LU81779A1 - 1-thia-3-aza-4-ones substituees,leur preparation et leur utilisation en agriculture - Google Patents
1-thia-3-aza-4-ones substituees,leur preparation et leur utilisation en agriculture Download PDFInfo
- Publication number
- LU81779A1 LU81779A1 LU81779A LU81779A LU81779A1 LU 81779 A1 LU81779 A1 LU 81779A1 LU 81779 A LU81779 A LU 81779A LU 81779 A LU81779 A LU 81779A LU 81779 A1 LU81779 A1 LU 81779A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- pyridyl
- thiazolidinone
- methyl
- chlorophenyl
- tetrahydro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 25
- -1 1-methylhexyl Chemical group 0.000 claims description 185
- 150000001875 compounds Chemical class 0.000 claims description 147
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 claims description 79
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 78
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 78
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 77
- 239000000203 mixture Substances 0.000 claims description 67
- 241000196324 Embryophyta Species 0.000 claims description 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 29
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 230000000855 fungicidal effect Effects 0.000 claims description 22
- 241000233866 Fungi Species 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000005059 halophenyl group Chemical group 0.000 claims description 14
- 125000003944 tolyl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000006277 halobenzyl group Chemical group 0.000 claims description 11
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000005023 xylyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 claims description 8
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 8
- 230000003032 phytopathogenic effect Effects 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 230000001105 regulatory effect Effects 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 claims description 6
- IXDRVFHZVJDSQV-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 IXDRVFHZVJDSQV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000000417 fungicide Chemical group 0.000 claims description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- PLBVNSJJNYHVDG-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound N1C(=O)CSC1C1=CC=CN=C1 PLBVNSJJNYHVDG-UHFFFAOYSA-N 0.000 claims description 5
- BMJBELLWVIGIMS-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 BMJBELLWVIGIMS-UHFFFAOYSA-N 0.000 claims description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000007667 floating Methods 0.000 claims description 5
- 125000005394 methallyl group Chemical group 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
- SSAKGQNJRHHSTI-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound FC1=CC(F)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 SSAKGQNJRHHSTI-UHFFFAOYSA-N 0.000 claims description 3
- PIKAHYGYOOMJQP-UHFFFAOYSA-N 3-(2-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC=C1Cl PIKAHYGYOOMJQP-UHFFFAOYSA-N 0.000 claims description 3
- VUFPPBBMDVSOIC-UHFFFAOYSA-N 3-(2-methoxyphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound COC1=CC=CC=C1N1C(=O)CSC1C1=CC=CN=C1 VUFPPBBMDVSOIC-UHFFFAOYSA-N 0.000 claims description 3
- XQWCZCWZQPWTJY-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C1=C(C)C(C)=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 XQWCZCWZQPWTJY-UHFFFAOYSA-N 0.000 claims description 3
