CA2162846A1 - Fungicidal fused bicyclic pyrimidinones - Google Patents
Fungicidal fused bicyclic pyrimidinonesInfo
- Publication number
- CA2162846A1 CA2162846A1 CA002162846A CA2162846A CA2162846A1 CA 2162846 A1 CA2162846 A1 CA 2162846A1 CA 002162846 A CA002162846 A CA 002162846A CA 2162846 A CA2162846 A CA 2162846A CA 2162846 A1 CA2162846 A1 CA 2162846A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- haloalkyl
- cycloalkyl
- alkynyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- -1 bicyclic pyrimidinones Chemical class 0.000 title claims description 87
- 230000000855 fungicidal effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 211
- 125000001246 bromo group Chemical group Br* 0.000 claims description 145
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
- 125000001188 haloalkyl group Chemical group 0.000 claims description 78
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 150000002367 halogens Chemical group 0.000 claims description 52
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 39
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 36
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000001544 thienyl group Chemical group 0.000 claims description 30
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000004001 thioalkyl group Chemical group 0.000 claims description 27
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 26
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 19
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 14
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 239000011630 iodine Substances 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 125000004971 nitroalkyl group Chemical group 0.000 claims description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 241000209140 Triticum Species 0.000 claims description 7
- 235000021307 Triticum Nutrition 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000001843 C4-C10 alkenyl group Chemical group 0.000 claims description 5
- 241000221785 Erysiphales Species 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 4
- 244000000004 fungal plant pathogen Species 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000005082 alkoxyalkenyl group Chemical group 0.000 claims 19
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 19
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 15
- 125000001624 naphthyl group Chemical group 0.000 claims 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 11
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 10
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 6
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 6
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000005109 alkynylthio group Chemical group 0.000 claims 3
- 125000006226 butoxyethyl group Chemical group 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- KZPLPWDFXMJJPD-UHFFFAOYSA-N 2-anilino-6,8-diiodo-3-propylquinazolin-4-one Chemical compound N=1C2=C(I)C=C(I)C=C2C(=O)N(CCC)C=1NC1=CC=CC=C1 KZPLPWDFXMJJPD-UHFFFAOYSA-N 0.000 claims 1
- QQLGQHGKSPJXTO-UHFFFAOYSA-N 6,8-diiodo-2-propoxy-3-propylquinazolin-4-one Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1I QQLGQHGKSPJXTO-UHFFFAOYSA-N 0.000 claims 1
- CGVCBPKQFKNLDR-UHFFFAOYSA-N 6-bromo-3-(cyclopropylmethyl)-2-propoxyquinazolin-4-one Chemical compound CCCOC1=NC2=CC=C(Br)C=C2C(=O)N1CC1CC1 CGVCBPKQFKNLDR-UHFFFAOYSA-N 0.000 claims 1
- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 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
- 239000000417 fungicide Substances 0.000 abstract description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 102
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 25
- 239000003921 oil Substances 0.000 description 24
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 12
- 125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 7
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 239000012677 causal agent Substances 0.000 description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- 241000282320 Panthera leo Species 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- RYVLOOXFFIFQEN-UHFFFAOYSA-N n-[4-(1-oxo-3,4-dihydro-2h-pyrido[4,3-b]indol-5-yl)butyl]acetamide Chemical compound C12=CC=CC=C2N(CCCCNC(=O)C)C2=C1C(=O)NCC2 RYVLOOXFFIFQEN-UHFFFAOYSA-N 0.000 description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
- 244000052769 pathogen Species 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products 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 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- KKASGUHLXWAKEZ-UHFFFAOYSA-N 1-isothiocyanatopropane Chemical compound CCCN=C=S KKASGUHLXWAKEZ-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 2
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical compound [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 2
- PUMRUSBKNSBTAL-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-2-carbaldehyde Chemical compound C1=CC=C2OC(C=O)CCC2=C1 PUMRUSBKNSBTAL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000895502 Blumeria graminis f. sp. tritici Species 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 241000183583 Cymo Species 0.000 description 2
- 239000005757 Cyproconazole Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 239000005802 Mancozeb Substances 0.000 description 2
- 241000080590 Niso Species 0.000 description 2
- 241000233622 Phytophthora infestans Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 241001123569 Puccinia recondita Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- WPOOICLZIIBUBM-UHFFFAOYSA-H iron;iron(3+);methyl-dioxido-oxo-$l^{5}-arsane Chemical compound [Fe].[Fe+3].[Fe+3].C[As]([O-])([O-])=O.C[As]([O-])([O-])=O.C[As]([O-])([O-])=O WPOOICLZIIBUBM-UHFFFAOYSA-H 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
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- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 description 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- MGCQZNBCJBRZDT-UHFFFAOYSA-N midodrine hydrochloride Chemical compound [H+].[Cl-].COC1=CC=C(OC)C(C(O)CNC(=O)CN)=C1 MGCQZNBCJBRZDT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- HUPKWBBKMAGWFY-UHFFFAOYSA-N octa-1,6-diyne Chemical compound CC#CCCCC#C HUPKWBBKMAGWFY-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000003090 pesticide formulation Substances 0.000 description 1
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- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-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
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 102200073741 rs121909602 Human genes 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 239000000021 stimulant Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 150000003512 tertiary amines Chemical group 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
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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
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6062993A | 1993-05-12 | 1993-05-12 | |
| US08/060,629 | 1993-05-12 | ||
| US14490493A | 1993-10-28 | 1993-10-28 | |
| US08/144,904 | 1993-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2162846A1 true CA2162846A1 (en) | 1994-11-24 |
Family
ID=26740142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002162846A Abandoned CA2162846A1 (en) | 1993-05-12 | 1994-05-10 | Fungicidal fused bicyclic pyrimidinones |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US5747497A (en, 2012) |
| EP (1) | EP0698013B1 (en, 2012) |
| JP (1) | JPH08510243A (en, 2012) |
| CN (1) | CN1050355C (en, 2012) |
| AT (1) | ATE206406T1 (en, 2012) |
| AU (1) | AU6944394A (en, 2012) |
| BR (1) | BR9406662A (en, 2012) |
| CA (1) | CA2162846A1 (en, 2012) |
| CZ (1) | CZ291264B6 (en, 2012) |
| DE (1) | DE69428533T2 (en, 2012) |
| DK (1) | DK0698013T3 (en, 2012) |
| ES (1) | ES2163445T3 (en, 2012) |
| FR (1) | FR09C0038I2 (en, 2012) |
| GR (1) | GR3036942T3 (en, 2012) |
| HU (1) | HU218381B (en, 2012) |
