BG64048B1 - Фунгицидни 2-метоксибензофенони - Google Patents
Фунгицидни 2-метоксибензофенони Download PDFInfo
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- BG64048B1 BG64048B1 BG102704A BG10270498A BG64048B1 BG 64048 B1 BG64048 B1 BG 64048B1 BG 102704 A BG102704 A BG 102704A BG 10270498 A BG10270498 A BG 10270498A BG 64048 B1 BG64048 B1 BG 64048B1
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- Prior art keywords
- methyl
- formula
- compound
- chloro
- group
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- 239000000417 fungicide Substances 0.000 title abstract description 8
- 230000000855 fungicidal effect Effects 0.000 title description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 239000000203 mixture Substances 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- -1 6,6'-dimethyl-2,2 ', 3', 4'-tetramethoxybenzophenone 6,6'-dimethyl-3'-pentoxy-2,2 ', 4'-trimethoxybenzophenone Chemical compound 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 31
- 241000233866 Fungi Species 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- CSUUDNFYSFENAE-UHFFFAOYSA-N (2-methoxyphenyl)-phenylmethanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=CC=C1 CSUUDNFYSFENAE-UHFFFAOYSA-N 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 9
- 241000221785 Erysiphales Species 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- LHCMTRPUBRYBKS-UHFFFAOYSA-N (3-bromo-2-chloro-6-methoxyphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C(Br)C(Cl)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC LHCMTRPUBRYBKS-UHFFFAOYSA-N 0.000 claims description 4
- 241000235349 Ascomycota Species 0.000 claims description 4
- 241001480061 Blumeria graminis Species 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- XVUCLVGKPVBIJZ-UHFFFAOYSA-N (2-methoxynaphthalen-1-yl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC XVUCLVGKPVBIJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 241000510928 Erysiphe necator Species 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 241001337928 Podosphaera leucotricha Species 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- IDHMZXJBTBENOT-UHFFFAOYSA-N (2-chloro-6-methoxy-3-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C(C)C(Cl)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC IDHMZXJBTBENOT-UHFFFAOYSA-N 0.000 claims description 2
- XMVCFKGSZHPQNL-UHFFFAOYSA-N (2-chloro-6-methoxyphenyl)-[3,4-dimethoxy-6-methyl-2-[(4-methylphenyl)methoxy]phenyl]methanone Chemical compound COC1=CC=CC(Cl)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OCC1=CC=C(C)C=C1 XMVCFKGSZHPQNL-UHFFFAOYSA-N 0.000 claims description 2
- OVENYBUIFHYMBX-UHFFFAOYSA-N (3-iodo-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C(I)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC OVENYBUIFHYMBX-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- LDJSNTDCCHVCOJ-UHFFFAOYSA-N [2-chloro-6-(difluoromethoxy)phenyl]-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1OC(F)F LDJSNTDCCHVCOJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical class CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 claims 2
- WGBRJORYTUSWRY-UHFFFAOYSA-N (2-chloro-6-methoxyphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=CC(Cl)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC WGBRJORYTUSWRY-UHFFFAOYSA-N 0.000 claims 1
- SOWCHIKULXGZSE-UHFFFAOYSA-N (2-chloro-6-methoxyphenyl)-(3,4-dimethoxy-6-methyl-2-pentoxyphenyl)methanone Chemical compound CCCCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1OC SOWCHIKULXGZSE-UHFFFAOYSA-N 0.000 claims 1
