IE43309B1 - Chloro-substituted benzo /1,3/ dioxins for use in animal husbandry - Google Patents
Chloro-substituted benzo /1,3/ dioxins for use in animal husbandryInfo
- Publication number
- IE43309B1 IE43309B1 IE604/76A IE60476A IE43309B1 IE 43309 B1 IE43309 B1 IE 43309B1 IE 604/76 A IE604/76 A IE 604/76A IE 60476 A IE60476 A IE 60476A IE 43309 B1 IE43309 B1 IE 43309B1
- Authority
- IE
- Ireland
- Prior art keywords
- radical
- dioxin
- benzo
- formula
- compound
- Prior art date
Links
- 150000002013 dioxins Chemical class 0.000 title claims abstract description 46
- 125000005605 benzo group Chemical class 0.000 title claims description 140
- 241001465754 Metazoa Species 0.000 title claims description 16
- -1 2, 2, 2 - trichloroethylidene Chemical group 0.000 claims abstract description 311
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 239000000203 mixture Substances 0.000 claims abstract description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
- 239000007787 solid Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 241000282849 Ruminantia Species 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 9
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000457 gamma-lactone group Chemical group 0.000 claims abstract description 8
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 6
- 239000003651 drinking water Substances 0.000 claims abstract description 6
- 235000020188 drinking water Nutrition 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 239000008188 pellet Substances 0.000 claims abstract description 3
- 150000003254 radicals Chemical class 0.000 claims description 61
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical compound O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 48
- 238000004519 manufacturing process Methods 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 17
- LXOHISCRPIDIIG-UHFFFAOYSA-N 1,4-dioxine-2-carboxylic acid Chemical compound OC(=O)C1=COC=CO1 LXOHISCRPIDIIG-UHFFFAOYSA-N 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 14
- 235000012054 meals Nutrition 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical class C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 claims description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 claims description 7
- 229960002327 chloral hydrate Drugs 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 7
- 230000003000 nontoxic effect Effects 0.000 claims description 7
- 241000283690 Bos taurus Species 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 5
- 244000105624 Arachis hypogaea Species 0.000 claims description 5
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 5
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 240000005979 Hordeum vulgare Species 0.000 claims description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 241000209140 Triticum Species 0.000 claims description 4
- 235000021307 Triticum Nutrition 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical group Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 claims description 4
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 235000013379 molasses Nutrition 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000011573 trace mineral Substances 0.000 claims description 4
- 235000013619 trace mineral Nutrition 0.000 claims description 4
- 239000011782 vitamin Substances 0.000 claims description 4
- 235000013343 vitamin Nutrition 0.000 claims description 4
- 229940088594 vitamin Drugs 0.000 claims description 4
- 229930003231 vitamin Natural products 0.000 claims description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical group O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 3
- 241001474374 Blennius Species 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 241001494479 Pecora Species 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- HNLMSVAIAAHVPD-UHFFFAOYSA-N [2,4-bis(trichloromethyl)-4h-1,3-benzodioxin-6-yl]methyl formate Chemical compound O=COCC1=CC=C2OC(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=C1 HNLMSVAIAAHVPD-UHFFFAOYSA-N 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 210000003746 feather Anatomy 0.000 claims description 3
- 235000013312 flour Nutrition 0.000 claims description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 229940117953 phenylisothiocyanate Drugs 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- UXTFKIJKRJJXNV-UHFFFAOYSA-N 1-$l^{1}-oxidanylethanone Chemical compound CC([O])=O UXTFKIJKRJJXNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- RLBMUSXRBJXWOW-UHFFFAOYSA-N 2-(2,2-dichloro-1-hydroxyethyl)phenol Chemical compound ClC(Cl)C(O)C1=CC=CC=C1O RLBMUSXRBJXWOW-UHFFFAOYSA-N 0.000 claims description 2
