NL8004093A - Nieuwe 1-gesubstitueerde-3-cycloalkylsulfonylpyr- rolidine-2,5-dionderivaten, hun gebruik als fungicide, alsmede werkwijze voor de bereiding van deze verbin- dingen en een dergelijk fungicidemiddel. - Google Patents
Nieuwe 1-gesubstitueerde-3-cycloalkylsulfonylpyr- rolidine-2,5-dionderivaten, hun gebruik als fungicide, alsmede werkwijze voor de bereiding van deze verbin- dingen en een dergelijk fungicidemiddel. Download PDFInfo
- Publication number
- NL8004093A NL8004093A NL8004093A NL8004093A NL8004093A NL 8004093 A NL8004093 A NL 8004093A NL 8004093 A NL8004093 A NL 8004093A NL 8004093 A NL8004093 A NL 8004093A NL 8004093 A NL8004093 A NL 8004093A
- Authority
- NL
- Netherlands
- Prior art keywords
- dione
- carbon atoms
- formula
- group
- cyclohexylsulfonylpyrrolidine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 57
- 238000000034 method Methods 0.000 title claims description 49
- 238000002360 preparation method Methods 0.000 title claims description 16
- 230000000855 fungicidal effect Effects 0.000 title claims description 11
- 239000000417 fungicide Substances 0.000 title claims description 10
- 229920004518 DION® Polymers 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- -1 nitro, hydroxy, carboxy, sulfo, sulfonylamino group Chemical group 0.000 claims description 34
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
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- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
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- 150000002367 halogens Chemical class 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- CGHHKCYQBCFICS-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound ClC1=CC=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O CGHHKCYQBCFICS-UHFFFAOYSA-N 0.000 claims description 3
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- YEUSKMIQJAFXJZ-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-(3-nitrophenyl)pyrrolidine-2,5-dione Chemical compound [O-][N+](=O)C1=CC=CC(N2C(C(CC2=O)S(=O)(=O)C2CCCCC2)=O)=C1 YEUSKMIQJAFXJZ-UHFFFAOYSA-N 0.000 claims description 3
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- BAURHTCUCOEKEN-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-hexylpyrrolidine-2,5-dione Chemical compound O=C1N(CCCCCC)C(=O)CC1S(=O)(=O)C1CCCCC1 BAURHTCUCOEKEN-UHFFFAOYSA-N 0.000 claims description 3
- CBJXGRDZASYPAO-UHFFFAOYSA-N 3-cyclohexylsulfonylpyrrolidine-2,5-dione Chemical compound O=C1NC(=O)CC1S(=O)(=O)C1CCCCC1 CBJXGRDZASYPAO-UHFFFAOYSA-N 0.000 claims description 3
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- IDSRCFOZIXELFY-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-(2-methylphenyl)pyrrolidine-2,5-dione Chemical compound C1(=C(C=CC=C1)N1C(C(CC1=O)S(=O)(=O)C1CCCCC1)=O)C IDSRCFOZIXELFY-UHFFFAOYSA-N 0.000 claims 1
- MOTLPVXZHUFIRZ-UHFFFAOYSA-N 3-cyclohexylsulfonyl-1-(3,4-dihydroxyphenyl)pyrrolidine-2,5-dione Chemical compound C1=C(O)C(O)=CC=C1N1C(=O)C(S(=O)(=O)C2CCCCC2)CC1=O MOTLPVXZHUFIRZ-UHFFFAOYSA-N 0.000 claims 1
- PLGNAYDAIVMEPN-UHFFFAOYSA-N 3-cyclooctylsulfonyl-1-phenylpyrrolidine-2,5-dione Chemical compound O=C1CC(S(=O)(=O)C2CCCCCCC2)C(=O)N1C1=CC=CC=C1 PLGNAYDAIVMEPN-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
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- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- POLAIXDPYKNITQ-UHFFFAOYSA-N methyl 2-acetyloxy-4-(3-cyclohexylsulfanyl-2,5-dioxopyrrolidin-1-yl)benzoate Chemical compound C1=C(OC(C)=O)C(C(=O)OC)=CC=C1N1C(=O)C(SC2CCCCC2)CC1=O POLAIXDPYKNITQ-UHFFFAOYSA-N 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI001951 | 1979-07-17 | ||
| HU79CI1951A HU178455B (en) | 1979-07-17 | 1979-07-17 | Process for producing new 1-substituted-3-cycloalkyl-sulfonyl-pyrrolidine-2,5-dione derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8004093A true NL8004093A (nl) | 1981-01-20 |
Family
ID=10994755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8004093A NL8004093A (nl) | 1979-07-17 | 1980-07-16 | Nieuwe 1-gesubstitueerde-3-cycloalkylsulfonylpyr- rolidine-2,5-dionderivaten, hun gebruik als fungicide, alsmede werkwijze voor de bereiding van deze verbin- dingen en een dergelijk fungicidemiddel. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4364958A (ru) |
| JP (1) | JPS5639067A (ru) |
| AT (1) | AT374177B (ru) |
| AU (1) | AU535388B2 (ru) |
| BE (1) | BE884353A (ru) |
| CA (1) | CA1135707A (ru) |
| CH (1) | CH651296A5 (ru) |
| CS (1) | CS226015B2 (ru) |
| DD (3) | DD156562A5 (ru) |
| DE (1) | DE3026755A1 (ru) |
