SK72196A3 - Method for producing 1-{£2-(cyclopropylcarbonyl)- phenyl| sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) of urea and intermediate products of this method - Google Patents
Method for producing 1-{£2-(cyclopropylcarbonyl)- phenyl| sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) of urea and intermediate products of this method Download PDFInfo
- Publication number
- SK72196A3 SK72196A3 SK721-96A SK72196A SK72196A3 SK 72196 A3 SK72196 A3 SK 72196A3 SK 72196 A SK72196 A SK 72196A SK 72196 A3 SK72196 A3 SK 72196A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- cyclopropylcarbonyl
- solvent
- reacted
- pyrimidinyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 title claims description 11
- 239000004202 carbamide Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 239000013067 intermediate product Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 2-Cyclopropylcarbonyl Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 235000013877 carbamide Nutrition 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- HMOJKUDFFLOQTN-UHFFFAOYSA-N (2-aminophenyl)-cyclopropylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1CC1 HMOJKUDFFLOQTN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 claims 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 8
- 150000003672 ureas Chemical class 0.000 abstract description 6
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004009 herbicide Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DMSHKCSGFNYTCM-UHFFFAOYSA-N S(=O)(=O)(O)N(C(=O)N)CCCCC Chemical class S(=O)(=O)(O)N(C(=O)N)CCCCC DMSHKCSGFNYTCM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- BNOVYBVKWYHEMQ-UHFFFAOYSA-N (4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(N)=O)=N1 BNOVYBVKWYHEMQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QYUMJJIZNNMDKF-UHFFFAOYSA-N 1-[[2-(cyclopropanecarbonyl)phenyl]sulfamoyl]-3-(4,6-dichloropyrimidin-2-yl)urea Chemical compound ClC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 QYUMJJIZNNMDKF-UHFFFAOYSA-N 0.000 description 1
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003673 groundwater Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/465,049 US5847140A (en) | 1995-06-06 | 1995-06-06 | Intermediates for the manufacture of herbicidal 1-{ 2-(cyclopropylcarbonyl) Phenyl! Sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) urea compounds |
| US08/468,101 US5559234A (en) | 1995-06-06 | 1995-06-06 | Process for the manufacture of herbicidal 1-{[2-(cyclopropylcarbonyl)phyenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK72196A3 true SK72196A3 (en) | 1997-05-07 |
Family
ID=27041193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK721-96A SK72196A3 (en) | 1995-06-06 | 1996-06-05 | Method for producing 1-{£2-(cyclopropylcarbonyl)- phenyl| sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl) of urea and intermediate products of this method |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0747365B1 (fr) |
| JP (1) | JP4176163B2 (fr) |
| KR (1) | KR100474231B1 (fr) |
| CN (1) | CN1141293A (fr) |
| AR (1) | AR002341A1 (fr) |
| AT (1) | ATE273287T1 (fr) |
| AU (1) | AU714224B2 (fr) |
| BR (1) | BR9602655A (fr) |
| CA (1) | CA2178174C (fr) |
| CO (1) | CO4650164A1 (fr) |
| CZ (1) | CZ287105B6 (fr) |
| DE (1) | DE69633093T2 (fr) |
| DK (1) | DK0747365T3 (fr) |
| ES (1) | ES2224154T3 (fr) |
| HU (1) | HU216660B (fr) |
| IL (1) | IL118505A (fr) |
| SK (1) | SK72196A3 (fr) |
| TW (1) | TW345578B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1290062B1 (it) * | 1997-03-13 | 1998-10-19 | Isagro Ricerca Srl | Amminosolfoniluree ad attivita' erbicida |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH580607A5 (fr) * | 1973-08-17 | 1976-10-15 | Ciba Geigy Ag | |
