DD157292A5 - Mittel zur behandlung von pilzinfektionen - Google Patents
Mittel zur behandlung von pilzinfektionen Download PDFInfo
- Publication number
- DD157292A5 DD157292A5 DD81226883A DD22688381A DD157292A5 DD 157292 A5 DD157292 A5 DD 157292A5 DD 81226883 A DD81226883 A DD 81226883A DD 22688381 A DD22688381 A DD 22688381A DD 157292 A5 DD157292 A5 DD 157292A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- tetrafluoroethoxy
- dinitro
- benzenamine
- hydrogen
- trifluoromethylphenyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 239000004480 active ingredient Substances 0.000 claims abstract description 16
- 125000006501 nitrophenyl group Chemical group 0.000 claims abstract description 13
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 claims abstract description 11
- 208000031888 Mycoses Diseases 0.000 claims abstract description 9
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 8
- -1 nitro, hydroxy, methoxy Chemical group 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000002689 soil Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- AEMOVBPNMUCPCN-UHFFFAOYSA-N 2,4-dinitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 AEMOVBPNMUCPCN-UHFFFAOYSA-N 0.000 claims description 2
- VJYXIRXTXVSVQZ-UHFFFAOYSA-N 4-nitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-2-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 VJYXIRXTXVSVQZ-UHFFFAOYSA-N 0.000 claims description 2
- ARLCASJIMZRISK-UHFFFAOYSA-N n-[2,4-dibromo-5-(1,1,2,2-tetrafluoroethoxy)phenyl]-2,4-dinitro-6-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC(OC(F)(F)C(F)F)=C(Br)C=C1Br ARLCASJIMZRISK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- XYGFFOOMFJEJQZ-UHFFFAOYSA-N n-[2,4-dichloro-5-(1,1,2,2-tetrafluoroethoxy)phenyl]-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC1=CC(OC(F)(F)C(F)F)=C(Cl)C=C1Cl XYGFFOOMFJEJQZ-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 85
- 230000000843 anti-fungal effect Effects 0.000 abstract description 11
- 229940121375 antifungal agent Drugs 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 6
- NLGHTLZQTKXJCF-UHFFFAOYSA-N 2,6-dinitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 NLGHTLZQTKXJCF-UHFFFAOYSA-N 0.000 abstract description 2
- PKZPACVOMCECPG-UHFFFAOYSA-N 3,5-dinitro-4-[3-(1,1,2,2-tetrafluoroethoxy)anilino]benzoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)O)=CC([N+]([O-])=O)=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 PKZPACVOMCECPG-UHFFFAOYSA-N 0.000 abstract description 2
- KSMGLGUKJQFKIM-UHFFFAOYSA-N 3,5-dinitro-4-[2-(1,1,2,2-tetrafluoroethoxy)anilino]benzonitrile Chemical compound [O-][N+](=O)C1=CC(C#N)=CC([N+]([O-])=O)=C1NC1=CC=CC=C1OC(F)(F)C(F)F KSMGLGUKJQFKIM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003939 benzylamines Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 238000004458 analytical method Methods 0.000 description 26
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- 241001361634 Rhizoctonia Species 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 10
- 241000223218 Fusarium Species 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 244000046052 Phaseolus vulgaris Species 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000233639 Pythium Species 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- 241000233866 Fungi Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 238000003756 stirring Methods 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 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