| LV (1) | LV11464B (en, 2012) |
| NZ (1) | NZ267222A (en, 2012) |
| PL (1) | PL174704B1 (en, 2012) |
| PT (1) | PT698013E (en, 2012) |
| RU (1) | RU2139862C1 (en, 2012) |
| SI (1) | SI9420029A (en, 2012) |
| SK (1) | SK140295A3 (en, 2012) |
| WO (1) | WO1994026722A1 (en, 2012) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK140295A3 (en) * | 1993-05-12 | 1996-09-04 | Du Pont | Condensed bicyclic pyrimidinones, fungicidal agents on their base and inhibition method of plant deseases by using them |
| USH1829H (en) * | 1994-11-02 | 2000-01-04 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| WO1996020178A1 (en) * | 1994-12-27 | 1996-07-04 | Warner-Lambert Company | Novel heterocycles as cholecystokinin (cck) ligands |
| EP0836602B1 (en) * | 1995-07-05 | 2002-01-30 | E.I. Du Pont De Nemours And Company | Fungicidal pyrimidinones |
| US6897213B1 (en) | 1995-11-21 | 2005-05-24 | Warner-Lambert Company | Heterocycles as cholecystokinin (CCK) ligands |
| CZ288498A3 (cs) | 1996-03-11 | 1998-12-16 | Novartis Ag | Deriváty pyrimidin-4-onu jako pesticidní látky, způsob jejich přípravy a agrochemické prostředky, které je obsahují |
| EP1344775B1 (en) * | 1996-06-18 | 2006-11-29 | E.I. Du Pont De Nemours And Company | Preparation of fungicidal quinazolinones and useful intermediates |
| TW434228B (en) * | 1996-06-18 | 2001-05-16 | Du Pont | Preparation of fungicidal quinazolinones and useful intermediates |
| BR9714222A (pt) * | 1996-12-17 | 2000-04-18 | Du Pont | Método para o controle de doenças de plantas |
| EP1310169A3 (en) * | 1997-01-30 | 2003-08-27 | E.I. Du Pont De Nemours And Company | Fungicidal mixture |
| ZA9711323B (en) * | 1997-01-30 | 1999-06-17 | I E Du Pont De Nemours And Com | Fungicidal mixtures |
| WO1998040363A1 (de) * | 1997-03-07 | 1998-09-17 | Lonza Ag | Verfahren zur herstellung von chinazol-4-onen |
| GB9718737D0 (en) | 1997-09-04 | 1997-11-12 | Ciba Geigy Ag | Pesticide |
| GB9719411D0 (en) * | 1997-09-12 | 1997-11-12 | Ciba Geigy Ag | New Pesticides |
| EP1035774A1 (en) * | 1997-12-01 | 2000-09-20 | Novartis AG | Fungicidal combinations comprising quinazolinone |
| US6255311B1 (en) * | 1998-01-14 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| GB9802355D0 (en) | 1998-02-04 | 1998-04-01 | Ciba Geigy Ag | Organic compounds |
| WO1999067202A1 (en) * | 1998-06-19 | 1999-12-29 | Syngenta Participations Ag . | Process for preparation of pyrimidinone derivatives |
| US6337332B1 (en) * | 1998-09-17 | 2002-01-08 | Pfizer Inc. | Neuropeptide Y receptor antagonists |
| GB9827162D0 (en) * | 1998-12-10 | 1999-02-03 | Novartis Ag | Organic compounds |
| WO2000051992A1 (en) * | 1999-03-04 | 2000-09-08 | E.I. Du Pont De Nemours And Company | Fused bicyclic oxazinone and thiazinone fungicides |
| CO5170526A1 (es) * | 1999-05-28 | 2002-06-27 | Smithkline Beecham Corp | Nuevos compuestos de guanidina ciclica utiles como antagonis tas del receptor de la il-8 |
| DE60121695T2 (de) | 2000-02-22 | 2007-08-30 | Daiichi Asubio Pharma Co., Ltd. | Arzneimittel mit chymaseinhibitoren als wirksames mittel zur behandlung von dermatitis mit zweiphasigen hautreaktionen |
| CN1245978C (zh) | 2000-02-22 | 2006-03-22 | 第一阿斯比奥制药株式会社 | 含有胃促胰酶抑制剂作为活性成分的预防和治疗各种与嗜酸性粒细胞增多有关的疾病的药物 |
| US20040033555A1 (en) * | 2001-07-20 | 2004-02-19 | Shawn Louise Anderson | Methods using light emission for determining the effeciveness of plant treatment agents in controlling plant disease organisms |
| TW200306155A (en) | 2002-03-19 | 2003-11-16 | Du Pont | Benzamides and advantageous compositions thereof for use as fungicides |
| KR100967280B1 (ko) * | 2002-06-11 | 2010-07-01 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 흰가루병을 방제하는데 유용한 융합된 피리미디논과디니트로페놀 화합물의 혼합물 |
| ES2274242T3 (es) * | 2002-06-11 | 2007-05-16 | E.I. Du Pont De Nemours And Company | Mezclas de pirimidinonas combinadas y compuestos dinitrofenolicos utiles para controlar el moho. |
| EP1407774A1 (en) * | 2002-09-10 | 2004-04-14 | LION Bioscience AG | 2-Amino-4-quinazolinones as LXR nuclear receptor binding compounds |
