RU2126408C1 - Производные триазолопиримидина, способ их получения, фунгицидный состав, способ борьбы с грибами - Google Patents
Производные триазолопиримидина, способ их получения, фунгицидный состав, способ борьбы с грибами Download PDFInfo
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- RU2126408C1 RU2126408C1 RU94007093A RU94007093A RU2126408C1 RU 2126408 C1 RU2126408 C1 RU 2126408C1 RU 94007093 A RU94007093 A RU 94007093A RU 94007093 A RU94007093 A RU 94007093A RU 2126408 C1 RU2126408 C1 RU 2126408C1
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 241000233866 Fungi Species 0.000 title claims abstract description 11
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 title claims abstract description 7
- 239000000203 mixture Substances 0.000 title claims description 33
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- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
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- 239000000460 chlorine Substances 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 19
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000012025 fluorinating agent Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 11
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- 125000004432 carbon atom Chemical group C* 0.000 description 6
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- 238000000338 in vitro Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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- 125000003282 alkyl amino group Chemical group 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 239000002518 antifoaming agent Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
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- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- 0 *c(c(O)cc1ccn[n]11)c1O Chemical compound *c(c(O)cc1ccn[n]11)c1O 0.000 description 2
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- UPSBAMOBHBBRQS-UHFFFAOYSA-N 5-chloro-n-cyclopentyl-6-thiophen-3-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CSC=C1C=1C(Cl)=NC2=NC=NN2C=1NC1CCCC1 UPSBAMOBHBBRQS-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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|---|---|---|---|
| EP93103465.6 | 1993-03-04 | ||
| EP93103465 | 1993-03-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU94007093A RU94007093A (ru) | 1995-11-10 |
| RU2126408C1 true RU2126408C1 (ru) | 1999-02-20 |
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| EP (1) | EP0613900B1 (enExample) |
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| AT (1) | ATE153025T1 (enExample) |
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| BG (1) | BG61647B1 (enExample) |
| BR (1) | BR9400808A (enExample) |
| CA (1) | CA2116946A1 (enExample) |
| DE (1) | DE69403119T2 (enExample) |
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| IL (1) | IL108731A (enExample) |
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| RO (1) | RO112869B1 (enExample) |
| RU (1) | RU2126408C1 (enExample) |
| SG (1) | SG48897A1 (enExample) |
| TW (1) | TW258648B (enExample) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2524266C1 (ru) * | 2013-03-14 | 2014-07-27 | Федеральное государственное бюджетное учреждение науки Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра Российской академии наук | Средство защиты от плесени |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2147584C1 (ru) * | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
| TW460476B (en) * | 1997-04-14 | 2001-10-21 | American Cyanamid Co | Fungicidal trifluoromethylalkylamino-triazolopyrimidines |
| US6117876A (en) * | 1997-04-14 | 2000-09-12 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| US6559151B2 (en) | 2000-05-08 | 2003-05-06 | Basf Aktiengesellschaft | 6-(2-trifluoromethyl-phenyl)-triazolopyrimidines |
| EP1577312A1 (en) * | 2000-06-13 | 2005-09-21 | Basf Aktiengesellschaft | Triazolopyrimidine intermediate compounds for fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines |
| AU778913B2 (en) | 2000-06-13 | 2004-12-23 | Basf Aktiengesellschaft | Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines |
| TR200402494T4 (tr) * | 2000-12-06 | 2004-12-21 | Wyeth | Mantar öldürücü 6-(2-triflorometil-fenil)-triazolopirimidinler. |
