SK279516B6 - Substituované deriváty pyrimidínu, spôsob ich výro - Google Patents

Substituované deriváty pyrimidínu, spôsob ich výro Download PDF

Info

Publication number: SK279516B6
Authority: SK; Slovakia
Prior art keywords: hydrogen; group; formula; general formula; atom
Prior art date: 1992-07-17

Application number

SK32-95A

Other languages

English (en)

Slovak (sk)

Other versions

SK3295A3 (en

Inventor

David Munro

Royston Davis

Janet A. Day

Jacqueline A. Wilkin

William W. Wood

Original Assignee

Shell Internationale Research Maatschappij B.V.

Priority date (The priority date 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 date listed.)

1992-07-17

Filing date

1993-07-15

Publication date

1998-12-02

1993-07-15 Application filed by Shell Internationale Research Maatschappij B.V. filed Critical Shell Internationale Research Maatschappij B.V.

1995-05-10 Publication of SK3295A3 publication Critical patent/SK3295A3/sk

1998-12-02 Publication of SK279516B6 publication Critical patent/SK279516B6/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 46
238000000034 method Methods 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title claims abstract description 22
230000000361 pesticidal effect Effects 0.000 title claims abstract description 10
239000000543 intermediate Substances 0.000 title claims abstract description 4
150000003230 pyrimidines Chemical class 0.000 title claims description 20
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 12
150000001875 compounds Chemical class 0.000 claims abstract description 81
239000000460 chlorine Substances 0.000 claims abstract description 33
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
239000001257 hydrogen Substances 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
150000002431 hydrogen Chemical class 0.000 claims abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
-1 bromo, butyl Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 21
239000004480 active ingredient Substances 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 12
241000607479 Yersinia pestis Species 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
244000078703 ectoparasite Species 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
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 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 2
125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 2
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims 1
125000006001 difluoroethyl group Chemical group 0.000 claims 1
YQCBYQLDAHUMCO-UHFFFAOYSA-N n-(3-chlorophenyl)pyrimidin-2-amine Chemical compound ClC1=CC=CC(NC=2N=CC=CN=2)=C1 YQCBYQLDAHUMCO-UHFFFAOYSA-N 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
125000000262 haloalkenyl group Chemical group 0.000 abstract description 2
125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
229910052760 oxygen Inorganic materials 0.000 abstract description 2
239000001301 oxygen Substances 0.000 abstract description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 abstract 1
125000004441 haloalkylsulfonyl group Chemical group 0.000 abstract 1
125000004995 haloalkylthio group Chemical group 0.000 abstract 1
125000000232 haloalkynyl group Chemical group 0.000 abstract 1
238000012360 testing method Methods 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 18
230000000895 acaricidal effect Effects 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000243 solution Substances 0.000 description 12
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238000006243 chemical reaction Methods 0.000 description 9
235000013601 eggs Nutrition 0.000 description 9
239000007787 solid Substances 0.000 description 9
238000000921 elemental analysis Methods 0.000 description 8
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230000000052 comparative effect Effects 0.000 description 7
239000011734 sodium Substances 0.000 description 7
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
230000001988 toxicity Effects 0.000 description 6
231100000419 toxicity Toxicity 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
244000046052 Phaseolus vulgaris Species 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000009835 boiling Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
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 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
101100042793 Gallus gallus SMC2 gene Proteins 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
241000018137 Trialeurodes vaporariorum Species 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
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239000002917 insecticide Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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235000011152 sodium sulphate Nutrition 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
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230000000694 effects Effects 0.000 description 3
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LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical group CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
230000035515 penetration Effects 0.000 description 3
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239000002244 precipitate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
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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 2
IPOSYDIOAOBMSZ-UHFFFAOYSA-N 4,6-bis[4-chloro-3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(OC=2N=CN=C(OC=3C=C(C(Cl)=CC=3)C(F)(F)F)C=2)=C1 IPOSYDIOAOBMSZ-UHFFFAOYSA-N 0.000 description 2
QFWVAJQVYBRTCL-UHFFFAOYSA-N 4,6-dichloro-2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC(Cl)=CC(Cl)=N1 QFWVAJQVYBRTCL-UHFFFAOYSA-N 0.000 description 2
CPYSKABWRUCXBU-UHFFFAOYSA-N 4-[6-[4-fluoro-3-(trifluoromethyl)phenoxy]pyrimidin-4-yl]oxybenzonitrile Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1OC1=CC(OC=2C=CC(=CC=2)C#N)=NC=N1 CPYSKABWRUCXBU-UHFFFAOYSA-N 0.000 description 2
VOWPIDJSINRFPZ-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)phenol Chemical compound OC1=CC=C(Br)C(C(F)(F)F)=C1 VOWPIDJSINRFPZ-UHFFFAOYSA-N 0.000 description 2
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 2
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239000002243 precursor Substances 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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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
- C07D239/48—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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (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)

