UA78255C2 - 5-phenylpyrimidines, method of production thereof (variants), fungicidal agent containing thereof - Google Patents
5-phenylpyrimidines, method of production thereof (variants), fungicidal agent containing thereof Download PDFInfo
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- UA78255C2 UA78255C2 UA20040604823A UA20040604823A UA78255C2 UA 78255 C2 UA78255 C2 UA 78255C2 UA 20040604823 A UA20040604823 A UA 20040604823A UA 20040604823 A UA20040604823 A UA 20040604823A UA 78255 C2 UA78255 C2 UA 78255C2
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- formula
- chloro
- alkyl
- haloalkyl
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 11
- LVXOXXGCJHYEOS-UHFFFAOYSA-N 5-phenylpyrimidine Chemical class C1=CC=CC=C1C1=CN=CN=C1 LVXOXXGCJHYEOS-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 239000000417 fungicide Substances 0.000 title claims description 13
- -1 sulphoxy Chemical group 0.000 claims abstract description 180
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 230000003993 interaction Effects 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 229910052740 iodine Inorganic materials 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 150000003457 sulfones Chemical class 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 241000233866 Fungi Species 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 230000003032 phytopathogenic effect Effects 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical class OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 claims 1
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 24
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000000262 haloalkenyl group Chemical group 0.000 abstract description 2
- 229910003827 NRaRb Inorganic materials 0.000 abstract 3
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 208000031888 Mycoses Diseases 0.000 abstract 1
- 125000005108 alkenylthio group Chemical group 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- 230000001473 noxious effect Effects 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 38
- 239000003921 oil Substances 0.000 description 27
- 239000002245 particle Substances 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 241000894007 species Species 0.000 description 14
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000003513 alkali Substances 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 235000013339 cereals Nutrition 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 240000008067 Cucumis sativus Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
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- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- MKWQJYNEKZKCSA-UHFFFAOYSA-N quinoxaline Chemical compound N1=C=C=NC2=CC=CC=C21 MKWQJYNEKZKCSA-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
- 150000005326 tetrahydropyrimidines Chemical class 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002023 wood Substances 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
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen 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
- C07D239/46—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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10156279 | 2001-11-19 | ||
| PCT/EP2002/012807 WO2003043993A1 (de) | 2001-11-19 | 2002-11-15 | 5-phenylpyrimidine, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA78255C2 true UA78255C2 (en) | 2007-03-15 |
Family
ID=7705956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604823A UA78255C2 (en) | 2001-11-19 | 2002-11-15 | 5-phenylpyrimidines, method of production thereof (variants), fungicidal agent containing thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7465735B2 (de) |
