CS248740B2 - Production method of the derivatives of 3-tetrahydronaftyl-4-hydroxy-2h-(1)-benzothiopyran-2 - Google Patents
Production method of the derivatives of 3-tetrahydronaftyl-4-hydroxy-2h-(1)-benzothiopyran-2 Download PDFInfo
- Publication number
- CS248740B2 CS248740B2 CS852622A CS262285A CS248740B2 CS 248740 B2 CS248740 B2 CS 248740B2 CS 852622 A CS852622 A CS 852622A CS 262285 A CS262285 A CS 262285A CS 248740 B2 CS248740 B2 CS 248740B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compound
- hydroxy
- derivatives
- benzothiopyran
- days
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- -1 1-Phenyl-3-oxobutyl Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000283160 Inia Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229930003448 Vitamin K Natural products 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 235000019168 vitamin K Nutrition 0.000 description 2
- 239000011712 vitamin K Substances 0.000 description 2
- 150000003721 vitamin K derivatives Chemical class 0.000 description 2
- 229940046010 vitamin k Drugs 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical group C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 description 1
- 240000002834 Paulownia tomentosa Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 241000700161 Rattus rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000007813 chromatographic assay Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001119 rodenticidal effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 1
- 229960005080 warfarin Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8405794A FR2562893B1 (fr) | 1984-04-12 | 1984-04-12 | Derives de l'hydroxy-4-2h-1-benzothiopyran-2-one, leurs preparations et applications dans le domaine rodenticide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS248740B2 true CS248740B2 (en) | 1987-02-12 |
Family
ID=9303113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS852622A CS248740B2 (en) | 1984-04-12 | 1985-04-09 | Production method of the derivatives of 3-tetrahydronaftyl-4-hydroxy-2h-(1)-benzothiopyran-2 |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US4585786A (en]) |
| EP (1) | EP0161163B1 (en]) |
| JP (1) | JP2504941B2 (en]) |
| KR (1) | KR920010394B1 (en]) |
| CN (1) | CN85103105B (en]) |
| AR (1) | AR240047A1 (en]) |
| AT (1) | ATE29881T1 (en]) |
| AU (1) | AU572279B2 (en]) |
| BG (1) | BG44024A3 (en]) |
| CA (1) | CA1248963A (en]) |
| CS (1) | CS248740B2 (en]) |
| DD (1) | DD231794A5 (en]) |
| DE (1) | DE3560679D1 (en]) |
| DK (1) | DK164319C (en]) |
| DZ (1) | DZ768A1 (en]) |
| EG (1) | EG18087A (en]) |
| ES (1) | ES8603454A1 (en]) |
| FI (1) | FI79310C (en]) |
| FR (1) | FR2562893B1 (en]) |
| GE (1) | GEP19960312B (en]) |
| GR (1) | GR850850B (en]) |
| HK (1) | HK40188A (en]) |
| HR (1) | HRP921043B1 (en]) |
| HU (1) | HU194552B (en]) |
| IE (1) | IE57955B1 (en]) |
| IL (1) | IL74727A (en]) |
| IN (1) | IN163166B (en]) |
| MA (1) | MA20407A1 (en]) |
| MX (1) | MX159654A (en]) |
| NO (1) | NO169339C (en]) |
| NZ (1) | NZ211660A (en]) |
| OA (1) | OA07993A (en]) |
| PL (1) | PL145203B1 (en]) |
| PT (1) | PT80264B (en]) |
| SI (1) | SI8510556A8 (en]) |
| SU (1) | SU1373321A3 (en]) |
| TR (1) | TR22145A (en]) |
| YU (1) | YU45251B (en]) |
| ZA (1) | ZA852459B (en]) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8729557D0 (en) | 1987-12-18 | 1988-02-03 | Shell Int Research | Rodenticidal composition |
| US5278186A (en) * | 1990-02-10 | 1994-01-11 | Takeda Chemical Industries, Ltd. | Chromene derivatives, their production and use |
| US5449514A (en) * | 1990-09-11 | 1995-09-12 | Liphatech, Inc. | Bait block |
| WO1994008988A1 (en) * | 1992-10-15 | 1994-04-28 | Idemitsu Kosan Co., Ltd. | Cyclohexanedione derivative |
| FR2765579A1 (fr) * | 1997-07-01 | 1999-01-08 | Lipha | Nouveaux derives de 4-hydroxy-2h-1-(thio)pyran-2-ones leurs preparations et leurs utilisations comme rodonticides |
| AU2003226826B2 (en) * | 2002-05-07 | 2008-10-30 | Bayer Cropscience Ag | Rodenticidal bait system |
| GB0211019D0 (en) * | 2002-05-14 | 2002-06-26 | Syngenta Ltd | Novel compounds |
| JP4629724B2 (ja) | 2007-12-20 | 2011-02-09 | 三菱自動車工業株式会社 | インジェクタの取付け構造 |
| CN105037323A (zh) * | 2008-11-14 | 2015-11-11 | 菲布罗根有限公司 | 作为hif羟化酶抑制剂的苯并噻喃衍生物 |
| FR3045048B1 (fr) * | 2015-12-11 | 2019-04-05 | Liphatech | Stereo-isomere de configuration de la difethialone, composition et appat rodonticide le comprenant et procede de lutte contre des rongeurs cibles nuisibles |
| FR3045051B1 (fr) * | 2015-12-11 | 2019-04-05 | Liphatech | Stereo-isomere de configuration de la difethialone, composition et appat rodonticide le comprenant et procede de lutte contre des rongeurs cibles nuisibles |
| FR3045049B1 (fr) * | 2015-12-11 | 2019-04-05 | Liphatech | Stereo-isomere de configuration de la difethialone, composition et appat rodonticide le comprenant et procede de lutte contre des rongeurs cibles nuisibles |
| FR3045050B1 (fr) * | 2015-12-11 | 2019-06-21 | Liphatech | Stereo-isomere de configuration de la difethialone, composition et appat rodonticide le comprenant et procede de lutte contre des rongeurs cibles nuisibles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA547244A (en) * | 1957-10-08 | Litvan Franz | 3-substituted 4-hydroxycoumarins and process for their production | |
| US3022317A (en) * | 1956-01-20 | 1962-02-20 | Geigy Chem Corp | 3-benzyl-4-hydroxycoumarin and a process for the preparation of derivatives of 3-benzyl-4-hydroxycoumarin |
| US3764693A (en) * | 1969-11-21 | 1973-10-09 | Lipha | A rodenticidal compositions containing 4-hydroxy coumarins |
| FR2351653A1 (fr) * | 1976-05-21 | 1977-12-16 | Mo Khim T | Derive de thio-1 hydroxy-4 coumarine, leur procede de preparation et leurs applications |
| EP0098629B1 (en) * | 1982-06-14 | 1987-08-26 | Shell Internationale Researchmaatschappij B.V. | Anti-coagulants of the 4-hydroxycoumarin type, the preparation thereof, and rodenticidal compositions (baits) comprising such anti-coagulants |
-
1984
- 1984-04-12 FR FR8405794A patent/FR2562893B1/fr not_active Expired
-
1985
- 1985-03-26 IL IL74727A patent/IL74727A/xx not_active IP Right Cessation
- 1985-03-27 US US06/716,394 patent/US4585786A/en not_active Expired - Lifetime
- 1985-03-30 IN IN275/DEL/85A patent/IN163166B/en unknown
- 1985-04-01 ZA ZA852459A patent/ZA852459B/xx unknown
- 1985-04-02 NZ NZ211660A patent/NZ211660A/en unknown
- 1985-04-03 YU YU556/85A patent/YU45251B/xx unknown
- 1985-04-03 SI SI8510556A patent/SI8510556A8/sl unknown
- 1985-04-04 GR GR850850A patent/GR850850B/el unknown
- 1985-04-04 AU AU40868/85A patent/AU572279B2/en not_active Expired
- 1985-04-04 IE IE874/85A patent/IE57955B1/en not_active IP Right Cessation
- 1985-04-07 DZ DZ850075A patent/DZ768A1/fr active
- 1985-04-09 MX MX8260A patent/MX159654A/es unknown
- 1985-04-09 DE DE8585400695T patent/DE3560679D1/de not_active Expired
- 1985-04-09 EP EP85400695A patent/EP0161163B1/fr not_active Expired
- 1985-04-09 AT AT85400695T patent/ATE29881T1/de not_active IP Right Cessation
- 1985-04-09 CS CS852622A patent/CS248740B2/cs not_active IP Right Cessation
- 1985-04-10 TR TR22145A patent/TR22145A/xx unknown
- 1985-04-10 EG EG233/85A patent/EG18087A/xx active
- 1985-04-11 PT PT80264A patent/PT80264B/pt unknown
- 1985-04-11 AR AR300054A patent/AR240047A1/es active
- 1985-04-11 NO NO851448A patent/NO169339C/no not_active IP Right Cessation
- 1985-04-11 DK DK163285A patent/DK164319C/da not_active IP Right Cessation
- 1985-04-11 FI FI851459A patent/FI79310C/fi not_active IP Right Cessation
- 1985-04-11 DD DD85275100A patent/DD231794A5/de not_active IP Right Cessation
- 1985-04-11 KR KR1019850002419A patent/KR920010394B1/ko not_active Expired
- 1985-04-11 SU SU853880299A patent/SU1373321A3/ru active
- 1985-04-11 HU HU851346A patent/HU194552B/hu unknown
- 1985-04-11 ES ES542149A patent/ES8603454A1/es not_active Expired
- 1985-04-11 PL PL1985252882A patent/PL145203B1/pl unknown
- 1985-04-12 MA MA20631A patent/MA20407A1/fr unknown
- 1985-04-12 JP JP60076883A patent/JP2504941B2/ja not_active Expired - Lifetime
- 1985-04-12 BG BG069734A patent/BG44024A3/xx unknown
- 1985-04-12 CA CA000479039A patent/CA1248963A/fr not_active Expired
- 1985-04-12 OA OA58569A patent/OA07993A/xx unknown
- 1985-04-25 CN CN85103105A patent/CN85103105B/zh not_active Expired
-
1988
- 1988-06-02 HK HK401/88A patent/HK40188A/xx not_active IP Right Cessation
-
1992
- 1992-10-13 HR HRP-556/85A patent/HRP921043B1/xx not_active IP Right Cessation
-
1993
- 1993-03-09 GE GEAP1993574A patent/GEP19960312B/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Effective date: 20000409 |