JPH0741471A - 殺真菌活性を有する３，４−ジアリール−（５ｈ）−フラン−２−オンを基本構造とする化合物 - Google Patents
殺真菌活性を有する３，４−ジアリール−（５ｈ）−フラン−２−オンを基本構造とする化合物Info
- Publication number
- JPH0741471A JPH0741471A JP5091981A JP9198193A JPH0741471A JP H0741471 A JPH0741471 A JP H0741471A JP 5091981 A JP5091981 A JP 5091981A JP 9198193 A JP9198193 A JP 9198193A JP H0741471 A JPH0741471 A JP H0741471A
- Authority
- JP
- Japan
- Prior art keywords
- furan
- compound
- same
- general formula
- branched
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 12
- 125000000524 functional group Chemical group 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 229940121375 antifungal agent Drugs 0.000 claims abstract 7
- 239000003429 antifungal agent Substances 0.000 claims abstract 7
- -1 2-benzyloxyphenyl Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000007363 ring formation reaction Methods 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005283 haloketone group Chemical group 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- IIFGCOVQCGZQNZ-UHFFFAOYSA-N 4-[2-[(4-bromophenyl)methoxy]phenyl]-3-(4-chlorophenyl)-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)OCC=2C=CC(Br)=CC=2)C(=O)OC1 IIFGCOVQCGZQNZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 2
- 239000012973 diazabicyclooctane Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 238000009331 sowing Methods 0.000 claims description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- NFGONRKNOJZPBI-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-[2-[(2,4-dichlorophenyl)methoxy]phenyl]-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)OCC=2C(=CC(Cl)=CC=2)Cl)C(=O)OC1 NFGONRKNOJZPBI-UHFFFAOYSA-N 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000012871 anti-fungal composition Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008029 eradication Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000013339 cereals Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VFYKRBZHJFJOGQ-UHFFFAOYSA-N 2-(2-phenylmethoxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1OCC1=CC=CC=C1 VFYKRBZHJFJOGQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NNOIMVUVKZIBOP-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-4-[2-[(4-methoxyphenyl)methoxy]phenyl]-2h-furan-5-one Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC=C1C1=C(C=2C(=CC(Cl)=CC=2)Cl)COC1=O NNOIMVUVKZIBOP-UHFFFAOYSA-N 0.000 description 1
- IWIZBZVAGZNQIH-UHFFFAOYSA-N 3-(3-chlorophenyl)-4-[2-[(4-chlorophenyl)methoxy]phenyl]-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1COC1=CC=CC=C1C1=C(C=2C=C(Cl)C=CC=2)COC1=O IWIZBZVAGZNQIH-UHFFFAOYSA-N 0.000 description 1
- BHKBGFFREIIOBP-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-(2-phenylmethoxyphenyl)-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1C1=C(C=2C(=CC=CC=2)OCC=2C=CC=CC=2)C(=O)OC1 BHKBGFFREIIOBP-UHFFFAOYSA-N 0.000 description 1
- HHLZLFPLDNLCOQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-[2-[(4-chlorophenyl)methoxy]phenyl]-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1COC1=CC=CC=C1C1=C(C=2C=CC(Cl)=CC=2)COC1=O HHLZLFPLDNLCOQ-UHFFFAOYSA-N 0.000 description 1
- ZUFFTQJSOSAIMN-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-[2-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]-2h-furan-5-one Chemical compound C1=CC(C(F)(F)F)=CC=C1COC1=CC=CC=C1C1=C(C=2C=CC(Cl)=CC=2)COC1=O ZUFFTQJSOSAIMN-UHFFFAOYSA-N 0.000 description 1
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 1
- YFKAWHFJILMBPK-UHFFFAOYSA-N 4-[2-[(4-chlorophenyl)methoxy]phenyl]-3-phenyl-2h-furan-5-one Chemical compound C1=CC(Cl)=CC=C1COC1=CC=CC=C1C1=C(C=2C=CC=CC=2)COC1=O YFKAWHFJILMBPK-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000380131 Ammophila arenaria Species 0.000 description 1
- 241000796533 Arna Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000371644 Curvularia ravenelii Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Polymers OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 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 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000004117 Lignosulphonate Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001602730 Monza Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001223281 Peronospora Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000317981 Podosphaera fuliginea Species 0.000 description 1
- 241000520648 Pyrenophora teres Species 0.000 description 1
- 241001515786 Rhynchosporium Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- FBPFZTCFMRRESA-NQAPHZHOSA-N Sorbitol Polymers OCC(O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-NQAPHZHOSA-N 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
