DE3783669T2 - Alpha-aryl-alpha-phenethyl-1h-1,2,4-triazol-1-propan-nitrile. - Google Patents
Alpha-aryl-alpha-phenethyl-1h-1,2,4-triazol-1-propan-nitrile.Info
- Publication number
- DE3783669T2 DE3783669T2 DE8787305808T DE3783669T DE3783669T2 DE 3783669 T2 DE3783669 T2 DE 3783669T2 DE 8787305808 T DE8787305808 T DE 8787305808T DE 3783669 T DE3783669 T DE 3783669T DE 3783669 T2 DE3783669 T2 DE 3783669T2
- Authority
- DE
- Germany
- Prior art keywords
- alpha
- halogen
- ethyl
- triazole
- propanenitrile
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 56
- -1 ethenylene radical Chemical class 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 150000003852 triazoles Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 230000000855 fungicidal effect Effects 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229910052757 nitrogen 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
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- NRWBGOUOOZPRFA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methoxyphenyl)-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound COC1=CC=CC=C1C(C#N)(CN1N=CN=C1)CCC1=CC=C(Cl)C=C1 NRWBGOUOOZPRFA-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- ZFNHNQUQCOYXJR-UHFFFAOYSA-N 2-(4-bromophenyl)-4-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC(Br)=CC=1)(C#N)CN1N=CN=C1 ZFNHNQUQCOYXJR-UHFFFAOYSA-N 0.000 claims description 2
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 150000005840 aryl radicals Chemical group 0.000 claims 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- HQYJUFZPQLLYCK-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C(=CC=CC=1)Cl)(C#N)CN1N=CN=C1 HQYJUFZPQLLYCK-UHFFFAOYSA-N 0.000 claims 1
- YILZKDVXMHFCIA-UHFFFAOYSA-N 2-phenyl-2-(1,2,4-triazol-1-ylmethyl)-4-[4-(trifluoromethyl)phenyl]butanenitrile Chemical compound C1=CC(C(F)(F)F)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 YILZKDVXMHFCIA-UHFFFAOYSA-N 0.000 claims 1
- TXLYPTJRLHEVIG-UHFFFAOYSA-N 4-(3-bromophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound BrC1=CC=CC(CCC(CN2N=CN=C2)(C#N)C=2C=CC=CC=2)=C1 TXLYPTJRLHEVIG-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
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- 238000012360 testing method Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 20
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 16
- 239000000417 fungicide Substances 0.000 description 15
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
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- 238000001030 gas--liquid chromatography Methods 0.000 description 13
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- 241000209219 Hordeum Species 0.000 description 11
- 235000007340 Hordeum vulgare Nutrition 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 239000002054 inoculum Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 241000209094 Oryza Species 0.000 description 9
- 239000002689 soil Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- DSXJKFCLGZTRDG-UHFFFAOYSA-N 4-(2-phenylethyl)-2h-triazole Chemical class C=1NN=NC=1CCC1=CC=CC=C1 DSXJKFCLGZTRDG-UHFFFAOYSA-N 0.000 description 8
- BJGPDVPEEFEDIA-UHFFFAOYSA-N 4-(chloromethyl)-2h-triazole Chemical compound ClCC1=CNN=N1 BJGPDVPEEFEDIA-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- MQXUINLVWYNNJE-UHFFFAOYSA-N potassium;2h-triazole Chemical compound [K].C=1C=NNN=1 MQXUINLVWYNNJE-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
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- 150000001450 anions Chemical group 0.000 description 7
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 125000001475 halogen functional group Chemical group 0.000 description 7
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 3
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- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88099086A | 1986-07-02 | 1986-07-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3783669D1 DE3783669D1 (de) | 1993-03-04 |
| DE3783669T2 true DE3783669T2 (de) | 1993-08-05 |
Family
ID=25377550
