HU202516B - Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds - Google Patents
Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds Download PDFInfo
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- HU202516B HU202516B HU874437A HU443787A HU202516B HU 202516 B HU202516 B HU 202516B HU 874437 A HU874437 A HU 874437A HU 443787 A HU443787 A HU 443787A HU 202516 B HU202516 B HU 202516B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 15
- XARZSESQHPGTIA-UHFFFAOYSA-N thiophen-2-ylmethylthiourea Chemical class NC(=S)NCC1=CC=CS1 XARZSESQHPGTIA-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000003674 animal food additive Substances 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- -1 furfuryl Chemical group 0.000 claims description 28
- 235000013312 flour Nutrition 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 240000008042 Zea mays Species 0.000 claims description 10
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 235000010469 Glycine max Nutrition 0.000 claims description 7
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 6
- 150000002540 isothiocyanates Chemical class 0.000 claims description 6
- TXSVRMABOIMFTH-UHFFFAOYSA-N thiophen-2-ylthiourea Chemical compound NC(=S)NC1=CC=CS1 TXSVRMABOIMFTH-UHFFFAOYSA-N 0.000 claims description 6
- 235000021307 Triticum Nutrition 0.000 claims description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 5
- 235000009973 maize Nutrition 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 235000012054 meals Nutrition 0.000 claims description 4
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 claims description 4
- 235000019733 Fish meal Nutrition 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 240000004658 Medicago sativa Species 0.000 claims description 3
- 235000007238 Secale cereale Nutrition 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000004467 fishmeal Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 2
- 244000082988 Secale cereale Species 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 235000013372 meat Nutrition 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 244000046052 Phaseolus vulgaris Species 0.000 claims 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 239000006052 feed supplement Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- JUTZNFXHJFFMIR-UHFFFAOYSA-N 2-isothiocyanatothiophene Chemical compound S=C=NC1=CC=CS1 JUTZNFXHJFFMIR-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- 235000013343 vitamin Nutrition 0.000 description 6
- 239000011782 vitamin Substances 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- 230000004584 weight gain Effects 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 241000287828 Gallus gallus Species 0.000 description 5
- 241000283903 Ovis aries Species 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 239000001506 calcium phosphate Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000003502 gasoline Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 239000011573 trace mineral Substances 0.000 description 5
- 235000013619 trace mineral Nutrition 0.000 description 5
- 150000003722 vitamin derivatives Chemical class 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 108010001478 Bacitracin Proteins 0.000 description 3
- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- 235000019687 Lamb Nutrition 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 235000011941 Tilia x europaea Nutrition 0.000 description 3
- 229930003427 Vitamin E Natural products 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229960003071 bacitracin Drugs 0.000 description 3
- 229930184125 bacitracin Natural products 0.000 description 3
- CLKOFPXJLQSYAH-ABRJDSQDSA-N bacitracin A Chemical compound C1SC([C@@H](N)[C@@H](C)CC)=N[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]1C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2N=CNC=2)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)NCCCC1 CLKOFPXJLQSYAH-ABRJDSQDSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
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- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
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- 235000019743 Choline chloride Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
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- 230000003078 antioxidant effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 2