| DE10121101A1 (de) * | 2001-04-27 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| DE10121162A1 (de) | 2001-04-30 | 2002-10-31 | Bayer Ag | Triazolopyrimidine |
| ES2283626T3 (es) * | 2001-07-26 | 2007-11-01 | Basf Aktiengesellschaft | 7-aminotriazolpirimidinas para controlar hongos nocivos. |
| GB0126914D0 (en) * | 2001-11-08 | 2002-01-02 | Syngenta Ltd | Fungicides |
| DE10212886A1 (de) * | 2002-03-22 | 2003-10-02 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10218592A1 (de) * | 2002-04-26 | 2003-11-06 | Bayer Cropscience Ag | Triazolopyrimidine |
| WO2004011467A1 (ja) * | 2002-07-29 | 2004-02-05 | Hokko Chemical Industry Co., Ltd. | トリアゾロピリミジン誘導体および農園芸用殺菌剤 |
| AU2004226253A1 (en) * | 2003-04-02 | 2004-10-14 | Basf Aktiengesellschaft | 7-alkinylamino-triazolopyrimidines, methods for the production and use thereof to combat harmful fungi and agents containing said compounds |
| DE10325133A1 (de) * | 2003-06-04 | 2004-12-23 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10328173A1 (de) * | 2003-06-24 | 2005-01-13 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10328171A1 (de) * | 2003-06-24 | 2005-01-13 | Bayer Cropscience Ag | Triazolopyrimidine |
| DE10328481A1 (de) * | 2003-06-25 | 2005-01-13 | Bayer Ag | Triazolopyrimidine |
| EP1641800B1 (de) * | 2003-06-27 | 2008-03-05 | Bayer CropScience AG | Pyrazolopyrimidine |
| CA2537520A1 (en) * | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 6-aryl-7-halo-imidazo[1,2-a]pyrimidines as anticancer agents |
| BRPI0414700A (pt) * | 2003-09-24 | 2006-11-14 | Wyeth Corp | 6-[(substituìdo)fenil]triazolopirimidinas como agentes anti-cáncer |
| US7419982B2 (en) * | 2003-09-24 | 2008-09-02 | Wyeth Holdings Corporation | Crystalline forms of 5-chloro-6-{2,6-difluoro-4-[3-(methylamino)propoxy]phenyl}-N-[(1S)-2,2,2-trifluoro-1-methylethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine salts |
| MY179926A (en) * | 2003-12-08 | 2020-11-19 | Wyeth Corp | Process for the preparation of tubulin inhibitors |
| DE10360370A1 (de) * | 2003-12-22 | 2005-07-14 | Bayer Cropscience Ag | Triazolopyrimidine |
| PL1725561T3 (pl) * | 2004-03-10 | 2010-12-31 | Basf Se | 5,6-Dialkilo-7-aminotriazolopirymidyny, sposób ich wytwarzania i ich zastosowanie do zwalczania szkodliwych grzybów oraz środki zawierające te związki |
| WO2007006724A1 (de) * | 2005-07-13 | 2007-01-18 | Basf Aktiengesellschaft | 5-alkyl-7-amino-6-heteroaryl-1 , 2 , 4-triazolo (1 , 5-a) pyrimidin-vξrbindungen und ihre? verwendung zur bekämpfung von schadpilzen |
| WO2007023018A1 (de) * | 2005-07-13 | 2007-03-01 | Basf Aktiengesellschaft | 7-amino-6-triazolyl-1,2,4-triazolo[1,5-a]pyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| WO2007023020A1 (de) * | 2005-07-13 | 2007-03-01 | Basf Aktiengeseelschaft | 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidin-verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| US8679514B2 (en) * | 2005-07-27 | 2014-03-25 | Basf Se | Fungicidal mixtures based on azolopyrimidinylamines |
| WO2007012642A1 (de) * | 2005-07-29 | 2007-02-01 | Basf Aktiengesellschaft | 7-amino-6-thiadiazolyl- und -oxadiazolyl- 1 , 2 , 4-triazolo [1 , 5 -a] pyrimidin- verbindungen und ihre verwendung zur bekämpfung von schadpilzen |
| WO2007101870A1 (de) * | 2006-03-08 | 2007-09-13 | Basf Se | Substituierte triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| US20110144049A1 (en) * | 2009-10-21 | 2011-06-16 | Serebruany Victor L | Treating Cardiac Arrhythmias, Heart Failure, Peripheral Artery Disease and Stroke with Cyclopentyl-Triazolo-Pyrimidine or Derivative Thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0071792A2 (de) * | 1981-08-01 | 1983-02-16 | BASF Aktiengesellschaft | 7-Amino-azolo(1,5-a)pyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide |
| EP0141317A2 (de) * | 1983-10-21 | 1985-05-15 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]-pyrimidine und diese enthaltende Fungizide |
| SU1658808A3 (ru) * | 1986-12-19 | 1991-06-23 | Шеринг Аг (Фирма) | Гербицидное и рострегулирующее средство |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH569734A5 (en) * | 1967-07-01 | 1975-11-28 | Hydrierwerk Rodleben Veb | 5-and 7-basically subst s-triazolo 1 5-a pyrimidines |