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787305808T Expired - Fee Related DE3783669T2 (de) | 1986-07-02 | 1987-07-01 | Alpha-aryl-alpha-phenethyl-1h-1,2,4-triazol-1-propan-nitrile. |
| DE19873721786 Withdrawn DE3721786A1 (de) | 1986-07-02 | 1987-07-01 | Fungizide verbindung, verfahren zu ihrer herstellung und diese enthaltende mittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19873721786 Withdrawn DE3721786A1 (de) | 1986-07-02 | 1987-07-01 | Fungizide verbindung, verfahren zu ihrer herstellung und diese enthaltende mittel |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0251775B1 (en]) |
| JP (1) | JPH0655729B2 (en]) |
| KR (1) | KR950003999B1 (en]) |
| AR (1) | AR245448A1 (en]) |
| AT (1) | ATE84789T1 (en]) |
| AU (1) | AU607425B2 (en]) |
| BE (1) | BE1001485A4 (en]) |
| BR (1) | BR8703376A (en]) |
| CA (1) | CA1321588C (en]) |
| DE (2) | DE3783669T2 (en]) |
| DK (2) | DK171399B1 (en]) |
| EG (1) | EG18875A (en]) |
| ES (1) | ES2053542T3 (en]) |
| FR (1) | FR2612741A1 (en]) |
| GB (2) | GB2192184B (en]) |
| GR (1) | GR3006830T3 (en]) |
| HU (1) | HU203452B (en]) |
| IE (1) | IE60314B1 (en]) |
| IL (1) | IL83034A (en]) |
| IT (1) | IT1211468B (en]) |
| NZ (1) | NZ220916A (en]) |
| PT (1) | PT85239B (en]) |
| TR (1) | TR23322A (en]) |
| ZA (1) | ZA874751B (en]) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3825841A1 (de) * | 1988-07-29 | 1990-02-01 | Basf Ag | 1-halogen-1-azolypropene und -methyloxirane und diese enthaltende fungizide |
| DE3835742A1 (de) * | 1988-10-20 | 1990-05-10 | Lentia Gmbh | Neue nitroalkylazole |
| CA2037162A1 (en) * | 1990-03-12 | 1991-09-13 | Steven Howard Shaber | Heterocyclicacetonitriles and fungicidal use |
| ZA914221B (en) | 1990-06-05 | 1992-03-25 | Ciba Geigy | Aromatic compounds |
| CH680895A5 (en]) * | 1990-11-02 | 1992-12-15 | Ciba Geigy Ag | |
| US5330984A (en) * | 1990-11-02 | 1994-07-19 | Ciba-Geigy Corporation | Fungicidal compositions |
| US5223178A (en) * | 1990-12-10 | 1993-06-29 | Rohm And Haas Company | Use of certain triazoles to protect materials from fungal attack, articles and compositions |
| US5240925A (en) * | 1991-08-26 | 1993-08-31 | Rohm And Haas Company | Fungicidal 2-aryl-2-cyano-2-(heterocyclylalkyl)ethyl-1,2,4-triazoles |
| CA2076203A1 (en) * | 1991-08-26 | 1993-02-27 | Steven Howard Shaber | Fungicidal 2-aryl-2-cyano-2-(aryloxyalkyl) ethyl-1,2,4-triazoles |
| GB9125791D0 (en) * | 1991-12-04 | 1992-02-05 | Schering Agrochemicals Ltd | Herbicides |
| ES2086716T3 (es) * | 1991-12-19 | 1996-07-01 | Ciba Geigy Ag | Microbicidas. |
| DE59307717D1 (de) * | 1992-02-13 | 1998-01-08 | Ciba Geigy Ag | Fungizide Mischungen auf der Basis von Triazol-Fungiziden und 4,6-Dimethyl-N-Phenyl-2-Pyrimidinamin |
| US5342980A (en) | 1992-12-30 | 1994-08-30 | American Cyanamid Company | Fungicidal agents |
| DE59400216D1 (de) * | 1993-09-24 | 1996-05-23 | Basf Ag | Fungizide Mischungen |
| TW286264B (en]) * | 1994-05-20 | 1996-09-21 | Ciba Geigy Ag | |
| US5510493A (en) * | 1994-11-14 | 1996-04-23 | Rohm And Haas Company | Process for alkylation with triazoles |
| IT1296926B1 (it) * | 1997-12-05 | 1999-08-03 | Zambon Spa | Procedimento per la preparazione di composti ad attivita' antimicotica |
| ES2197124T3 (es) * | 1999-12-13 | 2004-01-01 | Bayer Cropscience Ag | Combinaciones de productos activos fungicidas. |
| KR100417082B1 (ko) * | 1999-12-22 | 2004-02-05 | 주식회사 포스코 | 연속 계량 장치의 이상 검출 장치 및 방법 |
| 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 |
| EA201270781A1 (ru) | 2005-06-09 | 2013-09-30 | Байер Кропсайенс Аг | Комбинации биологически активных веществ |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005035300A1 (de) | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| EP2000028A1 (de) | 2007-06-06 | 2008-12-10 | Bayer CropScience Aktiengesellschaft | Fungizide Wirkstoffkombinationen |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| WO2010149758A1 (en) | 2009-06-25 | 2010-12-29 | Basf Se | Antifungal 1, 2, 4-triazolyl derivatives |
| EP2453750A2 (de) | 2009-07-16 | 2012-05-23 | Bayer CropScience AG | Synergistische wirkstoffkombinationen mit phenyltriazolen |
