KR100263576B1 - 살균성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 - Google Patents
살균성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 Download PDFInfo
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- KR100263576B1 KR100263576B1 KR1019920024827A KR920024827A KR100263576B1 KR 100263576 B1 KR100263576 B1 KR 100263576B1 KR 1019920024827 A KR1019920024827 A KR 1019920024827A KR 920024827 A KR920024827 A KR 920024827A KR 100263576 B1 KR100263576 B1 KR 100263576B1
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- NXRIDTLKJCKPOG-UHFFFAOYSA-N 1,4-dihydroimidazole-5-thione Chemical class S=C1CN=CN1 NXRIDTLKJCKPOG-UHFFFAOYSA-N 0.000 title claims abstract description 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000645 desinfectant Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 131
- 238000000034 method Methods 0.000 claims abstract description 58
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 238000002360 preparation method Methods 0.000 claims description 39
- -1 methylenedioxyphenyl Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 20
- 239000002585 base Substances 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000002540 isothiocyanates Chemical group 0.000 claims description 11
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 11
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000003849 aromatic solvent Substances 0.000 claims description 9
- 150000004292 cyclic ethers Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 229910052740 iodine Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- 239000004727 Noryl Substances 0.000 claims description 3
- 229920001207 Noryl Polymers 0.000 claims description 3
- SPTHOEKISABNFX-UHFFFAOYSA-N OC(=S)S=N Chemical compound OC(=S)S=N SPTHOEKISABNFX-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- OHOJRYNNXNLLOK-UHFFFAOYSA-N imidazolidine-2,4-dithione Chemical compound S=C1CNC(=S)N1 OHOJRYNNXNLLOK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical group C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical group 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000004965 peroxy acids Chemical group 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- 125000006575 electron-withdrawing group Chemical group 0.000 claims 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 230000001954 sterilising effect Effects 0.000 claims 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
- 239000000843 powder Substances 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 239000013543 active substance Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 19
- 239000008187 granular material Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000007900 aqueous suspension Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
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- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- LMVPQMGRYSRMIW-UHFFFAOYSA-N 3-anilino-5-methyl-2-methylsulfanyl-5-phenylimidazol-4-one Chemical compound CSC1=NC(C)(C=2C=CC=CC=2)C(=O)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
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- 238000012360 testing method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
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- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
- LNUBBKFSESILNF-UHFFFAOYSA-N 1-anilino-2-methylsulfanyl-4-phenyl-4h-imidazol-5-one Chemical compound CSC1=NC(C=2C=CC=CC=2)C(=O)N1NC1=CC=CC=C1 LNUBBKFSESILNF-UHFFFAOYSA-N 0.000 description 3
