ρ | ||
ω | ι—1 | β | Φ | Φ | Ρ | X | m | ||
σ | Ρ | X | φ | Ρ | Ρ | 1 | β | Ρ | |
σ | β | β | Ρ | ι | ι | Ρ | φ | β | |
1 | ω | φ | 1 | οι | ΟΙ | υ | Ρ | W | |
σ | Ρ | σ) | Ρ | Ρ | -β | 1 | |||
χ | 'X | 1 | Ρ | X | X | Ρ | φ | 'X | |
C0 | β | φ | Ο | ο | υ | 1 | £ | β | β |
I | Ρ | £ | ο | ο | X | X | X | m | Ό |
τ—1 | 'β | I | 1 | 1 | ι | ·*» | 1 | ι | 'β |
ο | >tq | χ | X | X | X | X | X | Ρ | >t<] |
X β
ω ρ
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Ρ ο
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β ω
Ρ
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Ρ
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X χ
β ω
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Ρ χΙ ι—I X β φ Ρ ι φ £ ι
-OCF3-fenyl 4-OCF3-fenyl 3,5-di(CF3)-fenyl 3,5-diMe-fenyl
-0CHF2-fenyl 4-OCHF2-f enyl 3-SCF3-fenyl 4-SCF3-fenyl • · · · · I tn i 21
CO
O a
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I x
β ω
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1-1 | X | β | r—| | I—1 | ||||||
X | a | °cd 1 H | Φ | Y | X | |||||
1—1 | l-1 | β | o | a | £ | 1-1 | 1—1 | β | ||
X | X | Φ | β | qj | 1 | (1) | X | X | φ | |
β | β | a | a | (1) | ω | P | β | β | a | |
Φ | Φ | 1 | o | P | 2 | [ | Φ | Φ | 1 | |
a | a | 2 | 1—1 | j | •H | fO | a | a | 2 | |
1 | 1 | O | 2 | ro | 2 | P | 1 | 1 | O | |
I-1 | β | III | X | P | 1 | o | i—1 | β | III | |
o | 2 | O | u | o | a | CO | o | 2 | o | |
1 | 1 | 1 | 1 | β | 1 | k | l | 1 | 1 | 1 |
M* | a | Mi | a | 2 | a | Ml | a | M* |
X β
ω a
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01-859-99 Če x
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X | 1—1 | P | Y | i—1 | |||||||
β | 1—1 | X | 1 | H | P | 1-1 | X | ||||
Φ | X | β | 2| | i—1 | Y | Φ | X | β | |||
1—1 | a | β | Φ | Y | ro | qj | i—1 | P | β | φ | |
X | 1 | Φ | a | qj | P | Φ | X | 1 | Φ | a | |
β | 1-1 | a | 1 | Φ | o | P | β | 1-1 | a | 1 | |
Φ | o | 1 | 2 | P | --- | I | ω | o | 1 | 2 | |
a | •H | 2 | -H | 1 | •H | ro | a | •H | 2 | -H | |
1 | 2 | O | 2 | ro | Ό | P | 1 | TJ | O | 2 | |
1-ί | 1 | III | 1 | P | 1 | o | ι—1 | 1 | III | 1 | |
o | M1 | u | a | o | Lf) | ω | O | P | o | a | |
1 | kk | 1 | k | 1 | »k | 1 | 1 | •o. | 1 | k | |
a | co | a | a h | 00 | co | 00 | a | co | a | a |
H
I-1 | ||
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1—1 | β | |
X β Φ | φ a 1 | 1-1 Y |
a | φ | β |
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CM | 1 | a |
2 | Mi | 1 |
2 | 1 | φ |
O | 1—1 | 2 |
ω 1 | o I | a | |
1 P | 1 a | 1 |
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1—1 | X | X | Φ | ||
lP X | Y P Φ | β Φ a | β Φ a | a 1 φ | 1-1 X β |
β | P | I | I | 2 | Φ |
Φ | I | CM | CM | 1 | a |
a | ro | 2 | 2 | M1 | 1 |
1 | P | 2 | 2 | 1 | φ |
φ | o | O | O | 1—1 | 2 |
2 I | o | | O I | a | | o I | a 1 |
1 | i p | 1 | Μ* | a | M1 |
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γ-1 | X | a | 1—1 | 1-1 | X | ||||||||
Y | β | -H | 1—, | X | X | β | |||||||
β | rj | Φ | 1—1 | a | Y | β | β | Φ | 1—1 | ||||
β | Φ | a | X | Φ | i—1 | β | Φ | Φ | a | X | |||
'(0 | P | 1 | β | 2 | X | Φ | a | a | 1 | β | |||
> | I | á | Φ | β | β | P | | | I | i—1 | Φ | |||
0 | 1 CN | O | a | CA | 2 | Φ | | | CM | CM | O | a | ||
>u | P | •H | 1 | O | a | ro | 2 | 2 | •H | 1 | |||
2 | φ | 'X | 1 | P | 2 | 2 | 2 | φ | |||||
β | o | 1 | 2 | β | β | II | φ | o | O | U | 1 | 2 | P |
λ; | ω | a | a | 2 | 2 | 2 | o | O | a | a | a | P | |
o | 1 | k | 1 | 1 | 'f0 | «-4 | 1 | 1 | 1 | 1 | k | 1 | 1 |
2 | co | a | a | a | >CN | 2 | a | 00 | a | a | a | a | 4J |
Žádný substituent • · υ
co *εΙ
Φ d ι—I β a φ Ε4
Ε
II η
Ε
£ | ||||||||||
β | ||||||||||
Φ | ||||||||||
a | ||||||||||
1—1 | 1 | 1—1 | ||||||||
£ | 1—1 | £ | ||||||||
β | ,—i | l-1 | £ | El | β | |||||
l-1 >1 | Φ a | >1 £ | l-1 | l-1 | £ β | P O | i—1 >1 | Φ a | ||
£ | 1 | Φ | £ | £ | Φ | β | 1 | |||
Φ | φ | d | | β | β | a | P | Φ | φ | ||
d I | £ | Φ | Φ | 1 | o | d i | £ | |||
•H | fd | a | a | E | i—1 | -H | ||||
fd | d | tm | 1 | 1 | O | a | fd | d | ||
tm | 1 | O | 1—1 | β | III | £ | tm | 1 | ||
O | LO | ω | o | m | u | u | O | a | ||
l | 1 | 1 | 1 | 1 | 1 | β | 1 | |||
a | a | a | a | a | m | a |
φ
i—| | a 1 | I—l >1 | £ β Φ | Γ—1 £ | 1—1 £ β | |
>1 | co | i—1 | a | β | Φ | |
£ | E | Φ | £ | 1 | Φ | a |
Φ | O | d | β | i—1 | a | 1 |
d | —' | j | Φ | o | 1 | E |
i | -H | (d | a | -H | E | H |
fd | d | tm | ι | d | O | d |
tm | 1 | O | ι—1 | 1 | III | 1 |
O | a | ω | O | a | o | a |
1 | 1 | 1 | 1 | |||
co | a | CO | a | a | a | a |
1—1 £ β Φ a I | |
i—I | 1 |
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1 fd | d |
tm | 1 |
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1 | «κ |
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£ β
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£ | β | β | a | |
β | Φ | Φ | 1 φ | |
Φ | a | a | β | |
a 1 | I | I | £ | Φ |
CJ | CN | 1 | a | |
rt | E | E | a | 1 |
E | E | E | 1 | φ |
O | U | O | 1—1 | £ |
O | | O | | ω I | o | | a 1 |
1 | 1 | 1 | a | 1 |
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β 1 | ι—I | β | ||||||||||
a | fd | 1-1 | £ | a | ||||||||
Φ | H | I-1 | £ | £ | β | Η | 1—1 | |||||
>o | a | >1 | β | ρ | Φ | ι—I | a | £ | ||||
w | ι—1 | £ | Φ | φ | a | £ | Μ | ί—1 | ρ | |||
σ | Λ | £ | φ | a | a | ι | β | d | £ | φ | ||
σ | β | β | d | 1 | 1 | Η | Φ | β | β | a | ||
I | ω | Φ | I | CN | CN | υ | a | Μ | ř-l | Φ | 1 | |
σ | a | 1 fd | Ε | Ε | •Η | ι | CQ | a | rt | |||
a | '£ | I | Ε | Ε | Ε | d | φ | '£ | ι | Ε | ||
00 | β | φ | U | U | Ο | ι | £ | β | β | II | φ | Ο |
ι | d | £ | Ο | Ο | a | a | a | Ε | d | £ | Ο | |
a | Φ | ι | 1 | 1 | ι | ι | ι | 'Φ | Η | ι | 1 | |
o | >Ν | a | a | a | a | a | a | a | >Ν | a | a |
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β φ
a ι
t—i a
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a | p | Φ | >1 | a | P | ||||||
i-1 | 1—1 | β | o | >1 | a | μ | l-1 | i-1 | β | o | |
a | a | φ | β | μ | 1 | Φ | a | a | φ | β | |
β | β | a | P | CL) | φ | q_l | β | β | a | P | |
φ | φ | 1 | o | 4M | £ | | | φ | φ | 1 | o | |
a | a | P | 1-[ | 1 | -H | m | a | a | P | l—1 | |
1 | 1 | o | p | rp | P | Pm | 1 | 1 | o | P | |
I-1 | β | lil | a | Pm | 1 | O | 1—1 | β | III | a | |
o | m | o | o | O | a | co | o | m | o | u | |
1 | 1 | 1 | 1 | β | 1 | 1 | 1 | 1 | 1 | 1 | |
xf | a | xf | a | PQ | xr | a | xr | xf | a | xf | a |
β m
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a | 1-1 | 4-1 | a | 1—1 | |||||||
β | 1—1 | a | i | β | 1—1 | a | |||||
φ | a | β | p| | |-1 | >1 | φ | a | β | |||
i—1 | a | β | φ | >1 | řp | μ | t—1 | a | β | φ | |
a | 1 | φ | a | μ | Pm | Φ | a | 1 | φ | a | |
β | 1—1 | a | 1 | Φ | O | 4-1 | β | 1—1 | a | 1 | |
φ | o | 1 | P | 4-1 | j | φ | o | 1 | P | ||
a | •H | P | •H | | | •H | <P | a | -H | P | •H | |
1 | P | o | P | (P | Ό | Pm | 1 | P | o | P | |
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β | a | Φ | a | a | φ | β | |||
φ | β | 4-1 | I | I | £ | Φ | |||
a | φ | | | CM | CM | 1 | a | |||
1 | a | rp | P | P | xf | 1 | |||
φ | 1 | Pm | P | P | 1 | φ | |||
£ | φ | O | o | o | 1—1 | £ | |||
a | tp | <P | £ | O | o | a | o | a | |
1 | P | P | 1 | 1 | 1 | 1 | 1 | 1 | |
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β | Φ | a | a | φ | ι—1 | μ | φ | Φ | a | a | φ | ||||
σ | 'Φ | 4-1 | ι | β | Ρ | a | Φ | a | a | 1 | β | P | |||
σ | > | | | ι—1 | φ | β | rp | β | 4-4 | | | I | l—1 | φ | β | ||
l | 0 | 04 | Ο | a | φ | 2 | φ | | | CM | CM | O | a | Φ | ||
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a | φ | 2 | Ρ | φ | 'a | ι | Ρμ | Ρ | Ρ | P | φ | <a | |||
a | β | Ο | 1 | £ | β | β | II | φ | Ο | υ | υ | 1 | £ | β | β |
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1 | 1 | 1 | 1 | τ | χ | X |
co | a | LO | Ρ | >Ν | a | a |
<—1 ο I | 2 | | 2 I | 2 | | Ρ ω 1 | φ 2 I | φ 2 J |
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β | |||||||||
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til | Ή | 1 | Η | Ή | Ή | •Η | •Η | ||
τ | a | τ | Τ | Ό | Ό | τ | |||
1 | X | I | 1 | I | I | ||||
φ | Ιί | LO | a | a | a | a | co | a | |
ι> | X | X | X | X | |||||
2 | a | χςρ | a | CM | η | Ρ | |||
φ ρ | |||||||||
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2 | 1—1 | β | |||||||
tl | 2 I | ο | m I | Η | ti | 2 I | |||
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2 | 2 | 2 | 2 | 2 | 2 | |
•a | •a | -a | -a | -a | -a | |
P | P | P | P | P | P | |
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2 | 2 | 2 | 2 | 2 | 2 | |
^a | 'a | -a | 'a | 'a | 'a | |
s | β | β | β | β | β | β |
υ | T | T | T | T | T | T |
ι | -Φ | τ | -Φ | -Φ | -Φ | -Φ |
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•ι—I
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• · · « • · · • · • · · · · · · • · · · * · · «· · · · ··· ··· • · · · · • ·· · · · ·· tál •ΓΊ
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ro P | ai | -H | 1 | •H | H | •H | •H | |
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o | 1 | 1 | 1 | 1 | 1 | |||
£ | kO | LO | kO | kO | kO | kO | ||
a | || | ·>. | ·* | *·. | ||||
co | CM | CM | co | |||||
rt | ||||||||
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1 | ro | 1 | 1 | |||
LO | υ | a | kO | LO | kO | |
r- | O | X | K. | |||
(0 | II | co | ||||
ulk | a | |||||
£ | II | |||||
rt | C4 I | |||||
E-i | ro | r-i | ||||
a | al | i—1 | ||||
a | a | a | o | |||
Cd | CM | CM | CM |
a | a | a | a | a | a | a | a | |||
-m | -m | -r~> | T~l | •ΓΊ | •m | -r~1 | •ΓΊ | |||
fe | fe | fe | fe | fe | fe | fe | fe | |||
—' | '— | —' | ro I | —1 | ||||||
ro | ro | ro | ro | ro | ro | al | ro | ro | ||
H | H | |||||||||
a | a | a | a | a | a | a | a | |||
'£ | '£ | 'I>1 | '>1 | sí>1 | '£ | '£ | ||||
a | β | β | β | β | β | β | a | β | β | |
u | £ | £ | £ | £ | £ | £ | o | £ | £ | |
1 | -Φ | £ | £ | £ | 'rt | 'Φ | 1 | '(tí | '(tí | |
CM | >Cd | >N | >N | >Cd | >N | >N | CM | >N | >N |
Μ I «Η al fe al
-Γ-1 fe
ω >ο σ
σ ι
σ a, a
LO 00 1 | '>1 -Š | Φ 2 | l—1 o | a | Φ g | β ra | Φ 2 co | '£ £ | Φ 2 | i—I O |
i—1 | 'rt | 1 | 1 | 1 | 1 | 1 | 1 | '(ti | 1 | 1 |
O | >Cd | CM | CM | CM | CM | CM | CM | >N | CM | Cd |
• · « ·« ···· ·· ♦ · ···« · * · · * ♦ •ΓΊ fc
CP «Η | tfc | ||