| EP (1) | EP1448532A1 (de) |
| JP (1) | JP4450625B2 (de) |
| KR (1) | KR100950632B1 (de) |
| CN (1) | CN1312134C (de) |
| AU (1) | AU2002352015B2 (de) |
| BR (1) | BR0214253A (de) |
| CA (1) | CA2467683C (de) |
| EA (1) | EA010628B1 (de) |
| HU (1) | HUP0402385A3 (de) |
| IL (1) | IL161893A0 (de) |
| MX (1) | MXPA04004583A (de) |
| NZ (1) | NZ533265A (de) |
| PL (1) | PL371059A1 (de) |
| UA (1) | UA78255C2 (de) |
| WO (1) | WO2003043993A1 (de) |
| ZA (1) | ZA200404835B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05011549A (es) * | 2003-05-20 | 2005-12-15 | Basf Ag | Pirimidinas 2 - sustituidas. |
| US7317015B2 (en) * | 2003-07-24 | 2008-01-08 | Basf Aktiengesellschaft | 2-Substituted pyrimidines |
| PL1651618T3 (pl) | 2003-07-24 | 2007-05-31 | Basf Se | 2-Podstawione pirymidyny |
| WO2005030216A1 (en) | 2003-09-24 | 2005-04-07 | Wyeth Holdings Corporation | 5-arylpyrimidines as anticancer agents |
| JP2005232081A (ja) * | 2004-02-19 | 2005-09-02 | Bayer Cropscience Ag | ベンジルピリミジン誘導体の農園芸用殺菌剤としての利用 |
| BRPI0510486A (pt) | 2004-05-19 | 2007-11-20 | Basf Ag | composto, processo para preparar o mesmo, agente pesticida, e, processo para combater fungos nocivos fitopatogênicos |
| DE502005002116D1 (de) | 2004-06-25 | 2008-01-10 | Basf Ag | 2, 4, 5, 6-substituierte pyridine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen |
| US20080132522A1 (en) * | 2004-07-14 | 2008-06-05 | Basf Aktiengesellschaft | 2-Substituted Pyrimidines, Method for Their Production and Their Use for Controlling Pathogenic Fungi |
| TW200637556A (en) * | 2005-01-31 | 2006-11-01 | Basf Ag | Substituted 5-phenyl pyrimidines I in therapy |
| TW200640881A (en) * | 2005-02-15 | 2006-12-01 | Du Pont | Fungicidal pyrazine derivatives |
| DE102005046592A1 (de) * | 2005-09-28 | 2007-03-29 | Basf Ag | 2-Substituierte Hydroxylaminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizid |
| WO2007054472A1 (de) * | 2005-11-11 | 2007-05-18 | Basf Se | Verhenkelte pyridin- und pyrimidinderivate, verfahren zu ihrer herstellung und ihre verwendung als pestizid |
| EP1987011A1 (de) * | 2006-02-15 | 2008-11-05 | Basf Se | 2-substituierte pyrimidine und ihre verwendung als pestizide |
| EP2001298A2 (de) * | 2006-03-27 | 2008-12-17 | Basf Se | Substituierte 5-hetaryl-4-aminopyrimidine |
| CL2007002231A1 (es) * | 2006-08-02 | 2008-04-11 | Basf Ag | Uso de compuestos derivados de 5-(het) arilpirimidina para combatir hongos daninos; compuestos derivados de 5-(het) arilpirimidina; agente fungicida; y agente farmaceutico. |
| WO2008107398A2 (en) * | 2007-03-02 | 2008-09-12 | Basf Se | Pyrazine compounds |
| US8981111B2 (en) * | 2008-04-22 | 2015-03-17 | Bayer Cropscience Ag | Fungicide hydroximoyl-heterocycles derivatives |
| US8912207B2 (en) * | 2009-12-17 | 2014-12-16 | Dow AgroSciences, LLP. | 2-aldoximino-5-fluoropyrimidine derivatives |
| AR081349A1 (es) | 2010-06-07 | 2012-08-08 | Dow Agrosciences Llc | Carboxamidas de pirazinilo como fungicidas |
| DK2595965T3 (en) * | 2010-07-20 | 2016-08-22 | Vestaron Corp | Insecticidal triazines and pyrimidines |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3919229A (en) * | 1973-07-19 | 1975-11-11 | Labaz | Pyrimidine derivatives and process for preparing the same |
| DE3620841A1 (de) * | 1986-06-21 | 1987-12-23 | Basf Ag | 4-aminopyrimidinderivate |
| DE3901084A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte 4-sulfonylamino-2-azinyl-1,2,4-triazol-3-one, verfahren sowie zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| FI895821A0 (fi) * | 1988-12-07 | 1989-12-05 | Wellcome Found | Farmaceutiskt aktiva cns foereningar. |