- MDSBFGHGCYEPNU-UHFFFAOYSA-N 2-(trichloromethyl)-4h-1,3-benzodioxine Chemical compound C1=CC=C2OC(C(Cl)(Cl)Cl)OCC2=C1 MDSBFGHGCYEPNU-UHFFFAOYSA-N 0.000 claims description 2
- KMMPQFQOBDAVKA-UHFFFAOYSA-N 4-(dichloromethylidene)-2-(trichloromethyl)-1,3-benzodioxin-6-amine Chemical compound O1C(C(Cl)(Cl)Cl)OC(=C(Cl)Cl)C2=CC(N)=CC=C21 KMMPQFQOBDAVKA-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 241000237502 Ostreidae Species 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- WYQIGTBGUPHQIG-UHFFFAOYSA-N [N]=Cc1ccccc1 Chemical group [N]=Cc1ccccc1 WYQIGTBGUPHQIG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- IXWIAFSBWGYQOE-UHFFFAOYSA-M aluminum;magnesium;oxygen(2-);silicon(4+);hydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] IXWIAFSBWGYQOE-UHFFFAOYSA-M 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229940036811 bone meal Drugs 0.000 claims description 2
- 239000002374 bone meal Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 235000005911 diet Nutrition 0.000 claims description 2
- 230000037213 diet Effects 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical group O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000016709 nutrition Nutrition 0.000 claims description 2
- 235000020636 oyster Nutrition 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 2
- 239000008247 solid mixture Substances 0.000 claims description 2
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 2
- NYXFQGHVTKLACF-UHFFFAOYSA-N 2,4-bis(trichloromethyl)-4h-1,3-benzodioxine-6-sulfonamide Chemical compound O1C(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=CC(S(=O)(=O)N)=CC=C21 NYXFQGHVTKLACF-UHFFFAOYSA-N 0.000 claims 1
- JBMFMIXAZCTFGE-UHFFFAOYSA-N 4-(dichloromethylidene)-6-nitro-2-(trichloromethyl)-1,3-benzodioxine Chemical compound O1C(C(Cl)(Cl)Cl)OC(=C(Cl)Cl)C2=CC([N+](=O)[O-])=CC=C21 JBMFMIXAZCTFGE-UHFFFAOYSA-N 0.000 claims 1
- UCZQXJKDCHCTAI-UHFFFAOYSA-N 4h-1,3-dioxine Chemical class C1OCC=CO1 UCZQXJKDCHCTAI-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 239000012265 solid product Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 210000004767 rumen Anatomy 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000001117 sulphuric acid Substances 0.000 description 8
- 235000011149 sulphuric acid Nutrition 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
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- 238000000855 fermentation Methods 0.000 description 7
- 230000004151 fermentation Effects 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 235000019577 caloric intake Nutrition 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010016717 Fistula Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000003890 fistula Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- INEFVLHTEJKMFQ-UHFFFAOYSA-N 3-(2,2-dichloro-1-hydroxyethyl)-4-hydroxybenzoic acid Chemical compound ClC(Cl)C(O)C1=CC(C(O)=O)=CC=C1O INEFVLHTEJKMFQ-UHFFFAOYSA-N 0.000 description 2
- FTPOSTDOUIMEJU-UHFFFAOYSA-N 4-(dichloromethylidene)-n,n-diethyl-2-(trichloromethyl)-1,3-benzodioxine-6-carboxamide Chemical compound O1C(C(Cl)(Cl)Cl)OC(=C(Cl)Cl)C2=CC(C(=O)N(CC)CC)=CC=C21 FTPOSTDOUIMEJU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- KKELBLRPKYNGJG-UHFFFAOYSA-N 1,4-dioxine-2-carbonyl chloride Chemical compound O1C=COC=C1C(=O)Cl KKELBLRPKYNGJG-UHFFFAOYSA-N 0.000 description 1
- OOHZDNBUPJEJDZ-UHFFFAOYSA-N 2,2-dichloro-1-(2-hydroxyphenyl)ethanone Chemical compound OC1=CC=CC=C1C(=O)C(Cl)Cl OOHZDNBUPJEJDZ-UHFFFAOYSA-N 0.000 description 1
- OCRFDWNCDVEBCT-UHFFFAOYSA-N 2,4-bis(trichloromethyl)-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=C1 OCRFDWNCDVEBCT-UHFFFAOYSA-N 0.000 description 1
- HZFGCTHPYZTKEK-UHFFFAOYSA-N 2,4-bis(trichloromethyl)-4h-1,3-benzodioxine-6-carboxylic acid Chemical compound O1C(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=CC(C(=O)O)=CC=C21 HZFGCTHPYZTKEK-UHFFFAOYSA-N 0.000 description 1
- YNKBLWGHWXBPOF-UHFFFAOYSA-N 4-(dichloromethylidene)-2-(trichloromethyl)-1,3-benzodioxine-6-carbohydrazide Chemical compound O1C(C(Cl)(Cl)Cl)OC(=C(Cl)Cl)C2=CC(C(=O)NN)=CC=C21 YNKBLWGHWXBPOF-UHFFFAOYSA-N 0.000 description 1
- WZRNENAPILBIHS-UHFFFAOYSA-N 4-(dichloromethylidene)-2-(trichloromethyl)-1,3-benzodioxine-6-carboxylic acid Chemical compound O1C(C(Cl)(Cl)Cl)OC(=C(Cl)Cl)C2=CC(C(=O)O)=CC=C21 WZRNENAPILBIHS-UHFFFAOYSA-N 0.000 description 1
- NJESAXZANHETJV-UHFFFAOYSA-N 4-methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 1
