HUT54280A - Fungicide comprising aminopyrimidine derivatives as active ingredient and process for producing the compounds - Google Patents
Fungicide comprising aminopyrimidine derivatives as active ingredient and process for producing the compounds Download PDFInfo
- Publication number
- HUT54280A HUT54280A HU904151A HU415190A HUT54280A HU T54280 A HUT54280 A HU T54280A HU 904151 A HU904151 A HU 904151A HU 415190 A HU415190 A HU 415190A HU T54280 A HUT54280 A HU T54280A
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- phenyl
- cycloalkyl
- substituted
- groups
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 34
- 239000004480 active ingredient Substances 0.000 title claims description 44
- 239000000417 fungicide Substances 0.000 title claims description 9
- 150000005005 aminopyrimidines Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 230000000855 fungicidal effect Effects 0.000 title abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 111
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 56
- -1 einen Rest R7R8N- Chemical group 0.000 claims abstract description 55
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
- 150000002367 halogens Chemical class 0.000 claims abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 12
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004660 phenylalkylthio group Chemical group 0.000 claims abstract description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 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 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract description 3
- 125000006193 alkinyl group Chemical group 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 210000002435 tendon Anatomy 0.000 description 111
- 241000196324 Embryophyta Species 0.000 description 29
- 230000000694 effects Effects 0.000 description 24
- 239000013543 active substance Substances 0.000 description 20
- 101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229920001817 Agar Polymers 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000008272 agar Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 7
- 230000002538 fungal effect Effects 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- 241000233866 Fungi Species 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000004575 stone Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000004888 barrier function Effects 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000010410 dusting Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 241000412366 Alternaria mali Species 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 241000221785 Erysiphales Species 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241001281805 Pseudoperonospora cubensis 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229960000892 attapulgite Drugs 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
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VZPRFNYMFQEGNV-UHFFFAOYSA-N naphthalen-2-ylmethyl cyclopropanecarboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC(=O)C1CC1 VZPRFNYMFQEGNV-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- YATDSXRLIUJOQN-SVRRBLITSA-N (2,3,4,5,6-pentafluorophenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=C(F)C(F)=C1F YATDSXRLIUJOQN-SVRRBLITSA-N 0.000 description 1
- MYUPFXPCYUISAG-UHFFFAOYSA-N (2,4-dichlorophenyl)(phenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC(Cl)=CC=1)Cl)(O)C1=CC=CC=C1 MYUPFXPCYUISAG-UHFFFAOYSA-N 0.000 description 1
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- QYOXAEWIVYMSGJ-CMPLNLGQSA-N (5s,6s)-6-hydroxy-2,2,7,7-tetramethyl-5-(1,2,4-triazol-1-yl)octan-3-one Chemical compound CC(C)(C)C(=O)C[C@@H]([C@@H](O)C(C)(C)C)N1C=NC=N1 QYOXAEWIVYMSGJ-CMPLNLGQSA-N 0.000 description 1
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 1
- AMLFJZRZIOZGPW-NSCUHMNNSA-N (e)-prop-1-en-1-amine Chemical group C\C=C\N AMLFJZRZIOZGPW-NSCUHMNNSA-N 0.000 description 1
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- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 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
