DD291997A5 - Verfahren zur herstellung von propensaeurederivaten - Google Patents
Verfahren zur herstellung von propensaeurederivaten Download PDFInfo
- Publication number
- DD291997A5 DD291997A5 DD90337681A DD33768190A DD291997A5 DD 291997 A5 DD291997 A5 DD 291997A5 DD 90337681 A DD90337681 A DD 90337681A DD 33768190 A DD33768190 A DD 33768190A DD 291997 A5 DD291997 A5 DD 291997A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- compound
- cyano
- formula
- ppm
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 12
- 241000233866 Fungi Species 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000000203 mixture Substances 0.000 claims description 49
- -1 C2 _4-alkynyloxy Chemical group 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Chemical group 0.000 claims description 6
- 239000002184 metal Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- 206010017533 Fungal infection Diseases 0.000 abstract description 3
- 208000031888 Mycoses Diseases 0.000 abstract description 3
- 238000003898 horticulture Methods 0.000 abstract description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
- 241000196324 Embryophyta Species 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
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- 240000005979 Hordeum vulgare Species 0.000 description 9
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- 239000000543 intermediate Substances 0.000 description 8
- 244000105624 Arachis hypogaea Species 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
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- 238000004587 chromatography analysis Methods 0.000 description 7
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 235000020232 peanut Nutrition 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003337 fertilizer Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
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- 239000003480 eluent Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- CUEDLSLTSIRGCF-VQHVLOKHSA-N methyl (e)-2-(2-hydroxyphenyl)-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1O CUEDLSLTSIRGCF-VQHVLOKHSA-N 0.000 description 3
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GWEIYKFDYAMAQP-UHFFFAOYSA-M sodium;phenol;phenoxide Chemical compound [Na+].OC1=CC=CC=C1.[O-]C1=CC=CC=C1 GWEIYKFDYAMAQP-UHFFFAOYSA-M 0.000 description 1
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- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D239/52—Two oxygen 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898903019A GB8903019D0 (en) | 1989-02-10 | 1989-02-10 | Fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD291997A5 true DD291997A5 (de) | 1991-07-18 |
Family
ID=10651469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90337681A DD291997A5 (de) | 1989-02-10 | 1990-02-08 | Verfahren zur herstellung von propensaeurederivaten |
Country Status (33)
| Country | Link |
|---|---|
| EP (1) | EP0382375B1 (cs) |
| JP (1) | JPH0672140B2 (cs) |
| KR (1) | KR0120741B1 (cs) |
| CN (1) | CN1023600C (cs) |
| AP (1) | AP126A (cs) |
| AT (1) | ATE103278T1 (cs) |
| AU (1) | AU625501B2 (cs) |
| BG (1) | BG61668B2 (cs) |
| BR (1) | BR9000591A (cs) |
| CA (1) | CA2008701C (cs) |
| CZ (1) | CZ282265B6 (cs) |
| DD (1) | DD291997A5 (cs) |
| DE (3) | DE69007507T2 (cs) |
| DK (1) | DK0382375T3 (cs) |