| JPH02200678A (ja) * | 1989-01-28 | 1990-08-08 | Kumiai Chem Ind Co Ltd | ２―ヨードプロパルギルオキシピリミジン誘導体及び農園芸用殺菌剤 |
| DE3922735A1 (de) | 1989-07-11 | 1991-01-24 | Hoechst Ag | Aminopyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| WO1992010490A1 (de) | 1990-12-05 | 1992-06-25 | Hoechst Aktiengesellschaft | Pyridyl-pyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
| DE4227811A1 (de) | 1992-08-21 | 1994-02-24 | Hoechst Ag | 2-Pyridyl-pyrimidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Fungizide |
| GB2277090A (en) | 1993-04-16 | 1994-10-19 | Shell Int Research | Fungicidal tetrahydropyrimidine and imidazoline derivatives |
| US6440965B1 (en) * | 1997-10-15 | 2002-08-27 | Krenitsky Pharmaceuticals, Inc. | Substituted pyrimidine derivatives, their preparation and their use in the treatment of neurodegenerative or neurological disorders of the central nervous system |
| DE60113104D1 (de) * | 2000-06-13 | 2005-10-06 | Basf Ag | 5 phenyl substituierte 2-(cyanoamino)-pyrimidine als fungizide |
| MXPA03008121A (es) | 2001-03-15 | 2003-12-12 | Basf Ag | 5-fenilpirimidinas, metodos y productos intermedios para su produccion y uso de las mismas para controlar hongos patogenicos. |
-
2002
- 2002-11-15 NZ NZ533265A patent/NZ533265A/en not_active IP Right Cessation
- 2002-11-15 BR BR0214253-8A patent/BR0214253A/pt not_active Application Discontinuation
- 2002-11-15 HU HU0402385A patent/HUP0402385A3/hu unknown
- 2002-11-15 KR KR1020047007560A patent/KR100950632B1/ko not_active IP Right Cessation
- 2002-11-15 JP JP2003545630A patent/JP4450625B2/ja not_active Expired - Fee Related
- 2002-11-15 CA CA2467683A patent/CA2467683C/en not_active Expired - Fee Related
- 2002-11-15 AU AU2002352015A patent/AU2002352015B2/en not_active Ceased
- 2002-11-15 US US10/495,280 patent/US7465735B2/en not_active Expired - Fee Related
- 2002-11-15 EP EP02787691A patent/EP1448532A1/de not_active Withdrawn
- 2002-11-15 UA UA20040604823A patent/UA78255C2/uk unknown
- 2002-11-15 EA EA200400597A patent/EA010628B1/ru not_active IP Right Cessation
- 2002-11-15 CN CNB028255356A patent/CN1312134C/zh not_active Expired - Fee Related
- 2002-11-15 MX MXPA04004583A patent/MXPA04004583A/es active IP Right Grant
- 2002-11-15 WO PCT/EP2002/012807 patent/WO2003043993A1/de active Application Filing
- 2002-11-15 IL IL16189302A patent/IL161893A0/xx unknown
- 2002-11-15 PL PL02371059A patent/PL371059A1/xx not_active Application Discontinuation
-
2004
- 2004-06-18 ZA ZA200404835A patent/ZA200404835B/en unknown
-
2007
- 2007-02-22 US US11/677,862 patent/US7449471B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1606547A (zh) | 2005-04-13 |
| EA010628B1 (ru) | 2008-10-30 |
| JP4450625B2 (ja) | 2010-04-14 |
| US20060148764A1 (en) | 2006-07-06 |
| US20070149551A1 (en) | 2007-06-28 |
| AU2002352015A1 (en) | 2003-06-10 |
| HUP0402385A3 (en) | 2005-10-28 |
| KR20040079901A (ko) | 2004-09-16 |
| MXPA04004583A (es) | 2004-08-13 |
| NZ533265A (en) | 2006-05-26 |
| CA2467683C (en) | 2011-09-27 |
| HUP0402385A2 (hu) | 2005-03-29 |
| EP1448532A1 (de) | 2004-08-25 |
| PL371059A1 (en) | 2005-06-13 |
| AU2002352015B2 (en) | 2008-07-31 |
| EA200400597A1 (ru) | 2004-12-30 |
| US7449471B2 (en) | 2008-11-11 |
| CN1312134C (zh) | 2007-04-25 |
| CA2467683A1 (en) | 2003-05-30 |
| BR0214253A (pt) | 2004-12-14 |
| US7465735B2 (en) | 2008-12-16 |
| WO2003043993A1 (de) | 2003-05-30 |
| JP2005514363A (ja) | 2005-05-19 |
| IL161893A0 (en) | 2005-11-20 |
| KR100950632B1 (ko) | 2010-04-01 |
| ZA200404835B (en) | 2005-06-20 |
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