DE1642305C - - Google Patents

Info

Publication number

DE1642305C

DE1642305C DE19671642305 DE1642305A DE1642305C DE 1642305 C DE1642305 C DE 1642305C DE 19671642305 DE19671642305 DE 19671642305 DE 1642305 A DE1642305 A DE 1642305A DE 1642305 C DE1642305 C DE 1642305C

Authority

DE

Germany

Prior art keywords

destomycin

days

eggs

water

feed

Prior art date

1966-07-08

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

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• GRRNUXAQVGOGFE-UHFFFAOYSA-N Hygromycin-B Natural products OC1C(NC)CC(N)C(O)C1OC1C2OC3(C(C(O)C(O)C(C(N)CO)O3)O)OC2C(O)C(CO)O1 GRRNUXAQVGOGFE-UHFFFAOYSA-N 0.000 claims description 24
• GRRNUXAQVGOGFE-SVNOMHMPSA-N (3'r,3as,4s,4's,5'r,6r,6'r,7s,7as)-4-[(1s,2r,3s,5r,6s)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1s)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol Chemical compound O[C@H]1[C@H](NC)C[C@H](N)[C@@H](O)[C@@H]1O[C@H]1[C@H]2OC3([C@@H]([C@@H](O)[C@@H](O)[C@@H]([C@@H](N)CO)O3)O)O[C@H]2[C@@H](O)[C@@H](CO)O1 GRRNUXAQVGOGFE-SVNOMHMPSA-N 0.000 claims description 23
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 235000013601 eggs Nutrition 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 241000244186 Ascaris Species 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 244000045947 parasite Species 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 241000282887 Suidae Species 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 239000004480 active ingredient Substances 0.000 description 4
• 230000029142 excretion Effects 0.000 description 4
• YQYJSBFKSSDGFO-FWAVGLHBSA-N hygromycin A Chemical compound O[C@H]1[C@H](O)[C@H](C(=O)C)O[C@@H]1Oc1ccc(\C=C(/C)C(=O)N[C@@H]2[C@@H]([C@H]3OCO[C@H]3[C@@H](O)[C@@H]2O)O)cc1O YQYJSBFKSSDGFO-FWAVGLHBSA-N 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 241000334075 Streptomyces rimofaciens Species 0.000 description 3
• 230000000507 anthelmentic effect Effects 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 235000013305 food Nutrition 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 238000007127 saponification reaction Methods 0.000 description 3
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
• -1 5 - methylenedioxycyclohexyl Chemical group 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• 241000204725 Ascaridia galli Species 0.000 description 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 241001465754 Metazoa Species 0.000 description 2
• 241000960389 Trichuris suis Species 0.000 description 2
• 238000010521 absorption reaction Methods 0.000 description 2
• 239000003242 anti bacterial agent Substances 0.000 description 2
• 239000003096 antiparasitic agent Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 239000003729 cation exchange resin Substances 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 230000007423 decrease Effects 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 239000003456 ion exchange resin Substances 0.000 description 2
• 229920003303 ion-exchange polymer Polymers 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 235000015097 nutrients Nutrition 0.000 description 2
• 230000003287 optical effect Effects 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 239000000047 product Substances 0.000 description 2
• 235000002639 sodium chloride Nutrition 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000002904 solvent Substances 0.000 description 2
• NIDNOXCRFUCAKQ-UMRXKNAASA-N (1s,2r,3s,4r)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1[C@H]2C=C[C@@H]1[C@H](C(=O)O)[C@@H]2C(O)=O NIDNOXCRFUCAKQ-UMRXKNAASA-N 0.000 description 1
• BBBFYZOJHSYQMW-LGDQNDJISA-N (2s)-2,4-diamino-4-oxobutanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC(=O)[C@@H](N)CC(N)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O BBBFYZOJHSYQMW-LGDQNDJISA-N 0.000 description 1
