DD146539A5 - Fungizides oder wachstumsregulierendes mittel - Google Patents
Fungizides oder wachstumsregulierendes mittel Download PDFInfo
- Publication number
- DD146539A5 DD146539A5 DD79216255A DD21625579A DD146539A5 DD 146539 A5 DD146539 A5 DD 146539A5 DD 79216255 A DD79216255 A DD 79216255A DD 21625579 A DD21625579 A DD 21625579A DD 146539 A5 DD146539 A5 DD 146539A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- pyridyl
- thiazolidinone
- methyl
- chlorophenyl
- tetrahydro
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 239000004480 active ingredient Substances 0.000 claims abstract description 50
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 31
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract description 3
- -1 trifluoromethylphenyl Chemical group 0.000 claims description 210
- 239000000203 mixture Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000005059 halophenyl group Chemical group 0.000 claims description 14
- 125000006277 halobenzyl group Chemical group 0.000 claims description 13
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003944 tolyl group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 8
- 125000005394 methallyl group Chemical group 0.000 claims description 8
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 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
- HBJYXEMQCRRCKC-UHFFFAOYSA-N 5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound N1C(=O)C(C)SC1C1=CC=CN=C1 HBJYXEMQCRRCKC-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000005023 xylyl group Chemical group 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 5
- 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
- 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
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 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 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 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 description 3
- OKNSMTRKNXCYMM-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound ClC1=CC=CC=C1N1C(=O)CSC1C1=CC=CN=C1 OKNSMTRKNXCYMM-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
- 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 3
- KHEPTOMMPJGZMV-UHFFFAOYSA-N 3-(2-fluorophenyl)-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=C1F KHEPTOMMPJGZMV-UHFFFAOYSA-N 0.000 claims description 3
- KMIGEZOZLGPHIZ-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound ClC1=CC(Cl)=CC(N2C(CSC2C=2C=NC=CC=2)=O)=C1 KMIGEZOZLGPHIZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 3
- 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 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
- BTSWEQINKPKJPV-UHFFFAOYSA-N 3-(4-fluorophenyl)-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=C1 BTSWEQINKPKJPV-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 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
- CVJSWYDBZYHUST-UHFFFAOYSA-N 5-butyl-3-(4-chlorophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(CCCC)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 CVJSWYDBZYHUST-UHFFFAOYSA-N 0.000 claims description 3
- VIDAKRXJZPPKHW-UHFFFAOYSA-N 5-methyl-3-phenyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC=C1 VIDAKRXJZPPKHW-UHFFFAOYSA-N 0.000 claims description 3
- OXSQKYDXIGBFGA-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound FC1=CC=CC=C1CC1(C=2C=NC=CC=2)SCC(=O)N1 OXSQKYDXIGBFGA-UHFFFAOYSA-N 0.000 claims description 2
- SSHTVAXXNXZHHU-UHFFFAOYSA-N 2-pyridin-3-yl-3-[3-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one Chemical compound FC(F)(F)C1=CC=CC(N2C(CSC2C=2C=NC=CC=2)=O)=C1 SSHTVAXXNXZHHU-UHFFFAOYSA-N 0.000 claims description 2
- KMIMHJOXYRSZLO-UHFFFAOYSA-N 2-pyridin-3-yl-3-[4-(trifluoromethyl)phenyl]-1,3-thiazolidin-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(=O)CSC1C1=CC=CN=C1 KMIMHJOXYRSZLO-UHFFFAOYSA-N 0.000 claims description 2
- PDGFEZSVXMHFFO-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C=1C=C2OCOC2=CC=1CN1C(=O)CSC1C1=CC=CN=C1 PDGFEZSVXMHFFO-UHFFFAOYSA-N 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
- 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 2
- IJZABWMXLOGOIQ-UHFFFAOYSA-N 3-(3-bicyclo[2.2.1]heptanyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1C(C2)CCC2C1N1C(=O)CSC1C1=CC=CN=C1 IJZABWMXLOGOIQ-UHFFFAOYSA-N 0.000 claims description 2
- FIAUMLJPHYQRLK-UHFFFAOYSA-N 3-(3-nitrophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound [O-][N+](=O)C1=CC=CC(N2C(CSC2C=2C=NC=CC=2)=O)=C1 FIAUMLJPHYQRLK-UHFFFAOYSA-N 0.000 claims description 2
- MYJRTPKIVFITFQ-UHFFFAOYSA-N 3-(4-bromo-3-methylphenyl)-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(Br)C(C)=C1 MYJRTPKIVFITFQ-UHFFFAOYSA-N 0.000 claims description 2
- MNSCTHXIQASMMM-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-hexyl-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(CCCCCC)(C)SC(C=2C=NC=CC=2)N1C1=CC=C(Cl)C=C1 MNSCTHXIQASMMM-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- GEIMXTDFOVQQPO-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound C1=CC(SC)=CC=C1N1C(=O)CCSC1C1=CC=CN=C1 GEIMXTDFOVQQPO-UHFFFAOYSA-N 0.000 claims description 2
- VYNYAURPQOMFPH-UHFFFAOYSA-N 3-(4-nitrophenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)CSC1C1=CC=CN=C1 VYNYAURPQOMFPH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- DOAIRAOXVBGEHD-UHFFFAOYSA-N 3-cyclopentyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1C1CCCC1 DOAIRAOXVBGEHD-UHFFFAOYSA-N 0.000 claims description 2
