DE1795772A1 - Pyrimidinderivate - Google Patents

Pyrimidinderivate

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Publication number
DE1795772A1
DE1795772A1 DE19671795772 DE1795772A DE1795772A1 DE 1795772 A1 DE1795772 A1 DE 1795772A1 DE 19671795772 DE19671795772 DE 19671795772 DE 1795772 A DE1795772 A DE 1795772A DE 1795772 A1 DE1795772 A1 DE 1795772A1
Authority
DE
Germany
Prior art keywords
lower alkyl
hydroxy
dimethylamino
methyl
butyl
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.)
Granted
Application number
DE19671795772
Other languages
English (en)
Other versions
DE1795772B2 (de
DE1795772C3 (de
Inventor
Richard Stewart Elias
Peter Frank Hilary Freeman
Brian Kenneth Snell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of DE1795772A1 publication Critical patent/DE1795772A1/de
Publication of DE1795772B2 publication Critical patent/DE1795772B2/de
Application granted granted Critical
Publication of DE1795772C3 publication Critical patent/DE1795772C3/de
Granted legal-status Critical Current

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Classifications

    • 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
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • 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
    • C07D239/48—Two nitrogen atoms
    • 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
    • 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
    • C07D239/56—One oxygen atom and one sulfur atom
    • 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
    • C07D239/69—Benzenesulfonamido-pyrimidines
    • 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
    • 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
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (12)

  1. PATENTANSPRUCHS :
    und der Salze derselben, worin FL und R? für Miedrigalkyl, Jiedrigalkenyl, Niedri.^alky!phenyl, Halogenphenyl oder niedrigalkoxycarbonylsubstituiertes Phenyl, Anilino, Niedrigalkylcaroonyl, Halogen-niedrigalkylcarbonyl, ein stickstoffhaltiges nonocyclisches heterocvclisches Radikal, Phenyl-niedrigalkyl, :iiedrit-alkyl, das durch ein 6-cliedriges heterocyclischea stickstoffhaltiges Radikal substituiert ist, Cycloalkyl, Carbamoyl oder eine nitrosubstituierte Phenylsulfony!gruppe
    509836/0917
    BAD ORIGINAL
    steht; oder R1 und R~ gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden, der ein oder mehrere zusätzliche heterocyclische Atome enthalten kann, oder eine Guanidino oder -Benzylidinhydrazinogruppe bilden; R-, für Viasserstoff, Halogen, Niedrigalkyl oder Niedrigalkylthio-niedrigalkyl, steht; Rj+ für'Wasserstoff, Halogen, Niedrigalkyl, Phenyl-niedrigalkyl, Niedrigalkenyl, Niedrigalkoxyalkyl, Hydroxyhalogen-niedrigälkyl, Nitro, monocyclisch heterocyclisch substituiertes Nieürigalkyl, Phenyl, Phenyloxy oder halogen- oder niedrigalkylsubstituiertes Phenylthio, Niedrigalkylsulfonyl, pheny-niedrigalkylthio-, niedrigalkyl- oder halogensubstituiertes Phenyl-niedrigalkyl oder eine -CHO-Gruppe steht; oder R, und Rj, gemeinsam eine Niedrigalkylen- oder Niedrigalkenylenbrückengruppe bilden; X für ein Sauerstoff- oder Schwefelatom steht; und Rc für Wasserstoff, Hydroxy-niedrigalkyl, Phenyl-niedrigalkyl, Phenylcarbonyloxy-niedrigalkyl, Niedrigalkenyl, Niedrigalkoxycarbonyl-niedrigalkyl, Niedrigalkylcarbonyl-niedrigalky1, Di-niedrigalkylamino-niedrigalkyl, Niedrigalkylthio-niedrigalkyl oder Niedrigalkoxy-niedrigalkyl steht, mit der Voraussetzung, dass, wenn R^ und R? beide Methyl sind, R^ nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.
  2. 2. Pyrimidinderivate der allgemeinen Formel
    R1 R2
    509836/0917
    und die Salze derselben, worin R1 und R2 für Methyl, Äthyl, Propyl, Butyl, Allyl, Äthoxy, Carboxyphenyl, Anilino, Methylcarbonyl, Trifluoromethylcarbonyl, Chloromethylcarbonyl, Benzyl, 3-(4-Morpholino)-propyl, 2-Pyridyl, Cyclohexyl, Carbamoyl oder Nitrophenylsulfonyl steht; oder R1 und R2 gemeinsam mit dem-benachbarten Stickstoffatom Guanidino, Benzylidinhydrazino, Pyrrol, Morpholin, 4-Methylpiperazin, Piperidin oder einen Tetrazolring bilden; R- für Wasserstoff, Chloro, Methyl, Äthyl, Propyl, Hexyl, Äthylthiomethyl steht; Rh für Wasserstoff, Bromo, Niedrigalkyl, Benzyl, Ally, Butenyl, Äthoxyäthyl, Trichlorohydroxyäthyl, Nitro, Piperid-1-ylir.ethyl, Phenyl, Phenoxy, Chlorophenylthio, Methylphenylthio, Methylsulfonyl, Benzylthio, Dimethylbenzyl, Chlorobensyl, Dichlorobenzyl oder -CHO steht; oder R, und R^ gemeinsam eine Trimethylenbrückengruppe bilden; X für ein Sauerstoffoder Schwefelatom steht; Rn. für Wasserstoff, Hydroxyäthyl, Methoxypiethyl, Benzyl, Allyl, Methylcarboxyäthyl, Methylcarbonylmethyl, Diäthylaminoäthyl, Dimethylaminoäthyl, Äthylthioäthyl, Phenylcarbonyloxymethyl oder Äthoxyäthyl steht, mit der Voraussetzung, dass, wenn R1 und R2 beide Methyl sind, R1[I nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.
  3. 3. Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R1 und R3 für Niedrigalkyl, Niedrigalkenyl, Niedrigalkylcarbonyl, heterocyclisches Niedrigalkyl oder Carbamoyl steht; oder R1 und R2 gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden; R-, .für Wasserstoff, Niedrigalkyl oder Niedrigalkylthio-niedrigalkyl steht; R^ für Wasserstoff, Halogen, Niedrigalkyl, Phenylniedrigalkyl, Niedrigalkenyl, Niedrigalkoxy-niedrigalkyl, Kydroxyhalogen-niedrigalkyl, eine Niedrigalkylsruppe, die durch ein stickstoffhaltiges monocyclisches heterocyclisches Radikal substituiert ist, oder Niedrigalkylsulfonyl steht; X für Sauerstoff oder Schwefel steht; und R5 für Wasserstoff, Hydroxyniedrirtalkyl, Niedrigalkylcarbonyl-niedrigalkyl, Di-niedrig-
    509836/0917
    alkylamino-niedrigalkyl oder Niedrigalkylthio-niedrigalkyl steht, mit der Voraussetzung, dass, wenn R1 und Rp beide Methyl sind, R^ nicht Wasserstoff, Halogen, Allyl, Butyl oder Azo ist.
  4. 4. . Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R. und R2 für Niedrigalkyl stehen; oder R. und R2 gemeinsam mit dem benachbarten Stickstoffatom einen 5~ oder 6-gliedrigen heterocyclischen Ring bilden; R, für Niedrigalkyl steht; R^ für Niedrigalkyl oder Niedrigalkenyl steht; R1- für Wasserstoff steht; und X für ein Sauerstoff- oder Schwefelatom steht, mit der Voraussetzung, dass, wenn R1 und Rp beide Methyl sind, R^ nicht Allyl oder Butyl ist.