| EG (1) | EG19307A (cs) |
| ES (1) | ES2063253T3 (cs) |
| GB (2) | GB8903019D0 (cs) |
| HU (1) | HU204798B (cs) |
| IE (1) | IE66312B1 (cs) |
| IL (1) | IL93199A (cs) |
| LT (2) | LTIP868A (cs) |
| LU (1) | LU91197I2 (cs) |
| LV (1) | LV10018B (cs) |
| MD (1) | MD1006C2 (cs) |
| MY (1) | MY105613A (cs) |
| NL (3) | NL971016I2 (cs) |
| NZ (1) | NZ232275A (cs) |
| PL (2) | PL286250A1 (cs) |
| PT (1) | PT93089B (cs) |
| RU (2) | RU2019543C1 (cs) |
| SK (1) | SK43090A3 (cs) |
| TR (1) | TR27525A (cs) |
| ZA (1) | ZA90687B (cs) |
Families Citing this family (113)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8908875D0 (en) * | 1989-04-19 | 1989-06-07 | Ici Plc | Fungicides |
| GB9016783D0 (en) * | 1989-09-01 | 1990-09-12 | Ici Plc | Agrochemical compositions |
| IE74711B1 (en) | 1990-07-27 | 1997-07-30 | Ici Plc | Fungicides |
| GB9016584D0 (en) * | 1990-07-27 | 1990-09-12 | Ici Plc | Fungicides |
| TR25727A (tr) * | 1990-11-16 | 1993-09-01 | Ici Plc | Fenoksipirimidin bilesiklerini hazirlamaya mahsus yöntem. |
| GB9122430D0 (en) * | 1990-11-16 | 1991-12-04 | Ici Plc | Chemical process |
| US5760250A (en) * | 1991-11-05 | 1998-06-02 | Zeneca Limited | Process for the preparation of 3-(α-methoxy)methylenebenzofuranones and intermediates therefor |
| US6235887B1 (en) | 1991-11-26 | 2001-05-22 | Isis Pharmaceuticals, Inc. | Enhanced triple-helix and double-helix formation directed by oligonucleotides containing modified pyrimidines |
| GB9210830D0 (en) * | 1992-05-21 | 1992-07-08 | Ici Plc | Fungicidial composition |
| TW234077B (cs) * | 1992-07-17 | 1994-11-11 | Shell Internat Res Schappej B V | |
| GB9305039D0 (en) * | 1993-03-11 | 1993-04-28 | Zeneca Ltd | Herbicidal composition |
| GB9307247D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Fungicidal compounds |
| US5436248A (en) * | 1993-07-02 | 1995-07-25 | Ciba-Geigy Corporation | Microbicides |
| DK0648417T3 (da) * | 1993-09-24 | 1996-12-23 | Basf Ag | Fungicide blandinger |
| JP3307026B2 (ja) * | 1993-11-04 | 2002-07-24 | 住友化学工業株式会社 | 農園芸用殺菌組成物 |
| DE4340181A1 (de) * | 1993-11-25 | 1995-06-01 | Bayer Ag | 3-Methoxy-2-phenyl-acrylsäuremethylester |
| GB9404375D0 (en) * | 1994-03-07 | 1994-04-20 | Zeneca Ltd | Fungicides |
| DE4426753A1 (de) | 1994-07-28 | 1996-02-01 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| RU2146675C1 (ru) * | 1994-09-26 | 2000-03-20 | Дайити Фармасьютикал Ко., Лтд. | Производные пиримидинилпиразола и противоопухолевое средство |
| IL115899A (en) * | 1994-11-17 | 2002-07-25 | Basf Aktiengesellshaft | History of Acid-2 [(2-alkoxy-6-trifluoromethyl-pyrimidine-4-yl) oxymethylene] -phenylate, their preparation, preparations for the control of animal and fungal pests containing these histories and a number of their intermediates |
| DE4444911A1 (de) * | 1994-12-16 | 1996-06-27 | Basf Ag | Fungizide Mischung |
| DE19522712A1 (de) * | 1995-06-22 | 1997-01-02 | Basf Ag | Lagerstabile, wäßrige Fungizid-Formulierung |
| TW318777B (cs) * | 1995-06-29 | 1997-11-01 | Novartis Ag | |
| DK0844823T3 (da) * | 1995-08-17 | 2002-03-04 | Basf Ag | Fungicide blandinger |
| TW384208B (en) * | 1995-09-22 | 2000-03-11 | Basf Ag | Compositions and methods for controlling harmful fungi |
| TW401275B (en) * | 1995-09-25 | 2000-08-11 | Basf Ag | Compositions and methods of controlling harmful fungi |