- NKAXJUIBLVQXQQ-UHFFFAOYSA-N 3-cyclopropyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1CSC(C=2C=NC=CC=2)N1C1CC1 NKAXJUIBLVQXQQ-UHFFFAOYSA-N 0.000 claims description 2
- UEULHJFQOIBNIQ-UHFFFAOYSA-N 3-heptan-2-yl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1CC(=O)N(C(C)CCCCC)C1C1=CC=CN=C1 UEULHJFQOIBNIQ-UHFFFAOYSA-N 0.000 claims description 2
- YIIBPGYMGFQZDI-UHFFFAOYSA-N 3-heptan-2-yl-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1C(C)C(=O)N(C(C)CCCCC)C1C1=CC=CN=C1 YIIBPGYMGFQZDI-UHFFFAOYSA-N 0.000 claims description 2
- UGEMQCYLSHBGOR-UHFFFAOYSA-N 3-hexyl-2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound S1CCC(=O)N(CCCCCC)C1C1=CC=CN=C1 UGEMQCYLSHBGOR-UHFFFAOYSA-N 0.000 claims description 2
- YATXQSNNBLAEBU-UHFFFAOYSA-N 3-hexyl-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1C(C)C(=O)N(CCCCCC)C1C1=CC=CN=C1 YATXQSNNBLAEBU-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
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- DOYDNQFEOBEFRM-UHFFFAOYSA-N 5-methyl-2-pyridin-3-yl-3-[3-(trifluoromethylsulfanyl)phenyl]-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC(SC(F)(F)F)=C1 DOYDNQFEOBEFRM-UHFFFAOYSA-N 0.000 claims description 2
- RHEMYVBXOOVBTH-UHFFFAOYSA-N 5-methyl-3-(1-phenylethyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound C=1C=CC=CC=1C(C)N(C(C(C)S1)=O)C1C1=CC=CN=C1 RHEMYVBXOOVBTH-UHFFFAOYSA-N 0.000 claims description 2
- HRGCONXZSYTDQO-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=CC=C1C HRGCONXZSYTDQO-UHFFFAOYSA-N 0.000 claims description 2
- PERBFVKWVVOJFZ-UHFFFAOYSA-N 5-methyl-3-propan-2-yl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound S1C(C)C(=O)N(C(C)C)C1C1=CC=CN=C1 PERBFVKWVVOJFZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- CDMSTOYSGXMDMA-UHFFFAOYSA-N thiazin-4-one Chemical compound O=C1C=CSN=C1 CDMSTOYSGXMDMA-UHFFFAOYSA-N 0.000 claims description 2
- 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 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 2
- URVVZMJGQZDTAP-UHFFFAOYSA-N 5-methyl-3-(4-methylphenyl)-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1=CC=C(C)C=C1 URVVZMJGQZDTAP-UHFFFAOYSA-N 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
- PHMAYIMFUPPZRE-UHFFFAOYSA-N 2-methyl-1,3-thiazolidin-4-one Chemical compound CC1NC(=O)CS1 PHMAYIMFUPPZRE-UHFFFAOYSA-N 0.000 claims 1
- PGJGOUWJFZZDFR-UHFFFAOYSA-N 2-pyridin-3-yl-1,3-thiazinan-4-one Chemical compound N1=CC(=CC=C1)C1SCCC(N1)=O PGJGOUWJFZZDFR-UHFFFAOYSA-N 0.000 claims 1
- 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 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
- OLDHLYATBDJKHO-UHFFFAOYSA-N 3-cyclohexyl-5-methyl-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1C1CCCCC1 OLDHLYATBDJKHO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- KBMZILNUVIUVTH-UHFFFAOYSA-N 5-methyl-3-[(4-methylphenyl)methyl]-2-pyridin-3-yl-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(C=2C=NC=CC=2)N1CC1=CC=C(C)C=C1 KBMZILNUVIUVTH-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 108
- 238000002844 melting Methods 0.000 description 84
- 230000008018 melting Effects 0.000 description 84
- 238000004458 analytical method Methods 0.000 description 83
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 82
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- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 201000002266 mite infestation Diseases 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
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-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
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 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
- 239000012044 organic layer Substances 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000000377 silicon dioxide Substances 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000002352 surface water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- DTZWGYDVZJBUKO-UHFFFAOYSA-N thiazinan-4-one Chemical class O=C1CCSNC1 DTZWGYDVZJBUKO-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
- 201000008827 tuberculosis Diseases 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
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000004563 wettable powder Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95170878A | 1978-10-16 | 1978-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD146539A5 true DD146539A5 (de) | 1981-02-18 |
Family
ID=25492046
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216255A DD146539A5 (de) | 1978-10-16 | 1979-10-16 | Fungizides oder wachstumsregulierendes mittel |
| DD79220572A DD150747A5 (de) | 1978-10-16 | 1979-10-16 | Verfahren zur herstellung von thiazinonen |
| DD79220571A DD150746A5 (de) | 1978-10-16 | 1979-10-16 | Verfahren zur herstellung von 4-thiazolidinonen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79220572A DD150747A5 (de) | 1978-10-16 | 1979-10-16 | Verfahren zur herstellung von thiazinonen |
| DD79220571A DD150746A5 (de) | 1978-10-16 | 1979-10-16 | Verfahren zur herstellung von 4-thiazolidinonen |
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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