NZ503261A - Fungicidal pyrimidin-4-one and pyrimidin-4-thione derivatives - Google Patents
Fungicidal pyrimidin-4-one and pyrimidin-4-thione derivativesInfo
- Publication number
- NZ503261A NZ503261A NZ503261A NZ50326198A NZ503261A NZ 503261 A NZ503261 A NZ 503261A NZ 503261 A NZ503261 A NZ 503261A NZ 50326198 A NZ50326198 A NZ 50326198A NZ 503261 A NZ503261 A NZ 503261A
- Authority
- NZ
- New Zealand
- Prior art keywords
- propyl
- butyl
- mono
- pentyl
- phenyl
- Prior art date
Links
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title claims abstract description 8
- MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical class SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000000855 fungicidal effect Effects 0.000 title description 5
- -1 C1-C6alkoxy Chemical group 0.000 claims abstract description 237
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 147
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 55
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 51
- 150000002367 halogens Chemical group 0.000 claims abstract description 49
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 36
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 34
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 18
- 206010061217 Infestation Diseases 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 8
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 6
- 244000005700 microbiome Species 0.000 claims abstract description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 75
- 241001070944 Mimosa Species 0.000 claims description 75
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 68
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 62
- 229910052794 bromium Inorganic materials 0.000 claims description 62
- 239000000460 chlorine Substances 0.000 claims description 61
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 60
- 239000011737 fluorine Substances 0.000 claims description 49
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 47
- 241000196324 Embryophyta Species 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 44
- 125000001153 fluoro group Chemical group F* 0.000 claims description 30
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
- 239000011630 iodine Substances 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 239000007921 spray Substances 0.000 claims description 9
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- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
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- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 208000024891 symptom Diseases 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
- 241000510928 Erysiphe necator Species 0.000 claims 1
- 229920003266 Leaf® Polymers 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 241000233866 Fungi Species 0.000 abstract description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 205
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 196
- 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 157
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 37
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 238000010992 reflux Methods 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 14
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- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- 239000000969 carrier Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
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- 239000000417 fungicide Substances 0.000 description 5
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- JCAWJAGCULLMRW-UHFFFAOYSA-N 2-butyl-6-chloro-3-propylthieno[2,3-d]pyrimidin-4-one Chemical compound O=C1N(CCC)C(CCCC)=NC2=C1C=C(Cl)S2 JCAWJAGCULLMRW-UHFFFAOYSA-N 0.000 description 4
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- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
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- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-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
- 244000045561 useful plants Species 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/92—Oxygen atoms with hetero atoms directly attached to nitrogen atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9719411.2A GB9719411D0 (en) | 1997-09-12 | 1997-09-12 | New Pesticides |
| PCT/EP1998/005790 WO1999014202A2 (en) | 1997-09-12 | 1998-09-10 | Novel pyrimidin-4-one and pyrimidin-4-thione as fungicide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ503261A true NZ503261A (en) | 2002-03-28 |
Family