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- 230000002140 halogenating effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
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- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- GRDIVJPQARIBNZ-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethoxybenzene Chemical compound FC(F)C(F)(F)OC1=CC=CC=C1 GRDIVJPQARIBNZ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WPXFYBKMJQLQMD-UHFFFAOYSA-N 2,4-dinitro-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 WPXFYBKMJQLQMD-UHFFFAOYSA-N 0.000 description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
- MUSFRWGGGZNTGC-UHFFFAOYSA-N 2-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound NC1=CC=CC=C1OC(F)(F)C(F)F MUSFRWGGGZNTGC-UHFFFAOYSA-N 0.000 description 2
- MWDPEBMCVXNSPL-UHFFFAOYSA-N 3-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound NC1=CC=CC(OC(F)(F)C(F)F)=C1 MWDPEBMCVXNSPL-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 235000012255 calcium oxide Nutrition 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
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- 238000001704 evaporation Methods 0.000 description 2
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- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- RARFQGFNESOKNO-UHFFFAOYSA-N n-[2,4-dibromo-5-(1,1,2,2-tetrafluoroethoxy)phenyl]-2,4,6-trinitroaniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC(OC(F)(F)C(F)F)=C(Br)C=C1Br RARFQGFNESOKNO-UHFFFAOYSA-N 0.000 description 2
- RSYYLGJIWYWCEP-UHFFFAOYSA-N n-methyl-2,4-dinitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C=1C=C([N+]([O-])=O)C=C(C(F)(F)F)C=1N(C)C1=CC=CC(OC(F)(F)C(F)F)=C1 RSYYLGJIWYWCEP-UHFFFAOYSA-N 0.000 description 2
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BPKRDKQVYYIRNM-UHFFFAOYSA-N 1-chloro-2-(1,1,2,2,2-pentafluoroethoxy)benzene Chemical compound FC(F)(F)C(F)(F)OC1=CC=CC=C1Cl BPKRDKQVYYIRNM-UHFFFAOYSA-N 0.000 description 1
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 1
- MYDJIRRBLQLQCH-UHFFFAOYSA-N 2,3-dinitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C([N+]([O-])=O)=C1[N+]([O-])=O MYDJIRRBLQLQCH-UHFFFAOYSA-N 0.000 description 1
- ISUJMKXVGGXXCW-UHFFFAOYSA-N 2,4,6-trinitro-n-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=CC=C1OC(F)(F)C(F)F ISUJMKXVGGXXCW-UHFFFAOYSA-N 0.000 description 1
- HOCXTEZXMSALQQ-UHFFFAOYSA-N 2,4,6-trinitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 HOCXTEZXMSALQQ-UHFFFAOYSA-N 0.000 description 1
- YPSPTUFTJNEDMW-UHFFFAOYSA-N 2,4,6-trinitro-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 YPSPTUFTJNEDMW-UHFFFAOYSA-N 0.000 description 1
- SDAPUHKEIUYJOI-UHFFFAOYSA-N 2,6-dinitro-n-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC1=CC=CC=C1OC(F)(F)C(F)F SDAPUHKEIUYJOI-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- HDVUPIFFKAHPJY-UHFFFAOYSA-N 2-butylaniline Chemical compound CCCCC1=CC=CC=C1N HDVUPIFFKAHPJY-UHFFFAOYSA-N 0.000 description 1
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- NDXFFSZJJQJIFQ-UHFFFAOYSA-N 2-tert-butyl-4,6-dinitro-N-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound CC(C)(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 NDXFFSZJJQJIFQ-UHFFFAOYSA-N 0.000 description 1
- KLRMPYZOPDQDHJ-UHFFFAOYSA-N 3,5-dinitro-2-[2-(1,1,2,2-tetrafluoroethoxy)anilino]benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1NC1=CC=CC=C1OC(F)(F)C(F)F KLRMPYZOPDQDHJ-UHFFFAOYSA-N 0.000 description 1