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3922735A DE3922735A1 (de) | 1989-07-11 | 1989-07-11 | Aminopyrimidin-derivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als fungizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU904151D0 HU904151D0 (cg-RX-API-DMAC10.html) | 1990-12-28 |
| HUT54280A true HUT54280A (en) | 1991-02-28 |
Family
ID=6384711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU904151A HUT54280A (en) | 1989-07-11 | 1990-07-10 | Fungicide comprising aminopyrimidine derivatives as active ingredient and process for producing the compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5250530A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0407899B1 (cg-RX-API-DMAC10.html) |
| DE (2) | DE3922735A1 (cg-RX-API-DMAC10.html) |
| HU (1) | HUT54280A (cg-RX-API-DMAC10.html) |
| PT (1) | PT94645B (cg-RX-API-DMAC10.html) |
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| JPH06502147A (ja) * | 1990-10-09 | 1994-03-10 | ニューロゲン コーポレイション | 或る種のシクロアルキルおよびアザシクロアルキルピロロピリミジン；新規な種類のｇａｂａ脳リセプタリガンド |
| GB9024873D0 (en) * | 1990-11-15 | 1991-01-02 | Ici Plc | Fungicidal compounds |
| AU8931591A (en) * | 1990-12-05 | 1992-07-08 | Hoechst Aktiengesellschaft | Pyridyl-pyrimidin-derivates, process for producing the same, agents containing the same and their use as fungicides |
| DE4117560A1 (de) * | 1991-05-29 | 1992-12-03 | Bayer Ag | Verwendung von pyridinylpyrimidin-derivaten zum schutz technischer materialien |
| US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
| DE4206148A1 (de) * | 1992-02-28 | 1993-09-02 | Bayer Ag | Substituierte pyridylpyrimidine |
| JP2657760B2 (ja) * | 1992-07-15 | 1997-09-24 | 小野薬品工業株式会社 | ４−アミノキナゾリン誘導体およびそれを含有する医薬品 |
| DE69408750T2 (de) * | 1993-08-26 | 1998-07-23 | Ono Pharmaceutical Co | 4-Aminopyrimidin Derivate |
| US6410729B1 (en) | 1996-12-05 | 2002-06-25 | Amgen Inc. | Substituted pyrimidine compounds and methods of use |
| JPH11199564A (ja) * | 1997-09-12 | 1999-07-27 | American Cyanamid Co | 除草性２−アジニル−６−アリールオキシピリ（ミ）ジン |
| US6174901B1 (en) | 1998-12-18 | 2001-01-16 | Amgen Inc. | Substituted pyridine and pyridazine compounds and methods of use |
| DE19904710A1 (de) | 1999-02-05 | 2000-08-10 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-tetrahydrochinazoline, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
| FR2803592A1 (fr) * | 2000-01-06 | 2001-07-13 | Aventis Cropscience Sa | Nouveaux derives de l'acide 3-hydroxypicolinique, leur procede de preparation et compositions fongicides les contenant. |
| US6716851B2 (en) | 2000-12-12 | 2004-04-06 | Cytovia, Inc. | Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof |
| 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. |
| EP1254903B1 (en) * | 2001-04-20 | 2005-06-08 | Ciba SC Holding AG | 4-Amino-2-(pyridin-2-yl)pyrimidine as microbicidal active substances |
| ATE297390T1 (de) * | 2001-04-20 | 2005-06-15 | Ciba Sc Holding Ag | 4-amino-2-(2-pyridinyl)pyrimidine als mikrobizide wirksubstanzen |
| CA2345853A1 (en) | 2001-04-30 | 2002-10-30 | Minoru Katayama | Skiing facilities capable of changing shape of surface of ski slope and method for changing shape of surface of ski slope of skiing facilities |
| NZ533265A (en) | 2001-11-19 | 2006-05-26 | Basf Ag | 5-Phenylpyrimidines, their preparation, compositions comprising them and their use |
| EP1504001B1 (de) * | 2002-02-21 | 2009-04-15 | Basf Se | 2-(2-pyridyl)-5-phenyl-6-aminopyrimidine, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen |
| CN1642422A (zh) | 2002-03-15 | 2005-07-20 | 西巴特殊化学品控股有限公司 | 4－氨基嘧啶及其在表面抗菌处理中的应用 |
| MXPA04012577A (es) | 2002-07-31 | 2005-03-23 | Ciba Sc Holding Ag | Derivados de piridin-triacina como sustancias microbicidas activas. |
| AU2003288994A1 (en) * | 2002-12-10 | 2004-06-30 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
| JP2006518717A (ja) * | 2003-02-06 | 2006-08-17 | ビーエーエスエフ アクチェンゲゼルシャフト | ピリミジン類、製造およびそれの使用 |
| WO2004094379A2 (en) * | 2003-04-16 | 2004-11-04 | Amgen Inc. | 3-phenyl-4- (pyrimidin-2-yl) -6- (piperidin-4-yl) derivatives and related compounds as tnf-alpha and il-1 inhibitors for the treatment of inflammations |