tá | o | ft | |
•d | •H | ||
x£>i | P | P | |
P | 1 | I | |
ft | TS | LO | LO |
1 | '(0 | ||
XP | >N | a | CM |
• · · ·· ·· · ··«··· ··· ··· ·· ·· «·· · · · ·* · · cn τ—i CM
CM I tál
2-F | 2-Et | 4-Me | 4-Me | u 00 (ti | |
Λ | |||||
CO | |||||
<. | |||||
fp 1 | ft | ft | ft | ft | ίΰ |
xl | •d | •d | •d | •d | 00 |
P | P | P | P | aP | |
LO | LO | LO | Lf) | a l—1 | |
CM | CM | a | £ Λ (ti | ||
a | |||||
o | |||||
£ | |||||
CM I H | ft | ||||
ftl | o | ||||
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X | H | ft | ft | £ | |
1 | 1 | 1 | 1 | 0 | |
a | a | N > | |||
'a | |||||
X | X | X | X | £ o | |
ω | |||||
• | • | • | • | P | |
•ΓΊ | •ΓΊ | •ΓΊ | •m | o | |
fp I Ή I | a | a | a | a | |
xl | fP | fp | fp | fP | |
«Η | 1-1 | ||||
X | X | X | X | ||
'a | a | 'a | 'a | ||
£ | £ | £ | £ | ||
P | P | P | P | ||
'f0 | 'Φ | '<0 | |||
>N | >N | >N | >íM |
CM
01-859-99 Če
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£ | CM | H { | ||||
'(ti | |||||
> | tál | ||||
0 | |||||
>0 | |||||
(ti | ω | cu | |||
£ | 2 | £ | 2 | ||
a | ft | O | X | ω | |
o | 1 | 1 | 1 | 1 | |
ft | a | a | a | a |
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Η ι—I £l « £
H 1—I £ U £ •rd -rd *a ό u
1-1 o 1 | £ 1 | £ 1 | £ 1 | £ P '(ti | 1 CD K | 1 a | i—1 o 1 | £ 1 | £ 1 |
a | a | a | sp | >N | a | a | a | a | a |
£l
i—1 o | £ | £ | £ | 4-) H | Φ £ | Φ £ | i—1 o | £ | £ |
CN | CN | a | CN | a | ’νΡ | ^P | a | CN | a |
Tabulka 8a
£ II | o i t—1 I £l | £ •H T 1 a | £ -rd β -P 1 a a | £ •H P 1 a | £ -H TJ 1 a | £ -rd Ti 1 a | £ •H τι 1 a | £ -rd Tl 1 a | Λ | rt £ U | ctí 1 i—1 £1 | £ Ή Tl 1 a | £ •H β d-1 1 a a | £ •H TJ 1 a |
’Τ | «Κ | v | CD | II | ||||||||||
^P | ra | 'xp | a | a | ra | ^P | ra | |||||||
<Ú | ||||||||||||||
£ | ||||||||||||||
o | ||||||||||||||
£ | 3 | ·» | ||||||||||||
O | Λ | £ | ||||||||||||
II | oj 1 i—1 | (ti £ | II | OJ I H | ||||||||||
£1 | £l | |||||||||||||
o | Ctí | |||||||||||||
£ | 1-1 | β | £ | 1-1 | ||||||||||
£ | £ | o | m | H | £ | £ | £ | £ | υ | |||||
CN | CN | a | ^P | ^P | a | a | a | CN | CN |
Ή | 34 | 34 | 34 | 34 | £ | £ | ||||
•m | •Γtí | •n | tí | •R | -m | -|—1 | ||||
-P | -P | -P | -P | -P | -P | Ctí I H | 4-1 | 4-) | ||
Ctí | Ctí | Ctí | Ctí | Ctí | Ctí | i | η | Ctí | ||
H | t—i | w | Ή | i—1 | 1—1 | H | Ή | |||
£ | £ | £ | £ | £ | £ | £ | £ | |||
'>1 | '>1 | '5ί | '5ί | '> | ||||||
£ | β | β | β | β | β | β | £ | β | β | |
O | Tl | TJ | TJ | Ti | TJ | Ti | O | Τ! | Tl | |
1 | '(ti | '(ti | '(ti | '(ti | '(ti | '(ti | 1 | '(ti | '(ti | |
a | >N | >M | >N | >N | >N | a | >N | >t>3 |
Φ >u σ
σ ι
σ a
co i
T-1 o
ffi
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04 | 04 | ||||||||
'>1 r* | Φ | 1—1 | Φ S | β | Φ £ | d | Φ | rH | |
Ό | s | o | £ | O | PQ | ra | Ό | s | υ |
1 | 1 | 1 | 1 | 1 | 1 | 'Cd | 1 | 1 | |
>N | a | a | a | a | a | a | >N | a | a |
• · # ♦ • · • ·
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Ε Η Ρ 1 | 1—1 | |||||||||
Ε | Ό | Ε | Ε | υ | Ε | Ε | Ε | Ρ | Ε | Ε |
1 | '05 | 1 | 1 | 1 | 1 | 'β | < | |||
>Ν | Ε | Ε | Ε | Ε | Ε | >Ν | Ε | Ε |
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μ | ||||||||||||||
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Ε | εΙ | •Η | ι | •Η | •Η | •Η | •Η | •Η | ||||||
Ρ | Ρ | Ρ | Ρ | Ρ | co | Ρ | Ρ | Ρ | Ρ | Ρ | ||||
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CO | CO | CO | Ε | ϋ | Ε | ιο | Ε | CO | CO | CO | CO | Ε | ||
κ. | κ. | 00 | Ο | χ | X. | •χ | «X | X. | *χ | |||||
Ε | Ε | Ε | Μ1 | Μ1 | Ε | Μ1 | Ε | Ε | Ε | Μ | ||||
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β | ||||||||||||||
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β | ι—1 | β | ||||||||||||
Ε | Η | Ε | Ε | Ε | Ε | υ | m | Η | t | t | ||||
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Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | ||
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Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | Ε | ||
'>1 | '>1 | '> | '>1 | '>1 | '>1 | ||||||
β | β | β | β | Ε | β | β | β | β | β | β | |
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'β | ρί | -β | £ | -β | £ ι—1 | Ρί | Ρί | Ρί | |
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> | X | a | a | X ·β | ι—1 | X | X 1 | 1 | |
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-CH2O-N=C (0CH3) - 3-Cl-fenyl -CH20-N=C (cyklopropyl) - 3-Cl-fenyl
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-SCF3-fenyl 4-SCF3-fenyl 3, 5-di (CF3)-fenyl
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Formulace/použitelnost
Sloučeniny podle vynálezu se budou zpravidla používat ve formě formulace nebo kompozice se zemědělsky vhodným nosičem obsahujícím alespoň jedno kapalné ředidlo, pevné ředidlo nebo povrchově aktivní činidlo. Složky formulace nebo kompozice se zvolí tak, aby byly v souladu s fyzikálními vlastnostmi účinné složky, způsobem aplikace a faktory životního prostředí, jakým je například typ půdy, vlhkost a teplota. Použitelné formulace zahrnují kapaliny, jako například roztoky (včetně emulgovatelných koncentrátů), suspenze, emulze (včetně mikroemulzí a/nebo suspoemulzí) apod., které lze případně zahustit do formy gelů. Použitelné formulace dále zahrnují pevné látky, například popraše, prášky, granule, pelety, tablety, fólie apod., které mohou být vodou dispergovatelné („smáčitelné) nebo vodou rozpustné. Účinná složka může být zapouzdřena v mikrokapslích a dále zpracována do suspenze nebo pevné formulace, alternativně může být celá formulace účinné složky zapouzdřena (nebo „potažena).
kontrolovat nebo zpozdit uvolnění
Rozprašovatelné formulace lze rozprašovat ve vhodném médiu a použít v rozprašovacích objemech přibližně jedno sto až několik set litrů na hektar. Velmi silné kompozice se použijí zejména jako meziprodukty pro další formulaci.
Zapouzdření může účinné složky.
Formulace budou zpravidla obsahovat účinná množství účinné složky, ředidla a povrchově aktivního činidla v následujících přibližných rozmezích a tato účinná množství budou dohromady tvořit 100 % hmotn.
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Procento hmotnosti
Účinná Ředidlo Povrchově složka aktivni činidlo
Vodou dispergovateiné a vodou rozpustné granule, tablety a prášky | 5-90 | 0-94 | 1-15 |
Suspenze, emulze, roztoky (včetně emulgovatelných koncentrátů) | 5-50 | 40-95 | 0-15 |
Popraše | 1-25 | 70-99 | 0-5 |
Granule a pelety | 0,01-99 | 5-99,99 | 0-15 |
Velmi silné kompozice | 90-99 | 0-10 | 0-2 |
Typická pevná ředidla popsal Watkins a kol. v Handbook of Insecticide Dust Diluents and Carriers, 2. vyd., Dorland Books, Caldwell, New Jersey. Typická kapalná ředidla popsal Marsden v Solvents Guide, 2. vyd., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey a rovněž Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, uvádí seznam povrchově aktivních činidel a jejich doporučená použití. Všechny formulace mohou obsahovat malá množství aditiv, která snižují pěnivost, spékavost, korozi, mikrobiologický růst apod., nebo zahušťovadel zvyšujících viskozitu formulací.
Povrchově aktivní činidla zahrnují například polyethoxylované alkoholy, polyethoxylované alkylfenoly, polyethoxylované estery sorbitanu a mastných kyselin, dialkylsulfosukcináty, alkylsulfáty, alkylbenzensulfonáty, organokřemičitany, Ν,Ν-dialkyltauráty, ligninsulfonáty, kondenzáty naftalensulfonátu a formaldehydu,
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62 polykarboxyláty a blokové kopolymery polyoxyethylenu a polyoxypropylenu. Pevná ředidla zahrnují například jíly, jakými jsou bentonit, montmorillonit, attapulgit a kaolin, škrob, cukr, silika, mastek, diatomová zemina, močovina, uhličitan vápenatý, uhličitan a hydrogenuhličitan sodný a síran sodný. Kapalná ředidla zahrnují například vodu, Ν,Ν-dimethylformamid, dimethylsulfoxid, jV-alkylpyrrolidon, ethylenglykol, polypropylenglykol, parafiny, alkylbenzeny, alkylnaftaleny, olivový olej, ricinový olej, olej z lněných semínek, tungový olej, sezamový olej, kukuřičný olej, podzemnicový olej, olej ze semen bavlníku, olej ze sojových bobů, řepkový olej a kokosový olej, estery mastných kyselin, ketony, například cyklohexanon, 2-heptanon, isoforon a 4-hydroxy-4-methyl-2-pentanon, a alkoholy, jako například methanol, cyklohexanol, dekanol a tetrahydrofurfurylalkohol.
Roztoky včetně emulgovatelných koncentrátů lze připravit prostým smísením jednotlivých složek. Popraše a prášky lze připravit smísením a zpravidla rozemletím v kladivovém mlýnu nebo mlýnu s tekutinovým pohonem. Suspenze se zpravidla připravují mletím za mokra; viz například patentový dokument US 3,060,084. Granule a pelety lze připravit rozprašováním účinné složky na předem vytvořené granulové nosiče nebo aglomeračními technikami. Viz Browning, „Agglomeration, Chemical Engineering,
4. prosinec 1997, str. 147 až 148, Perry's Chemical Engineer's Handbook, 4. vyd., McGraw-Hill, New York, 1963, str. 8 až 57 a následující; a WO 91/13546. Pelety lze připravit způsobem popsaným v patentu US 4,172,714. Vodou dispergovatelné a vodou rozpustné granule lze připravit způsobem, který popisuje patent US 4,144,050, US 3,920,442 « « « · • * * ·
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63 a DE 3,246,493. Tablety lze připravit způsoby popsanými v patentech US 5,180,587, US 5,232,701 a US 5,208,030. Fólie lze připravit způsoby popsanými v patentech GB 2,095,558 a US 3,299,566.
Další informace týkající se oblasti formulací lze nalézt například v patentu US 3,235,361, odst. 6, řádek 16 až odst. 7 řádek 19 a příklady 10 až 41; v patentu US 3,309, 192, odst. 5, řádek 43 až odst. 7/. řádek 62 a příklad 8, 12, 15, 39, 41, 52, 53, 58, 132, 138 až 140, 162 až 164, 166, 167 a 169 až 182; v patentu US 2,891,855, odst. 3 řádek 66 až odst. 5, řádek 17 a příklady 1 až 4; Klingman, Weed Control as a Science, John Wiley and Sons, lne., New York, 1961, str. 81 až 96; a Hance a kol., Weed Control Handbook, 8. vyd., Blackwell Scientific Publications, Oxford, 1989.
V následujících příkladech představují všechna procenta hmotnostní procenta (% hmotn.) a všechny formulace se připravily konvenčními způsoby. Čísla sloučenin označují sloučeniny v Indexových tabulkách A až C.
