SK281074B6 - 1-{[alfa-cyklopropyl-alfa-(substituovaný oxy)-o-tolyl]sulfamoyl}- -3-(4,6-dimetoxy-2-pyrimidinyl)močovinové deriváty, spôsob potláčania nežiaducich druhov rastlín pomocou týchto derivátov a herbicídne prostriedky na ich báze - Google Patents
1-{[alfa-cyklopropyl-alfa-(substituovaný oxy)-o-tolyl]sulfamoyl}- -3-(4,6-dimetoxy-2-pyrimidinyl)močovinové deriváty, spôsob potláčania nežiaducich druhov rastlín pomocou týchto derivátov a herbicídne prostriedky na ich báze Download PDFInfo
- Publication number
- SK281074B6 SK281074B6 SK1581-94A SK158194A SK281074B6 SK 281074 B6 SK281074 B6 SK 281074B6 SK 158194 A SK158194 A SK 158194A SK 281074 B6 SK281074 B6 SK 281074B6
- Authority
- SK
- Slovakia
- Prior art keywords
- sulfamoyl
- dimethoxy
- tolyl
- cyclopropyl
- pyrimidinyl
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims abstract description 54
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- -1 1-{[alpha-cyclopropyl-alpha-(substituted oxy)-o-tolyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea compounds Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002689 soil Substances 0.000 claims description 16
- 235000007164 Oryza sativa Nutrition 0.000 claims description 14
- 235000009566 rice Nutrition 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 210000000056 organ Anatomy 0.000 claims description 10
- WTWCAOMFNAGKBO-UHFFFAOYSA-N 1-[[2-[cyclopropyl(hydroxy)methyl]phenyl]sulfamoyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(O)C2CC2)=N1 WTWCAOMFNAGKBO-UHFFFAOYSA-N 0.000 claims description 7
- 230000001902 propagating effect Effects 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- BNOVYBVKWYHEMQ-UHFFFAOYSA-N (4,6-dimethoxypyrimidin-2-yl)urea Chemical class COC1=CC(OC)=NC(NC(N)=O)=N1 BNOVYBVKWYHEMQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 241000209094 Oryza Species 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 240000007594 Oryza sativa Species 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 244000060234 Gmelina philippensis Species 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OJXASOYYODXRPT-UHFFFAOYSA-N sulfamoylurea Chemical class NC(=O)NS(N)(=O)=O OJXASOYYODXRPT-UHFFFAOYSA-N 0.000 description 3
- XUKYFQQFUSKNAU-UHFFFAOYSA-N (2-aminophenyl)-cyclopropylmethanol Chemical compound NC1=CC=CC=C1C(O)C1CC1 XUKYFQQFUSKNAU-UHFFFAOYSA-N 0.000 description 2
- LVFRCHIUUKWBLR-UHFFFAOYSA-N 4,6-dimethoxypyrimidin-2-amine Chemical group COC1=CC(OC)=NC(N)=N1 LVFRCHIUUKWBLR-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000289659 Erinaceidae Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- 240000000178 Monochoria vaginalis Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HFDZWFJREPJRBW-UHFFFAOYSA-N acetic acid;1-[[2-[cyclopropyl(hydroxy)methyl]phenyl]sulfamoyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound CC(O)=O.COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(O)C2CC2)=N1 HFDZWFJREPJRBW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 241001233957 eudicotyledons Species 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- HMOJKUDFFLOQTN-UHFFFAOYSA-N (2-aminophenyl)-cyclopropylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1CC1 HMOJKUDFFLOQTN-UHFFFAOYSA-N 0.000 description 1
- VXGWAWGQKJMAMN-UHFFFAOYSA-N (carbamoylamino) acetate Chemical compound CC(=O)ONC(N)=O VXGWAWGQKJMAMN-UHFFFAOYSA-N 0.000 description 1
- 241001290610 Abildgaardia Species 0.000 description 1
- 241000219144 Abutilon Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000258957 Asteroidea Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 235000005291 Rumex acetosa Nutrition 0.000 description 1
- 240000007001 Rumex acetosella Species 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000208041 Veronica Species 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000006278 hypochromic anemia Diseases 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000003513 sheep sorrel Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 244000082735 tidal marsh flat sedge Species 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/174,506 US5464808A (en) | 1993-12-28 | 1993-12-28 | 1-[α-cyclopropyl-α-(substituted oxy)-o-tolyl]sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK158194A3 SK158194A3 (en) | 1995-08-09 |