| TWI312272B (en) * | 2003-05-12 | 2009-07-21 | Sumitomo Chemical Co | Pyrimidine compound and pests controlling composition containing the same |
| JP4595381B2 (ja) * | 2003-05-12 | 2010-12-08 | 住友化学株式会社 | ピリミジン化合物及びその有害生物防除用途 |
| KR20060118398A (ko) * | 2003-08-05 | 2006-11-23 | 버텍스 파마슈티칼스 인코포레이티드 | 전압 개폐 이온 채널 억제제로서의 축합 피라미딘 화합물 |
| US6818631B1 (en) * | 2003-08-15 | 2004-11-16 | Nippon Soda Co. Ltd. | Fungicidal pyrimidine derivatives |
| US20050038041A1 (en) * | 2003-08-15 | 2005-02-17 | Yuki Nakagawa | Fungicidal pyrimidine derivatives |
| ES2234433B1 (es) * | 2003-12-15 | 2006-11-01 | Almirall Prodesfarma, S.A. | 4-aminopirimidinas como antagonistas de receptores de adenosina. |
| DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
| 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 |
| TW200538180A (en) * | 2004-02-20 | 2005-12-01 | Astrazeneca Ab | New compounds |
| 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 |
| WO2006005571A1 (de) * | 2004-07-14 | 2006-01-19 | Basf Aktiengesellschaft | 2-substituierte pyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen |
| US20070293395A1 (en) * | 2004-09-17 | 2007-12-20 | Basf Aktiengesellschaft | Use of 2-Substituted Pyrimidines for Combating Nematode Diseases of Plants |
| MX2007002980A (es) * | 2004-09-23 | 2007-05-16 | Basf Ag | Uso de pirimidinas 2 - sustituidas para combatir nematodos de plantas. |
| JP2006188462A (ja) * | 2005-01-07 | 2006-07-20 | Ube Ind Ltd | ４−（ホモ）ピペラジニルピリミジン誘導体及び抗菌剤 |
| US20060178388A1 (en) * | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| BRPI0608411A2 (pt) * | 2005-03-10 | 2009-12-29 | Basf Ag | uso de um composto, composto, processo para preparar compostos, agente, semente, e, processo para combater fungos nocivos fitopatogênicos |
| WO2007063935A1 (ja) * | 2005-12-02 | 2007-06-07 | Mitsubishi Tanabe Pharma Corporation | 芳香族化合物 |
| EP1979325A1 (en) * | 2006-01-11 | 2008-10-15 | AstraZeneca AB | Morpholino pyrimidine derivatives and their use in therapy |
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| US9315491B2 (en) * | 2009-12-28 | 2016-04-19 | Development Center For Biotechnology | Pyrimidine compounds as mTOR and PI3K inhibitors |
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| JP7651590B2 (ja) * | 2020-03-27 | 2025-03-26 | ドン－ア エスティ カンパニー リミテッド | アミノピリミジン誘導体およびアリール炭化水素受容体モジュレーターとしてのその使用 |
| KR20230007441A (ko) * | 2020-04-28 | 2023-01-12 | 글로벌 블러드 테라퓨틱스, 인크. | 페로포르틴 억제제로서의 시클로알킬 피리미딘 |
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| US4109092A (en) * | 1976-10-07 | 1978-08-22 | Sterling Drug Inc. | Preparation of 2-(pyridinyl)-4-pyrimidinamines |
| DE3675197D1 (de) * | 1985-12-03 | 1990-11-29 | Sumitomo Chemical Co | Pyridinylpyrimidin-derivate, verfahren zu deren herstellung und diese als wirksamen stoff enthaltende pflanzenkrankheiten-schutzmittel. |
| PH23565A (en) * | 1986-09-05 | 1989-08-25 | Sumitomo Chemical Co | Novel pyrimidinylpyrimidine derivatives and a plant disease protectant containing them as the active ingredient |
| CA1288433C (en) * | 1986-12-03 | 1991-09-03 | Tsuguhiro Katoh | Pyridinylpyrimidine derivatives, method for production thereof and a fungicide containing them as the active ingredient |
-
1989
- 1989-07-11 DE DE3922735A patent/DE3922735A1/de not_active Withdrawn
-
1990
- 1990-07-06 EP EP90112903A patent/EP0407899B1/de not_active Expired - Lifetime
- 1990-07-06 DE DE59008571T patent/DE59008571D1/de not_active Expired - Fee Related
- 1990-07-09 US US07/549,764 patent/US5250530A/en not_active Expired - Fee Related
- 1990-07-10 HU HU904151A patent/HUT54280A/hu unknown
- 1990-07-10 PT PT94645A patent/PT94645B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3922735A1 (de) | 1991-01-24 |
| US5250530A (en) | 1993-10-05 |
| PT94645B (pt) | 1997-02-28 |
| PT94645A (pt) | 1991-03-20 |
| EP0407899B1 (de) | 1995-03-01 |
| EP0407899A2 (de) | 1991-01-16 |
| HU904151D0 (cg-RX-API-DMAC10.html) | 1990-12-28 |
| EP0407899A3 (en) | 1991-07-24 |
| DE59008571D1 (de) | 1995-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFA9 | Temporary prot. cancelled due to abandonment |