SK285301B6 - Fungicídny prostriedok, spôsob ochrany rastlín, benzofenónové zlúčeniny a spôsob ich výroby - Google Patents
Fungicídny prostriedok, spôsob ochrany rastlín, benzofenónové zlúčeniny a spôsob ich výroby Download PDFInfo
- Publication number
- SK285301B6 SK285301B6 SK74-96A SK7496A SK285301B6 SK 285301 B6 SK285301 B6 SK 285301B6 SK 7496 A SK7496 A SK 7496A SK 285301 B6 SK285301 B6 SK 285301B6
- Authority
- SK
- Slovakia
- Prior art keywords
- och
- dichloro
- formula
- methylbenzophenone
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 30
- 150000008366 benzophenones Chemical class 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000417 fungicide Substances 0.000 title abstract description 11
- -1 benzophenone compound Chemical class 0.000 claims abstract description 52
- 239000012965 benzophenone Substances 0.000 claims abstract description 20
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 9
- 241000233866 Fungi Species 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 92
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- MNRHYMVFOONMCR-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2,3,4-trimethoxy-6-methylphenyl)methanone Chemical compound COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl MNRHYMVFOONMCR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- CCKKNHKEAHLKMI-UHFFFAOYSA-N (2,3-dibutoxy-4-methoxy-6-methylphenyl)-(2,6-dichlorophenyl)methanone Chemical compound CCCCOC1=C(OC)C=C(C)C(C(=O)C=2C(=CC=CC=2Cl)Cl)=C1OCCCC CCKKNHKEAHLKMI-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- NVGSPWRPRAJKHQ-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2-ethoxy-3,4-dimethoxy-6-methylphenyl)methanone Chemical compound CCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl NVGSPWRPRAJKHQ-UHFFFAOYSA-N 0.000 claims description 2
- PKDPNRNYDZAJIJ-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2-heptoxy-3,4-dimethoxy-6-methylphenyl)methanone Chemical compound CCCCCCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl PKDPNRNYDZAJIJ-UHFFFAOYSA-N 0.000 claims description 2
- LNVKFQDJZBDEEI-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2-hexoxy-3,4-dimethoxy-6-methylphenyl)methanone Chemical compound CCCCCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl LNVKFQDJZBDEEI-UHFFFAOYSA-N 0.000 claims description 2
- FYUMNWHEVXFHEC-UHFFFAOYSA-N (2,6-dichlorophenyl)-(3,4-dimethoxy-6-methyl-2-pentoxyphenyl)methanone Chemical compound CCCCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl FYUMNWHEVXFHEC-UHFFFAOYSA-N 0.000 claims description 2
- YBYMWEKNVMDQPI-UHFFFAOYSA-N (2,6-dichlorophenyl)-[3,4-dimethoxy-2-(2-methoxyethoxy)-6-methylphenyl]methanone Chemical compound COCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl YBYMWEKNVMDQPI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- MPJQMCGPDULGMG-UHFFFAOYSA-N (2,6-dichlorophenyl)-(3,4-dimethoxy-6-methyl-2-prop-2-ynoxyphenyl)methanone Chemical compound C#CCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl MPJQMCGPDULGMG-UHFFFAOYSA-N 0.000 claims 1
- QWFCOLFZFGYBNM-UHFFFAOYSA-N (2,6-dichlorophenyl)-(3,4-dimethoxy-6-methyl-2-propoxyphenyl)methanone Chemical compound CCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl QWFCOLFZFGYBNM-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 230000000254 damaging effect Effects 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 159
- 150000001875 compounds Chemical class 0.000 description 110
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000003921 oil Substances 0.000 description 63
- 235000019198 oils Nutrition 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 20
- 239000004094 surface-active agent Substances 0.000 description 20
- 239000013078 crystal Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 238000003818 flash chromatography Methods 0.000 description 17
- 238000012360 testing method Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 241000221785 Erysiphales Species 0.000 description 8
- 241001337928 Podosphaera leucotricha Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 229910052727 yttrium Inorganic materials 0.000 description 7
- JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 6
- 240000005979 Hordeum vulgare Species 0.000 description 6
- 235000007340 Hordeum vulgare Nutrition 0.000 description 6
