CS221812B2 - Fungicide means - Google Patents
Fungicide means Download PDFInfo
- Publication number
- CS221812B2 CS221812B2 CS81128A CS12881A CS221812B2 CS 221812 B2 CS221812 B2 CS 221812B2 CS 81128 A CS81128 A CS 81128A CS 12881 A CS12881 A CS 12881A CS 221812 B2 CS221812 B2 CS 221812B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- benzenamine
- dinitro
- atom
- tetrafluoroethoxy
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title claims description 14
- 239000000417 fungicide Substances 0.000 title abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 42
- -1 benzene compound Chemical class 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 241000233866 Fungi Species 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- IOYNQIMAUDJVEI-BMVIKAAMSA-N Tepraloxydim Chemical group C1C(=O)C(C(=N/OC\C=C\Cl)/CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-BMVIKAAMSA-N 0.000 claims 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 claims 1
- 241000219745 Lupinus Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 2
- 230000001165 anti-coccidial effect Effects 0.000 abstract 1
- 229940124536 anticoccidial agent Drugs 0.000 abstract 1
- 239000013057 ectoparasiticide Substances 0.000 abstract 1
- GSXGDTVOMVABCE-UHFFFAOYSA-N n-[3-phenyl-2-(1,2,2,2-tetrafluoroethoxy)phenyl]nitramide Chemical class [O-][N+](=O)NC1=CC=CC(C=2C=CC=CC=2)=C1OC(F)C(F)(F)F GSXGDTVOMVABCE-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000002689 soil Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 241001361634 Rhizoctonia Species 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 244000046052 Phaseolus vulgaris Species 0.000 description 13
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 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 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 241000223218 Fusarium Species 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000126 substance 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 101100022176 Mus musculus Gstz1 gene Proteins 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 244000053095 fungal pathogen Species 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000012871 anti-fungal composition Substances 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- 239000003209 petroleum derivative Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 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 2
- 238000009736 wetting Methods 0.000 description 2
- 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
- JREJWHNDQOGSQT-UHFFFAOYSA-N 1,2,3,4,5-pentaethylbenzene Chemical compound CCC1=CC(CC)=C(CC)C(CC)=C1CC JREJWHNDQOGSQT-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 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
- 125000004790 1-fluoroethoxy group Chemical group FC(C)O* 0.000 description 1
- YWMNQNPGQBJWOQ-UHFFFAOYSA-N 1-oxo-1-sulfanylidene-2-(trifluoromethyl)-1,2-benzothiazol-3-one Chemical compound C1=CC=C2S(=S)(=O)N(C(F)(F)F)C(=O)C2=C1 YWMNQNPGQBJWOQ-UHFFFAOYSA-N 0.000 description 1
- VYRFSCZAKSARGV-UHFFFAOYSA-N 2,4,6-trinitro-n-[3-(1,1,2,2,2-pentafluoroethoxy)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)F)=C1 VYRFSCZAKSARGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 description 1
- DWQTYBNDAJZRAZ-UHFFFAOYSA-N 2,6-dibromo-N-(4-tert-butyl-2-nitrophenyl)-4-(1,1,2,2-tetrafluoroethoxy)aniline Chemical compound [O-][N+](=O)C1=CC(C(C)(C)C)=CC=C1NC1=C(Br)C=C(OC(F)(F)C(F)F)C=C1Br DWQTYBNDAJZRAZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DHUNETVQJYHFMD-UHFFFAOYSA-N 2,6-dinitro-n-[4-(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=C(OC(F)(F)C(F)F)C=C1 DHUNETVQJYHFMD-UHFFFAOYSA-N 0.000 description 1
- CPTLDHXRWSDTGJ-UHFFFAOYSA-N 2-[2,4-dibromo-5-(1,1,2,2-tetrafluoroethoxy)anilino]-3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1NC1=CC(OC(F)(F)C(F)F)=C(Br)C=C1Br CPTLDHXRWSDTGJ-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
- DKQVVTKDZZPCHW-UHFFFAOYSA-N 2-bromo-6-chloro-n-(3,4-dinitrophenyl)-4-(1,1,2,2,2-pentafluoroethoxy)aniline Chemical compound C1=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C1NC1=C(Cl)C=C(OC(F)(F)C(F)(F)F)C=C1Br DKQVVTKDZZPCHW-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical class CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- SWYMSARJORHCRS-UHFFFAOYSA-N 2-nitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]aniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC(OC(F)(F)C(F)F)=C1 SWYMSARJORHCRS-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
- 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 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
- 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