- MVLDNAYSRXREBQ-UHFFFAOYSA-N (2-chloro-6-methoxyphenyl)-[2-[(2-fluorophenyl)methoxy]-3,4-dimethoxy-6-methylphenyl]methanone Chemical compound COC1=CC=CC(Cl)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OCC1=CC=CC=C1F MVLDNAYSRXREBQ-UHFFFAOYSA-N 0.000 claims 1
- BYEMEJLACWCACK-UHFFFAOYSA-N (3-bromo-6-methoxy-2-methylphenyl)-(2,4-dimethoxy-6-methyl-3-pentoxyphenyl)methanone Chemical compound CCCCCOC1=C(OC)C=C(C)C(C(=O)C=2C(=CC=C(Br)C=2C)OC)=C1OC BYEMEJLACWCACK-UHFFFAOYSA-N 0.000 claims 1
- PIOFIEKNWAEXLH-UHFFFAOYSA-N (3-chloro-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C(Cl)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC PIOFIEKNWAEXLH-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 241000196324 Embryophyta Species 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 201000010099 disease Diseases 0.000 description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004094 surface-active agent Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 244000098338 Triticum aestivum Species 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 235000021307 Triticum Nutrition 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 235000014121 butter Nutrition 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 238000011081 inoculation Methods 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 9
- 239000003208 petroleum Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 240000008067 Cucumis sativus Species 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 229920001213 Polysorbate 20 Polymers 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 6
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 238000003828 vacuum filtration Methods 0.000 description 6
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 230000001717 pathogenic effect Effects 0.000 description 5
- 230000003032 phytopathogenic effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 235000009849 Cucumis sativus Nutrition 0.000 description 4
- 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 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 150000008366 benzophenones Chemical class 0.000 description 4
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HBPDHOUFKMTSHG-UHFFFAOYSA-N (2,6-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C)=C1C(=O)C1=CC=CC=C1 HBPDHOUFKMTSHG-UHFFFAOYSA-N 0.000 description 3
- QSUUGSPQSTYRDK-UHFFFAOYSA-N (2-methoxy-6-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=CC(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC QSUUGSPQSTYRDK-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
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- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- GQLSLEBNODXANJ-UHFFFAOYSA-N ethyl 2-methoxy-6-methylbenzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1OC GQLSLEBNODXANJ-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- TWUNPMYMEKMFSD-UHFFFAOYSA-N (3-fluoro-6-methoxy-2-methylphenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=CC=C(F)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC TWUNPMYMEKMFSD-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
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- PZXLGCIJEFUSLH-UHFFFAOYSA-N 3-bromo-6-methoxy-2-methylbenzoic acid Chemical compound COC1=CC=C(Br)C(C)=C1C(O)=O PZXLGCIJEFUSLH-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
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- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
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- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-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