- 208000031888 Mycoses Diseases 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000001212 derivatisation Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IWBNMTGSLWEHRI-UHFFFAOYSA-N (2,6-dichlorophenyl)-(5-hydroxy-4-methoxy-2-methylphenyl)methanone Chemical compound C1=C(O)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl IWBNMTGSLWEHRI-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- 241000510928 Erysiphe necator Species 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229960001701 chloroform Drugs 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241001480061 Blumeria graminis Species 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 241000221787 Erysiphe Species 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000005661 deetherification reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 230000000885 phytotoxic effect Effects 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- KDIMAGCIYZVIFU-UHFFFAOYSA-N (2,6-dichlorophenyl)-(4,5-dimethoxy-2-methylphenyl)methanone Chemical compound C1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl KDIMAGCIYZVIFU-UHFFFAOYSA-N 0.000 description 3
- YFFPZSOWERDSHT-UHFFFAOYSA-N (2,6-dichlorophenyl)-(4-methoxy-2-methylphenyl)methanone Chemical compound CC1=CC(OC)=CC=C1C(=O)C1=C(Cl)C=CC=C1Cl YFFPZSOWERDSHT-UHFFFAOYSA-N 0.000 description 3
- JWCFPWFJLSCCMA-UHFFFAOYSA-N (2-butoxy-3,4-dimethoxy-6-methylphenyl)-(2,6-dichlorophenyl)methanone Chemical compound CCCCOC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl JWCFPWFJLSCCMA-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 241000235349 Ascomycota Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 206010017533 Fungal infection Diseases 0.000 description 3
- 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 3
- 244000141359 Malus pumila Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000498271 Necator Species 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 239000003480 eluent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
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- 239000002736 nonionic surfactant Substances 0.000 description 3
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- 229940051841 polyoxyethylene ether Drugs 0.000 description 3
- 229920000056 polyoxyethylene ether Polymers 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
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- ZWGVDVVCYIIJCV-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2,3-dihydroxy-4-methoxy-6-methylphenyl)methanone Chemical compound OC1=C(O)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl ZWGVDVVCYIIJCV-UHFFFAOYSA-N 0.000 description 2
- INEVPXPRFWVENS-UHFFFAOYSA-N (2,6-dichlorophenyl)-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)methanone Chemical compound OC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl INEVPXPRFWVENS-UHFFFAOYSA-N 0.000 description 2
- DRJYPXXNCFTWKE-UHFFFAOYSA-N (2,6-dichlorophenyl)-(4,5-dimethoxy-2-nitrophenyl)methanone Chemical compound C1=C(OC)C(OC)=CC(C(=O)C=2C(=CC=CC=2Cl)Cl)=C1[N+]([O-])=O DRJYPXXNCFTWKE-UHFFFAOYSA-N 0.000 description 2
- XWOOQGBQMJJCAB-UHFFFAOYSA-N (2,6-dichlorophenyl)-(4-methoxy-2-methyl-5-nitrophenyl)methanone Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C)=C1C(=O)C1=C(Cl)C=CC=C1Cl XWOOQGBQMJJCAB-UHFFFAOYSA-N 0.000 description 2
- BCABBCPYRIVZRE-UHFFFAOYSA-N (2-amino-4,5-dimethoxyphenyl)-(2,6-dichlorophenyl)methanone Chemical compound C1=C(OC)C(OC)=CC(N)=C1C(=O)C1=C(Cl)C=CC=C1Cl BCABBCPYRIVZRE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000895523 Blumeria graminis f. sp. hordei Species 0.000 description 2
- 229910021532 Calcite Inorganic materials 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
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- 230000003197 catalytic effect Effects 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
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- FKLFBQCQQYDUAM-UHFFFAOYSA-N fenpiclonil Chemical compound ClC1=CC=CC(C=2C(=CNC=2)C#N)=C1Cl FKLFBQCQQYDUAM-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
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- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
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- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
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- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