  5. 5· Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R^. und Rp für Niedrigalkyl oder Niedrigalkenyl stehen; oder R1 und R_ gemeinsam mit dem benachbarten Stickstoffatom einen heterocyclischen Ring bilden; R, für Niedrigalkyl steht; R1J für Niedrigalkyl oder Niedrigalkenyl steht; R1- für Wasserstoff steht; und X für ein Sauerstoff- oder Schwefelatom steht, mit der Voraussetzung, dass, wenn R1 und R2 beide Methyl sind, R1J nicht Allyl oder Butyl ist.
  6. 6. Pyrimidinderivate nach Anspruch 1, dadurch gekennzeichnet, dass R1 und R2 für Allyl, Methyl, Äthyl, Propyl oder Butyl steht; R, für Methyl und Äthyl steht; R^ für Methyl, Äthyl, Propyl, Butyl oder Amyl steht; R5 für Wasserstoff steht und X für Sauerstoff steht.
  7. 7. Die folgenden Pyrimidinderivate: 2-Dimethylamino-4-methyl-5-n-pentyl-6-hydroxypyrimidin, 2-Dimethylamino-4-methyl-5-n-propyl-6-hydroxypyrimidin, 2-Dimethylamino-iJ-äthyl-5-n~butyl-6-hydroxypyrimidin, 2-Äthylmethylamino-4-methyl-5-n-butyl-6-hydroxypyrimidin> 2-Diäthylamino-4-methyl-5-allyl~ö-hydroxypyrimidin,
    509836/0917
    2-Diäthylamino-4-methyl-5-n-butyl-6-hydroxypyrimidin, 2-Dimethylamino-4-methyl-5~äthyl-6-mercaptopyrimidin, 2-Dimethylamino-4-methyl-5-n-butyl-6-(2-dimethylaminoäthylthio)· pyrimidin,
    2-Dimethylamino-4-methyl-5~n-butyl-6-(2-diäthylaminoäthylthio)-pyrimidin,
    und die Salze derselben.
  8. 8. Die folgenden Pyrimidinderivate:
    2-Dimethylamino-4-hydroxy-6-methyl~5-n-pentylpyrimidin, 2-Dimethylamino-4-hydroxy-6-methyl-5~n-propylpyrimidin, 2-Dimethylamino-5-n-hexyl-il-hydroxy-6-methylpyrimidini 2-Diraethylamino-4-äthyl-6-hydroxypyrimidin, S-Benzyl^-dimethylamino^-hydroxy-ö-methylpyrimidin, 5-n-Butyl-2-dimethylamino-4-hydroxy-β-phenylpyrirrάdin, 2-Dimethylamino-4-hydroxy-6-methyl-5-isopropylpyrimidin, 5-n-But'yl-2-di-n-butylamino-4~hydroxy~6-methylpyrimidin, 2-Diraethylamino-4-äthyIthiomethy1-6-hydroxypyrimidin, 2-Dimethy lamino-5-(2-ä thy loxy)~ät hy 1-4-hydroxy-6-r.e thy 1-pyrinidin,
    thylairiino-^-hv'J:-c-x .■ -C rr.-.r;.r:': rL- y thy,1 arr;ino-5-St.':"''■ -·■ '■■-1Vyc'r··ox■■/■-- 6-ih":ta.T:i no-if-hy--■■■:■■· ' -; --^c-),;.:
    509836/0917 BAD ORIGINAL
    5-p-Chlorophenylfchio-2-dimethylamino-il-hydroxy-6-niethyl~ pyrimidin, S-n-Butyl^-dimethylamino-JJ-äthyl-o-hydroxypyrimidin, 2-Dimethylamino-4-hydroxy~6-methyl-5-p-tolylthippyrimidin, S-Benzylthio^-dimethylamino-^-hydroxy^-methylpyriinidin, S-n-Butyl^-äthylmethylamino-^-hydroxy-ö-rnethylpyrimidin, 2-Äthylmethylamino-4-hydroxy-6-methyl-5-n-propylpyrimidin, 2-Diäthylamino~4-hydroxy~6-methyl-5-n-propylpyrimidinJ 2-Dimethylamino-5-(3,4-dimethylbenzyl)-4-hydroxy-6~methylpyrimidin^ 5-p-Chlorobenzyl-2-dimethylamino-ii-hydroxy-6-methylpyrimidini 5-(3,4-Dichlorobenzyl)-2~dimethylamino-il-hydroxy-6-methylpyrimidin, 2-Diäthylamino-5"äthyl-4-hydroxy-6-methylpyrimidin, 5-Allyl-2-diäthylamino-4-hydroxy-6-methylpyrimidin, 2-Dimethylamino-5-äthyl-4-hydroxypyrimidin, 5-Allyl-2-dimethylainino-4-hydroxy-6-phenylpyriraidinJ 4-p-Chlorophenyl-2-diΓlethylamino-6-hydroxypyrimidin, 2-Dimethylamino-5-äthyl-4-hydroxy-6-phenylpyrimidin, 2-Dimethy!amino-4-hydroxy-5-p-methoxyphenylpyrimidin, 5-n-Butyl-2"dimethylamino-4-(2-hydroxyäthyloxy)-6-methylpyrimidirij 5-n-Butyl-!i~(2-diäthylaminoäthoxy)-2-dimethylamino-6-methylpyrimidirij 6-Benayloxy-2-diir;ethylaminopyrimidin, ö-AlIyloxy^-din.'ethylaminopyrimidin, 4 3 5-DimethyI -2"dirnethylamino-6- (2-hydroxyäthyloxy) -pyrimidin, 2-Dimet hy 1 amino-^-niercapto-D-methylpyrimidin, 5-n-ButyI~2"diäthyiamino-4-hydroxy-6-methylpyrimidin, 5-n-But~enyi-2~dirriethylainino"ii-hydroxy-6-methylpyrimidin, 5-n-Butyl"2~diallylamino-i|-hydroxy-6-methylpyrimidin, und die Salze davon»
  9. 9. Die Salze der Pyrimidinderivate nach Anspruch
    509836/0917
  10. 10. Die Salze der Verbindungen nach Anspruch 8.
  11. 11. Salze nach Anspruch 9, dadurch gekennzeichnet, dass es sich um Alkalimetallsalze oder Hydrohalogenide handelt,
  12. 12. 5-n-Butyl-2-dimethylamino-4-hydroxy-6-niethylpyrimidin~ hydrochlorid.
    13· Verfahren zur Herstellung der Verbindungen nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass man ein Guanidin der Formel
    H2N
    C=NH
    worin R^ und R2 die oben angegebenen Bedeutungen besitzen, mit einem beta-Ketoester der allgemeinen Formel
    R,.CO.CH.COOR
    worin R-, und R21 die oben angegebenen Bedeutungen besitzen und R für eine Alkylgruppe steht, kondensiert.
    '/■
    < .0!"i.-;NG.H.6OHH
    509836/0917
DE19671795772 1966-03-31 1967-03-23 In 5- und 6-stellung substituierte 2-amino-4-hydroxypyrimidinderivate Granted DE1795772B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1427166A GB1182584A (en) 1966-03-31 1966-03-31 Pyrimidine derivates and the use thereof as fungicides
GB1427167 1967-02-24