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- 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
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-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
- IECKAVQTURBPON-UHFFFAOYSA-N trimethoxymethylbenzene Chemical compound COC(OC)(OC)C1=CC=CC=C1 IECKAVQTURBPON-UHFFFAOYSA-N 0.000 description 1
- TZPKFPYZCMHDHL-UHFFFAOYSA-N trimethoxytoluene Natural products COC1=CC(OC)=C(C)C(OC)=C1 TZPKFPYZCMHDHL-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-N 0.000 description 1
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- 238000009369 viticulture Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/914,966 US5945567A (en) | 1997-08-20 | 1997-08-20 | Fungicidal 2-methoxybenzophenones |
Publications (2)
Publication Number | Publication Date |
---|---|
BG102704A BG102704A (en) | 1999-10-29 |
BG64048B1 true BG64048B1 (bg) | 2003-11-28 |
Family
ID=25435014
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG102704A BG64048B1 (bg) | 1997-08-20 | 1998-08-20 | Фунгицидни 2-метоксибензофенони |
Country Status (25)
Country | Link |
---|---|
US (2) | US5945567A (cs) |
JP (1) | JP4416851B2 (cs) |
KR (2) | KR100659806B1 (cs) |
CN (2) | CN1300084C (cs) |
AR (1) | AR016392A1 (cs) |
BG (1) | BG64048B1 (cs) |
BR (1) | BR9803198B1 (cs) |
CA (1) | CA2245124C (cs) |
CO (1) | CO5050332A1 (cs) |
CZ (1) | CZ294488B6 (cs) |
EA (1) | EA002606B1 (cs) |
EE (1) | EE03962B1 (cs) |
GE (1) | GEP20032878B (cs) |
HR (1) | HRP980439B1 (cs) |
HU (1) | HU225229B1 (cs) |
ID (1) | ID20744A (cs) |
IL (2) | IL125788A (cs) |
MY (1) | MY126559A (cs) |
PL (1) | PL193675B1 (cs) |
RO (1) | RO120905B1 (cs) |
SK (1) | SK283231B6 (cs) |
TR (1) | TR199801629A2 (cs) |
TW (1) | TW382013B (cs) |
UA (1) | UA46826C2 (cs) |
ZA (1) | ZA987489B (cs) |
Families Citing this family (55)
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US6242498B1 (en) * | 1997-08-20 | 2001-06-05 | Juergen Curtze | Fungicidal 2,6,6′-trimethylbenzophenones |
US6277856B1 (en) * | 1998-09-25 | 2001-08-21 | American Cynamid Co. | Fungicidal mixtures |
US6383984B1 (en) | 1999-01-29 | 2002-05-07 | Basf Aktiengesellschaft | Aqueous suspension concentrate |
US6346535B1 (en) | 1999-01-29 | 2002-02-12 | American Cyanamid Company | Fungicidal mixtures |
US6521628B1 (en) | 1999-01-29 | 2003-02-18 | Basf Aktiengesellschaft | Fungicidal mixtures |
US6444618B1 (en) | 1999-01-29 | 2002-09-03 | Basf Aktiengesellschaft | Crop protection emulsifiable concentrate containing defoaming agents |
US6613806B1 (en) | 1999-01-29 | 2003-09-02 | Basf Corporation | Enhancement of the efficacy of benzoylbenzenes |
GB9912220D0 (en) | 1999-05-26 | 1999-07-28 | Novartis Ag | Organic compounds |
GB9912219D0 (en) | 1999-05-26 | 1999-07-28 | Novartis Ag | Organic compounds |
PT1185173E (pt) * | 1999-06-14 | 2003-10-31 | Syngenta Participations Ag | Combinacoes fungicidas |
US6559336B2 (en) | 1999-07-15 | 2003-05-06 | Basf Aktiengesellschaft | Process for the preparation of 5- and/or 6-substituted-2-hydroxybenzoic acid esters |
BR0012493B1 (pt) | 1999-07-15 | 2011-02-22 | processo para a preparação de um composto de éster de ácido 2-hidróxi-benzóico substituìdo, e, processo para a manufatura de composto fungicida de benzofenona. | |
US6699874B2 (en) | 1999-09-24 | 2004-03-02 | Basf Aktiengesellschaft | Fungicidal mixtures |
GB0010198D0 (en) * | 2000-04-26 | 2000-06-14 | Novartis Ag | Organic compounds |
GB0028702D0 (en) * | 2000-11-24 | 2001-01-10 | Novartis Ag | Organic compounds |