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- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 235000019355 sepiolite Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 235000020354 squash Nutrition 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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
- 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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- 150000003738 xylenes Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
- A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
-
- 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
-
- 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
- A01N35/08—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 at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—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 at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
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- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP95100792 | 1995-01-20 | ||
US08/479,502 US5679866A (en) | 1995-01-20 | 1995-06-07 | Fungicidal methods, compounds and compositions containing benzophenones |
Publications (2)
Publication Number | Publication Date |
---|---|
SK7496A3 SK7496A3 (en) | 1996-11-06 |
SK285301B6 true SK285301B6 (sk) | 2006-10-05 |
Family
ID=26138409
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK74-96A SK285301B6 (sk) | 1995-01-20 | 1996-01-17 | Fungicídny prostriedok, spôsob ochrany rastlín, benzofenónové zlúčeniny a spôsob ich výroby |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0727141B1 (es) |
JP (1) | JP3895795B2 (es) |
CN (1) | CN1159278C (es) |
AT (1) | ATE308241T1 (es) |
AU (1) | AU4209196A (es) |
BR (1) | BR9600165A (es) |
CA (1) | CA2167550A1 (es) |
CZ (1) | CZ294096B6 (es) |
DE (1) | DE69635363T2 (es) |
DK (1) | DK0727141T3 (es) |
ES (1) | ES2248803T3 (es) |
HU (1) | HU225219B1 (es) |
IL (1) | IL116818A (es) |
RO (1) | RO117827B1 (es) |
SK (1) | SK285301B6 (es) |
TW (1) | TW391957B (es) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9620202D0 (en) * | 1996-09-27 | 1996-11-13 | Rhone Poulenc Agriculture | New herbicides |
EP0899255B1 (en) * | 1997-08-20 | 2003-04-02 | Basf Aktiengesellschaft | Fungicidal 2,6,6'-trimethylbenzophenones |
US5945567A (en) * | 1997-08-20 | 1999-08-31 | American Cyanamid Company | Fungicidal 2-methoxybenzophenones |
US6242498B1 (en) | 1997-08-20 | 2001-06-05 | Juergen Curtze | Fungicidal 2,6,6′-trimethylbenzophenones |
US6001883A (en) * | 1998-06-24 | 1999-12-14 | American Cyanamid Company | Fungicidal 2-methoxybenzophenones |
EP0897904B1 (en) * | 1997-08-20 | 2002-02-20 | Basf Aktiengesellschaft | Fungicidal 2-methoxybenzophenones |
DE69912193T2 (de) * | 1998-06-24 | 2004-07-29 | Basf Ag | Substituierte 2-Hydroxybenzophenone, ihre Herstellung, ihre Verwendung als fungizide und ihre fungizide Zusammensetzungen |
US6444618B1 (en) | 1999-01-29 | 2002-09-03 | Basf Aktiengesellschaft | Crop protection emulsifiable concentrate containing defoaming agents |
EP1025757B1 (en) * | 1999-01-29 | 2005-11-09 | BASF Agro B.V., Arnhem (NL), Wädenswil-Branch | Crop protection emulsifiable concentrate containing defoaming agents |
EP1023835B1 (en) * | 1999-01-29 | 2004-08-04 | Basf Aktiengesellschaft | Enhancement of the efficacy of benzoylbenzenes |
DK1023832T3 (da) * | 1999-01-29 | 2005-02-21 | Basf Ag | Vandigt suspensionskoncentrat |
US6346535B1 (en) * | 1999-01-29 | 2002-02-12 | American Cyanamid Company | Fungicidal mixtures |
US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
JP2003500432A (ja) | 1999-06-01 | 2003-01-07 | ザ・ユニバーシティ・オブ・テキサス・サウスウエスタン・メディカル・センター | ジフェニルエーテル誘導体を用いて脱毛症を処置する方法 |
WO2000072810A1 (en) | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using sulfonyl thyromimetic 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 |
PT1353554E (pt) * | 2001-01-18 | 2004-11-30 | Basf Ag | Misturas fungicidas |
DK1365652T3 (da) * | 2001-01-18 | 2010-03-22 | Basf Se | Fungicide blandinger af benzophenoner og N-biphenylnikotinamider |
EP1373181A1 (de) * | 2001-03-13 | 2004-01-02 | Basf Aktiengesellschaft | Benzophenone, deren herstellung und verwendung zur bekämpfung von pflanzenpathogenen pilzen |
DE50200390D1 (de) * | 2001-10-31 | 2004-06-03 | Basf Ag | Benzhydrylderivate |
CA2708937C (en) * | 2002-03-21 | 2012-10-23 | Basf Aktiengesellschaft | Fungicidal mixtures |