Publications (3)

Publication Number Publication Date
DE1795772A1 true DE1795772A1 (de) 1975-09-04
DE1795772B2 DE1795772B2 (de) 1977-11-10
DE1795772C3 DE1795772C3 (de) 1978-06-29

Family

ID=26250433

Family Applications (6)

Application Number Title Priority Date Filing Date
DE19671795833 Expired DE1795833C3 (de) 1966-03-31 1967-03-23 In 5-Stellung substituierte 2-Amino-6-hydroxy-pyrimidinderivate
DE1967J0033286 Granted DE1695270B2 (de) 1966-03-31 1967-03-23 Mittel zur bekaempfung von pilzen bei pflanzen
DE19671795726 Expired DE1795726C3 (de) 1966-03-31 1967-03-23 2-Amino-4-methyl-5-alkyl-6-hydroxy- . pyridinderivate
DE19671795835 Expired DE1795835C3 (de) 1966-03-31 1967-03-23 In 5-Stellung substituierte 2-Dimethylamino^-alkyl-e-hydroxy-bzw.-mercapto-Pyrimidinderivate
DE19671795834 Pending DE1795834A1 (de) 1966-03-31 1967-03-23 Fungicide zusammensetzungen und verfahren zur herstellung derselben
DE19671795772 Granted DE1795772B2 (de) 1966-03-31 1967-03-23 In 5- und 6-stellung substituierte 2-amino-4-hydroxypyrimidinderivate

Family Applications Before (5)

Application Number Title Priority Date Filing Date
DE19671795833 Expired DE1795833C3 (de) 1966-03-31 1967-03-23 In 5-Stellung substituierte 2-Amino-6-hydroxy-pyrimidinderivate
DE1967J0033286 Granted DE1695270B2 (de) 1966-03-31 1967-03-23 Mittel zur bekaempfung von pilzen bei pflanzen
DE19671795726 Expired DE1795726C3 (de) 1966-03-31 1967-03-23 2-Amino-4-methyl-5-alkyl-6-hydroxy- . pyridinderivate
DE19671795835 Expired DE1795835C3 (de) 1966-03-31 1967-03-23 In 5-Stellung substituierte 2-Dimethylamino^-alkyl-e-hydroxy-bzw.-mercapto-Pyrimidinderivate
DE19671795834 Pending DE1795834A1 (de) 1966-03-31 1967-03-23 Fungicide zusammensetzungen und verfahren zur herstellung derselben