- DQIQRAHPLYCGHH-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methylsulfanyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(SC)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 DQIQRAHPLYCGHH-UHFFFAOYSA-N 0.000 claims description 3
- VJALOKGJVTUPDC-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 VJALOKGJVTUPDC-UHFFFAOYSA-N 0.000 claims description 3
- SEWDFCOTLXTTDC-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)CCSC1C1=CC=CN=C1 SEWDFCOTLXTTDC-UHFFFAOYSA-N 0.000 claims description 3
- LVVQHDBPUGBITE-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)CSC1C1=CC=CN=C1 LVVQHDBPUGBITE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
- UITXVOXYPYEUFH-UHFFFAOYSA-N 3-phenyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1C1=CC=CC=C1 UITXVOXYPYEUFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- ATFLDXXXIQQZOB-UHFFFAOYSA-N 2-ethyl-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C(C)C1(SC(C(N1)=O)C)C=1C=NC=CC=1 ATFLDXXXIQQZOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- DDBWNEIAVKATSU-UHFFFAOYSA-N 3-(1-cyclopentylpropan-2-yl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C=1C=CN=CC=1C1SCCC(=O)N1C(C)CC1CCCC1 DDBWNEIAVKATSU-UHFFFAOYSA-N 0.000 claims description 2
- SMIUVUVGXOZUFW-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound ClC1=CC(Cl)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 SMIUVUVGXOZUFW-UHFFFAOYSA-N 0.000 claims description 2
- UNMLFVDNUVMNOR-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=C(F)C=C1F UNMLFVDNUVMNOR-UHFFFAOYSA-N 0.000 claims description 2
- ZWARFPFTGKUASQ-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound FC1=CC=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 ZWARFPFTGKUASQ-UHFFFAOYSA-N 0.000 claims description 2
- AFVLTYGEAYPIGJ-UHFFFAOYSA-N 3-(2-fluorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound FC1=CC=CC=C1N1C(=O)CSC1C1=CC=CN=C1 AFVLTYGEAYPIGJ-UHFFFAOYSA-N 0.000 claims description 2
- QJVFNMFMVSTQDB-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 QJVFNMFMVSTQDB-UHFFFAOYSA-N 0.000 claims description 2
- QBWDMZNRZNMQFV-UHFFFAOYSA-N 3-(3-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC(Cl)=C1 QBWDMZNRZNMQFV-UHFFFAOYSA-N 0.000 claims description 2
- AYUWGYGMIASFRG-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-pyridin-3-yl-1,3-thiazinane-4-thione Chemical compound C1=CC(Cl)=CC=C1N1C(=S)CCSC1C1=CC=CN=C1 AYUWGYGMIASFRG-UHFFFAOYSA-N 0.000 claims description 2
- JLISADVZBVMDFV-UHFFFAOYSA-N 3-(4-chlorophenyl)-5,5-bis(methylsulfanyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(SC)(SC)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 JLISADVZBVMDFV-UHFFFAOYSA-N 0.000 claims description 2
- VYJNYACYBULOBN-UHFFFAOYSA-N 3-(4-chlorophenyl)-5,5-dimethyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)(C)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 VYJNYACYBULOBN-UHFFFAOYSA-N 0.000 claims description 2
- VEHUTGXBCKBCTJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound O=C1C(C)CSC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 VEHUTGXBCKBCTJ-UHFFFAOYSA-N 0.000 claims description 2
- CQUOMKILXGXKEY-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C1=CC(F)=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 CQUOMKILXGXKEY-UHFFFAOYSA-N 0.000 claims description 2
- UBFHMARVNLRWKZ-UHFFFAOYSA-N 3-(4-iodophenyl)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=C(I)C=C1 UBFHMARVNLRWKZ-UHFFFAOYSA-N 0.000 claims description 2
- LDOWHIQVJKFSRZ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 LDOWHIQVJKFSRZ-UHFFFAOYSA-N 0.000 claims description 2
