CA2168357C - Oxathiazines antibacteriennes et antiparasites et leurs oxydes - Google Patents
Oxathiazines antibacteriennes et antiparasites et leurs oxydes Download PDFInfo
- Publication number
- CA2168357C CA2168357C CA002168357A CA2168357A CA2168357C CA 2168357 C CA2168357 C CA 2168357C CA 002168357 A CA002168357 A CA 002168357A CA 2168357 A CA2168357 A CA 2168357A CA 2168357 C CA2168357 C CA 2168357C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- phenyl
- compound
- thienyl
- antifouling
- 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 - Fee Related
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 12
- 230000003373 anti-fouling effect Effects 0.000 title claims description 18
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical class O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 title description 6
- -1 tetrahydropyranyloxy, phenoxy Chemical group 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 11
- 125000002541 furyl group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 229910052717 sulfur Chemical group 0.000 claims abstract description 4
- 239000011593 sulfur Chemical group 0.000 claims abstract description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 32
- 241000894006 Bacteria Species 0.000 claims description 18
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- MTGXUZCZZQPRHK-UHFFFAOYSA-N 3-thiophen-2-yl-5,6-dihydro-1,4,2-oxathiazine Chemical compound O1CCSC(C=2SC=CC=2)=N1 MTGXUZCZZQPRHK-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
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- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
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- 241000195493 Cryptophyta Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
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- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 3
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- 230000000704 physical effect Effects 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- YBBJKCMMCRQZMA-UHFFFAOYSA-N pyrithione Chemical compound ON1C=CC=CC1=S YBBJKCMMCRQZMA-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- JUEAPPHORMOWPK-UHFFFAOYSA-M tributylstannyl benzoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)C1=CC=CC=C1 JUEAPPHORMOWPK-UHFFFAOYSA-M 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- LHHPEAQVCCPLBC-UHFFFAOYSA-N tributyltin;hydrate Chemical compound O.CCCC[Sn](CCCC)CCCC LHHPEAQVCCPLBC-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 229940099259 vaseline Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Utilisation comme agents antibactériens, antilevures, antifongiques, algicides, anticrustacés, molluscicides et agents antipourrissement généraux, de 3-aryl-5,6-dihydro-1,4,2-oxathiazines et de leurs oxydes selon la formule (I), dans laquelle n est 0, 1 ou 2; R<2> est l'hydrogène, un alcoyle C1-4 ou un benzoyle; et R représente (a) du phényle; du phényle avec substitution par 1 à 3 substituants sélectionnés indépendamment parmi hydroxyle, halo, alcoyle C1-12, cycloalcoyle C5-6, trihalométhyle, phényle, alcoxy C1-5, alkylthio C1-5, tétrahydropropyranyloxy, phénoxy, alkylcarbonyle C1-4, phénylcarbonyle, alkylsulfinyle C1-4, alkylsulfonyle C1-4, carboxy ou son sel de métal alcalin, alkyloxycarbonyle C1-4, alkylaminocarbonyle C1-4, phénylaminocarbonyle, tolylaminocarbonyle, morpholinocarbonyle, amino, nitro, cyano, dioxolanyle ou alkyloxyiminométhyle C1-4; naphtyle; pyridinyle; thiényle, de préférence lorsque n n'est pas 2; furanyle; ou thiényle ou furanyle avec substitution par un à trois substituants sélectionnés indépendamment parmi alcoyle C1-4, alkyloxy C1-4, alkylthio C1-4, halo, cyano, formyle, acétyle, benzoyle, nitro, alkyloxycarbonyle C1-4, phényle, phénylaminocarbonyle et alkyloxyiminométhyle C1-4; ou R représente un radical de la formule (b), dans laquelle X est l'oxygène ou le soufre, Y est l'azote, CH ou C(alkyloxy C1-4); et R'' est l'hydrogène ou un alcoyle C1-4. L'invention concerne également des compositions contenant ces agents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002466954A CA2466954C (fr) | 1993-08-24 | 1994-08-24 | Oxathiazines antisallissures et antibacterien et leurs oxydes entrant dans les compositions de revetements |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11135293A | 1993-08-24 | 1993-08-24 | |
| US111,352 | 1993-08-24 | ||
| PCT/EP1994/002784 WO1995005739A1 (fr) | 1993-08-24 | 1994-08-24 | Oxathiazines et oxydes de celles-ci, utilises comme agents antibacteriens et antipourrissement |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002466954A Division CA2466954C (fr) | 1993-08-24 | 1994-08-24 | Oxathiazines antisallissures et antibacterien et leurs oxydes entrant dans les compositions de revetements |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2168357A1 CA2168357A1 (fr) | 1995-03-02 |
| CA2168357C true CA2168357C (fr) | 2006-03-21 |
Family
ID=36101467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002168357A Expired - Fee Related CA2168357C (fr) | 1993-08-24 | 1994-08-24 | Oxathiazines antibacteriennes et antiparasites et leurs oxydes |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2168357C (fr) |
-
1994
- 1994-08-24 CA CA002168357A patent/CA2168357C/fr not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2168357A1 (fr) | 1995-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140826 |