HRP20100538T1 - 5,6-dialkil-7-aminotriazolopirimidini, postupci za njihovo dobijanje, njihova primjena za kontrolu patogenih gljiva, kao i sredstva koja sadrže spomenute spojeve - Google Patents
5,6-dialkil-7-aminotriazolopirimidini, postupci za njihovo dobijanje, njihova primjena za kontrolu patogenih gljiva, kao i sredstva koja sadrže spomenute spojeve Download PDFInfo
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- HRP20100538T1 HRP20100538T1 HR20100538T HRP20100538T HRP20100538T1 HR P20100538 T1 HRP20100538 T1 HR P20100538T1 HR 20100538 T HR20100538 T HR 20100538T HR P20100538 T HRP20100538 T HR P20100538T HR P20100538 T1 HRP20100538 T1 HR P20100538T1
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- Prior art keywords
- formula
- ethyl
- ylamine
- triazolo
- pyrimidin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 10
- 244000053095 fungal pathogen Species 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- -1 nitro, hydroxy Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- SZZRPOJEYIRJAY-UHFFFAOYSA-N 5-ethyl-6-(3,5,5-trimethylhexyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCC(C)CC(C)(C)C)C(CC)=NC2=NC=NN21 SZZRPOJEYIRJAY-UHFFFAOYSA-N 0.000 claims 1
- APROKQPQKHPAHO-UHFFFAOYSA-N 5-ethyl-6-(3-pentoxypropyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCOCCCCC)C(CC)=NC2=NC=NN21 APROKQPQKHPAHO-UHFFFAOYSA-N 0.000 claims 1
- MYSOIJJLHFVDAP-UHFFFAOYSA-N 5-ethyl-6-heptyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCC)C(CC)=NC2=NC=NN21 MYSOIJJLHFVDAP-UHFFFAOYSA-N 0.000 claims 1
- WEBMREWMBNRBPW-UHFFFAOYSA-N 5-ethyl-6-hexyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCC)C(CC)=NC2=NC=NN21 WEBMREWMBNRBPW-UHFFFAOYSA-N 0.000 claims 1
- ZTBSTQCAQVYVER-UHFFFAOYSA-N 5-ethyl-6-nonyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCCCC)C(CC)=NC2=NC=NN21 ZTBSTQCAQVYVER-UHFFFAOYSA-N 0.000 claims 1
- BTNOLXJGXZRUPN-UHFFFAOYSA-N 5-ethyl-6-octan-2-yl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(C(C)CCCCCC)C(CC)=NC2=NC=NN21 BTNOLXJGXZRUPN-UHFFFAOYSA-N 0.000 claims 1
- PIELEZTYUJSLSP-UHFFFAOYSA-N 5-ethyl-6-pentyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCC)C(CC)=NC2=NC=NN21 PIELEZTYUJSLSP-UHFFFAOYSA-N 0.000 claims 1
- VZPSVWCBFLVGJD-UHFFFAOYSA-N 5-ethyl-6-undecyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCCCCCC)C(CC)=NC2=NC=NN21 VZPSVWCBFLVGJD-UHFFFAOYSA-N 0.000 claims 1
- OEEYCNOOAHGFHL-UHFFFAOYSA-N 8-azahypoxanthine Chemical class O=C1N=CN=C2NNN=C12 OEEYCNOOAHGFHL-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 150000001264 acyl cyanides Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
- GGKQIOFASHYUJZ-UHFFFAOYSA-N ametoctradin Chemical compound NC1=C(CCCCCCCC)C(CC)=NC2=NC=NN21 GGKQIOFASHYUJZ-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000000417 fungicide Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
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
- 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 Condensed Heterocyclic Rings (AREA)
- Catching Or Destruction (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Triazolopirimidini formule Inaznačeni time, što supstituenti imaju slijedeće značenje: R1 je C5-C12-alkil ili C5-C14-alkoksialkil, pri čemu alifatične grupe mogu biti supstituirane sa jednom do tri slijedeće grupe: cijano, nitro, hidroksi, C3-C6-cikloalkil, C1-C6-alkiltio i NRaRb;Ra, Rb su vodik ili C1-C6-alkil; R2 je etil, CH=CH2 ili CH2CH=CH2.Patent sadrži još 9 patentnih zahtjeva.
Claims (10)
1. Triazolopirimidini formule I
[image]
naznačeni time, što supstituenti imaju slijedeće značenje:
R1 je C5-C12-alkil ili C5-C14-alkoksialkil, pri čemu alifatične grupe mogu biti supstituirane sa jednom do tri slijedeće grupe:
cijano, nitro, hidroksi, C3-C6-cikloalkil, C1-C6-alkiltio i NRaRb;
Ra, Rb su vodik ili C1-C6-alkil;
R2 je etil, CH=CH2 ili CH2CH=CH2.
2. Spojevi formule I prema zahtjevu 1, naznačeni time, što R2 označava etil.
3. Spojevi formule I prema zahtjevu 1, naznačeni time, što R1 označava nesupstituirani, nerazgranati ili jednostruko, dvostruko ili trostruko razgranati alkilni lanac sa do 12 atoma ugljika.
4. Triazolopirimidini formule I prema zahtjevu 1 naznačeni time, što su izabrani iz grupe koja sadrži:
5-etil-6-(1-metil-heptil)-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-oktil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-(3,5,5-trimetil-heksil)-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-pentil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-heksil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-heptil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-nonil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-undecil-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin;
5-etil-6-(3-pentiloksi-propil)-[1,2,4]triazolo[1,5-a]pirimidin-7-ilamin.
5. Postupak za dobijanje spojeva formule I prema jednom od zahtjeva 1 do 4, naznačen time, što β-keto ester formule II,
[image]
u kojoj R označava C1-C4-alkil, reagira sa 3-amino-1,2,4-triazolom formule III
[image]
u 7-hidroksitriazolopirimidine formule IV
[image]
koji se halogenira u spojeve formule V,
[image]
u kojoj Hal označava klor ili brom, a zatim V reagira sa amonijakom.
6. Spojevi formula IV i V, naznačeni time, što su u skladu sa zahtjevom 5.
7. Postupak za dobijanje spojeva formule I prema jednom od zahtjeva 1 do 4, naznačen time, što acilcijanidi formule VI
[image]
reagiraju sa 3-amino-1,2,4-triazolom formule III prema zahtjevu 5.
8. Fungicidno sredstvo, naznačeno time, što sadrži čvrsti ili tekući nosač i spoj formule I prema jednom od zahtjeva 1 do 4.
9. Sjeme naznačeno time, što sadrži spoj formule I prema jednom od zahtjeva 1 do 4 u količini od 1 do na .
10. Postupak za kontrolu fitopatogenih štetnih gljiva, naznačen time, što se gljive ili materijali, biljke, tlo ili sjeme koje treba zaštititi od gljivične zaraze, tretiraju sa djelotvornom količinom spojeva formule I prema jednom od zahtjeva 1 do 4.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004012011 | 2004-03-10 | ||
PCT/EP2005/002427 WO2005087773A1 (de) | 2004-03-10 | 2005-03-08 | 5,6-dialkyl-7-amino-triazolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20100538T1 true HRP20100538T1 (hr) | 2010-12-31 |
Family
ID=34961570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20100538T HRP20100538T1 (hr) | 2004-03-10 | 2010-10-04 | 5,6-dialkil-7-aminotriazolopirimidini, postupci za njihovo dobijanje, njihova primjena za kontrolu patogenih gljiva, kao i sredstva koja sadrže spomenute spojeve |
Country Status (33)
Country | Link |
---|---|
US (1) | US9487519B2 (hr) |
EP (1) | EP1725561B1 (hr) |
JP (2) | JP5005528B2 (hr) |
KR (1) | KR101306446B1 (hr) |
CN (1) | CN1930166B (hr) |
AP (1) | AP2264A (hr) |
AR (1) | AR048813A1 (hr) |
AT (1) | ATE473228T1 (hr) |
AU (1) | AU2005221808B8 (hr) |
BR (1) | BRPI0508281B1 (hr) |
CA (1) | CA2557781C (hr) |
CR (1) | CR8551A (hr) |