| IL124612A0 (en) * | 1995-12-14 | 1998-12-06 | Basf Ag | 2-O- [pyrimidin-4-yl] methyleneoxy) phenylacetic acid derivatives and their use for controlling harmful fungi and animal pests |
| DE19602095A1 (de) * | 1996-01-22 | 1997-07-24 | Bayer Ag | Halogenpyrimidine |
| SG63694A1 (en) * | 1996-03-07 | 1999-03-30 | American Cyanamid Co | Process for the preparation of unsymmetrical 4,6-bis (aryloxy) pyrimidine compounds |
| DE19623061A1 (de) * | 1996-06-10 | 1997-12-11 | Bayer Ag | Aryloxyacrylsäureester |
| GB9622345D0 (en) * | 1996-10-28 | 1997-01-08 | Zeneca Ltd | Chemical process |
| DE19710609A1 (de) | 1997-03-14 | 1998-09-17 | Bayer Ag | Substituierte Aminosalicylsäureamide |
| EP1009235A1 (de) | 1997-06-04 | 2000-06-21 | Basf Aktiengesellschaft | Fungizide mischungen |
| US5883104A (en) * | 1997-06-12 | 1999-03-16 | American Cyanamid Company | Methods for improving the residual control of mites and prolonging the protection of plants from mites infestations |
| EP0897664A1 (fr) * | 1997-08-22 | 1999-02-24 | Chimac-Agriphar S.A. | Composition fongicide |
| US5849910A (en) * | 1997-09-05 | 1998-12-15 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis aryloxy-pyrimidine compounds |
| WO1999063820A1 (fr) * | 1998-06-11 | 1999-12-16 | Shionogi & Co., Ltd. | Compositions bactericides utilisees en agriculture et horticulture et contenant de l'acide silicique et/ou du silicate de potassium |
| KR20010079852A (ko) * | 1998-09-16 | 2001-08-22 | 케네쓰 엘. 로에르트셔 | 살진균제로서 피리딘 환 상에 5원 헤테로사이클릭 환을갖는 2-메톡시이미노-2-(피리디닐옥시메틸)페닐아세트아미드 |
| EP0986965A1 (en) * | 1998-09-18 | 2000-03-22 | Janssen Pharmaceutica N.V. | Antifungal food coatings |
| WO2001035738A2 (en) | 1999-11-18 | 2001-05-25 | Basf Corporation | Non-aqueous concentrated spreading oil composition |
| GB0010198D0 (en) * | 2000-04-26 | 2000-06-14 | Novartis Ag | Organic compounds |
| IT1318599B1 (it) * | 2000-06-28 | 2003-08-27 | Alfredo Martini | Impiego di azossistrobina come conservante di prodotti alimentari. |
| JP4581102B2 (ja) * | 2000-12-05 | 2010-11-17 | クミアイ化学工業株式会社 | ストロビルリン系殺菌剤の効力増強剤及びその方法。 |
| US7687434B2 (en) | 2000-12-22 | 2010-03-30 | Monsanto Technology, Llc | Method of improving yield and vigor of plants |
| DE10140269A1 (de) | 2001-08-16 | 2003-02-27 | Degussa | Verfahren zur Herstellung von 4,6-Dihydroxypyrimidin |
| ATE404058T1 (de) | 2002-11-12 | 2008-08-15 | Basf Se | Verfahren zur ertragssteigerung bei glyphosate resistenten leguminosen |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| UA85690C2 (ru) | 2003-11-07 | 2009-02-25 | Басф Акциенгезелльшафт | Смесь для применения в сельском хозяйстве, содержащая стробилурин и модулятор этилена, способ обработки и борьбы с инфекциями в бобовых культурах |
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| EA010432B1 (ru) * | 2004-06-17 | 2008-08-29 | Басф Акциенгезельшафт | Применение (е)-5-(4-хлорбензилиден)-2,2-диметил-1-(1н-1,2,4-триазол-1-илметил)циклопентанола для борьбы со ржавчиной на растениях сои |
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| DE102005015850A1 (de) | 2005-04-07 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| ATE484194T1 (de) | 2005-06-09 | 2010-10-15 | Bayer Cropscience Ag | Wirkstoffkombinationen |
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| JP2017538860A (ja) | 2014-10-24 | 2017-12-28 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 固体粒子の表面荷電を改変するための、非両性の四級化可能な水溶性ポリマー |