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- ZAUXSEINZZFHJQ-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(thiophen-2-ylmethyl)thiourea Chemical compound CC1=CC=CC(C)=C1NC(=S)NCC1=CC=CS1 ZAUXSEINZZFHJQ-UHFFFAOYSA-N 0.000 description 1
- MGJQDYLEYDAZMM-UHFFFAOYSA-N 1-benzyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C=1C=CC=CC=1CNC(=S)NCC1=CC=CS1 MGJQDYLEYDAZMM-UHFFFAOYSA-N 0.000 description 1
- OHIBLLMOWFJKRX-UHFFFAOYSA-N 1-cyclohexyl-3-(thiophen-2-ylmethyl)thiourea Chemical compound C1CCCCC1NC(=S)NCC1=CC=CS1 OHIBLLMOWFJKRX-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- JBDOSUUXMYMWQH-UHFFFAOYSA-N 1-naphthyl isothiocyanate Chemical compound C1=CC=C2C(N=C=S)=CC=CC2=C1 JBDOSUUXMYMWQH-UHFFFAOYSA-N 0.000 description 1
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- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- 229930003471 Vitamin B2 Natural products 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229950011175 aminopicoline Drugs 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000021052 average daily weight gain Nutrition 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229940037723 bran 1000 mg Drugs 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IDAGXRIGDWCIET-SDFKWCIISA-L disodium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IDAGXRIGDWCIET-SDFKWCIISA-L 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- MZSJGCPBOVTKHR-UHFFFAOYSA-N isothiocyanatocyclohexane Chemical compound S=C=NC1CCCCC1 MZSJGCPBOVTKHR-UHFFFAOYSA-N 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- LTAWCHATRSDECJ-UHFFFAOYSA-N n-(thiophen-2-ylmethylcarbamothioyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=S)NCC1=CC=CS1 LTAWCHATRSDECJ-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 235000012711 vitamin K3 Nutrition 0.000 description 1
- 239000011652 vitamin K3 Substances 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Husbandry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
| CH3625/88A CH676849A5 (enrdf_load_stackoverflow) | 1987-10-02 | 1988-09-29 | |
| YU01821/88A YU182188A (en) | 1987-10-02 | 1988-09-29 | Process for obtaining derivatives of (2-thienyl-methyl)-thiourea |
| IL87874A IL87874A0 (en) | 1987-10-02 | 1988-09-29 | (2-thienyl-methyl)-thiourea derivatives,their preparation and feed additives containing them |
| AU23329/88A AU607811B2 (en) | 1987-10-02 | 1988-09-30 | (2-thienyl-methyl)-thiourea derivatives |
| IT8822147A IT1226862B (it) | 1987-10-02 | 1988-09-30 | Derivati della (2 tienil metil) tiourea |
| DD88320334A DD282914A5 (de) | 1987-10-02 | 1988-09-30 | Verfahren zur herstellung von (2-thienyl-methyl)-thioharnstoffderivaten |
| PL1988277629A PL151837B1 (en) | 1987-10-02 | 1988-09-30 | Method of obtaining novel derivatives of (thienyl-2-methyl) thiourea |
| NL8802406A NL8802406A (nl) | 1987-10-02 | 1988-09-30 | (2-thienylmethyl)-thioureumderivaten. |
| BE8801119A BE1003234A4 (fr) | 1987-10-02 | 1988-09-30 | Derives de 2-thienylmethyl thiouree. |
| FR8812802A FR2621315A1 (fr) | 1987-10-02 | 1988-09-30 | Derives de 2-thienylmethyl thiouree, procede pour leur preparation et aliments les contenant |
| PL1988277628A PL151836B1 (en) | 1987-10-02 | 1988-09-30 | Method of obtaining novel derivatives of (thienyl-2-methyl)thiourea |
| DK549788A DK549788A (da) | 1987-10-02 | 1988-09-30 | Thiourinstofderivater |
| PL1988274988A PL151572B1 (en) | 1987-10-02 | 1988-09-30 | Method of obtaining novel derivatives of /thienyl-2-methyl/thiourea |
| ES8802966A ES2012122A6 (es) | 1987-10-02 | 1988-09-30 | Procedimiento de preparacion de derivados de (2-tienilmetil)-tiourea, composiciones y aditivos de piensos y procedimiento y metodo correspondientes. |
| GB8823012A GB2210616B (en) | 1987-10-02 | 1988-09-30 | (2-thienyl-methyl)-thiourea derivatives |
| KR1019880012758A KR890006612A (ko) | 1987-10-02 | 1988-09-30 | (2- 티에닐- 메틸)- 티오우레아 유도체와 그의 제조방법 |
| JP63244723A JPH01156975A (ja) | 1987-10-02 | 1988-09-30 | （２−チエニルメチル）チオ尿素誘導体及びその製造方法、前記化合物を含む体重増大作用を有する飼料添加物、並びに酪農における前記添加物の使用方法 |
| SU884356919A RU1792415C (ru) | 1987-10-02 | 1988-09-30 | Способ получени производных (2-тиенилметил)-тиомочевины |
| DE3833603A DE3833603A1 (de) | 1987-10-02 | 1988-10-03 | (thien-2-yl-methyl)-thioharnstoffderivate, verfahren zur herstellung derselben und diese enthaltende beifuttermittel, futtermittelkonzentrate und futtermittel |