Příklad A
Smáčitelný prášek
Sloučenina 11 65,0 % Dodecylfenolpolyethylenglykolether 2,0 % Ligninsulfonát sodný 4,0 % Hlinitokřemičitan sodný 6,0 % Montmorillonit (žíhaný)
23,0 % • 0 000» ·· 0« « · · * » · · • « 0 ·’- *· • · * 0 » 0 · · « * » · · » · 00 > 0 * 00
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Příklad B
Granule
Sloučenina 13 | 10, 0 | ||
Attapulgitové | granule | (nízkotěkavá | látka, |
0,71/0,30 mm; | síta U.S.S. | No. 25 až 50) | 90, 0 |
Příklad C | |
Extrudovaná peleta | |
Sloučenina 14 | 25, 0 |
Bezvodý síran sodný | 10, 0 |
Surový lignosulfonát vápenatý | 5,0 |
Nátriumalkylnaftalensulfonát | 1,0 |
Bentonit vápenato/hořečnatý | 59, 0 |
Příklad D | |
Emulgovatelný koncentrát | |
Sloučenina 16 | 20, 0 |
Směs sulfonátů rozpustných v oleji a polyoxyethylenetherů | 10, 0 |
Isoforon | 70, 0 |
Sloučeniny podle vynálezu jsou použitelné jako činidla kontrolující choroby rostlin. Vynález tedy dále zahrnuje způsob kontroly rostlinných chorob způsobených fungálními rostlinnými patogeny, který zahrnuje aplikaci účinného množství sloučeniny podle vynálezu nebo fungicidní
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Puccinia fuliginea, kompozice obsahující tuto sloučeninu na rostlinu nebo její část, která se má chránit, nebo na semena rostliny nebo případně semenáče, které se mají chránit. Sloučeniny a kompozice podle vynálezu poskytují kontrolu chorob způsobených širokým spektrem fungálních rostlinných patogenů, které spadají do tříd basidiomycet, scomycet, oomycet a deuteromycet. Tyto kompozice jsou účinné při kontrole širokého spektra rostlinných chorob, zejména těch, které jsou způsobeny foliárními patogeny ha okrasných rostlinách, zelenině, polních plodinách, cereáliích a ovocných sklizních. Tyto patogeny zahrnují Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alternaria brassicae, Septoria nodorum, Septoria tritici, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis , Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Rhizoctonia solani, Sphaerotheca oxysporum, Verticillium dahliae,
Pythium aphanidermatum, Phytophthora megasperma,
Sclerotinia sclerotiorum, Sclerotium rolfsii, Erysiphe polygon!, Pyrenophora teres, Gaeumannomyces graminis, Rynchosporium secalis, Fusarium roseum, Bremia lactucae a další rody a druhy blízce příbuzné s těmito patogeny.
arachidis, Fusarium
Sloučeniny podle vynálezu rovněž vykazují účinnost proti širokému spektru arthropodů, kteří požírají listy, plody, stonky nebo kořeny a semena, a arthropodů, kteří žijí ve vodě a půdě (výraz „arthropodi zahrnuje hmyz,
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66 roztoče a hlísty), což jsou škůdci, kteří škodí na rostoucích a skladovaných zemědělských plodinách, lesním porostu, skleníkových rostlinách, okrasných rostlinách, školkových rostlinách, skladovaných potravinových a vláknitých produktech, skotu, v domácnostech a kteří poškozují zdraví u zvířat a lidí. Odborníci v daném oboru jsou si vědomi, že ne všechny sloučeniny jsou stejně účinné proti všem stadiím růstu všech škůdců. Nicméně všechny sloučeniny podle vynálezu jsou účinné proti ' následujícím stadiím růstu škůdců: vajíčkům, larvám a dospělým jedincům řádu Lepidoptera; vajíčkům, larvám požírajícím listy, plody, kořeny a semena a dospělým jedincům řádu Coleoptera; vajíčkům, nevyzrálým jedincům a dospělým jedincům řádu Hemiptera a Homoptera; vajíčkům, larvám, nymfám a dospělým jedincům řádu Acari; vajíčkům, nevyzrálým jedincům a dospělým jedincům řádu Thysanoptera, Orthoptera a Dermaptera; vajíčkům, nevyzrálým jedincům a dospělým jedincům řádu Diptera; a vajíčkům, nevyzrálým jedincům a dospělým jedincům Phylus nematoda. Sloučeniny podle vynálezu jsou rovněž účinné proti škůdcům řádu Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura a Psocoptera; škůdcům náležícím do třídy Arachnida a Phylum Platyhelminthes. Konkrétně jsou sloučeniny podle vynálezu účinné proti škůdcům, jakým je Diabrotica undecimpunctata howardi, Mascrosteles fascifrons, Anthonomus grandis, Tetranychus urticae, Spodoptera frugiperda, Aphis fabae, Myzus persica, Aphis gossypii, Diuraphis noxia, Sitobion avenae, Heliothis virescens, Lissorhoptrus oryzophilus, Oulema oryzae, Sogatella furcifera, Nephotettix cincticeps , Nilaparvata lugens, Laodelphax striatellus, Chilo suppressalis, Cnaphalocrocis medinalis, Scotinophara lurida, Oebalus pugnax, Leptocorisa chinensis, Cletus
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267 puntiger, Nezara viridula. Sloučeniny podle vynálezu jsou rovněž účinné při kontrole roztočů, přičemž zasahuji vajíčka a larvy a chemicky sterilizují dospělé jedince. V tomto případě jsou sloučeniny účinné zejména proti roztočům rodu Tetranichidae zahrnujícího Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi a Oligonychus pratensis; rodu Tenuipalpidae zahrnujícího Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus a Brevipalpus obovatus; rodu Eiophyidae zahrnujícího Phyllocoptruta olelvora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri a Eriophyes mangiferae. Podrobnější popis pesticidů lze nalézt v dokumentech WO 90/10623 a WO 92/00673.
Sloučeniny podle vynálezu lze rovněž směšovat s jedním nebo více dalšími insekticidy, fungicidy, nematocidy, baktericidy, akaricidy, regulátory růstu, chemosterilačními látkami, sémiotiky, repelenty, feromony, stimulátory krmení nebo dalšími biologicky účinnými sloučeninami za vzniku vícesložkového pesticidu, který poskytne dokonce širší spektrum zemědělské ochrany. Příklady takových zemědělských ochranných látek, se kterými lze formulovat sloučeniny podle vynálezu, zahrnují například: insekticidy, jakými jsou například abamectin, acephate, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, cyfluthrin, betacyfluthrin, cyhalothrin, lambda-cyhalothrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diflubenzuron
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268 esfenvalverate, fenoxycarb, fipronil, flucythrinate, imidacloprid, isofenphos, fenpropathrin, fenvalerate, tau-fluvalinate, fonophos, malathion, metaldehyd, methoprene, methamidophos, methidathion, methomyl, methoxychlor, methyl 7-chloro-2,5-dihydro[[N- (methoxykarbonyl)-N-[4-(trifluoromethoxy)fenyl]amino]karbonyl]indeno[1,2-e] [1,3,4]oxadiazin-4a(3Hj-karboxylát (DPX-JW062), monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon a triflumuron; fungicidy, jakými jsou například azoxystrobin, benomyl, blasticidin-S, Bordeaux směs (tribasický síran mědi), bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, cymoxanil, cyproconazole, diclomezine, dicloran, oxychlorid mědi, soli mědi, cyprodinil (CGA 219417), difenoconazole, dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole (BAS 480F), famoxadone, fenarimol, fenbuconazole, fenpropimorph, fluazinam, flutolanil, flutriafol, fenpiclonil, fenpropidin, fluquinconazole, flusilazole, folpet, fosetyl-aluminum, furalaxyl, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mepronil, metalaxyl, metconazole, 5-methyl 7benzothiazolkarbothioát (CGA 245704), myclobutanil, neoasozin (methanarsonát železitý), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propiconazole, pyrifenox, pyroquilon, quinoxyfen, spiroxamine (KWG4168), síra, tebuconazole, tetraconazole, thiabendazole, methylthiofanát, thiram, triadimefon, tricyclazole, triticonazole, validamycin triadimenol, vinclozolin;
t · · · · I
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69 nematocidy, jakými jsou například aldoxycarb a fenamiphos; baktericidy, jakým je například streptomycin; akaricidy, jakými jsou například amitraz, chinomethionát, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatinoxid, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben a tebufenpyrad; a biologická činidla, jakými jsou například Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, bakulovirus a entomopatogenní bakterie, viry a'houby.
V určitých případech budou pro zvládnutí rezistence výhodné zejména kombinace s dalšími fungicidy nebo arthropodicidy, které mají podobné spektrum působení ale jiný způsob působení.
Pro lepší kontrolu rostlinných chorob způsobených fungálními rostlinnými patogeny (např. nižší aplikační dávka nebo širší spektrum kontrolovaných rostlinných patogenů) nebo zvládnutí rezistence jsou výhodné směsi sloučeniny podle vynálezu s fungicidem zvoleným ze skupiny zahrnující azoxystrobin, benomyl, carbendazim, carpropamid, soli mědi, cymoxanil, cyproconazole, cyprodinil, dimethomorph, epoxiconazole, famoxadone, fenpropidin, fenpropimorph, flusilazole, flutolanil, fosetyl-aluminum, kasugamycin, kresoxim-methyl, mancozeb, metalaxyl a oxadixyl, pencycuron, probenazole, propiconazole, pyroquilon, tricyclazole, validamycin. Zvláště výhodné směsi (čísla sloučenin uvedených v Indexových tabulkách A až C) jsou zvoleny ze skupiny zahrnující: sloučenina Ί a azoxystrobin, sloučenina 7 a benomyl, sloučenina 7 a carbendazim, sloučenina 7 a carpropamid, sloučenina 7 a soli mědi, sloučenina 7 a cymoxanil, sloučenina 7 a cyproconazole, sloučenina 7 a cyprodinil, sloučenina 7 a
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epoxiconazole, sloučenina | 7 a famoxadone, | sloučenina | 7 a |
fenpropidin, sloučenina 7 | a fenpropimorph, | sloučenina | 7 a |
flusilazole, sloučenina 7 | a flutolanil, | sloučenina | 7 a |
fosetyl-aluminum, sloučenina 7 a kasugamycin, sloučenina 7 a kresoxim-methyl, sloučenina 7 a mancozeb, sloučenina 7 a metalaxyl, sloučenina 7 a oxadixyl, sloučenina 7 a pencycuron, sloučenina 7 a probenazole, sloučenina 7 a propiconazole, sloučenina 7 a pyroquilon, sloučenina 7 a tricyclazole, sloučenina 7 a validamycin, sloučenina 11 a azoxystrobin, sloučenina 11 a benomyl, sloučenina 11 a carbendazim, sloučenina 11 a carpropamid, sloučenina 11 a soli mědi, sloučenina 11 a cymoxanil, sloučenina 11 a cyproconazole, sloučenina 11 a cyprodinil, sloučenina 11 a epoxiconazole, sloučenina 11 a famoxadone, sloučenina 11 a fenpropidin, sloučenina 11 a fenpropimorph, sloučenina 11 a flusilazole, sloučenina 11 a flutolanil, sloučenina 11 a fosetyl-aluminum, sloučenina 11 a kasugamycin, sloučenina 11 a kresoxim-methyl, sloučenina 11 a mancozeb, sloučenina 11 a metalaxyl, sloučenina 11 a oxadixyl, sloučenina 11 a pencycuron, sloučenina 11 a probenazole, sloučenina 11 a propiconazole, sloučenina 11 a pyroquilon, sloučenina 11 a tricyclazole, sloučenina 11 a validamycin, sloučenina 13 a azoxystrobin, sloučenina 13 a benomyl, sloučenina 13 a carbendazim, sloučenina 13 a carpropamid, sloučenina 13 a soli mědi, sloučenina 13 a cymoxanil, sloučenina 13 a cyproconazole, sloučenina 13 a cyprodinil, sloučenina 13 a epoxiconazole, sloučenina 13 a famoxadone, sloučenina 13 a fenpropidin, sloučenina 13 a fenpropimorph, sloučenina 13 a flusilazole, sloučenina 13 a flutolanil, sloučenina 13 a fosetyl-aluminum, sloučenina 13 a kasugamycin, sloučenina 13 a kresoxim-methyl, sloučenina 13 a mancozeb, sloučenina 13 a metalaxyl, sloučenina 13 a oxadixyl, sloučenina 13 a
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271 ;
pencycuron, sloučenina 13 a probenazole, sloučenina 13 a propiconazole, sloučenina 13 a pyroquilon, sloučenina 13 a tricyclazole, sloučenina 13 a validamycin, sloučenina 14 a azoxystrobin, sloučenina 14 a benomyl, sloučenina 14 a carbendazim, sloučenina 14 a carpropamid, sloučenina 14 a soli mědi, sloučenina 14 a cymoxanil, sloučenina 14 a cyproconazole, sloučenina 14 a cyprodinil, sloučenina 14 a epoxiconazole, sloučenina 14 a famoxadone, sloučenina 14 a fenpropidin, sloučenina 14 a fenpropimorph, sloučenina 14 a flusilazole, sloučenina 14 a flutolanil, sloučenina 14 a fosetyl-aluminum, sloučenina 14 a kasugamycin, sloučenina 14 a kresoxim-methyl, sloučenina 14 a mancozeb, sloučenina 14 a metalaxyl, sloučenina 14 a oxadixyl, sloučenina 14 a pencycuron, sloučenina 14 a probenazole, sloučenina 14 a propiconazole, sloučenina 14 a pyroquilon, sloučenina 14 a tricyclazole, sloučenina 14 a validamycin, sloučenina 16 a azoxystrobin, sloučenina 16 a benomyl, sloučenina 16 a carbendazim, sloučenina 16 a carpropamid, sloučenina 16 a soli mědi, sloučenina 16 a cymoxanil, sloučenina 16 a cyproconazole, sloučenina 16 a cyprodinil, sloučenina 16 a epoxiconazole, sloučenina 16 a famoxadone, sloučenina 16 a fenpropidin, sloučenina 16 a fenpropimorph, sloučenina 16 a flusilazole, sloučenina 16 a flutolanil, sloučenina 16 a fosetyl-aluminum, sloučenina 16 a kasugamycin, sloučenina 16 a kresoxim-methyl, sloučenina 16 a mancozeb, sloučenina 16 a metalaxyl, sloučenina 16 a oxadixyl, sloučenina 16 a pencycuron, sloučenina 16 a probenazole, sloučenina 16 a propiconazole, sloučenina 16 a pyroquilon, sloučenina 16 a tricyclazole, sloučenina 16 a validamycin, sloučenina 40 a azoxystrobin, sloučenina 40 a benomyl, sloučenina 40 a carbendazim, sloučenina 40 a carpropamid, sloučenina 40 a soli mědi, sloučenina 40 a cymoxanil, sloučenina 40 a
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272 cyproconazole, sloučenina 40 a cyprodinil, sloučenina 40 a epoxiconazole, sloučenina 40 a famoxadone, sloučenina 40 a fenpropidin, sloučenina 40 a fenpropimorph, sloučenina 40 a flusilazole, sloučenina 40 a flutolanil, sloučenina 40 a fosetyl-aluminum, sloučenina 40 a kasugamycin, sloučenina 40 a kresoxim-methyl, sloučenina 40 a mancozeb, sloučenina 40 a metalaxyl, sloučenina 40 a oxadixyl, sloučenina 40 a pencycuron, sloučenina 40 a probenazole, sloučenina 40 a propiconazole, sloučenina 40 a pyroquilon, sloučenina 40 a tricyclazole, sloučenina 40 a validamycin, sloučenina 118 a azoxystrobin, sloučenina 118 a benomyl, sloučenina 118 a carbendazim, sloučenina 118 a carpropamid, sloučenina 118 a soli mědi, sloučenina 118 a cymoxanil, sloučenina 118 a cyproconazole, sloučenina 118 a cyprodinil, sloučenina 118 a epoxiconazole, sloučenina 118 a famoxadone, sloučenina 118 a fenpropidin, sloučenina 118 a fenpropimorph, sloučenina 118 a flusilazole, sloučenina 118 a flutolanil, sloučenina 118 a fosetyl-aluminum, sloučenina 118 a kasugamycin, sloučenina 118 a kresoxim-methyl, sloučenina 118 a mancozeb, sloučenina 118 a metalaxyl, sloučenina 118 a oxadixyl, sloučenina 118 a pencycuron, sloučenina 118 a probenazole, sloučenina 118 a propiconazole, sloučenina 118 a pyroquilon, sloučenina 118 a tricyclazole, sloučenina 118 a validamycin.