SK32-95A 1992-07-17 1993-07-15 Substituované deriváty pyrimidínu, spôsob ich výro SK279516B6 (sk)

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 (2)

Publication Number	Publication Date
SK3295A3 SK3295A3 (en)	1995-05-10
SK279516B6 true SK279516B6 (sk)	1998-12-02

Family

ID=8211436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK32-95A SK279516B6 (sk)	1992-07-17	1993-07-15	Substituované deriváty pyrimidínu, spôsob ich výro

Country Status (27)

Country	Link
US (1)	US5707995A (pl)
EP (1)	EP0650482B1 (pl)
JP (1)	JP3353895B2 (pl)
KR (1)	KR950702541A (pl)
CN (1)	CN1087085A (pl)
AT (1)	ATE206404T1 (pl)
AU (1)	AU671845B2 (pl)
CA (1)	CA2140346A1 (pl)
CZ (1)	CZ282275B6 (pl)
DE (1)	DE69330882T2 (pl)
DK (1)	DK0650482T3 (pl)
EG (1)	EG20267A (pl)
ES (1)	ES2164666T3 (pl)
GE (1)	GEP19981224B (pl)
HU (1)	HUT70086A (pl)
IL (1)	IL106324A (pl)
MD (1)	MD1154F2 (pl)
OA (1)	OA10124A (pl)
PL (6)	PL173021B1 (pl)
PT (1)	PT650482E (pl)
RU (1)	RU95105445A (pl)
SG (1)	SG49712A1 (pl)
SK (1)	SK279516B6 (pl)
TR (1)	TR26781A (pl)
TW (1)	TW234077B (pl)
WO (1)	WO1994002470A1 (pl)
ZA (1)	ZA935155B (pl)

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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
ATE251141T1 (de)	1995-03-10	2003-10-15	Berlex Lab	Benzamidin-derivate, deren herstellung und deren verwendung als anti-koagulantien
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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
CN1234798A (zh)	1996-09-12	1999-11-10	舍林股份公司	环状氨基酸和环状羟基羧酸衍生物取代的苄脒衍生物和它们用作抗凝剂的用途
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DE19710609A1 (de) *	1997-03-14	1998-09-17	Bayer Ag	Substituierte Aminosalicylsäureamide
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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
ES2361146T3 (es)	1998-03-27	2011-06-14	Janssen Pharmaceutica Nv	Derivados de la piramidina inhibitatoria de vih.
US6087498A (en) *	1998-05-12	2000-07-11	American Cyanamid Company	Process for the preparation of unsymmetrical 4,6-bis(aryloxy) pyrimidine compounds
US6342499B1 (en)	1998-07-14	2002-01-29	Basf Aktiengesellschaft	Parasitic and saprophagous mite control in beneficial insects
CA2277719A1 (en) *	1998-07-14	2000-01-14	American Cyanamid Company	Parasitic and saprophagous mite control on beneficial insects
US6281219B1 (en)	1998-07-14	2001-08-28	American Cyanamid Co.	Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof
ATE205835T1 (de) *	1998-07-14	2001-10-15	Basf Ag	Akarizid und insektizid wirksame, substituierte pyrimidine und verfahren zu ihrer herstellung
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
AU5020400A (en) *	1999-05-20	2000-12-12	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
WO2001022938A1 (en)	1999-09-24	2001-04-05	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
WO2005047268A2 (en) *	2003-11-10	2005-05-26	X-Ceptor Therapeutics, 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
CA2657745C (en) *	2006-07-21	2015-02-17	Novartis Ag	Pyrimidine derivatives and their use as pesticides
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

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US5145856A (en) *	1989-02-10	1992-09-08	Imperial Chemical Industries Plc	Fungicides
GB8903019D0 (en) *	1989-02-10	1989-03-30	Ici Plc	Fungicides

1993
- 1993-07-13 IL IL10632493A patent/IL106324A/en unknown
- 1993-07-13 TW TW082105581A patent/TW234077B/zh active
- 1993-07-15 HU HU9500127A patent/HUT70086A/hu unknown
- 1993-07-15 AT AT93915936T patent/ATE206404T1/de not_active IP Right Cessation
- 1993-07-15 KR KR1019950700201A patent/KR950702541A/ko not_active Application Discontinuation
- 1993-07-15 SK SK32-95A patent/SK279516B6/sk unknown
- 1993-07-15 SG SG1996004295A patent/SG49712A1/en unknown
- 1993-07-15 PL PL93307131A patent/PL173021B1/pl unknown
- 1993-07-15 AU AU45700/93A patent/AU671845B2/en not_active Ceased
- 1993-07-15 PL PL93317717A patent/PL173717B1/pl unknown
- 1993-07-15 PL PL93317719A patent/PL173056B1/pl unknown
- 1993-07-15 US US08/351,477 patent/US5707995A/en not_active Expired - Fee Related
- 1993-07-15 PL PL93317720A patent/PL173467B1/pl unknown
- 1993-07-15 MD MD95-0235A patent/MD1154F2/ro unknown
- 1993-07-15 DK DK93915936T patent/DK0650482T3/da active
- 1993-07-15 EG EG44493A patent/EG20267A/xx active
- 1993-07-15 CA CA002140346A patent/CA2140346A1/en not_active Abandoned
- 1993-07-15 RU RU95105445/04A patent/RU95105445A/ru unknown
- 1993-07-15 ES ES93915936T patent/ES2164666T3/es not_active Expired - Lifetime
- 1993-07-15 WO PCT/EP1993/001880 patent/WO1994002470A1/en active IP Right Grant
- 1993-07-15 PL PL93317716A patent/PL173066B1/pl unknown
- 1993-07-15 CZ CZ9530A patent/CZ282275B6/cs unknown
- 1993-07-15 GE GEAP19932333A patent/GEP19981224B/en unknown
- 1993-07-15 PT PT93915936T patent/PT650482E/pt unknown
- 1993-07-15 DE DE69330882T patent/DE69330882T2/de not_active Expired - Fee Related
- 1993-07-15 EP EP93915936A patent/EP0650482B1/en not_active Expired - Lifetime
- 1993-07-15 JP JP50413894A patent/JP3353895B2/ja not_active Expired - Fee Related
- 1993-07-15 PL PL93317718A patent/PL173091B1/pl unknown
- 1993-07-16 ZA ZA935155A patent/ZA935155B/xx unknown
- 1993-07-16 CN CN93116763A patent/CN1087085A/zh active Pending
- 1993-07-19 TR TR93/0604A patent/TR26781A/xx unknown
1995
- 1995-01-12 OA OA60603A patent/OA10124A/en unknown