- JIORURQZXYUYKZ-UHFFFAOYSA-N 3,5-dinitro-2-[4-(1,1,2,2-tetrafluoroethoxy)anilino]benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 JIORURQZXYUYKZ-UHFFFAOYSA-N 0.000 description 1
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- NRJXAZHQFNXXET-UHFFFAOYSA-N 3-bromo-2,4-dinitro-n-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=C(Br)C([N+](=O)[O-])=CC(C(F)(F)F)=C1NC1=CC=C(OC(F)(F)C(F)(F)F)C=C1 NRJXAZHQFNXXET-UHFFFAOYSA-N 0.000 description 1
- KPNHSIZLNLOMQO-UHFFFAOYSA-N 3-bromo-2,6-dinitro-n-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Br)C([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)(F)F)C=C1 KPNHSIZLNLOMQO-UHFFFAOYSA-N 0.000 description 1
- BBWFPLOVPMWNFV-UHFFFAOYSA-N 3-chloro-2,4-dinitro-n-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=C(Cl)C([N+](=O)[O-])=CC(C(F)(F)F)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 BBWFPLOVPMWNFV-UHFFFAOYSA-N 0.000 description 1
- XKGREQGNYSMQCM-UHFFFAOYSA-N 3-nitro-4-[4-(1,1,2,2-tetrafluoroethoxy)anilino]benzoic acid Chemical compound [O-][N+](=O)C1=CC(C(=O)O)=CC=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 XKGREQGNYSMQCM-UHFFFAOYSA-N 0.000 description 1
- MDODMMABKXPUEN-UHFFFAOYSA-N 4-(1,1,2,2,2-pentafluoroethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)C(F)(F)F)C=C1 MDODMMABKXPUEN-UHFFFAOYSA-N 0.000 description 1
- ZQQSVTYLRGGCEI-UHFFFAOYSA-N 4-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound NC1=CC=C(OC(F)(F)C(F)F)C=C1 ZQQSVTYLRGGCEI-UHFFFAOYSA-N 0.000 description 1
- FSLMJGSGGMNAJB-UHFFFAOYSA-N 4-tert-butyl-2,6-dinitro-N-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC(C(C)(C)C)=CC([N+]([O-])=O)=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 FSLMJGSGGMNAJB-UHFFFAOYSA-N 0.000 description 1
- REFNGYJRTXPIJO-UHFFFAOYSA-N 4-tert-butyl-2,6-dinitro-N-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC(C(C)(C)C)=CC([N+]([O-])=O)=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 REFNGYJRTXPIJO-UHFFFAOYSA-N 0.000 description 1
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- 229910021532 Calcite Inorganic materials 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
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- XKLSTZYSMCDSOM-UHFFFAOYSA-N n-[2,6-dichloro-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2,4-dinitro-6-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NC1=C(Cl)C=C(OC(F)(F)C(F)F)C=C1Cl XKLSTZYSMCDSOM-UHFFFAOYSA-N 0.000 description 1
- AOQHMCJCONNUJA-UHFFFAOYSA-N n-[4-bromo-2-chloro-5-(1,1,2,2,2-pentafluoroethoxy)phenyl]-2,6-dinitro-4-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1NC1=CC(OC(F)(F)C(F)(F)F)=C(Br)C=C1Cl AOQHMCJCONNUJA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZQAGEGZFIFFCY-UHFFFAOYSA-N n-ethyl-2,4,6-trinitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C=1C=C([N+]([O-])=O)C=C([N+]([O-])=O)C=1N(CC)C1=CC=CC(OC(F)(F)C(F)F)=C1 YZQAGEGZFIFFCY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
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- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZMJJCODMIXQWCQ-UHFFFAOYSA-N potassium;di(propan-2-yl)azanide Chemical compound [K+].CC(C)[N-]C(C)C ZMJJCODMIXQWCQ-UHFFFAOYSA-N 0.000 description 1