| US4036840A (en) * | 1972-06-07 | 1977-07-19 | Icn Pharmaceuticals | 2-Substituted-s-triazolo[1,5a]pyrimidines |
| ZA781457B (en) * | 1977-03-23 | 1979-03-28 | Ici Ltd | Pesticidal compounds,compositions and processes |
| US4199584A (en) * | 1977-05-27 | 1980-04-22 | Imperial Chemical Industries Limited | Pesticidal active furo[2,3-d] pyrimidine derivatives, compositions containing the same and use thereof |
| HU208693B (en) * | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
| US5177206A (en) * | 1991-10-08 | 1993-01-05 | Dowelanco | Process for the preparation of substituted N-(aryl)-1,2,4-triazolopyrimidine-2-sulfonamides |
| TW224044B (enExample) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V |
-
1994
- 1994-02-22 IL IL108731A patent/IL108731A/xx not_active IP Right Cessation
- 1994-02-22 TW TW083101519A patent/TW258648B/zh active
- 1994-02-23 NZ NZ250955A patent/NZ250955A/en unknown
- 1994-02-23 AU AU56332/94A patent/AU672267B2/en not_active Ceased
- 1994-02-25 MY MYPI94000448A patent/MY111749A/en unknown
- 1994-03-01 BG BG98637A patent/BG61647B1/bg unknown
- 1994-03-02 AT AT94200532T patent/ATE153025T1/de not_active IP Right Cessation
- 1994-03-02 EP EP94200532A patent/EP0613900B1/en not_active Expired - Lifetime
- 1994-03-02 SG SG1996003569A patent/SG48897A1/en unknown
- 1994-03-02 DE DE69403119T patent/DE69403119T2/de not_active Expired - Fee Related
- 1994-03-02 OA OA60479A patent/OA09891A/en unknown
- 1994-03-02 DK DK94200532.3T patent/DK0613900T3/da active
- 1994-03-02 ES ES94200532T patent/ES2101429T3/es not_active Expired - Lifetime
- 1994-03-03 JP JP05679994A patent/JP3449569B2/ja not_active Expired - Fee Related
- 1994-03-03 RO RO94-00327A patent/RO112869B1/ro unknown
- 1994-03-03 HU HU9400647A patent/HUT68050A/hu unknown
- 1994-03-03 PH PH47874A patent/PH31307A/en unknown
- 1994-03-03 KR KR1019940004137A patent/KR940021554A/ko not_active Withdrawn
- 1994-03-03 BR BR9400808A patent/BR9400808A/pt not_active Application Discontinuation
- 1994-03-03 CA CA002116946A patent/CA2116946A1/en not_active Abandoned
- 1994-03-03 RU RU94007093A patent/RU2126408C1/ru active
- 1994-03-03 ZA ZA941484A patent/ZA941484B/xx unknown
- 1994-03-04 CN CN94102637A patent/CN1094407A/zh active Pending
-
1997
- 1997-04-22 US US08/838,013 patent/US5756509A/en not_active Expired - Fee Related
- 1997-05-30 GR GR970400114T patent/GR3023587T3/el unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0071792A2 (de) * | 1981-08-01 | 1983-02-16 | BASF Aktiengesellschaft | 7-Amino-azolo(1,5-a)pyrimidine, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide |
| EP0141317A2 (de) * | 1983-10-21 | 1985-05-15 | BASF Aktiengesellschaft | 7-Amino-azolo[1,5-a]-pyrimidine und diese enthaltende Fungizide |
| SU1658808A3 (ru) * | 1986-12-19 | 1991-06-23 | Шеринг Аг (Фирма) | Гербицидное и рострегулирующее средство |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2524266C1 (ru) * | 2013-03-14 | 2014-07-27 | Федеральное государственное бюджетное учреждение науки Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра Российской академии наук | Средство защиты от плесени |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69403119D1 (de) | 1997-06-19 |
| EP0613900A1 (en) | 1994-09-07 |
| HU9400647D0 (en) | 1994-05-30 |
| CA2116946A1 (en) | 1994-09-05 |
| HK1001054A1 (en) | 1998-05-22 |
| ES2101429T3 (es) | 1997-07-01 |
| IL108731A (en) | 1997-03-18 |
| US5756509A (en) | 1998-05-26 |
| ZA941484B (en) | 1994-11-10 |
| DK0613900T3 (da) | 1997-06-23 |
| AU672267B2 (en) | 1996-09-26 |
| HUT68050A (en) | 1995-05-29 |
| SG48897A1 (en) | 1998-05-18 |
| BG98637A (en) | 1995-01-31 |
| GR3023587T3 (en) | 1997-08-29 |
| EP0613900B1 (en) | 1997-05-14 |
| AU5633294A (en) | 1994-09-08 |
| BR9400808A (pt) | 1994-11-01 |
| IL108731A0 (en) | 1994-05-30 |
| PH31307A (en) | 1998-07-06 |
| JP3449569B2 (ja) | 2003-09-22 |
| ATE153025T1 (de) | 1997-05-15 |
| RO112869B1 (ro) | 1998-01-30 |
| CN1094407A (zh) | 1994-11-02 |
| JPH072861A (ja) | 1995-01-06 |
| TW258648B (enExample) | 1995-10-01 |
| BG61647B1 (bg) | 1998-02-27 |
| MY111749A (en) | 2000-12-30 |
| KR940021554A (ko) | 1994-10-19 |
| DE69403119T2 (de) | 1997-08-28 |
| OA09891A (en) | 1994-09-15 |
| NZ250955A (en) | 1995-04-27 |
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