ATE420555T1 (de) * | 2002-07-11 | 2009-01-15 | Basf Se | Fungizide verwendung |
TW200637839A (en) | 2005-01-07 | 2006-11-01 | Taisho Pharmaceutical Co Ltd | 1-thio-d-glucitol derivatives |
JP2011195561A (ja) * | 2009-11-24 | 2011-10-06 | Sumitomo Chemical Co Ltd | ケトン化合物及びそれを含有する除草剤 |
JP2011195562A (ja) * | 2009-11-26 | 2011-10-06 | Sumitomo Chemical Co Ltd | フェニルエステル化合物およびそれを含有する有害生物防除剤 |
JP5890297B2 (ja) * | 2011-12-22 | 2016-03-22 | 東京応化工業株式会社 | 感光性樹脂組成物、それを用いたカラーフィルタ及び表示装置、オキシムエステル化合物、並びに光重合開始剤 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2963399A (en) * | 1954-06-29 | 1960-12-06 | Diamond Alkali Co | Fungicidal polychlorobenzophenone oximes |
US3349133A (en) * | 1963-12-26 | 1967-10-24 | Dow Chemical Co | Derivatives of substituted benzophenone |
CH1093769A4 (es) * | 1969-07-17 | 1971-01-29 | ||
JPS511635A (ja) * | 1974-06-27 | 1976-01-08 | Nippon Kayaku Kk | Josozai |
DE2964343D1 (en) * | 1978-06-08 | 1983-01-27 | Shell Int Research | Benzoin oxime derivatives, process for their preparation, compositions containing such derivatives and method for their use as fungicides |
GR75464B (es) * | 1981-04-24 | 1984-07-20 | Ciba Geigy | |
EP0107623A1 (de) * | 1982-10-22 | 1984-05-02 | Ciba-Geigy Ag | Neue Benzodioxolderivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen |
ZA87704B (en) * | 1986-02-08 | 1987-09-30 | Nissan Chemical Ind Ltd | Pyridazinone derivatives,preparation thereof,and insecticidal,acaricidal,nematicidal,fungicidal compositions |
JPS63112566A (ja) * | 1986-10-28 | 1988-05-17 | Nissan Chem Ind Ltd | ピリミジノン誘導体、その製法および殺虫・殺ダニ・殺菌剤 |
DE3643403A1 (de) * | 1986-12-19 | 1988-06-30 | Shell Agrar Gmbh & Co Kg | Benzophenone und verfahren zu ihrer herstellung |
JPH01261371A (ja) * | 1988-04-13 | 1989-10-18 | Nissan Chem Ind Ltd | 含窒素複素環化合物および病害虫防除剤 |
CA2020888A1 (en) * | 1989-07-27 | 1991-01-28 | Philippe Guerry | Substituted aminoalkoxybenzene derivatives |
IT1250436B (it) * | 1991-07-01 | 1995-04-07 | Mini Ricerca Scient Tecnolog | Benzofenoni ad azione antifungina |
JPH0687812A (ja) * | 1992-09-04 | 1994-03-29 | Chisso Corp | 生理活性を有するオキシム類およびそれらのo−アシル誘導体 |
JPH07309825A (ja) * | 1994-05-19 | 1995-11-28 | Sumitomo Chem Co Ltd | オキシムエーテル誘導体、その用途およびその製造中間体 |
-
1996
- 1996-01-11 CZ CZ199689A patent/CZ294096B6/cs not_active IP Right Cessation
- 1996-01-15 DK DK96300285T patent/DK0727141T3/da active
- 1996-01-15 EP EP96300285A patent/EP0727141B1/en not_active Expired - Lifetime
- 1996-01-15 DE DE69635363T patent/DE69635363T2/de not_active Expired - Fee Related
- 1996-01-15 AT AT96300285T patent/ATE308241T1/de not_active IP Right Cessation
- 1996-01-15 ES ES96300285T patent/ES2248803T3/es not_active Expired - Lifetime
- 1996-01-17 SK SK74-96A patent/SK285301B6/sk unknown
- 1996-01-18 CA CA002167550A patent/CA2167550A1/en not_active Abandoned
- 1996-01-18 IL IL116818A patent/IL116818A/en not_active IP Right Cessation
- 1996-01-19 AU AU42091/96A patent/AU4209196A/en not_active Abandoned
- 1996-01-19 HU HU9600116A patent/HU225219B1/hu not_active IP Right Cessation
- 1996-01-19 JP JP02604796A patent/JP3895795B2/ja not_active Expired - Fee Related
- 1996-01-19 RO RO96-00100A patent/RO117827B1/ro unknown
- 1996-01-19 BR BR9600165A patent/BR9600165A/pt not_active IP Right Cessation
- 1996-01-22 CN CNB961010142A patent/CN1159278C/zh not_active Expired - Fee Related
- 1996-03-12 TW TW085102973A patent/TW391957B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0727141A3 (en) | 1998-01-28 |
DE69635363D1 (de) | 2005-12-08 |
IL116818A0 (en) | 1996-05-14 |
JP3895795B2 (ja) | 2007-03-22 |
ES2248803T3 (es) | 2006-03-16 |
ATE308241T1 (de) | 2005-11-15 |
CZ294096B6 (cs) | 2004-10-13 |
RO117827B1 (ro) | 2002-08-30 |
DE69635363T2 (de) | 2006-07-27 |
AU4209196A (en) | 1996-08-01 |
CN1134929A (zh) | 1996-11-06 |
CA2167550A1 (en) | 1996-07-21 |
EP0727141B1 (en) | 2005-11-02 |
IL116818A (en) | 2006-12-31 |
HUP9600116A3 (en) | 1999-03-01 |
HU225219B1 (en) | 2006-08-28 |
CN1159278C (zh) | 2004-07-28 |
HU9600116D0 (en) | 1996-03-28 |
HUP9600116A2 (en) | 1996-11-28 |
TW391957B (en) | 2000-06-01 |
JPH08277243A (ja) | 1996-10-22 |
EP0727141A2 (en) | 1996-08-21 |
DK0727141T3 (da) | 2006-01-16 |
SK7496A3 (en) | 1996-11-06 |
BR9600165A (pt) | 1998-01-06 |
CZ8996A3 (en) | 1996-08-14 |
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