- OSISGTVOYWZXIF-UHFFFAOYSA-N propan-2-yl 3-nitro-4-[4-(1,1,2,2-tetrafluoroethoxy)anilino]benzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC(C)C)=CC=C1NC1=CC=C(OC(F)(F)C(F)F)C=C1 OSISGTVOYWZXIF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- 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
-
- 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
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/03—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C205/04—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| US06/110,308 US4304791A (en) | 1980-01-08 | 1980-01-08 | Benzenamines, formulations, and fungicidal method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD157292A5 true DD157292A5 (de) | 1982-11-03 |
Family
ID=22332322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD81226883A DD157292A5 (de) | 1980-01-08 | 1981-01-08 | Mittel zur behandlung von pilzinfektionen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4304791A (el) |
| KR (1) | KR840001232B1 (el) |
| CA (1) | CA1164339A (el) |
| CS (1) | CS221812B2 (el) |
| DD (1) | DD157292A5 (el) |
| EG (1) | EG14795A (el) |
| FI (1) | FI810025L (el) |
| GR (1) | GR72310B (el) |
| HU (1) | HU187757B (el) |
| PH (1) | PH16393A (el) |
| PL (1) | PL124733B1 (el) |
| PT (1) | PT72315B (el) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4366168A (en) * | 1981-09-21 | 1982-12-28 | Eli Lilly And Company | Anticoccidial combinations |
| US4423065A (en) * | 1982-05-04 | 1983-12-27 | Eli Lilly And Company | Naphthalenamine insecticides |
| US4670596A (en) * | 1983-08-01 | 1987-06-02 | Eli Lilly And Company | Diphenylamine compounds |
| US4690980A (en) * | 1985-07-17 | 1987-09-01 | Ppg Industries, Inc. | Acrylic modified polymers |
| CN102199095B (zh) | 2010-03-22 | 2014-04-09 | 中国中化股份有限公司 | 一种取代二苯胺类化合物及其制备与应用 |
| KR101599300B1 (ko) | 2012-03-14 | 2016-03-03 | 시노켐 코포레이션 | 치환 디페닐아민 화합물 및 항종양제로서의 용도 |
| CN108976167B (zh) * | 2017-06-02 | 2021-12-07 | 沈阳中化农药化工研发有限公司 | 一种取代苯肼类化合物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2728536A1 (de) * | 1977-06-24 | 1979-01-11 | Bayer Ag | Neue 2-arylamino-3,5-dinitro- benzotrifluoride |
| DE2815290A1 (de) * | 1978-04-08 | 1979-10-18 | Bayer Ag | Neue diarylamine, verfahren zu ihrer herstellung und ihre verwendung |
-
1980
- 1980-01-08 US US06/110,308 patent/US4304791A/en not_active Expired - Lifetime
-
1981
- 1981-01-06 PT PT72315A patent/PT72315B/pt unknown
- 1981-01-07 KR KR1019810000026A patent/KR840001232B1/ko active
- 1981-01-07 FI FI810025A patent/FI810025L/fi not_active Application Discontinuation
- 1981-01-07 PH PH25061A patent/PH16393A/en unknown
- 1981-01-07 GR GR63799A patent/GR72310B/el unknown
- 1981-01-07 HU HU8130A patent/HU187757B/hu unknown
- 1981-01-07 CA CA000368024A patent/CA1164339A/en not_active Expired
- 1981-01-07 EG EG8103A patent/EG14795A/xx active
- 1981-01-07 CS CS81128A patent/CS221812B2/cs unknown
- 1981-01-08 DD DD81226883A patent/DD157292A5/de unknown
- 1981-01-08 PL PL1981229119A patent/PL124733B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL124733B1 (en) | 1983-02-28 |
| CA1164339A (en) | 1984-03-27 |
| EG14795A (en) | 1985-03-31 |
| HU187757B (en) | 1986-02-28 |
| GR72310B (el) | 1983-10-19 |
| PH16393A (en) | 1983-09-22 |
| PL229119A1 (el) | 1981-09-04 |
| FI810025L (fi) | 1981-07-09 |
| PT72315A (en) | 1981-02-01 |
| CS221812B2 (en) | 1983-04-29 |
| KR840001232B1 (ko) | 1984-08-23 |
| KR830005104A (ko) | 1983-07-23 |
| US4304791A (en) | 1981-12-08 |
| PT72315B (en) | 1981-12-17 |
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