| US4401816A (en) * | 1980-04-29 | 1983-08-30 | E. I. Du Pont De Nemours And Company | Sulfamoyl chlorides |
| US4369320A (en) * | 1980-11-03 | 1983-01-18 | E. I. Du Pont De Nemours And Company | N-[Heterocyclicaminocarbonyl]-8-quinolinesulfonamides |
| US4954164A (en) * | 1982-02-27 | 1990-09-04 | Nissan Chemical Industries, Ltd. | Pyrazolesulfonylurea derivatives, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof |
| US5009699A (en) * | 1990-06-22 | 1991-04-23 | American Cyanamid Company | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
| DE4024867A1 (de) * | 1990-08-04 | 1992-02-06 | Bayer Ag | Verfahren zur herstellung von oxyguanidinen |
| US5280007A (en) * | 1991-12-18 | 1994-01-18 | American Cyanamid Company | Method for safening rice against the phytotoxic effects of a sulfamoyl urea herbicide |
| DE4337847A1 (de) * | 1993-11-05 | 1995-05-11 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
| DE4414476A1 (de) * | 1994-04-26 | 1995-11-02 | Bayer Ag | Substituierte Cyclopropylcarbonyl-phenylaminosulfonyl-harnstoffe |
| US5492884A (en) * | 1994-04-29 | 1996-02-20 | American Cyanamid Company | 1-[2-(cyclopropylcarbonyl)-4-fluorophenyl]sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl) urea and its herbicidal method of use |
-
1996
- 1996-05-30 CZ CZ19961572A patent/CZ287105B6/cs not_active IP Right Cessation
- 1996-05-31 DK DK96303928T patent/DK0747365T3/da active
- 1996-05-31 IL IL11850596A patent/IL118505A/xx not_active IP Right Cessation
- 1996-05-31 DE DE69633093T patent/DE69633093T2/de not_active Expired - Lifetime
- 1996-05-31 ES ES96303928T patent/ES2224154T3/es not_active Expired - Lifetime
- 1996-05-31 AT AT96303928T patent/ATE273287T1/de active
- 1996-05-31 EP EP96303928A patent/EP0747365B1/fr not_active Expired - Lifetime
- 1996-06-03 AU AU54711/96A patent/AU714224B2/en not_active Ceased
- 1996-06-03 CO CO96028501A patent/CO4650164A1/es unknown
- 1996-06-04 CA CA002178174A patent/CA2178174C/fr not_active Expired - Fee Related
- 1996-06-04 JP JP16249696A patent/JP4176163B2/ja not_active Expired - Fee Related
- 1996-06-05 SK SK721-96A patent/SK72196A3/sk unknown
- 1996-06-05 BR BR9602655A patent/BR9602655A/pt not_active IP Right Cessation
- 1996-06-05 KR KR1019960020041A patent/KR100474231B1/ko not_active Expired - Lifetime
- 1996-06-05 AR ARP960102961A patent/AR002341A1/es unknown
- 1996-06-06 CN CN96106821A patent/CN1141293A/zh active Pending
- 1996-06-06 HU HU9601560A patent/HU216660B/hu not_active IP Right Cessation
- 1996-07-09 TW TW085108305A patent/TW345578B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP0747365B1 (fr) | 2004-08-11 |
| HU216660B (hu) | 1999-07-28 |
| ES2224154T3 (es) | 2005-03-01 |
| KR100474231B1 (ko) | 2005-08-17 |
| BR9602655A (pt) | 1998-10-06 |
| IL118505A0 (en) | 1996-09-12 |
| AR002341A1 (es) | 1998-03-11 |
| HUP9601560A3 (en) | 1997-08-28 |
| CO4650164A1 (es) | 1998-09-03 |
| AU5471196A (en) | 1996-12-19 |
| JPH093050A (ja) | 1997-01-07 |
| IL118505A (en) | 2000-02-29 |
| TW345578B (en) | 1998-11-21 |
| EP0747365A1 (fr) | 1996-12-11 |
| DE69633093D1 (de) | 2004-09-16 |
| CA2178174C (fr) | 2008-07-29 |
| AU714224B2 (en) | 1999-12-23 |
| CA2178174A1 (fr) | 1996-12-07 |
| CN1141293A (zh) | 1997-01-29 |
| CZ157296A3 (en) | 1997-01-15 |
| HU9601560D0 (en) | 1996-08-28 |
| JP4176163B2 (ja) | 2008-11-05 |
| DE69633093T2 (de) | 2005-01-20 |
| HUP9601560A2 (en) | 1997-04-28 |
| ATE273287T1 (de) | 2004-08-15 |
| CZ287105B6 (en) | 2000-09-13 |
| DK0747365T3 (da) | 2004-09-06 |
| KR970001331A (ko) | 1997-01-24 |
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