| SK281074B6 true SK281074B6 (sk) | 2000-11-07 |
Family
ID=22636413
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1581-94A SK281074B6 (sk) | 1993-12-28 | 1994-12-21 | 1-{[alfa-cyklopropyl-alfa-(substituovaný oxy)-o-tolyl]sulfamoyl}- -3-(4,6-dimetoxy-2-pyrimidinyl)močovinové deriváty, spôsob potláčania nežiaducich druhov rastlín pomocou týchto derivátov a herbicídne prostriedky na ich báze |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5464808A (zh) |
| EP (1) | EP0661275B1 (zh) |
| JP (1) | JP3513781B2 (zh) |
| KR (1) | KR100343657B1 (zh) |
| CN (1) | CN1047593C (zh) |
| AT (1) | ATE154599T1 (zh) |
| AU (1) | AU675022B2 (zh) |
| BR (1) | BR9405263A (zh) |
| CA (1) | CA2139046A1 (zh) |
| CZ (1) | CZ284348B6 (zh) |
| DE (1) | DE69403886T2 (zh) |
| DK (1) | DK0661275T3 (zh) |
| ES (1) | ES2105480T3 (zh) |
| GR (1) | GR3023923T3 (zh) |
| HK (1) | HK1001057A1 (zh) |
| HU (1) | HU214291B (zh) |
| IL (1) | IL112154A (zh) |
| MY (1) | MY111499A (zh) |
| PH (1) | PH31159A (zh) |
| RU (1) | RU2141954C1 (zh) |
| SG (1) | SG47991A1 (zh) |
| SK (1) | SK281074B6 (zh) |
| TW (1) | TW290431B (zh) |
| UA (1) | UA42694C2 (zh) |
| ZA (1) | ZA9410328B (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9833999B2 (en) * | 2013-11-19 | 2017-12-05 | Archroma Ip Gmbh | Inkjet printing system |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666508A (en) * | 1985-06-25 | 1987-05-19 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
| US4741762A (en) * | 1985-06-25 | 1988-05-03 | Ppg Industries, Inc. | Sulfamoyl urea derivatives |
| ATE113938T1 (de) * | 1989-07-19 | 1994-11-15 | Hoechst Schering Agrevo Gmbh | Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren. |
| 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 |
| JP3388902B2 (ja) * | 1994-09-20 | 2003-03-24 | 株式会社ブリヂストン | 空気入りラジアルタイヤ |
-
1993
- 1993-12-28 US US08/174,506 patent/US5464808A/en not_active Expired - Fee Related
-
1994
- 1994-12-12 DK DK94119615.6T patent/DK0661275T3/da active
- 1994-12-12 DE DE69403886T patent/DE69403886T2/de not_active Expired - Fee Related
- 1994-12-12 SG SG1996005955A patent/SG47991A1/en unknown
- 1994-12-12 AT AT94119615T patent/ATE154599T1/de not_active IP Right Cessation
- 1994-12-12 EP EP94119615A patent/EP0661275B1/en not_active Expired - Lifetime
- 1994-12-12 ES ES94119615T patent/ES2105480T3/es not_active Expired - Lifetime
- 1994-12-15 MY MYPI94003367A patent/MY111499A/en unknown
- 1994-12-16 CZ CZ943186A patent/CZ284348B6/cs not_active IP Right Cessation
- 1994-12-20 PH PH49634A patent/PH31159A/en unknown
- 1994-12-21 SK SK1581-94A patent/SK281074B6/sk unknown
- 1994-12-22 AU AU81683/94A patent/AU675022B2/en not_active Ceased
- 1994-12-23 CA CA002139046A patent/CA2139046A1/en not_active Abandoned
- 1994-12-26 UA UA94129249A patent/UA42694C2/uk unknown
- 1994-12-26 JP JP33725894A patent/JP3513781B2/ja not_active Expired - Fee Related
- 1994-12-27 BR BR9405263A patent/BR9405263A/pt not_active Application Discontinuation
- 1994-12-27 IL IL11215494A patent/IL112154A/xx not_active IP Right Cessation
- 1994-12-27 HU HU9403799A patent/HU214291B/hu not_active IP Right Cessation
- 1994-12-27 KR KR1019940037433A patent/KR100343657B1/ko not_active IP Right Cessation
- 1994-12-27 ZA ZA9410328A patent/ZA9410328B/xx unknown
- 1994-12-27 RU RU94045284A patent/RU2141954C1/ru not_active IP Right Cessation
- 1994-12-28 CN CN94113230A patent/CN1047593C/zh not_active Expired - Fee Related
-
1995
- 1995-01-25 TW TW084100663A patent/TW290431B/zh active
-
1997
- 1997-06-27 GR GR970400112T patent/GR3023923T3/el unknown
-
1998
- 1998-01-05 HK HK98100069A patent/HK1001057A1/xx not_active IP Right Cessation
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