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| JPS608203A (ja) * | 1983-06-29 | 1985-01-17 | Mitsui Toatsu Chem Inc | ピリミジン誘導体を有効成分とする農園芸用殺菌剤 |
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| GB8620251D0 (en) * | 1986-08-20 | 1986-10-01 | Ici Plc | Fungicides |
-
1989
- 1989-02-10 GB GB898903019A patent/GB8903019D0/en active Pending
-
1990
- 1990-01-24 IE IE27290A patent/IE66312B1/en not_active IP Right Cessation
- 1990-01-25 DE DE69007507T patent/DE69007507T2/de not_active Expired - Lifetime
- 1990-01-25 ES ES90300779T patent/ES2063253T3/es not_active Expired - Lifetime
- 1990-01-25 AT AT90300779T patent/ATE103278T1/de active
- 1990-01-25 DE DE122006000030C patent/DE122006000030I2/de active Active
- 1990-01-25 EP EP90300779A patent/EP0382375B1/en not_active Expired - Lifetime
- 1990-01-25 DE DE122006000031C patent/DE122006000031I2/de active Active
- 1990-01-25 DK DK90300779.7T patent/DK0382375T3/da active
- 1990-01-26 CA CA002008701A patent/CA2008701C/en not_active Expired - Lifetime
- 1990-01-29 IL IL9319990A patent/IL93199A/en not_active IP Right Cessation
- 1990-01-29 NZ NZ232275A patent/NZ232275A/xx unknown
- 1990-01-30 CZ CS90430A patent/CZ282265B6/cs not_active IP Right Cessation
- 1990-01-30 SK SK430-90A patent/SK43090A3/sk not_active IP Right Cessation
- 1990-01-30 ZA ZA90687A patent/ZA90687B/xx unknown
- 1990-02-02 AU AU49052/90A patent/AU625501B2/en not_active Expired
- 1990-02-05 AP APAP/P/1990/000162A patent/AP126A/en active
- 1990-02-05 GB GB909002538A patent/GB9002538D0/en active Pending
- 1990-02-07 MY MYPI90000190A patent/MY105613A/en unknown
- 1990-02-07 HU HU90690A patent/HU204798B/hu active Protection Beyond IP Right Term
- 1990-02-08 PT PT93089A patent/PT93089B/pt not_active IP Right Cessation
- 1990-02-08 DD DD90337681A patent/DD291997A5/de not_active IP Right Cessation
- 1990-02-09 PL PL28625090A patent/PL286250A1/xx unknown
- 1990-02-09 JP JP2028579A patent/JPH0672140B2/ja not_active Expired - Lifetime
- 1990-02-09 PL PL1990283723A patent/PL161278B1/pl unknown
- 1990-02-09 TR TR00162/90A patent/TR27525A/xx unknown
- 1990-02-09 RU SU904743177A patent/RU2019543C1/ru active
- 1990-02-09 BR BR909000591A patent/BR9000591A/pt not_active IP Right Cessation
- 1990-02-10 CN CN90101175A patent/CN1023600C/zh not_active Expired - Lifetime
- 1990-02-10 KR KR1019900001617A patent/KR0120741B1/ko not_active Expired - Lifetime
- 1990-02-11 EG EG6890A patent/EG19307A/xx active
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1992
- 1992-09-30 RU SU925052834A patent/RU2043990C1/ru active
- 1992-12-01 LV LVP-92-236A patent/LV10018B/en unknown
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1993
- 1993-08-17 LT LTIP868A patent/LTIP868A/xx not_active Application Discontinuation
- 1993-08-26 BG BG098073A patent/BG61668B2/bg unknown
- 1993-09-03 LT LTIP934A patent/LT3767B/lt not_active IP Right Cessation
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1994
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1997
- 1997-07-18 NL NL971016C patent/NL971016I2/nl unknown
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2005
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2006
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2009
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