SK50293A3 - 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl) urea fungicidal agents - Google Patents
1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl) urea fungicidal agents Download PDFInfo
- Publication number
- SK50293A3 SK50293A3 SK502-93A SK50293A SK50293A3 SK 50293 A3 SK50293 A3 SK 50293A3 SK 50293 A SK50293 A SK 50293A SK 50293 A3 SK50293 A3 SK 50293A3
- Authority
- SK
- Slovakia
- Prior art keywords
- optionally substituted
- group
- halogen
- alkyl
- oxo
- Prior art date
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 96
- 239000004202 carbamide Substances 0.000 title claims description 51
- 239000000417 fungicide Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 20
- 241000233866 Fungi Species 0.000 claims abstract description 17
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 11
- -1 cyano, hydroxy Chemical group 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 61
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 241000196324 Embryophyta Species 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 235000018290 Musa x paradisiaca Nutrition 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 235000021536 Sugar beet Nutrition 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 244000105624 Arachis hypogaea Species 0.000 claims description 8
- 206010061217 Infestation Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 241000530549 Cercospora beticola Species 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 241001329956 Nothopassalora personata Species 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 230000002538 fungal effect Effects 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 235000020232 peanut Nutrition 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- GRMJTTXFYBMPDV-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(2-ethylsulfanyl-4-oxoquinazolin-3-yl)urea Chemical compound CCSC1=NC2=CC=CC=C2C(=O)N1NC(=O)NC1=CC=C(Cl)C=C1 GRMJTTXFYBMPDV-UHFFFAOYSA-N 0.000 claims description 2
- UHROEPCZTAXVGK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(4-oxoquinazolin-3-yl)thiourea Chemical compound C1=CC(Cl)=CC=C1NC(=S)NN1C(=O)C2=CC=CC=C2N=C1 UHROEPCZTAXVGK-UHFFFAOYSA-N 0.000 claims description 2
- 241001065113 Cercosporidium Species 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- OFUZTHKMRFLVTN-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(4-oxoquinazolin-3-yl)urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NN1C(=O)C2=CC=CC=C2N=C1 OFUZTHKMRFLVTN-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 101100366940 Mus musculus Stom gene Proteins 0.000 claims 1
- 240000008790 Musa x paradisiaca Species 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052758 niobium Inorganic materials 0.000 claims 1
- 239000010955 niobium Substances 0.000 claims 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 6
- 230000002265 prevention Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- 238000012360 testing method Methods 0.000 description 21
- 238000011156 evaluation Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 241000234295 Musa Species 0.000 description 16
- 125000001309 chloro group Chemical group Cl* 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000001629 suppression Effects 0.000 description 12
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 235000016068 Berberis vulgaris Nutrition 0.000 description 6
- 241000335053 Beta vulgaris Species 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XZRJWCFKYOZVIH-UHFFFAOYSA-N 3-aminoquinazolin-4-one Chemical compound C1=CC=C2C(=O)N(N)C=NC2=C1 XZRJWCFKYOZVIH-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000010183 spectrum analysis Methods 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