- KTZBHMYUJDDTGM-UHFFFAOYSA-N 3-(4-methylphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 KTZBHMYUJDDTGM-UHFFFAOYSA-N 0.000 claims description 2
- XINIFEDCIUXAQE-UHFFFAOYSA-N 3-(4-phenoxyphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1C(C=C1)=CC=C1OC1=CC=CC=C1 XINIFEDCIUXAQE-UHFFFAOYSA-N 0.000 claims description 2
- SFXBVLZQUNNNHI-UHFFFAOYSA-N 3-(cyclohexylmethyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1CC1CCCCC1 SFXBVLZQUNNNHI-UHFFFAOYSA-N 0.000 claims description 2
- CRVPYJZAZBJEGC-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methyl]-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1CC1=CC=C(Cl)C=C1Cl CRVPYJZAZBJEGC-UHFFFAOYSA-N 0.000 claims description 2
- KOBQOYDZQUQKNF-UHFFFAOYSA-N 3-cyclohexyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1C1CCCCC1 KOBQOYDZQUQKNF-UHFFFAOYSA-N 0.000 claims description 2
- MCFNHNJTAQBIHP-UHFFFAOYSA-N 3-hexyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1CC(=O)N(CCCCCC)C1C1=CC=CN=C1 MCFNHNJTAQBIHP-UHFFFAOYSA-N 0.000 claims description 2
- SRGSUBSMKMCIPE-UHFFFAOYSA-N 3-nonyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1CC(=O)N(CCCCCCCCC)C1C1=CC=CN=C1 SRGSUBSMKMCIPE-UHFFFAOYSA-N 0.000 claims description 2
- DCPQQCXMYZGBOA-UHFFFAOYSA-N 3-propan-2-yl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1CC(=O)N(C(C)C)C1C1=CC=CN=C1 DCPQQCXMYZGBOA-UHFFFAOYSA-N 0.000 claims description 2
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- GFLPANAEQZSXTR-UHFFFAOYSA-N 5-methyl-2-pyridin-3-yl-3-[2-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC=C1C(F)(F)F GFLPANAEQZSXTR-UHFFFAOYSA-N 0.000 claims description 2
- AJRAPYPPNKTQSG-UHFFFAOYSA-N 5-methyl-3-(4-methylcyclohexyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1CCC(C)CC1 AJRAPYPPNKTQSG-UHFFFAOYSA-N 0.000 claims description 2
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- VXPPQXSJRLRLQC-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazin-4-one Chemical compound N1=CC(=CC=C1)C=1SC=CC(N=1)=O VXPPQXSJRLRLQC-UHFFFAOYSA-N 0.000 claims 3
- OPDAWLLQBPEAEJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 OPDAWLLQBPEAEJ-UHFFFAOYSA-N 0.000 claims 2
- CZXOZNJQAMYMLQ-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1CC1=CC=C(Cl)C=C1 CZXOZNJQAMYMLQ-UHFFFAOYSA-N 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- FNMGRVLXWOVONV-UHFFFAOYSA-N 1,3-thiazin-4-one Chemical compound O=C1C=CSC=N1 FNMGRVLXWOVONV-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- GNKZMKNBIFCHOF-UHFFFAOYSA-N 2-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound CC1(SCC(N1)=O)C=1C=NC=CC=1 GNKZMKNBIFCHOF-UHFFFAOYSA-N 0.000 claims 1
- BTNHJEXLUSIHLS-UHFFFAOYSA-N 2-pyridin-3-yl-3-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,3-thiazolidin-4-one Chemical compound FC(F)C(F)(F)OC1=CC=CC(N2C(CSC2C=2C=NC=CC=2)=O)=C1 BTNHJEXLUSIHLS-UHFFFAOYSA-N 0.000 claims 1
- WGJTUGLBWSVYAD-UHFFFAOYSA-N 2-pyridin-3-yl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazinan-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 WGJTUGLBWSVYAD-UHFFFAOYSA-N 0.000 claims 1
- QXPNLNFOSRLBGB-UHFFFAOYSA-N 3-(3-chloro-4-methylanilino)-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1NC1=CC=C(C)C(Cl)=C1 QXPNLNFOSRLBGB-UHFFFAOYSA-N 0.000 claims 1
- YXBJKWGEKWIELA-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound ClC1=CC=CC(N2C(CSC2C=2C=NC=CC=2)=O)=C1 YXBJKWGEKWIELA-UHFFFAOYSA-N 0.000 claims 1
- LYXGLHRVUUUGKF-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-2-pyridin-3-yl-2,4-dihydro-1,3-thiazol-4-ide 1-oxide Chemical compound ClC1=CC=C(C=C1)N1C(S(C(=[C-]1)C)=O)C=1C=NC=CC=1 LYXGLHRVUUUGKF-UHFFFAOYSA-N 0.000 claims 1