ID=10818960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ503261A NZ503261A (en) | 1997-09-12 | 1998-09-10 | Fungicidal pyrimidin-4-one and pyrimidin-4-thione derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6277858B1 (https=) |
| EP (1) | EP1015434B1 (https=) |
| JP (1) | JP2001516749A (https=) |
| KR (1) | KR100585571B1 (https=) |
| CN (1) | CN1270593A (https=) |
| AR (1) | AR015439A1 (https=) |
| AT (1) | ATE216370T1 (https=) |
| AU (1) | AU743717B2 (https=) |
| BR (1) | BR9812439A (https=) |
| CA (1) | CA2301694A1 (https=) |
| DE (1) | DE69804981T2 (https=) |
| DK (1) | DK1015434T3 (https=) |
| EG (1) | EG22051A (https=) |
| ES (1) | ES2175804T3 (https=) |
| GB (1) | GB9719411D0 (https=) |
| GT (1) | GT199800142A (https=) |
| HN (1) | HN1998000139A (https=) |
| HU (1) | HUP0002423A3 (https=) |
| IL (1) | IL134779A0 (https=) |
| NZ (1) | NZ503261A (https=) |
| PL (1) | PL339053A1 (https=) |
| PT (1) | PT1015434E (https=) |
| TR (1) | TR200000713T2 (https=) |
| TW (1) | TW429254B (https=) |
| WO (1) | WO1999014202A2 (https=) |
| ZA (1) | ZA988336B (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9809598A (pt) * | 1997-05-08 | 2000-07-04 | Agrevo Uk Ltd | Uso de compostos, e, composto. |
| GT199900185A (es) | 1998-11-06 | 2001-04-18 | Novedosa pirimidin-4-enamina como fungicida. | |
| GB9824331D0 (en) * | 1998-11-06 | 1998-12-30 | Novartis Ag | Organic compounds |
| GB0021786D0 (en) * | 2000-09-05 | 2000-10-18 | Zeneca Ltd | Fungicidal formulations |
| AU2002227243A1 (en) * | 2000-12-11 | 2002-06-24 | E.I. Du Pont De Nemours And Company | Quinazolinones and pyridinopyrimidinones for controlling invertebrate pests |
| 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 |
| PT1511380E (pt) * | 2002-06-11 | 2006-12-29 | Du Pont | Mistura de pirimidinonas fundidas e compostos dinitrofenólicos úteis para controlar oídios |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| CN1898254A (zh) * | 2003-10-30 | 2007-01-17 | 马萨诸塞州立大学 | 肽合成的新偶联剂 |
| WO2005061518A1 (en) * | 2003-12-19 | 2005-07-07 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2007517066A (ja) * | 2003-12-31 | 2007-06-28 | サイオス・インコーポレーテツド | ピリドピリミドンの製造方法 |
| DE102004049761A1 (de) | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| CN104170838B (zh) | 2005-06-09 | 2016-03-30 | 拜尔农作物科学股份公司 | 活性物质结合物 |
| CN100335481C (zh) * | 2005-10-11 | 2007-09-05 | 华中师范大学 | 一类具有杀菌除草活性的多取代吡啶并[4,3－d]嘧啶及制备 |
| DE102006023263A1 (de) * | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| CL2007003256A1 (es) | 2006-11-15 | 2008-07-25 | Du Pont | Mezcla fungicida que comprende al menos tres compuestos diferentes; composicion fungicida que comprende dicha mezcla; y metodo para controlar una enfermedad en plantas causada por el patogeno fungico vegetal que comprende aplicar una cantidad de la m |
| JP5337711B2 (ja) | 2007-01-25 | 2013-11-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性アミド |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| US8349870B2 (en) | 2008-01-25 | 2013-01-08 | E I Du Pont De Nemours And Company | Fungicidal hetercyclic compounds |
| CN101531638B (zh) * | 2008-03-13 | 2011-12-28 | 中国科学院广州生物医药与健康研究院 | 用作雌激素相关受体调节剂的化合物及其应用 |
| CN101628913B (zh) * | 2008-07-18 | 2013-01-23 | 中国科学院广州生物医药与健康研究院 | 用作雌激素相关受体调节剂的化合物及其应用 |
| AU2009322486A1 (en) | 2008-12-02 | 2010-06-10 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic compounds |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
| WO2010108507A2 (de) | 2009-03-25 | 2010-09-30 | Bayer Cropscience Ag | Synergistische wirkstoffkombinationen |
| CN102510721B (zh) | 2009-07-16 | 2014-11-19 | 拜尔农作物科学股份公司 | 含苯基三唑的协同活性物质结合物 |
| EP2462120A1 (en) | 2009-08-07 | 2012-06-13 | E. I. du Pont de Nemours and Company | Fungicidal diphenyl-substituted pyridazines |
| TW201116212A (en) | 2009-10-29 | 2011-05-16 | Du Pont | Heterobicycle-substituted azolyl benzene fungicides |
| WO2011051958A1 (en) | 2009-10-30 | 2011-05-05 | E.I. Du Pont De Nemours And Company | Fungicidal pyrazolones |
| BR112012016733A2 (pt) | 2010-01-07 | 2015-09-01 | Du Pont | "composto, composição fungicida e método" |
| CN102285971B (zh) * | 2010-06-21 | 2013-12-18 | 中国中化股份有限公司 | 吡唑基喹唑啉酮类化合物及其应用 |
| WO2012023143A1 (en) | 2010-08-19 | 2012-02-23 | E. I. Du Pont De Nemours And Company | Fungicidal pyrazoles |
| CN103130730B (zh) * | 2011-11-24 | 2015-04-08 | 南开大学 | 喹唑啉类衍生物及其制备方法、抗hiv活性和抗tmv活性 |
| CN104151255B (zh) * | 2014-07-22 | 2016-07-13 | 清华大学 | 一种多取代喹唑啉亚胺衍生物及其制备方法 |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| JP7114076B2 (ja) | 2015-12-22 | 2022-08-08 | シャイ・セラピューティクス・エルエルシー | がん及び炎症性疾患の処置のための化合物 |
