CH593952A5 - 4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents - Google Patents

4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents

Info

Publication number: CH593952A5
Authority: CH; Switzerland
Prior art keywords: benzotriazine; alkyl; oxide; imino; acid
Prior art date: 1974-03-15

Application number

CH363274A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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

1974-03-15

Filing date

1974-03-15

Publication date

1977-12-30

1974-03-15 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-03-15 Priority to CH363274A priority Critical patent/CH593952A5/de

1975-02-13 Priority to SE7501624A priority patent/SE7501624L/xx

1975-03-05 Priority to SU752111303A priority patent/SU707503A3/ru

1975-03-06 Priority to GB9439/75A priority patent/GB1498499A/en

1975-03-11 Priority to US05/557,441 priority patent/US3985745A/en

1975-03-12 Priority to DE19752510822 priority patent/DE2510822A1/de

1975-03-13 Priority to CA222,031A priority patent/CA1049518A/fr

1975-03-13 Priority to IL46821A priority patent/IL46821A/xx

1975-03-13 Priority to NL7503014A priority patent/NL7503014A/xx

1975-03-14 Priority to IE561/75A priority patent/IE40862B1/xx

1975-03-14 Priority to AT197875A priority patent/AT341532B/de

1975-03-14 Priority to FR7508014A priority patent/FR2263777B1/fr

1975-03-14 Priority to ZA00751611A priority patent/ZA751611B/xx

1975-03-14 Priority to BE154375A priority patent/BE826731A/fr

1975-03-14 Priority to DK104575A priority patent/DK104575A/da

1975-03-14 Priority to AU79079/75A priority patent/AU498272B2/en

1975-03-15 Priority to JP50031739A priority patent/JPS50126834A/ja

1976-04-27 Priority to DK189076A priority patent/DK189076A/da

1977-02-21 Priority to AT114177A priority patent/AT350892B/de

1977-12-30 Publication of CH593952A5 publication Critical patent/CH593952A5/de

Links

ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical class C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 title claims description 3
-1 phenylsulphonyl Chemical group 0.000 claims abstract description 45
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
239000002904 solvent Substances 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
BBRWGJRKAHEZBG-UHFFFAOYSA-N 1-oxido-1,2,4-benzotriazin-1-ium-3-amine Chemical class C1=CC=CC2=[N+]([O-])NC(=N)N=C21 BBRWGJRKAHEZBG-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000012749 thinning agent Substances 0.000 claims 1
241001465754 Metazoa Species 0.000 abstract description 8
241000894006 Bacteria Species 0.000 abstract description 5
241000233866 Fungi Species 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 5
244000144977 poultry Species 0.000 abstract description 5
241000588724 Escherichia coli Species 0.000 abstract description 3
239000004599 antimicrobial Substances 0.000 abstract description 3
LAYRNPDGAGLPDK-UHFFFAOYSA-N (3-imino-1-oxido-1,2,4-benzotriazin-1-ium-4-yl) acetate Chemical compound C1=CC=C2[N+]([O-])=NC(=N)N(OC(=O)C)C2=C1 LAYRNPDGAGLPDK-UHFFFAOYSA-N 0.000 abstract description 2
241000283690 Bos taurus Species 0.000 abstract 1
241001494479 Pecora Species 0.000 abstract 1
241000282887 Suidae Species 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 25
239000004480 active ingredient Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
244000052616 bacterial pathogen Species 0.000 description 9
235000019441 ethanol Nutrition 0.000 description 9
239000000203 mixture Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000013543 active substance Substances 0.000 description 7
230000000845 anti-microbial effect Effects 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000000243 solution Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
239000000047 product Substances 0.000 description 6
BNZPFJBUHRBLNB-UHFFFAOYSA-N 1-oxido-1,2,4-benzotriazin-1-ium Chemical class C1=CC=C2[N+]([O-])=NC=NC2=C1 BNZPFJBUHRBLNB-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000012459 cleaning agent Substances 0.000 description 5
239000003599 detergent Substances 0.000 description 5
239000000123 paper Substances 0.000 description 5
239000004033 plastic Substances 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
239000011630 iodine Substances 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000645 desinfectant Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000001802 infusion Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000003641 microbiacidal effect Effects 0.000 description 3
244000000010 microbial pathogen Species 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
230000001717 pathogenic effect Effects 0.000 description 3
235000013594 poultry meat Nutrition 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000004094 surface-active agent Substances 0.000 description 3
239000002023 wood Substances 0.000 description 3
PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 2
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
DSPXASHHKFVPCL-UHFFFAOYSA-N 1-isocyanocyclohexene Chemical compound [C-]#[N+]C1=CCCCC1 DSPXASHHKFVPCL-UHFFFAOYSA-N 0.000 description 2
SMKVMKIYICQVAE-UHFFFAOYSA-N 1-oxidotriazin-1-ium Chemical compound [O-][N+]1=CC=CN=N1 SMKVMKIYICQVAE-UHFFFAOYSA-N 0.000 description 2
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
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CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
239000005725 8-Hydroxyquinoline Substances 0.000 description 2
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241000193830 Bacillus <bacterium> Species 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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241000287828 Gallus gallus Species 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
210000004712 air sac Anatomy 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
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239000003085 diluting agent Substances 0.000 description 2
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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238000002474 experimental method Methods 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 2
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MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
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125000001424 substituent group Chemical group 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 1
FVJIUQSKXOYFKG-UHFFFAOYSA-N (3,4-dichlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C(Cl)=C1 FVJIUQSKXOYFKG-UHFFFAOYSA-N 0.000 description 1
YWMSPYAVKFABPD-UHFFFAOYSA-M (3,4-dichlorophenyl)methyl-dodecyl-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=C(Cl)C(Cl)=C1 YWMSPYAVKFABPD-UHFFFAOYSA-M 0.000 description 1
MVCAHORKWPKPHM-UHFFFAOYSA-N (3-imino-1-oxido-1,2,4-benzotriazin-1-ium-4-yl) 2-chloroacetate Chemical compound C1=CC=C2[N+]([O-])=NC(=N)N(OC(=O)CCl)C2=C1 MVCAHORKWPKPHM-UHFFFAOYSA-N 0.000 description 1
OYPQIZPPDDOBKF-UHFFFAOYSA-N (3-imino-1-oxido-1,2,4-benzotriazin-1-ium-4-yl) benzoate Chemical compound C12=CC=CC=C2[N+]([O-])=NC(=N)N1OC(=O)C1=CC=CC=C1 OYPQIZPPDDOBKF-UHFFFAOYSA-N 0.000 description 1
LZTXNPOEOROOMW-UHFFFAOYSA-N (3-imino-1-oxido-1,2,4-benzotriazin-1-ium-4-yl) dodecanoate Chemical compound C1=CC=C2[N+]([O-])=NC(=N)N(OC(=O)CCCCCCCCCCC)C2=C1 LZTXNPOEOROOMW-UHFFFAOYSA-N 0.000 description 1
DWOXDKLOODTPHP-UHFFFAOYSA-N (3-imino-1-oxido-7-phenoxy-1,2,4-benzotriazin-1-ium-4-yl) acetate Chemical compound C1=C2[N+]([O-])=NC(=N)N(OC(=O)C)C2=CC=C1OC1=CC=CC=C1 DWOXDKLOODTPHP-UHFFFAOYSA-N 0.000 description 1
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239000004753 textile Substances 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
SRTDKHGZQCTGBY-RVDKCFQWSA-N thiopeptin Chemical compound N1C2C(N=3)=CSC=3C(C(C)OC(=O)C=3N=C4C(O)C(NC(C(C)C)C(=O)NC(C)C(=O)NC(=C)C(=O)NC(C)C(=O)N5)C=CC4=C(C(C)O)C=3)NC(=S)C(N=3)=CSC=3C(C(C)(O)C(C)O)NC(=O)C(N=3)CSC=3C(=C/C)\NC(=O)C(C(C)O)NC(=O)C(N=3)=CSC=3C25CCC1C1=NC(C(N)=O)=CS1 SRTDKHGZQCTGBY-RVDKCFQWSA-N 0.000 description 1
108010030742 thiopeptin Proteins 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
229960000790 thymol Drugs 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
ZSMRBQSZBQBLKB-UHFFFAOYSA-M tributylstannyl 2-hydroxybenzoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=CC=C1O ZSMRBQSZBQBLKB-UHFFFAOYSA-M 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229940055035 trichophyton verrucosum Drugs 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
235000019375 tylosin Nutrition 0.000 description 1
229960004059 tylosin Drugs 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940075466 undecylenate Drugs 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
210000002229 urogenital system Anatomy 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Polymers & Plastics (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH363274A 1974-03-15 1974-03-15 4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents CH593952A5 (en)

Priority Applications (19)

Application Number	Priority Date	Filing Date	Title
CH363274A CH593952A5 (en)	1974-03-15	1974-03-15	4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents
SE7501624A SE7501624L (fr)	1974-03-15	1975-02-13
SU752111303A SU707503A3 (ru)	1974-03-15	1975-03-05	Кормова добавка дл домашней птицы
GB9439/75A GB1498499A (en)	1974-03-15	1975-03-06	Benzotriazines
US05/557,441 US3985745A (en)	1974-03-15	1975-03-11	3-Imino-1,2,4-benzotriazine-1-oxides
DE19752510822 DE2510822A1 (de)	1974-03-15	1975-03-12	3-imino-1,2,4-benzotriazin-1- oxide
CA222,031A CA1049518A (fr)	1974-03-15	1975-03-13	Oxydes d'imino-3 benzotriazine-1,2,4
IL46821A IL46821A (en)	1974-03-15	1975-03-13	4-acyloxy-3-imino-1,2,4-benzotrianzin-1-oxides, their production and their use for the control of microorganisms
NL7503014A NL7503014A (nl)	1974-03-15	1975-03-13	Werkwijze voor het bereiden van 1,2,4-benzotri- azineoxyden, werkwijze voor het bereiden van preparaten met microbicide en/of groei bevorde- rende werking alsmede de aldus bereide gevormde preparaten.
IE561/75A IE40862B1 (en)	1974-03-15	1975-03-14	Benzotriazines
AT197875A AT341532B (de)	1974-03-15	1975-03-14	Verfahren zur herstellung von neuen 3-amino-1,2,4-benztriazin-1-oxid-derivaten
FR7508014A FR2263777B1 (fr)	1974-03-15	1975-03-14
ZA00751611A ZA751611B (en)	1974-03-15	1975-03-14	New heterocycles
BE154375A BE826731A (fr)	1974-03-15	1975-03-14	Composes heterocycliques azotes ayant une activite antimicrobienne
DK104575A DK104575A (fr)	1974-03-15	1975-03-14
AU79079/75A AU498272B2 (en)	1974-03-15	1975-03-14	Benzotriazine derivatives
JP50031739A JPS50126834A (fr)	1974-03-15	1975-03-15
DK189076A DK189076A (da)	1974-03-15	1976-04-27	Tilskudsfodermiddel
AT114177A AT350892B (de)	1974-03-15	1977-02-21	Futterzusatzmittel

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH363274A CH593952A5 (en)	1974-03-15	1974-03-15	4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents

Publications (1)

Publication Number	Publication Date
CH593952A5 true CH593952A5 (en)	1977-12-30

Family

ID=4260145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH363274A CH593952A5 (en)	1974-03-15	1974-03-15	4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents

Country Status (5)

Country	Link
AT (2)	AT341532B (fr)
BE (1)	BE826731A (fr)
CH (1)	CH593952A5 (fr)
SU (1)	SU707503A3 (fr)
ZA (1)	ZA751611B (fr)

1974
- 1974-03-15 CH CH363274A patent/CH593952A5/de not_active IP Right Cessation
1975
- 1975-03-05 SU SU752111303A patent/SU707503A3/ru active
- 1975-03-14 AT AT197875A patent/AT341532B/de not_active IP Right Cessation
- 1975-03-14 ZA ZA00751611A patent/ZA751611B/xx unknown
- 1975-03-14 BE BE154375A patent/BE826731A/fr unknown
1977
- 1977-02-21 AT AT114177A patent/AT350892B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA114177A (de)	1978-11-15
ATA197875A (de)	1977-06-15
ZA751611B (en)	1976-02-25
BE826731A (fr)	1975-09-15
SU707503A3 (ru)	1979-12-30
AT341532B (de)	1978-02-10
AT350892B (de)	1979-06-25

Legal Events

Date	Code	Title	Description
1980-11-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
US4160833A (en)	1979-07-10	1,2,4-Benzotriazine-1,4-di-N-oxide derivatives
DE2849856A1 (de)	1979-05-23	Neue 3-hydroxydiphenylaether
DE2449477A1 (de)	1975-04-30	Neue o-benzylphenole
DE2441601C2 (fr)	1988-11-10
EP0008061B1 (fr)	1981-07-29	Esters phénoliques halogénés, compositions antimicrobiennes les contenant et leur utilisation
US3956402A (en)	1976-05-11	Substituted bis-hydroxyphenyl pentanes
EP0146064A2 (fr)	1985-06-26	1,1-Diphényl-2-triazolyl-2-alkyléthanes, leur préparation et leur emploi comme biocides
CH593952A5 (en)	1977-12-30	4-Acyloxy-3-imino-1,2,4-benzotriazine 1-oxide derivs - prepd by reacting 3-amino-1,2,4-benzotriazine 1,4-dioxides with acylating agents
DE2242187A1 (de)	1973-03-08	Heterocyclische verbindungen
US3991124A (en)	1976-11-09	Alkylphenols
DE2342917A1 (de)	1974-03-14	Alkylphenole
DE2913728A1 (de)	1980-10-16	2-sulfonyl-chinoxaline, verfahren zu ihrer herstellung sowie ihre verwendung als mikrobizide
EP0016391B1 (fr)	1983-03-30	3-Sulfonyl-benzo-1,2,4-triazines et -benzo-1,2,4-triazine 1-oxydes, procédé pour leur préparation et médicaments les contenant ainsi que des compositions antimicrobiennes pour la protection de matériaux
DE2438853A1 (de)	1975-02-20	Mittel zur bekaempfung von schaedlichen mikroorganismen
DE2510822A1 (de)	1975-09-18	3-imino-1,2,4-benzotriazin-1- oxide
CH591459A5 (en)	1977-09-15	1,2,4,-benztriazine-1,4-di-N-oxide derivs. - used in veterinary medicine against pathogenic micro-organisms or to promote growth
EP0031795A1 (fr)	1981-07-08	Hydroxyphénylcétones
CH617430A5 (en)	1980-05-30	Process for the preparation of novel 1,2,4-benzotriazine derivatives
CH549344A (de)	1974-05-31	Handelsfaehiges mittel zur bekaempfung von schaedlichen mikroorganismen.
CH576459A5 (en)	1976-06-15	1,2,4,-benztriazine-1,4-di-N-oxide derivs. - used in veterinary medicine against pathogenic micro-organisms or to promote growth
CH591458A5 (en)	1977-09-15	1,2,4,-benztriazine-1,4-di-N-oxide derivs. - used in veterinary medicine against pathogenic micro-organisms or to promote growth
DE2342147A1 (de)	1974-03-14	Bisphenole
DE2436653A1 (de)	1975-02-20	1-chlor-acrylsaeureamid-derivate
AT333289B (de)	1976-11-10	Verfahren zur herstellung neuer 1,2,4-benztriazin-1,4-di-n-oxidderivate
DE2242185A1 (de)	1973-03-15	Heterocyclische verbindungen