Also Published As

Publication number	Publication date
RU95105445A (ru)	1996-10-27
PL173717B1 (pl)	1998-04-30
JP3353895B2 (ja)	2002-12-03
PL307131A1 (en)	1995-05-02
PT650482E (pt)	2002-03-28
IL106324A0 (en)	1993-11-15
CZ282275B6 (cs)	1997-06-11
MD1154F2 (ro)	1999-02-28
DK0650482T3 (da)	2001-12-03
TR26781A (tr)	1995-05-15
CA2140346A1 (en)	1994-02-03
KR950702541A (ko)	1995-07-29
EP0650482A1 (en)	1995-05-03
EP0650482B1 (en)	2001-10-04
DE69330882T2 (de)	2002-04-11
AU671845B2 (en)	1996-09-12
HUT70086A (en)	1995-09-28
SK3295A3 (en)	1995-05-10
ZA935155B (en)	1994-06-20
WO1994002470A1 (en)	1994-02-03
JPH07508999A (ja)	1995-10-05
US5707995A (en)	1998-01-13
IL106324A (en)	1998-09-24
ES2164666T3 (es)	2002-03-01
PL173056B1 (pl)	1998-01-30
GEP19981224B (en)	1998-02-11
PL173467B1 (pl)	1998-03-31
DE69330882D1 (de)	2001-11-08
EG20267A (en)	1998-05-31
CN1087085A (zh)	1994-05-25
PL173091B1 (pl)	1998-01-30
PL173066B1 (pl)	1998-01-30
CZ3095A3 (en)	1995-09-13
TW234077B (pl)	1994-11-11
OA10124A (en)	1996-12-18
SG49712A1 (en)	1998-06-15
MD950235A (ro)	1997-10-31
ATE206404T1 (de)	2001-10-15
PL173021B1 (pl)	1998-01-30
AU4570093A (en)	1994-02-14

Publication	Publication Date	Title
SK279516B6 (sk)	1998-12-02	Substituované deriváty pyrimidínu, spôsob ich výro
LT3663B (en)	1996-01-25	Pyridine derivatives, process for their production, herbicidal method and composition
EP0336494A2 (en)	1989-10-11	Triazine herbicides
NZ211686A (en)	1988-01-08	Benzoylurea derivatives and pesticidal compositions
JPS62263162A (ja)	1987-11-16	置換２，４−ジアミノ−５−シアノピリミジン及び該化合物を含有する有害生物防除剤
US5134145A (en)	1992-07-28	Pesticidal pyrimidinyl benzoic acids and esters
US5134144A (en)	1992-07-28	Pesticidal 3-arylpyrimidinyl ethers and thioethers
US4866079A (en)	1989-09-12	N-pyridyloxyphenylisothioureas and the use thereof in pest control
US5759956A (en)	1998-06-02	Herbicidal compounds
US5426090A (en)	1995-06-20	Heterocyclic compounds
JPS6368559A (ja)	1988-03-28	置換チオ尿素、イソチオ尿素及びカルボジイミド化合物、それらの製法、有害生物防除剤としてのそれらの使用及び該化合物製造用中間体
JPH05279210A (ja)	1993-10-26	スルホンアミド除草剤
KR920005411B1 (ko)	1992-07-03	치환된 테트라졸의 제법
JPS6163649A (ja)	1986-04-01	ベンゾイル尿素化合物，それらの製造方法並びに殺虫剤組成物
EP0103918A2 (en)	1984-03-28	Pesticidal benzoylurea compounds
EP0589947A1 (en)	1994-04-06	Sulphonamide herbicides
IE62701B1 (en)	1995-02-22	Benzamide compounds, their preparation and their use as pesticides
JPS6178759A (ja)	1986-04-22	置換カルボジイミド及びその製造方法並びに殺虫・殺ダニ組成物
CN1016220B (zh)	1992-04-15	杂环除莠剂
JPS61267561A (ja)	1986-11-27	殺虫性ニトロメチレン誘導体