DE2026452C3 - 1 -(5-NitrofuryI)-2-(2-cyclohexenoazolyl)-äthylenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Tierfutterkonservierung - Google Patents
1 -(5-NitrofuryI)-2-(2-cyclohexenoazolyl)-äthylenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur TierfutterkonservierungInfo
- Publication number
- DE2026452C3 DE2026452C3 DE2026452A DE2026452A DE2026452C3 DE 2026452 C3 DE2026452 C3 DE 2026452C3 DE 2026452 A DE2026452 A DE 2026452A DE 2026452 A DE2026452 A DE 2026452A DE 2026452 C3 DE2026452 C3 DE 2026452C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- preparation
- animal feed
- nitrofuryl
- ethylene compounds
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 241001465754 Metazoa Species 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims 2
- -1 5-Nitrofuryl Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- DQMSQXZUGHBBDL-UHFFFAOYSA-N 2-methyl-4,5,6,7-tetrahydro-1,3-benzothiazole Chemical compound C1CCCC2=C1N=C(C)S2 DQMSQXZUGHBBDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 108060003951 Immunoglobulin Proteins 0.000 description 6
- 102000018358 immunoglobulin Human genes 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 4
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 235000013580 sausages Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 231100001225 mammalian toxicity Toxicity 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004334 sorbic acid Substances 0.000 description 3
- 235000010199 sorbic acid Nutrition 0.000 description 3
- 229940075582 sorbic acid Drugs 0.000 description 3
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 2
- VDSJNRWZBWZVOG-UHFFFAOYSA-N 4-methyl-2-[2-(5-nitrofuran-2-yl)ethenyl]-1,3-thiazole Chemical compound CC1=CSC(C=CC=2OC(=CC=2)[N+]([O-])=O)=N1 VDSJNRWZBWZVOG-UHFFFAOYSA-N 0.000 description 2
- DIZOXKBSTCBBQB-UHFFFAOYSA-N 5-methyl-2-[2-(5-nitrofuran-2-yl)ethenyl]-1,3-oxazole Chemical compound [N+](=O)([O-])C1=CC=C(O1)C=CC=1OC(=CN1)C DIZOXKBSTCBBQB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004153 Potassium bromate Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229920001986 Vinylidene chloride-vinyl chloride copolymer Polymers 0.000 description 2
- 210000001557 animal structure Anatomy 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 229940064004 antiseptic throat preparations Drugs 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229940094037 potassium bromate Drugs 0.000 description 2
- 235000019396 potassium bromate Nutrition 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000194106 Bacillus mycoides Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 108010073771 Soybean Proteins Proteins 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000021336 beef liver Nutrition 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910001448 ferrous ion Inorganic materials 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000020993 ground meat Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 235000019690 meat sausages Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- IAIWVQXQOWNYOU-UHFFFAOYSA-N nitrofurazone Chemical compound NC(=O)NN=CC1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 201000005404 rubella Diseases 0.000 description 1
- 235000019710 soybean protein Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4233269 | 1969-05-30 | ||
| JP4233169 | 1969-05-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2026452A1 DE2026452A1 (de) | 1970-12-03 |
| DE2026452B2 DE2026452B2 (de) | 1979-01-18 |
| DE2026452C3 true DE2026452C3 (de) | 1979-09-20 |
Family
ID=26381985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2026452A Expired DE2026452C3 (de) | 1969-05-30 | 1970-05-29 | 1 -(5-NitrofuryI)-2-(2-cyclohexenoazolyl)-äthylenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zur Tierfutterkonservierung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3721667A (https=) |
| CH (1) | CH538502A (https=) |
| DE (1) | DE2026452C3 (https=) |
| FR (1) | FR2051567B1 (https=) |
| GB (1) | GB1257748A (https=) |
| NL (1) | NL7007810A (https=) |
-
1970
- 1970-05-26 US US00040733A patent/US3721667A/en not_active Expired - Lifetime
- 1970-05-29 DE DE2026452A patent/DE2026452C3/de not_active Expired
- 1970-05-29 FR FR7019868A patent/FR2051567B1/fr not_active Expired
- 1970-05-29 NL NL7007810A patent/NL7007810A/xx unknown
- 1970-06-01 GB GB1257748D patent/GB1257748A/en not_active Expired
- 1970-06-01 CH CH815770A patent/CH538502A/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2026452B2 (de) | 1979-01-18 |
| GB1257748A (https=) | 1971-12-22 |
| US3721667A (en) | 1973-03-20 |
| NL7007810A (https=) | 1970-12-02 |
| FR2051567A1 (https=) | 1971-04-09 |
| CH538502A (de) | 1973-06-30 |
| FR2051567B1 (https=) | 1974-08-30 |
| DE2026452A1 (de) | 1970-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |