DD147109A5 - Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen - Google Patents

Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen Download PDF

Info

Publication number: DD147109A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; general formula; acid; thiadiazole; item
Prior art date: 1978-11-03

Application number

DD79216618A

Other languages

German (de)

English (en)

Inventor

Hans-Rudolf Krueger

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-11-03

Filing date

1979-11-01

Publication date

1981-03-18

1979-11-01 Application filed by Schering Ag filed Critical Schering Ag

1981-03-18 Publication of DD147109A5 publication Critical patent/DD147109A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 30
238000002360 preparation method Methods 0.000 title claims abstract description 14
239000000126 substance Substances 0.000 title description 4
HQYZTGGAEAFKIO-UHFFFAOYSA-N thiadiazol-5-ylurea Chemical compound NC(=O)NC1=CN=NS1 HQYZTGGAEAFKIO-UHFFFAOYSA-N 0.000 title description 2
-1 1,2,3-thiadiazol-5-yl ureas Chemical class 0.000 claims abstract description 65
239000002253 acid Substances 0.000 claims abstract description 35
150000001412 amines Chemical class 0.000 claims abstract description 13
150000004820 halides Chemical class 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
LVAISXKBPDTJGC-UHFFFAOYSA-N N-hydroxythiadiazole-5-carboxamide Chemical class ONC(=O)C1=CN=NS1 LVAISXKBPDTJGC-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
229910052751 metal Inorganic materials 0.000 claims abstract description 3
239000002184 metal Substances 0.000 claims abstract description 3
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 5
239000004215 Carbon black (E152) Substances 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
BXCZJWHJYRELHY-UHFFFAOYSA-N thiadiazole-5-carboxylic acid Chemical class OC(=O)C1=CN=NS1 BXCZJWHJYRELHY-UHFFFAOYSA-N 0.000 claims description 3
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 2
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 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 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
150000002641 lithium Chemical group 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims 1
239000003495 polar organic solvent Substances 0.000 claims 1
235000013877 carbamide Nutrition 0.000 abstract description 9
238000004519 manufacturing process Methods 0.000 abstract description 5
150000003672 ureas Chemical class 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
230000008635 plant growth Effects 0.000 abstract 1
239000011814 protection agent Substances 0.000 abstract 1
230000001105 regulatory effect Effects 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
239000011593 sulfur Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012045 crude solution Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
HXABWNOBBYCXLG-UHFFFAOYSA-N 5-isocyanatothiadiazole Chemical compound O=C=NC1=CN=NS1 HXABWNOBBYCXLG-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
206010061926 Purulence Diseases 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000002837 defoliant Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
IVZZCUPPIUETNY-UHFFFAOYSA-N ethyl thiadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=NS1 IVZZCUPPIUETNY-UHFFFAOYSA-N 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
239000004476 plant protection product Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005406 washing Methods 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
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD79216618A 1978-11-03 1979-11-01 Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen DD147109A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782848330 DE2848330A1 (de)	1978-11-03	1978-11-03	Verfahren zur herstellung von 1,2, 3-thiadiazol-5-yl-harnstoffen

Publications (1)

Publication Number	Publication Date
DD147109A5 true DD147109A5 (de)	1981-03-18

Family

ID=6054085

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79216618A DD147109A5 (de)	1978-11-03	1979-11-01	Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen

Country Status (37)

Country	Link
US (1)	US4358596A (fr)
JP (1)	JPS5826913B2 (fr)
AR (1)	AR224253A1 (fr)
AT (1)	AT373885B (fr)
AU (1)	AU528407B2 (fr)
BE (1)	BE879830A (fr)
BG (1)	BG35046A3 (fr)
BR (1)	BR7907117A (fr)
CA (1)	CA1131639A (fr)
CH (1)	CH641793A5 (fr)
CS (1)	CS214675B2 (fr)
DD (1)	DD147109A5 (fr)
DE (1)	DE2848330A1 (fr)
DK (1)	DK459579A (fr)
EG (1)	EG14043A (fr)
ES (1)	ES485650A1 (fr)
FI (1)	FI793367A7 (fr)
FR (1)	FR2440947A1 (fr)
GB (1)	GB2039889B (fr)
GR (1)	GR74077B (fr)
HU (1)	HU183104B (fr)
IE (1)	IE49107B1 (fr)
IL (1)	IL58572A (fr)
IT (1)	IT1165334B (fr)
LU (1)	LU81834A1 (fr)
MX (1)	MX5790E (fr)
NL (1)	NL7907673A (fr)
NZ (1)	NZ191933A (fr)
PH (1)	PH15680A (fr)
PL (1)	PL130308B1 (fr)
PT (1)	PT70398A (fr)
RO (1)	RO78090A (fr)
SE (1)	SE7909017L (fr)
SU (1)	SU927114A3 (fr)
TR (1)	TR20548A (fr)
YU (1)	YU251479A (fr)
ZA (1)	ZA795893B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2920939A1 (de) *	1979-05-21	1980-11-27	Schering Ag	Verfahren zur herstellung von 5-mercapto-1,2,3-triazolen
DE3139505A1 (de) *	1981-10-01	1983-04-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	1,2,3,-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung
DE3139506A1 (de) *	1981-10-01	1983-04-21	Schering Ag, 1000 Berlin Und 4619 Bergkamen	1,2,3-thiadiazol-5-yl-harnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung
DE3319008A1 (de) *	1983-05-20	1984-11-22	Schering AG, 1000 Berlin und 4709 Bergkamen	1,2,3-thiadiazol-3-in-5-yliden-harnstoffderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wuchsregulatorischer und entblaetternder wirkung
US6166054A (en) *	1995-03-31	2000-12-26	Nihon Nohyaku Co., Ltd.	Agricultural and horticultural disease controller and a method for controlling the diseases
WO2000041698A1 (fr)	1999-01-13	2000-07-20	Bayer Corporation	DIPHENYLE UREES A SUBSTITUTION φ-CARBOXY ARYLE EN TANT QU'INHIBITEURS DE LA KINASE p38
US8124630B2 (en)	1999-01-13	2012-02-28	Bayer Healthcare Llc	ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
EP2324825A1 (fr)	2002-02-11	2011-05-25	Bayer Healthcare LLC	Arylurées dotées d'une activité d'inhibition de l'angiogenèse
UY28213A1 (es)	2003-02-28	2004-09-30	Bayer Pharmaceuticals Corp	Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos.
DK1626714T3 (da) *	2003-05-20	2007-10-15	Bayer Pharmaceuticals Corp	Dirarylurinstoffer mod sygdomme medieret af PDGFR
CN1856469B (zh)	2003-07-23	2013-03-06	拜耳医药保健有限责任公司	用于治疗和预防疾病和疾病症状的氟代ω-羧芳基二苯基脲