Podstatou kontroly rostlinných chorob je aplikace účinného množství sloučeniny podle vynálezu buď před infikací nebo po infikaci na část rostliny, která se má chránit, například na kořeny, stonek, listy, plody, semena, hlízy nebo poupata, nebo do média (půdy nebo písku) , ve kterém rostliny, které se mají chránit, rostou. Sloučeniny
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273 lze rovněž aplikovat na semena a chránit tak semena a semenáře.
V případě kontroly chorob může aplikační dávku těchto sloučenin ovlivnit celá řada faktorů životního prostředí a měla by se stanovit na základě znalosti konkrétních podmínek prostředí, do kterého se má aplikovat. Listy lze zpravidla chránit, pokud se ošetří dávkou nižší než 1 g účinné složky /ha až 5 000 g účinné složky /ha. Semena a semenáče lze za normálních podmínek chránit dávkou 0,1 g až 10 g účinné látky na 1 kg semen.
Arthropodní škůdci se kontrolují a zemědělské, zahradnické a speciální plodiny a rovněž lidské zdraví se chrání aplikací jedné nebo více sloučenin podle vynálezu v účinném množství do životního prostředí škůdců, jehož součástí jsou zemědělská a/nebo nezemědělská ohniska infekce, na plochy, které mají být chráněny, nebo přímo na škůdce, kteří se mají kontrolovat. Součástí vynálezu je tedy rovněž způsob kontroly škodlivých členovců a hlístů žijících na listech a v půdě a způsob ochrany zemědělských a nezemědělských sklizní, přičemž podstatou tohoto způsobu je aplikace jedné nebo více sloučenin podle vynálezu nebo kompozic obsahujících alespoň jednu takovou sloučeninu v účinném množství do životního prostředí škůdců, jehož součástí jsou zemědělská a/nebo nezemědělská ohniska infekce, na plochy, které mají být chráněny, nebo přímo na škůdce, kteří se mají kontrolovat. Výhodným způsobem aplikace je postřik. Alternativně lze granulové formulace těchto sloučenin aplikovat na listy rostlin nebo do půdy. Dalšími způsoby aplikace jsou například přímé a nebo reziduální postřiky, plošné postřiky, povlaky semen, mikrokapsle, systemická absorpce, vnadidla, ušní přívěsky,
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274 bolusy, rozprašovače, vykuřovadla, aerosoly, popraše, a mnoho dalších. Sloučeniny lze zabudovat do vnadidel, která členovci pozřou nebo do zařízení, jakými jsou například pasti apod.
Pokud se sloučeniny podle vynálezu použijí ke kontrole škodlivých členovců, potom mohou být použity v čistém stavu ale častěji se aplikují ve formě formulace obsahující jednu nebo více sloučenin s vhodnými nosiči, ředidly a povrchově aktivními látkami· a případně v kombinaci s potravou, což závisí na jejich konečném použití. Výhodným způsobem aplikace je například rozprašování vodní disperze nebo zušlechtěného olejového roztoku sloučenin. Kombinace s rozprašovacími oleji, rozprašovacími koncentráty, lepivými látkami, adjuvansy, dalšími rozpouštědly a synergicky působícími látkami, například s piperonylbutoxidem, často zvyšuje účinnost sloučeniny.
Aplikační dávka, potřebná pro účinnou kontrolu, bude záviset na takových faktorech, jakými jsou druh arthropodů, který má být kontrolován, životní cyklus škůdce, životní stadium, velikost škůdce, místo výskytu, roční doba, druh hostitelské rostliny nebo živočicha, stravovací návyky, způsob páření, okolní vlhkost, teplota apod. Za normálních podmínek je pro kontrolu škůdců v zemědělských ekosystémech dostatečná aplikační dávka přibližně 0,01 až 2 kg/ha účinné složky, ale dostatečná může být již dávka 0,001 kg/ha nebo naopak může být vyžadována dávka 8 kg/ha. Při nezemědělských aplikacích je za účinnou aplikační dávku považována dávka přibližně 1,0 až 50 mg/m2, ale dostatečná může být již dávka 0,1 mg/m2, nicméně v některých případech může být vyžadována dávka až 150 mg/m2.
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275 ;
Následující testy demonstrují kontrolní účinnost sloučenin podle vynálezu na konkrétních patogenech. Je však třeba zmínit, že kontrolní ochrana před patogeny, kterou poskytují tyto sloučeniny, se neomezuje pouze na tyto konkrétní druhy. Popis použitých sloučenin uvádí Indexové tabulky A až D, ve kterých byly použity následující zkratky: H = vodík, Cl = chlor, Br = brom. Zkratka „Př. označuje „Příklad a čísla v tomto sloupci označují číslo příkladu, ve kterém byla sloučenina připravena.
Indexová | tabulka A | |||||
\ /R4 | ||||||
O | ||||||
R3^ | ||||||
ch3o-_/n\^o | ||||||
N— | -N | |||||
\ | ||||||
ch3 | ||||||
Slouč. č. | Př | βΐ | Y | z | tt. f°C) | |
1 | ch3 | H | CH2O-N=C(CH3) | 3,5-diCl-Ph | » | |
? | ch3 | H | CH2O-N=C(CH3) | 3,5-diBr-Ph | 163-164 | |
3 | ch3 | H | CH2O-N=C(CH3) | 3-OCF3-Ph | olej* | |
4 | ch3 | H | CH2O-N=C(CH3) | 3,4-diCI-Ph | 109-110 | |
5 | ch3 | ch3 | CH2O-N=C(CH3) | 3,5-diCl-Ph | » | |
6 | ch3 | H | CH2O-N=C(CH3) | 4-CH3-Ph | olej* | |
7 | 1 | ch3 | H | 0 | 3-CF3-Ph | 95-96 |
8 | ch3 | H | 0 | 4-Cl-Ph | 87-89 | |
9 | H | ch3 | CH2O-N=C(CH3) | 3-CH3-Ph | 119-122 | |
10 | H | ch3 | CH2O-N=C(CH3) | 3,5-díCl-Ph | 159-161 | |
11 | 4 | ch3 | H | 0 | Ph | 58-60 |
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Slouč. č | Př | Rý | EÍ | Y | z | t.t. f°C) |
12 | ch3 | H | 0 | 4-F-Ph | 99-101 | |
13 | ch3 | H | O | 3-CH3-Ph | 70-72 | |
14 | ch3 | H | 0 | 4-CH3-Ph | 72-74 | |
15 | ch3 | H | 0 | 3,5-diCl-Ph | 161-163 | |
16 | ch3 | H | 0 | 3-F-Ph | 108-110 | |
17 | 2 | ch3 | H | 0 | 4-OCF3-Ph | 75-77 |
18 | 3 | ch3 | H | och2 | 3-CH3-Ph | * |
19 | ch3 | H | och2 | 3-CF3-Ph | * | |
20 | ch3 | H | och2 | 4-/-Bu-Ph | * | |
21 | ch3 | H | och2 | 2-CH3-Ph | 158-160 | |
22 | ch3 | H | 0 | 4-OCH3-Ph | » | |
23 | ch3 | H | 0 | 3-Cl-Ph | 105-107 | |
24 | ch3 | H | 0 | 3,5-diCH3-Ph | 96-99 | |
25 | ch3 | H | 0 | 4-Br-Ph | 119-121 | |
26 | ch3 | H | 0 | 3-Br-Ph | 90-95 | |
27 | ch3 | H | 0 | 3-C1-4-F-PH | 106-108 | |
28 | ch3 | H | 0 | 3,4-diCl-Ph | 90-92 | |
29 | ch3 | H | 0 | 2-CH3-Ph | ||
30 | ch3 | H | o | 3-OCF3-Ph | 50-52 | |
31 | H | ch3 | 0 | 3-CF3-Ph | 113-115 | |
32 | H | ch3 | 0 | Ph | 123-124 | |
33 | ch3 | H | 0 | 2-naftalenyl | 120-122 | |
34 | ch3 | H | CH2O-N=C(CH3) | 3-CH3-Ph | 64-67 | |
35 | ch3 | H | ch2 | Br | 115-116 | |
36 | ch3 | H | ch2o | 3-CF3-Ph | 120-123 | |
37 | ch3 | H | ch2o | 2-CH2CH3-Ph | lepkavá pevná látka* | |
38 | ch3 | H | ch2o | 2-CH(CH3)2-Ph | olej* | |
39 | ch3 | H | ch2o | 2-C(CH3)3-Ph | 137-139 | |
40 | ch3 | H | CH2O-N=C(CH3) | 4-CF3-2-pyridinyl | olej* | |
41 | ch3 | H | 0 | 3-(OCH)-l ,2,4-thiadiazoi-5-yl | * | |
42 | ch3 | H | 0 | 5-CI-6-CH2CH3-4-pyrimidinyl | 99-103 | |
43 | ch3 | H | 0 | 3-1-1,2,4-thiad iazol-5-yl | 133-136 | |
44 | ch3 | H | 0 | 6-C(CH3)3-4-pyrimidinyl | olej* | |
45 | ch3 | H | 0 | 4-CF3-5-Br-2-thiazolyl | 144-146 | |
46 | ch3 | H | 0 | 4-CF3-2-thiazolyI | 141-143 | |
47 | ch3 | H | 0 | 4-CF3-5-CH3-2-thiazolyl | 118-121 |
» · » · · ·
277
β! | r! | γ | Z | t.t. (°C) |
ch3 | H | CH2O-N=C(CH3) | 4-CH3-2-pyridinyI | 97-98 |
ch3 | H | 0 | 2,3,5,6-tetra-F-4-pyridinyl | 103-105 |
ch3 | H | 0 | 4-CF3-5-CH2CH3-2-thiazolyl | 116-118 |
ch3 | H | o | 2-OCH(CH3)CF3-4-pyrimidinyl | 148-150 |
ch3 | H | 0 | 4-OCH(CH3)CF3-2-pyrimidinyl | 141-146 |
ch3 | H | CH2O-N=C(CH3) | 5-CF3-2-pyridinyl | 77-78 |
ch3 | H | ch2o | 1-naftalenyl | 112-115 |
ch3 | H | 0 | 5-CF3-2-pyridinyl | 138-139 |
ch3 | H . | 0 | 4-Br-2-thiazolyl | 205-208 |
ch3 | H | 0 | 5-Br-2-thiazolyl | 88-90 · |
ch3 | H | ch2o | 2-Cl-3-pyridinyl | 142-145 |
ch3 | H | CH2O-N=C(CH3) | 4-CF3-6-CH3-2-pyridinyI | 115-116 |
ch3 | H | 0 | 2-thiazolyl | 112-113 |
ch3 | H | CH2O-N=C(CH3) | 4-z-Bu-2-pyridinyl | * |
ch3 | H | CH?O-N=C(CH3) | 4-CHF2-2-pyridinyl | 105-108 |
ch3 | H | 0 | 2-CI-4-pyrimidinyl | 103-108 |
ch3 | H | ch2o | 2-CH3-5-CH(CH3)2-Ph | 93-94 |
ch3 | H | CH2° | 2,3,6-triMe-Ph | 113-115 |
ch3 | H | ch2o | 2,4,6-triMe-Ph | 92-94 |
ch3 | H | ch2o | 2,3,5-triMe-Ph | 140-142 |
ch3 | H | ch2o | 2-F-Ph | 82-85 |
ch3 | H | ch2o | 3-F-Ph | 96-97 |
ch3 | H | ch2o | 4-F-Ph | 116-118 |
ch3 | H | 0 | 4-CF3-2-p'yrimidinyl | 102-106 |
ch3 | H | o | 3-I-Ph | 127-129 |
ch3 | H | 0 | 6-OCH3-2-naftalenyl | * |
ch3 | H | 0 | 3-CN-Ph | 138-140 |
ch3 | H | 0 | 3-(OCH)-Ph | 91-93 |
ch3 | H | 0 | 2-ř-Bu-4-pyrimidinyl | 134-136 |
ch3 | H | 0 | 5-Cl-2-thiazolyl | 191-196 |
ch3 | H | 0 | 5-CF3-l,3,4-thiadiazol-2-yl | 125-127 |
ch3 | H | přímá vazba | ch2ci | 114-117 |
ch3 | H | 0 | 5-I-2-thiazolyl | 133-136 |
ch3 | H | CH2O-N=C(CH3) | 2-F-5-CH3-Ph | olej* |
ch3 | H | CH2O-N=C(CH3) | 2-F-5-CF3-Ph | * |
ch3 | H | CH20 | 2-Br-4-F-Ph | 144-147 |
«· « »« ·«·· 1 * · · · · · | • « · * • · · · | ||||
01-859- | 99 Če | 278 | « · · « · < • fc · ♦ * · · • · · ř · · «· · · · ·· · | * · * · • · « 4 · · * • · NA · · | |
Slouč. ά | Př r2 | rí | Y | z | t.t. ra |
85 | ch3 | H | ch2o | 2-F-4-Br-Ph | 19M93 |
86 | ch3 | H | ch2o | 3,4-di-F-Ph | 115-H7 |
87 | ch3 | H | 0 | 5-CH3-2-thiazolyl | 107-109 |
88 | ch3 | H | 0 | 5-Si(CH3)3-2-thiazoIyI | 66-68 |
89 | ch3 | H | 0 | 4-CF3-2-pyridinyl | olej* |
90 | ch3 | H | CH2O-N=C(CH3) | 4 -CF3 -6-Cl-2-pyridinyl | 120-123 |
91 | ch3 | H | ch2o | 2,3-di-F-Ph | 107-109 |
92 | ch3 | H | ch2o | 2,5-di-F-Ph | 124-126 |
93 | ch3 | H- | ch2o | 2,3,5-tri-F-Ph | 124-126 |
94 | ch3 | H | ch2o | 2,4,5-tri-F-Ph | Í69-170.5 |
95 | ch3 | H | ch2o | 2,3,5,6-tetra-F-Ph | H9-121 |
96 | ch3 | H | ch2s | 2,5-di-CH3-Ph | 94-96 |
97 | ch3 | H | 0 | 4-CH3-5-Br-2-thiazolyl | 157-158 |
98 | ck3 | H | ch2o | 2-F-5-CH3-Ph | 122-125 |
99 | ch3 | H | 0 | 4-CH3-5-l-2-íhiazolyl | 170-172 |
100 | ch3 | H | 0 | 3-(CH3CsC)-Ph | * |
101 | ch3 | H | 0 | 3-(í-Bu-CsC)-Ph | 141-143 |
102 | ch3 | H | och2 | 3-pyridinyl | 147-15I |
103 | ch3 | H | och2 | 4-pyridinyI | 127-131 |
104 | ch3 | H | 0 | 5-(CH3S)-2-thiazolyl | 60-64 |
105 | ch3 | H | 0 | 4-CH3-5-CI-2-thiazoIyl | 132-134 |
106 | ch3 | H | 0 | 5-n-Bu-2-thiazolyl | ÍOO-IOI |
107 | H | ch3 | CH2O-N=C(CH3) | 4-CF3-2-pyridinyl | olej* |
108 | ch3 | H | 0 | 6-/-BuO-4-pyrÍmidinyl | olej* |
109 | ch3 | H | CH2O-N=C(CH3) | 3-Si(CH3)3-Ph | * |
110 | ch3 | H | 0 | 3-(>-C^C>Ph | » |
111 | ch3 | H | 0 | 3-(HC=C)-Ph | 91-93 |
112 | ch3 | H | 0 | 3-((CH3)3SiOC)-Ph | * |
113 | ch3 | H | och2- | □ r ch3 | 172-174 |
114 | ch3 | H | CH2O-N=C(CH3) | 6-CF3-2-pyridinyl | 105-108 |
» Φ · · · ·
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Slouč. č. | Př | RČ | Y | z | t.t. (°Q | |
115 | ch3 | H | OCH2-( | CE 1 Or“3 | 175-178 | |
116 | ch3 | H | 0 | 5-( HOcH-C=C)-2-thiazolyl h2c | ||
117 | ch3 | H | 0 | 5-((CH3)3C)-Ph | * | |
118 | 5 | ch3 | H | o | 2-thienyl | olej* |
119 | ch3 | H | CH2O-N=C(CH3) | 3-CF3-Ph | 62-65 | |
120 | ch3 | H | 0 | 4,5-di-Br-2-thiazolyl | 174-176 | |
121 | ch3 | H | o | 5-(CH3CH2CH2)-2-thiazolyl | 100-101 | |
122 | 6 | ch3 | H | o | 5-Br-2-thienyl | olej* |
123 | C«3 | H | CH2O-N=C(CH3) | 3-CF3-2-pyridinyl | 111-112 | |
Viz | Indexová | tabulka D data 1H | NMR. |
Indexová tabulka B
Slouč. č.