JP4188688B2 (ja) * | 2001-01-18 | 2008-11-26 | ビーエーエスエフ ソシエタス・ヨーロピア | ベンゾフェノン類およびイミダゾール誘導体を含む殺菌性混合物 |
US6919485B2 (en) * | 2001-03-13 | 2005-07-19 | Basf Aktiengesellschaft | Benzophenones, the production thereof and their use for controlling plant pathogenic fungi |
EP2289326A1 (de) * | 2002-03-21 | 2011-03-02 | Basf Se | Fungizide Mischungen |
UA80142C2 (en) * | 2002-07-11 | 2007-08-27 | Basf Ag | Use of a benzophenone derivative to control pseudocercosporella herpotrichoides |
WO2004045288A2 (de) * | 2002-11-15 | 2004-06-03 | Basf Aktiengesellschaft | Fungizide mischungen zur bekämpfung von reispathogenen |
UA79182C2 (en) * | 2002-12-13 | 2007-05-25 | Basf Ag | Method for the production of benzophenones |
DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
EP1744629B1 (de) | 2004-04-30 | 2012-12-05 | Basf Se | Fungizide mischungen |
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 |
HRP20141028T1 (hr) | 2005-08-05 | 2014-12-19 | Basf Se | Fungicidne smjese koje sadrže supstituirane anilide 1-metil-pirazol-4-ilkarboksilne kiseline |
DE102006023263A1 (de) | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
WO2008034787A2 (en) | 2006-09-18 | 2008-03-27 | Basf Se | Pesticidal mixtures comprising an anthranilamide insecticide and a fungicide |
WO2008071714A1 (en) | 2006-12-15 | 2008-06-19 | Rohm And Haas Company | Mixtures comprising 1-methylcyclopropene |
TW200845897A (en) | 2007-02-06 | 2008-12-01 | Basf Se | Pesticidal mixtures |
EP2076602A2 (en) | 2007-04-23 | 2009-07-08 | Basf Se | Plant produtivity enhancement by combining chemical agents with transgenic modifications |
BRPI0816948B1 (pt) | 2007-09-20 | 2018-01-23 | Basf Se | Composição fungicida, seus usos, agente fungicida, método para controlar fungos nocivos fitopatogênicos, e semente resistente a fungos nocivos fitopatogênicos |
CN101808521A (zh) | 2007-09-26 | 2010-08-18 | 巴斯夫欧洲公司 | 包含啶酰菌胺和百菌清的三元杀真菌组合物 |
KR101715047B1 (ko) * | 2009-07-07 | 2017-03-10 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | (2,4-디메틸비페닐-3-일)아세트산, 그의 에스테르 및 중간체의 제조방법 |
WO2011026796A1 (en) | 2009-09-01 | 2011-03-10 | Basf Se | Synergistic fungicidal mixtures comprising lactylates and method for combating phytopathogenic fungi |
CN103269589A (zh) | 2010-12-20 | 2013-08-28 | 巴斯夫欧洲公司 | 包含吡唑化合物的农药活性混合物 |
EP2481284A3 (en) | 2011-01-27 | 2012-10-17 | Basf Se | Pesticidal mixtures |
WO2012127009A1 (en) | 2011-03-23 | 2012-09-27 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
WO2013030338A2 (en) | 2011-09-02 | 2013-03-07 | Basf Se | Agricultural mixtures comprising arylquinazolinone compounds |
BR122019015109B1 (pt) | 2012-06-20 | 2020-04-07 | Basf Se | mistura pesticida, composição, composição agrícola, métodos para o combate ou controle das pragas de invertebrados, para a proteção dos vegetais em crescimento ou dos materias de propagação vegetal, para a proteção de material de propagação vegetal e uso de uma mistura pesticida |
CN102823597A (zh) * | 2012-09-13 | 2012-12-19 | 陕西上格之路生物科学有限公司 | 一种含苯菌酮和苯氧喹啉的杀菌组合物 |
WO2014056780A1 (en) | 2012-10-12 | 2014-04-17 | Basf Se | A method for combating phytopathogenic harmful microbes on cultivated plants or plant propagation material |
JP6576829B2 (ja) | 2012-12-20 | 2019-09-18 | ビーエーエスエフ アグロ ベー.ブイ. | トリアゾール化合物を含む組成物 |
EP2783569A1 (en) | 2013-03-28 | 2014-10-01 | Basf Se | Compositions comprising a triazole compound |
EP2835052A1 (en) | 2013-08-07 | 2015-02-11 | Basf Se | Fungicidal mixtures comprising pyrimidine fungicides |
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WO2015036059A1 (en) | 2013-09-16 | 2015-03-19 | Basf Se | Fungicidal pyrimidine compounds |
CN106577651B (zh) * | 2014-03-15 | 2019-09-17 | 海南正业中农高科股份有限公司 | 含苯菌酮与苦参碱或氧化苦参碱的农药组合物 |
EP2979549A1 (en) | 2014-07-31 | 2016-02-03 | Basf Se | Method for improving the health of a plant |
CA2963446A1 (en) | 2014-10-24 | 2016-04-28 | Basf Se | Nonampholytic, quaternizable and water-soluble polymers for modifying the surface charge of solid particles |
CN107033006B (zh) * | 2016-02-04 | 2018-12-18 | 长沙理工大学 | 一种二芳基酮的制备方法 |
EP3443842A4 (en) * | 2016-04-15 | 2019-09-11 | Ishihara Sangyo Kaisha, Ltd. | METHOD FOR POTENTIATING THE PLANT-DISEASING EFFECT OF AN ARYLPHENYLKETONE FUNGICIDE AND METHOD FOR CONTROLLING PLANT DISEASES |
IL257535B (en) | 2018-02-14 | 2020-01-30 | N3 Coat Ltd | Benzophenone compounds as light catalysts for polyolefins |
GB2592668B (en) * | 2020-03-06 | 2024-08-14 | Rotam Agrochem Int Co Ltd | A novel form of metrafenone, a process for its preparation and use of the same |
CN113060808A (zh) * | 2021-03-19 | 2021-07-02 | 衡阳市建衡实业有限公司 | 一种含聚氯化铝的水处理剂及其制备方法 |
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US5248817A (en) * | 1991-07-15 | 1993-09-28 | Merck & Co., Inc. | Process for aromatic bromination |
CZ294096B6 (cs) * | 1995-01-20 | 2004-10-13 | Americanácyanamidácompany | Benzofenonové sloučeninyŹ způsob jejich výrobyŹ fungicidní prostředky s jejich obsahem a způsob ochrany rostlin |
-
1997
- 1997-08-20 US US08/914,966 patent/US5945567A/en not_active Expired - Lifetime
- 1997-10-17 US US08/953,048 patent/US5922905A/en not_active Expired - Lifetime
-
1998
- 1998-08-11 HR HR980439A patent/HRP980439B1/xx not_active IP Right Cessation
- 1998-08-13 IL IL12578898A patent/IL125788A/xx not_active IP Right Cessation
- 1998-08-13 IL IL169544A patent/IL169544A/en not_active IP Right Cessation
- 1998-08-13 ID IDP981132A patent/ID20744A/id unknown
- 1998-08-13 CZ CZ19982568A patent/CZ294488B6/cs not_active IP Right Cessation
- 1998-08-17 SK SK1131-98A patent/SK283231B6/sk not_active IP Right Cessation
- 1998-08-17 KR KR1019980033252A patent/KR100659806B1/ko not_active Expired - Lifetime
- 1998-08-17 UA UA98084467A patent/UA46826C2/uk unknown
- 1998-08-17 MY MYPI98003718A patent/MY126559A/en unknown
- 1998-08-18 JP JP24651198A patent/JP4416851B2/ja not_active Expired - Fee Related
- 1998-08-18 RO RO98-01306A patent/RO120905B1/ro unknown
- 1998-08-18 CA CA002245124A patent/CA2245124C/en not_active Expired - Lifetime
- 1998-08-19 ZA ZA9807489A patent/ZA987489B/xx unknown
- 1998-08-19 CO CO98047339A patent/CO5050332A1/es unknown
- 1998-08-19 GE GEAP19984455A patent/GEP20032878B/en unknown
- 1998-08-19 EA EA199800645A patent/EA002606B1/ru not_active IP Right Cessation
- 1998-08-19 PL PL328112A patent/PL193675B1/pl unknown
- 1998-08-19 AR ARP980104100A patent/AR016392A1/es active IP Right Grant
- 1998-08-19 HU HU9801900A patent/HU225229B1/hu active Protection Beyond IP Right Term
- 1998-08-19 EE EE9800301A patent/EE03962B1/xx not_active IP Right Cessation
- 1998-08-20 BG BG102704A patent/BG64048B1/bg unknown
- 1998-08-20 BR BRPI9803198-8A patent/BR9803198B1/pt not_active IP Right Cessation
- 1998-08-20 CN CNB021473153A patent/CN1300084C/zh not_active Expired - Lifetime
- 1998-08-20 CN CNB981186327A patent/CN1147456C/zh not_active Expired - Lifetime
- 1998-08-20 TR TR1998/01629A patent/TR199801629A2/xx unknown
- 1998-08-20 TW TW087113743A patent/TW382013B/zh not_active IP Right Cessation
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2006
- 2006-01-31 KR KR1020060009286A patent/KR100693645B1/ko not_active Expired - Fee Related
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