- DPHIUJNNMWIECT-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylideneamino]-2-phenylacetic acid Chemical compound CSC(SC)=NC(C(O)=O)C1=CC=CC=C1 DPHIUJNNMWIECT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
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- 150000002989 phenols Chemical class 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- UKQHBFWWIDTFEH-UHFFFAOYSA-N 5-methyl-3,5-diphenyl-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1C(C)(C=2C=CC=CC=2)NC(=S)N1C1=CC=CC=C1 UKQHBFWWIDTFEH-UHFFFAOYSA-N 0.000 description 2
- XUEJWBIKMKTDTL-UHFFFAOYSA-N 5-methyl-3,5-diphenylimidazolidine-2,4-dithione Chemical compound S=C1C(C)(C=2C=CC=CC=2)NC(=S)N1C1=CC=CC=C1 XUEJWBIKMKTDTL-UHFFFAOYSA-N 0.000 description 2
- ONWLSTBSKBIKEG-UHFFFAOYSA-N 5-methyl-5-phenyl-3-(pyridin-2-ylamino)-2-sulfanylideneimidazolidin-4-one Chemical compound O=C1C(C)(C=2C=CC=CC=2)NC(=S)N1NC1=CC=CC=N1 ONWLSTBSKBIKEG-UHFFFAOYSA-N 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
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- ADHKQMAZPNPPJA-UHFFFAOYSA-N methyl 2-isothiocyanato-2-phenylpropanoate Chemical compound COC(=O)C(C)(N=C=S)C1=CC=CC=C1 ADHKQMAZPNPPJA-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/18—Esters of dithiocarbamic acids
- C07C333/20—Esters of dithiocarbamic acids having nitrogen atoms of dithiocarbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9116200A FR2685328B1 (fr) | 1991-12-20 | 1991-12-20 | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR91-16200 | 1991-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR100263576B1 true KR100263576B1 (ko) | 2000-08-01 |
Family
ID=9420553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920024827A Expired - Lifetime KR100263576B1 (ko) | 1991-12-20 | 1992-12-19 | 살균성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 |
Country Status (32)
| Country | Link |
|---|---|
| EP (1) | EP0551048B1 (https=) |
| JP (1) | JP3462516B2 (https=) |
| KR (1) | KR100263576B1 (https=) |
| CN (1) | CN1035594C (https=) |
| AP (1) | AP405A (https=) |
| AT (1) | ATE221878T1 (https=) |
| AU (2) | AU651021B2 (https=) |
| BR (1) | BR9204699A (https=) |
| CA (1) | CA2085192C (https=) |
| CZ (1) | CZ287207B6 (https=) |
| DE (1) | DE69232719T2 (https=) |
| DK (1) | DK0551048T3 (https=) |
| EC (1) | ECSP920893A (https=) |
| EG (1) | EG19910A (https=) |
| ES (1) | ES2176186T3 (https=) |
| FI (1) | FI119732B (https=) |
| FR (1) | FR2685328B1 (https=) |
| HR (1) | HRP921456B1 (https=) |
| HU (1) | HU215384B (https=) |
| IL (2) | IL104091A (https=) |
| MA (1) | MA22747A1 (https=) |
| MX (1) | MX9207383A (https=) |
| MY (1) | MY110823A (https=) |
| NZ (1) | NZ245489A (https=) |
| PL (1) | PL170819B1 (https=) |
| PT (1) | PT551048E (https=) |
| RU (1) | RU2111207C1 (https=) |
| SI (1) | SI9200391B (https=) |
| SK (1) | SK283470B6 (https=) |
| TW (1) | TW267928B (https=) |
| YU (1) | YU49164B (https=) |
| ZA (1) | ZA929772B (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3931907A1 (de) * | 1989-09-25 | 1991-04-04 | Henkel Kgaa | Waessriges lackoverspray-schutzcoating fuer spritzkabinen sowie verfahren zu dessen herstellung |
| US6002016A (en) * | 1991-12-20 | 1999-12-14 | Rhone-Poulenc Agrochimie | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones |
| FR2706456B1 (fr) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2685328B1 (fr) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2698359B1 (fr) * | 1992-11-25 | 1995-10-27 | Rhone Poulenc Agrochimie | Derives de 2-alkoxy 2-imidazoline-5-ones fongicides. |
| FR2706455B1 (fr) * | 1993-06-18 | 1995-08-04 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| EP0642502B1 (en) * | 1992-05-22 | 2000-07-12 | E.I. Du Pont De Nemours And Company | Fungicidal imidazolinones |
| US6008370A (en) * | 1992-11-25 | 1999-12-28 | Rhone-Poulenc Agrochimie | Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones |
| FR2716192B1 (fr) * | 1994-02-17 | 1996-04-12 | Rhone Poulenc Agrochimie | Dérivés de 2-imidazoline-5-ones fongicides. |
| AU1892495A (en) * | 1994-03-09 | 1995-09-25 | Rhone-Poulenc Agrochimie | Pesticide substituted 2-imidazolinones |
| FR2721022B1 (fr) * | 1994-06-10 | 1996-07-19 | Rhone Poulenc Agrochimie | Dérivés de 5-imino 2-imidazolines fongicides. |
| FR2722499B1 (fr) * | 1994-07-13 | 1996-08-23 | Rhone Poulenc Agrochimie | Nouveaux derives de 2-imidazoline-5-ones fongicides |
| FR2722652B1 (fr) * | 1994-07-22 | 1997-12-19 | Rhone Poulenc Agrochimie | Composition fongicide comprenant une 2-imidazoline-5-one |
| JPH09183725A (ja) * | 1995-09-01 | 1997-07-15 | Pfizer Inc | ガン治療用治療剤 |
| FR2751327A1 (fr) | 1996-07-22 | 1998-01-23 | Rhone Poulenc Agrochimie | Intermediaires pour la preparation de 2-imidazoline-5-ones |
| UA61064C2 (uk) * | 1997-12-02 | 2003-11-17 | Рон-Пуленк Агро | Синергічна фунгіцидна композиція, що містить 2-інідазолін-5-он та спосіб боротьби з фітопатогенними грибками культур |
| UA70327C2 (uk) | 1998-06-08 | 2004-10-15 | Баєр Акціенгезельшафт | Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція |
| FR2783401B1 (fr) * | 1998-09-21 | 2000-10-20 | Rhone Poulenc Agrochimie | Nouvelles compositions fongicides |
| EP1092712A1 (en) * | 1999-10-13 | 2001-04-18 | E.I. Du Pont De Nemours And Company | Process for preparing fungicidal oxazolidinones and imidazolinones |
| EP1501355B1 (de) | 2002-04-24 | 2010-05-19 | Basf Se | Verwendung bestimmter alkoholalkoxylate als adjuvans für den agrotechnischen bereich |
| CN101863835B (zh) * | 2010-06-29 | 2012-10-10 | 渤海大学 | S-取代-5,5-二苯基-2-硫代海因衍生物的合成方法 |
| CN103081915A (zh) * | 2011-11-07 | 2013-05-08 | 深圳诺普信农化股份有限公司 | 一种杀菌组合物 |
| EP2622961A1 (en) | 2012-02-02 | 2013-08-07 | Bayer CropScience AG | Acive compound combinations |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2329276A1 (fr) * | 1975-10-29 | 1977-05-27 | Roussel Uclaf | Nouvelles imidazolidines substituees, procede de preparation, application comme medicament et compositions les renfermant |
| DE3305203A1 (de) * | 1983-02-16 | 1984-08-16 | Bayer Ag, 5090 Leverkusen | N-sulfenylierte hydantoine, ein verfahren zu ihrer herstellung und ihre verwendung als mikrobizide |
| DE3340595A1 (de) * | 1983-11-10 | 1985-05-23 | Hoechst Ag, 6230 Frankfurt | Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz |
| DE3634887A1 (de) * | 1986-10-14 | 1988-04-21 | Bayer Ag | 2-(5-oxo-2-imidazolin-2-yl)-pyridin-derivate |
| WO1988007040A1 (en) * | 1987-03-20 | 1988-09-22 | E.I. Du Pont De Nemours And Company | Fungicidal aminotriazoles and aminoimidazoles |
| KR0148128B1 (ko) * | 1989-04-21 | 1998-08-17 | 미리엄 디. 멕코나헤이 | 살진균성 옥사졸리디논 |
| TW201738B (https=) * | 1990-03-20 | 1993-03-11 | Sanofi Co | |
| FR2671348B1 (fr) * | 1991-01-09 | 1993-03-26 | Roussel Uclaf | Nouvelles phenylimidazolidines, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant. |
