CH615671A5 - Process for the preparation of 1,2,4-triazolidin-3-ones - Google Patents
Process for the preparation of 1,2,4-triazolidin-3-ones Download PDFInfo
- Publication number
- CH615671A5 CH615671A5 CH346775A CH346775A CH615671A5 CH 615671 A5 CH615671 A5 CH 615671A5 CH 346775 A CH346775 A CH 346775A CH 346775 A CH346775 A CH 346775A CH 615671 A5 CH615671 A5 CH 615671A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- thiadiazol
- triazolidin
- isocyanate
- thiadiazole
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 16
- NXHDERLYZNBICI-UHFFFAOYSA-N 1,2,4-triazolidin-3-one Chemical class O=C1NCNN1 NXHDERLYZNBICI-UHFFFAOYSA-N 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims description 55
- -1 diazol-2-yl Chemical group 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 41
- 230000002363 herbicidal effect Effects 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- CIZQYRDSPUHFOH-UHFFFAOYSA-N 4-(5-tert-butyl-3H-1,2,4-thiadiazol-2-yl)-2-methyl-1,2,4-triazolidin-3-one Chemical compound CN1NCN(C1=O)N1SC(=NC1)C(C)(C)C CIZQYRDSPUHFOH-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 56
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- 239000011521 glass Substances 0.000 description 43
- 239000011541 reaction mixture Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- 238000003756 stirring Methods 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 33
- 239000012948 isocyanate Substances 0.000 description 32
- 239000002244 precipitate Substances 0.000 description 31
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 30
- 150000002513 isocyanates Chemical class 0.000 description 29
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 238000010992 reflux Methods 0.000 description 22
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 239000004009 herbicide Substances 0.000 description 16
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000012047 saturated solution Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000006735 deficit Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000012010 growth Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 4
- 101000891579 Homo sapiens Microtubule-associated protein tau Proteins 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 102100040243 Microtubule-associated protein tau Human genes 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004965 chloroalkyl group Chemical group 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- VXIUIRAHDIUEFD-UHFFFAOYSA-N 1-amino-1-methyl-3-(4-nitrophenyl)urea Chemical compound CN(N)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 VXIUIRAHDIUEFD-UHFFFAOYSA-N 0.000 description 3
- JASKKIUPYPYADK-UHFFFAOYSA-N 1-amino-1-methyl-3-[4-(trifluoromethyl)phenyl]urea Chemical compound CN(N)C(=O)NC1=CC=C(C=C1)C(F)(F)F JASKKIUPYPYADK-UHFFFAOYSA-N 0.000 description 3
- GOJFPVSYYCKIRG-UHFFFAOYSA-N 1-amino-3-(3-chlorophenyl)-1-methylurea Chemical compound CN(N)C(=O)NC1=CC=CC(Cl)=C1 GOJFPVSYYCKIRG-UHFFFAOYSA-N 0.000 description 3
- POLSYOHZNXFPTI-UHFFFAOYSA-N 1-amino-3-(4-bromophenyl)-1-ethylurea Chemical compound C(C)N(N)C(=O)NC1=CC=C(C=C1)Br POLSYOHZNXFPTI-UHFFFAOYSA-N 0.000 description 3
- RUHIMRHOVRLRIE-UHFFFAOYSA-N 1-amino-3-(4-chloro-2-methylphenyl)-1-methylurea Chemical compound CN(N)C(=O)NC1=C(C=C(C=C1)Cl)C RUHIMRHOVRLRIE-UHFFFAOYSA-N 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 235000011331 Brassica Nutrition 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 3
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- 231100000331 toxic Toxicity 0.000 description 3
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- LZGIBSAZEYSSNF-UHFFFAOYSA-N 1-amino-1-methyl-3-(4-methylsulfanylphenyl)urea Chemical compound CN(N)C(=O)NC1=CC=C(C=C1)SC LZGIBSAZEYSSNF-UHFFFAOYSA-N 0.000 description 2
- CBJLEMTUHQQEIF-UHFFFAOYSA-N 1-amino-1-methyl-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]urea Chemical compound CN(N)C(=O)NC1=NN=C(C(F)(F)F)S1 CBJLEMTUHQQEIF-UHFFFAOYSA-N 0.000 description 2
- CRVXKRLUHVOJKF-UHFFFAOYSA-N 1-amino-3-(2-methoxyphenyl)-1-methylurea Chemical compound CN(N)C(=O)NC1=C(C=CC=C1)OC CRVXKRLUHVOJKF-UHFFFAOYSA-N 0.000 description 2
- GTBDPLDMHULSPI-UHFFFAOYSA-N 1-amino-3-(3,4-dichlorophenyl)-1-methylurea Chemical compound CN(N)C(=O)NC1=CC=C(Cl)C(Cl)=C1 GTBDPLDMHULSPI-UHFFFAOYSA-N 0.000 description 2
- CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 2
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 2
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 2
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
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- SPTATSOLTHNLQY-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-2-methyl-1,2,4-triazolidin-3-one Chemical compound CN1NCN(C1=O)C1=C(C=C(C=C1)Cl)C SPTATSOLTHNLQY-UHFFFAOYSA-N 0.000 description 2
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 2
- 101001074628 Homo sapiens Phosphatidylinositol-glycan biosynthesis class W protein Proteins 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 102100036253 Phosphatidylinositol-glycan biosynthesis class W protein Human genes 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
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- VKYBUEJAQKBUFU-UHFFFAOYSA-N hexylhydrazine Chemical compound CCCCCCNN VKYBUEJAQKBUFU-UHFFFAOYSA-N 0.000 description 2
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
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- JCIIKRHCWVHVFF-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine;hydrochloride Chemical compound Cl.NC1=NC=NS1 JCIIKRHCWVHVFF-UHFFFAOYSA-N 0.000 description 1
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
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- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
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- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
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- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- MYURAHUSYDVWQA-UHFFFAOYSA-N methyl n'-(4-chlorophenyl)-n,n-dimethylcarbamimidate Chemical compound COC(N(C)C)=NC1=CC=C(Cl)C=C1 MYURAHUSYDVWQA-UHFFFAOYSA-N 0.000 description 1
- QYPPRTNMGCREIM-UHFFFAOYSA-N methylarsonic acid Chemical compound C[As](O)(O)=O QYPPRTNMGCREIM-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
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- WKQYAIDXQNGNIQ-UHFFFAOYSA-N n'-(3,4-dichlorophenyl)-n,n-dimethylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=C(Cl)C(Cl)=C1 WKQYAIDXQNGNIQ-UHFFFAOYSA-N 0.000 description 1
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- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- YVZACCLFRNQBNO-UHFFFAOYSA-N pentylhydrazine Chemical compound CCCCCNN YVZACCLFRNQBNO-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 229940096826 phenylmercuric acetate Drugs 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000002373 plant growth inhibitor Substances 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 229940010115 simetone Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- NTOCDDPMRUNYHP-UHFFFAOYSA-M sodium;2-(2,4,5-trichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl NTOCDDPMRUNYHP-UHFFFAOYSA-M 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/455,697 US3931209A (en) | 1974-03-28 | 1974-03-28 | 2-Alkyl-4-thiadiazolyl-1,2,4-triazolidin-3-ones |
| US455710A US3890342A (en) | 1974-03-28 | 1974-03-28 | 2-Alkyl-4-aryl-1,2,4-triazolidin-3-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615671A5 true CH615671A5 (en) | 1980-02-15 |
Family
ID=27037957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH346775A CH615671A5 (en) | 1974-03-28 | 1975-03-18 | Process for the preparation of 1,2,4-triazolidin-3-ones |
Country Status (16)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4224929A1 (de) * | 1992-07-28 | 1994-02-03 | Bayer Ag | Heterocyclyltriazolinone |
-
1975
- 1975-02-10 CA CA219,673A patent/CA1032169A/en not_active Expired
- 1975-02-20 IL IL46670A patent/IL46670A/xx unknown
- 1975-02-26 AR AR257767A patent/AR219271A1/es active
- 1975-02-26 ES ES435089A patent/ES435089A1/es not_active Expired
- 1975-03-03 IT IT8428/75A patent/IT1050279B/it active
- 1975-03-11 DE DE19752510573 patent/DE2510573A1/de not_active Withdrawn
- 1975-03-17 PH PH16923A patent/PH13018A/en unknown
- 1975-03-18 CH CH346775A patent/CH615671A5/de not_active IP Right Cessation
- 1975-03-20 NL NL7503315A patent/NL7503315A/xx not_active Application Discontinuation
- 1975-03-26 SE SE7503545A patent/SE406084B/xx not_active IP Right Cessation
- 1975-03-26 NO NO751072A patent/NO141991C/no unknown
- 1975-03-26 EG EG165/75A patent/EG11654A/xx active
- 1975-03-27 AT AT236475A patent/AT341270B/de not_active IP Right Cessation
- 1975-03-27 JP JP50037397A patent/JPS50129746A/ja active Pending
- 1975-03-27 GB GB1284475A patent/GB1447471A/en not_active Expired
- 1975-03-28 FR FR7510027A patent/FR2289501A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU7897275A (en) | 1976-09-16 |
| FR2289501A1 (fr) | 1976-05-28 |
| GB1447471A (en) | 1976-08-25 |
| NL7503315A (nl) | 1975-09-30 |
| ES435089A1 (es) | 1977-01-16 |
| IL46670A (en) | 1978-08-31 |
| ATA236475A (de) | 1977-05-15 |
| JPS50129746A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-10-14 |
| NO751072L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-30 |
| NO141991B (no) | 1980-03-03 |
| IT1050279B (it) | 1981-03-10 |
| AT341270B (de) | 1978-01-25 |
| CA1032169A (en) | 1978-05-30 |
| NO141991C (no) | 1980-06-11 |
| DE2510573A1 (de) | 1975-10-02 |
| FR2289501B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-11 |
| IL46670A0 (en) | 1975-04-25 |
| PH13018A (en) | 1979-11-09 |
| EG11654A (en) | 1978-03-29 |
| AR219271A1 (es) | 1980-08-15 |
| SE7503545L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-09-29 |
| SE406084B (sv) | 1979-01-22 |
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