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- 238000011081 inoculation Methods 0.000 description 3
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- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- 239000000725 suspension Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 2
- LPFTXHUMWOPBNF-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(8-methoxy-4-oxoquinazolin-3-yl)urea Chemical compound COC1=CC=CC(C2=O)=C1N=CN2NC(=O)NC1=CC=C(Br)C=C1 LPFTXHUMWOPBNF-UHFFFAOYSA-N 0.000 description 2
- YONGFZJAMHVZAH-UHFFFAOYSA-N 1-(4-iodophenyl)-3-(4-oxoquinazolin-3-yl)urea Chemical compound Ic1ccc(NC(=O)Nn2cnc3ccccc3c2=O)cc1 YONGFZJAMHVZAH-UHFFFAOYSA-N 0.000 description 2
- OXFKGEPYTJGZOZ-UHFFFAOYSA-N 1-amino-3-(4-chlorophenyl)urea Chemical compound NNC(=O)NC1=CC=C(Cl)C=C1 OXFKGEPYTJGZOZ-UHFFFAOYSA-N 0.000 description 2
- XQACWEBGSZBLRG-UHFFFAOYSA-N 1-bromo-4-isothiocyanatobenzene Chemical compound BrC1=CC=C(N=C=S)C=C1 XQACWEBGSZBLRG-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
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- XEKZKLKRHMPCPM-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methyl-1-(4-oxoquinazolin-3-yl)urea Chemical compound C1=NC2=CC=CC=C2C(=O)N1N(C)C(=O)NC1=CC=C(Cl)C=C1 XEKZKLKRHMPCPM-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- 239000004546 suspension concentrate Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class 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 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-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
- 239000002562 thickening agent Substances 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-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
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000001018 virulence Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—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
- C07D239/93—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- 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
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/891,528 US5276038A (en) | 1992-06-01 | 1992-06-01 | 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK50293A3 true SK50293A3 (en) | 1994-04-06 |
Family
ID=25398351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK502-93A SK50293A3 (en) | 1992-06-01 | 1993-05-19 | 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl) urea fungicidal agents |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US5276038A (cs) |
| EP (1) | EP0572782B1 (cs) |
| JP (1) | JPH0656798A (cs) |
| AT (1) | ATE139770T1 (cs) |
| AU (1) | AU3991893A (cs) |
| CA (1) | CA2097276A1 (cs) |
| CZ (1) | CZ90493A3 (cs) |
| DE (1) | DE69303329T2 (cs) |
| DK (1) | DK0572782T3 (cs) |
| ES (1) | ES2088607T3 (cs) |
| GR (1) | GR3020383T3 (cs) |
| HU (1) | HUT65219A (cs) |
| MX (1) | MX9303084A (cs) |
| SK (1) | SK50293A3 (cs) |
| ZA (1) | ZA933793B (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276038A (en) * | 1992-06-01 | 1994-01-04 | American Cyanamid Company | 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents |
| WO1994026722A1 (en) * | 1993-05-12 | 1994-11-24 | E.I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| EP0735035B1 (en) * | 1995-03-31 | 2002-06-05 | Nihon Nohyaku Co., Ltd. | Substituted aminoquinazolinone (thione) derivatives or salts thereof, intermediates thereof, and pest controllers and a method for using the same |
| US6897213B1 (en) * | 1995-11-21 | 2005-05-24 | Warner-Lambert Company | Heterocycles as cholecystokinin (CCK) ligands |
| BR9714222A (pt) * | 1996-12-17 | 2000-04-18 | Du Pont | Método para o controle de doenças de plantas |
| US6054224A (en) * | 1997-08-25 | 2000-04-25 | Toray Industries, Inc. | Polyester film for electrical insulation |