| CN102057930B (zh) * | 2011-01-24 | 2014-03-19 | 陕西美邦农药有限公司 | 一种含有腈苯唑与硫代氨基甲酸酯类化合物的杀菌组合物 |
| EP2746255A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2746264A1 (en) | 2012-12-19 | 2014-06-25 | Basf Se | Substituted [1,2,4]triazole and imidazole compounds |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| CN114467960A (zh) * | 2022-02-09 | 2022-05-13 | 陕西上格之路生物科学有限公司 | 一种含有腈苯唑和硫酸铜钙的杀菌组合物 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2181580A1 (en) * | 1972-04-28 | 1973-12-07 | Stampfli Jackie | Disposable syringe - with device for preventing its re-use |
| US3951146A (en) * | 1972-11-01 | 1976-04-20 | Arias Marcelo Chiquiar | Disposable self-destructible syringes which render themselves unreusable |
| US4073921A (en) * | 1975-03-12 | 1978-02-14 | Rohm And Haas Company | Substituted arylcyanoalkyl and diarylcyanoalkylimidazoles and fungical compositions and methods utilizing them |
| US4366165A (en) * | 1977-05-19 | 1982-12-28 | Rohm And Haas Company | 1 and 4-Arylcyanoalkyl-1,2,4-triazoles and fungicidal use |
| CH620126A5 (en]) * | 1978-03-10 | 1980-11-14 | Tulcea Sa | |
| EP0158741A3 (en) * | 1980-11-19 | 1986-02-12 | Imperial Chemical Industries Plc | Intermediates for fungicidal triazole and imidazole compounds |
| ATE16702T1 (de) * | 1981-03-10 | 1985-12-15 | Ciba Geigy Ag | Verfahren zur herstellung von phenylaethyltriazolen. |
| EP0061840A3 (en) * | 1981-03-30 | 1983-08-24 | Imperial Chemical Industries Plc | Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them |
| DE3216301A1 (de) * | 1982-04-26 | 1983-10-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,2,4-triazol-1-yl-propionitrile, verfahren zur herstellung dieser verbindungen sowie diese enthaltende biozide mittel |
| FR2571261B1 (fr) * | 1984-10-09 | 1987-01-30 | Avare Georges | Seringue du type jetable pour injection ou prelevement humain ou animal et corps de seringue afferent |
| DE8529315U1 (de) * | 1985-10-11 | 1986-04-17 | PHYSIONIC Gesellschaft für Medizin- und Systemtechnik mbH, 1000 Berlin | Medizinische und/oder technische Injektionsspritze mit Einzugsmechanismus der Injektionskanüle in den Spritzenzylinder |
-
1987
- 1987-06-23 CA CA000540296A patent/CA1321588C/en not_active Expired - Fee Related
- 1987-06-25 AR AR87307982A patent/AR245448A1/es active
- 1987-06-25 IE IE169987A patent/IE60314B1/en not_active IP Right Cessation
- 1987-06-30 DK DK336587A patent/DK171399B1/da active
- 1987-06-30 IL IL83034A patent/IL83034A/xx not_active IP Right Cessation
- 1987-06-30 DK DK336587D patent/DK336587D0/da unknown
- 1987-07-01 FR FR8709321A patent/FR2612741A1/fr not_active Withdrawn
- 1987-07-01 DE DE8787305808T patent/DE3783669T2/de not_active Expired - Fee Related
- 1987-07-01 ZA ZA874751A patent/ZA874751B/xx unknown
- 1987-07-01 JP JP62165095A patent/JPH0655729B2/ja not_active Expired - Lifetime
- 1987-07-01 EP EP87305808A patent/EP0251775B1/en not_active Expired - Lifetime
- 1987-07-01 AT AT87305808T patent/ATE84789T1/de not_active IP Right Cessation
- 1987-07-01 IT IT8767565A patent/IT1211468B/it active
- 1987-07-01 BE BE8700737A patent/BE1001485A4/fr not_active IP Right Cessation
- 1987-07-01 ES ES87305808T patent/ES2053542T3/es not_active Expired - Lifetime
- 1987-07-01 DE DE19873721786 patent/DE3721786A1/de not_active Withdrawn
- 1987-07-01 NZ NZ220916A patent/NZ220916A/en unknown
- 1987-07-01 GB GB8715388A patent/GB2192184B/en not_active Revoked
- 1987-07-02 HU HU873001A patent/HU203452B/hu not_active IP Right Cessation
- 1987-07-02 PT PT85239A patent/PT85239B/pt not_active IP Right Cessation
- 1987-07-02 EG EG38887A patent/EG18875A/xx active
- 1987-07-02 TR TR469/87A patent/TR23322A/xx unknown
- 1987-07-02 BR BR8703376A patent/BR8703376A/pt not_active IP Right Cessation
- 1987-07-02 KR KR1019870007028A patent/KR950003999B1/ko not_active Expired - Fee Related
- 1987-07-02 AU AU75048/87A patent/AU607425B2/en not_active Ceased
- 1987-10-06 GB GB8723388A patent/GB2197311B/en not_active Revoked
-
1993
- 1993-01-21 GR GR920403178T patent/GR3006830T3/el unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |