DK163504B - 2-amino-4-trichlormethyl-pyridin, fremgangsmaade til dets fremstilling samt nitrifikationshaemmende middel indeholdende dette - Google Patents
2-amino-4-trichlormethyl-pyridin, fremgangsmaade til dets fremstilling samt nitrifikationshaemmende middel indeholdende dette Download PDFInfo
- Publication number
- DK163504B DK163504B DK123886A DK123886A DK163504B DK 163504 B DK163504 B DK 163504B DK 123886 A DK123886 A DK 123886A DK 123886 A DK123886 A DK 123886A DK 163504 B DK163504 B DK 163504B
- Authority
- DK
- Denmark
- Prior art keywords
- amino
- pyridine
- preparation
- nitrificant
- antificating
- Prior art date
Links
- PMPFKKHAWYLYNU-UHFFFAOYSA-N 4-(trichloromethyl)pyridin-2-amine Chemical compound NC1=CC(C(Cl)(Cl)Cl)=CC=N1 PMPFKKHAWYLYNU-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003795 chemical substances by application Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 claims description 5
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 229950011175 aminopicoline Drugs 0.000 claims description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 3
- DNJNBNSEZWBVOR-UHFFFAOYSA-N 2-(4-methylpyridin-2-yl)isoindole-1,3-dione Chemical compound CC1=CC=NC(N2C(C3=CC=CC=C3C2=O)=O)=C1 DNJNBNSEZWBVOR-UHFFFAOYSA-N 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000002689 soil Substances 0.000 description 13
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 6
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 6
- 235000011130 ammonium sulphate Nutrition 0.000 description 6
- 239000001166 ammonium sulphate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 acetone Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- OTBXSHMBMCKWDD-UHFFFAOYSA-N 2-[4-(trichloromethyl)pyridin-2-yl]isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)C1=CC=NC(N2C(C3=CC=CC=C3C2=O)=O)=C1 OTBXSHMBMCKWDD-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AWCIKBIGEVDMCI-UHFFFAOYSA-N 2,4-bis(trichloromethyl)pyridine Chemical compound ClC(Cl)(Cl)C1=CC=NC(C(Cl)(Cl)Cl)=C1 AWCIKBIGEVDMCI-UHFFFAOYSA-N 0.000 description 1
- MJPZDSDDTGJFNE-UHFFFAOYSA-N 2-(3-methylpyridin-2-yl)isoindole-1,3-dione Chemical compound CC1=CC=CN=C1N1C(=O)C2=CC=CC=C2C1=O MJPZDSDDTGJFNE-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- JYQFHKYYTOIWOQ-UHFFFAOYSA-N 4-(trichloromethyl)pyridine Chemical compound ClC(Cl)(Cl)C1=CC=NC=C1 JYQFHKYYTOIWOQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C05—FERTILISERS; MANUFACTURE THEREOF
- C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
- C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
- C05G3/90—Mixtures of one or more fertilisers with additives not having a specially fertilising activity for affecting the nitrification of ammonium compounds or urea in the soil
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P60/00—Technologies relating to agriculture, livestock or agroalimentary industries
- Y02P60/20—Reduction of greenhouse gas [GHG] emissions in agriculture, e.g. CO2
- Y02P60/21—Dinitrogen oxide [N2O], e.g. using aquaponics, hydroponics or efficiency measures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Soil Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
DK 163504B
i
Opfindelsen angår forbindelsen 2-amino-4-trichlormethyl-pyridin, en fremgangsmåde, som er ejendommelig ved det i krav 2's kendetegnende del angivne, til dets fremstilling, samt et nitrifikationshæmmende middel indeholdende 5 en aktiv mængde af forbindelsen.
4-Trichlormethylpyridin og 2,4-bis(trichlormethyl)pyridin er kendte som nitrifikationshæmmere, og er beskrevet i US patentskrift nr. 3 135 594.
10 2-Amino-4-trichlormethyl-6-halogenpyridiner er som stoffer kendte. Man tilskriver dem fungicide, baktericide og insekticide virkninger, men for ingen af stofferne fra denne gruppe, der f.eks. er beskrevet i US patentskrift 15 nr. 3 799 935, er omtalt en nitrifikationshæmmende virkning.
Det har nu overraskende vist sig, at 2-amino-4-trichlor-methylpyridin med formlen I
20 CClj U) (λ N NH, 25 2 har en særdeles god nitrifikationshæmmende virkning samt en mindre flygtighed i forhold til de nævnte 4-substitu-erede ni tri f ikationshæmmere.
30 2-Amino-4-trichlormethylpyridin kan udvindes af 2-amino-4-picolin efter passende beskyttelse af aminogruppen. Beskyttelsen af aminogruppen kan f.eks. tilvejebringes ved omsætning med phthalsyreanhydrid. Halogenering af 4-35 methyl-2-phthalimido-pyridin kan foretages med chlor til 2-phthalimido-4-trichlormethyl-pyridin uden isolering af denne i reaktionsblandingen; hvorefter beskyttelsesgrup-
DK 163504 B
2 pen igen spaltes af ved forsæbning, hvortil ethanolamin har vist sig velegnet.
Til indføring af beskyttelsesgruppen anvender man hen-5 sigtsmæssigt et opløsningsmiddel; på tale som et sådant kommer aromater såsom benzen, toluen og xylen; alifatiske carbonhydrider såvel som substituerede aromater såsom nitrobenzen og dichlorbenzen, eller andre halogenerede carbonhydrider såsom tetrachlorethan. Det dannede vand fjer-10 nes hensigtsmæssigt azeotropt. Omsætningen forløber mellem 50 og 250 °C, fortrinsvis mellem 100 og 180 °C.
Hvis halogeneringen skal forløbe uden isolering af mellemproduktet, anvender man hensigtsmæssigt et opløsnings-15 middel, der er velegnet til halogeneringen. Man foretrækker chlorbenzen og dichlorbenzen, men også f.eks. nitrobenzen. Hensigtsmæssigt tilsættes en radikaldanner, såsom azodiisosmørsyrenitril i en mængde fra 0,1 til 10%, fortrinsvis mellem 0,5 og 1%, beregnet i forhold til den 20 forbindelse, der skal chloreres. Omsætningen kan accelereres ved hjælp af en UV-lyskilde. Temperaturområdet for chloreringen ligger fra 50 til 250 °C, fortrinsvis fra 120 til 160 °C.
25 Forsæbningen foretages hensigtsmæssigt i henhold til den i DE offentliggørelsesskrift nr. 33 19 650 beskrevne metode.
Til forsæbningen kan det anbefales, at man som opløs-30 ningsmiddel anvender et overskud af ethanolamin, vand, en alkohol såsom ethanol, propanol eller methylglycol, en keton såsom acetone, et chloreret carbonhydrid såsom chloroform, eller en ether såsom diethylether. Man foretrækker et overskud af ethanolamin, ethanol og propanol.
35 Det foretrukne temperaturområde for forsæbningen ligger fra -10 °C til 30 °C.
DK 163504 B
3
EKSEMPEL
108,1 g 2-amino-4-picolin blev opvarmet til 170 °C i 1 kg 1,2-dichlorbenzen med 148 g phthalsyreanhydrid i 2 timer 5 under tilbagésvaling ved hjælp af en køler, der blev holdt på en temperatur over 100 °C, og det dannede vand blev afdestilleret. Blandingen blev afkølet til 140 "C og tilsat 1 g azodiisosmørsyrenitril. Ved 140 °C indførte man 400 g chlor, og derpå afkøledes, en del af opløs-10 ningsmidlet blev fjernet under vacuum, og remanensen blev tilsat petrolether. Bundfaldet blev separeret, vasket med petrolether og tørret. Der fremkom 320 g 2-phthalimido-4-trichlormethylpyridin (svarende til 94% af den beregnede mængde; snip. 143 °C).
15
Af forproduktet indførtes 105 g ved 20 til 30 °C i 600 g ethanolamin. Efter 30 minutter indførte man blandingen i 2 liter isvand, bundfaldet blev separeret, vasket med vand og tørret. Der fremkom 122 g 2-amino-4-trichlorme-20 thyl-pyridin (svarende til 96%; smp. 114 °C).
ANVENDELSESEKSEMPEL
Til 200 g ikke steriliseret fra friland udtaget lerholdig 25 sandjord, hvis fugtighedsindhold var indstillet til 50% af den maximale vandkapacitet, tilsattes 220 mg ammoniumsulfat og blandedes grundigt med jorden. Derpå tilsattes 2-amino-4-trichlormethylpyridin, opløst i 0,2 ml acetone, i mængder på 2, 1, 0,5 og 0,25 ppm beregnet i forhold til 30 den fugtige sandjord. Efter omhyggelig gennemblanding blev jordbundsprøverne, der efter afdampning af acetonen blev opbevaret i glasbeholdere tildækket med aluminiumfolie for at forhindre vandtab, inkuberet sammen med kontroller uden tilsætning af aktivt stof over et tidsrum på 35 28 dage ved 21 °C (efter dette tidsrum indeholdt en jord prøve af normal jordbonitet i almindelighed ingen påviselige mængder af ammonium-nitrogen).
DK 163504 B
4
Derpå indfyldtes 2,5 g jordprøver i 100 ml Erlenmeyerkol-ber, og der tilsattes 22,5 ml 0,1 n kaliumsulfat-opløs-ning. Efter 30 minutters omrystning frafiltreredes remanens, og 2,5 ml jordbundsudtræk blandedes med 1625 ml de-5 stilleret vand. Derpå tilsattes med henblik på påvisning af endnu i jordudtrækket foreliggende ammoniumioner 1,25 ml Nessler-reagens, og der omrystedes grundigt. Farveændringerne måltes derpå fotometrisk ved en bølgelængde på 420 nm. Ved hjælp af standardkurver, der var tilvejebragt 10 ved hjælp af opløsninger med kendte indhold af ammoniumsulfat, bestemte man de mængder af ammoniumsulfat, der endnu forelå i jordprøverne. Den procentvise hæmning af nitrifikationen i de behandlede jordprøver beregnedes til sammenligning med de ubehandlede jordprøver (kun am-15 moniumsulfat-tilsætning) i henhold til følgende formel: a-b % hæmning af nitrifikationen = -. 100 a 9Ω u a = nitrifikationsgrad af ammoniumsulfat (antaget at være 100% eller 1,0) b = nitrifikationsgrad af ammoniumsulfat med tilsat ni tri f ikati onshæmmer ^ Aktivt stof, % hæmning af nitrifikationen 4 uger tilsætning efter tilsætning af 2-amino-4-tri- ppm chlormethylpyridin til jorden 2 100 1 97 0,5 94 30 0,25 48 35
Claims (2)
- 2. Fremgangsmåde til fremstilling af 2-amino-4-trichlor-methylpyridin, kendetegnet ved, at man omsætter 2-amino-4-picolin med phthalsyreanhydrid til 4-methyl-2-phthalimido-pyridin, at man chlorerer dette, og at man 15 forsæber.
- 3. Nitrifikationshæmmende middel, kendetegnet ved, at det indeholder en aktiv mængde 2-amino-4-tri-chlormethylpyridin. 20 25 1 35
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3509860 | 1985-03-19 | ||
| DE19853509860 DE3509860A1 (de) | 1985-03-19 | 1985-03-19 | 2-amino-4-trichlormethyl-pyridin, verfahren zu seiner herstellung und seine verwendung als nitrifikationshemmer |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK123886D0 DK123886D0 (da) | 1986-03-18 |
| DK123886A DK123886A (da) | 1986-09-20 |
| DK163504B true DK163504B (da) | 1992-03-09 |
| DK163504C DK163504C (da) | 1992-07-27 |
Family
ID=6265674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK123886A DK163504C (da) | 1985-03-19 | 1986-03-18 | 2-amino-4-trichlormethyl-pyridin, fremgangsmaade til dets fremstilling samt nitrifikationshaemmende middel indeholdende dette |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4699983A (da) |
| EP (1) | EP0196522B1 (da) |
| JP (1) | JPS61233671A (da) |
| CA (1) | CA1254572A (da) |
| DE (2) | DE3509860A1 (da) |
| DK (1) | DK163504C (da) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4012831A1 (de) * | 1990-04-23 | 1991-10-24 | Basf Ag | 2-amino-4-trichlorpyridinderivate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3135594A (en) * | 1961-09-01 | 1964-06-02 | Dow Chemical Co | Method and product for treating soil to suppress the nitrification of ammonium nitrogen therein |
| US3787420A (en) * | 1969-03-17 | 1974-01-22 | Dow Chemical Co | Cyanoalkoxy(trifluoromethyl)pyridines |
| US3682936A (en) * | 1970-10-02 | 1972-08-08 | Dow Chemical Co | Certain 6-(trifluoromethyl)-pyridinols |
| US3799935A (en) * | 1972-10-10 | 1974-03-26 | Dow Chemical Co | Substituted aminohalo-pyridines |
| US4154835A (en) * | 1977-10-12 | 1979-05-15 | Merck & Co., Inc. | Anthelmintic imidazo [1,2-a] pyridines |
-
1985
- 1985-03-19 DE DE19853509860 patent/DE3509860A1/de not_active Withdrawn
-
1986
- 1986-03-07 JP JP61048771A patent/JPS61233671A/ja active Pending
- 1986-03-12 US US06/838,780 patent/US4699983A/en not_active Expired - Fee Related
- 1986-03-13 CA CA000504024A patent/CA1254572A/en not_active Expired
- 1986-03-14 EP EP86103458A patent/EP0196522B1/de not_active Expired
- 1986-03-14 DE DE8686103458T patent/DE3664324D1/de not_active Expired
- 1986-03-18 DK DK123886A patent/DK163504C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61233671A (ja) | 1986-10-17 |
| EP0196522B1 (de) | 1989-07-12 |
| DK163504C (da) | 1992-07-27 |
| EP0196522A1 (de) | 1986-10-08 |
| CA1254572A (en) | 1989-05-23 |
| DE3509860A1 (de) | 1986-09-25 |
| DK123886D0 (da) | 1986-03-18 |
| DE3664324D1 (en) | 1989-08-17 |
| DK123886A (da) | 1986-09-20 |
| US4699983A (en) | 1987-10-13 |
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