| FR2685328B1 (fr) * | 1991-12-20 | 1995-12-01 | Rhone Poulenc Agrochimie | Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| FR2706456B1 (fr) * | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| EP0642502B1 (en) * | 1992-05-22 | 2000-07-12 | E.I. Du Pont De Nemours And Company | Fungicidal imidazolinones |
-
1991
- 1991-12-20 FR FR9116200A patent/FR2685328B1/fr not_active Expired - Lifetime
-
1992
- 1992-02-17 EG EG78692A patent/EG19910A/xx active
- 1992-12-11 CA CA002085192A patent/CA2085192C/fr not_active Expired - Lifetime
- 1992-12-14 IL IL104091A patent/IL104091A/en not_active IP Right Cessation
- 1992-12-16 ES ES92420461T patent/ES2176186T3/es not_active Expired - Lifetime
- 1992-12-16 DK DK92420461T patent/DK0551048T3/da active
- 1992-12-16 AT AT92420461T patent/ATE221878T1/de active
- 1992-12-16 DE DE69232719T patent/DE69232719T2/de not_active Expired - Lifetime
- 1992-12-16 NZ NZ245489A patent/NZ245489A/en unknown
- 1992-12-16 EC EC1992000893A patent/ECSP920893A/es unknown
- 1992-12-16 MY MYPI92002315A patent/MY110823A/en unknown
- 1992-12-16 PT PT92420461T patent/PT551048E/pt unknown
- 1992-12-16 SI SI9200391A patent/SI9200391B/sl unknown
- 1992-12-16 MA MA23037A patent/MA22747A1/fr unknown
- 1992-12-16 EP EP92420461A patent/EP0551048B1/fr not_active Expired - Lifetime
- 1992-12-17 MX MX9207383A patent/MX9207383A/es unknown
- 1992-12-17 ZA ZA929772A patent/ZA929772B/xx unknown
- 1992-12-18 YU YU109092A patent/YU49164B/sh unknown
- 1992-12-18 BR BR9204699A patent/BR9204699A/pt not_active IP Right Cessation
- 1992-12-18 SK SK3753-92A patent/SK283470B6/sk not_active IP Right Cessation
- 1992-12-18 CZ CS19923753A patent/CZ287207B6/cs not_active IP Right Cessation
- 1992-12-18 HU HUP9204030A patent/HU215384B/hu not_active IP Right Cessation
- 1992-12-18 FI FI925763A patent/FI119732B/fi not_active IP Right Cessation
- 1992-12-18 RU RU92016214A patent/RU2111207C1/ru active
- 1992-12-18 TW TW081110177A patent/TW267928B/zh active
- 1992-12-18 AU AU30310/92A patent/AU651021B2/en not_active Ceased
- 1992-12-18 PL PL92297064A patent/PL170819B1/pl unknown
- 1992-12-19 KR KR1019920024827A patent/KR100263576B1/ko not_active Expired - Lifetime
- 1992-12-21 CN CN92115091A patent/CN1035594C/zh not_active Expired - Lifetime
- 1992-12-21 JP JP35634492A patent/JP3462516B2/ja not_active Expired - Fee Related
- 1992-12-21 AP APAP/P/1992/000466A patent/AP405A/en active
- 1992-12-22 HR HR921456A patent/HRP921456B1/xx not_active IP Right Cessation
-
1994
- 1994-10-07 AU AU74499/94A patent/AU671389B2/en not_active Ceased
-
1997
- 1997-08-04 IL IL12146597A patent/IL121465A0/xx not_active IP Right Cessation
Also Published As
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| Publication | Publication Date | Title |
|---|---|---|
| KR100263576B1 (ko) | 살균성 2-이미다졸린-5-온 및 2-이미다졸린-5-티온 유도체 | |
| US6344564B1 (en) | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones | |
| US6002016A (en) | Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones | |
| JPH08176112A (ja) | Ｎ，ｎ−ジ置換アニリン誘導体およびこれを有効成分とする農園芸用殺菌剤 | |
| AP496A (en) | Fungicidal 2-imidazolin-5-one and 2-imidazoline-5-thione derivatives. | |
| SI9500053A (en) | Fungicidal derivatives of 2-imidazoline-5-ones | |
| US6008370A (en) | Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones | |
| HU222255B1 (hu) | Fungicid hatású 2-imidazolin-5-on és 2-imidazolin-5-tion-származékok | |
| FR2721022A1 (fr) | Dérivés de 5-imino 2-imidazolines fongicides. |
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