NZ534454A - Difluoromethyl thiazolyl carboxanilides - Google Patents

Info

Publication number

NZ534454A

NZ534454A NZ534454A NZ53445403A NZ534454A NZ 534454 A NZ534454 A NZ 534454A NZ 534454 A NZ534454 A NZ 534454A NZ 53445403 A NZ53445403 A NZ 53445403A NZ 534454 A NZ534454 A NZ 534454A

Authority

NZ

New Zealand

Prior art keywords

formula

represent hydrogen

difluoromethylthiazolylcarboxanilides

methyl

bromine

Prior art date

2002-02-04

Links

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• -1 Difluoromethyl thiazolyl Chemical group 0.000 title claims abstract description 80
• 238000000034 method Methods 0.000 claims abstract description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
• 239000001257 hydrogen Substances 0.000 claims abstract description 41
• 244000005700 microbiome Species 0.000 claims abstract description 23
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 11
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
• 150000002367 halogens Chemical group 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
• 125000004450 alkenylene group Chemical class 0.000 claims abstract description 3
• 125000005843 halogen group Chemical group 0.000 claims abstract description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 70
• 230000008569 process Effects 0.000 claims description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 239000000203 mixture Substances 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 claims description 16
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
• 239000000460 chlorine Chemical group 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 150000001642 boronic acid derivatives Chemical class 0.000 claims description 13
• 239000011737 fluorine Chemical group 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 238000012360 testing method Methods 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 239000003085 diluting agent Substances 0.000 claims description 10
• 239000011230 binding agent Substances 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 241000813090 Rhizoctonia solani Species 0.000 claims description 6
• 241001360088 Zymoseptoria tritici Species 0.000 claims description 6
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• 239000004606 Fillers/Extenders Substances 0.000 claims description 5
• 150000001448 anilines Chemical class 0.000 claims description 5
• 125000001246 bromo group Chemical group Br* 0.000 claims description 5
• 150000005171 halobenzenes Chemical class 0.000 claims description 5
• 239000011630 iodine Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• BLLGDDLTTAIIQY-UHFFFAOYSA-N anilinoboronic acid Chemical class OB(O)NC1=CC=CC=C1 BLLGDDLTTAIIQY-UHFFFAOYSA-N 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
• 241000196324 Embryophyta Species 0.000 description 69
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 238000002360 preparation 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
• 239000000126 substance Substances 0.000 description 12
• 240000008042 Zea mays Species 0.000 description 11
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 11
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
• 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 11
• 230000001965 increasing effect Effects 0.000 description 11
• 235000009973 maize Nutrition 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• 241000233866 Fungi Species 0.000 description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• 230000001681 protective effect Effects 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000003995 emulsifying agent Substances 0.000 description 9
• 229920000742 Cotton Polymers 0.000 description 8
• 244000299507 Gossypium hirsutum Species 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• 238000009472 formulation Methods 0.000 description 7
• 108090000623 proteins and genes Proteins 0.000 description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• 235000010469 Glycine max Nutrition 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 238000006243 chemical reaction Methods 0.000 description 6
• 239000008187 granular material 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
• 239000002689 soil Substances 0.000 description 6
• 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
• 241000220225 Malus Species 0.000 description 5
• 244000061456 Solanum tuberosum Species 0.000 description 5
• 235000002595 Solanum tuberosum Nutrition 0.000 description 5
• 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 5
• 239000004305 biphenyl Substances 0.000 description 5
• 235000010290 biphenyl Nutrition 0.000 description 5
• 230000009261 transgenic effect Effects 0.000 description 5
• 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
• UBPDKIDWEADHPP-UHFFFAOYSA-N 2-iodoaniline Chemical compound NC1=CC=CC=C1I UBPDKIDWEADHPP-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
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• OSFPHMZQBQZLAY-UHFFFAOYSA-N OBO.NC1=CC=CC=C1 Chemical class OBO.NC1=CC=CC=C1 OSFPHMZQBQZLAY-UHFFFAOYSA-N 0.000 description 4
• 244000046052 Phaseolus vulgaris Species 0.000 description 4
• 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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