• GRRNUXAQVGOGFE-KPBUCVLVSA-N (3'r,3as,4s,4'r,5'r,6r,6'r,7s,7as)-4-[(1r,2s,3r,5s,6r)-3-amino-2,6-dihydroxy-5-(methylamino)cyclohexyl]oxy-6'-[(1s)-1-amino-2-hydroxyethyl]-6-(hydroxymethyl)spiro[4,6,7,7a-tetrahydro-3ah-[1,3]dioxolo[4,5-c]pyran-2,2'-oxane]-3',4',5',7-tetrol Chemical compound O[C@@H]1[C@@H](NC)C[C@@H](N)[C@H](O)[C@H]1O[C@H]1[C@H]2OC3([C@@H]([C@H](O)[C@@H](O)[C@@H]([C@@H](N)CO)O3)O)O[C@H]2[C@@H](O)[C@@H](CO)O1 GRRNUXAQVGOGFE-KPBUCVLVSA-N 0.000 description 1
• IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
• PKDBCJSWQUOKDO-UHFFFAOYSA-M 2,3,5-triphenyltetrazolium chloride Chemical compound [Cl-].C1=CC=CC=C1C(N=[N+]1C=2C=CC=CC=2)=NN1C1=CC=CC=C1 PKDBCJSWQUOKDO-UHFFFAOYSA-M 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• FIHZWZBEAXASKA-UHFFFAOYSA-N Anthron Natural products COc1cc2Cc3cc(C)cc(O)c3C(=O)c2c(O)c1C=CC(C)C FIHZWZBEAXASKA-UHFFFAOYSA-N 0.000 description 1
• 241000242722 Cestoda Species 0.000 description 1
• 125000003474 D-talosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
• 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
• 241000287828 Gallus gallus Species 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• UVMKZRHHUOWSAC-UHFFFAOYSA-N Hyosamine Natural products CNC1CC(N)C(O)C(O)C1O UVMKZRHHUOWSAC-UHFFFAOYSA-N 0.000 description 1
• 239000001888 Peptone Substances 0.000 description 1
• 108010080698 Peptones Proteins 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 241001032716 Raillietina cesticillus Species 0.000 description 1
• 241000060037 Raillietina echinobothrida Species 0.000 description 1
• 235000019764 Soybean Meal Nutrition 0.000 description 1
• PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
• 150000008065 acid anhydrides Chemical class 0.000 description 1
• 239000008272 agar Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 229940024606 amino acid Drugs 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 238000005349 anion exchange Methods 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 238000012474 bioautography Methods 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 229940023913 cation exchange resins Drugs 0.000 description 1
• 229920001429 chelating resin Polymers 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• APEJMQOBVMLION-UHFFFAOYSA-N cinnamic acid amide Natural products NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 1
• 239000013065 commercial product Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 238000000921 elemental analysis Methods 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• 210000003608 fece Anatomy 0.000 description 1
• 238000000855 fermentation Methods 0.000 description 1
• 230000004151 fermentation Effects 0.000 description 1
• 239000004459 forage Substances 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 229910052739 hydrogen Inorganic materials 0.000 description 1
• GRRNUXAQVGOGFE-NZSRVPFOSA-N hygromycin B Chemical compound O[C@@H]1[C@@H](NC)C[C@@H](N)[C@H](O)[C@H]1O[C@H]1[C@H]2O[C@@]3([C@@H]([C@@H](O)[C@@H](O)[C@@H](C(N)CO)O3)O)O[C@H]2[C@@H](O)[C@@H](CO)O1 GRRNUXAQVGOGFE-NZSRVPFOSA-N 0.000 description 1
• 229940097277 hygromycin b Drugs 0.000 description 1
• 238000011081 inoculation Methods 0.000 description 1
• 229960000367 inositol Drugs 0.000 description 1
• 238000011835 investigation Methods 0.000 description 1
• 235000013372 meat Nutrition 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 229910052760 oxygen Inorganic materials 0.000 description 1
• 235000019319 peptone Nutrition 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
• OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
• 229920006395 saturated elastomer Polymers 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 210000000813 small intestine Anatomy 0.000 description 1
• 239000002689 soil Substances 0.000 description 1
• 238000001179 sorption measurement Methods 0.000 description 1
• 239000004455 soybean meal Substances 0.000 description 1
• 235000012424 soybean oil Nutrition 0.000 description 1
• 239000003549 soybean oil Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 230000004584 weight gain Effects 0.000 description 1
• 235000019786 weight gain Nutrition 0.000 description 1