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD103124A5 (fr)	1972-03-23	1974-01-12
DE2636994C2 (de)	1976-08-13	1984-10-18	Schering AG, 1000 Berlin und 4709 Bergkamen	Verfahren zur Herstellung von 5-Amino-1,2,3-thiadiazol

1978
- 1978-11-03 DE DE19782848330 patent/DE2848330A1/de not_active Withdrawn
1979
- 1979-10-16 YU YU02514/79A patent/YU251479A/xx unknown
- 1979-10-17 NL NL7907673A patent/NL7907673A/nl not_active Application Discontinuation
- 1979-10-23 TR TR20548A patent/TR20548A/xx unknown
- 1979-10-24 BG BG045274A patent/BG35046A3/xx unknown
- 1979-10-26 FI FI793367A patent/FI793367A7/fi not_active Application Discontinuation
- 1979-10-26 NZ NZ191933A patent/NZ191933A/xx unknown
- 1979-10-29 EG EG659/79A patent/EG14043A/xx active
- 1979-10-29 IL IL58572A patent/IL58572A/xx unknown
- 1979-10-29 GB GB7937421A patent/GB2039889B/en not_active Expired
- 1979-10-29 LU LU81834A patent/LU81834A1/de unknown
- 1979-10-30 IT IT26898/79A patent/IT1165334B/it active
- 1979-10-30 MX MX798464U patent/MX5790E/es unknown
- 1979-10-31 DK DK459579A patent/DK459579A/da not_active Application Discontinuation
- 1979-10-31 AT AT0703179A patent/AT373885B/de active
- 1979-10-31 PT PT70398A patent/PT70398A/pt unknown
- 1979-10-31 SE SE7909017A patent/SE7909017L/xx not_active Application Discontinuation
- 1979-11-01 GR GR60384A patent/GR74077B/el unknown
- 1979-11-01 DD DD79216618A patent/DD147109A5/de unknown
- 1979-11-01 CA CA338,949A patent/CA1131639A/fr not_active Expired
- 1979-11-01 BR BR7907117A patent/BR7907117A/pt unknown
- 1979-11-02 CS CS797477A patent/CS214675B2/cs unknown
- 1979-11-02 JP JP54141441A patent/JPS5826913B2/ja not_active Expired
- 1979-11-02 RO RO7999125A patent/RO78090A/fr unknown
- 1979-11-02 ZA ZA00795893A patent/ZA795893B/xx unknown
- 1979-11-02 AR AR278768A patent/AR224253A1/es active
- 1979-11-02 CH CH987979A patent/CH641793A5/de not_active IP Right Cessation
- 1979-11-02 HU HU79SCHE702A patent/HU183104B/hu unknown
- 1979-11-02 SU SU792842379A patent/SU927114A3/ru active
- 1979-11-02 PL PL1979219405A patent/PL130308B1/pl unknown
- 1979-11-02 ES ES485650A patent/ES485650A1/es not_active Expired
- 1979-11-05 BE BE0/197972A patent/BE879830A/fr not_active IP Right Cessation
- 1979-11-05 AU AU52489/79A patent/AU528407B2/en not_active Ceased
- 1979-11-05 IE IE2112/79A patent/IE49107B1/en unknown
- 1979-11-05 FR FR7927192A patent/FR2440947A1/fr active Granted
- 1979-11-05 PH PH23243A patent/PH15680A/en unknown
1981
- 1981-01-21 US US06/226,899 patent/US4358596A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EG14043A (en)	1982-09-30
ES485650A1 (es)	1980-05-16
IL58572A (en)	1983-10-31
ZA795893B (en)	1980-12-31
CS214675B2 (en)	1982-05-28
ATA703179A (de)	1983-07-15
BE879830A (fr)	1980-05-05
JPS5826913B2 (ja)	1983-06-06
HU183104B (en)	1984-04-28
AU528407B2 (en)	1983-04-28
FI793367A7 (fi)	1981-01-01
FR2440947A1 (fr)	1980-06-06
IE49107B1 (en)	1985-08-07
US4358596A (en)	1982-11-09
SE7909017L (sv)	1980-05-04
NZ191933A (en)	1981-03-16
AT373885B (de)	1984-02-27
IE792112L (en)	1980-05-03
MX5790E (es)	1984-07-11
BG35046A3 (bg)	1984-01-16
TR20548A (tr)	1981-10-15
CH641793A5 (de)	1984-03-15
GB2039889A (en)	1980-08-20
GR74077B (fr)	1984-06-06
PT70398A (de)	1979-11-01
PL130308B1 (en)	1984-07-31
IT1165334B (it)	1987-04-22
RO78090A (fr)	1982-02-01
DE2848330A1 (de)	1980-05-14
PH15680A (en)	1983-03-11
IT7926898A0 (it)	1979-10-30
LU81834A1 (de)	1980-01-25
CA1131639A (fr)	1982-09-14
SU927114A3 (ru)	1982-05-07
DK459579A (da)	1980-05-04
YU251479A (en)	1983-04-30
JPS5566571A (en)	1980-05-20
FR2440947B1 (fr)	1983-09-16
AR224253A1 (es)	1981-11-13
IL58572A0 (en)	1980-01-31
AU5248979A (en)	1980-05-08
BR7907117A (pt)	1980-09-09
GB2039889B (en)	1983-04-13
PL219405A1 (fr)	1980-12-01
NL7907673A (nl)	1980-05-07