| AU2003278066A1 (en) * | 2002-10-28 | 2004-05-25 | Basf Aktiengesellschaft | Fungicide mixtures containing oxazinone |
| GB0227555D0 (en) * | 2002-11-26 | 2002-12-31 | Syngenta Ltd | Fungicides |
| DE60335028D1 (de) * | 2002-12-23 | 2010-12-30 | Icagen Inc | Quinazolinone als kaliumkanalmodulatoren |
| RU2275362C2 (ru) * | 2004-05-14 | 2006-04-27 | Петр Сергеевич Хохлов | 3-гидрокси-2-тиоксо-4(3н)-хиназолинон, обладающий фунгицидными и росторегулирующими свойствами, и способ его получения |
| GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
| GB0422401D0 (en) | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
| GB0426373D0 (en) * | 2004-12-01 | 2005-01-05 | Syngenta Ltd | Fungicides |
| AR053563A1 (es) * | 2005-03-21 | 2007-05-09 | Basf Ag | Mezclas insecticidas |
| DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| KR20080018943A (ko) | 2005-06-09 | 2008-02-28 | 바이엘 크롭사이언스 아게 | 활성 물질 배합물 |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
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-
1994
- 1994-05-10 SK SK1402-95A patent/SK140295A3/sk unknown
- 1994-05-10 HU HU9503173A patent/HU218381B/hu active Protection Beyond IP Right Term
- 1994-05-10 AU AU69443/94A patent/AU6944394A/en not_active Abandoned
- 1994-05-10 EP EP94917917A patent/EP0698013B1/en not_active Expired - Lifetime
- 1994-05-10 CN CN94192068A patent/CN1050355C/zh not_active Expired - Lifetime
- 1994-05-10 DE DE69428533T patent/DE69428533T2/de not_active Expired - Lifetime
- 1994-05-10 PT PT94917917T patent/PT698013E/pt unknown
- 1994-05-10 CA CA002162846A patent/CA2162846A1/en not_active Abandoned
- 1994-05-10 JP JP6525540A patent/JPH08510243A/ja active Pending
- 1994-05-10 ES ES94917917T patent/ES2163445T3/es not_active Expired - Lifetime
- 1994-05-10 CZ CZ19952803A patent/CZ291264B6/cs not_active IP Right Cessation
- 1994-05-10 BR BR9406662A patent/BR9406662A/pt not_active Application Discontinuation
- 1994-05-10 PL PL94311641A patent/PL174704B1/pl unknown
- 1994-05-10 RU RU95121800A patent/RU2139862C1/ru active Protection Beyond IP Right Term
- 1994-05-10 AT AT94917917T patent/ATE206406T1/de active
- 1994-05-10 WO PCT/US1994/004965 patent/WO1994026722A1/en active IP Right Grant
- 1994-05-10 US US08/545,827 patent/US5747497A/en not_active Expired - Lifetime
- 1994-05-10 DK DK94917917T patent/DK0698013T3/da active
- 1994-05-10 SI SI9420029A patent/SI9420029A/sl unknown
- 1994-05-10 NZ NZ267222A patent/NZ267222A/en not_active IP Right Cessation
-
1995
- 1995-11-10 LV LVP-95-339A patent/LV11464B/en unknown
-
1998
- 1998-01-14 US US09/007,336 patent/US5945423A/en not_active Expired - Lifetime
-
2001
- 2001-10-18 GR GR20010401811T patent/GR3036942T3/el unknown
-
2009
- 2009-08-14 FR FR09C0038C patent/FR09C0038I2/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN1050355C (zh) | 2000-03-15 |
| BR9406662A (pt) | 1996-02-06 |
| PL174704B1 (pl) | 1998-09-30 |
| LV11464A (lv) | 1996-08-20 |
| HU9503173D0 (en) | 1995-12-28 |
| DE69428533D1 (de) | 2001-11-08 |
| US5747497A (en) | 1998-05-05 |
| JPH08510243A (ja) | 1996-10-29 |
| NZ267222A (en) | 1996-10-28 |
| HU218381B (hu) | 2000-08-28 |
| HUT72829A (en) | 1996-05-28 |
| ES2163445T3 (es) | 2002-02-01 |
| CN1123028A (zh) | 1996-05-22 |
| AU6944394A (en) | 1994-12-12 |
| WO1994026722A1 (en) | 1994-11-24 |
| FR09C0038I2 (en, 2012) | 2010-06-11 |
| DK0698013T3 (da) | 2001-12-10 |
| RU2139862C1 (ru) | 1999-10-20 |
| PT698013E (pt) | 2002-01-30 |
| FR09C0038I1 (en, 2012) | 2009-09-25 |
| LV11464B (en) | 1997-02-20 |
| CZ291264B6 (cs) | 2003-01-15 |
| ATE206406T1 (de) | 2001-10-15 |
| CZ280395A3 (en) | 1996-03-13 |
| EP0698013B1 (en) | 2001-10-04 |
| PL311641A1 (en) | 1996-03-04 |
| SK140295A3 (en) | 1996-09-04 |
| EP0698013A1 (en) | 1996-02-28 |
| SI9420029A (en) | 1996-10-31 |
| US5945423A (en) | 1999-08-31 |
| GR3036942T3 (en) | 2002-01-31 |
| DE69428533T2 (de) | 2002-05-23 |
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