PL173717B1 - Sposób wytwarzania związków pirymidynowych - Google Patents
Sposób wytwarzania związków pirymidynowychInfo
- Publication number
- PL173717B1 PL173717B1 PL93317717A PL31771793A PL173717B1 PL 173717 B1 PL173717 B1 PL 173717B1 PL 93317717 A PL93317717 A PL 93317717A PL 31771793 A PL31771793 A PL 31771793A PL 173717 B1 PL173717 B1 PL 173717B1
- Authority
- PL
- Poland
- Prior art keywords
- hydrogen
- alkyl
- group
- atom
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000003230 pyrimidines Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- -1 haloalkylsulphinyl Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000460 chlorine Substances 0.000 abstract description 6
- 230000000361 pesticidal effect Effects 0.000 abstract description 4
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract description 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000895 acaricidal effect Effects 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000013601 eggs Nutrition 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YMWAEUVISMTDQH-UHFFFAOYSA-N 4,6-bis[3-(trifluoromethyl)phenoxy]-1h-pyrimidin-2-one Chemical compound FC(F)(F)C1=CC=CC(OC2=NC(=O)NC(OC=3C=C(C=CC=3)C(F)(F)F)=C2)=C1 YMWAEUVISMTDQH-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000506680 Haemulon melanurum Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 244000013123 dwarf bean Species 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- WMHSWGPTVOZBRT-UHFFFAOYSA-N 2-bromo-4,6-bis[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Br)N=C(OC=3C=C(C=CC=3)C(F)(F)F)C=2)=C1 WMHSWGPTVOZBRT-UHFFFAOYSA-N 0.000 description 1
- XFAVZJOPYVLVGO-UHFFFAOYSA-N 2-bromo-4-[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound FC(C=1C=C(OC2=NC(=NC=C2)Br)C=CC=1)(F)F XFAVZJOPYVLVGO-UHFFFAOYSA-N 0.000 description 1
- AMSINXYIZTZWPM-UHFFFAOYSA-N 2-chloro-4,6-bis[4-fluoro-3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1OC1=CC(OC=2C=C(C(F)=CC=2)C(F)(F)F)=NC(Cl)=N1 AMSINXYIZTZWPM-UHFFFAOYSA-N 0.000 description 1
- UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
- AEWYQQIPHJWWJR-UHFFFAOYSA-N 4,6-bis[4-fluoro-3-(trifluoromethyl)phenoxy]pyrimidin-2-amine Chemical compound C=1C(OC=2C=C(C(F)=CC=2)C(F)(F)F)=NC(N)=NC=1OC1=CC=C(F)C(C(F)(F)F)=C1 AEWYQQIPHJWWJR-UHFFFAOYSA-N 0.000 description 1
- YFUDLRFOGLVNNA-UHFFFAOYSA-N 4,6-dichloro-1h-pyrimidin-2-one Chemical compound ClC=1C=C(Cl)NC(=O)N=1 YFUDLRFOGLVNNA-UHFFFAOYSA-N 0.000 description 1
- DRTIDKPIEULFOI-UHFFFAOYSA-N 4,6-diphenoxypyrimidin-2-amine Chemical compound C=1C(OC=2C=CC=CC=2)=NC(N)=NC=1OC1=CC=CC=C1 DRTIDKPIEULFOI-UHFFFAOYSA-N 0.000 description 1
- ALCHUZGEEVNJJW-UHFFFAOYSA-N 4-n,6-n-bis(3-chlorophenyl)pyrimidine-2,4,6-triamine Chemical compound C=1C(NC=2C=C(Cl)C=CC=2)=NC(N)=NC=1NC1=CC=CC(Cl)=C1 ALCHUZGEEVNJJW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000282994 Cervidae Species 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910019201 POBr3 Inorganic materials 0.000 description 1
- 241000488585 Panonychus Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000018135 Trialeurodes Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000005675 difluoroethenyl group Chemical group [H]C(*)=C(F)F 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000013101 initial test Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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
- C07D239/48—Two nitrogen 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- C07D239/58—Two sulfur 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
- C07D239/60—Three or more oxygen or sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92306600 | 1992-07-17 | ||
| PCT/EP1993/001880 WO1994002470A1 (en) | 1992-07-17 | 1993-07-15 | Pesticidal pyrimidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL173717B1 true PL173717B1 (pl) | 1998-04-30 |
Family
ID=8211436
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL93317717A PL173717B1 (pl) | 1992-07-17 | 1993-07-15 | Sposób wytwarzania związków pirymidynowych |
| PL93317716A PL173066B1 (pl) | 1992-07-17 | 1993-07-15 | Sposób wytwarzania związków pirymidynowych |
| PL93317720A PL173467B1 (pl) | 1992-07-17 | 1993-07-15 | Środek szkodnikobójczy |
| PL93307131A PL173021B1 (pl) | 1992-07-17 | 1993-07-15 | Podstawione związki pirymidynowe |
| PL93317718A PL173091B1 (pl) | 1992-07-17 | 1993-07-15 | Podstawione związki pirymidynowe |
| PL93317719A PL173056B1 (pl) | 1992-07-17 | 1993-07-15 | Sposób wytwarzania podstawionych związków pirymidynowych |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL93317716A PL173066B1 (pl) | 1992-07-17 | 1993-07-15 | Sposób wytwarzania związków pirymidynowych |
| PL93317720A PL173467B1 (pl) | 1992-07-17 | 1993-07-15 | Środek szkodnikobójczy |
| PL93307131A PL173021B1 (pl) | 1992-07-17 | 1993-07-15 | Podstawione związki pirymidynowe |
| PL93317718A PL173091B1 (pl) | 1992-07-17 | 1993-07-15 | Podstawione związki pirymidynowe |
| PL93317719A PL173056B1 (pl) | 1992-07-17 | 1993-07-15 | Sposób wytwarzania podstawionych związków pirymidynowych |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5707995A (en:Method) |
| EP (1) | EP0650482B1 (en:Method) |
| JP (1) | JP3353895B2 (en:Method) |
| KR (1) | KR950702541A (en:Method) |
| CN (1) | CN1087085A (en:Method) |
| AT (1) | ATE206404T1 (en:Method) |
| AU (1) | AU671845B2 (en:Method) |
| CA (1) | CA2140346A1 (en:Method) |
| CZ (1) | CZ282275B6 (en:Method) |
| DE (1) | DE69330882T2 (en:Method) |
| DK (1) | DK0650482T3 (en:Method) |
| EG (1) | EG20267A (en:Method) |
| ES (1) | ES2164666T3 (en:Method) |
| GE (1) | GEP19981224B (en:Method) |
| HU (1) | HUT70086A (en:Method) |
| IL (1) | IL106324A (en:Method) |
| MD (1) | MD1154F2 (en:Method) |
| OA (1) | OA10124A (en:Method) |
| PL (6) | PL173717B1 (en:Method) |
| PT (1) | PT650482E (en:Method) |
| RU (1) | RU95105445A (en:Method) |
| SG (1) | SG49712A1 (en:Method) |
| SK (1) | SK279516B6 (en:Method) |
| TR (1) | TR26781A (en:Method) |
| TW (1) | TW234077B (en:Method) |
| WO (1) | WO1994002470A1 (en:Method) |
| ZA (1) | ZA935155B (en:Method) |
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| IE53930B1 (en) | 1982-04-07 | 1989-04-12 | Nat Res Dev | Endoprosthetic bone joint devices |
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| GB9325217D0 (en) * | 1993-12-09 | 1994-02-09 | Zeneca Ltd | Pyrimidine derivatives |
| CZ290330B6 (cs) * | 1995-01-26 | 2002-07-17 | American Cyanamid Company | 2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin |
| EP0723960B1 (en) * | 1995-01-26 | 2003-04-02 | Basf Aktiengesellschaft | Herbicidal 2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines |
| US5849758A (en) * | 1995-05-30 | 1998-12-15 | American Cyanamid Company | Herbicidal 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines |
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| US5994375A (en) | 1996-02-12 | 1999-11-30 | Berlex Laboratories, Inc. | Benzamidine derivatives substituted by amino acid and hydroxy acid derivatives and their use as anti-coagulants |
| UA53611C2 (uk) * | 1996-03-07 | 2003-02-17 | Амерікан Ціанамід Компані | Спосіб одержання несиметричних 4,6-біс(арилокси)піримідинових сполук |
| EP0894791A4 (en) * | 1996-03-29 | 2001-07-11 | Ube Industries | PYRIMIDINE COMPOUNDS, METHOD FOR THEIR PRODUCTION AND BACTERICIDES FOR AGRICULTURE AND Horticulture |
| IL128691A (en) | 1996-09-12 | 2007-07-24 | Bayer Schering Pharma Ag | History of enzamidine converted by annular amino acid and history of annular hydroxy acid and their use against coagulation |
| US6004985A (en) * | 1996-10-09 | 1999-12-21 | Berlex Laboratories, Inc. | Thio acid derived monocylic N-heterocyclics as anticoagulants |
| DE19710609A1 (de) * | 1997-03-14 | 1998-09-17 | Bayer Ag | Substituierte Aminosalicylsäureamide |
| WO1998054154A1 (en) * | 1997-05-28 | 1998-12-03 | Nippon Soda Co., Ltd. | Pyrimidine compounds, process for producing the same, and pesticides |
| 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 |
| US5849910A (en) * | 1997-09-05 | 1998-12-15 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis aryloxy-pyrimidine compounds |
| US6686364B2 (en) | 1997-12-08 | 2004-02-03 | Berlex Laboratories, Inc. | Benzamidine derivatives and their use as anti-coagulants |
| KR100643419B1 (ko) | 1998-03-27 | 2006-11-10 | 얀센 파마슈티카 엔.브이. | Ｈｉｖ를 억제하는 피리미딘 유도체 |
| US6087498A (en) * | 1998-05-12 | 2000-07-11 | American Cyanamid Company | Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds |
| US6281219B1 (en) | 1998-07-14 | 2001-08-28 | American Cyanamid Co. | Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof |
| CA2277719A1 (en) * | 1998-07-14 | 2000-01-14 | American Cyanamid Company | Parasitic and saprophagous mite control on beneficial insects |
| DE69900297T2 (de) * | 1998-07-14 | 2002-05-02 | Basf Ag | Akarizid und insektizid wirksame, substituierte Pyrimidine und Verfahren zu ihrer Herstellung |
| US6342499B1 (en) | 1998-07-14 | 2002-01-29 | Basf Aktiengesellschaft | Parasitic and saprophagous mite control in beneficial insects |
| US6262088B1 (en) | 1998-11-19 | 2001-07-17 | Berlex Laboratories, Inc. | Polyhydroxylated monocyclic N-heterocyclic derivatives as anti-coagulants |
| US6127376A (en) | 1998-12-04 | 2000-10-03 | Berlex Laboratories, Inc. | Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants |
| AU3357700A (en) * | 1999-02-16 | 2000-09-04 | E.I. Du Pont De Nemours And Company | Phenoxypyrimidine insecticides and acaricides |
| CO5210940A1 (es) * | 1999-05-04 | 2002-10-30 | Novartis Ag | Compuestos plaguicidas derivados de pirimidina y composiciones que los contienen |
| WO2000071536A1 (en) * | 1999-05-20 | 2000-11-30 | E.I. Du Pont De Nemours And Company | Heteroaryloxypyrimidine insecticides and acaricides |
| US6350761B1 (en) | 1999-07-30 | 2002-02-26 | Berlex Laboratories, Inc. | Benzenamine derivatives as anti-coagulants |
| AU775360B2 (en) | 1999-09-24 | 2004-07-29 | Janssen Pharmaceutica N.V. | Antiviral compositions |
| US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
| DE10013914A1 (de) | 2000-03-21 | 2001-09-27 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10014607A1 (de) | 2000-03-24 | 2001-09-27 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen 4,6-Bis(aryloxy pyrimidin-Derivaten |