- GFLIYZYLRITJEV-UHFFFAOYSA-N 3-(4-methylphenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C1=CC(C)=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 GFLIYZYLRITJEV-UHFFFAOYSA-N 0.000 claims 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 125000004212 difluorophenyl group Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LRCFXGAMWKDGLA-UHFFFAOYSA-N dioxosilane;hydrate Chemical compound O.O=[Si]=O LRCFXGAMWKDGLA-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- 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
- A01N43/86—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95170878A | 1978-10-16 | 1978-10-16 | |
| US95170878 | 1978-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU81779A1 true LU81779A1 (fr) | 1980-01-24 |
Family
ID=25492046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU81779A LU81779A1 (fr) | 1978-10-16 | 1979-10-11 | 1-thia-3-aza-4-ones substituees,leur preparation et leur utilisation en agriculture |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP0010420B1 (cs) |
| JP (1) | JPS5555184A (cs) |
| AR (1) | AR225154A1 (cs) |
| AT (1) | ATA670079A (cs) |
| AU (1) | AU5165479A (cs) |
| BE (1) | BE879368A (cs) |
| BR (1) | BR7906634A (cs) |
| CH (1) | CH643842A5 (cs) |
| CS (1) | CS216535B2 (cs) |
| DD (3) | DD146539A5 (cs) |
| DE (1) | DE2967188D1 (cs) |
| DK (1) | DK434779A (cs) |
| ES (2) | ES485073A1 (cs) |
| FI (1) | FI793191A7 (cs) |
| FR (1) | FR2439197B1 (cs) |
| GB (1) | GB2031892B (cs) |
| GR (1) | GR71652B (cs) |
| HU (2) | HU187550B (cs) |
| IE (1) | IE48966B1 (cs) |
| IL (1) | IL58446A (cs) |
| LU (1) | LU81779A1 (cs) |
| NZ (1) | NZ191818A (cs) |
| PH (1) | PH15765A (cs) |
| PL (2) | PL125628B1 (cs) |
| PT (2) | PT70314A (cs) |
| RO (4) | RO82359A (cs) |
| SU (1) | SU1079175A3 (cs) |
| ZA (1) | ZA795488B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443455A (en) * | 1978-02-17 | 1984-04-17 | Imperial Chemical Industries Plc | Fungidical thiazolidinones |
| US4443454A (en) * | 1978-02-17 | 1984-04-17 | Imperial Chemical Industries Plc | Thiazolidinones |
| US4482712A (en) * | 1978-10-16 | 1984-11-13 | Eli Lilly And Company | Substituted 1-thia-3-aza-4-ones |
| EP0062612A1 (de) * | 1981-04-02 | 1982-10-13 | Ciba-Geigy Ag | Neue Thiazolinderivate |
| CA1229337A (en) * | 1982-04-02 | 1987-11-17 | Pieter T. Haken | Fungicidal heterocyclic compounds |
| JPS6061580A (ja) * | 1983-09-16 | 1985-04-09 | Zenyaku Kogyo Kk | 新規１，４−チアジン誘導体とその製造法 |
| JPS63225373A (ja) * | 1986-07-24 | 1988-09-20 | Sumitomo Pharmaceut Co Ltd | 新規チアゾリジン−４−オン誘導体およびその酸付加塩 |
| US4992455A (en) * | 1987-05-22 | 1991-02-12 | Sumitomo Pharmaceuticals Company, Limited | Thiazolidin-4-one derivatives useful for treating diseases caused by platelet activating factor |
| US5021435A (en) * | 1988-01-22 | 1991-06-04 | Sumitomo Pharmaceuticals Company, Limited | Certain pyridyl-thiazolidin-4-one having anti-ulcer activity |
| ATE154350T1 (de) * | 1990-10-17 | 1997-06-15 | Hoechst Schering Agrevo Gmbh | Pyrimidin-derivate, verfahren zu ihrer herstellung sie enthaltende mittel und ihre verwendung als fungizide |
| DE4243818A1 (de) * | 1992-12-23 | 1994-06-30 | Bayer Ag | 5-Aryl-1,3-thiazin-Derivate |
| AU4411399A (en) | 1998-06-05 | 1999-12-20 | Eli Lilly And Company | Potassium channel inhibitors |
| US6174908B1 (en) | 1999-05-10 | 2001-01-16 | Icagen, Inc. | Potassium channel inhibitors |
| US6506751B1 (en) | 1999-11-12 | 2003-01-14 | Millennium Pharmaceuticals, Inc. | Thiazolidinone compounds useful as chemokine inhibitors |