DE (1) | DE502005009862D1 (hr) |
DK (1) | DK1725561T3 (hr) |
EA (1) | EA010411B1 (hr) |
EC (1) | ECSP066829A (hr) |
EG (1) | EG24617A (hr) |
ES (1) | ES2347664T3 (hr) |
HR (1) | HRP20100538T1 (hr) |
IL (1) | IL177361A (hr) |
MA (1) | MA28523B1 (hr) |
NO (1) | NO20064133L (hr) |
NZ (1) | NZ549218A (hr) |
PE (1) | PE20051137A1 (hr) |
PL (1) | PL1725561T3 (hr) |
PT (1) | PT1725561E (hr) |
RS (1) | RS51454B (hr) |
SI (1) | SI1725561T1 (hr) |
TW (1) | TWI348354B (hr) |
UA (1) | UA81873C2 (hr) |
UY (1) | UY28800A1 (hr) |
WO (1) | WO2005087773A1 (hr) |
ZA (1) | ZA200608384B (hr) |
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JP4550105B2 (ja) * | 2004-03-10 | 2010-09-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 5,6−ジアルキル−7−アミノトリアゾロピリミジン、その調製、および有害真菌類を防除するためのその使用、ならびにそれらの化合物を含む組成物 |
EA009883B1 (ru) * | 2004-03-10 | 2008-04-28 | Басф Акциенгезельшафт | 5, 6-диалкил-7-амино-триазолопиримидины, способ их получения и их применение для борьбы с патогенными растениями, а также содержащие их средства |
RS51454B (en) * | 2004-03-10 | 2011-04-30 | Basf Se | 5,6-DIALKYL-7-AMINOTRIAZOLOPYRIMIDINES, PROCEDURES FOR THEIR PREPARATION, THEIR APPLICATION FOR THE CONTROL OF PATHOGENIC Fungi, AND THE MEANS CONTAINING THESE COMPOUNDS |
CN101128465A (zh) * | 2005-03-01 | 2008-02-20 | 巴斯福股份公司 | 5,6-二烷基-7-氨基唑并嘧啶、其制备方法及其在防治病原性真菌中的用途以及包含这些化合物的组合物 |
EP1856121A1 (de) * | 2005-03-01 | 2007-11-21 | Basf Aktiengesellschaft | 5,6-dialkyl-7-amino-azolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
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DE1620694C3 (de) * | 1966-10-03 | 1982-04-15 | VEB Deutsches Hydrierwerk Rodleben, DDR 4501 Rodleben | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren |
DE3338292A1 (de) * | 1983-10-21 | 1985-05-02 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)-pyrimidine und diese enthaltende fungizide |
DE3533050A1 (de) * | 1985-09-17 | 1987-03-26 | Basf Ag | 7-amino-azolo(1,5-a)pyrimidine, verfahren zu ihrer herstellung und diese enthaltende fungizide, bzw. deren verwendung als fungizide |
EP0614113B1 (en) * | 1993-02-22 | 1999-08-11 | Mitsubishi Paper Mills, Ltd. | Silver halide photographic photosensitive material |
TW258648B (hr) * | 1993-03-04 | 1995-10-01 | Shell Internat Res Schappej Bv | |
IL108747A (en) * | 1993-03-04 | 1999-03-12 | Shell Int Research | Mushroom-killing preparations containing a history of 6 metamorphoses of 5 - 7 Dihalo - 1, 2 - 4 Triazlo [A-1,5] Pyrimidine Certain such new compounds and their preparation |
RU2147584C1 (ru) * | 1995-10-27 | 2000-04-20 | Американ Цианамид Компани | Способ получения дигалоидазолопиримидинов и способ получения дигидроксиазолопиримидинов |
DK1414302T3 (da) | 2001-07-26 | 2007-06-18 | Basf Ag | 7-aminotriazolopyrimidiner til bekæmpelse af skadelige svampe |
RS51454B (en) * | 2004-03-10 | 2011-04-30 | Basf Se | 5,6-DIALKYL-7-AMINOTRIAZOLOPYRIMIDINES, PROCEDURES FOR THEIR PREPARATION, THEIR APPLICATION FOR THE CONTROL OF PATHOGENIC Fungi, AND THE MEANS CONTAINING THESE COMPOUNDS |
BRPI0508330A (pt) * | 2004-03-10 | 2007-07-24 | Basf Ag | composto, processo para a preparação de compostos, composição fungicida, semente, e, método para controlar fungos fitopatogênicos nocivos |
JP4550105B2 (ja) * | 2004-03-10 | 2010-09-22 | ビーエーエスエフ ソシエタス・ヨーロピア | 5,6−ジアルキル−7−アミノトリアゾロピリミジン、その調製、および有害真菌類を防除するためのその使用、ならびにそれらの化合物を含む組成物 |
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