| DK (1) | DK159418C (ru) |
| ES (1) | ES494310A0 (ru) |
| FI (1) | FI74948C (ru) |
| FR (1) | FR2461700A1 (ru) |
| GB (1) | GB2054589B (ru) |
| GR (1) | GR69590B (ru) |
| HU (1) | HU178455B (ru) |
| IL (1) | IL60612A (ru) |
| IN (1) | IN151488B (ru) |
| IT (1) | IT1141606B (ru) |
| LU (1) | LU82636A1 (ru) |
| NL (1) | NL8004093A (ru) |
| NO (1) | NO154493C (ru) |
| PL (4) | PL127256B1 (ru) |
| SE (1) | SE450831B (ru) |
| SU (5) | SU1373704A1 (ru) |
| YU (1) | YU41935B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3637507A1 (de) * | 1986-11-04 | 1988-05-05 | Bayer Ag | Neues verfahren zur herstellung von teilweise neuen 3-sulfenylmaleinimiden und ihre verwendung |
| DE3719764A1 (de) * | 1987-06-13 | 1988-12-22 | Bayer Ag | Ionenaustauscherharze beladen mit chinoloncarbonsaeurederivaten, ihre herstellung und verwendung |
| US5892057A (en) | 1997-09-18 | 1999-04-06 | Pierce Chemical Company | Preparation of sulfo-N-hydroxysuccinimide salts |
| WO1999014192A1 (en) * | 1997-09-18 | 1999-03-25 | Pierce Chemical Company | Sulfo-n-hydroxy succinimide and method of preparation |
| WO2000017162A1 (fr) | 1998-09-21 | 2000-03-30 | Takeda Chemical Industries, Ltd. | Nouveaux derives de thiol, leur procede de production et leur utilisation |
| HU226421B1 (en) * | 1998-11-09 | 2008-12-29 | Sanofi Aventis | Process for racemizing optically active 2-(2-chlorophenyl)-2-(2-(2-thienyl)-ethylamino)-acetamides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538114A (en) * | 1966-08-12 | 1970-11-03 | Basf Ag | N-(substituted-phenyl)-succinimides |
| GB1319772A (en) * | 1969-06-18 | 1973-06-06 | Geistlich Soehne Ag | Succinimides |
| US3804856A (en) * | 1970-09-04 | 1974-04-16 | Sumitomo Chemical Co | N-phenylsuccinimides |
| DE2143601C3 (de) * | 1970-09-04 | 1981-12-24 | Sumitomo Chemical Co., Ltd., Osaka | N-Phenylsuccimidderivate, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Mikroorganismen |
| JPS4833025A (ru) * | 1971-08-28 | 1973-05-07 | ||
| JPS5412904B2 (ru) * | 1973-05-18 | 1979-05-26 |
-
1979
- 1979-07-17 HU HU79CI1951A patent/HU178455B/hu not_active IP Right Cessation
-
1980
- 1980-07-15 DE DE19803026755 patent/DE3026755A1/de active Granted
- 1980-07-16 LU LU82636A patent/LU82636A1/de unknown
- 1980-07-16 GR GR62474A patent/GR69590B/el unknown
- 1980-07-16 CH CH5466/80A patent/CH651296A5/de not_active IP Right Cessation
- 1980-07-16 SU SU802950855A patent/SU1373704A1/ru active
- 1980-07-16 PL PL1980231601A patent/PL127256B1/pl unknown
- 1980-07-16 PL PL1980231600A patent/PL127257B1/pl unknown
- 1980-07-16 DD DD80227898A patent/DD156562A5/de not_active IP Right Cessation
- 1980-07-16 SE SE8005208A patent/SE450831B/sv not_active IP Right Cessation
- 1980-07-16 PL PL1980231602A patent/PL127255B1/pl unknown
- 1980-07-16 IN IN814/CAL/80A patent/IN151488B/en unknown
- 1980-07-16 NL NL8004093A patent/NL8004093A/nl not_active Application Discontinuation
- 1980-07-16 CS CS805047A patent/CS226015B2/cs unknown
- 1980-07-16 YU YU1830/80A patent/YU41935B/xx unknown
- 1980-07-16 DK DK307580A patent/DK159418C/da not_active IP Right Cessation
- 1980-07-16 NO NO802134A patent/NO154493C/no unknown
- 1980-07-16 DD DD80222669A patent/DD152126A5/de not_active IP Right Cessation
- 1980-07-16 GB GB8023219A patent/GB2054589B/en not_active Expired
- 1980-07-16 DD DD80227899A patent/DD156572A5/de not_active IP Right Cessation
- 1980-07-16 AT AT0368480A patent/AT374177B/de not_active IP Right Cessation
- 1980-07-16 SU SU802953400A patent/SU1007555A3/ru active
- 1980-07-16 IL IL60612A patent/IL60612A/xx unknown
- 1980-07-16 US US06/169,439 patent/US4364958A/en not_active Expired - Lifetime
- 1980-07-16 FR FR8015678A patent/FR2461700A1/fr active Granted
- 1980-07-16 PL PL1980225695A patent/PL127097B1/pl unknown
- 1980-07-17 AU AU60480/80A patent/AU535388B2/en not_active Ceased
- 1980-07-17 IT IT68139/80A patent/IT1141606B/it active
- 1980-07-17 BE BE0/201435A patent/BE884353A/fr not_active IP Right Cessation
- 1980-07-17 JP JP9813780A patent/JPS5639067A/ja active Granted
- 1980-07-17 ES ES494310A patent/ES494310A0/es active Granted
- 1980-07-17 CA CA000356425A patent/CA1135707A/en not_active Expired
- 1980-07-17 FI FI802268A patent/FI74948C/fi not_active IP Right Cessation
-
1981
- 1981-08-12 SU SU813322502A patent/SU1165231A3/ru active
- 1981-08-12 SU SU813315400A patent/SU1192616A3/ru active
- 1981-08-12 SU SU813317073A patent/SU1156594A3/ru active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| BC | A request for examination has been filed | ||
| BV | The patent application has lapsed |