Country Status (16)

Country Link
AT (3) AT286992B (de)
BE (1) BE696470A (de)
BR (1) BR6788228D0 (de)
CH (1) CH497836A (de)
CS (1) CS165324B2 (de)
CY (1) CY623A (de)
DE (6) DE1795833C3 (de)
DK (1) DK126593B (de)
ES (1) ES338694A1 (de)
GB (1) GB1182584A (de)
IL (1) IL27542A (de)
MY (1) MY7300287A (de)
NL (1) NL152855B (de)
PH (1) PH11586A (de)
SE (2) SE356874B (de)
YU (1) YU33661B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4029784A (en) * 1971-09-23 1977-06-14 Imperial Chemical Industries Limited Pyrimidine sulfamate fungicides
GB1523274A (en) 1974-08-05 1978-08-31 Ici Ltd Herbicidal compositions containing substituted pyrimidine
IT1153066B (it) * 1982-11-18 1987-01-14 Mentedison S P A Derivati del pirimidin-4-one ad attivita' erbicida
JPH0635450B2 (ja) * 1984-03-16 1994-05-11 三井東圧化学株式会社 チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
JPS6345269A (ja) * 1986-04-28 1988-02-26 Mitsui Toatsu Chem Inc ジハロゲン置換チオシアノピリミジン誘導体、その製造法および農園芸用殺菌剤
US6252076B1 (en) 1996-05-04 2001-06-26 Yuhan Corporation Process for preparation of pyrimidine derivatives
WO1998018784A1 (en) * 1996-10-29 1998-05-07 Yuhan Corporation Process for preparation of pyrimidine derivatives
IN188411B (de) 1997-03-27 2002-09-21 Yuhan Corp
WO1999031072A1 (en) * 1997-12-18 1999-06-24 E.I. Du Pont De Nemours And Company Cyclohexylamine arthropodicides and fungicides
KR100272471B1 (ko) 1998-11-17 2000-11-15 김선진 신규의 피리미딘 유도체 및 그의 제조방법
EP2489262B1 (de) 2006-09-18 2018-11-14 Basf Se Pestizide mischungen, die ein anthranilamidinsektizid und ein fungizid enthalten
US20100029698A1 (en) 2007-02-06 2010-02-04 Basf Se Pesticidal Mixtures
EP2161259A1 (de) * 2008-09-03 2010-03-10 Bayer CropScience AG 4-Halogenalkylsubstituierte Diaminopyrimidine als Fungizide
CN102461503B (zh) * 2010-11-08 2013-08-14 陕西汤普森生物科技有限公司 一种含双炔酰菌胺与乙嘧酚的杀菌组合物
UY35735A (es) 2013-09-16 2015-04-30 Bayer Pharma AG Trifluorometilpirimidinonas disustituidas y su uso

Also Published As

Publication number Publication date
SE356874B (de) 1973-06-12
DE1795833B2 (de) 1977-08-25
CH497836A (de) 1970-10-31
DE1795726B2 (de) 1977-09-01
DE1795772B2 (de) 1977-11-10
DE1795835A1 (de) 1976-06-24
DE1695270B2 (de) 1977-05-26
DE1795834A1 (de) 1976-06-24
YU33661B (en) 1977-12-31
DE1795726C3 (de) 1978-07-27
AT286992B (de) 1971-01-11
YU63067A (en) 1977-06-30
SE405117B (sv) 1978-11-20
CY623A (en) 1971-12-08
MY7300287A (en) 1973-12-31
NL6704456A (de) 1967-10-02
DE1795835C3 (de) 1978-04-13
AT276854B (de) 1969-12-10
BE696470A (de) 1967-10-02
DK126593B (da) 1973-07-30
AT279968B (de) 1970-03-25
BR6788228D0 (pt) 1973-06-05
ES338694A1 (es) 1968-07-01
IL27542A (en) 1975-10-15
DE1795833A1 (de) 1976-03-11
DE1795833C3 (de) 1978-04-13
DE1695270A1 (de) 1972-04-20
NL152855B (nl) 1977-04-15
DE1795726A1 (de) 1975-07-31
DE1795772C3 (de) 1978-06-29
PH11586A (en) 1978-03-31
CS165324B2 (de) 1975-12-22
DE1795835B2 (de) 1977-08-25
GB1182584A (en) 1970-02-25

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