86-88
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Indexová tabulka C ·· «··· > · e »· »··
280
Slouč. č.
124
125
X ch3s
CH3S(O)
t.t.(°C)
109-111
108-111
Indexová tabulka D
Slouč. č.
Data1H NMR (roztok CDC13, není-li stanoveno jinak)a
1 | δ | 7,49 (d,2H), 7,37-7,26 (m, 4Η) , 5,15 (ABq,2H), 3,89 (s,3H), 3,43 (s,3H), 2,18(s,3H), 2,15 (s,3H). |
3 | δ | 7,50 (m,2H), 7,34 (m,4H), 7,20 (m, IH), 5,18 (dd,2H), 3,87 (s,3H), 3,40 (s,3H), 2,18 (s, 6H) . |
5 | δ | 7,48 (d,2H), 7,32 (d,lH), 7,21 (d,2H), 5,16 (d,2H), 3,86 (s,3H), 3,46 (d,3H), 2,47 (d,3H), 2,10 (d,6H). |
6 | δ | 7,48 (d,lH), 7,46 (s,lH), 7,41 (dd,2H), 7,35 (d,lH), 7,16 (d,2H), 5,15 (ABq,2H), 3,46 (s,3H), 2,34 (s,3H), 2,18 (s,6H),l,95 (s,3H). |
18 | δ | 7,24 (m,2H), 7,1 (m,3H), 6,85 (m,2H), 5,03 (s,2H), 3,88 (s,3H), 3,45 (s,3H), 2,35 (s,3H), 2,22 (s,3H). |
• · · · » * · » · ·
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19 | δ 7,51 (m,4H), 7,37 (m,lH), 6,94 (d,lH), 6,83 | |||
(d,lH), 5,11 2,24 (s,3H). | (s,2H), 3,88 | (s,3H), 3,44 | (s,3H), | |
20 | δ 7,36 (m,2H), (s,2H), 3,88 1,31 (s,9H). | 7,25 (m,3H), (s,3H), 3,45 | 6,87 (m,2H), (s,3H), 2,23 | 5, 05 (s,3H), |
22 | δ 7,23 (m,IH), (d,lH), 3,90 2,26 (s,3H). | 6,95 (m,3H), (s,3H), 3,79 | 6,84 (m,2H), (s,3H), 3,42 | 6, 67 (s,3H), |
29 | δ 7,22- (m,3H) , (d,lH), 6,55 2,27 (s,3H), | 7,07 (t,lH), (d,lH), 3,89 2,18 (s,3H). | 7,00 (d,lH), (s,3H), 3,42 | 6, 92 (s,3H), |
37 | δ 7,46 (d, J=7 7,28 (d, J=7 J=7 Hz, IH), (s,2H), 3,90 J=7,5 Hz, 2H) 3H) . | Hz, IH), 7,38 Hz, IH), 7,12 6,78 (d, J=8 (s,3H), 3,44 , 2,18 (s,3H) | 1 (t, J=7 Hz, (m,2H), 6,89 Hz, IH), 4,98 (s,3H), 2,66 , 1,20 (t, J= | IH) , (t, (qz 7,5 Hz, |
38 | δ 7,47 (d, J=7, | .5 Hz, IH), 7, | 39 (t, J=7,5 | Hz, |
IH), 7,29 (d, J=7,5 Hz, IH), 7,22 (dd, J=7,5, 1,7 Hz, IH), 7,10 (td, J=7,5, 1,7 Hz, IH) , 6,93 (t, J=7,5 Hz, IH), 6,79 (d, J=7,5 Hz, IH), 4,97 (s,2H), 3,90 (s,3H), 3,45 (s,3H), 3,36 (m,lH), 2,18 (s,3H), 1,22 (d, J=7 Hz,
6H) .
δ 8,74 (d, J=5 Hz, IH), 8,10 (s,lH), 7,45-7,30 (m,4H), 5,23 (ABq,2H), 3,89 (s,3H), 3,43 (S,3H), 2,31 (s,3H), 2,18 (s,3H).
δ 7,44 (t,IH), (s,3H), 3,07
7,34 (m,2H), (S,1H), 2,29
3,83 (s,3H), (s,3H) .
3, 40 δ 8,71 (d,lH,J=l,0), 7,41 (t,IH,J=7,7), 7,14 (d,lH,J=8,0), 6,87 (d,IH,J=l,0), 3,75 (2,3H), 3,33 (s,3H), 2,27 (s,3H), 1,34 (s,9H).
δ 8,48 (d, J=5 Hz, IH), 7,83 (s,lH), 7,39 (m,2H), 7,26 (m,2H), 5,21 (m,2H), 3,89 (s,3H), 3,42 (s,3H), 2,30 (s,3H), 2,18 (s,3H), 1,33 (s,9H).
• · · · · ·
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282 pokračováni δ 7,69 (d,lH), 7,61 (d,lH), 7,31 (s,lH), 7,17 (m,4H), 7,04 (d,lH), 6,79 (d,lH), 3,91 (s,3H),
3,83 (s,3H), 3,36 (s,3H), 2,28 (s,3H).
δ 7,40-7,37 (m,2H), 7,35-7,20 (m,2H), 7,15-7,05 (m,lH), 6,95 (dd,lH), 5,15 (ABq,2H), 3,89 (s,3H), 3,43 (s,3H), 2,31 (s,3H), 2,20 (s,3H), 2,19 (s,3H).
δ 7,85 (d,lH), 7,63-7,58 (m,lH), 7,38 (d,lH),
7,32-7,29 (m,2H), 7,18 (t,lH), 5,17 (ABq,2H), 3,89 (s,3H), 3,42 (s,3H), 2,22 (d,'3H), 2,18 (s,3H).
δ 8,31 (d,IH,J=5,0), 7,4 (m,lH), 7,2 (m,2H),
7,1 (m,2H), 3,8 (s,3H), 3,3 (s,3H), 2,26 (s,3H).
100 | δ | 7,27 (in, 1Η) , (S,1H), 6,92 3,39 (s,3H), | 7,21 (m,IH), (d,lH), 6,80 2,27 (s,3H), | 7,10 (m,2H), (d,lH), 3,84 2,02 (s,3H). | 7,00 (s,3H), |
107 | δ | 8,73 (d, 1H,J= | =4,0), 8,10 ( | S,1H), 7,43 | |
(d,IH,J=3,8), | 7,35 (m,2H) | , 7,08 (m,lH), | 5,26 | ||
(s,2H), 3,86 | (s,3H), 3,43 | (s,3H), 2,54 | (s,3H), | ||
2,25 (s,3H). | |||||
108 | δ | 8,35 (s,lH), | 7,4 (m,IH), | 7,2 (m,lH), 7, | 1 |
(m,IH), 6,05 | (S,1H), 3,79 | (s,3H), 3,34 | (s,3H) , | ||
2,25 (s,3H), | 1, 60(s,9H) . | ||||
109 | δ | 7,72 (s,lH), | 7,56 (d,lH), | 7,50 (d,lH), | 7,25- |
7,40 (m,4H), | 5,16 (Abq,2H), 3,88 (s,3H) | , 3,41 | |||
(s,3H), 2,21 | (s,3H), 2,18 | (s,3H), 0,28 | (s, 9H) . | ||
109 | δ | 7,26 (m,lH), | 7,19 (t,lH), | 7,10 (d,lH), | 7,06 |
(d,lH), 6,99 | (s,lH), 6,89 | (m,lH), 6,79 | (d, IH), | ||
3,84 (s,3H), | 3,39 (s,3H), | 2,26 (s,3H), | 1,41 | ||
(m,IH), 0,85 | (m,2H), 0,78 | (m,2H). | |||
112 | δ | 7,23 (m,3H), | 7,08 (m,2H), | 6,96 (m,lH), | 6, 79 |
(d,lH), 3,84 | (s,3H), 3,39 | (s,3H), 2,27 | (s,3H), | ||
0,23 (s,9H). | |||||
116 | δ | 7,38 (m,lH), | 7,21 (m,3H), | 3,82 (s,3H), | 3, 41 |
(s,3H), 2,27 (s,3H), 1,42 (m,lH), 0,89 (m,2H), 0,79 (m,2H) .
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7,22 (m,2H), 7,17 (s,lH), (s,3H), 2,28 (s,3H), 1,28
3,83 (s, 9H) .
283 pokračování
117 δ 7,38 (t,lH), (s,3H), 3,41
118
122
δ | 7,26 (t,lH), | 7,05 (d,lH), | 6, 91 | (d,lH), | 6, 77- |
6,83 (m,2H), | 6,55 (dd,1H), | 3, 93 | (s,3H), | 3, 45 | |
(s,3H), 2,27 | (s,3H). | ||||
δ | 7,28 (t,lH), | 7,07 (d,lH), | 6, 95 | (d,lH) , | 6, 79 |
(d,lH), 6,35 | (d,lH), 3,94 | (s,3h: | ), 3,45 | (s,3H), | |
2,26 (s,3H). |
a Data 1H NMR jsou vyjádřena v ppm směrem dolů od tetramethylsilanu. Zkratky mají následující významy: s = singlet, d = dublet, m = multiplet, t = triplet, ABq = AB kvartet, dd = dublet dubletů a td = triplet dubletu.
Biologické příklady vynálezu
Testované sloučeniny se nejprve rozpustily v acetonu, v množství odpovídajícím 3 % konečného objemu, a následně se suspendovaly v koncentraci 200 ppm v čištěné vodě obsahující 250 ppm povrchově aktivního činidla Trém 014 (estery vícesytných alkoholů). Výsledné testované suspenze se následně použily v testech A až F. Nástřik 200 ppm těchto testovaných suspenzí, který se aplikoval dokud nedošlo ke stékání suspenze po testovaných rostlinách, odpovídá aplikační dávce 500 g/ha.
Test A
Testovaná suspenze se aplikovala na semenáče pšenice tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče
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4 naočkovaly výtrusy spor Erysiphe graminis f. sp. tritici (běžná příčina padlí pšenice) a inkubovaly v růstové komoře 7 dnů při 20°C, načež se provedlo zhodnocení choroby.
Test B
Testovaná suspenze se aplikovala na semenáče pšenice tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče naočkovaly výtrusy spor Puccinia recondita (běžná příčina rzi listové u pšenice) a 24 hodin inkubovaly v nasycené atmosféře při 20°C, načež se přemístily do růstové komory, kde se ponechaly 6 dnů při 20°C. Po jejich uplynutí se provedlo zhodnocení choroby.
Test C
Testovaná suspenze se aplikovala na semenáče rýže tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče naočkovaly výtrusy spor Pyricularia oryzae (běžná příčina předčasného vypadávání zrn z rýže) a 24 hodin inkubovaly v nasycené atmosféře při 27°C, načež se přemístily do růstové komory, kde se ponechaly 5 dnů při 30°C. Po jejich uplynutí se provedlo zhodnocení choroby.
Test D
Testovaná suspenze se aplikovala na semenáče rajčat tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče naočkovaly výtrusy spor Phytophthora infestans (běžná
01-859-99 Če
• ·
285 příčina plísně brambor a rajčat) a 24 hodin inkubovaly v nasycené atmosféře při 20 °C, načež se přemístily do růstové komory, kde se ponechaly 5 dnů při 20°C. Po jejich uplynutí se provedlo zhodnocení choroby.