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241001519020 Cassia brewsteri Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100347983 Mus musculus Napsa gene Proteins 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- 241001611408 Nebo Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- LDLYYQOONVPSFS-UHFFFAOYSA-N [O-][N+](NC(C=CC=C1C2=CC=CC=C2)=C1OC(C(F)(F)F)(F)F)=O Chemical class [O-][N+](NC(C=CC=C1C2=CC=CC=C2)=C1OC(C(F)(F)F)(F)F)=O LDLYYQOONVPSFS-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 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 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000035617 depilation Effects 0.000 description 1
- JYIMWRSJCRRYNK-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4] JYIMWRSJCRRYNK-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000021186 dishes Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- WYBBHMDQIBXFMH-UHFFFAOYSA-N ethyl 4-[n-ethyl-3-(1,1,2,2-tetrafluoroethoxy)anilino]-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OCC)=CC=C1N(CC)C1=CC=CC(OC(F)(F)C(F)F)=C1 WYBBHMDQIBXFMH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000006005 fluoroethoxy group Chemical group 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000000004 fungal plant pathogen Species 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000011630 iodine Substances 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
- 230000001418 larval effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DOIVMWNMXBTRLQ-UHFFFAOYSA-N n-[2,4-dichloro-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(Cl)C=C1Cl DOIVMWNMXBTRLQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QIXUFNWBHQXHDN-UHFFFAOYSA-N n-[3,5-dibromo-2-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-methyl-2,3,4-trinitroaniline Chemical compound [O-][N+](=O)C1=C([N+]([O-])=O)C(C)=CC(NC=2C(=C(Br)C=C(Br)C=2)OC(F)(F)C(F)F)=C1[N+]([O-])=O QIXUFNWBHQXHDN-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
- NFDNJLXLFKOLNX-UHFFFAOYSA-N n-ethyl-2,4-dinitro-n-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-6-(trifluoromethyl)aniline Chemical compound [O-][N+](=O)C=1C=C([N+]([O-])=O)C=C(C(F)(F)F)C=1N(CC)C1=CC=C(OC(F)(F)C(F)(F)F)C=C1 NFDNJLXLFKOLNX-UHFFFAOYSA-N 0.000 description 1
- ANOJDKSQEWTEGT-UHFFFAOYSA-N n-methyl-4-nitro-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)aniline Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1N(C)C1=CC=CC(OC(F)(F)C(F)F)=C1 ANOJDKSQEWTEGT-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
- 230000001069 nematicidal effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000003797 telogen phase Effects 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-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
- 239000004563 wettable powder Substances 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 |
|---|---|
| CS221812B2 true CS221812B2 (en) | 1983-04-29 |
Family
ID=22332322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS81128A CS221812B2 (en) | 1980-01-08 | 1981-01-07 | Fungicide means |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4304791A (de) |
| KR (1) | KR840001232B1 (de) |
| CA (1) | CA1164339A (de) |
| CS (1) | CS221812B2 (de) |
| DD (1) | DD157292A5 (de) |
| EG (1) | EG14795A (de) |
| FI (1) | FI810025L (de) |
| GR (1) | GR72310B (de) |
| HU (1) | HU187757B (de) |
| PH (1) | PH16393A (de) |
| PL (1) | PL124733B1 (de) |
| PT (1) | PT72315B (de) |
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 |
| CA2859842C (en) | 2012-03-14 | 2016-11-08 | Sinochem Corporation | Substitute diphenylamine compounds use thereof as antitumor agents |
| 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 FI FI810025A patent/FI810025L/fi not_active Application Discontinuation
- 1981-01-07 HU HU8130A patent/HU187757B/hu unknown
- 1981-01-07 CA CA000368024A patent/CA1164339A/en not_active Expired
- 1981-01-07 CS CS81128A patent/CS221812B2/cs unknown
- 1981-01-07 EG EG8103A patent/EG14795A/xx active
- 1981-01-07 PH PH25061A patent/PH16393A/en unknown
- 1981-01-07 GR GR63799A patent/GR72310B/el unknown
- 1981-01-07 KR KR1019810000026A patent/KR840001232B1/ko active
- 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 |
|---|---|
| PL229119A1 (de) | 1981-09-04 |
| DD157292A5 (de) | 1982-11-03 |
| PH16393A (en) | 1983-09-22 |
| PT72315A (en) | 1981-02-01 |
| KR830005104A (ko) | 1983-07-23 |
| US4304791A (en) | 1981-12-08 |
| PL124733B1 (en) | 1983-02-28 |
| GR72310B (de) | 1983-10-19 |
| FI810025L (fi) | 1981-07-09 |
| CA1164339A (en) | 1984-03-27 |
| EG14795A (en) | 1985-03-31 |
| PT72315B (en) | 1981-12-17 |
| KR840001232B1 (ko) | 1984-08-23 |
| HU187757B (en) | 1986-02-28 |
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