| DE10055941A1 (de) | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| US8455489B2 (en) * | 2003-11-10 | 2013-06-04 | Exelixis, Inc. | Substituted pyrimidine compositions and methods of use |
| DE10353281A1 (de) | 2003-11-14 | 2005-06-16 | Bayer Cropscience Ag | Wirkstoffkombination mit insektiziden und akariziden Eigenschaften |
| EP1574502A1 (en) * | 2004-03-08 | 2005-09-14 | Novartis AG | Use of pyrimidine compounds in the preparation of parasiticides |
| RU2448097C2 (ru) * | 2006-07-21 | 2012-04-20 | Новартис Аг | Производные пиримидина и их применение в качестве пестицидов |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| WO2012000922A2 (en) * | 2010-06-28 | 2012-01-05 | Novartis Ag | New Use |
| JP2015083541A (ja) * | 2012-02-03 | 2015-04-30 | アグロカネショウ株式会社 | 対称性４，６−ビス（アリールオキシ）ピリミジン化合物の製造方法 |
| CN105777653A (zh) * | 2014-12-26 | 2016-07-20 | 中国科学院上海药物研究所 | 用作Lp-PLA2抑制剂的嘧啶酮类化合物及其药物组合物 |
| CN106008368A (zh) * | 2016-06-22 | 2016-10-12 | 连云港笃翔化工有限公司 | 2, 4, 6-三氯嘧啶一锅法合成2-烃巯基-4, 6-二烃氧基嘧啶类化合物及其制备方法 |
| CN109721548B (zh) * | 2017-10-31 | 2020-11-13 | 南通泰禾化工股份有限公司 | 一种嘧菌酯的制备方法 |
| CN109824603B (zh) * | 2017-11-23 | 2021-03-12 | 浙江省化工研究院有限公司 | 一种嘧啶胺类化合物、其制备方法及应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
| US5145856A (en) * | 1989-02-10 | 1992-09-08 | Imperial Chemical Industries Plc | Fungicides |
-
1993
- 1993-07-13 IL IL10632493A patent/IL106324A/en unknown
- 1993-07-13 TW TW082105581A patent/TW234077B/zh active
- 1993-07-15 DE DE69330882T patent/DE69330882T2/de not_active Expired - Fee Related
- 1993-07-15 PL PL93317717A patent/PL173717B1/pl unknown
- 1993-07-15 CZ CZ9530A patent/CZ282275B6/cs unknown
- 1993-07-15 AT AT93915936T patent/ATE206404T1/de not_active IP Right Cessation
- 1993-07-15 PL PL93317716A patent/PL173066B1/pl unknown
- 1993-07-15 CA CA002140346A patent/CA2140346A1/en not_active Abandoned
- 1993-07-15 PL PL93317720A patent/PL173467B1/pl unknown
- 1993-07-15 PL PL93307131A patent/PL173021B1/pl unknown
- 1993-07-15 DK DK93915936T patent/DK0650482T3/da active
- 1993-07-15 EG EG44493A patent/EG20267A/xx active
- 1993-07-15 PT PT93915936T patent/PT650482E/pt unknown
- 1993-07-15 US US08/351,477 patent/US5707995A/en not_active Expired - Fee Related
- 1993-07-15 MD MD95-0235A patent/MD1154F2/ro unknown
- 1993-07-15 SG SG1996004295A patent/SG49712A1/en unknown
- 1993-07-15 EP EP93915936A patent/EP0650482B1/en not_active Expired - Lifetime
- 1993-07-15 AU AU45700/93A patent/AU671845B2/en not_active Ceased
- 1993-07-15 HU HU9500127A patent/HUT70086A/hu unknown
- 1993-07-15 PL PL93317718A patent/PL173091B1/pl unknown
- 1993-07-15 PL PL93317719A patent/PL173056B1/pl unknown
- 1993-07-15 ES ES93915936T patent/ES2164666T3/es not_active Expired - Lifetime
- 1993-07-15 RU RU95105445/04A patent/RU95105445A/ru unknown
- 1993-07-15 GE GEAP19932333A patent/GEP19981224B/en unknown
- 1993-07-15 WO PCT/EP1993/001880 patent/WO1994002470A1/en not_active Ceased
- 1993-07-15 SK SK32-95A patent/SK279516B6/sk unknown
- 1993-07-15 JP JP50413894A patent/JP3353895B2/ja not_active Expired - Fee Related
- 1993-07-15 KR KR1019950700201A patent/KR950702541A/ko not_active Ceased
- 1993-07-16 CN CN93116763A patent/CN1087085A/zh active Pending
- 1993-07-16 ZA ZA935155A patent/ZA935155B/xx unknown
- 1993-07-19 TR TR93/0604A patent/TR26781A/xx unknown
-
1995
- 1995-01-12 OA OA60603A patent/OA10124A/en unknown
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