- QOONEXZXVVSFSB-UHFFFAOYSA-N 5,7-dibromo-2,4-bis(trichloromethyl)-4h-1,3-benzodioxin-6-amine Chemical compound O1C(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=C(Br)C(N)=C(Br)C=C21 QOONEXZXVVSFSB-UHFFFAOYSA-N 0.000 description 1
- KZHOBPMAAOZFRS-UHFFFAOYSA-N 6-methoxy-2,4-bis(trichloromethyl)-4h-1,3-benzodioxine Chemical compound O1C(C(Cl)(Cl)Cl)OC(C(Cl)(Cl)Cl)C2=CC(OC)=CC=C21 KZHOBPMAAOZFRS-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VKMTZVKIFRDYMV-UHFFFAOYSA-N ClC(Cl)=[C] Chemical compound ClC(Cl)=[C] VKMTZVKIFRDYMV-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000918728 Monotes Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- FCCCRBDJBTVFSJ-UHFFFAOYSA-N butanehydrazide Chemical compound CCCC(=O)NN FCCCRBDJBTVFSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000011868 grain product Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- 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
-
- 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
- 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
- A23K20/126—Lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/807—Poultry or ruminant feed
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Fodder In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Feed For Specific Animals (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14316/75A GB1502116A (en) | 1975-04-08 | 1975-04-08 | Chloro-substituted benzo(1,3)dioxins for use in animal husbandry |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43309L IE43309L (en) | 1976-10-08 |
| IE43309B1 true IE43309B1 (en) | 1981-01-28 |
Family
ID=10038995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE604/76A IE43309B1 (en) | 1975-04-08 | 1976-03-22 | Chloro-substituted benzo /1,3/ dioxins for use in animal husbandry |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4232032A (enExample) |
| JP (1) | JPS51127086A (enExample) |
| AR (1) | AR212166A1 (enExample) |
| AU (1) | AU503851B2 (enExample) |
| BE (1) | BE840487A (enExample) |
| CA (1) | CA1071008A (enExample) |
| DE (1) | DE2615376A1 (enExample) |
| DK (1) | DK140676A (enExample) |
| ES (1) | ES446827A1 (enExample) |
| FR (1) | FR2306640A1 (enExample) |
| GB (1) | GB1502116A (enExample) |
| IE (1) | IE43309B1 (enExample) |
| NL (1) | NL7603632A (enExample) |
| ZA (1) | ZA761698B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543357A (en) * | 1983-12-27 | 1985-09-24 | The Dow Chemical Company | 3-Trichloromethyl-5-substituted-1,2,4-thiadiazoles as ruminant animal growth promoters |
| US5985907A (en) * | 1998-08-12 | 1999-11-16 | Health Research, Inc. | Method for inhibiting growth of methanogens |
| CN1737001A (zh) * | 2004-08-17 | 2006-02-22 | 兰克赛斯德国有限公司 | 氟化1,3－苯并二噁烷的制备 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2730451A (en) * | 1952-04-07 | 1956-01-10 | Gen Mills Inc | Drying oil product and method of producing |
| US2789985A (en) * | 1955-03-28 | 1957-04-23 | Gen Mills Inc | Substituted benzodioxanes |
-
1975
- 1975-04-08 GB GB14316/75A patent/GB1502116A/en not_active Expired
-
1976
- 1976-03-19 ZA ZA761698A patent/ZA761698B/xx unknown
- 1976-03-22 IE IE604/76A patent/IE43309B1/en unknown
- 1976-03-23 US US05/669,498 patent/US4232032A/en not_active Expired - Lifetime
- 1976-03-25 AU AU12352/76A patent/AU503851B2/en not_active Expired
- 1976-03-26 CA CA249,120A patent/CA1071008A/en not_active Expired
- 1976-03-29 DK DK140676A patent/DK140676A/da unknown
- 1976-04-07 BE BE165933A patent/BE840487A/xx not_active IP Right Cessation
- 1976-04-07 AR AR262810A patent/AR212166A1/es active
- 1976-04-07 FR FR7610155A patent/FR2306640A1/fr active Granted
- 1976-04-07 NL NL7603632A patent/NL7603632A/xx not_active Application Discontinuation
- 1976-04-08 DE DE19762615376 patent/DE2615376A1/de not_active Withdrawn
- 1976-04-08 JP JP51039787A patent/JPS51127086A/ja active Pending
- 1976-04-08 ES ES446827A patent/ES446827A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2615376A1 (de) | 1976-11-04 |
| AR212166A1 (es) | 1978-05-31 |
| BE840487A (fr) | 1976-10-07 |
| ZA761698B (en) | 1977-03-30 |
| CA1071008A (en) | 1980-02-05 |
| ES446827A1 (es) | 1978-07-01 |
| GB1502116A (en) | 1978-02-22 |
| AU503851B2 (en) | 1979-09-20 |
| NL7603632A (nl) | 1976-10-12 |
| DK140676A (da) | 1976-10-09 |
| FR2306640B1 (enExample) | 1980-10-31 |
| IE43309L (en) | 1976-10-08 |
| FR2306640A1 (fr) | 1976-11-05 |
| US4232032A (en) | 1980-11-04 |
| JPS51127086A (en) | 1976-11-05 |
| AU1235276A (en) | 1977-09-29 |
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