Test E
Testovaná suspenze se aplikovala na semenáče vinné révy tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče naočkovaly výtrusy spor Plasmopara viticola (běžná příčina padlí vinné révy) a 24 hodin inkubovaly v nasycené atmosféře při 20°C, načež se přemístily do růstové komory, kde se ponechaly 6 dnů při 20°C a potom se opět 24 hodin inkubovaly v nasycené atmosféře při 20°C. Po jejich uplynutí se provedlo zhodnocení choroby.
Test F
Testovaná suspenze se aplikovala na semenáče okurek tak dlouho, dokud nedošlo ke stékání suspenze po testovaných rostlinách. Následující den se semenáče naočkovaly výtrusy spor Botrytis cinerea (běžná příčina botritidy u mnoha plodin) a 48 hodin inkubovaly v nasycené atmosféře při 20°C, načež se přemístily do růstové komory, kde se ponechaly 5 dnů při 20°C. Po jejich uplynutí se provedlo zhodnocení choroby.
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286
Výsledky testů A až F jsou uvedeny v Tabulce A. Hodnocení 100 v této tabulce označuje 100% kontrolu choroby a hodnocení 0 označuje, že nedošlo k žádné kontrole choroby (vzhledem ke kontrolním vzorkům) . Pomlčky (—) označují, že nebyly získány žádné výsledky a zkratka ND označuje případy, kdy nebylo možno kontrolu choroby stanovit v důsledku fytotoxity.
Tabulka A
Slouč.
ά | Test A | TestB | Test C | Test D | Test E | Test F |
1 | 99 | 100 | 97 | ND | 100* | ND |
2 | 100 | 100 | 98 | 85 | 100* | 77 |
3 | 99 | 100 | 100 | 100 | 100* | 96 |
4 | 77 | 99 | 90 | 100 | 100* | 0 |
5 | 99 | 100 | 99 | 0 | 100* | 0 |
6 | 99 | 100 | 91 | 99 | 100* | 0 |
7 | 100 | 100 | 99 | 76 | 100* | 0 |
8 | 100 | 100 | 100 | 100 | 99* | 0 |
9 | 100 | 100 | 99 | - | 100* | 0 |
10 | 99 | 100 | 86 | ND | 100* | 0 |
11 | 100 | 100 | 97 | 99 | 94* | 94 |
12 | 100 | 100 | 99 | 100 | 99* | 0 |
13 | 100 | 100 | 94 | ND | 54* | 0 |
14 | 100 | 100 | 97 | 90 | 77* | 0 |
15 | 100 | 100 | 94 | 96 | 9* | 0 |
16 | 100 | 100 | 99 | 100 | 86* | 0 |
17 | 100 | 100 | 97 | ND | 49* | 0 |
18 | 99 | 94 | 97 | 81 | 16* | 0 |
19 | 98 | 94 | 0 | 51 | 55* | 0 |
20 | 91 | 94 | 53 | 18 | 47* | 94 |
• · · ·
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287
Slouč,
c. | Test A | Test B | Test C | TestD | TestE | Tes |
21 | 99 | 97 | 97 | 76 | 0* | 0 |
22 | 99 | 100 | 99 | 94 | 33* | 43 |
23 | 99 | 100 | 100 | ND | 87* | 0 |
24 | 98 | 99 | 97 | 72 | 13* | 94 |
25 | 100* | 96* | 32** | - | 100* | - |
26 | 100 | 100 | 97 | 99 | 100* | 95 |
27 | 100 | 100 | 97 | 96 | 87* | 82 |
28 | 99 | 97 | 94 | 0 | 100* ' | 83 |
29 | 98 | . 99 | 0 | 0 | - | 0 |
30 | 97 | 100 | 100 | ND | - | 94 |
31 | 98 | 86 | 0 | 19 | 0* | 0 |
32 | 95 | 86 | 0 | 0 | 8* | 0 |
34 | 98 | 99 | 91 | 0 | 100* | 0 |
35 | 56 | 0 | 0 | 24 | - | 0 |
36 | 100 | 100 | 97 | ND | 100* | 0 |
37 | 99 | 99 | 86 . | 0 | - | 0 |
38 | 100 | 100 | 97 | 0 | 28* | 0 |
39 | 98 | 94 | 53 | 16 | 7’ | 0 |
40 | 100 | 100 | 93 | 73** | 100* | 0 |
41 | 11* | 52* | 0* . | - | 13* | - |
42 | 98 | 93 | 86 | 74 | 12* | 97 |
43 | 86 | 93 | 86 | 74 | - | 0 |
44 | 98 | 99 | 94 | 86 | 41* | 73 |
45 | 100 | 99 | 53 | 92 | 100* | 0 |
46 | 99 | 100 | 74 | 61 | 99* | 0 |
47 | 100 | 100 | 99 | 86 | 100* | 0 |
48 | 95 | 100 | 74 | 0 | 78* | 0 |
49 | 91 | 28 | 0 | 0 | 6* | 86 |
50 | 99 | 100 | 97 | ND | 25* | 0 |
51 | 100 | 100 | 97 | 92 | 16* | 0 |
52 | 100 | 100 | 97 | 96 | 16* | 94 |
53 | 100 | 100 | 97 | 0 | 97* | 94 |
54 | 90 | 93 | 53 | 0 | 15* | 48 |
55 | 99* | 39* | 0* | - | 59* | -- |
56 | 95 . | 97 | 94 | 99 | 45* | 0 |
57 | 100 | 99 | 100 | ND | 100* | 0 |
·· · ·· ···· ·· »«·· ·· · ·
Če
288
Test A | TestB | Test C | Test D | Test E | Test |
84 | 67 | 0 | 24 | 0* | 0 |
100* | 100* | 78* | - | 100* | - |
98 | 100 | 74 | 88 | 9* | 0 |
97 | 100 | 99 | ND | 85* | 0 |
98 | 100 | 97 | 100 | - | 0 |
92 | 86 | 32 | 90 | 3* | 0 |
100 | 100 | 97 | 86 | 42* | 95 |
98 | 100 | 86 | 24 | 96* | 83 |
100 | 100 | 94 | 46 | 49* | 0 |
99 | : íoo | 97 | 0 | 82* | 0 |
98 | 97 | 52 | ND | - | 0 |
95 | 97 | 52 | ND | - | 0 |
97 | 94 | 52 | 86 | - | 0 |
100 | 94 | 53 | ND | 37* | 95 |
80** | 97** | 53** | 25‘* | - | 0** |
100 | 100 | 94 | 100a | - | 83 |
97 | 100 | 86 | 97 | - | 0 |
99 | 99 | 74 | 93 | 12* | 0 |
100 | 100 | 97 | 100 | 68* | 0 |
100 | 100 | 74 | ND | 40* | 94 |
99 | 97 | 86 | ND | 94* | 69 |
86 | 86 | 0 | ND | 65* | 6 |
100 | 100 | 94 | 100 | 100* | 98 |
98 | 99 | 94 | 9 | 71* | 90 |
100 | 100 | 99 | ND | 100* | 0 |
100 | 100 | 91 | ND | 72* | 0 |
100 | 99 | 86 | ND | 83* | 0 |
100 | 97 | 53 | ND | 0* | 0 |
100 | 100 | 94 | ND | 45* | 0 |
100 | 100 | 86 | ND | 69* | 0 |
100 | 100 | 100 | ND | 73* | 0 |
100 | 100 | 100 | ND | 100* | 98 |
100 | 94 | 86 | 91 | 15* | 83 |
100 | 99 | 100 | 100 | 4* | 0 |
100 | 97 | 91 | 83a | 31* | 0 |
100 | 86 | 91 | 96a | 84a>* | 0 |
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Slouč.
č. | Test A | TestB | Test C | Test D | Test E | Test F |
95 | 100 | 99 | 99 | 96 | 38* | 98 |
96 | 100 | 99 | 86 | 99a | 80* | 98 |
97 | 100 | 99 | 74 ' | ND | - | 0 |
98 | 100 | 94 | 53 | 46 | - | 83 |
99 | 99 | 100 | 99 | ND | 100* | 83 |
100 | 100 | 100 | 100 | 100 | 94* | 0 |
101 | 100 | 100 | 97 | 99 | 100*. | 0 |
102 | 38 | 0 | 0 | 0 | - | 0 |
103 | 38 | 0 | 0 | 88 | - | 0 |
104 | 100 | 100 | 97 | ND | 0 | |
105 | 100 | 100 | 100 | ND | - | 85 |
106 | 100 | 100 | 97 | ND | - | 55 |
107 | 98a | 100a | 100 | 71 | 100* | 97 |
108 | 98 | 97 | 94 | ND | 1* | 20 |
109 | 98 | 100 | 90 | 70 | 100a>* | 0 |
110 | 98 | 100 | 97 | 100 | 100* | 0 |
111 | 100 | 100 | 97 | 100 | 68* | 0 |
112 | 100 | 100 | 100 | 98 | 70* | 0 |
113 | 30 | 0 | 0 | 0 | - | 0 |
114 | 100 | 100 | 97 | 100a | 43* | 74 |
116 | 100 | 100 | 88 | ND | - | 0 |
117 | 100 | 100 | 97 | 100 | - | 98 |
118 | 100 | 100 | 100 | 93 | - | 99 |
119 | 100 | 100 | 94 | 93 | - | 0 |
120 | 99 | 100 | 97 | 100 | -- | 98 |
121 | 99 | 99 | 94 | ND | - | 98 |
124 | 100** | 100** | 97** | 92** | - | 98** |
125 | 100 | 99 | 53 | 0 | — | 36 |
a Ukazuje 20% spálení rostlin * Testováno při 10 ppm (odpovídá 25 g/ha) ** Testováno při 40 ppm (odpovídá 100 g/ha)
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Tabulka B
290
Porovnání účinnosti na pšeničném padlí (WPM)b
Sloučenina A Sloučenina B (WO 97/00612 (WO 96/38425
Sloučenina 13 Sloučenina I
Indexová tabulka C) Tabulka 1)
Dávka (ppm) 10
Sloučenina A 9
Sloučenina B 100
Sloučenina 13c 100 b Protokol testu je popsán v Testu A c Číslo označuje popis sloučeniny v Indexové tabulce A
Test G
Spodoptera frugiperda
Připravily se testované jednotky, z nichž každá sestávala z H.I.S. (rázuvzdorný styren) plotny se šestnácti jamkami. Do dvanácti jamek se umístil vlhký filtrační papír a vzorek listu měsíční fazole o velikosti přibližně 8 cm2. Do zbývajících čtyř jamek se umístila půlcentimetrová
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291 ;
vrstva obilných klíčků. Patnáct až dvacet larev Spodoptera frugiperda ve třetím instáru se umístilo do 230ml umělohmotného kelímku. Roztoky všech testovaných sloučenin v rozpouštědle, které tvořil aceton a destilovaná voda v poměru 75:25, se rozprášily na plotnu a do kelímku. Postřik se provedl tak, že se plotna a kelímek dopravily pomocí dopravníkového pásu přímo pod plochou hydraulickou trysku, která vypouštěla postřik rychlostí 0,138 kg/ha účinné složky při tlaku 207 kPa. Hmyz se přemístil z 230ml kelímku na H.I.P. plotnu (jeden jedinec na jamku). Plotny se zakryly a udržovaly 48 hodin při teplotě 27°C a 50% vlhkosti, načež se provedl ve dvanácti jamkách, které obsahovaly listy měsíční fazole, odečet mortality. Z testovaných sloučenin vykazovaly sloučeniny 59, 79 a 112 80% nebo vyšší kontrolní účinnost. U čtyř zbývajících jamek se provedl odečet, který měl určit zpožděnou toxicitu 6. až
8. den. Z testovaných sloučenin vykazovaly sloučeniny 7, 59 a 112 80% nebo vyšší kontrolní účinnost.
Test H
Diabrotica undecimpunctata howardi
Připravily se testované jednotky, z nichž každá sestávala z 230ml plastikového kelímku obsahujícího 6,5cm2 špalík pšeničných klíčků. Testované jednotky se postříkaly způsobem popsaným v testu G jednotlivými roztoky testovaných sloučenin. Potom, co postřik na kelímcích umístilo pět larev ve druhém instáru.
zaschnul, se do každého kelímku Diabrotica undecimpunctata howardi Kelímky se udržovaly 48 hodin při teplotě 27°C a 50% relativní vlhkosti. Po uplynutí této doby se provedl odečet
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292 mortality. Stejné jednotky se odečetly 6. až 8. den, přičemž cílem těchto odečtu bylo určení opožděné toxicity. Z testovaných sloučenin vykazovaly sloučeniny 1, 5, 7, 8, 11, 12, 27, 34, 53, 57, 59, 71, 97, 101, 112 a 117 80% nebo vyšší kontrolní účinnost.
Test I
Tetranychus urticae
Spodní strany kousků listů fazolu obecného, jejichž plocha byla přibližně 6,5 cm2 a jejichž spodní strany byly infikovány 25 až 30 dospělými jedinci Tetranychus urticae, se pomocí hydraulického rozprašovače postříkaly roztokem testované sloučeniny v rozpouštědle, které tvořil aceton a voda v poměru 75:25. Postřik se realizoval tak, že se jednotlivé listy dopravily pomocí dopravníkového pásu přímo pod plochou hydraulickou trysku, která vypouštěla postřik rychlostí 0,138 kg/ha účinné složky při tlaku 207 kPa. Kousky listů se potom umístily spodní stranou nahoru, na čtvereček mokré bavlny v Petriho misce, a okraj listového čtverce se přitiskl pomocí nůžek do bavlny tak, aby roztoči nemohli uniknout na neošetřený povrch listu. Testované jednotky se udržovaly 48 hodin při teplotě 27°C a 50% vlhkosti, načež se provedl odečet mortality. Z testovaných sloučenin vykazovaly sloučeniny 1, 10, 17, 34, 45, 46, 47, 55, 59, 64, 79, 84, 85, 95, 96, 98, 101, 112 a 124 80% nebo vyšší kontrolní účinnost.
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Test J
Peregrinus maidis
Testovací jednotka
Testovací jednotka sestávala z plastikového kelímku, který obsahoval 126 +/- 4 g sterilizované, nehnojené sassafrasové půdy (hlinitopísčitá půda). Jedno naklíčené kukuřičné semeno variety Pioneer 3394 se umístilo do důlku, hlubokého 2,5 cm á zahrnulo zeminou. Testovaná jednotka se zalila 15 ml destilované vody a na 4 dny umístila do uzavřeného boxu z plexiskla, který se nacházel ve skleníku. Ve skleníku byla teplota 24°C a 36% relativní vlhkost. Všechny testované jednotky se před analýzou opatřily víčkem, ve kterém byl proveden malý otvor.