| SU894613899A SU1739847A3 (ru) | 1987-10-02 | 1989-04-18 | Способ получени производных (2-тиенилметил)-тиомочевины |
| SU894613916A SU1709909A3 (ru) | 1987-10-02 | 1989-04-18 | Способ получени производных /2-тиенилметил/-тиомочевины |
| YU00204/90A YU20490A (en) | 1987-10-02 | 1990-02-05 | Process for obtaining new derivatives of (2-thienyl-methyl)-thiourea |
| YU00205/90A YU20590A (en) | 1987-10-02 | 1990-02-05 | Process for obtaining new derivatives of (2-thienyl-methyl)-thiourea |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT48879A HUT48879A (en) | 1989-07-28 |
| HU202516B true HU202516B (en) | 1991-03-28 |
Family
ID=10967957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU874437A HU202516B (en) | 1987-10-02 | 1987-10-02 | Process for producing (2-thenyl)-thiourea derivatives and yield increasing agents comprising such compounds |
Country Status (19)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO20093460A1 (no) * | 2009-12-02 | 2011-06-03 | Ewos Innovation As | Fôrsammensetning til fisk inneholdende en semiokjemisk maskeringsforbindelse samt anvendelse av forbindelsen. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125059C (enrdf_load_stackoverflow) * | 1963-05-31 | |||
| US4267191A (en) * | 1980-05-21 | 1981-05-12 | American Cyanamid Company | Process for enhancing growth promotion in animals |
| US4313885A (en) * | 1980-05-21 | 1982-02-02 | American Cyanamid Company | Furfuryl thiourea compounds |
| JP2581556B2 (ja) * | 1986-05-06 | 1997-02-12 | メレルダウファーマスーティカルズ インコーポレーテッド | 新規なドパミンベ−タヒドロキシラ−ゼ抑制剤 |
| DE3703963A1 (de) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen |
-
1987
- 1987-10-02 HU HU874437A patent/HU202516B/hu not_active IP Right Cessation
-
1988
- 1988-09-29 IL IL87874A patent/IL87874A0/xx unknown
- 1988-09-29 YU YU01821/88A patent/YU182188A/xx unknown
- 1988-09-29 CH CH3625/88A patent/CH676849A5/de not_active IP Right Cessation
- 1988-09-30 NL NL8802406A patent/NL8802406A/nl unknown
- 1988-09-30 GB GB8823012A patent/GB2210616B/en not_active Expired - Lifetime
- 1988-09-30 KR KR1019880012758A patent/KR890006612A/ko not_active Withdrawn
- 1988-09-30 IT IT8822147A patent/IT1226862B/it active
- 1988-09-30 ES ES8802966A patent/ES2012122A6/es not_active Expired - Lifetime
- 1988-09-30 FR FR8812802A patent/FR2621315A1/fr not_active Withdrawn
- 1988-09-30 DK DK549788A patent/DK549788A/da not_active Application Discontinuation
- 1988-09-30 RU SU884356919A patent/RU1792415C/ru active
- 1988-09-30 PL PL1988274988A patent/PL151572B1/pl unknown
- 1988-09-30 JP JP63244723A patent/JPH01156975A/ja active Pending
- 1988-09-30 DD DD88320334A patent/DD282914A5/de not_active IP Right Cessation
- 1988-09-30 PL PL1988277628A patent/PL151836B1/pl unknown
- 1988-09-30 BE BE8801119A patent/BE1003234A4/fr not_active IP Right Cessation
- 1988-09-30 AU AU23329/88A patent/AU607811B2/en not_active Ceased
- 1988-09-30 PL PL1988277629A patent/PL151837B1/pl unknown
- 1988-10-03 DE DE3833603A patent/DE3833603A1/de not_active Withdrawn
-
1989
- 1989-04-18 SU SU894613899A patent/SU1739847A3/ru active
- 1989-04-18 SU SU894613916A patent/SU1709909A3/ru active
-
1990
- 1990-02-05 YU YU00205/90A patent/YU20590A/xx unknown
- 1990-02-05 YU YU00204/90A patent/YU20490A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU607811B2 (en) | 1991-03-14 |
| NL8802406A (nl) | 1989-05-01 |
| YU20590A (en) | 1990-06-30 |
| AU2332988A (en) | 1989-04-06 |
| ES2012122A6 (es) | 1990-03-01 |
| YU20490A (en) | 1990-06-30 |
| DE3833603A1 (de) | 1989-04-13 |
| PL151837B1 (en) | 1990-10-31 |
| SU1739847A3 (ru) | 1992-06-07 |
| IT1226862B (it) | 1991-02-19 |
| PL151836B1 (en) | 1990-10-31 |
| GB8823012D0 (en) | 1988-11-09 |
| BE1003234A4 (fr) | 1992-02-04 |
| PL151572B1 (en) | 1990-09-28 |
| PL277628A1 (en) | 1989-08-21 |
| JPH01156975A (ja) | 1989-06-20 |
| IL87874A0 (en) | 1989-03-31 |
| GB2210616B (en) | 1991-03-27 |
| KR890006612A (ko) | 1989-06-14 |
| YU182188A (en) | 1990-06-30 |
| CH676849A5 (enrdf_load_stackoverflow) | 1991-03-15 |
| DK549788A (da) | 1989-04-03 |
| IT8822147A0 (it) | 1988-09-30 |
| DK549788D0 (da) | 1988-09-30 |
| PL277629A1 (en) | 1989-08-21 |
| HUT48879A (en) | 1989-07-28 |
| SU1709909A3 (ru) | 1992-01-30 |
| FR2621315A1 (fr) | 1989-04-07 |
| PL274988A1 (en) | 1989-06-12 |
| GB2210616A (en) | 1989-06-14 |
| DD282914A5 (de) | 1990-09-26 |
| RU1792415C (ru) | 1993-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |