PL216410B1 - Difluorometylotiazolilokarboksyanilidy, sposób ich wytwarzania, środek do zwalczania niepożądanych mikroorganizmów, zastosowanie difluorometylotiazolilokarboksyanilidów, sposób zwalczania niepożądanych mikroorganizmów oraz sposób wytwarzania środków do zwalczania niepożądanych mikroorganizmów, fluorowcoanilidy kwasu difluorometylotiazolilokarboksylowego, sposób wytwarzania fluorowcoanilidów kwasu difluorometylotiazolilokarboksylowego i pochodne kwasu difluorometylotiazolilokarboksyanilidoboronowego i sposób ich wytwarzania - Google Patents

Info

Publication number

PL216410B1

PL216410B1 PL371582A PL37158203A PL216410B1 PL 216410 B1 PL216410 B1 PL 216410B1 PL 371582 A PL371582 A PL 371582A PL 37158203 A PL37158203 A PL 37158203A PL 216410 B1 PL216410 B1 PL 216410B1

Authority

PL

Poland

Prior art keywords

formula

hydrogen

difluoromethylthiazolylcarboxanilides

methyl

acid

Prior art date

2002-02-04

Links

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• -1 Difluoromethyl thiazolyl Chemical group 0.000 title claims description 69
• 238000000034 method Methods 0.000 claims abstract description 55
• 230000008569 process Effects 0.000 claims abstract description 35
• 244000005700 microbiome Species 0.000 claims abstract description 31
• 238000002360 preparation method Methods 0.000 claims abstract description 20
• 239000001257 hydrogen Substances 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 239000000460 chlorine Substances 0.000 claims description 25
• 239000002253 acid Substances 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• BPONVVSBNSWOGF-UHFFFAOYSA-N 4-(difluoromethyl)-1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC(C(F)F)=CS1 BPONVVSBNSWOGF-UHFFFAOYSA-N 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 239000003085 diluting agent Substances 0.000 claims description 17
• 150000001642 boronic acid derivatives Chemical class 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 9
• 239000011230 binding agent Substances 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• UBPDKIDWEADHPP-UHFFFAOYSA-N 2-iodoaniline Chemical compound NC1=CC=CC=C1I UBPDKIDWEADHPP-UHFFFAOYSA-N 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 claims description 5
• 150000001448 anilines Chemical class 0.000 claims description 5
• 150000005171 halobenzenes Chemical class 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 239000004094 surface-active agent Substances 0.000 claims description 5
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 239000000126 substance Substances 0.000 abstract description 17
• 239000000543 intermediate Substances 0.000 abstract description 3
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• 239000013543 active substance Substances 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 230000009471 action Effects 0.000 description 13
• 239000000463 material Substances 0.000 description 13
• 238000012360 testing method Methods 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
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• 241000894006 Bacteria Species 0.000 description 5
• 241001465180 Botrytis Species 0.000 description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
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• NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
• QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
• WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 4
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