Publication	Publication Date	Title
DD147109A5 (de)	1981-03-18	Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen
DE2207549B2 (de)	1979-07-26	1-Aminouracile und deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE2712630A1 (de)	1978-09-28	1,3,4-thiadiazol-2-yl-harnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DE1670679C3 (de)	1973-10-18	4H-3,1-Benzoxazinderivate und Verfahren zu ihrer Herstellung
DD151061A5 (de)	1981-09-30	Verfahren zur herstellung von 5-mercapto-1,2,3-triazole
EP0068371B1 (fr)	1984-03-21	Procédé de préparation de thio-éthers
DE1246722B (de)	1967-08-10	Verfahren zur Herstellung von Harnstoffderivaten
DD146184A5 (de)	1981-01-28	Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen
DE2003145A1 (de)	1971-08-12	2-Acylamino-1,3,4-thiadiazol-(thi)one-(5),Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
EP0044420B1 (fr)	1984-11-28	Hydroxyalkyltriazolidine-1,2,4 diones-3,5 et leur procédé de préparation
DE2825194C2 (fr)	1989-01-26
LU81925A1 (de)	1980-02-29	Verfahren zur herstellung von 5-mercapio 1,2,3-triazolen
DE68919950T2 (de)	1995-06-22	S-(N-Alkoxycarbonyl, N-substituierte)aminomethylisothioharnstoff-Derivat.
DE2204767A1 (de)	1973-08-09	Benzoxazol - 2 - yl - substituierte 1.3.4 - thia - und - oxadiazole
DE2730325A1 (de)	1979-01-11	Carbanilsaeure-(3-ureido-phenyl)- ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel
CH647497A5 (en)	1985-01-31	Process for the preparation of O-substituted hydroxylamines
DE2233520A1 (de)	1973-01-25	Verfahren zur herstellung von penicillinund penicillinsulfoxidestern
EP0045371B1 (fr)	1984-02-22	Préparation de 1,2,4-triazolidine-3,5-diones substitués en position 4
DE1543942C (de)	1971-08-05	Verfahren zur Herstellung von 1 Oxa 2 methyl 3 carbonylarmno 4 tnia cyclohe xen(2)en
DD204026A5 (de)	1983-11-16	Wuchsregulatorische und entblaetternde mittel
DE3146300A1 (de)	1983-08-25	Thiazolo- und (1,3)thiazino(3,2-b)(1,2,4)triazine, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit selektiver herbizider wirkung
DE1670967A1 (de)	1971-02-25	Verfahren zur Herstellung von 3-Imino-1,2-benzisothiazolinen
DD243282A5 (de)	1987-02-25	Verfahren zur herstellung von 1,2,4-oxadiazolin-3-on-derivaten
DD234673A1 (de)	1986-04-09	Verfahren zur herstellung von 2,3,5-trisubstituierten 1,3,4-thiadiazolinen
DE3121288A1 (de)	1982-02-25	Neue substituierte 3,5-diamino-1,2,4-oxadiazole und 3,5-diamino-1,2,4-thiadiazole, verfahren zu ihrer herstellung und ihre verwendung