| TWI394753B (zh) * | 2006-03-17 | 2013-05-01 | Otsuka Pharma Co Ltd | 新穎替妥牟拉（ｔｅｔｏｍｉｌａｓｔ）晶體 |
| CN117143090A (zh) * | 2023-08-14 | 2023-12-01 | 中国科学院海洋研究所 | 含呋喃杂环的4-噻唑烷酮类化合物及其制备方法与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2910479A (en) * | 1958-01-06 | 1959-10-27 | Ciba Pharm Prod Inc | Certain 4-pyridyl thiazoline-2-ones and process |
| CH433322A (de) * | 1964-04-16 | 1967-04-15 | Dresden Arzneimittel | Verfahren zur Herstellung von peripher gefässerweiternd wirksamen Salzen des 2-(Pyridyl-(3'))-thiazolin- 2 |
| US3574841A (en) * | 1968-03-05 | 1971-04-13 | Mobil Oil Corp | Fungicidal methods using substituted nitropyridines |
| CA962269A (en) * | 1971-05-05 | 1975-02-04 | Robert E. Grahame (Jr.) | Thiazoles, and their use as insecticides |
| GB1539726A (en) * | 1974-12-31 | 1979-01-31 | Nitidandhaprabhas O | Treatment of animals suffering from mange |
| FR2356423A1 (fr) * | 1976-07-01 | 1978-01-27 | Oeriu Simion | Derives de l'acide thiazolidinecarboxylique, leur preparation et leur application comme medicaments |
| DE2965598D1 (en) * | 1978-02-17 | 1983-07-14 | Ici Plc | Thiazolidinone derivatives, their preparation, their pesticidal compositions and processes for treating plants |
-
1979
- 1979-10-10 AU AU51654/79A patent/AU5165479A/en not_active Abandoned
- 1979-10-10 CS CS796885A patent/CS216535B2/cs unknown
- 1979-10-10 NZ NZ191818A patent/NZ191818A/xx unknown
- 1979-10-11 LU LU81779A patent/LU81779A1/fr unknown
- 1979-10-11 AR AR278464A patent/AR225154A1/es active
- 1979-10-12 PH PH23161A patent/PH15765A/en unknown
- 1979-10-12 BE BE1/9563A patent/BE879368A/fr not_active IP Right Cessation
- 1979-10-14 IL IL58446A patent/IL58446A/xx unknown
- 1979-10-15 FI FI793191A patent/FI793191A7/fi not_active Application Discontinuation
- 1979-10-15 CH CH931179A patent/CH643842A5/fr not_active IP Right Cessation
- 1979-10-15 PT PT70314A patent/PT70314A/pt unknown
- 1979-10-15 GB GB7935748A patent/GB2031892B/en not_active Expired
- 1979-10-15 DE DE7979302215T patent/DE2967188D1/de not_active Expired
- 1979-10-15 FR FR7925597A patent/FR2439197B1/fr not_active Expired
- 1979-10-15 EP EP79302215A patent/EP0010420B1/en not_active Expired
- 1979-10-15 RO RO79105701A patent/RO82359A/ro unknown
- 1979-10-15 RO RO79105702A patent/RO82467A/ro unknown
- 1979-10-15 SU SU792831951A patent/SU1079175A3/ru active
- 1979-10-15 BR BR7906634A patent/BR7906634A/pt unknown
- 1979-10-15 IE IE1949/79A patent/IE48966B1/en unknown
- 1979-10-15 HU HU79@@84165A patent/HU187550B/hu unknown
- 1979-10-15 ZA ZA00795488A patent/ZA795488B/xx unknown
- 1979-10-15 RO RO7998943A patent/RO78231A/ro unknown
- 1979-10-15 AT AT0670079A patent/ATA670079A/de not_active Application Discontinuation
- 1979-10-15 DK DK434779A patent/DK434779A/da not_active Application Discontinuation
- 1979-10-15 GR GR60266A patent/GR71652B/el unknown
- 1979-10-15 HU HU79EI884A patent/HU185844B/hu unknown
- 1979-10-15 PT PT70313A patent/PT70313A/pt unknown
- 1979-10-15 RO RO7998944A patent/RO78232A/ro unknown
- 1979-10-16 DD DD79216255A patent/DD146539A5/de unknown
- 1979-10-16 DD DD79220572A patent/DD150747A5/de unknown
- 1979-10-16 DD DD79220571A patent/DD150746A5/de unknown
- 1979-10-16 PL PL1979218994A patent/PL125628B1/pl unknown
- 1979-10-16 PL PL1979231659A patent/PL127226B1/pl unknown
- 1979-10-16 ES ES485073A patent/ES485073A1/es not_active Expired
- 1979-10-16 JP JP13410079A patent/JPS5555184A/ja active Pending
- 1979-10-16 ES ES485072A patent/ES485072A0/es active Granted
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