Aplikace sloučeniny
Testované sloučeniny se formulovaly při koncentraci 200 ppm ve směsi acetonu a vody (20 % ku 80 %), která obsahovala 500 ppm povrchově aktivního činidla Ortho X-77. Sloučeniny se aplikovaly otvorem provedeným ve víku testovací jednotky pomocí rozprašovače zkompletovaného s tryskou, model 17690-1/8JJAU, a rozprašovací sadou sestávající z kapalinového uzávěru J2850 a vzduchového uzávěru J70 (Spray Systems, lne.). Rozprašovač pracoval při tlaku 0,083 až 0,089 MPa. Každá testovaná sloučenina se použila k postřiku dvou testovacích jednotek, přičemž pro postřik se použily vždy 2 ml testovaného roztoku. Po aplikaci postřiku se testovací jednotky umístily na 10 až 15 minut do větraného obalu, kde se nechaly vysušit.
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Infikace hmyzem/hodnocení
Po vysušení se na povrch zeminy každé testovací jednotky nasypala tenká vrstva bílého, křemenného písku, který umožnil lepší rozpoznání živého a mrtvého hmyzu. Každá jednotka se infikovala minimálně patnácti nymfami Peregrinus maidis, které byly přibližně 21 dní staré. Infikované testované jednotky se umístily do růstové komory, jejíž vnitřní teplota byla 22°C a relativní vlhkost 50 % a ve které se udržoval světelný režim světla ku tmě 16:8. Mortalita hmyzu se určovala 6 dnů po infikaci. Umírající jedinci se počítali mezi mrtvé jedince. Sloučenina 71 způsobila 80% mortalitu.
Tabulka C
Porovnání účinnosti na Diabrotica undecímpunctata howardi (SCRW)d
Sloučenina C Sloučenina D (WO 97/00612 Sloučenina 7
Indexová tabulka C)
Dávka (ppa)
250
Sloučenina C 87
Sloučenina 1Γ Sloučenina D Sloučenina 12e 100 60 93
Protokol testu je popsán v Testu H
Číslo označuje popis sloučeniny v Indexové tabulce A
Claims (12)
- PATENTOVÉ NÁROKY1. Způsob kontroly členovců, vyznačený tím, že zahrnuje uvedení členovců nebo jejich životního prostředí do kontaktu s arthropodicidně účinným množstvím sloučeniny obecného vzorce I, jejích W-oxidů a zemědělsky vhodných solí přičemž ve výše uvedeném obecném vzorciT znamenáTl r1(0)S\^xC00r5T2RlO.K^^^COOR5 Rl°xN<:^X'CONR6R5T3 nebo T401-859-99 Če * · · ·fc «··· ·· ·· • · · 0 · » · 0 · · · • · * · · ·· * ··*·♦· • · · ··· ·· • · · · · ·· 0 ·· ··296X znamená OR1, SfCJ^R1 nebo atom halogenu;A znamená atom kyslíku, atom síry, atom dusíku, NR5 nebo CR7;G znamená atom uhlíku nebo atom dusíku, za předpokladu že pokud G znamená atom uhlíku, potom A znamená atom kyslíku, atom síry nebo NR5 a pohyblivá dvojná vazba je navázána na G, pokud však G znamená atom dusíku, potom A znamená atom dusíku nebo CR7 a pohyblivá dvojná vazba je navázána na A;W znamená atom kyslíku, atom síry, aminoskupinu, N-alkylovou skupinu s 1 až 6 atomy uhlíku, nebo NO-alkylovou skupinu s 1 až 6 atomy uhlíku;Y znamená -0-, -CH20-, -0CH2-, -CHR11O-N=C (R8)-, přímou vazbu, -(CH2)r-, -C(R11)=C(R11)-, -CH2S(O)n-, -C(RS)=N-OCHR11-, -CHR11SC(R8)=N-, -C(R11)=N-N=C(R11)-, -chr11o-n=c(Rs)CH2S-, -CHR11O-N=C(R8)CH2O-, -C(R11)=N-N(CH3)-,-CHR^OC-(R8)=N-, -CHR^OC (=S)NR11-, -CHR11SC(=S)NR11-,-SCHR11- nebo -CHR11ON=C (R11) C (=N-OR1:L)-; a nasměrování vazby Y je definováno tak, že část znázorněná na levé straně vazby je navázána na fenylový kruh, který má R3 a R4 substituenty, a část na pravé straně vazby je navázána na Z;Z se nezávisle zvolí z:i) alkylové skupiny s 1 až 10 atomy uhlíku, halogenoalkylové skupiny s 1 až 10 atomy uhlíku nebo fenylové skupiny, přičemž všechny tyto skupiny mohou být případně substituovány R9 a případně substituovány jedním nebo více substituenty R10;• · · • ·01-859-99 Če
- 2 97 ii) pěti- nebo šestičlenného aromatického heterocyklického kruhu, přičemž každý heterocyklický kruh obsahuje 1 až 4 heteroatomy nezávisle zvolené z množiny zahrnující atom dusíku, atom kyslíku a atom síry, za předpokladu, že každý heterocyklický kruh neobsahuje více než 3 atomy dusíku, více než 1 atom kyslíku a více než 1 atom síry, přičemž každý aromatický heterocyklický kruh je případně substituován R9 a případně substituován jedním nebo více R10;iii) naftalenového kruhu případně substituovaného R9 a případně substituovaného jedním nebo více R10; a iv) tetrahydronaftalenového kruhu případně substituovaného R9 a případně substituovaného jedním nebo více R10;
znamená aikylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku nebo alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku; znamená atom vodíku aikylovou skupinu s Ί V i 1 az 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku, 01-859-99 Če • * A A* <»»· A*AAAA ·· A A · · tA « A ·«· A ’ < 4A A A A * « A A A A A A A *AAA AAA A «AA AAA A· A AA AA298 alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku, hydroxyskupinu, alkoxyskupinu s 1 až 2 atomy uhlíku nebo acetyloxyskupinu;R3 a R4 každý nezávisle znamenají atom vodíku, nebo methylovou skupinu za předpokladu, že R3 a R4 oba neznamenají atom vodíku a za předpokladu, že pokud T znamená T1, G znamená atom uhlíku a A znamená NR5, potom R4 znamená methylovou skupinu;R5 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku nebo alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku;R6 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomyuhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku, alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku, hydroxyskupinu, alkoxyskupinu s 1 až 2 atomy uhlíku nebo acetyloxyskupinu;R7 znamená atom vodíku, atom halogenu nebo methylovou skupinu;·· ··· ·01-859-99 Ce299R8 znamená atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku, alkoxyskupinu s 1 až alkylthioskupinu s 1 až 3 halogenoalkylovou skupinu s 1 až - 3 atomy uhlíku, atomy uhlíku, 3 atomy uhlíku, alkenylovou skupinu se 2 až 3 atomy uhlíku, alkinylovou skupinu se 2 až 3 atomy uhlíku, cyklopropylovou skupinu, kyanoskupinu nebo aminoskupinu;R9 znamená atom halogenu, alkylovou skupinu s\1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s genoalkoxyskupinu skupinu se 2 až atomy uhlíku, atomy uhlíku,1 až 6 atomy uhlíku, halos 1 až 6 atomy uhlíku, alkenylovou 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, alkylthioskupinu s 1 až 6 atomy uhlíku, halogenoalkylthioskupinu s 1 až 6 atomy uhlíku, alkylsulfinylovou skupinu s 1 až 6 atomy uhlíku, alkylsulfonylovou skupinu s 1 až 6 cykloalkylovou skupinu se 3 až 6 trimethylsilylovou skupinu, alkinylovou skupinu se 2 až 6 atomy uhlíku substituovanou trimethylsilylovou skupinou nebo cykloalkylovou skupinou se 3 až 6 atomy uhlíku, nebo fenylovou skupinu nebo fenoxyskupinu, přičemž každá fenylová skupina nebo fenoxyskupina může být případně substituována R12 a případně substituována jedním nebo více R13 za předpokladu, že pokud R9 znamená fenylovou skupinu nebo fenoxyskupinu, která je případně substituována R12 a případně substituována jedním nebo několika R13, potom T neznamená T1;znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, ·· ·· ···· a* *01-859-99 Ce300 alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu; neboR9 a R10 pokud jsou navázány na sousedící atomy uhlíku, potom mohou společně tvořit -CH2CH2O- nebo -OCH2CH2O-;každý R11 znamená nezávisle atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku nebo cyklopropylovou skupinu;R12 znamená atom halogenu, alkylovou skupinu s-l až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, alkylthioskupinu s 1 až 6 atomy uhlíku, halogenoalkylthioskupinu s 1 až č alkylsulfinylovou skupinu s 1 až alkylsulfonylovou skupinu s 1 až 6 atomy uhlíku nebo atomy uhlíku, atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku;R13 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu;m znamená 0, 1 nebo 2;n znamená 0, 1, nebo 2;r znamená 1, 2, 3 nebo 4; a s znamená 0 nebo 1, za předpokladu, že pokud T znamená T1, potom01-859-99 Če • · ·301i) pokud Y znamená -0-, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 6-chloro-4-pyrimidinylovou skupinu a 6-chloro2-pyrazinylovou skupinu;ii) pokud Y znamená přímou vazbu, X znamená atom chloru, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená CH2Br;iii) pokud Y znamená -O- a Z znamená 1,2,4-thiadiazol-5ylovou skupinu nebo 2-thiazolylovou skupinu případně substituovanou R9 a případně substituovanou R10, potom ani R9 ani R10 neznamená C(CH3)3;iv) pokud Y znamená -CH2O-N=C (CH3)-, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 3-(trimethylsilyl)fenylovou skupinu nebo 4-(trimethylsilyl)fenylovou skupinu;v) pokud Y znamená -CH2O-N=C (CH3)-, X znamená OMe, R3 znamená atom vodíku a R4 znamená methylovou skupinu, potom Z neznamená 3-(trimethylsilyl)fenylovou skupinu nebo 4-(trimethylsilyl)fenylovou skupinu; a vi) Y-Z neznamená alkylovou skupinu s 1 až 10 atomy uhlíku a alkoxyskupinu s 1 až 10 atomy uhlíku.2. Sloučenina obecného vzorce ITI ί01-859-99 Če302 ve kterémT znamená Rl(O)s \ coor5A—NV?COOR5 T2 Rl conr6r5 ψ4X znamená OR1, SfOJ^R1 nebo atom halogenu;A znamená atom kyslíku, atom síry, atom dusíku, NR5 nebo CR7;G znamená atom uhlíku nebo atom dusíku, za předpokladu že pokud G znamená atom uhlíku, potom A znamená atom kyslíku, atom síry nebo NR5 a pohyblivá dvojná vazba je navázána na G, pokud však G znamená atom dusíku, potom A znamená atom dusíku nebo CR7 a pohyblivá dvojná vazba je navázána na A;W znamená atom kyslíku, atom síry, aminoskupinu, N-alkylovou skupinu s 1 až 6 atomy uhlíku, nebo NO-alkylovou skupinu s 1 až 6 atomy uhlíku;• ·01-859-99 Če303Y znamená -0-, -CH2O-, -0CH2-, -CHR11O-N=C (R8) -, přímou vazbu, -(CH2)r-, -C (R11) =C (R11)-, -CH2S(O)n-, -C(RS)=N-OCHR11-, -CHR11SC (R8) =N~, -C (R11) =N~N=C (R11) -, -CHR^O-N^(R8)CH2S~, -CHR11O-N=C (R8) CH2O-, -C(R11)=N-N(CH3)-,-CHR^OC-(R8)=N-z -CHR11OC(=S)NR11-, -CHR11SC (=S) NR11-,-SCHR11- nebo -CHR11O-N=C (R11) C (=N-OR11)-; a nasměrováni vazby Y je definováno tak, že část znázorněná na levé straně vazby je navázána na fenylový kruh, který má R3 a R4 substituenty, a část na pravé straně vazby je navázána na Z;Z se nezávisle zvol! z:i) alkylové skupiny s 1 až 10 atomy uhlíku, halogenoalkylové skupiny s 1 až 10 atomy uhlíku nebo fenylové skupiny, přičemž všechny tyto skupiny mohou být případně substituovány R9 a případně substituovány jedním nebo více substituenty R10;ii) pěti- nebo šestičlenného aromatického heterocyklického kruhu, přičemž každý heterocyklický kruh obsahuje 1 až 4 heteroatomy nezávisle zvolené z množiny zahrnujíc! atom dusíku, atom kyslíku a atom siry, za předpokladu, že každý heterocyklický kruh neobsahuje vlče než 3 atomy dusíku, vlče než 1 atom kyslíku a více než 1 atom siry, přičemž každý aromatický heterocyklický kruh je případně substituován R9 a případně substituován jedním nebo více R10;iii) naftalenového kruhu případně substituovaného R9 a případně substituovaného jedním nebo více R10; a iv) tetrahydronaftalenového kruhu případně substituovaného R9 a případně substituovaného jedním nebo více R10;• · ·01-859-99 Če304R1 znamená alkylovou skupinu halogenoalkylovou skupinu alkenylovou skupinu se halogenoalkenylovou skupinu alkinylovou skupinu se halogenoalkinylovou skupinu cykloalkylovou skupinu se alkylkarbonylovou skupinu se alkoxykarbonylovou skupinu se