| WO2017207395A1 (en) | 2016-06-02 | 2017-12-07 | Bayer Cropscience Aktiengesellschaft | Isothiazolopyridones, processes for their preparation and their use as fungicides |
| EP3464296B1 (en) | 2016-06-02 | 2020-10-14 | Bayer CropScience Aktiengesellschaft | Isothiazolopyridones, processes for their preparation and their use as herbicides and/or plant growth regulators |
| PL3529246T3 (pl) | 2016-10-24 | 2024-03-25 | Fmc Corporation | Oksadiazole o działaniu grzybobójczym |
| JP7514005B2 (ja) | 2017-06-21 | 2024-07-10 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ラソパシー、及び線維性疾患の治療のためのｒａｓスーパーファミリーと相互作用する化合物 |
| JP7407461B2 (ja) | 2018-12-19 | 2024-01-04 | シャイ・セラピューティクス・エルエルシー | がん、炎症性疾患、ｒａｓ病、及び線維性疾患の処置のためのｒａｓスーパーファミリーと相互作用する化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3714354A (en) * | 1971-07-06 | 1973-01-30 | Pfizer | Bronchodilator activity of substituted quinazolinecarboxylic acid esters |
| BE793594A (fr) * | 1972-01-03 | 1973-07-02 | Pfizer | Nouvelles 6,7-dimethoxyquinazolines utiles comme analgesiques et tranquillisants |
| GB8820129D0 (en) * | 1988-08-24 | 1988-09-28 | Schering Agrochemicals Ltd | Fungicides |
| 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 |
| US5610301A (en) * | 1993-07-01 | 1997-03-11 | American Cyanamid Company | Process for the regioselective n-alkylation of quinazolinones |
| BR9609613A (pt) * | 1995-07-05 | 1999-05-25 | Du Pont | Composto composição fungicida e método de controle de doenças de plantas |
| BR9809598A (pt) * | 1997-05-08 | 2000-07-04 | Agrevo Uk Ltd | Uso de compostos, e, composto. |
-
1997
- 1997-09-12 GB GBGB9719411.2A patent/GB9719411D0/en not_active Ceased
-
1998
- 1998-08-25 TW TW087114037A patent/TW429254B/zh not_active IP Right Cessation
- 1998-09-08 HN HN1998000139A patent/HN1998000139A/es unknown
- 1998-09-09 GT GT199800142A patent/GT199800142A/es unknown
- 1998-09-10 IL IL13477998A patent/IL134779A0/xx unknown
- 1998-09-10 PT PT98951380T patent/PT1015434E/pt unknown
- 1998-09-10 DK DK98951380T patent/DK1015434T3/da active
- 1998-09-10 WO PCT/EP1998/005790 patent/WO1999014202A2/en not_active Ceased
- 1998-09-10 BR BR9812439-0A patent/BR9812439A/pt not_active IP Right Cessation
- 1998-09-10 US US09/508,307 patent/US6277858B1/en not_active Expired - Lifetime
- 1998-09-10 ES ES98951380T patent/ES2175804T3/es not_active Expired - Lifetime
- 1998-09-10 CA CA002301694A patent/CA2301694A1/en not_active Abandoned
- 1998-09-10 KR KR1020007002578A patent/KR100585571B1/ko not_active Expired - Fee Related
- 1998-09-10 PL PL98339053A patent/PL339053A1/xx unknown
- 1998-09-10 NZ NZ503261A patent/NZ503261A/en unknown
- 1998-09-10 AR ARP980104519A patent/AR015439A1/es not_active Application Discontinuation
- 1998-09-10 TR TR2000/00713T patent/TR200000713T2/xx unknown
- 1998-09-10 HU HU0002423A patent/HUP0002423A3/hu unknown
- 1998-09-10 DE DE69804981T patent/DE69804981T2/de not_active Expired - Lifetime
- 1998-09-10 CN CN98809037A patent/CN1270593A/zh active Pending
- 1998-09-10 AT AT98951380T patent/ATE216370T1/de not_active IP Right Cessation
- 1998-09-10 AU AU97429/98A patent/AU743717B2/en not_active Ceased
- 1998-09-10 EP EP98951380A patent/EP1015434B1/en not_active Expired - Lifetime
- 1998-09-10 JP JP2000511753A patent/JP2001516749A/ja active Pending
- 1998-09-11 ZA ZA988336A patent/ZA988336B/xx unknown
- 1998-09-12 EG EG110398A patent/EG22051A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1015434A2 (en) | 2000-07-05 |
| ES2175804T3 (es) | 2002-11-16 |
| KR100585571B1 (ko) | 2006-06-02 |
| KR20010023894A (ko) | 2001-03-26 |
| HUP0002423A3 (en) | 2001-02-28 |
| DE69804981T2 (de) | 2002-11-28 |
| CA2301694A1 (en) | 1999-03-25 |
| EG22051A (en) | 2002-06-30 |
| DK1015434T3 (da) | 2002-08-05 |
| CN1270593A (zh) | 2000-10-18 |
| HUP0002423A2 (hu) | 2000-11-28 |
| WO1999014202A2 (en) | 1999-03-25 |
| PL339053A1 (en) | 2000-12-04 |
| PT1015434E (pt) | 2002-08-30 |
| ZA988336B (en) | 1999-02-12 |
| BR9812439A (pt) | 2000-09-26 |
| AU9742998A (en) | 1999-04-05 |
| ATE216370T1 (de) | 2002-05-15 |
| HN1998000139A (es) | 1999-06-02 |
| US6277858B1 (en) | 2001-08-21 |
| WO1999014202B1 (en) | 1999-06-17 |
| AU743717B2 (en) | 2002-01-31 |
| TW429254B (en) | 2001-04-11 |
| WO1999014202A3 (en) | 1999-05-14 |
| AR015439A1 (es) | 2001-05-02 |
| GT199800142A (es) | 2000-03-02 |
| GB9719411D0 (en) | 1997-11-12 |
| IL134779A0 (en) | 2001-04-30 |
| DE69804981D1 (de) | 2002-05-23 |
| JP2001516749A (ja) | 2001-10-02 |
| EP1015434B1 (en) | 2002-04-17 |
| TR200000713T2 (tr) | 2000-08-21 |
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Legal Events
| Date | Code | Title | Description |
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| PSEA | Patent sealed |