PL200802B1 - Pirazolo-karboksyanilidy, sposób ich wytwarzania, środek do zwalczania niepożądanych mikroorganizmów, zastosowanie pirazolo-karboksyanilidów, sposób zwalczania niepożądanych mikroorganizmów i sposób wytwarzania środka do zwalczania niepożądanych mikroorganizmów - Google Patents

Info

Publication number

PL200802B1

PL200802B1 PL346867A PL34686799A PL200802B1 PL 200802 B1 PL200802 B1 PL 200802B1 PL 346867 A PL346867 A PL 346867A PL 34686799 A PL34686799 A PL 34686799A PL 200802 B1 PL200802 B1 PL 200802B1

Authority

PL

Poland

Prior art keywords

carbon atoms

atoms

chlorine

bromine

pyrazole

Prior art date

1998-09-04

Links

• Espacenet
• Global Dossier
• Discuss

• 244000005700 microbiome Species 0.000 title claims abstract description 24
• WMZYZYFPPQOFKY-UHFFFAOYSA-N n-phenyl-1h-pyrazole-3-carboxamide Chemical compound C1=CNN=C1C(=O)NC1=CC=CC=C1 WMZYZYFPPQOFKY-UHFFFAOYSA-N 0.000 title claims abstract description 18
• 238000004519 manufacturing process Methods 0.000 title abstract description 4
• 239000000417 fungicide Substances 0.000 title description 6
• 230000000855 fungicidal effect Effects 0.000 title description 4
• 238000000034 method Methods 0.000 claims abstract description 20
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• 239000000460 chlorine Substances 0.000 claims description 28
• 229910052801 chlorine Inorganic materials 0.000 claims description 24
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
• 239000011737 fluorine Substances 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 238000002360 preparation method Methods 0.000 claims description 20
• 239000000463 material Substances 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
• 125000001246 bromo group Chemical group Br* 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 11
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 239000011230 binding agent Substances 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical group 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 150000004820 halides Chemical class 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• 239000004094 surface-active agent Substances 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 150000007529 inorganic bases Chemical class 0.000 claims description 3
• 150000007530 organic bases Chemical class 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 239000000126 substance Substances 0.000 abstract description 4
• -1 alkaline earth metal acetates Chemical class 0.000 description 49
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• 239000004480 active ingredient Substances 0.000 description 23
• 150000001875 compounds Chemical class 0.000 description 23
• 239000013543 active substance Substances 0.000 description 22
• 238000012360 testing method Methods 0.000 description 18
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• 239000003995 emulsifying agent Substances 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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• 238000006243 chemical reaction Methods 0.000 description 8
• 238000009472 formulation Methods 0.000 description 8
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
• 238000005507 spraying Methods 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 241000220225 Malus Species 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 239000002023 wood Substances 0.000 description 6
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• 238000001228 spectrum Methods 0.000 description 5
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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• 239000003899 bactericide agent Substances 0.000 description 4
• 239000000969 carrier Substances 0.000 description 4
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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• 239000000843 powder Substances 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
• 241000221787 Erysiphe Species 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 241000228453 Pyrenophora Species 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
• 230000001070 adhesive effect Effects 0.000 description 3
• 235000021016 apples Nutrition 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• 239000010949 copper Substances 0.000 description 3
• 229910052802 copper Inorganic materials 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• 239000000975 dye Substances 0.000 description 3
• 150000002148 esters Chemical class 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 description 3
• 239000002917 insecticide Substances 0.000 description 3
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• 235000012054 meals Nutrition 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 235000010755 mineral Nutrition 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000000376 reactant Substances 0.000 description 3
• 239000002689 soil Substances 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
• NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
• OZSVBRVFXIOJSU-UHFFFAOYSA-N 2,6-dichloro-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(=O)C1=C(Cl)C=CC=C1Cl OZSVBRVFXIOJSU-UHFFFAOYSA-N 0.000 description 2
• UTCNKGRSWYBETH-UHFFFAOYSA-N 2-(4-bromophenyl)aniline Chemical compound NC1=CC=CC=C1C1=CC=C(Br)C=C1 UTCNKGRSWYBETH-UHFFFAOYSA-N 0.000 description 2
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• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 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
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• ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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• 239000012973 diazabicyclooctane Substances 0.000 description 2
• 229960003887 dichlorophen Drugs 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 description 2
• UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 2
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• PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 2
• 239000010985 leather Substances 0.000 description 2
• KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
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• 230000003641 microbiacidal effect Effects 0.000 description 2
• 239000011707 mineral Substances 0.000 description 2
• BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 2
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• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
• 239000003973 paint Substances 0.000 description 2
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• LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 2
• 239000006072 paste Substances 0.000 description 2
• LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
• 235000015497 potassium bicarbonate Nutrition 0.000 description 2
• 239000011736 potassium bicarbonate 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
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