1 až 6 atomy uhlíku 1 až 6 atomy uhlíku až 6 atomy uhlíku 2 až 6 atomy uhlíku až 6 atomy uhlíku 2 až 6 atomy uhlíku až 6 atomy uhlíku až 4 atomy uhlíku neb' až 4 atomy uhlíku l; R2 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku, alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku, hydroxyskupinu, alkoxyskupinu s 1 až 2 atomy uhlíku nebo acetyloxyskupinu;R3 a R4 každý nezávisle znamenají atom vodíku, nebo methylovou skupinu za předpokladu, že R3 a R4 oba neznamenají atom vodíku a za předpokladu, že pokud T znamená T1, G znamená atom uhlíku a A znamená NR5, potom R4 znamená methylovou skupinu;R5 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku,305 halogenoalkinylovou skupinu cykloalkylovou skupinu se01-859-99 Če se 2 až 6 atomy uhlíku, 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku nebo alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku;R6 znamená atom vodíku, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku,alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkinylovou skupinu se 2 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, alkylkarbonylovou skupinu se 2 až 4 atomy uhlíku, alkoxykarbonylovou skupinu se 2 až 4 atomy uhlíku, hydroxyskupinu, alkoxyskupinu s 1 až 2 atomy uhlíku nebo acetyloxyskupinu;R7 znamená atom vodíku, atom halogenu nebo methylovou skupinu;R8 znamená atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku, alkoxyskupinu s alkylthioskupinu s 1 halogenoalkylovou skupinu1 až 3 atomy uhlíku, až 3 atomy uhlíku, 3 1 až 3 atomy uhlíku, alkenylovou skupinu se 2 až 3 atomy uhlíku, alkinylovou skupinu se 2 až 3 atomy uhlíku, cyklopropylovou skupinu, kyanoskupinu nebo aminoskupinu;R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 201-859-99 Če·· ··· ·· ♦ ·· ·· 30 6 až 6 atomy uhlíku, alkylthioskupinu s 1 až 6 atomy uhlíku, halogenoalkylthioskupinu s 1 až 6 atomy uhlíku, alkylsulfinylovou skupinu s 1 až 6 atomy uhlíku, alkylsulfonylovou skupinu s 1 až 6 atomy uhlíku, cykloalkylovou skupinu se 3 až 6 atomy uhlíku, trimethylsilylovou skupinu, alkinylovou skupinu se 2 až 6 atomy uhlíku substituovanou trimethylsilylovou skupinou nebo cykloalkylovou skupinou se 3 až 6 atomy uhlíku, nebo fenylovou skupinu nebo fěnoxyskupinu, přičemž každá fenylová skupina nebo fenoxyskupina může být případně substituována R12 a případně substituována jedním nebo více R13 za předpokladu, že pokud R9 znamená fenylovou skupinu nebo fěnoxyskupinu, která je případně substituována R12 a případně substituována jedním nebo několika R13, potom T neznamená T1;R10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu; neboR9 a R10 pokud jsou navázány na sousedící atomy uhlíku, potom mohou společně tvořit -CH2CH2O- nebo -OCH2CH2O-;každý R11 znamená nezávisle atom vodíku, alkylovou skupinu s 1 až 3 atomy uhlíku nebo cyklopropylovou skupinu;R12 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku, alkenylovou skupinu se 2 až 6 atomy uhlíku, halogenoalkenylovou skupinu se 2 až 6 atomy uhlíku, alkinylovou skupinu se 2 až 6 atomy • · • · uhlíku, alkylthioskupinu s halogenoalkylthioskupinu s 1 alkylsulfinylovou skupinu s alkylsulfonylovou skupinu s 1 cykloalkylovou skupinu se 3 až01-859-99 Če3071 až 6 atomy uhlíku, až 6 atomy uhlíku,1 až 6 atomy uhlíku, až 6 atomy uhlíku nebo6 atomy uhlíku;R13 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkoxyskupinu s 1 až 6 atomy uhlíku nebo kyanoskupinu;znamená 0, znamená 0, znamená 1,1 nebo 2;1, nebo 2;2, 3 nebo 4; a s znamená 0 nebo 1;za předpokladu, že (a) pokud T znamená T1, potomi) pokud Y znamená -0-, X znamená OMe, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená 6-chloro-4-pyrimidinylovou skupinu a 6-chloro-2-pyrazinylovou skupinu;ii) pokud Y znamená přímou vazbu, X znamená atom chloru, R3 znamená methylovou skupinu a R4 znamená atom vodíku, potom Z neznamená CH2Br;iii) pokud Y znamená -0- a Z znamená 1,2,4thiadiazol-5-ylovou skupinu nebo 2-thiazolylovou skupinu případně substituovanou R9 a případně01-859-99 Če • · · » ► · · · ► · · · • · · · · · • · • · · ·308 substituovanou R10, potom ani R9 ani R10 neznamená c(ch3)3;iv) Y-Z neznamená alkylovou skupinu s 1 až 10 atomy uhlíku a alkoxyskupinu s 1 až 10 atomy uhlíku;v) pokud Y znamená -CH2O-N=C (CH3)-, X znamená OMe, R3 znamená methylovou skupinu _ a R4 znamená atom vodíku, potom Z neznamená 3-(trifluoromethyl)fenyl, 3-(trimethylsilyl)fenyl nebo 4-(trimethylsilyl)fenyl;vi) pokud Y znamená -CH2O-N=C (CH3)-, X znamená OMe, R3 znamená atom vodíku a R4 znamená methylovou skupinu, potom Z neznamená 3(trifluoromethyl)fenyl, 3-(trimethylsilyl)fenyl nebo 4-(trimethylsilyl)fenyl;vii) pokud Z znamená 2-naftalenylovou skupinu nebo 5,6,7,8-tetrahydro-2-naftalenylovou skupinu, potom Y neznamená -CH2O- a -CH2O-N=C (CH3)-;viii) pokud Y znamená -CH2O-, R3 znamená methylovou skupinu, Z znamená fenylovou skupinu substituovanou R9 v poloze 2 a R9 znamená methylovou skupinu nebo atom halogenu, potom je Z substituován alespoň jedním R10, který neznamená methylovou skupinu a halogen; a ix) pokud Y znamená -CH2O-, R3 znamená methylovou skupinu, Z znamená fenylovou skupinu substituovanou R10 v poloze 2 a R10 znamená methylovou skupinu nebo atom halogenu, potom je Z substituo01-859-99 Če309 ván alespoň jedním R9 nebo R10, kterým není methylová skupina a atom halogenu;(b) pokud T znamená T2, potomi) Y neznamená -OCH2-, -C (R11) =C (R11) - -0-,-(CH2)r- a -SCHR11-;ii) pokud Y znamená -CH20-, potom Z znamená pyrimidinylovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo několika R10; a iii) pokud Y znamená -CH2O-N=C (CH3)-, potom s znamená 1;(c) pokud T znamená T3, potomY neznamená -SCHR11- a -CH20-; a (d) pokud T znamená T4 * *, potomi) Y neznamená -C (R11) =C (R11) - a -CH2S(O)n~; a ii) pokud Y znamená -CH2O-, potom Z znamená naftalenylovou skupinu případně substituovanou R9 a případně substituovanou jedním nebo více R10;její N-oxidy a zemědělsky vhodné soli.3. Sloučenina podle nároku 2, vyznačená tím, žeT znamená T1;A znamená atom dusíku;01-859-99 Če310G znamená atom dusíku;Y znamená -O-;Z znamená fenylovou skupinu, pyridinylovou skupinu, thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; aR10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku. - 4. Sloučenina podle nároku 2, vyznačená
m , že T znamená T1; A znamená atom dusíku; G znamená atom dusíku; Y znamená -CH2O-; Z znamená fenylovou s thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;• · • · ·01-859-99 Če311R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; aR10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku. - 5. Sloučenina podle nároku 2, vyznačená tím, žeT znamená T1;A znamená atom dusíku;G znamená atom dusíku;Y znamená -CH2O-N=C(R8) -;Z znamená fenylovou skupinu, pyridinylovou skupinu, thiazolylovou skupinu nebo thiadiazolylovou skupinu, přičemž každá z nich je případně substituována R9 a případně substituována jedním nebo více R10;R8 znamená methylovou skupinu;R9 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku; aR10 znamená atom halogenu, alkylovou skupinu s 1 až 6 atomy uhlíku, alkoxyskupinu s 1 až 6 atomy uhlíku, • ·01-859-99 Če312 halogenoalkylovou skupinu s 1 až 6 atomy uhlíku nebo halogenoalkoxyskupinu s 1 až 6 atomy uhlíku.
- 6. Sloučenina podle nároku 2, vyznačená tím, žeT znamená T1;A znamená atom dusíku;G znamená atom dusíku;Y znamená -0-, -CH20- nebo -CH20-N=C (R8)-;Z znamená thienyl případně substituovaný R9 a případně substituovaný jedním nebo více R10;R8 znamená methylovou skupinu;R9 znamená atom halogenu nebo alkylovou skupinu s 1 až 3 atomy uhlíku; aR10 znamená atom halogenu nebo alkylovou skupinu s 1 až 3 atomy uhlíku.
- 7. Sloučenina podle nároku 6, vyznačená tím, že Y znamená -0-.
- 8. Sloučenina podle nároku 2, vyznač tím, že se zvolí z množiny tvořené:» · »» »1 • ·01-859-99 Če3134-[2-(3-fluorofenoxy)-6-methylfenyl]-2,4-dihydro-5methoxy-2-methyl-37í-l, 2,4-triazol-3-on;2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(3methylfenoxy) fenyl] -31Í-1,2,4-triazol-3-on;2.4- dihydro-5-methoxy-2-methyl-4-(2-methyl-6fenoxyfenyl) -377-1,2,4-triazol-3-on;2.4- dihydro-5-methoxy-2-methyl-4- [2-methy-l-6- (4methylfenoxy) fenyl] -377-1, 2,4-triazol-3-on;2, 4-dihydro-5-methoxy-2-methyl-4-[6-methyl-2-[3(trifluoromethyl) fenoxy] fenyl] -377-1, 2,4-triazol-3on;2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-[[[[1-[4(trifluoromethyl)-2-pyridinyl]ethyliden]amino]oxy]methyl] fenyl] -377-1,2,4-triazol-3-on;4-[2-[[[[1-[2-fluoro-5-(trifluoromethyl)fenyl]ethyliden] amino]oxy]methyl]-6-methylfenyl]-2,4-dihydro-5methoxy-2-methyl-377-l, 2,4-triazol-3-on;4-[2-[[[[1-(2-fluoro-5-methylfenyl)ethyliden]amino]oxy]methyl]-6-methylfenyl]-2,4-dihydro-5-methoxy-2methyl-377-1, 2,4-triazol-3-on; a2.4- dihydro-5-methoxy-2-methyl-4-[2-methyl-6-(2thienyloxy) fenyl] -377-1, 2, 4-triazol-3-on.
- 9. Fungicidní kompozice, vyznačená tím, že obsahuje fungicidně účinné množství sloučeniny podle nároku 2 a alespoň jednu další složku zvolenou z množiny01-859-99 Če « «314 tvořené povrchově aktivním činidlem, pevným rozpouštědlem nebo kapalným rozpouštědlem.
- 10. Arthropodicidní kompozice, vyznačená tím, že obsahuje arthropodicidně účinné množství sloučeniny podle nároku 2 a alespoň jednu další složku zvolenou z množiny tvořené povrchově aktivním činidlem, pevným rozpouštědlem nebo kapalným rozpouštědlem.
- 11. Způsob kontroly rostlinných chorob způsobených fungálními rostlinnými patogeny, vyznačený tím, že zahrnuje aplikaci fungicidně účinného množství sloučeniny podle nároku 2 na rostlinu nebo její část nebo na semeno nebo semenáč rostlin.
- 12. Způsob kontroly členovců, vyznačený tím, že zahrnuje uvedení členovců nebo jejich životního prostředí do kontaktu s arthropodicidně účinným množstvím sloučeniny podle nároku 2.Zastupuj e:
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GB9924692D0 (en) * | 1999-10-20 | 1999-12-22 | Hoechst Schering Agrevo Gmbh | Wood treatment |
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WO2006089311A1 (en) | 2005-02-15 | 2006-08-24 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
BR112012015868A2 (pt) | 2009-12-11 | 2017-06-20 | Autifony Therapeutics Ltd | derivados de imidazolidinadiona |
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EP3670505A1 (de) * | 2018-12-18 | 2020-06-24 | Bayer AG | Substituierte pyridinyloxybenzole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
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KR20230005261A (ko) * | 2020-04-28 | 2023-01-09 | 바스프 에스이 | Qo 억제제 II 에 대한 내성을 부여하는 미토콘드리아 시토크롬 b 단백질 내에 아미노산 치환 F129L 을 함유하는 식물병원성 진균의 퇴치를 위한 스트로빌루린 유형 화합물의 용도 |
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EP3903584A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors iv |
EP3903582A1 (en) | 2020-04-28 | 2021-11-03 | Basf Se | Use of strobilurin type compounds for combating phytopathogenic fungi containing an amino acid substitution f129l in the mitochondrial cytochrome b protein conferring resistance to qo inhibitors ii |
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NZ213630A (en) * | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3545319A1 (de) * | 1985-12-20 | 1987-06-25 | Basf Ag | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE59108832D1 (de) * | 1990-12-31 | 1997-09-25 | Basf Ag | Verfahren zur Herstellung von Alpha-Ketocarbonsäureestern |
CA2103463A1 (en) * | 1991-06-05 | 1992-12-06 | Ian Christopher Richards | Propenoic acid derivatives |
PL315747A1 (en) * | 1993-11-19 | 1996-11-25 | Du Pont | Fungicidal cyclic amides |
IL115894A0 (en) * | 1994-12-08 | 1996-01-31 | Du Pont | Organosilanes and organogermanes and their use |
AU4869596A (en) * | 1995-02-24 | 1996-09-11 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
JP2771334B2 (ja) * | 1995-05-16 | 1998-07-02 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 殺菌・殺カビ性環状アミド類 |
JPH0948766A (ja) * | 1995-05-29 | 1997-02-18 | Sumitomo Chem Co Ltd | トリアゾロン誘導体、その用途およびその製造中間体 |
IL122670A0 (en) * | 1995-06-20 | 1998-08-16 | Du Pont | Arthropodicidal and fungicidal cyclic amides |
JPH0995486A (ja) * | 1995-07-26 | 1997-04-08 | Sumitomo Chem Co Ltd | トリアゾロン誘導体、その用途およびその製造中間体 |
-
1997
- 1997-11-25 AU AU54633/98A patent/AU5463398A/en not_active Abandoned
- 1997-11-25 KR KR1019990704639A patent/KR20000057254A/ko not_active Application Discontinuation
- 1997-11-25 CZ CZ991845A patent/CZ184599A3/cs unknown
- 1997-11-25 BR BR9713415-5A patent/BR9713415A/pt not_active IP Right Cessation
- 1997-11-25 WO PCT/US1997/021944 patent/WO1998023156A1/en not_active Application Discontinuation
- 1997-11-25 EP EP97948597A patent/EP0944314A1/en not_active Withdrawn
- 1997-11-25 JP JP52488998A patent/JP2001506984A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
KR20000057254A (ko) | 2000-09-15 |
WO1998023156A1 (en) | 1998-06-04 |
EP0944314A1 (en) | 1999-09-29 |
JP2001506984A (ja) | 2001-05-29 |
BR9713415A (pt) | 2000-04-18 |
AU5463398A (en) | 1998-06-22 |
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PD00 | Pending as of 2000-06-30 in czech republic |