UA80115C2 - Disubstituted pyrazolyl carboxanilides, agent based thereon, method for combating undesired microorganisms and intermediates - Google Patents

Info

Publication number

UA80115C2

UA80115C2 UA20040907598A UA20040907598A UA80115C2 UA 80115 C2 UA80115 C2 UA 80115C2 UA 20040907598 A UA20040907598 A UA 20040907598A UA 20040907598 A UA20040907598 A UA 20040907598A UA 80115 C2 UA80115 C2 UA 80115C2

Authority

UA

Ukraine

Prior art keywords

formula

plants

methyl

fluorine

trifluoromethyl

Prior art date

2002-02-19

Links

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• Global Dossier
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• 244000005700 microbiome Species 0.000 title abstract description 15
• 125000003226 pyrazolyl group Chemical group 0.000 title abstract 2
• 238000000034 method Methods 0.000 title description 46
• 239000000543 intermediate Substances 0.000 title description 2
• 239000013067 intermediate product Substances 0.000 abstract description 2
• 238000004519 manufacturing process Methods 0.000 abstract description 2
• -1 trifluoroethoxy, difluoromethylthio, difluoromethylthio Chemical group 0.000 description 84
• 241000196324 Embryophyta Species 0.000 description 63
• 239000013543 active substance Substances 0.000 description 42
• 229910052731 fluorine Inorganic materials 0.000 description 41
• 239000011737 fluorine Substances 0.000 description 41
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 35
• 150000001875 compounds Chemical class 0.000 description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 29
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 25
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
• 229910052794 bromium Inorganic materials 0.000 description 25
• 239000000126 substance Substances 0.000 description 25
• 241000894007 species Species 0.000 description 23
• 239000000203 mixture Substances 0.000 description 21
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 20
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• 239000000460 chlorine Substances 0.000 description 20
• 229910052801 chlorine Inorganic materials 0.000 description 20
• 230000009471 action Effects 0.000 description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 239000000463 material Substances 0.000 description 15
• 239000000047 product Substances 0.000 description 12
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 11
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
• 235000005822 corn Nutrition 0.000 description 11
• 229910052740 iodine Inorganic materials 0.000 description 11
• 230000001681 protective effect Effects 0.000 description 11
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• 241000233866 Fungi Species 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 9
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
• 239000003995 emulsifying agent Substances 0.000 description 9
• 238000012545 processing Methods 0.000 description 9
• 108090000623 proteins and genes Proteins 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
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• 235000010469 Glycine max Nutrition 0.000 description 7
• 244000299507 Gossypium hirsutum Species 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• 239000003054 catalyst Substances 0.000 description 7
• 238000011160 research Methods 0.000 description 7
• WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 241000220225 Malus Species 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 230000003993 interaction Effects 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
• 241000700605 Viruses Species 0.000 description 5
• 241000607479 Yersinia pestis Species 0.000 description 5
• 239000004305 biphenyl Substances 0.000 description 5
• 235000010290 biphenyl Nutrition 0.000 description 5
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
• 239000012141 concentrate Substances 0.000 description 5
• 235000008504 concentrate Nutrition 0.000 description 5
• 239000010949 copper Substances 0.000 description 5
• 229910052802 copper Inorganic materials 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• 235000019439 ethyl acetate Nutrition 0.000 description 5
• 239000008187 granular material Substances 0.000 description 5
• 229910052736 halogen Inorganic materials 0.000 description 5
• 150000002367 halogens Chemical class 0.000 description 5
• 208000015181 infectious disease Diseases 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000011541 reaction mixture Substances 0.000 description 5
• 239000002689 soil Substances 0.000 description 5
• 238000001228 spectrum Methods 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 5
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
• KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 4
• 241000894006 Bacteria Species 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 244000061456 Solanum tuberosum Species 0.000 description 4
• 235000002595 Solanum tuberosum Nutrition 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 239000000370 acceptor Substances 0.000 description 4
• 150000001448 anilines Chemical class 0.000 description 4
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
• 235000021016 apples Nutrition 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
• 239000000417 fungicide Substances 0.000 description 4
• 150000004820 halides Chemical class 0.000 description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
• 239000007788 liquid Substances 0.000 description 4
• UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 229960003975 potassium Drugs 0.000 description 4
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• 238000002360 preparation method Methods 0.000 description 4
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• 229910052708 sodium Inorganic materials 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 238000003786 synthesis reaction Methods 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• 230000009261 transgenic effect Effects 0.000 description 4
• 239000002023 wood Substances 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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• 235000004977 Brassica sinapistrum Nutrition 0.000 description 3
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• 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
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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• 125000002877 alkyl aryl group Chemical group 0.000 description 3
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• KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 3
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• CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 2
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• FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
• 229910052782 aluminium Inorganic materials 0.000 description 2
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• 239000008346 aqueous phase Substances 0.000 description 2
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• 150000001491 aromatic compounds Chemical class 0.000 description 2
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