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)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI920713A IT1254558B (it) | 1992-03-26 | 1992-03-26 | Composti a base di 3,4-diaril-(5h)-furan-2-one ad attivita' fungicida 3 |
| IT92-A/000713 | 1992-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0741471A true JPH0741471A (ja) | 1995-02-10 |
Family
ID=11362616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5091981A Pending JPH0741471A (ja) | 1992-03-26 | 1993-03-26 | 殺真菌活性を有する３，４−ジアリール−（５ｈ）−フラン−２−オンを基本構造とする化合物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5371106A (en, 2012) |
| EP (1) | EP0566175B1 (en, 2012) |
| JP (1) | JPH0741471A (en, 2012) |
| AT (1) | ATE156486T1 (en, 2012) |
| AU (1) | AU657397B2 (en, 2012) |
| CA (1) | CA2092484A1 (en, 2012) |
| DE (1) | DE69312776T2 (en, 2012) |
| DK (1) | DK0566175T3 (en, 2012) |
| ES (1) | ES2105074T3 (en, 2012) |
| GR (1) | GR3024645T3 (en, 2012) |
| IT (1) | IT1254558B (en, 2012) |
| TW (1) | TW231256B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6492413B2 (en) | 1993-01-15 | 2002-12-10 | G.D. Searle & Co. | 3.4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| EP0730581B1 (en) * | 1993-11-22 | 2001-10-04 | Merck & Co. Inc. | 3-acylaminobenzazepines |
| SK282019B6 (sk) * | 1994-08-18 | 2001-10-08 | Merck & Co., Inc. | 2,3-dihydro-1-(2,2,2-trifluóretyl)-2-oxo-5-fenyl-1h-1,4- benzodiazepínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
| US5691331A (en) * | 1995-06-07 | 1997-11-25 | Merck & Co., Inc. | N-(2,4-Dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3yl) -3- amides |
| US5700797A (en) * | 1995-06-07 | 1997-12-23 | Merck & Co, Inc. | N-(2,4-dioxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl)-3-amides |
| US5726171A (en) * | 1995-06-07 | 1998-03-10 | Merck & Co Inc | N-(1-alkyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo B! 1,4!diazepin-3yl)-acetamides |
| EP0833819B1 (en) * | 1995-06-07 | 2003-03-26 | Merck & Co., Inc. | Novel n-(2-oxo-2,3,4,5-tetrahydro-1h-1,5-benzodiazepin-3yl)-3-amides |
| US5631251A (en) * | 1995-06-07 | 1997-05-20 | Merck & Co., Inc. | 5-cyclopropyl-1,4 benzodiazepine-2-ones |
| GB9615867D0 (en) * | 1996-07-03 | 1996-09-11 | Merck & Co Inc | Process of preparing phenyl heterocycles useful as cox-2 inhibitors |
| US20020173042A1 (en) * | 2001-03-16 | 2002-11-21 | Timothy Oolman | Method of tagging agricultural products |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195026A (en) * | 1978-12-04 | 1980-03-25 | Iowa State University Research Foundation, Inc. | Substituted furans from butenolides |
| US4214092A (en) * | 1979-02-21 | 1980-07-22 | Iowa State University Research Foundation, Inc. | Rearrangement of acyloxy furans and thiophenes prepared from butenolides |
| US4968817A (en) * | 1984-07-27 | 1990-11-06 | National Distillers And Chemical Corporation | Manufacture of gamma-crotonolactone by carbonylation of glycidol |
| DE3718527A1 (de) * | 1987-06-03 | 1988-12-15 | Basf Ag | Verfahren zur herstellung von 2(5h)-furanonen |
-
1992
- 1992-03-26 IT ITMI920713A patent/IT1254558B/it active
-
1993
- 1993-03-20 DK DK93200822.0T patent/DK0566175T3/da active
- 1993-03-20 AT AT93200822T patent/ATE156486T1/de active
- 1993-03-20 DE DE69312776T patent/DE69312776T2/de not_active Expired - Fee Related
- 1993-03-20 EP EP93200822A patent/EP0566175B1/en not_active Expired - Lifetime
- 1993-03-20 ES ES93200822T patent/ES2105074T3/es not_active Expired - Lifetime
- 1993-03-23 AU AU35384/93A patent/AU657397B2/en not_active Ceased
- 1993-03-24 US US08/036,500 patent/US5371106A/en not_active Expired - Fee Related
- 1993-03-25 CA CA002092484A patent/CA2092484A1/en not_active Abandoned
- 1993-03-26 JP JP5091981A patent/JPH0741471A/ja active Pending
- 1993-03-26 TW TW082102289A patent/TW231256B/zh active
-
1997
- 1997-09-04 GR GR970402283T patent/GR3024645T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69312776D1 (de) | 1997-09-11 |
| AU3538493A (en) | 1993-09-30 |
| TW231256B (en, 2012) | 1994-10-01 |
| EP0566175A2 (en) | 1993-10-20 |
| CA2092484A1 (en) | 1993-09-27 |
| AU657397B2 (en) | 1995-03-09 |
| GR3024645T3 (en) | 1997-12-31 |
| ITMI920713A0 (it) | 1992-03-26 |
| ATE156486T1 (de) | 1997-08-15 |
| EP0566175A3 (en, 2012) | 1994-01-19 |
| US5371106A (en) | 1994-12-06 |
| ITMI920713A1 (it) | 1993-09-26 |
| DK0566175T3 (da) | 1998-01-26 |
| IT1254558B (it) | 1995-09-25 |
| DE69312776T2 (de) | 1998-01-15 |
| EP0566175B1 (en) | 1997-08-06 |
| ES2105074T3 (es) | 1997-10-16 |
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