| US6184377B1 (en) * | 1997-12-15 | 2001-02-06 | Sepracor Inc. | Compositions containing N-amino- and N-hydroxy-quinazolinones and methods for preparing libraries thereof |
| US6255311B1 (en) * | 1998-01-14 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Fungicidal fused bicyclic pyrimidinones |
| ATE488231T1 (de) * | 2002-12-23 | 2010-12-15 | Icagen Inc | Quinazolinone als kaliumkanalmodulatoren |
| AU2004272104B2 (en) * | 2003-09-10 | 2011-09-08 | Icagen, Inc | Fused ring heterocycles as potassium channel modulators |
| AU2003273634A1 (en) * | 2003-10-02 | 2005-04-14 | Chimac-Agriphar S.A. | Composition and method for treating banana trees |
| US9750248B2 (en) * | 2012-12-31 | 2017-09-05 | Dow Agrosciences Llc | Synergistic fungicidal compositions |
| US9247742B2 (en) * | 2012-12-31 | 2016-02-02 | Dow Agrosciences Llc | Synergistic fungicidal compositions |
| US10455835B2 (en) * | 2012-12-31 | 2019-10-29 | Dow Agrosciences Llc | Fungicidal compositions for controlling leaf spots in sugar beets |
| CN104402885A (zh) * | 2014-11-19 | 2015-03-11 | 陕西嘉禾植物化工有限责任公司 | 一种吴茱萸次碱的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3696102A (en) * | 1970-03-09 | 1972-10-03 | Pfizer & Co C | Process for the synthesis of substituted quinazolin-4-ones |
| DD206996A1 (de) * | 1982-01-27 | 1984-02-15 | Akad Wissenschaften Ddr | Verfahren zur herstellung von substituierten 9h-9-oxo-s-triazolo(5,1-b)chinazolinen |
| DE3228871A1 (de) * | 1982-08-03 | 1984-02-09 | Bayer Ag, 5090 Leverkusen | Oxochinazolin-carbaminsaeureester |
| GB8429739D0 (en) * | 1984-11-24 | 1985-01-03 | Fbc Ltd | Fungicides |
| US4605657A (en) * | 1985-04-30 | 1986-08-12 | Chevron Research Company | 4-quinazalone fungicides |
| GB8820129D0 (en) * | 1988-08-24 | 1988-09-28 | Schering Agrochemicals Ltd | Fungicides |
| US5276038A (en) * | 1992-06-01 | 1994-01-04 | American Cyanamid Company | 1-aryl-3-(3,4-dihydro-4-oxo-3-quinazolinyl)urea fungicidal agents |
-
1992
- 1992-06-01 US US07/891,528 patent/US5276038A/en not_active Expired - Fee Related
-
1993
- 1993-04-02 US US08/035,871 patent/US5354755A/en not_active Expired - Lifetime
- 1993-04-15 DK DK93106107.1T patent/DK0572782T3/da active
- 1993-04-15 ES ES93106107T patent/ES2088607T3/es not_active Expired - Lifetime
- 1993-04-15 AT AT93106107T patent/ATE139770T1/de not_active IP Right Cessation
- 1993-04-15 DE DE69303329T patent/DE69303329T2/de not_active Expired - Fee Related
- 1993-04-15 EP EP93106107A patent/EP0572782B1/en not_active Expired - Lifetime
- 1993-05-14 CZ CZ93904A patent/CZ90493A3/cs unknown
- 1993-05-19 SK SK502-93A patent/SK50293A3/sk unknown
- 1993-05-26 MX MX9303084A patent/MX9303084A/es unknown
- 1993-05-26 JP JP5147029A patent/JPH0656798A/ja active Pending
- 1993-05-28 CA CA002097276A patent/CA2097276A1/en not_active Abandoned
- 1993-05-28 ZA ZA933793A patent/ZA933793B/xx unknown
- 1993-05-28 HU HU9301578A patent/HUT65219A/hu unknown
- 1993-05-31 AU AU39918/93A patent/AU3991893A/en not_active Abandoned
-
1996
- 1996-06-28 GR GR960400247T patent/GR3020383T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3991893A (en) | 1993-12-02 |
| GR3020383T3 (en) | 1996-09-30 |
| DK0572782T3 (da) | 1996-07-29 |
| CA2097276A1 (en) | 1993-12-02 |
| JPH0656798A (ja) | 1994-03-01 |
| MX9303084A (es) | 1994-06-30 |
| EP0572782B1 (en) | 1996-06-26 |
| US5276038A (en) | 1994-01-04 |
| HU9301578D0 (en) | 1993-09-28 |
| ES2088607T3 (es) | 1996-08-16 |
| HUT65219A (en) | 1994-05-02 |
| CZ90493A3 (en) | 1994-02-16 |
| DE69303329D1 (de) | 1996-08-01 |
| ATE139770T1 (de) | 1996-07-15 |
| ZA933793B (en) | 1993-12-22 |
| EP0572782A1 (en) | 1993-12-08 |
| US5354755A (en) | 1994-10-11 |
| DE69303329T2 (de) | 1997-01-23 |
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